WO2024081762A1 - Cycles à 5 chaînons substitués et leur utilisation en tant que pesticides - Google Patents

Cycles à 5 chaînons substitués et leur utilisation en tant que pesticides Download PDF

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WO2024081762A1
WO2024081762A1 PCT/US2023/076654 US2023076654W WO2024081762A1 WO 2024081762 A1 WO2024081762 A1 WO 2024081762A1 US 2023076654 W US2023076654 W US 2023076654W WO 2024081762 A1 WO2024081762 A1 WO 2024081762A1
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alkyl
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composition
group
aryl
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PCT/US2023/076654
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English (en)
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Jared L. BELL
Allyson J. BOYINGTON
Aroop Chandra
Joseph D. Eckelbarger
Daniel G. KOHLER
Rajesh Kumar Mishra
Xuelin Wang
Jinpeng Zhao
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Corteva Agriscience Llc
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Publication of WO2024081762A1 publication Critical patent/WO2024081762A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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
    • A01P13/02—Herbicides; Algicides selective

Definitions

  • the molecules may include lactams or thiolactams, either of which may be substituted with a fluorinated benzyl group and other groups, such as an amino acid or other derivatives thereof.
  • the substituted 5-membered ring molecules are molecules of Formula (I): Formula (I) wherein: X is selected from the group consisting of O and S; Y is selected from the group consisting of O, NR 5 , and S; R 1 is selected from the group consisting of H and F; R 2 is selected from the group consisting of methyl and cyclopropyl; R 3 is selected from the group consisting of H, methyl, and methoxy; R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-
  • the lactam-based molecules are molecules of Formula (II): Formula (II) wherein: R 1 is selected from the group consisting of H and F; R 2 is selected from the group consisting of methyl and cyclopropyl; R 3 is selected from the group consisting of H, methyl, and methoxy; R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl-heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )-hal
  • the lactam-based molecules are molecules of Formula (III) Formula (III) wherein: R 1 is selected from the group consisting of H and F; R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl-heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )-alkyl, (C 1 - C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10
  • the thiolactam-based molecules are molecules of Formula (IV): Formula (IV) wherein: X is selected from the group consisting of O and S; R 1 is selected from the group consisting of H and F; R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl-heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )-alkyl, (C 1 - C 10 )-alkylthio-(C 1
  • the lactam-based molecules are molecules of Formula (V): Formula (V) wherein R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )- cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl- heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )- alkyl, (C 1 -C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyl-sulfonyl-(
  • the lactam-based molecules are molecules of Formula (VI): Formula (VI) wherein R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )- cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl- heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )- alkyl, (C 1 -C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyl-sulfonyl-(
  • the lactam-based molecules are molecules of Formula (VII): Formula (VII) wherein R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )- cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl- heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )- alkyl, (C 1 -C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyl-sulfonyl
  • the lactam-based molecules are molecules of Formula (VIII): Formula (VIII) wherein R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )- cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl- heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )- alkyl, (C 1 -C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyl-sulfonyl
  • the lactam-based molecules are molecules of Formula (IX): Formula (IX) wherein R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )- cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl- heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )- alkyl, (C 1 -C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyl-sulfonyl
  • the lactam-based molecules are molecules of Formula (X): Formula (X) wherein R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )- cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl- heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )- alkyl, (C 1 -C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyl-sulfonyl-(
  • FIGs.1A and 1B illustrate Table 5A and 5B that contains exemplary post-emergent data
  • FIG.1C illustrates Table 5C that contains exemplary pre-emergent data
  • FIG.2 illustrates Tables 6A and 6B that contains exemplary isomer data
  • FIG.3 illustrates Table 7 that contains exemplary broad leaf crop data
  • FIGs. 4A-4D illustrate Tables 8A-8D respectively that contain various mixtures with ALS herbicides according to various aspects
  • FIG. 5A-4D illustrate Tables 9A-9D respectively that contain various mixtures with auxin herbicides according to various aspects
  • FIGs. 6A and 6B illustrate Tables 10A and 10B respectively that contain various mixtures with HPPD herbicides according to various aspects
  • FIGs. 7A and 7B illustrate Tables 11A and 11B respectively that contain various mixtures with PPO herbicides according to various aspects
  • FIGs.8A-8D illustrate Tables 12A-12D respectively that contain various mixtures with ACCase herbicides according to various aspects
  • FIG. 9 illustrates Table 13 that contains various mixtures with MAI herbicides according to various aspects
  • FIG. 10 illustrates Table 14 that contains various mixtures with PSI herbicides according to various aspects
  • FIG. 11 illustrates Table 15 that contain various mixtures with PDS herbicides according to various aspects
  • FIG.12 illustrates Table 16 that contains various mixtures with VLCFA herbicides according to various aspects
  • FIG.13 illustrates Table 17 that contains various mixtures with DOXP herbicides according to various aspects
  • FIGs.14A and 14B illustrate Tables 18A and 18B respectively that contain various mixtures with PSII herbicides according to various aspects
  • FIG.15 illustrates Tables 19 that contains various mixtures with EPSPS herbicides according to various aspects
  • FIG. 16 illustrates Table 20 that contains various mixtures with GS herbicides according to various aspects
  • FIG. 17 illustrates Table 21 that contains comparative growth rated of various mixtures
  • FIGs. 18A and 18B illustrates Table 22A and Table 22B that contain additional herbicidal mixture data.
  • FIGs. contain exemplary data for various aspects of the present disclosure—in various forms—such exemplifications are not to be construed as limiting the scope of the disclosure in any manner.
  • the present disclosure includes molecules that may be used as herbicides to control undesirable vegetation in various locations, such as croplands, lawns, pastures, gardens, and recreational areas. These substituted 5-membered ring molecules, such as lactams or thio- lactams, may be substituted with fluorinated benzyl groups and other groups, such as amino acid groups or derivatives thereof.
  • the present disclosure also includes methods for using the molecules for controlling undesirable vegetation.
  • the undesirable vegetation is in row crops.
  • the undesirable vegetation is in maize, soy, canola, cotton, pulses, sunflower, sugar beet, wheat, barley, rice, sorghum, millet, or oats.
  • the molecules are graminicides used to control undesirable vegetation including grass-type species.
  • herbicide and “herbicidal active ingredient” refer to an active ingredient that kills, controls, or otherwise adversely modifies the growth of vegetation, particularly undesirable vegetation such as weed species, when applied in an appropriate amount.
  • herbicidal effect is an adversely modifying effect of an active ingredient on vegetation, including, for example, a deviation from natural growth or development, killing, regulation, desiccation, growth inhibition, growth reduction, and retardation.
  • herbicidal activity refers generally to herbicidal effects of an active ingredient.
  • the term “herbicide resistance” refers to an inherited ability of an individual plant to survive an herbicide application that would kill a normal population of the same species of plant. Herbicide resistance in a plant species often arises due to the application of an herbicide on plants of that species in a specific location. As used herein, the term “herbicide tolerance” refers to the inherent ability of a species of plants to survive and reproduce after herbicide treatment at a normal use rate. Herbicide tolerance is therefore a natural tolerance within the normal population of the plant species, rather than resistance selected for in that species by the application of an herbicide.
  • a “composition” is a mixture comprising at least one herbicide, and also comprising other ingredients used to enhance the properties or effectiveness of the mixture in some way.
  • the other ingredients may include, but are not limited to, diluents, surfactants, adjuvants, anti-foam agents, emulsifiers, colorants, dispersants, antifreeze agents, and other such ingredients.
  • applying an herbicide or herbicidal composition refers to delivering it directly to the targeted vegetation or to the locus thereof or to the area where control of undesirable vegetation is desired.
  • Methods of application include, but are not limited to, pre-emergently contacting soil or water, post-emergently contacting the undesirable vegetation, or contacting the area adjacent to the undesirable vegetation.
  • the term “vegetation” can include, for instance, dormant seeds, germinating seeds, emerging seedlings, plants propagating from vegetative propagules, immature vegetation, and established vegetation.
  • the term "crop" refers to desired vegetation, for instance, plants that are grown to provide food, shelter, pasture, erosion control, etc.
  • Example crops include cereals, legumes, vegetables, orchard and timber trees, grapevines, etc.
  • herbicides or herbicidal compositions have zero or minimal herbicidal effect on crops.
  • undesirable vegetation refers to vegetation that is not wanted in a given area, for instance, weed species.
  • Herbicides or herbicidal compositions are used to control undesirable vegetation. Preferably, herbicides or herbicidal compositions have a large or complete herbicidal effect on undesirable vegetation.
  • acyl refers to formyl, C1-C3 alkylcarbonyl, and C1-C3 haloalkylcarbonyl.
  • C1-C6 acyl refers to formyl, C1-C5 alkylcarbonyl, and C1-C5 haloalkylcarbonyl (the group contains a total of 1 to 6 carbon atoms).
  • alkyl refers to saturated, straight-chained or branched saturated hydrocarbon moieties. Unless otherwise specified, C1-C16 alkyl groups are intended. Examples include methyl, ethyl, propyl, 1-methyl-ethyl, butyl, 1-methyl-propyl, 2-methyl- propyl, 1,1-dimethyl-ethyl, pentyl, 1-methyl-butyl, 2-methyl-butyl, 3-methyl-butyl, 2,2- dimethyl-propyl, 1-ethyl-propyl, hexyl, 1,1-dimethyl-propyl, 1,2-dimethyl-propyl, 1-methyl- pentyl, 2-methyl-pentyl, 3-methyl-pentyl, 4-methyl-pentyl, 1,1-dimethyl-butyl, 1,2-dimethyl- butyl, 1,3-dimethyl-butyl, 2,2-dimethyl-butyl, 2,3-dimethyl-butyl, 2,3-
  • haloalkyl refers to straight-chained or branched alkyl groups, where in these groups the hydrogen atoms may be substituted partially or entirely with halogen atoms. Unless otherwise specified, C1-C16 groups are intended.
  • Examples include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1- chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2- trichloroethyl, pentafluoroethyl, and 1,1,1-trifluoroprop-2-yl.
  • alkenyl refers to unsaturated, straight-chained, or branched hydrocarbon moieties containing a double bond. Unless otherwise specified, C3-C16 alkenyl are intended. Alkenyl groups may contain more than one unsaturated bond.
  • Examples include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl- 1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2- pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1- butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2- methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexen
  • alkynyl represents straight-chained or branched hydrocarbon moieties containing a triple bond. Unless otherwise specified, C3-C16 alkynyl groups are intended. Alkynyl groups may contain more than one unsaturated bond.
  • Examples include C2- C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl (or propargyl), 1-butynyl, 2-butynyl, 3- butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-1- butynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2- propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 3- methyl-1-pentynyl, 4-methyl-1-pentynyl, 1-methyl-2-pentynyl, 4-methyl-2-penty
  • alkoxy refers to a group of the formula R-O-, where R is alkyl as defined above. Unless otherwise specified, alkoxy groups wherein R is a C 1 -C 10 alkyl group are intended. Examples include methoxy, ethoxy, propoxy, 1-methyl-ethoxy, butoxy, 1- methyl-propoxy, 2-methyl-propoxy, 1,1-dimethyl-ethoxy, pentoxy, 1-methyl-butyloxy, 2- methyl-butoxy, 3-methyl-butoxy, 2,2-dimethyl-propoxy, 1-ethyl-propoxy, hexoxy, 1,1- dimethyl-propoxy, 1,2-dimethyl-propoxy, 1-methyl-pentoxy, 2-methyl-pentoxy, 3-methyl- pentoxy, 4-methyl-pentoxy, 1,1-dimethyl-butoxy, 1,2-dimethyl-butoxy, 1,3-dimethyl-butoxy, 2,2-dimethyl-butoxy, 2,3-dimethyl-butoxy, 3,3-
  • haloalkoxy refers to a group of the formula R-O-, where R is haloalkyl as defined above. Unless otherwise specified, haloalkoxy groups wherein R is a C 1 - C 10 alkyl group are intended.
  • Examples include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1- bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2- chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy, pentafluoroethoxy, and 1,1,1-trifluoroprop-2-oxy.
  • alkylthio refers to a group of the formula R-S- where R is alkyl as defined above. Unless otherwise specified, alkylthio groups wherein R is a C 1 -C 10 alkyl group are intended.
  • Examples include methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methyl-propylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1- methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1- ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1- methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1- dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3- dimethylbutylthio, 3,3-dimethylbutyl
  • haloalkylthio refers to an alkylthio group as defined above wherein the carbon atoms are substituted partially or entirely with halogen atoms. Unless otherwise specified, haloalkylthio groups wherein R is a C 1 -C 8 alkyl group are intended.
  • Examples include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1- chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2- dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio, and 1,1,1- trifluoroprop-2-ylthio.
  • aryl refers to a phenyl, indanyl or naphthyl group with phenyl being preferred.
  • heteroaryl refers to a 5- or 6-membered aromatic ring containing one or more heteroatoms, viz., N, O or S; these aromatic and heteroaromatic rings may be fused to other aromatic and/or heteroaromatic systems.
  • the aryl or heteroaryl substituents may be unsubstituted or substituted with one or more substituents selected from halogen, hydroxy, nitro, cyano, formyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1 -C 6 acyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 carbamoyl, hydroxycarbonyl, C 1 -C 6 alkylcarbonyl, aminocarbonyl, C 1 - C 6 alkylaminocarbonyl, C 1 -C 6 dialkylaminocarbonyl, provided that the
  • alkylcarbonyl refers to an alkyl group bonded to a carbonyl group.
  • C1-C3 alkylcarbonyl and C1-C3 haloalkylcarbonyl refer to groups wherein a C1-C3 alkyl group is bonded to a carbonyl group (the group contains a total of 2 to 4 carbon atoms).
  • alkoxycarbonyl refers to a group of the formula wherein R is alkyl.
  • arylalkyl refers to an alkyl group substituted with an aryl group.
  • C 7 -C 10 arylalkyl refers to a group wherein the total number of carbon atoms in the group is 7 to 10.
  • alkylamino refers to an amino group substituted with one or two alkyl groups, which may be the same or different.
  • haloalkylamino refers to an alkylamino group wherein the alkyl carbon atoms are substituted partially or entirely with halogen atoms.
  • C1-C6 alkylaminocarbonyl refers to a group of the formula RNHC(O)- wherein R is C1-C6 alkyl
  • C1-C6 dialkylaminocarbonyl refers to a group of the formula R2NC(O)- wherein each R is independently C1-C6 alkyl.
  • alkylcarbamyl refers to a carbamyl group substituted on the nitrogen with an alkyl group.
  • alkyl-sulfonyl refers to a group of the formula , where R is alkyl.
  • carbamyl (also referred to as carbamoyl and aminocarbonyl) refers to a group of the formula .
  • dialkylphosponyl refers to a group of the formula where R is independently alkyl in each occurrence.
  • C1-C6 trialkylsilyl refers to a group of the formula –SiR3 wherein each R is independently a C1-C6 alkyl group (the group contains a total of 3 to 18 carbon atoms).
  • Me refers to a methyl group
  • OMe refers to a methoxy group
  • i-Pr refers to an isopropyl group.
  • halogen including derivative terms such as halo refers to fluorine, chlorine, bromine and iodine.
  • agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity or that are or can be converted in plants, water, or soil to the referenced herbicide.
  • exemplary agriculturally acceptable esters are those that are or can by hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid which, depending on the pH, may be in the dissociated or undissociated form.
  • active ingredient or “ai” refers to a chemical compound or composition that has an effect on vegetation, for example, a herbicidal effect or a safening effect on the vegetation.
  • acid equivalent or “ae” refers to the amount of the acid form of an active ingredient that is calculated from the amount of a salt or ester form of that active ingredient.
  • Substituted 5-Membered Ring Molecules Disclosed herein are substituted 5-membered ring molecules, such as substituted lactam-molecules or thiolactam-molecules, that may be used as herbicides to control undesirable vegetation in various locations, such as croplands, lawns, pastures, gardens, and recreational areas.
  • the molecules include molecules that are substituted with fluorinated benzyl groups and amino acid groups, and derivatives thereof.
  • the substituted 5-membered ring molecules are molecules of Formula (I): Formula (I) wherein: X is selected from the group consisting of O and S; Y is selected from the group consisting of O, NR 5 , or S; R 1 is selected from the group consisting of H and F; R 2 is selected from the group consisting of methyl and cyclopropyl; R 3 is selected from the group consisting of H, methyl, and methoxy; R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl-heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C
  • the lactam-based molecules are molecules of Formula (II): Formula (II) wherein: R 1 is selected from the group consisting of H and F; R 2 is selected from the group consisting of methyl and cyclopropyl; R 3 is selected from the group consisting of H, methyl, and methoxy; R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl-heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )-hal
  • the lactam-based molecules are molecules of Formula (III) Formula (III) wherein: R 1 is selected from the group consisting of H and F; R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl-heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )-alkyl, (C 1 - C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10
  • the thiolactam-based molecules are molecules of Formula (IV): wherein: X is selected from O or S; R 1 is selected from H or F; R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )-cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl-heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )-alkyl, (C 1 - C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1
  • the substituted 5-membered ring molecules are molecules of Formula (V): Formula (V) wherein R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )- cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl- heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )- alkyl, (C 1 -C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyl-sulfony
  • the substituted 5-membered ring molecules are molecules of Formula (VI): Formula (VI) wherein R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )- cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl- heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )- alkyl, (C 1 -C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyl-sulfony
  • the lactam-based molecules are molecules of Formula (VII): Formula (VII) wherein R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )- cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl- heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )- alkyl, (C 1 -C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyl-sulfonyl
  • the lactam-based molecules are molecules of Formula (VIII): Formula (VIII) wherein R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )- cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl- heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )- alkyl, (C 1 -C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyl-sulfonyl
  • R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )- cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl- heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )- alkyl, (C 1 -C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyl-sulfonyl-(C 1 -C 10 )-alkyl, R 72 R 73
  • R 4 is selected from the group consisting of H, (C 1 -C 16 )-alkyl, (C 3 -C 10 )- cycloalkyl, (C 3 -C 16 )-alkenyl, (C 3 -C 16 )-alkynyl, (C 1 -C 10 )-alkyl-aryl, aryl, (C 1 -C 10 )-alkyl- heteroaryl, heteroaryl, (C 1 -C 10 )-alkyl-cyano, (C 1 -C 16 )-haloalkyl, (C 1 -C 10 )-alkoxy-(C 1 -C 10 )- alkyl, (C 1 -C 10 )-alkylthio-(C 1 -C 10 )-alkyl, (C 1 -C 10 )-alkyl-sulfonyl-(C 1 -C 10 )-alkyl, R 72 R 73 N
  • the substituted 5-membered ring molecules include the molecules given below as Compound A to Compound O.
  • Table 1B Exemplary Substituted 5-Membered Ring Molecules E ⁇
  • the substituted 5-membered ring molecules of the present disclosure exist in specific chiral forms, as shown in the molecular structures shown above. However, the substituted 5-membered ring molecules may also exist in different geometric or optical isomeric forms at other locations within each molecule. It will be appreciated by those skilled in the art, with the benefit of this disclosure, that one stereoisomer may be more active than the other stereoisomers.
  • FIGs.1A – 1C contain exemplary post-emergent data (Tables 5A and 5B) and pre-emergent data (Table 5C) respectively
  • FIG.2 contains Tables 6A and 6B contains comparative pre-emergent isomer, for example, from some of the isomers shown below in Table 2B.
  • Table 2 Exemplary Isomers 3.
  • reaction mixture was stirred at 20 °C for 18 hours (h).
  • the reaction product, Compound A was concentrated onto Celite ® and purified by silica column chromatography.
  • the reaction product was isolated as a slightly yellow sticky oil (89% yield, 97% purity).
  • reaction mixture was stirred at 20 °C for 18 h.
  • the reaction mixture was acidified with 1 normal (N) HCl (4.5 mL).
  • the reaction mixture was diluted with CH 2 Cl 2 (5 mL) and saturated NaCl (20 mL) and extracted with ethyl acetate (50 mL x 3). The combined organic layers were dried with sodium sulfate and concentrated.
  • the reaction product, Compound F was isolated as a white solid (96% yield, 95% purity).
  • Compound G (2-((S)-5-oxo-1-(2,3,5-trifluorobenzyl)pyrrolidin-2-yl)acetyl)-L-valine Compound G Compound G was prepared as follows: In a 20 mL vial charged with a magnetic stir bar were added methyl (2-((S)-5-oxo-1-(2,3,5-trifluorobenzyl)pyrrolidin-2-yl)acetyl)-L- valinate (0.50 g, 1.3 mmol) and sodium hydroxide (0.10 g, 2.5 mmol) in methanol (5.0 mL) under air.
  • reaction mixture was stirred at 20 °C for 18 h.
  • the reaction mixture was acidified with 1 M HCl (7.5 mL), diluted with water (10 mL), and extracted with ethyl acetate (50 mL x 3). The combined organic layers were dried with sodium sulfate and concentrated.
  • the reaction product, Compound H was isolated as a white solid (89% yield, 97% purity).
  • reaction mixture was acidified with 1 M HCl (5.5 mL) and diluted with water (10 mL) and ethyl acetate (20 mL). The aqueous layer of the reaction mixture was extracted with ethyl acetate (30 mL x 4). The combined organic layers were dried with sodium sulfate and concentrated. The reaction product was isolated as a white solid (80% yield, 98% purity).
  • Compound K Methyl O-methyl-N-(2-((S)-5-oxo-1-(2,3,5-trifluorobenzyl)pyrrolidin- 2-yl)acetyl)-L-threoninate
  • Compound K was prepared as follows: In a 45 mL reaction vial charged with a magnetic stir bar were added (S)-2-(5-oxo-1-(2,3,5-trifluorobenzyl)pyrrolidin-2-yl)acetic acid (0.29 g, 1.0 mmol) and methyl O-methyl-L-threoninate hydrochloride (0.18 g, 1.0 mmol) in CH 2 Cl 2 (10 mL).
  • Compound L O-methyl-N-(2-((S)-5-oxo-1-(2,3,5-trifluorobenzyl)pyrrolidin-2- yl)acetyl)-L-threonine
  • Compound L Compound N was prepared as follows: In a 25 mL reaction vial charged with a magnetic stir bar were added lithium hydroxide (0.054 g, 2.3 mmol) and methyl O-methyl-N- (2-((S)-5-oxo-1-(2,3,5-trifluorobenzyl)pyrrolidin-2-yl)acetyl)-L-threoninate (0.19 g, 0.45 mmol) in a THF (1.4 mL)/water (0.45 mL) solvent mixture.
  • reaction was stirred at 20 °C for 18 h.
  • the reaction mixture was acidified with 1 M HCl (2.5 mL), then diluted with water (3 mL) and brine (3 mL).
  • the aqueous layer was extracted with CH2Cl2 (10 mL x 5).
  • the combined organic phase layers were passed through a phase separator and concentrated.
  • the reaction product, Compound N was isolated as a white solid (92% yield, 97% purity).
  • the resulting yellow suspension was stirred at 65 °C for 2 h, and the progress of the reaction was monitored by ultra performance liquid chromatography (UPLC). The mono/bis thiolactam formation in a 4:1 ratio was observed. The reaction mixture was left stirring overnight. After 16 h, 80% of the desired product, Compound M, was observed by liquid chromatography–mass spectrometry (LCMS). The resulting reaction mixture was purified using flash column chromatography with 0%-100% acetone/hexanes and evaporative light scattering detector (ELSD) detection. The major ELSD peak was collected, concentrated, and dried to provide Compound M. The reaction product was isolated as a colorless oil (50% yield, 95% purity).
  • UPLC ultra performance liquid chromatography
  • ELSD evaporative light scattering detector
  • Compound O (2-((S)-1-(2,3-difluorobenzyl)-5-thioxopyrrolidin-2-yl)acetyl)-L-valine
  • Compound O was prepared as follows: In a 25 mL reaction vial charged with a magnetic stir bar was added methyl (2-((S)-1-(2,3-difluorobenzyl)-5-thioxopyrrolidin-2- yl)acetyl)-L-valinate (0.11 g, 0.28 mmol) in a THF (1.1 mL)/water (0.37 mL) solvent mixture.
  • the resulting yellow suspension was stirred at 40 °C for 24 h, and the progress of the reaction was monitored by ultra performance liquid chromatography (UPLC). The mono/bis thiolactam formation in a 1.6:1 ratio was observed.
  • the resulting reaction mixture was purified using flash column chromatography with 0%-100% acetone/hexanes and evaporative light scattering detector (ELSD) detection. The major ELSD peak was collected, concentrated, and dried to provide Compound P.
  • the reaction product was isolated as a colorless oil (28% yield, 95% purity).
  • reaction mixture was left stirring for 48 h.
  • the resulting reaction mixture was purified by flash column chromatography with 0%-100% acetone/hexanes and ELSD detection. The major ELSD peak was collected, concentrated, and dried to provide Compound Q.
  • the reaction product was isolated as a colorless oil (65% yield, 90% purity).
  • compositions containing the substituted 5- membered ring molecule herbicides disclosed herein are a mixture comprising at least one substituted 5-membered ring molecule herbicide or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof) and further comprising other additives used to enhance the properties or effectiveness of the mixture in some way.
  • Exemplary additives include but are not limited to adjuvants, safeners, carriers, and combinations thereof.
  • Compositions may be in various physical states, including but not limited to as solutions, emulsions, suspensions, granules, powders, and other such states. 1.
  • Adjuvants In some aspects, the additive includes an agriculturally acceptable adjuvant.
  • Exemplary agriculturally acceptable adjuvants include, but are not limited to, antifreeze agents, antifoam agents, compatibilizing agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, colorants, odorants, penetration aids, wetting agents, spreading agents, dispersing agents, thickening agents, freeze point depressants, antimicrobial agents, crop oil, adhesives (for instance, for use in seed formulations), surfactants, protective colloids, emulsifiers, tackifiers, and mixtures thereof.
  • Exemplary agriculturally acceptable adjuvants include, but are not limited to, crop oil concentrates (e.g., 85% mineral oil + 15% emulsifiers); nonylphenol ethoxylates; benzylcocoalkyldimethyl quaternary ammonium salts; blends of petroleum hydrocarbon, alkyl esters, organic acids, and anionic surfactants; C 9 -C 11 alkylpolyglycoside; phosphate alcohol ethoxylates; natural primary alcohol (C 12 -C 16 ) ethoxylate; di-sec-butylphenol EO-PO block copolymers; polysiloxane-methyl cap; nonylphenol ethoxylate+urea ammonium nitrates; emulsified methylated seed oils; tridecyl alcohol (synthetic) ethoxylates (e.g., 8 EO); tallow amine ethoxylates (e.g., 15 EO); and PEG(
  • Exemplary surfactants include, but are not limited to: the alkali metal salts, alkaline earth metal salts and ammonium salts of fatty acids or of aromatic sulfonic acids (e.g., lignosulfonic acids, phenolsulfonic acids, naphthalenesulfonic acids, and dibutylnaphthalenesulfonic acid); alkyl- and alkylarylsulfonates; alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates; salts of sulfated hexa-, hepta- and octadecanols; salts of fatty alcohol glycol ethers; condensates of sulfonated naphthalene and its derivatives with formaldehyde; condensates of naphthalene or of the n
  • Exemplary thickeners include, but are not limited to, polysaccharides (e.g., xanthan gum), organic and inorganic sheet minerals, and mixtures thereof.
  • Exemplary antifoam agents include, but are not limited to, silicone emulsions, long- chain alcohols, fatty acids, fatty acid salts, organofluorine compounds, and mixtures thereof.
  • Exemplary antimicrobial agents include, but are not limited to, bactericides based on dichlorophen and benzyl alcohol hemiformal; isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones; and mixtures thereof.
  • Exemplary antifreeze agents include, but are not limited to ethylene glycol, propylene glycol, urea, glycerol, and mixtures thereof.
  • Exemplary colorants include, but are not limited to, the dyes known under the names Rhodamine B, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108, and mixtures thereof.
  • Exemplary adhesives include, but are not limited to, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, tylose, and mixtures thereof.
  • the additive is a safener. Safeners are compounds leading to better crop plant compatibility when applied with a herbicide. In some aspects, the safener itself is herbicidally active. In some aspects, the safener acts as an antidote or antagonist in the crop plants and can protect the crop plants from damage that might otherwise occur from an applied herbicide.
  • Exemplary safeners include, but are not limited to, AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet, cloquintocet-mexyl, cyometrinil, cyprosulfamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, disulfoton, fenchlorazole, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen- ethyl, jiecaowan, jiecaoxi, mefenpyr, mefenpyr-diethyl, mephenate, naphthalic anhydride, 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine, 4-(dichloroacetyl)-1-oxa-4-azas
  • the safener can be cloquintocet or an ester or salt thereof, such as cloquintocet-mexyl.
  • the safener can be mefenpyr or an ester or salt thereof, such as mefenpyr-diethyl.
  • the safener is employed in rice, cereal, or maize.
  • mefenpyr or cloquintocet can be used to antagonize harmful effects of the compositions on rice, row crops, and cereals. 3.
  • the additive includes a carrier.
  • the additive includes a liquid or solid carrier.
  • the additive includes an organic or inorganic carrier.
  • Exemplary liquid carriers include, but are not limited to: water; petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like; toluene; x
  • Exemplary solid carriers include, but are not limited to: silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, pyrophyllite clay, attapulgus clay, kieselguhr, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, and mixtures thereof.
  • compositions comprising the substituted 5-membered ring molecule herbicide may be present in suspended, emulsified, dissolved, or solid form.
  • exemplary compositions include, but are not limited to, aqueous solutions, aqueous suspensions, aqueous dispersions, aqueous emulsions, aqueous microemulsions, aqueous suspo-emulsions, oil solutions, oil suspensions, oil dispersions, oil emulsions, oil microemulsions, oil suspo-emulsions, self-emulsifying formulations, gels, pastes, powders, dusts, granules, and materials for spreading.
  • the substituted 5-membered ring molecule herbicide is in an aqueous solution that can be diluted before use.
  • the substituted 5-membered ring molecule herbicide may be provided as a high-strength formulation such as a concentrate.
  • the concentrate is stable and retains potency during storage and shipping.
  • the concentrate is a clear, homogeneous liquid that is stable at temperatures of 54 °C or greater.
  • the concentrate does not exhibit any precipitation of solids at temperatures of 10 °C or higher.
  • the concentrate does not exhibit separation, precipitation, or crystallization of any components at low temperatures.
  • the concentrate remains a clear solution at temperatures below 0 °C (e.g., below -5 °C, below -10 °C, below -15 °C).
  • the concentrate exhibits a viscosity of less than 50 centipoise (50 megapascals), even at temperatures as low as 5 °C.
  • the concentrate does not exhibit separation, precipitation, or crystallization of any components during storage for a period of 2 weeks or greater (e.g., 4 weeks, 6 weeks, 8 weeks, 3 months, 6 months, 9 months, or 12 months or greater).
  • emulsions, gels, pastes, or oil dispersions can be prepared by homogenizing the substituted 5-membered ring molecule herbicide in water with a wetting agent, tackifier, dispersant, or emulsifier.
  • concentrates suitable for dilution with water can be prepared, comprising the substituted 5-membered ring molecule herbicide, a wetting agent, a tackifier, and a dispersant or emulsifier.
  • powders, materials for spreading, or dusts can be prepared by mixing or concomitant grinding the substituted 5-membered ring molecule herbicide and optionally other additives with a solid carrier.
  • granules e.g., coated granules, impregnated granules and homogeneous granules
  • granules can be prepared by binding the substituted 5-membered ring molecule herbicide to solid carriers.
  • the compositions comprise, by total weight of the composition, from about 0.01% to about 99% of the substituted 5-membered ring molecule herbicide, including about 0.025%, 0.05%, 0.075%, 0.1%, 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 7.5%, 8%, 9%, 10%, 12.5%, 15%, 17.5%, 20%, 22.5%, 25%, 27.5%, 30%, 32.5%, 35%, 37.5%, 40%, 42.5%, 45%, 47.5%, 50%, 52.5%, 55%, 57.5%, 60%, 62.5%, 65%, 67.5%, 70%, 72.5%, 75%, 77.5%, 80%, 82.5%, 85%, 87.5%, 90%, 92.5%, 95%, 97.5%, or 98% of the substituted 5-membered ring molecule herbicide by total weight of the substituted 5-
  • Concentrates can be diluted with an inert carrier, such as water, prior to application.
  • the diluted compositions applied to undesirable vegetation or the locus of undesirable vegetation can contain from 0.0006 to 8.0 weight percent (wt %) of the total amount of the substituted 5- membered ring molecule herbicide (e.g., from 0.001 to 5.0 wt %), based on the total weight of the diluted composition. 5.
  • the substituted 5-membered ring molecules or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof) disclosed herein can be formulated into compositions and applied in any known technique for applying herbicides.
  • Exemplary application techniques include, but are not limited to, spraying, atomizing, dusting, sprinkling, spreading, or direct application.
  • the method of application can vary depending on the intended purpose. In some aspects, the method of application can be chosen to ensure the finest possible distribution of the compositions disclosed herein.
  • a method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation any of the compositions is disclosed herein.
  • the compositions containing a substituted 5-membered ring molecule disclosed herein can be applied pre-emergence (before the emergence of undesirable vegetation) or post- emergence (e.g., during and/or after emergence of the undesirable vegetation).
  • the composition is applied postemergence to the undesirable vegetation.
  • the compositions can be applied after seeding and before or after the emergence of the crop plants.
  • the compositions disclosed herein show good crop tolerance even when the crop has already emerged and can be applied during or after the emergence of the crop plants.
  • the compositions when used in crops, can be applied before seeding of the crop plants.
  • the compositions disclosed herein are applied to vegetation or an area adjacent the vegetation or applying to soil or water to prevent the emergence or growth of vegetation by spraying (e.g., foliar spraying).
  • the spraying techniques use, for example, water as carrier and spray volume rates of from 2 liters per hectare (L/ha) to 2000 L/ha (e.g., from 10–1000 L/ha or from 50–500 L/ha).
  • the compositions disclosed herein are applied by the low-volume or the ultra-low-volume method, wherein the application is in the form of micro granules.
  • the compositions disclosed herein are less well tolerated by certain crop plants, the compositions can be applied with the aid of the spray apparatus in such a way that they come into little contact, if any, with the leaves of the sensitive crop plants while reaching the leaves of undesirable vegetation that grows underneath or on the bare soil (e.g., post-directed or lay-by).
  • compositions disclosed herein can be applied as dry compositions (e.g., granules, powders, or dusts).
  • the compositions disclosed herein are applied by foliar application.
  • herbicidal activity is exhibited by the compounds of the mixture when they are applied directly to the plant or to the locus of the plant at any stage of growth or before planting or emergence.
  • the effect observed can depend upon the type of undesirable vegetation to be controlled, the stage of growth of the undesirable vegetation, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. In some aspects, these and other factors can be adjusted to promote non-selective or selective herbicidal action.
  • the compositions and methods disclosed herein can be used to control undesirable vegetation in a variety of applications.
  • compositions and methods disclosed herein can be used for controlling undesirable vegetation in areas including, but not limited to, farmland, turfgrass, pastures, grasslands, rangelands, fallow land, rights-of-way, aquatic settings, tree and vine, wildlife management areas, or rangeland.
  • the undesirable vegetation is controlled in a row crop.
  • Exemplary crops include, but are not limited to, wheat, barley, triticale, rye, teff, oats, maize, cotton, soy, canola, pulses, sunflower, sugar beet, sorghum, rice, millet, sugarcane, and range land (e.g., pasture grasses).
  • compositions and methods disclosed herein can be used for controlling undesirable vegetation in maize, soy, canola, cotton, pulses, sunflower, sugar beet, wheat, barley, rice, sorghum, millet, oats, or combinations thereof.
  • the compositions and methods disclosed herein can be used in industrial vegetation management (IVM) or for utility, pipeline, roadside, and railroad rights ⁇ of ⁇ way applications.
  • the compositions and methods disclosed herein can also be used in forestry (e.g., for site preparation or for combating undesirable vegetation in plantation forests).
  • the compositions and methods disclosed herein can be used to control undesirable vegetation in conservation reserve program lands (CRP), trees, vines, grasslands, and grasses grown for seeds.
  • CRP conservation reserve program lands
  • compositions and methods disclosed herein can be used on lawns (e.g., residential, industrial, and institutional), golf courses, parks, cemeteries, athletic fields, and sod farms.
  • the compositions and methods disclosed herein can also be used in crop plants that are resistant to, for instance, herbicides, insecticides, fungicides, pathogens, insects, or combinations thereof.
  • the compositions and methods disclosed herein can be used in crop plants that are resistant to one or more herbicides because of genetic engineering or breeding.
  • the compositions and methods disclosed herein can be used in crop plants that are resistant to one or more pathogens such as plant pathogenic fungi owing to genetic engineering or breeding.
  • compositions and methods disclosed herein can be used in crop plants that are resistant to attack by insects owing to genetic engineering or breeding.
  • exemplary resistant crops include, but are not limited to, crops that are resistant to photosystem II inhibitors, or crop plants that, owing to introduction of the gene for Bacillus thuringiensis (or Bt) toxin by genetic modification, are resistant to attack by certain insects.
  • compositions and methods described herein can be used in conjunction with glyphosate, glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins, aryloxyphenoxypropionates, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, acetolactate synthase (ALS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, protoporphyrinogen oxidase (PROTOX) inhibitors, triazines, and bromoxynil to control vegetation in crops tolerant to glyphosate, glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins, aryloxyphenoxypropionates, ACCase inhibitors, imidazolinones, synthetic auxin herbicides, HPPD inhibitors, PROTOX inhibitors, triazines, brom
  • the undesirable vegetation is controlled in glyphosate, glufosinate, dicamba, phenoxy auxins, pyridyloxy auxins, aryloxyphenoxypropionates, ACCase inhibitors, synthetic auxin herbicide, HPPD inhibitors, PROTOX inhibitors, triazines, and bromoxynil tolerant crops possessing single, multiple or stacked traits conferring tolerance to single or multiple chemistries and/or multiple modes of action.
  • the undesirable vegetation can be controlled in a crop that is ACCase-tolerant, ALStolerant, or a combination thereof.
  • compositions described herein and other complementary herbicides are applied at the same time, either as a combination composition or as a tank mix, or as sequential applications.
  • the compositions and methods may be used in controlling undesirable vegetation in crops possessing agronomic stress tolerance (including but not limited to drought, cold, heat, salt, water, nutrient, fertility, pH), pest tolerance (including but not limited to insects, fungi, and pathogens), and crop improvement traits (including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture).
  • agronomic stress tolerance including but not limited to drought, cold, heat, salt, water, nutrient, fertility, pH
  • pest tolerance including but not limited to insects, fungi, and pathogens
  • crop improvement traits including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture.
  • the compounds and compositions described herein may be used to control plant species described, but not limited
  • compositions disclosed herein can be used for controlling undesirable vegetation including grasses, broadleaf weeds, sedge weeds, and combinations thereof.
  • compositions disclosed herein can be used for controlling undesirable vegetation including, but not limited to, Acanthospermum species, Aegilops species, Agrostis species, Alopecurus species, Ambrosia species, Anthemis species, Apera species, Amaranthus species, Avena species, Brachiaria species, Bromus species, Chenopodium species, Cenchrus species, Cirsium species, Commelina species, Cyperus species, Datura species, Digitaria species, Echinochloa species, Eleusine species, Atriplex species, Brassica species, Convolvulus species, Conyza species, Cassia species, Euphorbia species, Geranium species, Galinsoga species, Ipomea species, Lamium species, Leptochloa species, Lol
  • the undesired vegetation includes blackgrass (Alopecurus myosuroides Huds.), wild oat (Avena fatua), barnyard grass (Echinochloa crus-galli) common chickweed (Stellaria media), velvetleaf (Abutilon theophrasti), hemp sesbania (Sesbania exaltata Cory), Anoda cristata, Bidens pilosa, Brassica kaber, shepherd’s purse (Capsella bursa-pastoris), cornflower (Centaurea cyanus or Cyanus segetum), hempnettle (Galeopsis tetrahit), cleavers (Galium aparine), common sunflower (Helianthus annuus), Desmodium tortuosum, Italian ryegrass (Lolium multiflorum), kochia (Kochia scoparia), Medicago arabica, Mercurialis annua, Myosotis arvensis, common poppy (Pap
  • compositions described herein can be used to control herbicide resistant or tolerant weeds.
  • the methods employing the compositions described herein may also be employed to control herbicide resistant or tolerant weeds.
  • Exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxy
  • Exemplary resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes, biotypes with resistance or tolerance to multiple herbicide modes of action, and biotypes with multiple resistance or tolerance mechanisms (e.g., target site resistance or metabolic resistance).
  • biotypes with resistance or tolerance to multiple herbicides include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes, biotypes with resistance or tolerance to multiple herbicide modes of action, and biotypes with multiple resistance or tolerance mechanisms (e.g., target site resistance or metabolic resistance).
  • examples of some aspects of the present disclosure are given below. Parts and percentages are on a per weight basis unless otherwise indicated. Examples The details of the compositions and the crops tested are specified in the following Examples. EVALUATION OF PESTICIDAL ACTIVITY
  • the compounds disclosed herein exhibit varying pesticidal activity.
  • the pesticidal activity may include
  • Tables 5A-5C are select post-emergent and pre-emergent herbicidal activity for some compounds on various weeds and crops.
  • Table 3 lists the plants being evaluated with the various substituted 5-membered ring pesticides at the time of application for the results exemplified in Table 5A and 5B, shown in FIGs.1A and 1B respectively, and the pre-emergent control exemplified in Table 5C in FIG.1C.
  • Tables 6A- 22B which include mixture data of the substituted 5-membered rings with other herbicides and/or safeners and mixture data. Also included in FIGs. 18A-18B are some of the disclosed additional substituted 5-membered rings (shown below in Table 4) and other herbicides. Table 1: Plant Species Used in Evaluations
  • METHOD 1 POSTEMERGENCE APPLICATION METHODS FOR HERBICIDE EVALUATIONS Seeds of the desired test plant species were planted in plastic pot with 64 square centimeter (cm 2 ) surface area filled with soil-less media planting mix containing PRO-MIX ® BX (Premier Tech Horticulture, Quakertown, PA, USA) and PROFILE ® GREENS GRADETM (Profile Products LLC, Buffalo Grove, IL, USA) at pH of 5.2 to 6.2 and a minimum of 50% organic matter content.
  • PRO-MIX ® BX Premier Tech Horticulture, Quakertown, PA, USA
  • PROFILE ® GREENS GRADETM Profile Products LLC, Buffalo Grove, IL, USA
  • Echinochloa crus-galli barnyard grass
  • Setaria faberi giant foxtail
  • Alopecurus myosuroides blackgrass
  • Avena fatua wild oat
  • Ipomea hederacea ivyleaf morningglory
  • Helianthus annuus unsunflower
  • Plants were sub-irrigated as needed with water containing Jack’s Professional 15-5- 154 Ca 2Mg fertilizer. Compositions of each exemplified molecule were dissolved in 2.75 mL of formulation solvent containing by volume (59% deionized water, 24% acetone, 15% isopropanol, 0.75% DMSO, 1.5% crop oil concentrate, 0.02% Tergitol 15S-7) to deliver a spray rate of 2000 or 4000 grams of active ingredient per hectare (g ai/h). Samples were vortexed and sonicated if needed to dissolve the compound into solution.
  • Formulated compounds were applied to all six species in 3 pots using a DeVilbiss® compressed air sprayer at 2–4 pounds per square inch (psi), allowed to dry then returned to the greenhouse. After 9-11 days, the condition of the test plants was compared with that of the control plants by visual assessment and evaluated based on a scoring scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete plant death. Visual assessments of plant injury were made based on growth inhibition, growth reduction, discoloration, leaf deformity and necrosis.
  • METHOD 2 PRE-EMERGENCE APPLICATION METHODS FOR HERBICIDE EVALUATIONS Seeds of the desired test plant species were planted into 12.7 cm diameter round plastic pots containing a silt loam mineral soil. Compositions of each exemplified molecule were dissolved in 0.67 mL 97:3 v/v mixture of acetone and DMSO, then further diluted with 2.05 mL of solvent containing 78% D.I. H2O, 20% isopropanol, 2% AgriDex crop oil concentrate and 0.02% Tergitol 15S-7 surfactant. Samples were mixed vigorously (vortexed) and sonicated if needed to bring the compound into solution.
  • Solution was mixed with 15 mL of D.I. H2O and poured evenly over the soil containing potted seeds. The vial was rinsed with an additional 15 mL of D.I. H2O which was again poured over the soil.
  • Treated pots are moved to in a greenhouse with an approximate 16-hour (h) photoperiod and maintained at 23 °C during the day and 22 °C during the night. Pots were kept moist through over-the-top irrigation. After 14 days, the condition of the test plants was compared with that of the control plants by visual assessment and evaluated based on a scoring scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to no emergence or complete plant death after emergence.
  • METHOD 3 POSTEMERGENCE APPLICATION METHODS FOR HERBICIDE EVALUATIONS Seeds of the desired test plant species were planted in plastic pot with 64 square centimeter (cm 2 ) surface area filled with soil-less media planting mix containing PRO-MIX ® BX (Premier Tech Horticulture, Quakertown, PA, USA) and PROFILE ® GREENS GRADETM (Profile Products LLC, Buffalo Grove, IL, USA) at pH of 5.2 to 6.2 and a minimum of 50% organic matter content.
  • PRO-MIX ® BX Premier Tech Horticulture, Quakertown, PA, USA
  • PROFILE ® GREENS GRADETM Profile Products LLC, Buffalo Grove, IL, USA
  • a fungicide treatment and/or other chemical or physical treatment was applied.
  • the plants were grown for 7–36 days (d) in a greenhouse with an approximate 16-hour (h) photoperiod and set to 23 °C day and 22 °C night temperature regimen. Plants were sub- irrigated as needed with water containing Jack’s Professional 15-5-15 4 Ca 2Mg fertilizer. Supplemental lighting was provided as necessary. The plants were employed for testing when they reached the second or third true leaf stage.
  • compositions of each exemplified molecule was weighed to a known amount, determined by the highest rate to be tested, by placing in a 25 mL glass vial and was dissolved in 4 mL of a 97:3 v/v mixture of acetone and DMSO to obtain concentrated stock solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated.
  • the concentrated stock solutions obtained were diluted with 20 mL of an aqueous mixture containing acetone, water, isopropyl alcohol, DMSO, AgriDex crop oil concentrate, and Tergitol 15S-7 surfactant in a 48.5:39:10:1.5:1.0:0.02 v/v ratio to obtain spray solutions at the application rate.
  • Compound requirements are based upon a 12 mL application volume at a rate of 187 liters per hectare (L/ha).
  • the spray solutions were applied to the plant material with an overhead DeVries track sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m 2 ) at a spray height of 18 inches (43 centimeters (cm)) above the average plant canopy.
  • Control or non-treated plants were sprayed in the same manner with the solvent blank or not treated. All herbicide application rates are given as grams acid equivalent per hectare (g ae/h) or grams active ingredient per hectare (g ai/h).
  • the treated plants and control plants were placed in a greenhouse as described above and watered by subirrigation to prevent removal of the test compound. After 13-15 days, the condition of the test plants was compared with that of the control plants by visual assessment and evaluated based on a scoring scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete plant death. Visual assessments of plant injury were made based on growth reduction, discoloration, leaf deformity and necrosis.
  • METHOD 4 POSTEMERGENCE APPLICATION METHODS FOR HERBICIDE EVALUATIONS Seeds of the desired test plant species were planted in plastic pot with 64 square centimeter (cm 2 ) surface area filled with soil-less media planting mix containing PRO-MIX ® BX (Premier Tech Horticulture, Quakertown, PA, USA) and PROFILE ® GREENS GRADETM (Profile Products LLC, Buffalo Grove, IL, USA) at pH of 5.2 to 6.2 and a minimum of 50% organic matter content.
  • a fungicide treatment and/or other chemical or physical treatment was applied to help ensure good germination and healthy plants.
  • plants Prior to treatment, plants were grown in a chamber for 4-13 days (days) with a 16-hour (h) photoperiod and set to 25 °C or 28 °C day or 22 °C or 24 °C night temperature regimen dependent on species. Plants were delivered to a greenhouse with an approximate 14-hour (h) photoperiod and set to 27 °C day and 24 °C night temperature regimen for the duration of the experiment. Plants were sub-irrigated as needed with water containing Jack’s Professional 15- 5-154 Ca 2Mg fertilizer. Supplemental lighting was provided as necessary. The plants were employed for testing when they reached the second or third true leaf stage.
  • Emulsifiable concentrates of 5-membered ring molecules were prepared at 100 grams active ingredient per liter (g ai/L). An aliquot of each emulsifiable concentrate was placed in a 25 mL glass vial and diluted with an aqueous mixture of 1.0% (v/v) Dyne-Amic ® (Helena ® ) to obtain spray solutions based upon a 12 mL application volume at a rate of 187 liters per hectare (L/ha). Spray solutions of the herbicide combinations (Compound A or Compound B) plus a second herbicide were prepared by adding weighed amounts or aliquots of the second herbicide to the spray solutions of Compound A or Compound B to form 12-mL spray solutions in two-way combinations.
  • the spray solutions were applied to the plant material with an overhead DeVries track sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m 2 ) at a spray height of 18 inches (43 centimeters (cm)) above the average plant canopy.
  • Control or non-treated plants were sprayed in the same manner with the solvent blank or not treated. All herbicide application rates are given as grams acid equivalent per hectare (g ae/h) or grams active ingredient per hectare (g ai/h).
  • the treated plants and control plants were placed in a greenhouse as described above and watered by subirrigation to prevent removal of the test compound.
  • test plants After 13-15 days, the condition of the test plants was compared with that of the control plants by visual assessment and evaluated based on a scoring scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete plant death. Visual assessments of plant injury were made based on growth reduction, discoloration, leaf deformity and necrosis.
  • METHOD 5 POSTEMERGENCE APPLICATION METHODS FOR HERBICIDE EVALUATIONS Seeds of the desired test plant species were planted in plastic pot with 103.2 square centimeter (cm 2 ) surface area filled with soil-less media planting mix containing PRO-MIX ® BX (Premier Tech Horticulture, Quakertown, PA, USA) and PROFILE ® GREENS GRADETM (Profile Products LLC, Buffalo Grove, IL, USA) at pH of 5.2 to 6.2 and a minimum of 50% organic matter content.
  • a fungicide treatment and/or other chemical or physical treatment was applied to help ensure good germination and healthy plants.
  • plants Prior to treatment, plants were grown in a chamber for 5-13 days (days) with a 16-hour (h) photoperiod and set to 24 °C or 28 °C day or 23 °C or 24 °C night temperature regimen dependent on species. Plants were delivered to a greenhouse with an approximate 14-hour (h) photoperiod and set to 28 °C day and 25 °C night temperature regimen for the duration of the experiment. Plants were sub-irrigated as needed with water containing Jack’s Professional 15- 5-154 Ca 2Mg fertilizer. Supplemental lighting was provided as necessary. The plants were employed for testing when they reached the second or third true leaf stage.
  • Emulsifiable concentrates of 5-membered ring molecule were prepared at 100 grams active ingredient per liter (g ai/L). An aliquot of each emulsifiable concentrate was placed in a 25 mL glass vial and diluted with an aqueous mixture of 1.0% (v/v) Dyne-Amic ® (Helena ® ) to obtain spray solutions based upon a 12 mL application volume at a rate of 187 liters per hectare (L/ha).
  • Spray solutions of the herbicide combinations (Compound A or Compound B) plus a second herbicide were prepared by adding weighed amounts or aliquots of the second herbicide to the spray solutions of Compound A or Compound B to form 12-mL spray solutions in two-way combinations.
  • the spray solutions were applied to the plant material with an overhead DeVries track sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m 2 ) at a spray height of 18 inches (43 centimeters (cm)) above the average plant canopy. Control or non-treated plants were sprayed in the same manner with the solvent blank or not treated.
  • METHOD 6 POSTEMERGENCE APPLICATION METHODS FOR HERBICIDE EVALUATIONS Seeds of the desired test plant species were planted in plastic pot with 103.2 square centimeter (cm 2 ) surface area filled with soil-less media planting mix containing PRO-MIX ® BX (Premier Tech Horticulture, Quakertown, PA, USA) and PROFILE® GREENS GRADETM (Profile Products LLC, Buffalo Grove, IL, USA) at pH of 5.2 to 6.2 and a minimum of 50% organic matter content.
  • a fungicide treatment and/or other chemical or physical treatment was applied to help ensure good germination and healthy plants.
  • plants Prior to treatment, plants were grown in a chamber for 5-13 days (days) with a 16-hour (h) photoperiod and set to 24 °C or 28 °C day or 23 °C or 24 °C night temperature regimen dependent on species. Plants were delivered to a greenhouse with an approximate 14-hour (h) photoperiod and set to 28 °C day and 25 °C night temperature regimen for the duration of the experiment. Plants were sub-irrigated as needed with water containing Jack’s Professional 15- 5-154 Ca 2Mg fertilizer. Supplemental lighting was provided as necessary. The plants were employed for testing when they reached the second or third true leaf stage.
  • compositions of each the 5-membered ring molecule being evaluated was weighed to a known amount, determined by the highest rate to be tested, by placing in a 25 mL glass vial and was dissolved in 4 mL of a 97:3 v/v mixture of acetone and DMSO to obtain concentrated stock solutions. If the compound did not dissolve readily, the mixture was warmed and/or sonicated.
  • the concentrated stock solutions obtained were diluted with 20 mL of an aqueous mixture containing acetone, water, isopropyl alcohol, DMSO, AgriDex crop oil concentrate, and Tergitol 15S-7 surfactant in a 56.2:32.5:8.3:1.75:1.25:0.02 v/v ratio to obtain spray solutions at the application rate.
  • Spray solutions of the 5-membered ring molecule being evaluated were combined with a second herbicide by adding weighed amounts or aliquots of the second herbicide to the spray solutions of the 5-membered ring molecule being evaluated to form 12-mL spray solutions in two-way combinations.
  • the spray solutions were applied to the plant material with an overhead DeVries track sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m 2 ) at a spray height of 18 inches (43 centimeters (cm)) above the average plant canopy.
  • Control or non-treated plants were sprayed in the same manner with the solvent blank or not treated. All herbicide application rates are given as grams acid equivalent per hectare (g ae/h) or grams active ingredient per hectare (g ai/h).
  • the treated plants and control plants were returned to a greenhouse as described above and watered by subirrigation to prevent removal of the test compound.
  • compositions comprising compounds according to Formula I be mixed with or applied in combination with another compound, such as another pesticide, additive, or combination thereof.
  • disclosed compositions may comprise (a) a compound according to Formula I and (b) another herbicide.
  • disclosed compositions may comprise (a) a compound according to Formula I, (b) another herbicide, and (c) another safener.
  • compositions that can comprise other substituted 5- membered rings selected from the following compounds (PYR-1 through PYR-21 and including all stereoisomers thereof) below and mixed with or applied in combination with another compound, such as another pesticide, additive, or combination thereof.
  • Additional substituted 5-membered rings include the following compounds: TABLE 4: ADDITIONAL SUBSTITUTED 5-MEMBERED RINGS (JAS)
  • compositions may comprise (a) one of the aforementioned additional substituted 5-membered ring herbicides and (b) another herbicide in ratios surprisingly discovered.
  • compositions may comprise (a) one of the aforementioned additional substituted 5-membered ring herbicides, (b) another herbicide, and (c) another safener in ratios also discovered.
  • PYR-3 Methyl (S)-2-(1-(2,3-difluorobenzyl)-5-oxopyrrolidin-2-yl)acetate
  • PYR-3 PYR-3 was prepared as follows: In a 250 mL round-bottomed flask charged with magnetic stir bar was added methyl (S)-2-(5-oxopyrrolidin-2-yl)acetate (3.1 g, 20 mmol) in THF (100 mL) under N 2 . Lithium bis(trimethylsilyl)amide solution (1M in THF, 20 mL, 20 mmol) added at 0 °C and kept at this temperature for 15 min.
  • PYR-4 (S)-2-(1-(2,3-difluorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid
  • PYR-4 PYR-4 was prepared as follows: In a 100 mL round-bottomed flask charged with magnetic stir bar was added methyl (S)-2-(1-(2,3-difluorobenzyl)-5-oxopyrrolidin-2- yl)acetate (5.3 g, 19 mmol) and lithium hydroxide (2.2 g, 93 mmol) in a THF (27 mL)/water (9.3 mL) solvent mixture. The reaction was stirred at 20 °C for 18 hr.
  • PYR-5 Methyl (S)-2-(1-(2,3,5-trifluorobenzyl)-5-oxopyrrolidin-2-yl)acetate
  • PYR-5 PYR-5 was prepared as follows: In a 250 mL round-bottomed flask charged with magnetic stir bar was added methyl (S)-2-(5-oxopyrrolidin-2-yl)acetate (1.6 g, 10 mmol) in THF (50 mL) under N2.
  • PYR-6 (S)-2-(1-(2,3,5-trifluorobenzyl)-5-oxopyrrolidin-2-yl)acetic acid
  • PYR-6 was prepared as follows: In a 500 mL round-bottomed flask charged with magnetic stir bar was added methyl (S)-2-(5-oxo-1-(2,3,5-trifluorobenzyl)pyrrolidin-2- yl)acetate (13 g, 43 mmol) and sodium hydroxide (23 mL, 47 mmol) solution in THF (200 mL). The reaction was stirred at 20 °C for 20 hr.
  • a safened composition comprising compounds according to Formula I may be mixed with or applied in combination with (b) a safener, such as an azole carboxylate safener or an agriculturally acceptable salt or ester thereof.
  • a safener such as an azole carboxylate safener or an agriculturally acceptable salt or ester thereof.
  • safened compositions comprising the aforementioned PYR-1 through PYR- 16 (AND ALL STEREOISOMERS THEREOF) compounds may be mixed in combination with (b) a safener.
  • (a) and (b) are used in an amount sufficient to induce an enhanced herbicidal effect (e.g., increased damage or injury to undesirable vegetation) while still showing good crop compatibility (e.g., no increased damage to crops or minimal increased damage or injury to crops) when compared to the individual application of the herbicidal compounds (a) or (b).
  • the damage or injury to undesirable vegetation caused by the safened compositions and methods disclosed herein is evaluated using a scale from 0% to 100%, when compared with the untreated control vegetation, wherein 0% indicates no damage to the undesirable vegetation and 100% indicates complete destruction of the undesirable vegetation.
  • the damage or injury to the crop caused by the safened compositions and methods disclosed herein is evaluated using a scale from 0% to 100%, when compared with control crops treated with only the herbicide or the safener, wherein 0% indicates no damage to the crop and 100% indicates complete destruction of the crop.
  • the joint action of (a) the compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof) and (b) the azole carboxylate safener or an agriculturally acceptable salt or ester thereof results in enhanced herbicidal effect against undesirable vegetation, even at application rates below those typically used for the herbicide to have a herbicidal effect on its own.
  • compositions and methods disclosed herein can, based on the individual components, be used at lower application rates to achieve a herbicidal effect comparable to the effect produced by the individual components at normal application rates.
  • the joint action of (a) the compounds according to Formula I and (b) the azole carboxylate safener or an agriculturally acceptable salt or ester thereof results in protective effect for desired crops against damage to the crops that might be caused by the herbicide alone.
  • the weight ratio of (a) the compounds according to Formula I (in g ae/ha) or (a) the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), to (b) the azole carboxylate safener or an agriculturally acceptable salt or ester thereof (in g ai/ha) can be 1:5 or more, such as 1:4.75 or more, 1:4.5 or more, 1:4.25 or more, 1:4 or more, 1:3.75 or more, 1:3.5 or more, 1:3.25 or more, 1:3 or more, 1:2.75 or more, 1:2.5 or more, 1:2.25 or more, 1:2 or more, 1:1.9 or more, 1:1.8 or more, 1:1.7 or more, 1:1.6 or more, 1:1.5 or more, 1:1.4 or more, 1:1.3 or more, 1:1.2 or more, 1:1.1 or more, 1:1 or more, 1.1:1 or more, 1.2:1 or more, 1.3:1 or more, 1.4:1 or more, 1.5
  • compositions and methods of the present disclosure can include an azole carboxylate safener or an agriculturally acceptable salt or ester thereof.
  • Herbicide safeners are molecules used in combination with herbicides to make them “safer” – that is, to reduce the herbicidal effect of the herbicide on crop plants and to improve selectivity between crops and the undesirable vegetation being targeted by the herbicide.
  • Herbicide safeners can be used to pre-treat crop seeds prior to planting. Herbicide safeners may also be sprayed on plants as a mixture with the herbicide, or separately and sequentially with the herbicide.
  • Azoles are a class of five-membered nitrogen heterocyclic ring compounds containing at least one additional heteroatom (e.g., nitrogen, sulfur, or oxygen) within the heterocyclic ring. Examples of azoles include, for example, pyrazoles, imidazoles, thiazoles, oxazoles, isoxazoles and triazoles.
  • Azole carboxylate safeners are a class of safeners based on carboxylate-substituted azole moieties.
  • azole carboxylate safeners include pyrazole carboxylate safeners, imidazole carboxylate safeners, thiazole carboxylate safeners, oxazole carboxylate safeners, isoxazole carboxylate safeners, and triazole carboxylate safeners.
  • the composition can include an azole carboxylate safener selected from the group consisting of fenchlorazole, flurazole, furilazole, isoxadifen, mefenpyr, agriculturally acceptable salts or esters thereof, or combinations thereof.
  • the azole carboxylate safener can include fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, or combinations thereof.
  • the azole carboxylate safener can comprise fenchlorazole, shown below, or an agriculturally acceptable salt or ester thereof. Fenchlorazole’s safening activity is described in The Pesticide Manual, Eighteenth Edition, 2016.
  • the fenchlorazole is provided as an agriculturally acceptable salt or ester.
  • An exemplary agriculturally acceptable ester of fenchlorazole is fenchlorazole–ethyl, shown below.
  • the azole carboxylate safener can comprise flurazole, shown below, or an agriculturally acceptable salt or ester thereof. Flurazole’s safening activity is described in The Pesticide Manual, Eighteenth Edition, 2016. In some aspects, the azole carboxylate safener can comprise furilazole, shown below, or an agriculturally acceptable salt or ester thereof. Furilazole’s safening activity is described in The Pesticide Manual, Eighteenth Edition, 2016. In some aspects, the azole carboxylate safener can comprise isoxadifen, shown below, or an agriculturally acceptable salt or ester thereof. Isoxadifen’s safening activity is described in The Pesticide Manual, Eighteenth Edition, 2016.
  • the isoxadifen is provided as an agriculturally acceptable salt or ester.
  • An exemplary agriculturally acceptable ester of isoxadifen is isoxadifen-ethyl, shown below.
  • the azole carboxylate safener can comprise mefenpyr, shown below, or an agriculturally acceptable salt or ester thereof. Mefenpyr’s safening activity is described in The Pesticide Manual, Eighteenth Edition, 2016.
  • the mefenpyr is provided as an agriculturally acceptable salt or ester.
  • An exemplary agriculturally acceptable ester of mefenpyr is mefenpyr-diethyl, shown below.
  • Azole carboxylate safeners include, for example, isoxadifen and agriculturally acceptable salts and esters thereof. Isoxadifen has the following chemical structure. This form of isoxadifen may also be referred to as "isoxadifen-acid.”
  • the safener may comprise isoxadifen-acid, an agriculturally acceptable salt of isoxadifen, an agriculturally acceptable ester of isoxadifen, or mixtures thereof.
  • an exemplary agriculturally acceptable ester of isoxadifen is isoxadifen-ethyl, shown below.
  • the azole carboxylate safener can be provided as an agriculturally acceptable ester.
  • Suitable esters include, but are not limited to, methyl, ethyl, isopropyl, butyl, hexyl, heptyl, isoheptyl, mexyl, isooctyl, 2-ethylhexyl and butoxyethyl esters, and aryl esters such as benzyl.
  • Exemplary agriculturally acceptable esters of the azole carboxylate safeners described herein include methyl, ethyl, and diethyl esters.
  • the azole carboxylate safener can comprise an agriculturally acceptable salt of the azole carboxylate safener.
  • Agriculturally acceptable salts of the azole carboxylate safener include, for example sodium, potassium, ammonium, monoethanolammonium, diethanolammonium, triethanolammonium, monoisopropanolammonium, diisopropanolammonium, triisopropanolammonium, choline, N,N-dimethylethanolammonium, diethylammonium, dimethylammonium, trimethylammonium, triethylammonium, and isopropylammonium salts of the azole carboxylate safener.
  • An azole carboxylate safener when applied in combination with herbicides, can be used to reduce phytotoxicity to crops such as wheat, barley, triticale, rye, teff, oats, maize, sorghum, millet, rice, millet, canola/oilseed rape, flax, soy, sunflower, sugar beet, cotton, sugarcane, and pasture grasses.
  • crops such as wheat, barley, triticale, rye, teff, oats, maize, sorghum, millet, rice, millet, canola/oilseed rape, flax, soy, sunflower, sugar beet, cotton, sugarcane, and pasture grasses.
  • the azole carboxylate safener or an agriculturally acceptable salt or ester thereof can be used in an amount sufficient to induce a safening effect.
  • the azole carboxylate safener is selected from the group consisting of fenchlorazole, fenclorim, flurazole, furilazole, isoxadifen, mefenpyr, an agriculturally acceptable salt or ester thereof, or combinations thereof, and is applied to vegetation or an area adjacent the vegetation or applied to soil or water in an amount of 1 g active ingredient per hectare (ai/ha) or greater, such as 2 g ai/ha or greater, 3 g ai/ha or greater, 4 g ai/ha or greater, 5 g ai/ha or greater, 6 g ai/ha or greater, 7 g ai/ha or greater, 8 g ai/ha or greater, 9 g ai/ha or greater, 10 g ai/ha or greater, 11 g ai/ha or greater, 12 g ai/ha or greater, 13 g ai/ha or greater, 14 g ai/ha or greater,
  • compositions and methods disclosed herein can also be mixed with or applied with an additive.
  • the additive is added sequentially.
  • the additive is added simultaneously.
  • the additive is premixed with the compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof).
  • the additive is premixed with the azole carboxylate safener or agriculturally acceptable salt or ester thereof.
  • OTHER PESTICIDES Some aspects of the disclosed safened compositions disclosed include adding one or more additional pesticide active ingredients to the safened compositions.
  • pesticide active ingredients may include one or more of an herbicide, an insecticide, a fungicide, a nematocide, a miticide, a arthropodicide, a bactericide, a plant growth regulator, or combinations thereof that are compatible with the compositions of the present disclosure.
  • the additive is an additional herbicide.
  • the compositions described herein can be applied in conjunction with one or more additional herbicides to control undesirable vegetation.
  • the composition can be formulated with the one or more additional herbicides, tank mixed with the one or more additional herbicides, or applied sequentially with the one or more additional herbicides, such as the exemplary herbicides described below.
  • the compositions can include an acetolactate synthase (ALS) inhibitor.
  • ALS inhibitors disrupt the production of amino acids in the plant, which eventually leads to inhibition of DNA synthesis.
  • ALS inhibitors include sulfonylureas, imidazolinones, triazolopyrimidine sulfonamides, pyrimidinyl oxybenzoates and sulfonylaminocarbonyl triazolinones.
  • the ALS inhibitor can contain a triazolopyrimidine sulfonamide herbicide.
  • the ALS inhibitor can contain an imidazolinone herbicide. In some aspects, the ALS inhibitor can contain a pyrimidinyl oxybenzoate herbicide. In some aspects, the ALS inhibitor can contain a sulfonylaminocarbonyl triazolinone herbicide. In some aspects, the ALS inhibitor can contain a sulfonylurea herbicide. In some aspects, the composition can include an ALS inhibitor selected from the group of imidazolinones, triazolopyrimidine sulfonamides, pyrimidinyl oxybenzoates, sulfonylaminocarbonyl triazolinones, sulfonylureas, and combinations thereof.
  • the composition can include amidosulfuron, azimsulfuron, bispyribac, bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cloransulam, cyclosulfamuron, diclosulam, ethametsulfuron, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucetosulfuron, flumetsulam, flupyrsulfuron, foramsulfuron, halosulfuron, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iofensulfuron, mesosulfuron, metazosulfuron, metosulam, metsulfuron, nicosulfuron, orthosulfamuron, oxasulfur
  • the ALS inhibitor or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the ALS inhibitor or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 0.25 grams active ingredient per hectare (g ai/ha) or more, such as 0.3 g ai/ha or more, 0.4 g ai/ha or more, 0.5 g ai/ha or more, 0.6 g ai/ha or more, 0.7 g ai/ha or more, 0.8 g ai/ha or more, 0.9 g ai/ha or more, 1 g ai/ha or more, 1.5 g ai/ha or more, 2 g ai/ha or more, 2.5 g ai/ha or more, 3 g ai/
  • the composition contains a herbicidally effective amount of compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) florasulam, cloransulam, diclosulam, flumetsulam, metosulam, penoxsulam, or pyroxsulam, or agriculturally acceptable salts or esters thereof.
  • Florasulam Compositions and methods of the present disclosure can include florasulam or an agriculturally acceptable salt or ester thereof.
  • Florasulam shown below, is a triazolopyrimidine sulfonamide that provides broad-spectrum control of many broad-leaved weeds in cereals and maize. Florasulam, as well as methods of preparing florasulam, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Sixteenth Edition, 2012. Florasulam can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • florasulam is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 0.25 g ai/ha or more, such as 0.3 g ai/ha or more, 0.4 g ai/ha or more, 0.5 g ai/ha or more, 0.6 g ai/ha or more, 0.7 g ai/ha or more, 0.8 g ai/ha or more, 0.9 g ai/ha or more, 1 g ai/ha or more, 1.1 g ai/ha or more, 1.25 g ai/ha or more, 1.5 g ai/ha or more, 1.75 g ai/ha or more, 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25
  • Cloransulam Compositions and methods of the present disclosure can include cloransulam or an agriculturally acceptable salt or ester thereof.
  • Cloransulam as well as methods of preparing cloransulam, are known in the art.
  • cloransulam can be provided as an agriculturally acceptable ester of cloransulam.
  • Cloransulam-methyl shown below, is a triazolopyrimidine sulfonamide that provides broad-spectrum control of many broadleaf weeds in soybeans and other broadleaf crops. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Cloransulam can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • cloransulam is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2.18 g ai/ha or more, such as 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.5 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9g ai/ha or
  • Diclosulam Compositions and methods of the present disclosure can include diclosulam or an agriculturally acceptable salt or ester thereof.
  • Diclosulam shown below, is a triazolopyrimidine sulfonamide that provides broad-spectrum control of many broadleaf weeds in soybeans and peanuts.
  • Diclosulam, as well as methods of preparing diclosulam, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Diclosulam can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • diclosulam is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2.18 g ai/ha or more, such as 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more, 4 g ai/ha or more, 4.5 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12 g ai/ha or more, 14 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more,
  • Flumetsulam Compositions and methods of the present disclosure can include flumetsulam or an agriculturally acceptable salt or ester thereof.
  • Flumetsulam shown below, is a triazolopyrimidine sulfonamide that provides control of broadleaf weeds and greens in soybeans, field peas, and maize. Flumetsulam, as well as methods of preparing flumetsulam, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Flumetsulam can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • flumetsulam is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2.18 g ai/ha or more, such as 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.5 g ai/ha or more, 4 g ai/ha or more, 4.5 g ai/ha or more, 5 g ai/ha or more, 7 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 36 g ai/ha or more, 37 g ai/ha or more, 38 g ai/ha or more, 39
  • Penoxsulam Compositions and methods of the present disclosure can include penoxsulam or an agriculturally acceptable salt or ester thereof.
  • Penoxsulam shown below, is a triazolopyrimidine sulfonamide that provides control of Echinochloa spp., as well as many broadleaf, sedge, and aquatic weeds in rice.
  • Penoxsulam, as well as methods of preparing penoxsulam are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Penoxsulam can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • penoxsulam is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2.5 g ai/ha or more, such as 2.75 g ai/ha or more, 3 g ai/ha or more, 3.5 g ai/ha or more, 4 g ai/ha or more, 4.5 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12 g ai/ha or more, 14 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g
  • Pyroxsulam Compositions and methods of the present disclosure can include pyroxsulam or an agriculturally acceptable salt or ester thereof.
  • Pyroxsulam shown below, is a triazolopyrimidine sulfonamide that provides broad spectrum post-emergence annual grass and broadleaf weeds control in cereals. Pyroxsulam, as well as methods of preparing pyroxsulam, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Pyroxsulam can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pyroxsulam is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1.9 g ai/ha or more, such as 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.5 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 9.5 g ai/ha or more, 10 g ai/ha or more, 10.5 g ai/ha or
  • the composition contains a herbicidally effective amount of compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, or agriculturally acceptable salts or esters thereof, or combinations thereof.
  • Imazamethabenz Compositions and methods of the present disclosure can include imazamethabenz or an agriculturally acceptable salt or ester thereof.
  • Imazamethabenz shown below, is a mixture of isomers and an imidazolinone that provides post-emergence control of Avena species, Alopecurus myosuroides, Apera spica-venti and dicotyledonous weeds in wheat, barley, rye and sunflowers.
  • Imazamethabenz, as well as methods of preparing imazamethabenz are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Imazamethabenz can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • imazamethabenz is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g a
  • Imazamox Compositions and methods of the present disclosure can include imazamox or an agriculturally acceptable salt or ester thereof.
  • Imazamox shown below, is an imidazolinone that provides pre- and post-emergence control of broadleaf and grass weeds, e.g., in rice, maize, rape, alfalfa, peas and beans.
  • Imazamox, as well as methods of preparing imazamox are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Imazamox can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • imazamox is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 5 g ai/ha or more, such as 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha or more, 21 g ai/ha or more, 22 g ai/ha or more, 23 g ai/ha or more, 24 g ai/ha or
  • Imazapic Compositions and methods of the present disclosure can include imazapic or an agriculturally acceptable salt or ester thereof.
  • Imazapic shown below, is an imidazolinone that provides pre- and post-emergence control of a wide range of annual and perennial weeds in pasture, rangeland and non-cropland areas.
  • Imazapic, as well as methods of preparing imazapic are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Imazapic can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • imazapic is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 17.5 g ai/ha or more, such as 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more
  • Imazapyr Compositions and methods of the present disclosure can include imazapyr or an agriculturally acceptable salt or ester thereof.
  • Imazapyr shown below, is an imidazolinone that provides pre- and post-emergence control of annual and perennial grasses, broadleaf weeds, brush and trees.
  • Imazapyr, as well as methods of preparing imazapyr are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Imazapyr can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • imazapyr is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 g ai/ha or more, such as 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, 275 g ai/ha or more, 300 g ai/ha or more, 325 g ai/ha or more, 350 g ai/ha or more, 375 g ai/ha or more, 400 g ai/ha or more, 4
  • Imazethapyr Compositions and methods of the present disclosure can include imazethapyr or an agriculturally acceptable salt or ester thereof.
  • Imazethapyr shown below, is an imidazolinone that controls many major annual and perennial grass and broadleaf weeds in most major crops.
  • Imazethapyr, as well as methods of preparing imazethapyr, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Imazethapyr can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • imazethapyr is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 8.75 g ai/ha or more, such as 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 80 g
  • the composition contains a herbicidally effective amount of compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) bispyribac, pyribenzoxim, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac, or agriculturally acceptable salts or esters thereof, or combinations thereof.
  • Bispyribac Compositions and methods of the present disclosure can include bispyribac or an agriculturally acceptable salt or ester thereof.
  • Bispyribac-sodium shown below, is a pyrimidinyl oxybenzoate that provides control of grasses, sedges and broadleaf weeds, e.g., in direct-seeded and water-seeded rice and in turf.
  • Bispyribac-sodium, as well as methods of preparing bispyribac-sodium, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Bispyribac can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • bispyribac is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 5 g ai/ha or more, such as 7.5 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 22.5 g ai/ha or more, 25 g ai/ha or more, 27.5 g ai/ha or more, 30 g ai/ha or more, 32.5 g ai/ha or more, 35 g ai/ha or more, 37.5 g ai/ha or more, 40 g ai/ha or more, 42.5 g ai/ha or more, 45 g ai/ha or more, 47.5 g ai/ha or more, 50 g ai/ha or
  • Pyribenzoxim Compositions and methods of the present disclosure can include pyribenzoxim or an agriculturally acceptable salt or ester thereof.
  • Pyribenzoxim shown below, is a pyrimidinyl oxybenzoate that provides post-emergence control of barnyard grass, blackgrass and Polygonum species in rice, wheat and zoysiagrass.
  • Pyribenzoxim, as well as methods of preparing pyribenzoxim are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Pyribenzoxim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pyribenzoxim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 7.5 g ai/ha or more, such as 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g ai/ha or more, 30 g ai/ha or more, 32 g
  • Pyriftalid Compositions and methods of the present disclosure can include pyriftalid or an agriculturally acceptable salt or ester thereof.
  • Pyriftalid shown below, is a pyrimidinyl oxybenzoate that provides control of grass weeds in rice. Pyriftalid, as well as methods of preparing pyriftalid, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Pyriftalid can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pyriftalid is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 22 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/
  • Pyriminobac Compositions and methods of the present disclosure can include pyriminobac or an agriculturally acceptable salt or ester thereof.
  • Pyriminobac shown below, is a pyrimidinyl oxybenzoate that provides post-emergence control of Echinochloa spp., in paddy rice.
  • Pyriminobac, as well as methods of preparing pyriminobac, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Pyriminobac can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pyriminobac is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 22 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, or 170 g ai/ha or more; in an amount
  • the composition contains a herbicidally effective amount of compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) flucarbazone, propoxycarbazone, thiencarbazone, or agriculturally acceptable salts or esters thereof, or combinations thereof.
  • Flucarbazone Compositions and methods of the present disclosure can include flucarbazone or an agriculturally acceptable salt or ester thereof.
  • Flucarbazone shown below, is a sulfonylamino- carbonyl triazolinone that provides post-emergence control of annual grass weeds and some perennial grass weeds and some broad-leaved weeds.
  • Flucarbazone as well as methods of preparing flucarbazone, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Flucarbazone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • flucarbazone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 3.75 g ai/ha or more, such as 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.25 g ai/ha or more, 5.5 g ai/ha or more, 5.75 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 7.5 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more
  • Propoxycarbazone Compositions and methods of the present disclosure can include propoxycarbazone or an agriculturally acceptable salt or ester thereof.
  • Propoxycarbazone shown below, is a sulfonylaminocarbonyl triazolinone that provides post-emergence control of grass weeds and some broad-leaved weeds.
  • Propoxycarbazone, as well as methods of preparing propoxycarbazone are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Propoxycarbazone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • propoxycarbazone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 3.75 g ai/ha or more, such as 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12 g ai/ha or more, 14 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g g
  • Thiencarbazone Compositions and methods of the present disclosure can include thiencarbazone or an agriculturally acceptable salt or ester thereof.
  • Thiencarbazone-methyl shown below, is a sulfonylaminocarbonyl triazolinone that provides post-emergence control of grass weeds and some broad-leaved weeds.
  • Thiencarbazone, as well as methods of preparing thiencarbazone, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Thiencarbazone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • thiencarbazone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2.5 g ai/ha or more, such as 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12 g ai/ha or more, 14 g ai/ha or more, 16 g ai/ha or
  • the composition contains a herbicidally effective amount of compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) amidosulfuron, azimsulfuron, bensulfuron, chlorimuron, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, iofensulfuron, mesosulfuron, metazosulfuron, metsulfuron, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, propyrisulfuron, prosulfuron, pyrazosulfur
  • Amidosulfuron Compositions and methods of the present disclosure can include amidosulfuron or an agriculturally acceptable salt or ester thereof.
  • Amidosulfuron shown below, is a sulfonylurea that provides post-emergence control of a wide range of broadleaf weeds, e.g., cleavers, in winter wheat, durum wheat, barley, rye, triticale and oats.
  • Amidosulfuron, as well as methods of preparing amidosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Amidosulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • amidosulfuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 3.75 g ai/ha or more, such as 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15
  • Azimsulfuron Compositions and methods of the present disclosure can include azimsulfuron or an agriculturally acceptable salt or ester thereof.
  • Azimsulfuron shown below, is a sulfonylurea that provides e.g., post-emergence control of annual and perennial broadleaf and sedge weeds in rice.
  • Azimsulfuron, as well as methods of preparing azimsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Azimsulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • azimsulfuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 3.125 g ai/ha or more, such as 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.5 g ai/ha or more, 6 g ai/ha or more, 6.5 g ai/ha or more, 7 g ai/ha or more, 7.5 g ai/ha or more, 8 g ai/ha or more, 8.5 g ai/ha or more, 9 g ai/ha or more, 9.5 g ai/ha or more, 10 g g a
  • Bensulfuron Compositions and methods of the present disclosure can include bensulfuron or an agriculturally acceptable salt or ester thereof.
  • Bensulfuron-methyl shown below, is a sulfonylurea that provides e.g., pre- and post-emergence control of annual and perennial broadleaf weeds and sedges in rice.
  • Bensulfuron, as well as methods of preparing bensulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Bensulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • bensulfuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 8.75 g ai/ha or more, such as 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g ai/ha or more, 30 g ai/ha or more, 32 g ai/ha or more, 34 g ai/
  • Chlorsulfuron Compositions and methods of the present disclosure can include chlorsulfuron or an agriculturally acceptable salt or ester thereof.
  • Chlorsulfuron shown below, is a sulfonylurea that provides control of e.g., broadleaf weeds and annual grasses in wheat, barley, oats, rye, triticale, flax and on non-crop land.
  • Chlorsulfuron, as well as methods of preparing chlorsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Chlorsulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • chlorsulfuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1.1 g ai/ha or more, such as 1.25 g ai/ha or more, ., 1.5 g ai/ha or more, 1.75 g ai/ha or more, 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5 g
  • Ethoxysulfuron Compositions and methods of the present disclosure can include ethoxysulfuron or an agriculturally acceptable salt or ester thereof.
  • Ethoxysulfuron shown below, is a sulfonylurea that provides e.g., control of broadleaf and sedge weeds in cereals, rice and sugar cane.
  • Ethoxysulfuron, as well as methods of preparing ethoxysulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Ethoxysulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • ethoxysulfuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 5 g ai/ha or more, such as 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g
  • Flupyrsulfuron Compositions and methods of the present disclosure can include flupyrsulfuron or an agriculturally acceptable salt or ester thereof.
  • Flupyrsulfuron-methyl sodium shown below, is a sulfonylurea that is used, e.g., for post-emergent control of grass and broadleaf weeds in cereals.
  • Flupyrsulfuron, as well as methods of preparing flupyrsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Flupyrsulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • flupyrsulfuron thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2.5 g ai/ha or more, such as 2.6 g ai/ha or more, 2.7 g ai/ha or more, 2.8 g ai/ha or more, 2.9 g ai/ha or more, 3.0 g ai/ha or more, 3.2 g ai/ha or more, 3.4 g ai/ha or more, 3.6 g ai/ha or more, 3.8 g ai/ha or more, 4 g ai/ha or more, 4.2 g ai/ha or more, 4.4 g ai/ha or more, 4.6 g ai/ha or more, 4.8 g ai/ha or more, 5 g ai/ha or more, 5.2 g ai/ha or more, 5.4 g ai/ha or more,
  • compositions and methods of the present disclosure can include foramsulfuron or an agriculturally acceptable salt or ester thereof.
  • Foramsulfuron shown below, is a sulfonylurea that provides e.g., post-emergence control of grass and broadleaf weeds in maize.
  • Foramsulfuron, as well as methods of preparing foramsulfuron, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Foramsulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • foramsulfuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 22.5 g ai/ha or more, such as 23 g ai/ha or more, 24 g ai/ha or more, 25 g ai/ha or more, 26 g ai/ha or more, 28 g ai/ha or more, 30 g ai/ha or more, 32 g ai/ha or more, 34 g ai/ha or more, 35 g ai/ha or more, 36 g ai/ha or more, 38 g ai/ha or more, 40 g ai/ha or more, 42 g ai/ha or more, 44 g ai/ha or more, 46 g ai/ha or more, 48 g ai/ha or more, 50 g ai/ha or more, 51 g ai/ha or more, 52 g
  • Halosulfuron Compositions and methods of the present disclosure can include halosulfuron or an agriculturally acceptable salt or ester thereof.
  • Halosulfuron-methyl shown below, is a sulfonylurea that has demonstrated activity for the control of annual broadleaf weeds and nutsedge species, in maize, sugar cane, rice, sorghum, nuts, and turf.
  • Halosulfuron, as well as methods of preparing halosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Halosulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • halosulfuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 4.375 g ai/ha or more, such as 4.75 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g
  • Iodosulfuron Compositions and methods of the present disclosure can include iodosulfuron or an agriculturally acceptable salt or ester thereof.
  • Iodosulfuron-methyl-sodium shown below, is a sulfonylurea that provides, e.g., post-emergence control of grass and broadleaf weeds in winter, spring and durum wheat, triticale, rye and spring barley.
  • Iodosulfuron, as well as methods of preparing iodosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Iodosulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • iodosulfuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 0.1 g ai/ha or more, such as 0.2 g ai/ha or greater, 0.3 g ai/ha or greater, 0.4 g ai/ha or greater, 0.5 g ai/ha or greater, 0.6 g ai/ha or greater, 0.7 g ai/ha or greater, 0.8 g ai/ha or greater, 0.9 g ai/ha or greater, 1 g ai/ha or greater, 1.1 g ai/ha or greater, 1.2 g ai/ha or greater, 1.3 g ai/ha or greater, 1.4 g ai/
  • Mesosulfuron Compositions and methods of the present disclosure can include mesosulfuron or an agriculturally acceptable salt or ester thereof.
  • Mesosulfuron-methyl shown below, is a sulfonylurea that provides, e.g., early- to mid-post-emergence control of grass and some broadleaf weeds in winter, spring and durum wheat, triticale and rye.
  • Mesosulfuron, as well as methods of preparing mesosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Mesosulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • mesosulfuron thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1.5 g ai/ha or more, such as 1.6 g ai/ha or more, 1.7 g ai/ha or more, 1.8 g ai/ha or more, 1.9 g ai/ha or more, 2 g ai/ha or more, 2.1 g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4
  • Metsulfuron Compositions and methods of the present disclosure can include metsulfuron or an agriculturally acceptable salt or ester thereof.
  • Metsulfuron-methyl shown below, is a sulfonylurea that controls, e.g., grass and broadleaf weeds in wheat, barley, rice, oats and triticale.
  • Metsulfuron, as well as methods of preparing metsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Metsulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • metsulfuron thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 1.1 g ai/ha or more,1.2 g ai/ha or more, 1.25 g ai/ha or more, 1.3 g ai/ha or more,1.4 g ai/ha or more, 1.5 g ai/ha or more, 1.6 g ai/ha or more, 1.7 g ai/ha or more, 1.8 g ai/ha or more, 1.9 g ai/ha or more, 2 g ai/ha or more, 2.1 g ai/ha or more, 2.2 g ai/ha or more, 2.3 g ai/ha or more, 2.3 g ai/ha or more, 2.4 g ai/ha or more, 2.5 g ai/ha or more, 2.6 g
  • Nicosulfuron Compositions and methods of the present disclosure can include nicosulfuron or an agriculturally acceptable salt or ester thereof.
  • Nicosulfuron shown below, is a sulfonylurea that provides e.g., selective post-emergence control in maize of annual grass weeds, including Setaria, Echinochloa, Digitaria, Panicum, Lolium and Avena spp., broadleaf weeds, including Amaranthus spp. and Cruciferae, and perennials such as Sorghum halepense and Agropyron repens. Nicosulfuron, as well as methods of preparing nicosulfuron, are known in the art.
  • Nicosulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • nicosulfuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 8.75 g ai/ha or more, such as 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g ai/ha or more, 30 g ai/ha or more, 32 g ai/ha or more, 34 g
  • Orthosulfamuron Compositions and methods of the present disclosure can include orthosulfamuron or an agriculturally acceptable salt or ester thereof.
  • Orthosulfamuron shown below, is a sulfonylurea that provides e.g., early post-emergence control of annual and perennial broadleaf weeds and sedges in rice, cereals, pastures and sugar cane.
  • Orthosulfamuron, as well as methods of preparing orthosulfamuron are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Orthosulfamuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • orthosulfamuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 7.5 g ai/ha or more, such as 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 17 g ai/ha or more, 18 g ai/ha or more, 19 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more,
  • Rimsulfuron Compositions and methods of the present disclosure can include rimsulfuron or an agriculturally acceptable salt or ester thereof.
  • Rimsulfuron shown below, is a sulfonylurea that provides post-emergence control of most annual and perennial grass weeds and several broad-leaved weeds in maize, tomatoes and potatoes, at 15 g/ha.
  • Rimsulfuron, as well as methods of preparing rimsulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Rimsulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • rimsulfuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 5 g ai/ha or more, such as 5.5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 7.5 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12 g ai/ha or more, 14 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 27 g ai/ha or more, 28 g ai/ha or more, 30 g ai/ha or more, 32 g
  • Sulfosulfuron Compositions and methods of the present disclosure can include sulfosulfuron or an agriculturally acceptable salt or ester thereof.
  • Sulfosulfuron shown below, is a sulfonylurea that provides e.g., control of annual broadleaf weeds and grass weeds in cereals.
  • Sulfosulfuron, as well as methods of preparing sulfosulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Sulfosulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • sulfosulfuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 4.375 g ai/ha or more, such as 4.75 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12 g ai/ha or more, 14 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g ai/ha or more, 30 g ai/ha or more, 32 g ai/ha or more,
  • Thifensulfuron Compositions and methods of the present disclosure can include thifensulfuron or an agriculturally acceptable salt or ester thereof.
  • Thifensulfuron-methyl shown below, is a sulfonylurea that provides e.g., control of annual weeds in cereals, maize and pasture.
  • Thifensulfuron, as well as methods of preparing thifensulfuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Thifensulfuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • thifensulfuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 4.4 g ai/ha or more, such as 4.5 g ai/ha or more, 4.6 g ai/ha or more, 4.7 g ai/ha or more, 4.8 g ai/ha or more, 4.9 g ai/ha or more, 5 g ai/ha or more, 5.2 g ai/ha or more, 5.4 g ai/ha or more, 5.6 g ai/ha or more, 5.8 g ai/ha or more, 6 g ai/ha or more, 6.2 g ai/ha or more, 6.4 g ai/ha or more, 6.6 g ai/ha or more, 6.8 g ai/ha or more, 7 g ai/ha or more, 7.2 g ai/ha or more
  • Tribenuron Compositions and methods of the present disclosure can include tribenuron or an agriculturally acceptable salt or ester thereof.
  • Tribenuron-methyl shown below, is a sulfonylurea that provides e.g., post-emergence control of broadleaf weeds in cereal crops, including wheat, barley, oats, rye and triticale.
  • Tribenuron, as well as methods of preparing tribenuron are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Tribenuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • tribenuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 3.75 g ai/ha or more, such as 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.25 g ai/ha or more, 5.5 g ai/ha or more, 5.75 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 7.5 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more
  • the compositions can include a synthetic auxin herbicide.
  • Synthetic auxin herbicides mimic natural plant hormones and can inhibit cell division and growth.
  • Synthetic auxin herbicides include phenoxy herbicides, benzoic acid herbicides, aryl picolinate herbicides, quinoline carboxylic acid herbicides, pyrimidine carboxylic acid herbicides, and benzothiazole herbicides, as well as agriculturally acceptable salts and esters thereof.
  • the composition can include a synthetic auxin herbicide selected from the group consisting of 2,4-D; 2,4-DB; 2,3,6-TBA, aminocyclopyrachlor, aminopyralid, benazolin-ethyl, chloramben, clomeprop, clopyralid, dichlorprop, dichlorprop-P, dicamba, florpyrauxifen (such as florpyrauxifen-benzyl), fluchloraminopyr (e.g., fluchloraminopyr- tefuryl), fluroxypyr, fluroxypyr-MHE, halauxifen (such as halauxifen-methyl), indolauxipyr (such as indolauxipyr-cyanomethyl), mecoprop, mecoprop-P, MCPA, MCPA-thioethyl, MCPB, picloram, quinclorac, quinmerac, triclopyr, agriculturally acceptable salts and esters thereof, and combinations thereof.
  • the synthetic auxin herbicide can comprise 2,4-D, MCPA, aminopyralid, clopyralid, dicamba, florpyrauxifen, fluroxypyr, halauxifen, quinclorac, agriculturally acceptable salts and esters thereof, and combinations thereof.
  • the synthetic auxin herbicide or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the synthetic auxin herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 gram acid equivalent per hectare (g ai) or more, such as 1.5 g ai or more, 2 g ai or more, 2.5 g ai or more, 3 g ai or more, 3.5 g ai or more, 4 g ai or more, 4.5 g ai or more, 5 g ai or more, 6 g ai or more, 7 g ai or more, 8 g ai or more, 9 g ai or more, 10 g ai or more, 15 g ai or more, 20 g ai or more, 25 g ai or more, 30 g ai or more, 35 g ai or more, 40 g ai or more, 45 g ai or more, 50 g ai) or more
  • the composition contains compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) 2,4-D, 2,4- DB2, clomeprop, dichlorprop, mecoprop, MCPA, MCPB, or agriculturally acceptable salts or esters thereof.
  • 2,4-D In some aspects, the synthetic auxin herbicide can comprise 2,4-D or an agriculturally acceptable salt or ester thereof.
  • 2,4-D shown below, is a phenoxycarboxylic acid herbicide that provides broad spectrum control of many annual, biannual and perennial broad-leaved weeds and aquatic broad-leaved weeds in cereals, maize, sorghum, grasslands, established turf, grass seed crops, orchards (pome fruit and stone fruit), cranberries, asparagus, sugar cane, rice, forestry, and on non-crop land (including areas adjacent to water).
  • 2,4- D as well as methods of preparing 2,4-D, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. In some aspects, 2,4-D can be provided as an agriculturally acceptable salt or ester of 2,4-D.
  • Exemplary agriculturally acceptable salts and esters of 2,4-D include, but are not limited to, 2,4-D-ammonium 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D choline, 2,4-D-diethylammonium, 2,4-D-dimethylammonium (2,4-D DMA), 2,4-D-diolamine, 2,4-D-dodecylammonium, 2,4-D-ethyl, 2,4-D-2-ethylhexyl (2,4-D EHE), 2,4-D-heptylammonium, 2,4-D-isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl, 2,4-D- isopropylammonium, 2,4-D-lithium, 2,4-D-meptyl, 2,4-D
  • the 2,4-D can be provided as 2,4-D-2-ethylhexyl (2,4-D EHE), shown below.
  • 2,4-D can be provided as 2,4-D DMA, shown below.
  • the 2,4-D can be provided as 2,4-D choline, shown below.
  • the 2,4-D can be provided as 2,4-D triethanolamine (2,4-D- trolamine), shown below.
  • analogs of 2,4-D such as 2,4-D diamers, aminoxy, amides, and esters.
  • Exemplary analogs of 2,4-D include the analogs disclosed in PCT/US2023/071586 filed on August 3, 2023, the disclosure of which is incorporated by reference in its entirety herein.
  • Exemplary 2,4-D analogs include the following: TABLE 23: 2,4-D ANALOGS
  • Exemplary uses of 2,4-D, such as 2,4-D-choline or 2,4-D trolamine may include, but are not limited to, controlling annual and perennial broadleaf weeds, including, but not limited to, glyphosate-resistant broadleaf weeds.
  • 2,4-D-Choline can be used in crops that have been made tolerant to 2,4-D, including, but not limited to, 2,4-D-tolerant soybeans, maize, and cotton.
  • 2,4-D-Choline is generally, but is not required to be, applied post-emergent.
  • 2,4-D- Choline can also be used for weed control in non-crop and perennial cropping systems.
  • 2,4-D can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • 2,4-D is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 gram active ingredient per hectare (g ai/ha) or more, such as 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more
  • the synthetic auxin herbicide can comprise 2,4-DB is a phenoxycarboxylic acid herbicide that provides post-emergence control of many annual and perennial broadleaf weeds in alfalfa, clovers, cereals, grassland, forage, legumes, soybeans, and peanuts.
  • 2,4-DB as well as methods of making 2,4-DB, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • 2,4-DB can be provided as an agriculturally acceptable salt or ester of 2,4-DB.
  • Exemplary agriculturally acceptable salts and esters of 2,4-DB include, but are not limited to, 2,4-DB-butyl, 2,4-DB-dimethylammonium (2,4-DB DMA), 2,4-DB-isoctyl, 2,4- DB-potassium, and 2,4-DB-sodium.
  • 2,4-DB can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • 2,4-DB is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/
  • the synthetic auxin herbicide can comprise clomeprop or an agriculturally acceptable salt or ester thereof.
  • Clomeprop shown below, is a phenoxycarboxylic acid herbicide that provides pre- to early post-emergence control of broad- leaf and sedge weeds in paddy rice. Clomeprop, as well as methods of preparing clomeprop, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Dichlorprop In some aspects, the synthetic auxin herbicide can comprise dichlorprop or an agriculturally acceptable salt or ester thereof.
  • Dichlorprop shown below, is a phenoxycarboxylic herbicide that provides broad-spectrum control of annual and perennial broad-leaved weeds in cereals and grasslands; brush control in non-crop land; control of broad- leaved aquatic weeds; and maintenance of embankments and roadside verges.
  • Dichlorprop, as well as methods of making dichlorprop, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. In some aspects, dichlorprop can be provided as an agriculturally acceptable salt or ester of dichlorprop.
  • Exemplary agriculturally acceptable salts and esters of dichlorprop include, but are not limited to, dichlorprop-butotyl, dichlorprop-dimethylammonium, dichlorprop-ethylammonium, dichlorprop-2-ethylhexyl, dichlorprop-isoctyl, dichlorprop- methyl, dichlorprop-potassium, dichlorprop-sodium, dichlorprop-P, dichlorprop-P- dimethylammonium, dichlorprop-P-2-ethylhexyl, dichlorprop-P-potassium, and dichlorprop- P-sodium.
  • the dichlorprop can be provided as the stereoisomer dichlorprop- P, shown below.
  • Dichlorprop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • dichlorprop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or
  • the synthetic auxin herbicide can comprise mecoprop or an agriculturally acceptable salt or ester thereof.
  • Mecoprop shown below, is a phenoxy carboxylic acid herbicide that provides broad-spectrum control of broad-leaved weeds in wheat, barley, oats, herbage seed crops, grassland, and under fruit trees and vines. Mecoprop also provides control of docks (Rumex spp.) in meadows and pastures. Mecoprop, as well as methods of making mecoprop, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. In some aspects, mecoprop can be provided as an agriculturally acceptable salt or ester of mecoprop.
  • Exemplary agriculturally acceptable salts and esters of mecoprop include, but are not limited to, mecoprop-butotyl, mecoprop-potassium, mecoprop-sodium, mecoprop- dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-trolamine, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-ethylhexyl, and mecoprop-P-potassium.
  • the mecoprop can be provided as the stereoisomer mecoprop-P, shown below.
  • Mecoprop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • mecoprop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha
  • the synthetic auxin herbicide can comprise MCPA or an agriculturally acceptable salt or ester thereof.
  • MCPA shown below, is a phenoxycarboxylic acid herbicide that provides broad-spectrum control of many annual, biannual, and perennial broad-leaved weeds, woody weeds, and aquatic broad-leaved weeds in cereals, herbage seed crops, flax, rice, vines, peas, potatoes, asparagus, grassland, turf, under fruit trees, forestry, and on roadside verges and embankments.
  • MCPA as well as methods of preparing MCPA, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • MCPA can be provided as an agriculturally acceptable salt or ester of MCPA.
  • exemplary agriculturally acceptable salts of MCPA include, but are not limited to, MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium (MCPA-DMA), MCPA- diolamine, MCPA-ethyl, MCPA-2-ethylhexyl (MCPA EHE), MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, MCPA-trolamine.
  • the MCPA can be provided as MCPA-2-ethylhexyl (MCPA EHE), shown below. In some aspects, the MCPA can be provided as MCPA-dimethylammonium (MCPA-DMA), shown below.
  • MCPA can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • MCPA is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more such as 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or
  • the synthetic auxin herbicide can comprise MCPB or an agriculturally acceptable salt or ester thereof.
  • MCPB shown below, is a phenoxycarboxylic acid herbicide that provides broad-spectrum control of many broad-leaved weeds, woody weeds, and aquatic broad-leaved weeds in rice, cereals, clovers, sainfoin, peas, peanuts, grassland, turf, and forestry.
  • MCPB as well as methods of preparing MCPB, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • MCPB can be provided as an agriculturally acceptable salt or ester of MCPB.
  • Exemplary agriculturally acceptable salts of MCPB include, but are not limited to, MCPB-ethyl, MCPB-potassium, and MCPB-sodium.
  • MCPB can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • MCPB is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha
  • the composition contains compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) chloramben, dicamba, TBA, or agriculturally acceptable salts or esters thereof.
  • Chloramben In some aspects, the synthetic auxin herbicide can comprise chloramben or an agriculturally acceptable salt or ester thereof. Chloramben, shown below, is a benzoic acid herbicide that provides pre-planting and pre-emergence control of grasses and broad-leaved weeds in asparagus, navy beans, peanuts, maize, sweet potatoes, pumpkins, soybeans, squash, sunflowers, and certain ornamentals.
  • Chloramben as well as methods of preparing chloramben, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Dicamba
  • the synthetic auxin herbicide can comprise dicamba or an agriculturally acceptable salt or ester thereof.
  • Dicamba shown below, is a benzoic acid herbicide that provides broad-spectrum control of annual and perennial broad-leaved weeds and brush species in cereals, maize, sorghum, sugar cane, asparagus, perennial seed grasses, turf, pastures, rangeland, and non-crop land. Dicamba, as well as methods of making dicamba, are known in the art.
  • dicamba can be provided as an agriculturally acceptable salt or ester of dicamba.
  • exemplary agriculturally acceptable salts and esters of dicamba include, but are not limited to, dicamba-diglycolammonium, dicamba-dimethylammonium, dicamba- diolamine, dicamba-isopropylammonium, dicamba-methyl, dicamba-olamine, dicamba- potassium, dicamba-sodium, dicamba-trolamine, and cambendichlor.
  • dicamba can be provided as dicamba-diglycolammonium, shown below.
  • Dicamba can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • dicamba is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha
  • the synthetic auxin herbicide can comprise 2,3,6-TBA or an agriculturally acceptable salt or ester thereof.
  • 2,3,6-TBA shown below, is a benzoic acid herbicide that provides post-emergence control of certain broad-leaved annual and perennial weeds in cereals and grass seed crops.
  • 2,3,6-TBA, as well as methods of preparing 2,3,6-TBA are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. C.
  • the composition contains compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) florpyrauxifen, halauxifen, or agriculturally acceptable salts or esters thereof.
  • Florpyrauxifen In some aspects, the synthetic auxin herbicide can comprise florpyrauxifen or an agriculturally acceptable salt or ester thereof. Florpyrauxifen is aryl picolinic acid that has been described in U.S. Patent 7,314,849 B2. Exemplary uses of florpyrauxifen include controlling undesirable vegetation, including grass, broadleaf and sedge weeds, in multiple non-crop and cropping situations.
  • florpyrauxifen can be provided as an agriculturally acceptable salt or ester of florpyrauxifen.
  • exemplary agriculturally acceptable salts and esters of florpyrauxifen include, but are not limited to, florpyrauxifen-benzyl, shown below.
  • Florpyrauxifen can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • florpyrauxifen is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50
  • the synthetic auxin herbicide can comprise halauxifen or an agriculturally acceptable salt or ester thereof.
  • Halauxifen shown below, is a aryl picolinic acid herbicide that provides broad-spectrum control of broad-leaved weeds in cereal crops.
  • halauxifen can be provided as an agriculturally acceptable salt or ester of halauxifen.
  • Exemplary agriculturally acceptable salts and esters of halauxifen include, but are not limited to, halauxifen-methyl.
  • the halauxifen is provided as halauxifen-methyl, shown below.
  • Halauxifen can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • halauxifen is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 2 g ai/ha or more, 2.5 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 25 g g
  • the composition contains compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) aminopyralid, clopyralid, fluroxypyr, picloram, triclopyr, or agriculturally acceptable salts or esters thereof.
  • Aminopyralid In some aspects, the synthetic auxin herbicide can comprise aminopyralid or an agriculturally acceptable salt or ester thereof.
  • Aminopyralid is a compounds according to that provides pre- and post-emergence control of certain annual and perennial broadleaf weeds in grasslands. Aminopyralid, as well as methods of making aminopyralid, are known in the art.
  • aminopyralid can be provided as an agriculturally acceptable salt or ester of aminopyralid.
  • exemplary agriculturally acceptable salts and esters of aminopyralid include, but are not limited to, for example, aminopyralid-triisopropanolammonium (TIPA), shown below.
  • TIPA aminopyralid-triisopropanolammonium
  • Aminopyralid can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • aminopyralid is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 2 g ai/ha or more, 2.5 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g a
  • the synthetic auxin herbicide can comprise clopyralid or an agriculturally acceptable salt or ester thereof.
  • Clopyralid shown below, is a compound that provides post-emergence control of many annual and perennial broad-leaved weeds in sugar beet, fodder beet, oilseed rape, maize, cereals, brassicas, onions, leeks, strawberries, flax, grassland, and non-crop lands.
  • Clopyralid, as well as methods of making clopyralid are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • clopyralid can be provided as an agriculturally acceptable salt or ester of clopyralid.
  • Exemplary agriculturally acceptable salts and esters of clopyralid include, but are not limited to, clopyralid-methyl, clopyralid-potassium, clopyralid-tris(2- hydroxypropyl)ammonium, and clopyralid-olamine, shown below.
  • Clopyralid can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • clopyralid is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 25 g ai/ha or more, such as 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g a
  • the synthetic auxin herbicide can comprise fluroxypyr or an agriculturally acceptable salt or ester thereof.
  • Fluroxypyr shown below, is a compound that provides post-emergence control against certain broad-leaved weeds in small grain crops, pastures, grasslands, orchards, plantation crops, maize, and forestry. Fluroxypyr, as well as methods of making fluroxypyr, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. In some aspects, fluroxypyr can be provided as an agriculturally acceptable salt or ester of fluroxypyr.
  • Exemplary agriculturally acceptable salts and esters of fluroxypyr include, but are not limited to, fluroxypyr-2-butoxy-1-methylethyl (fluroxypyr-butometyl) and fluroxypyr-meptyl (fluroxypyr-MHE).
  • the fluroxypyr can be provided as fluroxypyr-meptyl (fluroxypyr-MHE), shown below. Fluroxypyr can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • fluroxypyr is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 35 g ai/ha or more, such as 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or
  • the synthetic auxin herbicide can comprise picloram or an agriculturally acceptable salt or ester thereof.
  • Picloram is a compounds that provides management of unwanted vegetation in rangeland, grass pastures, forestry, as well as non-crop land and right-of-way sites. Picloram, as well as methods of making picloram, is known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. In some aspects, picloram can be provided as an agriculturally acceptable salt or ester of picloram.
  • Exemplary agriculturally acceptable salts and esters of picloram include, but are not limited to, picloram-dimethylammonium, picloram-isoctyl, picloram-potassium, picloram-triethylammonium, picloram-triisopropanolammonium (TIPA), picloram- triisopropylammonium, and picloram-trolamine (triethanolammonium).
  • the picloram can be provided as picloram-potassium, shown below.
  • the picloram can be provided as picloram-TIPA, shown below.
  • Picloram can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • picloram is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 10 g ai/ha or more, such as 12 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or
  • the synthetic auxin herbicide can comprise triclopyr or an agriculturally acceptable salt or ester thereof.
  • Triclopyr is a compound that provides control of woody plants and broadleaf weed species in grassland, rangeland, industrial areas, coniferous forests, rice, and plantation crops. Triclopyr, as well as methods of making triclopyr, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. In some aspects, triclopyr can be provided as an agriculturally acceptable salt or ester of triclopyr.
  • Exemplary agriculturally acceptable salts and esters of triclopyr include, but are not limited to, for example, triclopyr-triethylammonium (TEA), triclopyr choline, and triclopyr-butotyl (butoxyethyl or BEE).
  • TAA triclopyr-triethylammonium
  • BEE triclopyr-butotyl
  • the triclopyr can be provided as triclopyr-triethylammonium (TEA), shown below.
  • the triclopyr can be provided as triclopyr-choline, shown below.
  • the triclopyr can be provided as triclopyr-BEE, shown below.
  • Triclopyr can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • triclopyr is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 10 g ai/ha or more, such as 12 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 125 g ai/
  • the composition contains compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) quinclorac, quinmerac, or agriculturally acceptable salts or esters thereof.
  • Quinclorac In some aspects, the synthetic auxin herbicide can comprise quinclorac or an agriculturally acceptable salt or ester thereof.
  • Quinclorac shown below, is a quinoline carboxylic acid herbicide that provides pre- and post-emergence control of certain grass weeds and other weeds in direct-seeded and transplanted rice. Quinclorac, as well as methods of making quinclorac, are known in the art.
  • quinclorac can be provided as an agriculturally acceptable salt or ester of quinclorac.
  • exemplary agriculturally acceptable salts and esters of quinclorac include, but are not limited to, quinclorac-dimethylammonium.
  • Quinclorac can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • quinclorac is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 10 g ai/ha or more, such as 12 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 125 g ai
  • the synthetic auxin herbicide can comprise quinmerac or an agriculturally acceptable salt or ester thereof.
  • Quinmerac shown below, is a quinoline carboxylic acid herbicide that provides control of certain broad-leaved weeds in cereals, oilseed rape, and sugar beets.
  • Quinmerac as well as methods of making quinmerac, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Quinmerac can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • quinmerac is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 10 g ai/ha or more, such as 12 g ai/ha or more, 14 g ai/ha or more, 15 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 125 g ai
  • the composition contains compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) aminocyclopyrachlor, benazolin, or agriculturally acceptable salts or esters thereof.
  • Aminocyclopyrachlor In some aspects, the synthetic auxin herbicide can comprise aminocyclopyrachlor or an agriculturally acceptable salt or ester thereof.
  • Aminocyclopyrachlor shown below, is a pyrimidine carboxylic acid herbicide that provides control of certain broadleaf weeds and woody species, e.g., in rights-of-way, industrial sites, rangeland, permanent grass pastures and natural areas.
  • aminocyclopyrachlor as well as methods of making aminocyclopyrachlor, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • aminocyclopyrachlor can be provided as an agriculturally acceptable salt or ester of aminocyclopyrachlor.
  • exemplary agriculturally acceptable salts and esters of aminocyclopyrachlor include, but are not limited to, aminocyclopyrachlor-potassium and aminocyclopyrachlor-methyl.
  • Aminocyclopyrachlor can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • aminocyclopyrachlor is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g g g
  • the synthetic auxin herbicide can comprise benazolin or an agriculturally acceptable salt or ester thereof.
  • Benazolin shown below, is a benzothiazole herbicide that provides post-emergence control of certain annual broad-leaved weeds in cereals, oilseed rape, grassland, clover, alfalfa, and flax. Benazolin, as well as methods of making benazolin, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. In some aspects, benazolin can be provided as an agriculturally acceptable salt or ester of benazolin.
  • Exemplary agriculturally acceptable salts and esters of benazolin include, but are not limited to, benazolin-ethyl.
  • AUXIN TRANSPORT INHIBITORS the pyridine carboxylic acid herbicide or agriculturally acceptable N- oxide, salt or ester thereof, the compositions can include an auxin transport inhibitor.
  • auxin transport inhibitors inhibit polar transport of naturally occurring auxin, indole acetic acid (IAA), and synthetic auxin-mimicking herbicides in sensitive plants.
  • auxin transport inhibitors include phthalamate herbicides, semicarbazone herbicides and others.
  • the composition can include an auxin transport inhibitor selected from the group consisting of: chlorflurenol; diflufenzopyr; naptalam; 2,3,5-triiodobenzoic acid (2,3,5-TIBA); agriculturally acceptable salts and esters thereof; and combinations thereof.
  • Chlorflurenol In some aspects, the auxin transport inhibitor can comprise chlorflurenol or an agriculturally acceptable salt or ester thereof. Chlorflurenol, shown below, is a herbicide that is a growth retardant and weed suppressant in amenity grass, roadsides, railways, ditch banks, etc. Chlorflurenol, as well as methods of preparing chlorflurenol, are known in the art.
  • Chlorflurenol can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • chlorflurenol is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 g ai/ha or greater, such as 110 g ai/ha or greater, 120 g ai/ha or greater, 130 g ai/ha or greater, 140 g ai/ha or greater, 150 g ai/ha or greater, 160 g ai/ha or greater, 170 g ai/ha or greater, 180 g ai/ha or greater, 190 g ai/ha or greater, 200 g ai/ha or greater, 220 g ai/ha or greater, 240 g ai/ha or greater, 250 g ai/ha or greater, 260 g ai/ha or greater, 280 g ai/ha or greater, 300 g ai/ha or greater, 320 g ai/ha or greater, 340 g ai/ha or greater, 300
  • the auxin transport inhibitor can comprise diflufenzopyr or an agriculturally acceptable salt or ester thereof.
  • Diflufenzopyr shown below, is a semicarbazone herbicide that provides post-emergence control of annual and perennial broad-leaved weeds in maize, pastures, rangeland, and non-crop areas.
  • Diflufenzopyr, as well as methods of preparing diflufenzopyr, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary forms of diflufenzopyr include its sodium salt.
  • Diflufenzopyr can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • diflufenzopyr is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or greater, such as 1.5 g ai/ha or greater, 2 g ai/ha or greater, 2.5 g ai/ha or greater, 3 g ai/ha or greater, 3.5 g ai/ha or greater, 4 g ai/ha or greater, 5 g ai/ha or greater, 6 g ai/ha or greater, 7 g ai/ha or greater, 8 g ai/ha or greater, 9 g ai/ha or greater, 10 g ai/ha or greater, 15 g ai/ha or greater, 20 g ai/ha or greater, 25
  • the auxin transport inhibitor can comprise naptalam or an agriculturally acceptable salt or ester thereof.
  • Naptalam is a phthalamate herbicide that provides pre-emergence control of many broad-leaved weeds and some grasses in cucurbits, asparagus, peanuts, soybeans, and established woody ornamentals. It is described in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary forms of naptalam include its sodium salt. Naptalam can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce an herbicidal effect.
  • naptalam is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 140 g ai/ha or greater, such as 150 g ai/ha or greater, 200 g ai/ha or greater, 300 g ai/ha or greater, 400 g ai/ha or greater, 500 g ai/ha or greater, 600 g ai/ha or greater, 700 g ai/ha or greater, 750 g ai/ha or greater, 800 g ai/ha or greater, 900 g ai/ha or greater, 1000 g ai/ha or greater, 1100 g ai/ha or greater, 1200 g ai/ha or greater, 1250 g ai/ha or greater, 1300 g ai/ha or greater, 1400 g ai/ha or greater, 1500 g ai/ha or greater,1600 g ai/ha or greater,
  • the auxin transport inhibitor can comprise 2,3,5-triiodobenzoic acid (2,3,5-TIBA) or an agriculturally acceptable salt or ester thereof.
  • 2,3,5-TIBA is an auxin transport inhibitor that inhibits plant top growth, dwarves plants, promotes the growth of lateral buds, accelerates bud formation and flowering, and promotes rooting.
  • 2,3,5-TIBA can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce an herbicidal effect.
  • 2,3,5-TIBA is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 140 g ai/ha or greater, such as 150 g ai/ha or greater, 200 g ai/ha or greater, 300 g ai/ha or greater, 400 g ai/ha or greater, 500 g ai/ha or greater, 600 g ai/ha or greater, 700 g ai/ha or greater, 750 g ai/ha or greater, 800 g ai/ha or greater, 900 g ai/ha or greater, 1000 g ai/ha or greater, 1100 g ai/ha or greater, 1200 g ai/ha or greater, 1250 g ai/ha or greater, 1300 g ai/ha or greater, 1400 g ai/ha or greater, 1500 g ai/ha or greater, 1600 g ai/ha or
  • compositions can include an inhibitor of a protoporphyrinogen oxidase (PPO), which is an enzyme involved in the biosynthesis of both heme and chlorophyll. It is believed that PPO inhibitors generate large amounts of singlet oxygen, which leads to the peroxidation of the lipids in cell membranes.
  • PPO protoporphyrinogen oxidase
  • PPO inhibitors include acifluorfen, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, chlomethoxyfen, cinidon, fluazolate, flufenpyr, flumiclorac, flumioxazin, fluoroglycofen, fluthiacet, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4- tetrahydropyrimidin
  • the PPO inhibitor herbicides or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent to the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the PPO inhibitor or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 0.5 grams active ingredient per hectare (g ai/ha) or more, such as 1 g ai/ha or more, 1.25 g ai/ha or more, 1.5 g ai/ha or more, 1.75 g ai/ha or more, 2 g ai/ha or more, 2.5 g ai/ha or more, 3 g ai/ha or more, 3.5 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/
  • the herbicidal composition contains a herbicidally effective amount of compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) acifluorfen, azafenidin, benzfendizone, bifenox, butafenacil, carfentrazone, chlomethoxyfen, cinidon, fluazolate, flufenpyr, flumiclorac, flumioxazin, fluoroglycofen, fluthiacet, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, agriculturally acceptable salts or esters thereof, or combinations
  • Acifluorfen Compositions and methods of the present disclosure can include acifluorfen or an agriculturally acceptable salt or ester thereof.
  • Acifluorfen as well as methods of preparing acifluorfen, are known in the art.
  • Acifluorfen shown below, is 5-[2-chloro-4- (trifluoromethyl)phenoxy]-2-nitrobenzoic acid. Its herbicidal activity is exemplified in Turner, J. A., Ed., The Pesticide Manual: A World Compendium, 17 th ed.; BCPC: Alton, Hampshire, UK, 2016 (hereafter “The Pesticide Manual”).
  • acifluorfen Exemplary uses include its use for post-emergence control of broadleaf weeds, with some control of grass weeds, in soybeans, peanuts, and rice.
  • Acifluorfen can be applied to the foliage and roots of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • acifluorfen is applied to the foliage and roots of undesirable vegetation in an amount of 100 g ai/ha or more, such as 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more
  • Azafenidin Compositions and methods of the present disclosure can include azafenidin or an agriculturally acceptable salt or ester thereof.
  • Azafenidin, as well as methods of preparing azafenidin, are known in the art.
  • Azafenidin, shown below, is 2-[2,4-dichloro-5-(2-propyn-1- yloxy)phenyl]-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one.
  • azafenidin is a herbicide that was evaluated by DuPont for use as a pre-emergence and, in mixtures, post-emergence control of annual and perennial weeds in citrus, grapes, olives, sugar cane, and other perennial crops.
  • Benzfendizone Compositions and methods of the present disclosure can include benzfendizone or an agriculturally acceptable salt or ester thereof. Benzfendizone, as well as methods of preparing benzfendizone, are known in the art.
  • Benzfendizone shown below, is methyl 2-[2- [[4-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)- pyrimidinyl]phenoxy]methyl]-5-ethylphenoxy]propanoate.
  • benzfendizone is a herbicide that was evaluated by FMC for post- emergence control of grass and broadleaf weeds in orchards and no-till situations, and also as a cotton defoliant and potato desiccant.
  • Bifenox Compositions and methods of the present disclosure can include bifenox or an agriculturally acceptable salt or ester thereof.
  • Bifenox as well as methods of preparing bifenox, are known in the art.
  • Bifenox shown below, is methyl 5-(2,4-dichlorophenoxy)-2- nitrobenzoate. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of bifenox include its use for pre-emergence, pre-plant incorporated, or directed post- emergence control of annual broadleaf weeds and some grass weeds in cereals, maize, sorghum, soybeans, rice, etc. Bifenox can be applied to the foliage, emerging shoots, and roots of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • bifenox is applied to the foliage, emerging shoots, and roots of undesirable vegetation in an amount of 50 g ai/ha or more, such as 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 125 g ai/ha or more, 150 g ai/ha or more, 175 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, 275 g ai/ha or more, 300 g ai/ha or more, 350 g ai/ha or more, 400 g ai/ha or more, 450 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more
  • Butafenacil Compositions and methods of the present disclosure can include butafenacil or an agriculturally acceptable salt or ester thereof.
  • Butafenacil as well as methods of preparing butafenacil, are known in the art.
  • Butafenacil shown below, is 1,1-dimethyl-2-oxo-2-(2- propenyloxy)ethyl-2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)- pyrimidinyl]benzoate. Its herbicidal activity is exemplified in The Pesticide Manual.
  • Carfentrazone Compositions and methods of the present disclosure can include carfentrazone or an agriculturally acceptable salt or ester thereof.
  • Carfentrazone, as well as methods of preparing carfentrazone, are known in the art.
  • Carfentrazone-ethyl shown below, is a commonly used ester form of carfentrazone with the structure ethyl ⁇ ,2-dichloro-5-[4- (difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]-4- fluorobenzenepropanoate. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of carfentrazone-ethyl include its use for post-emergence control of broadleaf weeds in cereals and for the desiccation of potatoes. Carfentrazone can be applied to the foliage of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • carfentrazone is applied to the foliage of undesirable vegetation in an amount of 0.5 g ai/ha or more, such as 0.6 g ai/ha or more, 0.8 g ai/ha or more, 1 g ai/ha or more, 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 22.5 g ai/ha or more, 25g ai/ha or more, 27.5 g ai/ha or
  • Chlomethoxyfen Compositions and methods of the present disclosure can include chlomethoxyfen or an agriculturally acceptable salt or ester thereof.
  • Chlomethoxyfen as well as methods of preparing chlomethoxyfen, are known in the art.
  • Chlomethoxyfen shown below, is 2,4- dichloro-1-(3-methoxy-4-nitrophenoxy)benzene. Its herbicidal activity is exemplified in The Pesticide Manual.
  • Exemplary uses of chlomethoxyfen include its use for pre-emergence control of annual weeds in transplanted rice, applied at 1.5-2.5 kg ai/ha.
  • Chlomethoxyfen can be applied to the leaves and stems of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • chlomethoxyfen is applied to the leaves and stems of undesirable vegetation in an amount of 250 g ai/ha or more, such as 275 g ai/ha or more, 300 g ai/ha or more, 350 g ai/ha or more, 400 g ai/ha or more, 450 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, or 1000 g ai/ha or
  • Cinidon Compositions and methods of the present disclosure can include cinidon or an agriculturally acceptable salt or ester thereof. Cinidon, as well as methods of preparing cinidon, are known in the art. Cinidon-ethyl, shown below, is a commonly used ester of cinidon with the structure ethyl (2Z)-chloro-3-[2-chloro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2- yl)phenyl]-2-propenoate. Its herbicidal activity is exemplified in The Pesticide Manual.
  • Cinidon can be applied to the foliage of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • cinidon is applied to the foliage of undesirable vegetation in an amount of 0.5 g ai/ha or more, such as 0.6 g ai/ha or more, 0.8 g ai/ha or more, 1 g ai/ha or more, 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g a
  • Fluazolate Compositions and methods of the present disclosure can include fluazolate or an agriculturally acceptable salt or ester thereof.
  • Fluazolate as well as methods of preparing fluazolate, are known in the art. Fluazolate, shown below, is 1-methylethyl 5-[4-bromo-1- methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-2-chloro-4-fluorobenzoate.
  • fluazolate is a herbicide under development for use as pre-emergence control of grasses and broadleaf weeds on cereals. Fluazolate can be applied to undesirable vegetation or applied to soil to prevent the emergence or growth of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • fluazolate is applied to undesirable vegetation or applied to soil to prevent the emergence or growth of undesirable vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more
  • Flufenpyr Compositions and methods of the present disclosure can include flufenpyr or an agriculturally acceptable salt or ester thereof.
  • Flufenpyr as well as methods of preparing flufenpyr, are known in the art.
  • Flufenpyr-ethyl shown below, is a commonly-used ester of flufenpyr, whose structure is ethyl [2-chloro-4-fluoro-5-[5-methyl-6-oxo-4-(trifluoromethyl)- 1(6H)-pyridazinyl]phenoxy]acetate. Its herbicidal activity is exemplified in The Pesticide Manual.
  • flufenpyr can be applied to the foliage of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • flufenpyr is applied to the foliage of undesirable vegetation in an amount of 0.5 g ai/ha or more, such as 0.6 g ai/ha or more, 0.8 g ai/ha or more, 1 g ai/ha or more, 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5
  • Flumiclorac Compositions and methods of the present disclosure can include flumiclorac-pentyl or an agriculturally acceptable salt or ester thereof.
  • Flumiclorac as well as methods of preparing flumiclorac, are known in the art.
  • Flumiclorac-pentyl shown below, is a commonly- used ester of flumiclorac, whose structure is pentyl 2-[2-chloro-4-fluoro-5-(1,3,4,5,6,7- hexahydro-1,3-dioxo-2H-isoindol-2-yl)-phenoxy]acetate. Its herbicidal activity is exemplified in The Pesticide Manual.
  • flumiclorac Exemplary uses include its use for pre- and post- emergence control of broadleaf weeds in maize and soybeans, applied at 30-60 g ai/ha. Flumiclorac can be applied to the foliage of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • flumiclorac is applied to the foliage of undesirable vegetation in an amount of 0.5 g ai/ha or more, such as 0.6 g ai/ha or more, 0.8 g ai/ha or more, 1 g ai/ha or more, 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 22.5 g ai/ha or more, 25g ai/ha or more, 27.5 g ai/ha or more, 30 g ai/ha or
  • Flumioxazin Compositions and methods of the present disclosure can include flumioxazin or an agriculturally acceptable salt or ester thereof.
  • Flumioxazin as well as methods of preparing flumioxazin, are known in the art. Flumioxazin, shown below, is 2-[7-fluoro-3,4-dihydro-3- oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione. Its herbicidal activity is exemplified in The Pesticide Manual.
  • flumioxazin examples include its use for pre-emergence control of annual broadleaf weeds and some annual grass weeds in soybeans, peanuts, orchards, vines, and other crops. Flumioxazin can be applied to the undesirable vegetation or applied to soil to prevent the emergence or growth of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • g ai/ha or more such as 60 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 220 g ai/ha or more,
  • Fluoroglycofen Compositions and methods of the present disclosure can include fluoroglycofen or an agriculturally acceptable salt or ester thereof.
  • Fluoroglycofen as well as methods of preparing fluoroglycofen, are known in the art.
  • Fluoroglycofen-ethyl shown below, is a commonly-used ester of fluoroglycofen, whose structure is carboxymethyl 5-[2-chloro-4- (trifluoromethyl)phenoxy]-2-nitrobenzoate. Its herbicidal activity is exemplified in The Pesticide Manual.
  • fluoroglycofen examples include its use for post-emergence control of broadleaf weeds and grass weeds in wheat, barley, oats, peanuts, rice, and soybeans. Fluoroglycofen thereof can be applied to the foliage or roots of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • fluoroglycofen is applied to the foliage or roots of undesirable vegetation in an amount of 0.5 g ai/ha or more, such as 0.6 g ai/ha or more, 0.8 g ai/ha or more, 1 g ai/ha or more, 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 22.5 g ai/ha or more, 25g ai/ha or more, 27.5 g ai/ha or more, 30
  • Fluthiacet Compositions and methods of the present disclosure can include fluthiacet or an agriculturally acceptable salt or ester thereof.
  • Fluthiacet as well as methods of preparing fluthiacet, are known in the art.
  • Fluthiacet-methyl shown below, is a commonly-used ester of fluthiacet, whose structure is methyl 2-[[2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H- [1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)amino]-phenyl]thio]acetate. Its herbicidal activity is exemplified in The Pesticide Manual.
  • fluthiacet-methyl examples include its use for post-emergence control of broadleaf weeds in maize and soybeans, applied at 4-15 g ai/ha. Fluthiacet can be applied to the foliage of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • fluthiacet is applied to the foliage of undesirable vegetation in an amount of 0.5 g ai/ha or more, such as 0.6 g ai/ha or more, 0.8 g ai/ha or more, 1 g ai/ha or more, 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 22.5 g ai/ha or more, 25g ai/ha or more, 27.5 g ai/ha or more, 30 g ai/
  • Fomesafen Compositions and methods of the present disclosure can include fomesafen or an agriculturally acceptable salt or ester thereof.
  • Fomesafen as well as methods of preparing fomesafen, are known in the art.
  • Fomesafen shown below, is 5-[2-chloro-4- (trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide. Its herbicidal activity is exemplified in The Pesticide Manual.
  • Exemplary uses of fomesafen include its use for early post-emergence control of broadleaf weeds in soybeans, applied at 200-400 g ai/ha.
  • Fomesafen can be applied to the foliage and roots of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • fomesafen is applied to the foliage and roots of undesirable vegetation in an amount of 100 g ai/ha or more, such as 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more,
  • Halosafen Compositions and methods of the present disclosure can include halosafen or an agriculturally acceptable salt or ester thereof.
  • Halosafen as well as methods of preparing halosafen, are known in the art.
  • Halosafen shown below, is 5-[2-chloro-6-fluoro-4- (trifluoromethyl)phenoxy]-N-(ethylsulfonyl)-2-nitrobenzamide.
  • halosafen is a herbicide that was evaluated by ICI Agrochemicals.
  • Lactofen Compositions and methods of the present disclosure can include lactofen or an agriculturally acceptable salt or ester thereof.
  • Lactofen as well as methods of preparing lactofen, are known in the art. Lactofen, shown below, is 2-ethoxy-1-methyl-2-oxoethyl 5-[2- chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of lactofen include its use for post-emergence control of broadleaf weeds cotton, soybeans, and snap beans, applied at 220 g ai/ha. Lactofen can be applied to the foliage of undesirable vegetation in an amount sufficient to induce an herbicidal effect.
  • lactofen is applied to the foliage of undesirable vegetation in an amount of 50 g ai/ha or more, such as 60 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 220 g ai/ha or more, 240 g ai/ha or more
  • Oxadiargyl Compositions and methods of the present disclosure can include oxadiargyl or an agriculturally acceptable salt or ester thereof.
  • Oxadiargyl as well as methods of preparing oxadiargyl, are known in the art.
  • Oxadiargyl, shown below, is 3-[2,4-dichloro-5-(2-propyn-1- yloxy)phenyl]-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one. Its herbicidal activity is exemplified in The Pesticide Manual.
  • Exemplary uses of oxadiargyl include its use for pre- and early post-emergence control of broadleaf weeds, grass weeds, and annual sedge weeds in rice, applied at 50-150 g ai/ha, sunflowers, potatoes, vegetables, and sugar cane, applied at 300- 500 g ai/ha, and fruit and citrus, applied at 500-1500 g ai/ha.
  • Oxadiargyl thereof can be applied to undesirable vegetation or applied to soil or water to prevent the emergence or growth of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • oxadiargyl is applied to undesirable vegetation or applied to soil or water to prevent the emergence or growth of undesirable vegetation in an amount of 25 g ai/ha or more, such as 40 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 80 g ai/ha or more, 100 g ai/ha or more, 125 g ai/ha or more, 150 g ai/ha or more, 175 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, 275 g ai/ha or more, 300 g ai/ha or more, 350 g ai/ha or more, 400 g ai/ha or more, 450 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600
  • Oxadiazon Compositions and methods of the present disclosure can include oxadiazon or an agriculturally acceptable salt or ester thereof.
  • Oxadiazon as well as methods of preparing oxadiazon, are known in the art.
  • Oxadiazon shown below, is 3-[2,4-dichloro-5-(1- methylethoxy)phenyl]-5-(1,1-dimethylethyl)-1,3,4-oxadiazol-2(3H)-one. Its herbicidal activity is exemplified in The Pesticide Manual.
  • Exemplary uses of oxadiazon include: its use for pre-emergence control of bindweed, annual broadleaf weeds, and grass weeds; post- emergence control of bindweed and annual broadleaf weeds in carnations, roses, ornamental trees and shrubs, tree fruit, bush fruit, citrus, vines, hops, cotton, rice, soybeans, sunflowers, onions, and turf; and pre-emergent or post-emergent control of annual broadleaf and grass weeds in orchards and vineyards.
  • Oxadiazon can be applied to undesirable vegetation or applied to soil or water to prevent the emergence or growth of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • oxadiazon is applied to undesirable vegetation or applied to soil or water to prevent the emergence or growth of undesirable vegetation in an amount of 250 g ai/ha or more, such as 275 g ai/ha or more, 300 g ai/ha or more, 350 g ai/ha or more, 400 g ai/ha or more, 450 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, or 950 g ai/ha or more; in an amount of 1001 g ai/ha or less, such as 1000 g ai/ha or less, 950 g
  • Oxyfluorfen Compositions and methods of the present disclosure can include oxyfluorfen or an agriculturally acceptable salt or ester thereof.
  • Oxyfluorfen, as well as methods of preparing oxyfluorfen, are known in the art.
  • Oxyfluorfen, shown below, is 2-chloro-1-(3-ethoxy-4- nitrophenoxy)-4-(trifluoromethyl)benzene. Its herbicidal activity is exemplified in The Pesticide Manual.
  • Exemplary uses of oxyfluorfen include its use for pre- and post-emergence control of annual broadleaf and grass weeds in tree fruit, citrus, vines, nuts, cereals, maize, soybeans, peanuts, rice, cotton, bananas, peppermint, onions, garlic, ornamentals, and conifer seedbeds, applied at 250-2000 g ai/ha.
  • Oxyfluorfen can be applied to the foliage and shoots of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • oxyfluorfen is applied to the foliage and shoots of undesirable vegetation in an amount of 50 g ai/ha or more, such as 75 g ai/ha or more, 100 g ai/ha or more, 125 g ai/ha or more, 150 g ai/ha or more, 175 g ai/ha or more, 200 g ai/ha or more, 250 g ai/ha or more, 300 g ai/ha or more, 350 g ai/ha or more, 400 g ai/ha or more, 450 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 900 g ai/ha or more, or 950 g ai/ha or more;
  • Pentoxazone Compositions and methods of the present disclosure can include pentoxazone or an agriculturally acceptable salt or ester thereof.
  • Pentoxazone as well as methods of preparing pentoxazone, are known in the art.
  • Pentoxazone shown below, is 3-(4-chloro-5- (cyclopentyloxy)-2-fluorophenyl]-5-(1-methylethylidene)-2,4-oxazolidinedione. Its herbicidal activity is exemplified in The Pesticide Manual.
  • Exemplary uses of pentoxazone include its use for pre- and post-emergence control of Echinochloa spp. and Monochoria vaginalis in paddy rice.
  • Pentoxazone thereof can be applied to undesirable vegetation or applied to soil or water to prevent the emergence or growth of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • pentoxazone is applied to undesirable vegetation or applied to soil or water to prevent the emergence or growth of undesirable vegetation in an amount of 50 g ai/ha or more, such as 60 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or
  • Profluazol Compositions and methods of the present disclosure can include profluazol or an agriculturally acceptable salt or ester thereof.
  • Profluazol as well as methods of preparing profluazol, are known in the art.
  • Profluazol shown below, is 1-chloro-N-[2-chloro-4-fluoro- 5-[(6S,7aR)-6-fluorotetrahydro-1,3-dioxo-1H-pyrrolo[1,2-c]imidazol-2(3H)- yl]phenyl]methanesulfonamide.
  • profluazol is a herbicide developed by DuPont.
  • Pyraclonil Compositions and methods of the present disclosure can include pyraclonil or an agriculturally acceptable salt or ester thereof.
  • Pyraclonil as well as methods of preparing pyraclonil, are known in the art.
  • Pyraclonil shown below, is 1-(3-chloro-4,5,6,7- tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-[methyl-2-propynylamino]-1H-pyrazole-4- carbonitrile. According to the online edition of The Pesticide Manual, pyraclonil is being evaluated for pre-emergence control of broadleaf and sedge weeds in rice.
  • Pyraclonil can be applied to undesirable vegetation or applied to soil or water to prevent the emergence or growth of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • pyraclonil is applied to undesirable vegetation or applied to soil or water to prevent the emergence or growth of undesirable vegetation in an amount of 5 g ai/ha or more, such as 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 22.5 g ai/ha or more, 25g ai/ha or more, 27.5 g ai/ha or more, 30 g ai/ha or more, 32.5 g ai/ha or more, 35 g ai/ha
  • Pyraflufen Compositions and methods of the present disclosure can include pyraflufen or an agriculturally acceptable salt or ester thereof.
  • Pyraflufen as well as methods of preparing pyraflufen-ethyl, are known in the art.
  • Pyraflufen-ethyl shown below, is a commonly used ester of pyraflufen, whose structure is ethyl 2-chloro-5-[4-chloro-5-(difluoromethoxy)-1- methyl-1H-pyrazol-3-yl]-4-fluorophenoxyacetate. Its herbicidal activity is exemplified in The Pesticide Manual.
  • Exemplary uses of pyraflufen include its use for post-emergence control of broadleaf weeds in cereals. Pyraflufen can be applied to the foliage of undesirable vegetation in an amount sufficient to induce a herbicidal effect. In some aspects, pyraflufen is applied to the foliage of undesirable vegetation in an amount of 0.5 g ai/ha or more, such as 0.6 g ai/ha or more, 0.8 g ai/ha or more, 1 g ai/ha or more, 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5
  • Saflufenacil Compositions and methods of the present disclosure can include saflufenacil or an agriculturally acceptable salt or ester thereof.
  • Saflufenacil as well as methods of preparing saflufenacil, are known in the art.
  • Saflufenacil shown below, is 2-chloro-5-[3,6-dihydro-3- methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[[methyl(1- methylethyl)-amino]sulfonyl]benzamide. Its herbicidal activity is exemplified in The Pesticide Manual.
  • saflufenacil examples include: pre-emergence control of broadleaf weeds in maize and sorghum; pre-plant foliar burn-down in soybeans, cereals, cotton, and legumes; and post-directed foliar burn-down in tree fruit and nuts. Saflufenacil can be applied to the foliage or roots of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • saflufenacil is applied to the foliage or roots of undesirable vegetation in an amount of 0.5 g ai/ha or more, such as 0.6 g ai/ha or more, 0.8 g ai/ha or more, 1 g ai/ha or more, 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 22.5 g ai/ha or more, 25g ai/ha or more, 27.5 g ai/ha or more, 30
  • Sulfentrazone Compositions and methods of the present disclosure can include sulfentrazone or an agriculturally acceptable salt or ester thereof.
  • Sulfentrazone as well as methods of preparing sulfentrazone, are known in the art.
  • Sulfentrazone shown below, is N-[2,4-dichloro- 5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl]phenyl]-methane- sulfonamide. Its herbicidal activity is exemplified in The Pesticide Manual.
  • Exemplary uses of sulfentrazone include its use for pre-plant incorporated or pre-emergence control of annual broadleaf weeds, some grass weeds, and Cyperus spp. in soybeans, sugar cane, and tobacco. Sulfentrazone can be applied to the foliage and roots of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • sulfentrazone is applied to the foliage and roots of undesirable vegetation in an amount of 100 g ai/ha or more, such as 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or
  • Thidiazimin Compositions and methods of the present disclosure can include thidiazimin or an agriculturally acceptable salt or ester thereof.
  • Thidiazimin as well as methods of preparing thidiazimin, are known in the art.
  • Thidiazimin shown below, is 6-[(Z)-(6,7-dihydro-6,6- dimethyl-3H,5H-pyrrolo[2,1-c][1,2,4]thiadiazol-3-ylidene)amino]-7-fluoro-4-(2-propyn-1- yl)-2H-1,4-benzoxazin-3(4H)-one. Its herbicidal activity is exemplified in The Pesticide Manual.
  • thidiazimin Exemplary uses include its use for post-emergence control of broadleaf weeds in winter cereals, applied at 20-40 g ai/ha. Thidiazimin can be applied to the foliage of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • thidiazimin thereof is applied to the foliage of undesirable vegetation in an amount of 0.5 g ai/ha or more, such as 0.6 g ai/ha or more, 0.8 g ai/ha or more, 1 g ai/ha or more, 2 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 22.5 g ai/ha or more, 25g ai/ha or more, 27.5 g ai/ha or more, 30 g a
  • Tiafenacil Compositions and methods of the present disclosure can include tiafenacil or an agriculturally acceptable salt or ester thereof.
  • Tiafenacil as well as methods of preparing tiafenacil, are known in the art.
  • Tiafenacil shown below, is methyl N-[2-[[2-chloro-5-[3,6- dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]thio]-1- oxopropyl-ß-alaninate. Its herbicidal activity is exemplified in The Pesticide Manual.
  • Exemplary uses of tiafenacil include its use for none-selective post-emergence burn down control in row crops and permanent crops. Tiafenacil can be applied to the foliage and roots of undesirable vegetation in an amount sufficient to induce a herbicidal effect.
  • tiafenacil is applied to the foliage and roots of undesirable vegetation in an amount of 10 g ai/ha or more, such as 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, or 75 g ai/ha or more, 100 g ai/ha or more, 125 g ai/ha or more, 150 g ai/ha or more, 175 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, or 275 g ai/ha or more
  • Trifludimoxazin Compositions and methods of the present disclosure can include mixtures of the compounds of Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and trifludimoxazin, a PPO inhibitor.
  • Exemplary uses of trifludimoxazin can include pre- and/or post-emergent control of broadleaf and grass weeds. It can be applied by aircraft on citrus fruits, pome fruits, cereal grain (except rice), tree nuts, peanuts, and foliage of legume vegetables.
  • Non-agricultural use sites include tree plantations, industrial landscaping, native grass openings, and conifer and hardwood plantations.
  • a composition comprising compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof) may be mixed with or applied in combination with (b) a protoporphyrinogen oxidase (PPO) inhibitors, an agriculturally acceptable salt or ester thereof, or mixtures thereof.
  • PPO protoporphyrinogen oxidase
  • (a) and (b) are used in an amount sufficient to induce an enhanced herbicidal effect (e.g., increased damage or injury to undesirable vegetation) while still showing good crop compatibility (e.g., no increased damage to crops or minimal increased damage or injury to crops) when compared to the individual application of the herbicidal compounds (a) or (b).
  • the damage or injury to undesirable vegetation caused by the compositions and methods disclosed herein is evaluated using a scale from 0% to 100%, when compared with the untreated control vegetation, wherein 0% indicates no damage to the undesirable vegetation and 100% indicates complete destruction of the undesirable vegetation.
  • the joint action of (a) the compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) the PPO inhibitor herbicide or an agriculturally acceptable salt or ester thereof results in enhanced herbicidal effect against undesirable vegetation, even at application rates below those typically used for the herbicide to have a herbicidal effect on its own.
  • compositions and methods disclosed herein can, based on the individual components, be used at lower application rates to achieve a herbicidal effect comparable to the effect produced by the individual components at normal application rates.
  • the weight ratio of (a) the compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof) (in g ae/ha) to (b) the PPO inhibitor herbicide or an agriculturally acceptable salt or ester thereof (in g ai/ha) can be 1:2000 or more, such as 1:1900 or more, 1:1500 or more, 1:1000 or more, 1: 900 or more, 1:800 or more, 1:700 or more, 1:600 or more, 1:500 or more, 1:400 or more, 1:300 or more, 1:200 or more, 1:100 or more, 1:90 or more, 1:80 or more, 1:70 or more, 1:60 or more, 1:50 or more, 1:40 or more, 1:30 or more, 1:24 or more, 1:20
  • the active ingredients in the compositions disclosed herein consist of compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof) and (b) a PPO inhibitor herbicide or an agriculturally acceptable salt or ester thereof.
  • the composition may include other components, such as safeners or adjuvants, but does not include a herbicidal active ingredient in addition to (a) and (b).
  • (a) and (b), independently, can be employed in a purity of from 90% to 100% (e.g., from 95% to 100%) according to nuclear magnetic resonance (NMR) spectroscopy.
  • NMR nuclear magnetic resonance
  • the compositions can include a phytoene desaturase (PDS) inhibitor herbicide or agriculturally acceptable salt or ester thereof.
  • PDS inhibitors block carotenoid biosynthesis by inhibition of phytoene desaturase, a key enzyme in the carotenoid biosynthesis pathway. An absence of carotenoids leads to destruction of membrane fatty acid and chlorophyll by excessive energy.
  • PDS inhibitors include, but are not limited to, beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, and picolinafen.
  • the composition can include a PDS inhibitor herbicide selected from the group consisting of beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, agriculturally acceptable salts and esters thereof, and combinations thereof.
  • PDS inhibitor herbicide or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the PDS inhibitor herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 12.5 gram active ingredient per hectare (g ai/ha) or more, such as 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or
  • the composition contains compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) diflufenican, flurtamone, picolinafen, or mixtures thereof.
  • Beflubutamid In some aspects, the PDS inhibitor herbicide can comprise beflubutamid or an agriculturally acceptable salt or ester thereof. Beflubutamid, shown below, is 2-[4-fluoro-3- (trifluoromethyl)phenoxy]-N-(phenylmethyl)butanamide. Its herbicidal activity is exemplified in Tomlin, C. D. S., Ed.
  • beflubutamid A World Compendium, 17 th ed.; BCPC: Alton, 2016 (hereafter “The Pesticide Manual, Seventeenth Edition, 2016”).
  • Exemplary uses of beflubutamid include its use alone, and in mixture with isoproturon, for pre- and early post- emergence control of broadleaf weeds, such as Veronica persica, Lamium amplexicaule and Viola arvensis, in wheat and barley.
  • Beflubutamid can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • beflubutamid is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 25 g ai/ha or more, such as 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 42.5 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more,160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/
  • the PDS inhibitor herbicide can comprise diflufenican or an agriculturally acceptable salt or ester thereof.
  • Diflufenican as well as methods of preparing diflufenican, are known in the art.
  • Diflufenican shown below, is N-(2,4-difluorophenyl)-2-[3- (trifluoromethyl)phenoxy]-3-pyridinecarboxamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of diflufenican include its use as a selective contact and residual herbicide that is used pre- and early post-emergence in autumn-sown wheat and barley to control grass and broadleaf weeds.
  • Diflufenican can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • diflufenican is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 105 g ai/ha or more, 110 g ai/ha or more, 115 g ai/ha or more, 120 g ai/ha or more,
  • the PDS inhibitor herbicide can comprise fluridone or an agriculturally acceptable salt or ester thereof.
  • Fluridone shown below, is 1-methyl-3-phenyl- 5-[3-(trifluoromethyl)- phenyl]-4(1H)-pyridinone. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016.
  • fluridone examples include its use as an aquatic herbicide for control of most submerged and emerged aquatic plants (including Utricularia spp., Ceratophyllum demersum, Elodea canadensis, Myriophyllum spp., Najas guadalupensis, Potamogeton spp., Hydrilla verticillata and Panicum purpurascens) in ponds, lakes, reservoirs, irrigation ditches.
  • CH 3 N Fluridone can be applied to vegetation or an area adjacent the vegetation or applied to water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • fluridone can be applied to water to prevent the emergence or growth of vegetation in an amount of 200 g ai/ha or more, such as 220 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 280 g ai/ha or more, 300 g ai/ha or more, 320 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, 400 g ai/ha or more, 450 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha
  • the PDS inhibitor herbicide can comprise flurochloridone or an agriculturally acceptable salt or ester thereof.
  • Flurochloridone shown below, is 3-chloro-4- (chloromethyl)-1-[3-(trifluoromethyl)phenyl]-2-pyrrolidinone. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of flurochloridone include its use for pre-emergence control of a wide range of broadleaf and grass weeds in sunflowers, carrots and other umbelliferous crops, winter wheat, winter rye, and potatoes.
  • Flurochloridone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • flurochloridone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 200 g ai/ha or more, such as 220 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 280 g ai/ha or more, 300 g ai/ha or more, 320 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, 400 g ai/ha or more, 450 g ai/ha or more, 500 g ai/
  • the PDS inhibitor herbicide can comprise flurtamone or an agriculturally acceptable salt or ester thereof.
  • Flurtamone shown below, is ( ⁇ )-5- (methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]-3(2H)-furanone. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of flurtamone include its use for pre-plant incorporated, pre-emergence or post emergence control of broadleaf and some grass weeds in small grains, peanuts, cotton, peas and sunflowers.
  • Flurtamone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • flurtamone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 40 g ai/ha or more, such as 42.5 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more,160 g ai/ha or more, 170 g
  • the PDS inhibitor herbicide can comprise norflurazon or an agriculturally acceptable salt or ester thereof.
  • Norflurazon shown below, is 4-chloro-5- (methylamino)-2-[3-(trifluoromethyl)phenyl]-3(2H)-pyridazinone. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of norflurazon include its use for pre-emergence control of grasses and sedges, including Digitaria spp. (crabgrasses), Echinochloa spp. (barnyard grasses), Setaria spp.
  • weeds such as Sida spinosa (prickly sida), Portulaca oleracea (purslane), Salsola spp. (Indian thistle), and Capsella bursa- pastoris (shepherd’s purse), in cotton, soybeans, peanuts, hops, orchards, ornamentals, and industrial areas.
  • Norflurazon can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • norflurazon is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 500 g ai/ha or more, such as 550 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g
  • the PDS inhibitor herbicide can comprise picolinafen or an agriculturally acceptable salt or ester thereof.
  • Picolinafen shown below, is N-(4- fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]-2-pyridinecarboxamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of picolinafen include its use as a post-emergence herbicide either alone or in mixtures for broad- spectrum weed control in cereals.
  • Picolinafen can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • picolinafen is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 12.5 g ai/ha or more, such as 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 22.5 g ai/ha or more, 25 g ai/ha or more, 27.5 g ai/ha or more, 30 g ai/ha or more, 32.5 g ai/ha or more, 35 g ai/ha or more, 37.5 g ai/ha or more, 40 g ai/ha or more, 42.5 g ai/ha or more, 45 g ai/ha or more, 47.5 g ai/ha or more, 50 g ai/ha or more, 52.5 g ai/ha or more, 55 g ai/ha or more, 57.5 g ai/
  • compositions can include glyphosate, glufosinate, an agriculturally acceptable salt thereof, or mixtures thereof.
  • Glyphosate In some aspects, compositions and methods of the present disclosure can include glyphosate or an agriculturally acceptable salt thereof. Glyphosate, as well as methods of preparing glyphosate, are known in the art. Glyphosate, shown below, is N- (phosphonomethyl)glycine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016.
  • Exemplary uses of glyphosate include its use for control of annual and perennial grasses and broadleaf weeds, particularly in crops that have been genetically modified to be tolerant of glyphosate.
  • Exemplary chemical forms of glyphosate include, but are not limited to, for example, glyphosate potassium salt, glyphosate sodium salt, glyphosate monoammonium salt, glyphosate diammonium salt, glyphosate isopropylamine (IPA) salt, glyphosate monoethanolamine (MEA) salt, glyphosate monomethylamine (MMA) salt, and glyphosate dimethylamine (DMA) salt.
  • IPA glyphosate potassium salt
  • MEA glyphosate monoethanolamine
  • MMA glyphosate monomethylamine
  • DMA glyphosate dimethylamine
  • glyphosate salt or salt of glyphosate generally refers to the reaction product of glyphosate with a moiety that can act as a base. Typically, the reaction is an acid-base reaction. Glyphosate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • glyphosate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 25 g ai/ha or more, such as 30 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 105 g ai/ha or more, 110 g ai/ha or more, 115 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 135 g ai/ha or more, 140
  • compositions and methods of the present disclosure can include glufosinate or an agriculturally acceptable salt thereof.
  • Glufosinate shown below, is 2-amino- 4-(hydroxy(methyl)phosphinyl)butanoic acid. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of glufosinate include its use for control of annual and perennial grasses and broadleaf weeds, particularly in crops that have been genetically modified to be tolerant of glufosinate.
  • glufosinate-ammonium which is also known as 2-amino-4-(hydroxy(methyl)phosphinyl)butanoic acid ammonium salt, and which has the following structure: .
  • Glufosinate-ammonium is registered for controlling a wide variety of broad-leaved weeds and grasses particularly in glufosinate-tolerant crops like canola, maize, soybean, rice, cotton, and sugar beet.
  • glufosinate salt or salt of glufosinate generally refers to the reaction product of glufosinate with a moiety that can act as a base. Typically, the reaction is an acid-base reaction.
  • glufosinate Other chemical forms of glufosinate include bilanafos, also known as bialaphos, which has the following structure: .
  • Bilanafos also can be used in the salt form such as bilanafos sodium. Exemplary uses are described in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses include its use to control annual and perennial broadleaf weeds and grasses.
  • Glufosinate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • glufosinate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 25 g ai/ha or more, such as 50 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 90 g ai/ha or more,100 g ai/ha or more, 112.5 g ai/ha or more, 125 g ai/ha or more, 150 g ai/ha or more, 175 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, 275 g ai/ha or more, 300 g ai/ha or more, 325 g ai/ha or more, 350 g ai/ha or more, 375 g ai/ha or more, 400 g ai/ha or
  • the compositions can include a photosystem II (PS II) inhibitor herbicide or agriculturally acceptable salt or ester thereof.
  • Photosystem II inhibitors inhibit photosynthesis by binding to the photosystem II complex in the chloroplast.
  • photosystem II inhibitors include phenylcarbamate herbicides, pyridazinone herbicides, triazolinone herbicides, triazine herbicides, urea herbicides, uracil herbicides, amide herbicides, nitrile herbicides, and phenylpyridazine herbicides.
  • the composition can include a PS II inhibitor herbicide selected from the group consisting of ametryne, amicarbazone, atrazine, bentazone, bromacil, bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, ethiozin, fenuron, fluometuron, hexazinone, iodobonil, ioxynil, isocil, isomethiozin, isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobromuron, metoxuron, metribuzin, monolinuron, neburon, pentanochlor, phenmedipham, prometon, prometryn
  • the PS II inhibitor herbicide or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the PS II inhibitor herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 5 grams active ingredient per hectare (g ai/ha) or more, such as 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more,
  • the photosystem II inhibitor or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of from 30-1000 g ai/ha.
  • the composition contains compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) ametryne, amicarbazone, atrazine, bentazone, bromacil, bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, ethiozin, fenuron, fluometuron, hexazinone, iodobonil, ioxynil, isocil, isomethiozin, isoproturon, isouron, kar
  • the PS II inhibitor herbicide can comprise ametryn or an agriculturally acceptable salt or ester thereof.
  • Ametryn shown below, is N 2 -ethyl-N 4 - isopropyl-6-(methylthio)-1,3,4-triazine-2,4-diamine. Its herbicidal activity is exemplified in Tomlin, C. D. S., Ed. The Pesticide Manual: A World Compendium, 17 th ed.; BCPC: Alton, 2016 (hereafter “The Pesticide Manual, Seventeenth Edition, 2016”).
  • Exemplary uses of ametryn include its use for pre- and early post-emergence control of annual grass and broadleaf weeds in pineapples, sugar cane, maize, bananas, cassava, sisal, and orchards.
  • Ametryn can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • ametryn is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2000 g ai/ha or more, such as 2100 g ai/ha or more, 2200 g ai/ha or more, 2300 g ai/ha or more, 2400 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2700 g ai/ha or more, 2800 g ai/ha or more, 2900 g ai/ha or more, 3000 g ai/ha or more, 3100 g ai/ha or more, 3200 g ai/ha or more, 3300 g ai/ha or more, 3400 g ai/ha or more, 3500 g ai/ha or more, 3600 g ai/ha or more, 3700 g ai/ha or more, 3
  • the PDS inhibitor herbicide can comprise amicarbazone or an agriculturally acceptable salt or ester thereof.
  • Amicarbazone shown below, is 4-amino-N-tert- butyl-4,5-dihydro-3-isopropyl-5-oxo-1H-1,2,4-triazole-1-carboxamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of amicarbazone include its use for pre-emergence control of annual broadleaf weeds in maize, pre- and post-emergence control of annual broadleaf and grass weeds in sugar cane, and post- emergence control of annual broadleaf and grass weeds in turf, and conifers.
  • Amicarbazone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • amicarbazone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 g ai/ha or more, such as 105 g ai/ha or more, 110 g ai/ha or more, 115 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 135 g ai/ha or more, 140 g ai/ha or more, 145 g ai/ha or more, 150 g ai/ha or more, 155 g ai/ha or more, 160 g ai/ha or more, 165 g ai/ha or more, 170 g ai/ha or more
  • the PDS inhibitor herbicide can comprise atrazine or an agriculturally acceptable salt or ester thereof.
  • Atrazine shown below, is 6-chloro-N 2 -ethyl-N 4 - isopropyl-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of atrazine include its use as a pre- and post-emergence control of annual broadleaf and grass weeds in maize, sorghum, sugar cane, pineapples, chemical fallow, grassland, macadamia nuts, conifers, and industrial weed control.
  • Atrazine can be applied to vegetation or an area adjacent the vegetation or applied to water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • atrazine can be applied to water to prevent the emergence or growth of vegetation in an amount of 300 g ai/ha or more, such as 320 g ai/ha or more, 340 g ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, 420 g ai/ha or more, 440 g ai/ha or more, 460 g ai/ha or more, 480 g ai/ha or more, 500 g ai/ha or more, 525 g ai/ha or more, 550 g ai/ha or more, 575 g ai/ha or more, 600 g ai/ha or more, 625 g ai/ha or more, 650 g ai/ha or more
  • the PDS inhibitor herbicide can comprise bentazone or an agriculturally acceptable salt or ester thereof.
  • Bentazone shown below, is 3-isopropyl-1H- 2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of bentazone include its use for post-emergence control of broadleaf weeds in winter and spring cereals, peanuts, maize, peas, beans, rice, and soybeans. Bentazone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • bentazone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 100 g ai/ha or more, 150 g ai/ha or more, 200 g ai/ha or more, 250 g ai/ha or more, 300 g ai/ha or more, 350 g ai/ha or more, 400 g ai/ha or more, 450 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000
  • the PDS inhibitor herbicide can comprise bromacil or an agriculturally acceptable salt or ester thereof.
  • Bromacil shown below, is 5-bromo-3-sec-butyl- 6-methyluracil. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of bromacil include its use for pre- and post-emergence control of broadleaf and grass weeds in citrus, pineapple, and total weed and brush control in non-crop lands. Bromacil can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • bromacil is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1500 g ai/ha or more, such as 1600 g ai/ha or more, 1750 g ai/ha or more, 2000 g ai/ha or more, 2250 g ai/ha or more, 2500 g ai/ha or more, 2750 g ai/ha or more, 3000 g ai/ha or more, 3500 g ai/ha or more, 4000 g ai/ha or more, 4500 g ai/ha or more, 5000 g ai/ha or more, 6000 g ai/ha or more, 7000 g ai/ha or more, 7500 g ai/ha or more, 8000 g ai/ha or more, 9000 g ai/ha or more, 10,000 g ai/ha or more, 11,000 g ai/
  • the PDS inhibitor herbicide can comprise bromofenoxim or an agriculturally acceptable salt or ester thereof.
  • Bromofenoxim shown below, is 3,5-dibromo- 4-hydroxybenzaldehyde 2,4-dinitrophenyloxime. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of bromofenoxim include its use for post-emergence control of many annual broadleaf weeds in cereals, maize, grass-seed crops, grassland, and new-seeded turf.
  • Bromofenoxim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • bromofenoxim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1000 g ai/ha or more, such as 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more,1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more,1400 g ai/ha or more, 1450 g ai/ha or more,1500 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1750 g ai/ha or more,1800
  • the PDS inhibitor herbicide can comprise bromoxynil or an agriculturally acceptable salt or ester thereof.
  • Bromoxynil shown below, is 3,5-dibromo-4- hydroxbenzonitrile. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of bromoxynil include its use as in post-emergence control of annual broadleaf weeds in cereals, ryegrass seed crops, turf and non-crop land, maize, and sorghum. Bromoxynil can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • bromoxynil is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/
  • the PS-II inhibitor herbicide can comprise chlorbromuron or an agriculturally acceptable salt or ester thereof.
  • Chlorbromuron shown below, is 3-(4-bromo-3- chlorophenyl)-1-methoxy-1-methylurea.
  • chlorbromuron Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of chlorbromuron include pre-emergence use on carrots, peas, potatoes, soybeans, and sunflowers. Chlorbromuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • chlorbromuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1000 g ai/ha or more, such as 1100 g ai/ha or more, 1200 g ai/ha or more, 1300 g ai/ha or more, 1400 g ai/ha or more, 1500 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1800 g ai/ha or more, 1900 g ai/ha or more, 2000 g ai/ha or more, 2100 g ai/ha or more, 2200 g ai/ha or more, 2300 g ai/ha or more, 2400 g ai/ha or more, or 2450 g ai/ha or more; in an amount of 2500 g ai/ha or less, such as 2450 g ai/ha or less
  • the PS-II inhibitor herbicide can comprise chloridazon or an agriculturally acceptable salt or ester thereof.
  • Chloridazon shown below, is 5-amino-4-chloro- 2-phenylpyridazin-3(2H)-one. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of chloridazon include its use for pre- and post- emergence or pre-plant control of annual broadleaf weeds in sugar beets, fodder beets, and beetroot.
  • Chloridazon can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • chloridazon is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1300 g ai/ha or more, such as 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1550 g ai/ha or more, 1600 g ai/ha or more, 1650 g ai/ha or more, 1700 g ai/ha or more, 1750 g ai/ha or more, 1800 g ai/ha or more, 1850 g ai/ha or more, 1900 g ai/ha or more, 1950 g ai/ha or more, 2000 g ai
  • the PS-II inhibitor herbicide can comprise chlorotoluron or an agriculturally acceptable salt or ester thereof.
  • Chlorotoluron shown below, is 3-(3-chloro-p- tolyl)-1,1-dimethylurea. Its herbicidal activity is exemplified in the online edition of The Pesticide Manual. Exemplary uses of chlorotoluron include its use for pre- and post- emergence control of many broadleaf and grass weeds in winter cereals. Chlorotoluron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • chlorotoluron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1500 g ai/ha or more, such as 1550 g ai/ha or more, 1600 g ai/ha or more, 1650 g ai/ha or more, 1700 g ai/ha or more, 1750 g ai/ha or more, 1800 g ai/ha or more, 1850 g ai/ha or more, 1900 g ai/ha or more, 1950 g ai/ha or more, 2000 g ai/ha or more, 2050 g ai/ha or more, 2100 g ai/ha or more, 2150 g ai/ha or more, 2200 g ai/ha or more, 2240 g ai/ha or more, 2250 g ai/ha or more, 2300 g ai/ha or more, 2350 g
  • the PS-II inhibitor herbicide can comprise chloroxuron or an agriculturally acceptable salt or ester thereof.
  • Chloroxuron shown below, is 3-[4-(4- chlorophenoxy)phenyl]-1,1-dimethylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016.
  • chloroxuron examples include its use for pre- and post-emergence control of annual broadleaf weeds and some grasses in peas, beans, carrots, celery, celeriac, onions, leeks, garlic, chives, fennel, parsley, dill, tomatoes, cucurbits, soybeans, strawberries, fruit trees, ornamentals, and conifers, and control of mosses in ornamental and sports turf, on paths and non-crop lands, and in glass houses.
  • Chloroxuron may be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount from 1 kg/ha to 4 kg/ha.
  • the PS-II inhibitor herbicide can comprise cyanazine or an agriculturally acceptable salt or ester thereof.
  • Cyanazine is 2-(4-chloro-6-(ethylamino)-1,3,5- triazin-2-ylamino)-2-methylpropiononitrile. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of cyanazine include its use for pre- or post-emergence control of grass and broadleaf weeds in broad beans, maize, peas, barley, wheat, cotton, oilseed rape, forestry, potatoes, soybeans, and sugar cane.
  • Cyanazine can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • cyanazine is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 250 g ai/ha or more, such as 260 g ai/ha or more, 270 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/ha or more, 310 g ai/ha or more, 320 g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 370 g ai/ha or more, 380 g ai/ha or more, 390 g ai/
  • the PS-II inhibitor herbicide can comprise desmedipham or an agriculturally acceptable salt or ester thereof.
  • Desmedipham shown below, is 3- ethoxycarbonylaminophenyl phenylcarbamate. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of desmedipham include its use in post-emergence control of broadleaf weeds in beets. Desmedipham can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • desmedipham is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 300 g ai/ha or more, such as 310 g ai/ha or more, 320 g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 370 g ai/ha or more, 380 g ai/ha or more, 390 g ai/ha or more, 400 g ai/ha or more, 410 g ai/ha or more, 420 g ai/ha or more, 430 g ai/ha or more, 440 g ai/ha or more, 450 g ai/ha or more, 460 g ai/ha or more, 480 g ai/ha or more, 500 g ai/
  • the PS-II inhibitor herbicide can comprise desmetryn or an agriculturally acceptable salt or ester thereof.
  • Desmetryn shown below, is N 2 -isopropyl-N 4 - methyl-6-methylthio-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of desmetryn include its use for pre-emergence control of fat-hen and other annual broadleaf weeds and some grasses in brassicas (except cauliflower and broccoli), herbs, onions, leeks, and conifer seedbeds.
  • Desmetryn can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • desmetryn is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 200 g ai/ha or more, such as 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/ha or more, 310 g ai/ha or more, 320 g ai/ha or more, 330 g ai/ha or
  • the PS-II inhibitor herbicide can comprise dimefuron or an agriculturally acceptable salt or ester thereof.
  • Dimefuron shown below, is 3-[4-(5-tert-butyl- 2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl)-3-chlorophenyl]-1,1-dimethylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016.
  • Dimefuron is used for pre- and post-emergence control of difficult annual broadleaf weeds (e.g., Stellaria media, Chamomilla, and Matricaria spp.) in beans, certain cereals, cotton, peanuts, dormant alfalfa, oilseed rape, and peas. Dimefuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • difficult annual broadleaf weeds e.g., Stellaria media, Chamomilla, and Matricaria spp.
  • Dimefuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • dimefuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 200 g ai/ha or more, such as 225 g ai/ha or more, 250 g ai/ha or more, 275 g ai/ha or more, 300 g ai/ha or more, 325 g ai/ha or more, 350 g ai/ha or more, 375 g ai/ha or more, 400 g ai/ha or more, 425 g ai/ha or more, 450 g ai/ha or more, 475 g ai/ha or more, 500 g ai/ha or more, 525 g ai/ha or more, 550 g ai/ha or more, 575 g ai/ha or more, 600 g ai/ha or more, 625 g ai/ha or more, 650 g ai/ha or
  • the PS-II inhibitor herbicide can comprise dimethametryn or an agriculturally acceptable salt or ester thereof.
  • Dimethametryn shown below, is (RS)-N 2 -(1,2- dimethylpropyl)-N 4 -ethyl-6-(methylthio)-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of dimethametryn include its use in control of annual broadleaf weeds in rice.
  • Dimethametryn can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • dimethametryn is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, or 145
  • the PS-II inhibitor herbicide can comprise diuron or an agriculturally acceptable salt or ester thereof.
  • Diuron shown below, is 3-(3,4-dichlorophenyl)- 1,1-dimethylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016.
  • Diuron provides pre- and early post-emergence control of germinating grasses and broadleaf weeds in asparagus, tree fruit, bush fruit, citrus, vines, olives, pineapples, bananas, sugar cane, cotton, peppermint, alfalfa, forage legumes, cereals, maize, sorghum, and perennial grass seed crops, as well as total control of weeds and mosses in non-crop areas.
  • Diuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • diuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 600 g ai/ha or more, such as 625 g ai/ha or more, 650 g ai/ha or more, 675 g ai/ha or more, 700 g ai/ha or more, 725 g ai/ha or more, 750 g ai/ha or more, 775 g ai/ha or more, 800 g ai/ha or more, 825 g ai/ha or more, 850 g ai/ha or more, 875 g ai/ha or more, 900 g ai/ha or more, 925 g ai/ha or more, 950 g ai/ha or more, 975 g ai/ha or more, 1000 g ai/ha or more, 1100 g ai/ha or more, 1200 g
  • the PS-II inhibitor herbicide can comprise ethidimuron or an agriculturally acceptable salt or ester thereof.
  • Ethidimuron shown below, is 1-(5- ethylsulfonyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of ethidimuron include its use for total herbicidal control on uncultivated land and in sugar cane plantations.
  • Ethidimuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • ethidimuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 4000 g ai/ha or more, such as 4250 g ai/ha or more, 4500 g ai/ha or more, 4750 g ai/ha or more, 5000 g ai/ha or more, 5250 g ai/ha or more, 5500 g ai/ha or more, 5750 g ai/ha or more, 6000 g ai/ha or more, 6250 g ai/ha or more, 6500 g ai/ha or more, 6750 g ai/ha or more, 7000 g ai/ha or more, or 7250 g ai/ha or more; in an amount of 7500 g ai/ha or less, such as 7250 g ai/ha or less, 7000 g ai/ha or less, 6750
  • the PS-II inhibitor herbicide can comprise ethiozin or an agriculturally acceptable salt or ester thereof.
  • Ethiozin shown below, is 4-amino-6-tert-butyl- 3-ethylthio-1,2,4-triazin-5(4H)-one. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of ethiozin include its use in pre- emergence control of grasses and some broadleaf weeds in cereals and tomatoes. Ethiozin can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • ethiozin is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 500 g ai/ha or more, such as 525 g ai/ha or more, 550 g ai/ha or more, 575 g ai/ha or more, 600 g ai/ha or more, 625 g ai/ha or more, 650 g ai/ha or more, 675 g ai/ha or more, 700 g ai/ha or more, 725 g ai/ha or more, 750 g ai/ha or more, 775 g ai/ha or more, 800 g ai/ha or more, 825 g ai/ha or more, 850 g ai/ha or more, 875 g ai/ha or more, 900 g ai/ha or more, 925 g ai/ha or more, 950
  • the PS-II inhibitor herbicide can comprise fenuron or an agriculturally acceptable salt or ester thereof.
  • Fenuron shown below, is 1,1-dimethyl-3- phenylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of fenuron include its use in pre-emergence control of woody plants and perennial weeds in non-crop lands.
  • Fluometuron In some aspects, the PS-II inhibitor herbicide can comprise fluometuron or an agriculturally acceptable salt or ester thereof. Fluometuron, shown below, is 1,1-dimethyl-3- ( ⁇ , ⁇ , ⁇ -trifluoro-m-tolyl)-urea.
  • Fluometuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • fluometuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 800 g ai/ha or more, such as 825 g ai/ha or more, 850 g ai/ha or more, 875 g ai/ha or more, 900 g ai/ha or more, 925 g ai/ha or more, 950 g ai/ha or more, 975 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, or 1450 g ai/ha or more; in
  • the PS-II inhibitor herbicide can comprise hexazinone or an agriculturally acceptable salt or ester thereof.
  • Hexazinone shown below, is 3-cyclohexyl-6- dimethylamino-1-methyl-1,3,5-triazine-2,4-(1H,3H)-dione. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of hexazinone include its use in post-emergence control of annual, biennial, and most perennial weeds in alfalfa, pineapples, sugar can, coniferous species, and non-crop areas at 6,000-12,000 g/ha.
  • the PS-II inhibitor herbicide can comprise iodobonil or an agriculturally acceptable salt or ester thereof.
  • Iodobonil shown below, is 4-(allyloxy- carbonyloxy)-3,5-diiodobenzonitrile. Its chemical properties are given in The Pesticide Manual, Seventeenth Edition, 2016.
  • the PS-II inhibitor herbicide can comprise ioxynil or an agriculturally acceptable salt or ester thereof.
  • Ioxynil, shown below, is 4-hydroxy-3,5- diiodobenzonitrile. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016.
  • Exemplary uses of ioxynil include its use in post-emergence control of broadleaf weeds in cereals, onions, leeks, garlic, shallots, flax, sugar cane, forage grasses, lawns, and newly-sown turf.
  • Ioxynil can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • ioxynil is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 300 g ai/ha or more, such as 310 g ai/ha or more, 320 g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 370 g ai/ha or more, 380 g ai/ha or more, 390 g ai/ha or more, 400 g ai/ha or more, 420 g ai/ha or more, 440 g ai/ha or more, 450 g ai/ha or more, 460 g ai/ha or more, 480 g ai/ha or more, 500 g ai/ha or more, 520 g ai/ha or more, 540 g
  • the PS-II inhibitor herbicide can comprise isocil or an agriculturally acceptable salt or ester thereof.
  • Isocil shown below, is 3- ethoxycarbonylaminophenyl phenylcarbamate. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of isocil include its use as a total herbicide in control of perennial grasses and on non-cropped lands at 13-18 kg/ha.
  • Isomethiozin In some aspects, the PS-II inhibitor herbicide can comprise isomethiozin or an agriculturally acceptable salt or ester thereof.
  • Isomethiozin shown below, is 6-tert-butyl-4- [(EZ)-isobutylideneamino]-3-methylthio-1,2,4-triazin-5(4H)-one. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of isomethiozin include its use in post-emergence control of areas with a heavy infestation of grass, and in winter wheat and spring cereals.
  • Isoproturon In some aspects, the PS-II inhibitor herbicide can comprise isoproturon or an agriculturally acceptable salt or ester thereof. Isoproturon, shown below, is 3-(4- isopropylphenyl)-1,1-dimethylurea.
  • isoproturon Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of isoproturon include its use in pre- and post-emergence control of annual grass weeds and many broadleaf weeds in spring and winter wheat (except durum wheat), spring and winter barley, winter rye, and triticale. Isoproturon can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • isoproturon is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 800 g ai/ha or more, such as 825 g ai/ha or more, 850 g ai/ha or more, 875 g ai/ha or more, 900 g ai/ha or more, 925 g ai/ha or more, 950 g ai/ha or more, 975 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, or 1450 g ai/ha or more;
  • the PS-II inhibitor herbicide can comprise isouron or an agriculturally acceptable salt or ester thereof.
  • Isouron shown below, is 3-(5-tert-butylisoxazol- 3-yl)-1,1-dimethylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of isouron include its use in pre- and post- emergence control of broadleaf and grass weeds in sugar cane and pineapples. Isouron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • isouron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 400 g ai/ha or more, such as 425 g ai/ha or more, 450 g ai/ha or more, 475 g ai/ha or more, 500 g ai/ha or more, 525 g ai/ha or more, 550 g ai/ha or more, 575 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or
  • the PS-II inhibitor herbicide can comprise karbutilate or an agriculturally acceptable salt or ester thereof.
  • Karbutilate shown below, is 3-(3,3- dimethylureido)phenyl tert-butylcarbamate. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of karbutilate include its use in control of annual and perennial broadleaf and grass weeds and woody species in non-crop areas at up to 12,000 g/ha.
  • Lenacil In some aspects, the PS-II inhibitor herbicide can comprise lenacil or an agriculturally acceptable salt or ester thereof.
  • Lenacil shown below, is 3-cyclohexyl-1,5,6,7- tetrahydrocyclopentapyrimidine-2,4(3H)-dione. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of lenacil include its use in pre- plant and pre-emergence control of annual grass and broadleaf weeds in sugar beets, fodder beets, beetroot, sweet potatoes, spinach, strawberries, flax, black salsify, and ornamentals. Lenacil can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • lenacil is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 g ai/ha or more, such as 125 g ai/ha or more, 150 g ai/ha or more, 175 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, 275 g ai/ha or more, 300 g ai/ha or more, 325 g ai/ha or more, 350 g ai/ha or more, 375 g ai/ha or more, 400 g ai/ha or more, 425 g ai/ha or more, 450 g ai/ha or more, 475 g ai/ha or more, 500 g ai/ha or more, 525 g ai/ha or more, 550 g ai/ha
  • the PS-II inhibitor herbicide can comprise linuron or an agriculturally acceptable salt or ester thereof.
  • Linuron shown below, is 3-(3,4- dichlorophenyl)-1-methoxy-1-methyurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016.
  • Exemplary uses of linuron include its use in pre- and post-emergence control of annual grass and broadleaf weeds in asparagus, artichokes, carrots, parsley, fennel, parsnips, herbs, celery, celeriac, onions, lees, garlic, potatoes, peas, field beans, soybeans, cereals, maize, sorghum, cotton, flax, sunflowers, sugar cane, ornamentals, established vines, bananas, cassava, coffee, tea, rice, peanuts, and other crops.
  • Metamitron In some aspects, the PS-II inhibitor herbicide can comprise metamitron or an agriculturally acceptable salt or ester thereof.
  • Metamitron shown below, is 4-amino-3-methyl- 6-phenyl-1,2,4-triazin-5(4H)-one. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of metamitron include its use in pre- and post-emergence control or pre-plant control of broadleaf and grass weeds in sugar beets, fodder beets, red beets, chard, and some strawberry varieties. Metamitron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • metamitron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 300 g ai/ha or more, such as 325 g ai/ha or more, 350 g ai/ha or more, 375 g ai/ha or more, 400 g ai/ha or more, 425 g ai/ha or more, 450 g ai/ha or more, 475 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more,
  • the PS-II inhibitor herbicide can comprise met.zthiazuron or an agriculturally acceptable salt or ester thereof.
  • Met.zthiazuron shown below, is 1-(1,3- benzothiazol-2-yl)-1,3-dimethylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of methabenzthiazuron include its use in control of broadleaf and grass weeds in cereals, legumes, maize, garlic, and onions.
  • Met.zthiazuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • metambazthiazuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1250 g ai/ha or more, such as 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1550 g ai/ha or more, 1600 g ai/ha or more, 1650 g ai/ha or more, 1700 g ai/ha or more, 1750 g ai/ha or more, 1800 g ai/ha or more, 1850 g ai/ha or more, 1900 g ai/ha or more,
  • the PS-II inhibitor herbicide can comprise methoprotryne or an agriculturally acceptable salt or ester thereof.
  • Methoprotryne shown below, is N 2 -isopropyl- N 4 -(3-methoxypropyl)-6-methylthio-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of methoprotryne include its use in post-emergence control of annual broadleaf weeds and grasses in winter-sown cereals.
  • Methoprotryne can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • methoprotryne is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1200 g ai/ha or more, such as 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1550 g ai/ha or more, 1600 g ai/ha or more, 1650 g ai/ha or more, 1700 g ai/ha or more, 1750 g ai/ha or more, 1800 g ai/ha or more, 1850 g ai/ha or more, 1900 g
  • the PS-II inhibitor herbicide can comprise metobromuron or an agriculturally acceptable salt or ester thereof.
  • Metobromuron shown below, is 3-(4- bromophenyl)-1-methoxy-1-methylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of metobromuron include its use in pre- emergence control of annual broadleaf and grass weeds in beans, potatoes, tomatoes, tobacco, soybeans, maize, artichokes, and sugar beets.
  • Metobromuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • metobromuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1200 g ai/ha or more, such as 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1550 g ai/ha or more, 1600 g ai/ha or more, 1650 g ai/ha or more, 1700 g ai/ha or more, 1750 g ai/ha or more, 1800 g ai/ha or more, 1850 g ai/ha or more, 1900 g a
  • the PS-II inhibitor herbicide can comprise metoxuron or an agriculturally acceptable salt or ester thereof.
  • Metoxuron shown below, is 3-(3-chloro-4- methoxyphenyl)-1,1-dimethylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of metoxuron include its use in pre- and post-emergence control of some grasses and annual broadleaf weeds in winter wheat, winter barley, winter rye, carrots, some varieties of spring wheat, for desiccation of potato plants, and pre-harvest defoliation in hemp, flax, and tomatoes.
  • Metoxuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • metoxuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2200 g ai/ha or more, such as 2250 g ai/ha or more, 2300 g ai/ha or more, 2350 g ai/ha or more, 2400 g ai/ha or more, 2450 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2700 g ai/ha or more, 2800 g ai/ha or more, 2900 g ai/ha or more, 3000 g ai/ha or more, 3100 g ai/ha or more, 3200 g ai/ha or more, 3300
  • the PS-II inhibitor herbicide can comprise metribuzin or an agriculturally acceptable salt or ester thereof.
  • Metribuzin shown below, is 4-amino-6-tert- butyl-3-methythio-1,2,4-triazin-5(4H)-one. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of metribuzin include its use in pre- and post-emergence control of grass and broadleaf weeds in soybeans, potatoes, tomatoes, sugar cane, alfalfa, asparagus, maize, and cereals.
  • Metribuzin can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • metribuzin is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or
  • the PS-II inhibitor herbicide can comprise monolinuron or an agriculturally acceptable salt or ester thereof.
  • Monolinuron shown below, is 3-(4- chlorophenyl)-1-methoxy-1-methylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of monolinuron include its use in pre- and post-emergence control of annual broadleaf and some grass weeds in asparagus, berries, maize, dwarf French beans, field beans, vines, leeks, onions, potatoes, herbs, alfalfa, flowers and ornamentals, and trees.
  • the PS-II inhibitor herbicide can comprise neburon or an agriculturally acceptable salt or ester thereof.
  • Neburon shown below, is 1-butyl-3-(3,4- dichlorophenyl)-1-methylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of neburon include its use in pre-emergence control of annual broadleaf and grass weeds in beans, peas, alfalfa, garlic, cereals, beets, strawberries, ornamentals, and forestry. Neburon can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • neburon is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1750 g ai/ha or more, such as 1800 g ai/ha or more, 1850 g ai/ha or more, 1900 g ai/ha or more, 1950 g ai/ha or more, 2000 g ai/ha or more, 2050 g ai/ha or more, 2100 g ai/ha or more, 2150 g ai/ha or more, 2200 g ai/ha or more, 2250 g ai/ha or more, 2300 g ai/ha or more, 2350 g ai/ha or more, 2400 g ai/ha or more, 2450 g ai/ha or more, 2500 g ai/ha or more, 2550 g ai/ha or more, 2600 g ai/ha or more, 2650
  • the PS-II inhibitor herbicide can comprise pentanochlor or an agriculturally acceptable salt or ester thereof.
  • Pentanochlor shown below, is (RS)-3'-chloro- 2-methylvalero-p-toluidide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of pentanochlor include its use in selective pre- and post-emergence herbicidal control in carrots, celeriac, celery, fennel, parsley, parsnips, peas, tomatoes, some flower crops, fruit trees, and ornamentals at less than 4000 g/ha.
  • the PS-II inhibitor herbicide can comprise phenmedipham or an agriculturally acceptable salt or ester thereof.
  • Phenmedipham shown below, is 3- methoxycarbonylaminophenyl 3'-methylcarbanilate. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of phenmedipham include its use in post-emergence control of broadleaf weeds in sugar beets, strawberries, spinach, peas, chard, and red beets.
  • Phenmedipham can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • phenmedipham is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 150 g ai/ha or more, such as 175 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, 275 g ai/ha or more, 300 g ai/ha or more, 325 g ai/ha or more, 350 g ai/ha or more, 375 g ai/ha or more, 400 g ai/ha or more, 425 g ai/ha or more, 450 g ai/ha or more, 475 g ai/ha or more, 500 g ai/ha or more, 525 g ai/ha or more, 550 g ai/ha or more, 575 g ai/ha or more, 600 g ai
  • the PS-II inhibitor herbicide can comprise prometon or an agriculturally acceptable salt or ester thereof.
  • Prometon shown below, is N 2 ,N 4 -diisopropyl- 6-methoxy-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of prometon include its use in pre- or early post-emergence control of annual and perennial paddy weeds in direct-seeded and transplanted rice. Prometon can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • prometon is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 g ai/ha or more, such as 125 g ai/ha or more, 150 g ai/ha or more, 175 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, 275 g ai/ha or more, 300 g ai/ha or more, or 325 g ai/ha or more; in an amount of 350 g ai/ha or less, such as 325 g ai/ha or less, 300 g ai/ha or less, 275 g ai/ha or less, 250 g ai/ha or less, 225 g ai/ha or less, 200 g ai/ha or less, 175 g ai/ha or less, 150 g
  • the PS-II inhibitor herbicide can comprise prometryn or an agriculturally acceptable salt or ester thereof.
  • Prometryn shown below, is N 2 ,N 4 -diisopropyl- 6-methylthio-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of prometryn include its use in pre- or post-emergence control of annual grass and broadleaf weeds in cotton, sunflowers, peanuts, potatoes, carrots, peas, beans, celery, and leeks.
  • Prometryn can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • prometryn is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 500 g ai/ha or more, such as 550 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more
  • the PS-II inhibitor herbicide can comprise propanil or an agriculturally acceptable salt or ester thereof.
  • Propanil shown below, is 3',4'- dichloropropionanilide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of propanil include its use in post-emergence control of broadleaf and grass weeds in rice. Propanil can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • propanil is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 5 g ai/ha or more, such as 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more,
  • the PS-II inhibitor herbicide can comprise propazine or an agriculturally acceptable salt or ester thereof.
  • Propazine shown below, is 6-chloro-N 2 ,N 4 - diisopropyl-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of propazine include its use in pre-plant, pre-, or post-emergence control of grass and broadleaf weeds in sorghum, carrots, chervil, parsley, and glasshouse ornamentals.
  • Propazine can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • propazine is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 250 g ai/ha or more, such as 275 g ai/ha or more, 300 g ai/ha or more, 325 g ai/ha or more, 350 g ai/ha or more, 375 g ai/ha or more, 400 g ai/ha or more, 425 g ai/ha or more, 450 g ai/ha or more, 475 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more,
  • the PS-II inhibitor herbicide can comprise pyridafol or an agriculturally acceptable salt or ester thereof.
  • Pyridafol shown below, is 6-chloro-3- phenylpyridazin-4-ol. According to The Pesticide Manual, Seventeenth Edition, 2016, pyridafol was evaluated by Novartis Crop Protection AG.
  • Pyridate In some aspects, the PS-II inhibitor herbicide can comprise pyridate or an agriculturally acceptable salt or ester thereof. Pyridate, shown below, is O-6-chloro-3- phenylpyridazin-4-yl S-octyl thiocarbonate.
  • pyridate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pyridate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 g ai/ha or more, such as 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g ai/ha or
  • the PS-II inhibitor herbicide can comprise siduron or an agriculturally acceptable salt or ester thereof.
  • Siduron shown below, is 1-(2- methylcyclohexyl)-3-phenylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of siduron include its use in pre- emergence control of Digitaria spp. and annual grass weeds in turf farms, grass seed production, and established turf.
  • Siduron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • siduron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2000 g ai/ha or more, such as 2100 g ai/ha or more, 2250 g ai/ha or more, 2500 g ai/ha or more, 2750 g ai/ha or more, 3000 g ai/ha or more, 3500 g ai/ha or more, 4000 g ai/ha or more, 4500 g ai/ha or more, 5000 g ai/ha or more, 6000 g ai/ha or more, 7000 g ai/ha or more, 7500 g ai/ha or more, 8000 g ai/ha or more, 9000 g ai/ha or more, 10,000 g ai/ha or more, 11,000 g ai/ha or more, 12,000 g ai/ha or more, 13,000
  • the PS-II inhibitor herbicide can comprise simazine or an agriculturally acceptable salt or ester thereof.
  • Simazine shown below, is 6-chloro-N 2 ,N 4 - diethyl-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016.
  • simazine includes its use in pre- emergence control of broadleaf and annual grass weeds in pome fruit, stone fruit, bush and cane fruits, citrus, vines, strawberries, nuts, olives, pineapples, field beans, French beans, peas, maize, asparagus, hops, alfalfa, lupins, oilseed rape, artichokes, sugar cane, plantation trees, turf, and ornamentals.
  • Simazine can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • simazine is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1250 g ai/ha or more, such as 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1550 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1800 g ai/ha or more, 1900 g ai/ha or more, 2000 g ai/ha or more, 2100 g ai/ha or more, 2200 g ai/ha or more, 2300 g ai/ha or more, 2400 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2700 g a
  • the PS-II inhibitor herbicide can comprise symetryn or an agriculturally acceptable salt or ester thereof.
  • Symetryn shown below, is N 2 ,N 4 -diethyl-6- methylthio-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of symetryn include its use in control of broadleaf weeds in rice.
  • Tebuthiuron In some aspects, the PS-II inhibitor herbicide can comprise tebuthiuron or an agriculturally acceptable salt or ester thereof.
  • Tebuthiuron shown below, is 1-(5-tert-butyl- 1,3,4-thiadiazol-2-yl)-1,3-dimethylurea. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of tebuthiuron include its use in pre- emergence control of herbaceous and woody plants, annual weeds, and perennial grass and broadleaf weeds in non-crop sites, pastures, rangeland, and sugar cane. Tebuthiuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • tebuthiuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 500 g ai/ha or more, such as 520 g ai/ha or more, 540 g ai/ha or more, 560 g ai/ha or more, 580 g ai/ha or more, 600 g ai/ha or more, 625 g ai/ha or more, 650 g ai/ha or more, 675 g ai/ha or more, 700 g ai/ha or more, 725 g ai/ha or more, 750 g ai/ha or more, 775 g ai/ha or more, 800 g ai/ha or more, 825 g ai/ha or more, 850 g ai/ha or more, 875 g ai/ha or more, 900 g ai/ha or more,
  • the PS-II inhibitor herbicide can comprise terbacil or an agriculturally acceptable salt or ester thereof.
  • Terbacil shown below, is 3-tert-butyl-5-chloro- 6-methyluracil. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of terbacil include its use in pre- and post-emergence control of annual and some perennial grass, broadleaf, and sedge weeds in apples, citrus, alfalfa, tree fruit, strawberries, blueberries, mint, and sugar cane. Terbacil can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • terbacil is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 300 g ai/ha or more, such as 310 g ai/ha or more, 320 g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 370 g ai/ha or more, 380 g ai/ha or more, 390 g ai/ha or more, 400 g ai/ha or more, 420 g ai/ha or more, 440 g ai/ha or more, 460 g ai/ha or more, 480 g ai/ha or more, 500 g ai/ha or more, 520 g ai/ha or more, 540 g ai/ha or more, 560 g ai/
  • the PS-II inhibitor herbicide can comprise terbumeton or an agriculturally acceptable salt or ester thereof.
  • Terbumeton shown below, is N 2 -tert-butyl-N 4 - ethyl-6-methoxy-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of terbumeton include its use in pre-emergence control of annual and perennial grass and broadleaf weeds in citrus, vineyards, apples, and forestry.
  • Terbumeton can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • terbumeton is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2700 g ai/ha or more, such as 2750 g ai/ha or more, 2800 g ai/ha or more, 2900 g ai/ha or more, 3000 g ai/ha or more, 3100 g ai/ha or more, 3200 g ai/ha or more, 3300 g ai/ha or more, 3400 g ai/ha or more, 3500 g ai/ha or more, 3600 g ai/ha or more, 3700 g ai/ha or more, 3800 g ai/ha or more, 3900 g ai/ha or more 4000 g
  • the PS-II inhibitor herbicide can comprise terbuthylazine or an agriculturally acceptable salt or ester thereof.
  • Terbuthylazine shown below, is N 2 -tert-butyl- 6-chloro-N 4 -ethyl-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016.
  • terbuthylazine examples include its use in pre- and post-emergence control of broadleaf and grass weeds in maize, sorghum, tree fruits, citrus, vines, coffee, oil palms, cocoa, potatoes, olives, peas, beans, sugar cane, rubber, tree nurseries, and new plantings.
  • Terbuthylazine can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • terbuthylazine is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 500 g ai/ha or more, such as 520 g ai/ha or more, 540 g ai/ha or more, 560 g ai/ha or more, 580 g ai/ha or more, 600 g ai/ha or more, 625 g ai/ha or more, 650 g ai/ha or more, 675 g ai/ha or more, 700 g ai/ha or more, 725 g ai/ha or more, 750 g ai/ha or more, 775 g ai/ha or more, 800 g ai/ha or more, 825 g ai/ha or more, 850 g ai/ha or more, 875 g ai/ha or more, 900 g ai/ha or more,
  • the PS-II inhibitor herbicide can comprise terbutryn or an agriculturally acceptable salt or ester thereof.
  • Terbutryn shown below, is N 2 -tert-butyl-N 4 - ethyl-6-methylthio-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of terbutryn include its use in pre-emergence control of broadleaf and grass weeds in winter cereals, beans, peas, maize, sugar cane, sunflowers, potatoes, cotton, and peanuts.
  • Terbutryn can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • terbutryn is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 150 g ai/ha or more, such as 175 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, 275 g ai/ha or more, 300 g ai/ha or more, 325 g ai/ha or more, 350 g ai/ha or more, 375 g ai/ha or more, 400 g ai/ha or more, 425 g ai/ha or more, 450 g ai/ha or more, 475 g ai/ha or more, 500 g ai/ha or
  • the PS-II inhibitor herbicide can comprise trietazine or an agriculturally acceptable salt or ester thereof.
  • Trietazine shown below, is 6-chloro-N 2 ,N 2 ,N 4 - triethyl-1,3,5-triazine-2,4-diamine. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of trietazine include its use in control of weeds in potatoes, field beans, and peas. Trietazine can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • trietazine is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1500 g ai/ha or more, such as 1550 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1800 g ai/ha or more, 1900 g ai/ha or more, 2000 g ai/ha or more, 2200 g ai/ha or more, 2400 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2800 g ai/ha or more, 3000 g ai/ha or more, 3200 g ai/ha or more, 3400 g ai/ha or more, 3500 g ai/ha or more, 3600 g ai/ha or more, 3800 g ai/ha or more, 4000
  • compositions can optionally include a 4- hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide.
  • HPPD inhibitor herbicides interfere with an oxygenase enzyme involved in the creation of energy in plants and higher order eukaryotes.
  • HPPD inhibitors examples include benzobicyclon, benzofenap, bicyclopyrone, fenquinotrione, isoxachlortole, isoxaflutole, lancotrione, mesotrione, pyraquinate, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, or an agriculturally acceptable salt or ester thereof, and combinations thereof.
  • the composition can include a HPPD inhibitor herbicide selected from the group consisting of benzobicyclon, benzofenap, bicyclopyrone, fenquinotrione, isoxachlortole, isoxaflutole, lancotrione, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, an agriculturally acceptable salt or ester thereof, and combinations thereof.
  • a HPPD inhibitor herbicide selected from the group consisting of benzobicyclon, benzofenap, bicyclopyrone, fenquinotrione, isoxachlortole, isoxaflutole, lancotrione, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembot
  • the HPPD inhibitor herbicide or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the HPPD inhibitor herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 1.1 g ai/ha or more, 1.25 g ai/ha or more, 1.5 g ai/ha or more, 1.75 g ai/ha or more, 2 g ai/ha or more, 2.5 g ai/ha or more, 3 g ai/ha or more, 3.5 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g
  • the composition contains: compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof); (b) a PS-II inhibitor herbicide selected from ametryne, amicarbazone, atrazine, bentazone, bromacil, bromofenoxim, bromoxynil, chlorbromuron, chloridazon, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diuron, ethidimuron, ethiozin, fenuron, fluometuron, hexazinone, iodobonil, ioxynil, isocil, isomethiozin, isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, methoprotryne, metobromuron, metoxuron, me
  • the HPPD inhibitor herbicide can comprise benzobicyclon or an agriculturally acceptable salt or ester thereof.
  • Benzobicyclon shown below, is 3-[2-chloro-4- (methylsulfonyl)benzoyl]-4-(phenylthio)bicyclo[3.2.1]oct-3-en-2-one. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of benzobicyclon include its use for pre- to early post-emergence control of annual and perennial paddy weeds in direct-seeded and transplanted rice.
  • Benzobicyclon can be applied to vegetation or an area adjacent to the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • benzobicyclon is applied to vegetation or an area adjacent to the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g
  • the HPPD inhibitor herbicide can comprise benzofenap or an agriculturally acceptable salt or ester thereof.
  • Benzofenap shown below, is 2-[[4-(2,4- dichloro-3-methylbenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-1-(4-methylphenyl) ethanone. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of benzofenap include its use for control of broadleaf weeds in rice.
  • Benzofenap can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • benzofenap is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 300 g ai/ha or more, such as 310 g ai/ha or more, 320 g ai/ha or more, 340 g ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, 400 g ai/ha or more, 450 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more, 625 g ai/ha or more, 650 g ai/ha or more, 675 g ai/ha or more, 700 g a
  • the HPPD inhibitor herbicide can comprise bicyclopyrone or an agriculturally acceptable salt or ester thereof.
  • Bicyclopyrone shown below, is 4-hydroxy-3- [[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl] bicyclo[3.2.1]oct- 3-en-2-one. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of bicyclopyrone include its use for pre- and early post- emergence control of broadleaf and grass weeds in maize and cereals.
  • Bicyclopyrone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • bicyclopyrone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 100 g ai
  • the HPPD inhibitor herbicide can comprise fenquinotrione or an agriculturally acceptable salt or ester thereof.
  • Fenquinotrione shown below, is 2-[[8-chloro- 3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione.
  • fenquinotrione is a herbicide under development for use on rice.
  • the HPPD inhibitor herbicide can comprise isoxachlortole or an agriculturally acceptable salt or ester thereof.
  • Isoxachlortole shown below, is [4-chloro-2- (methylsulfonyl)phenyl](5-cyclopropyl-4-isoxazolyl) methanone.
  • isoxachlortole is a herbicide that was evaluated by Rhône- Poulenc.
  • the HPPD inhibitor herbicide can comprise isoxaflutole or an agriculturally acceptable salt or ester thereof.
  • Isoxaflutole shown below, is (5-cyclopropyl-4- isoxazolyl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl] methanone.
  • isoxaflutole Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of isoxaflutole include its use for pre- emergence or pre-plant control of grass and broadleaf weed in maize and sugar cane. Isoxaflutole can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • isoxaflutole is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/
  • the HPPD inhibitor herbicide can comprise lancotrione or an agriculturally acceptable salt or ester thereof.
  • Lancotrione shown below, is 2-[2-chloro-3-[2- (1,3-dioxolan-2-yl)ethoxy]-4-(methylsulfonyl)benzoyl]-3-hydroxy-2-cyclohexen-1-one.
  • lancotrione is a herbicide under development by Ishihara Sangyo Kaisha, Ltd.
  • Mesotrione In some aspects, the HPPD inhibitor herbicide can comprise mesotrione or an agriculturally acceptable salt or ester thereof.
  • Mesotrione shown below, is 2-[4- (methylsulfonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of mesotrione include its use for pre- and post- emergence control of broadleaf weeds and some grass weeds in maize. Mesotrione can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • mesotrione is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g a
  • the HPPD inhibitor herbicide can comprise pyrasulfotole or an agriculturally acceptable salt or ester thereof.
  • Pyrasulfotole shown below, is (5-hydroxy-1,3- dimethyl-1H-pyrazol-4-yl)[2-(methylsulfonyl)-4-(trifluoromethyl) phenyl]methanone. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of pyrasulfotole include its use in mixture with mefenpyr-diethyl and bromoxynil or MCPA ester, for post- emergence control of broadleaf weeds in cereals.
  • Pyrasulfotole can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pyrasulfotole is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 1.1 g ai/ha or more, 1.25 g ai/ha or more, 1.4 g ai/ha or more, 1.5 g ai/ha or more, 1.6 g ai/ha or more, 1.75 g ai/ha or more, 1.9 g ai/ha or more, 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g
  • the HPPD inhibitor herbicide can comprise pyrazolynate or an agriculturally acceptable salt or ester thereof.
  • Pyrazolynate shown below, is (2,4- dichlorophenyl)[1,3-dimethyl-5-[[(4-methylphenyl) sulfonyl]oxy]-1H-pyrazol-4- yl]methanone. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of pyrazolynate include its use to control grasses, sedges, Potamogeton distinctus, Sagittaria pygmaea, Sagittaria trifolia and Alisma canaliculatum in paddy rice.
  • Pyrazolynate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pyrazolynate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1000 g ai/ha or more, such as 1100 g ai/ha or more, 1200 g ai/ha or more, 1400 g ai/ha or more, 1600 g ai/ha or more, 1800 g ai/ha or more, 2000 g ai/ha or more, 2200 g ai/ha or more, 2400 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2800 g ai/ha or more, 3000 g ai/ha or more, 3200 g ai/ha or more, 3400 g
  • the HPPD inhibitor herbicide can comprise pyrazoxyfen or an agriculturally acceptable salt or ester thereof.
  • Pyrazoxyfen shown below, is 2-[[4-(2,4- dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-1-phenylethanone. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of pyrazoxyfen include pre- or post-emergence control of annual and perennial weeds in transplanted or direct-seeded paddy rice.
  • Pyrazoxyfen can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pyrazoxyfen is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1000 g ai/ha or more, such as 1100 g ai/ha or more, 1200 g ai/ha or more, 1400 g ai/ha or more, 1600 g ai/ha or more, 1800 g ai/ha or more, 2000 g ai/ha or more, 2200 g ai/ha or more, 2400 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2800 g ai/ha or more, 3000 g ai/ha or more, 3200 g ai/ha or more, 3400 g
  • the HPPD inhibitor herbicide can comprise sulcotrione or an agriculturally acceptable salt or ester thereof.
  • Sulcotrione shown below, is 2-[2-chloro-4- (methylsulfonyl)benzoyl]-1,3-cyclohexanedione. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of sulcotrione include its use to control broadleaf weeds and grasses post-emergence in maize and sugar cane. Sulcotrione can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • sulcotrione is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g a
  • the HPPD inhibitor herbicide can comprise tefuryltrione or an agriculturally acceptable salt or ester thereof.
  • Tefuryltrione shown below, is 2-[2-chloro-4- (methylsulfonyl)-3-[[(tetrahydro-2-furanyl)methoxy] methyl]benzoyl]-1,3-cyclohexandione.
  • tefuryltrione is a herbicide jointly developed by Bayer CropScience, Hokko Chemical, and Zen-Noh for pre-and post-emergence control of annual and perennial broadleaf weeds in rice and cereals.
  • the HPPD inhibitor herbicide can comprise tembotrione or an agriculturally acceptable salt or ester thereof.
  • Tembotrione shown below, is 2-[2-chloro-4- (methylsulfonyl)-3-[(2,2,2-trifluoroethoxy) methyl]benzoyl]-1,3-cyclohexanedione. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of tembotrione include its use for post-emergence control of grass and broadleaf weed species in maize. Tembotrione can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • tembotrione is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 1.1 g ai/ha or more, 1.25 g ai/ha or more, 1.4 g ai/ha or more, 1.5 g ai/ha or more, 1.6 g ai/ha or more, 1.75 g ai/ha or more, 1.9 g ai/ha or more, 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.5 g ai/ha or more, 5 g a
  • the HPPD inhibitor herbicide can comprise tolpyralate or an agriculturally acceptable salt or ester thereof.
  • Tolpyralate shown below, is 1-[[1-ethyl-4-[3- (2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl]oxy]ethyl methyl carbonate.
  • tefuryltrione is a herbicide developed by Ishihara Sangyo Kaisha Ltd. for pre-and post-emergence control of broadleaf and grass weeds, including Palmer amaranth, water hemp, giant ragweed, and giant foxtail in maize.
  • the HPPD inhibitor herbicide can comprise topramezone or an agriculturally acceptable salt or ester thereof.
  • Topramezone shown below, is [3-(4,5-dihydro- 3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4- yl)methanone. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of topramezone include its use for post-emergence weed control in maize. Topramezone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • topramezone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 1.1 g ai/ha or more, 1.25 g ai/ha or more, 1.4 g ai/ha or more, 1.5 g ai/ha or more, 1.6 g ai/ha or more, 1.75 g ai/ha or more, 1.9 g ai/ha or more, 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.5 g ai/ha or more, 5 g ai/ha or
  • compositions can include an inhibitor of 4-hydroxyphenylpyruvate dioxygenase (HPPD), an oxygenase enzyme involved in the creation of energy in plants and higher order eukaryotes.
  • HPPD 4-hydroxyphenylpyruvate dioxygenase
  • oxygenase enzyme involved in the creation of energy in plants and higher order eukaryotes.
  • HPPD inhibitors examples include benzobicyclon, benzofenap, bicyclopyrone, fenquinotrione, isoxachlortole, isoxaflutole, lancotrione, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, or an agriculturally acceptable salt or esters thereof, and combinations thereof.
  • the HPPD inhibitor or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent to the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the HPPD inhibitor or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 grams active ingredient per hectare (g ai/ha) or more, such as 1.1 g ai/ha or more, 1.25 g ai/ha or more, 1.5 g ai/ha or more, 1.75 g ai/ha or more, 2 g ai/ha or more, 2.5 g ai/ha or more, 3 g ai/ha or more, 3.5 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 11 g ai/ha or more, 12 g ai/ha or
  • the herbicidal composition contains a herbicidally effective amount of compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) benzobicyclon, benzofenap, bicyclopyrone, fenquinotrione, isoxachlortole, isoxaflutole, lancotrione, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, agriculturally acceptable salts or esters, or combinations thereof.
  • the HPPD inhibitor herbicide can comprise benzobicyclon or an agriculturally acceptable salt or ester thereof.
  • Benzobicyclon shown below, is 3-[2-chloro-4- (methylsulfonyl)benzoyl]-4-(phenylthio)bicyclo[3.2.1]oct-3-en-2-one. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of benzobicyclon include its use for pre- to early post-emergence control of annual and perennial paddy weeds in direct-seeded and transplanted rice.
  • Benzobicyclon can be applied to vegetation or an area adjacent to the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • benzobicyclon is applied to vegetation or an area adjacent to the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g
  • the HPPD inhibitor herbicide can comprise benzofenap or an agriculturally acceptable salt or ester thereof.
  • Benzofenap shown below, is 2-[[4-(2,4- dichloro-3-methylbenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-1-(4-methylphenyl) ethanone. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of benzofenap include its use for control of broadleaf weeds in rice.
  • Benzofenap can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • benzofenap is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 300 g ai/ha or more, such as 310 g ai/ha or more, 320 g ai/ha or more, 340 g ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, 400 g ai/ha or more, 450 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more, 625 g ai/ha or more, 650 g ai/ha or more, 675 g ai/ha or more, 700 g a
  • the HPPD inhibitor herbicide can comprise bicyclopyrone or an agriculturally acceptable salt or ester thereof.
  • Bicyclopyrone shown below, is 4-hydroxy-3- [[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl] bicyclo[3.2.1]oct- 3-en-2-one. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of bicyclopyrone include its use for pre- and early post- emergence control of broadleaf and grass weeds in maize and cereals.
  • Bicyclopyrone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • bicyclopyrone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 100 g ai
  • the HPPD inhibitor herbicide can comprise fenquinotrione or an agriculturally acceptable salt or ester thereof.
  • Fenquinotrione shown below, is 2-[[8-chloro- 3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2-quinoxalinyl]carbonyl]-1,3-cyclohexanedione.
  • fenquinotrione is a herbicide under development for use on rice.
  • the HPPD inhibitor herbicide can comprise isoxachlortole or an agriculturally acceptable salt or ester thereof.
  • Isoxachlortole shown below, is [4-chloro-2- (methylsulfonyl)phenyl](5-cyclopropyl-4-isoxazolyl) methanone.
  • isoxachlortole is a herbicide that was evaluated by Rhône- Poulenc.
  • the HPPD inhibitor herbicide can comprise isoxaflutole or an agriculturally acceptable salt or ester thereof.
  • Isoxaflutole shown below, is (5-cyclopropyl-4- isoxazolyl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl] methanone.
  • isoxaflutole Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of isoxaflutole include its use for pre- emergence or pre-plant control of grass and broadleaf weed in maize and sugar cane. Isoxaflutole can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • isoxaflutole is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/
  • the HPPD inhibitor herbicide can comprise lancotrione or an agriculturally acceptable salt or ester thereof.
  • Lancotrione shown below, is 2-[2-chloro-3-[2- (1,3-dioxolan-2-yl)ethoxy]-4-(methylsulfonyl)benzoyl]-3-hydroxy-2-cyclohexen-1-one.
  • lancotrione is a herbicide under development by Ishihara Sangyo Kaisha, Ltd.
  • Mesotrione In some aspects, the HPPD inhibitor herbicide can comprise mesotrione or an agriculturally acceptable salt or ester thereof.
  • Mesotrione shown below, is 2-[4- (methylsulfonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of mesotrione include its use for pre- and post- emergence control of broadleaf weeds and some grass weeds in maize. Mesotrione can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • mesotrione is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g a
  • the HPPD inhibitor herbicide can comprise pyrasulfotole or an agriculturally acceptable salt or ester thereof.
  • Pyrasulfotole shown below, is (5-hydroxy-1,3- dimethyl-1H-pyrazol-4-yl)[2-(methylsulfonyl)-4-(trifluoromethyl) phenyl]methanone. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of pyrasulfotole include its use in mixture with mefenpyr-diethyl and bromoxynil or MCPA ester, for post- emergence control of broadleaf weeds in cereals.
  • Pyrasulfotole can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pyrasulfotole is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 1.1 g ai/ha or more, 1.25 g ai/ha or more, 1.4 g ai/ha or more, 1.5 g ai/ha or more, 1.6 g ai/ha or more, 1.75 g ai/ha or more, 1.9 g ai/ha or more, 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g
  • the HPPD inhibitor herbicide can comprise pyrazolynate or an agriculturally acceptable salt or ester thereof.
  • Pyrazolynate shown below, is (2,4- dichlorophenyl)[1,3-dimethyl-5-[[(4-methylphenyl) sulfonyl]oxy]-1H-pyrazol-4- yl]methanone. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of pyrazolynate include its use to control grasses, sedges, Potamogeton distinctus, Sagittaria pygmaea, Sagittaria trifolia and Alisma canaliculatum in paddy rice.
  • Pyrazolynate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pyrazolynate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 200 g ai/ha or more, such as 225 g ai/ha or more, 250 g ai/ha or more, 275 g ai/ha or more, 300 g ai/ha or more, 350 g ai/ha or more, 400 g ai/ha or more, 450 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha
  • the HPPD inhibitor herbicide can comprise pyrazoxyfen or an agriculturally acceptable salt or ester thereof.
  • Pyrazoxyfen shown below, is 2-[[4-(2,4- dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl]oxy]-1-phenylethanone. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of pyrazoxyfen include pre- or post-emergence control of annual and perennial weeds in transplanted or direct-seeded paddy rice.
  • Pyrazoxyfen can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pyrazoxyfen is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1000 g ai/ha or more, such as 1100 g ai/ha or more, 1200 g ai/ha or more, 1400 g ai/ha or more, 1600 g ai/ha or more, 1800 g ai/ha or more, 2000 g ai/ha or more, 2200 g ai/ha or more, 2400 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2800 g ai/ha or more, 3000 g ai/ha or more, 3200 g ai/ha or more, 3400 g
  • the HPPD inhibitor herbicide can comprise sulcotrione or an agriculturally acceptable salt or ester thereof.
  • Sulcotrione shown below, is 2-[2-chloro-4- (methylsulfonyl)benzoyl]-1,3-cyclohexanedione. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of sulcotrione include its use to control broadleaf weeds and grasses post-emergence in maize and sugar cane. Sulcotrione can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • sulcotrione is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g a
  • the HPPD inhibitor herbicide can comprise tefuryltrione or an agriculturally acceptable salt or ester thereof.
  • Tefuryltrione shown below, is 2-[2-chloro-4- (methylsulfonyl)-3- [[(tetrahydro-2-furanyl)-methoxy]-methyl]-benzoyl]- 1,3- cyclohexandione.
  • tefuryltrione is a herbicide jointly developed by Bayer CropScience, Hokko Chemical, and Zen-Noh for pre-and post-emergence control of annual and perennial broadleaf weeds in rice and cereals.
  • the HPPD inhibitor herbicide can comprise tembotrione or an agriculturally acceptable salt or ester thereof.
  • Tembotrione shown below, is 2-[2-chloro-4- (methylsulfonyl)-3-[(2,2,2-trifluoroethoxy) methyl]benzoyl]-1,3-cyclohexanedione. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of tembotrione include its use for post-emergence control of grass and broadleaf weed species in maize. Tembotrione can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • tembotrione is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 1.1 g ai/ha or more, 1.25 g ai/ha or more, 1.4 g ai/ha or more, 1.5 g ai/ha or more, 1.6 g ai/ha or more, 1.75 g ai/ha or more, 1.9 g ai/ha or more, 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.5 g ai/ha or more, 5 g a
  • the HPPD inhibitor herbicide can comprise tolpyralate or an agriculturally acceptable salt or ester thereof.
  • Tolpyralate shown below, is 1-[[1-ethyl-4-[3- (2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl]oxy]ethyl methyl carbonate.
  • tefuryltrione is a herbicide developed by Ishihara Sangyo Kaisha Ltd. for pre-and post-emergence control of broadleaf and grass weeds, including Palmer amaranth, water hemp, giant ragweed, and giant foxtail in maize.
  • the HPPD inhibitor herbicide can comprise topramezone or an agriculturally acceptable salt or ester thereof.
  • Topramezone shown below, is [3-(4,5-dihydro- 3-isoxazolyl)-2-methyl-4-(methylsulfonyl) phenyl] (5-hydroxy-1-methyl- 1H-pyrazol-4-yl) methanone. Its herbicidal activity is exemplified in The Pesticide Manual. Exemplary uses of topramezone include its use for post-emergence weed control in maize. Topramezone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • topramezone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 1.1 g ai/ha or more, 1.25 g ai/ha or more, 1.4 g ai/ha or more, 1.5 g ai/ha or more, 1.6 g ai/ha or more, 1.75 g ai/ha or more, 1.9 g ai/ha or more, 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.5 g ai/ha or more, 5 g ai/ha or
  • compositions include an acetyl CoA carboxylase (ACCase) inhibitor herbicide or an agriculturally acceptable salt or ester thereof.
  • ACCase inhibitor herbicides inhibit lipid biosynthesis in the plant. Examples of ACCase inhibitor herbicides include aryloxyphenoxypropionates, cyclohexanediones, and phenylpyrazolines.
  • the ACCase inhibitor herbicide can include an aryloxyphenoxypropionate herbicide.
  • the ACCase inhibitor herbicide can include a cyclohexanedione herbicide. In some aspects, the ACCase inhibitor herbicide can include a phenylpyrazoline herbicide. In some aspects, the composition can include an ACCase inhibitor selected from the group of cyclohexanediones, aryloxyphenoxypropionates, phenylpyrazolines, or combinations thereof.
  • the composition can include clodinafop, cyhalofop, diclofop, fenoxaprop, fenthiaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, agriculturally acceptable salts or esters thereof, or combinations thereof.
  • the composition can include, alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, pyriflubenzoxim, sethoxydim, tepraloxydim, tralkoxydim, agriculturally acceptable salts or esters thereof, or combinations thereof.
  • the composition can include pinoxaden.
  • the composition can include an ACCase inhibitor herbicide selected from the group consisting of alloxydim, butroxydim, clethodim, clodinafop, cloproxydim, cycloxydim, cyhalofop, diclofop, fenoxaprop, fenthiaprop, fluazifop, haloxyfop, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim, tralkoxydim, agriculturally acceptable salts and esters thereof, and combinations thereof.
  • an ACCase inhibitor herbicide selected from the group consisting of alloxydim, butroxydim, clethodim, clodinafop, cloproxydim, cycloxydim, cyhalofop, diclofop, fenoxa
  • the ACCase inhibitor herbicide or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the ACCase inhibitor herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2 g ai/ha or more, such as 2.5 g ai/ha or more, 3 g ai/ha or more, 3.5 g ai/ha or more, 4 g ai/ha or more, 4.5 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 15 g ai/ha or more
  • the composition contains: compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof); and (b) alloxydim, butroxydim, clethodim, clodinafop, cloproxydim, cycloxydim, cyhalofop, diclofop, fenoxaprop, fenthiaprop, fluazifop, haloxyfop, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim, tralkoxydim, agriculturally acceptable salts and esters thereof, and combinations thereof.
  • Alloxydim Compositions and methods of the present disclosure can include alloxydim or an agriculturally acceptable salt or ester thereof.
  • Alloxydim shown below, is a cyclohexanedione herbicide that provides post-emergence control of grass weeds and volunteer cereals in sugar beet, vegetables and broad-leaved crops. Alloxydim, as well as methods of preparing alloxydim, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Alloxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • alloxydim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 299 g ai/ha or more, such as 300 g ai/ha or more, 320 g ai/ha or more, 340 g ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, 400 g ai/ha or more, 420 g ai/ha or more, 440 g ai/ha or more, 460 g ai/ha or more, 480 g ai/ha or more, 500 g ai/ha or more, 520 g ai/ha or more, 540 g ai/ha or more, 560 g ai/ha or more, 580 g ai/ha or more, 600 g ai/ha or more, 620 g ai/ha or more, 640 g ai/
  • Butroxydim Compositions and methods of the present disclosure can include butroxydim or an agriculturally acceptable salt or ester thereof.
  • Butroxydim shown below, is a cyclohexanedione herbicide that provides post-emergence control of annual grasses in many broad-leaved crops.
  • Butroxydim, as well as methods of preparing butroxydim are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Butroxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • butroxydim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 9 g ai/ha or more, such as10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or
  • Clethodim Compositions and methods of the present disclosure can include clethodim or an agriculturally acceptable salt or ester thereof.
  • Clethodim shown below, is a cyclohexanedione herbicide that provides post-emergence control of annual and perennial grasses in a wide range of broad-leaved crops, including such field crops as canola/oilseed rape, soybean, cotton, flax, sunflowers, alfalfa, peanuts, sugar beet, tobacco, and potatoes, as well as vegetable crops, trees, and vines.
  • Clethodim, as well as methods of preparing clethodim are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Clethodim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • clethodim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2 g ai/ha or more, such as 3 g ai/ha or more, 4 g ai/ha or more, 6 g ai/ha or more, 8 g ai/ha or more, 10 g ai/ha or more, 12 g ai/ha or more, 14 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g ai/ha or more, 30 g
  • Clodinafop Compositions and methods of the present disclosure can include clodinafop or an agriculturally acceptable salt or ester thereof.
  • Clodinafop-propargyl shown below, is prop-2- ynyl (R)-2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionate and is used for post- emergence control of annual grasses, including Avena, Lolium, Setaria, Phalaris, and Alopecurus spp., in cereals. .
  • Clodinafop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • clodinafop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 10 g ai/ha or more, such as 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more,15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/
  • Cloproxydim Compositions and methods of the present disclosure can include cloproxydim or an agriculturally acceptable salt or ester thereof.
  • Cloproxydim shown below, is a cyclohexanedione herbicide that has been evaluated by the Chevron Chemical Company. Cloproxydim provides post-emergence control of a wide range of annual and perennial grasses in beans, cotton, potatoes, sugar beets, and most vegetable crops. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Cycloxydim Compositions and methods of the present disclosure can include cycloxydim or an agriculturally acceptable salt or ester thereof.
  • Cycloxydim shown below, is a cyclohexanedione herbicide that provides post-emergence control of annual and perennial grasses (except red fescue and Poa spp.) in canola/oilseed rape, beans, potatoes, brassicas, cotton, celery, fennel, beetroot, sugar beets, fodder beets, sunflowers, soybeans, flax, alfalfa, crucifers, and alliums. Cycloxydim, as well as methods of preparing cycloxydim, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Cycloxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • cycloxydim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190
  • Cyhalofop Compositions and methods of the present disclosure can include cyhalofop or an agriculturally acceptable salt or ester thereof.
  • Cyhalofop as well as methods of preparing cyhalofop, are known in the art.
  • Cyhalofop is an aryloxyphenoxypropionate ester that is used for post-emergence control of grass weeds in rice.
  • Cyhalofop-butyl shown below, is an ester of cyhalofop.
  • Cyhalofop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • cyhalofop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 120 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 180 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, 275
  • Diclofop Compositions and methods of the present disclosure can include diclofop or an agriculturally acceptable salt or ester thereof.
  • Diclofop-methyl shown below, is an aryloxyphenoxypropionate that is used for post-emergence control of wild oats, wild millets, and other annual grass weeds in wheat, barley, rye, red fescue, and broad-leaved crops such as soybeans, sugar beets, fodder beets, flax, legumes, canola/oilseed rape, sunflowers, clover, alfalfa, peanuts, brassicas, carrots, celery, parsnips, lettuce, spinach, potatoes, cucumbers, peas, beans, tomatoes, fennel, alliums, and herbs.
  • Diclofop as well as methods of preparing diclofop, are known in the art. Diclofop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • diclofop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount 100 g ai/ha or more, such as 150 g ai/ha or more, 175 g ai/ha or more, 200 g ai/ha or more, 220 g ai/ha or more, 240 g ai/ha or more, 260 g ai/ha or more, 280 g ai/ha or more, 300 g ai/ha or more, 320 g ai/ha or more, 340 g ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, 400 g ai/ha or more, 420 g ai/ha or more, 440 g ai/ha or more, 460 g ai/ha or more, 480 g ai/ha or more, 500 g ai/ha or
  • Fenoxaprop Compositions and methods of the present disclosure can include fenoxaprop or an agriculturally acceptable salt or ester thereof.
  • Fenoxaprop is an aryloxyphenoxypropionate that is used for post-emergence control of annual and perennial grass weeds in potatoes, beans, soybeans, beets, vegetables, peanuts, and cotton; and (when applied with the herbicide safener fenchlorazole-ethyl) annual and perennial grass weeds and wild oats in wheat, rye, and triticale.
  • Fenoxaprop-P-ethyl shown below, is an ester of fenoxaprop.
  • Fenoxaprop, as well as methods of preparing fenoxaprop are known in the art.
  • Fenoxaprop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • fenoxaprop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 25 g ai/ha or more, such as 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g a
  • Fenthiaprop Compositions and methods of the present disclosure can include fenthiaprop or an agriculturally acceptable salt or ester thereof.
  • Fenthiaprop shown below, is an aryloxyphenoxypropionate herbicide that is used for post-emergence control of many annual and perennial grasses and volunteer cereals in canola/oilseed rape, potatoes, and sugar beets.
  • Fenthiaprop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • fenthiaprop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount 150 g ai/ha or more, such as 160 g ai/ha or more,170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 220 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 280 g ai/ha or more, 300 g ai/ha or more, 320 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, 400 g ai/ha or more, 420 g ai/ha or more
  • Fluazifop Compositions and methods of the present disclosure can include fluazifop or an agriculturally acceptable salt or ester thereof.
  • Fluazifop is an aryloxyphenoxypropionate that is used for post-emergence control of annual and perennial grass weeds in broad-leaved crops, including control of volunteer cereals and other grass weeds in canola/oilseed rape, sugar beet, fodder beet, potatoes, cotton, soybeans, peanuts, pome fruit, bush fruit, vines, citrus fruit, pineapples, bananas, strawberries, sunflowers, alfalfa, coffee, ornamentals and many vegetables.
  • Fluazifop-P-butyl shown below, is an ester of fluazifop.
  • Fluazifop as well as methods of preparing fluazifop, are known in the art. Fluazifop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • fluazifop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 grams active ingredient per hectare (g ai/ha) or more, such as 105 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, 275 g ai/ha or more, 300 g ai/ha or more, 325 g ai/ha or more, 350 g ai/ha or more, 375
  • Haloxyfop Compositions and methods of the present disclosure can include haloxyfop or an agriculturally acceptable salt or ester thereof.
  • Haloxyfop is an aryloxyphenoxypropionate that is used post-emergence for control of annual and perennial grasses in sugar beets, fodder beets, canola/oilseed rape, potatoes, leafy vegetables, onions, flax, sunflowers, soybeans, vines, strawberries and other crops.
  • Haloxyfop-P-methyl shown below, is an ester of haloxyfop; haloxyfop-R-methyl is the racemic form of this herbicide.
  • Haloxyfop, as well as methods of preparing haloxyfop are known in the art.
  • Haloxyfop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • haloxyfop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 24 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g a
  • Metamifop Compositions and methods of the present disclosure can include metamifop.
  • Metamifop shown below, is an aryloxyphenoxypropionate that is used for post-emergence control of annual and perennial grass weeds (including Echinochloa spp., Leptochloa chinensis, Digitaria spp. and Eleusine indica) in rice, wheat, soybeans, cotton, and turf grass.
  • Metamifop as well as methods of preparing metamifop, are known in the art. Metamifop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • metamifop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 105 g ai/ha or more, 110 g ai/ha or more, 115 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 135 g ai/ha or more, 140 g ai/ha or more, 145
  • Pinoxaden Compositions and methods of the present disclosure can include pinoxaden or an agriculturally acceptable salt or ester thereof.
  • Pinoxaden shown below, is a phenylpyrazoline herbicide that provides post-emergence control of grass weeds in wheat, barley, lawns, and turf.
  • Pinoxaden, as well as methods of preparing pinoxaden are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Pinoxaden can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pinoxaden is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2 g ai/ha or more, such as 2.5 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 8 g ai/ha or more, 10 g ai/ha or more, 12 g ai/ha or more, 14 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more
  • Profoxydim Compositions and methods of the present disclosure can include profoxydim or an agriculturally acceptable salt or ester thereof.
  • Profoxydim shown below, is a cyclohexanedione herbicide.
  • Profoxydim is used for control of grass weeds, including Echinochloa spp., Brachiaria spp., Digitaria spp., Eleusine spp., Leptochloa spp., Setaria spp., Ischaemum rugosum and Rottboellia exaltata, in rice.
  • Profoxydim, as well as methods of preparing profoxydim are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Profoxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • profoxydim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 105 g ai/ha or more, 110 g ai/ha or more, 115 g ai/ha or more, 120 g ai/ha or more, 125 g g
  • Propaquizafop Compositions and methods of the present disclosure can include propaquizafop.
  • Propaquizafop shown below, is an aryloxyphenoxypropionate that is to control a wide range of annual and perennial grasses in soybeans, cotton, sugar beets, potatoes, peanuts, peas, canola/oilseed rape and vegetables.
  • Propaquizafop, as well as methods of preparing propaquizafop are known in the art.
  • Propaquizafop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • propaquizafop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 29 g ai/ha or more, such as 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/
  • Quizalofop Compositions and methods of the present disclosure can include quizalofop or an agriculturally acceptable salt or ester thereof.
  • Quizalofop is an aryloxyphenoxypropionate that is used for selective post-emergence control of annual and perennial grass weeds in potatoes, soybeans, sugar beets, peanuts, canola/oilseed rape, sunflowers, vegetables, cotton and flax.
  • Quizalofop-P-ethyl shown below, is an ester of quizalofop.
  • Quizalofop, as well as methods of preparing quizalofop, are known in the art.
  • Quizalofop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • quizalofop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 24 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g a
  • Sethoxydim Compositions and methods of the present disclosure can include sethoxydim or an agriculturally acceptable salt or ester thereof.
  • Sethoxydim shown below, is a cyclohexanedione herbicide that is used for controlling annual and perennial grasses in broad- leaved crops, including canola/oilseed rape, soybean, cotton, fodder beets, sunflowers, spinach, potatoes, tobacco, peanuts, strawberries, alfalfa, flax, vegetables, and sugar beet.
  • Sethoxydim, as well as methods of preparing sethoxydim are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Sethoxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • sethoxydim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2 g ai/ha or more, such as 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 8 g ai/ha or more, 10 g ai/ha or more, 12 g ai/ha or more, 14 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g a
  • Tepraloxydim Compositions and methods of the present disclosure can include tepraloxydim or an agriculturally acceptable salt or ester thereof.
  • Tepraloxydim shown below, is a cyclohexanedione herbicide that is used for broad-spectrum post-emergence grass weed control, especially Poa annua and volunteer maize, and also Sorghum halepense and Elymus repens, in broad-leaved crops.
  • Tepraloxydim, as well as methods of preparing tepraloxydim are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Tepraloxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • tepraloxydim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 25 g ai/ha or more, such as 27.5 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more,
  • Tralkoxydim Compositions and methods of the present disclosure can include tralkoxydim or an agriculturally acceptable salt or ester thereof.
  • Tralkoxydim is a cyclohexanedione herbicide that has the chemical name 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-mesitylcyclohex-2-enone, and has the following structure: Tralkoxydim is used for post-emergence control of annual grass weeds (including Avena spp., Lolium spp., Setaria viridis, Phalaria spp., Alopecurus myosuroides, and Apera spica-venti) in wheat and barley.
  • Tralkoxydim as well as methods of preparing tralkoxydim, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Tralkoxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 95 g ai/ha or more, such as 100 g ai/ha or more, 105 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more,
  • compositions can include a plant growth regulator (PGR), an agriculturally acceptable salt or ester thereof, or mixtures thereof.
  • PGRs also called plant hormones, act as chemical messengers for intercellular communication. PGRs can be classified into a number of modes of action that may influence, for example, the growth, division, elongation, or differentiation of plant cells.
  • PGRs examples include 1,4- dimethylnapththalene, 1-methylcyclopropene, 1-napthylacetic acid, 2,6- diisopropylnaphthalene, 2-naphthyloxyacetic acid, 4-chlorophenoxyacetic acid (4-CPA), 6- benzylaminopurine, abscisic acid, amidochlor, ancymidol, aviglycine, butralin, carbaryl, chlorflurenol, chlormequat, chlorphonium chloride, chlorpropham, clofencet, cloprop, cloxyfonac, cuprous chloride, cyanamide, cyclanilide, cycloheximide, cytokinins, daminozide, decan-1-ol, dikegulac, dimethipin, dimexano, endothal, et reviewingl, ethephon, ethychlozate, fenoprop, fenridazon, flume
  • the composition can include a PGR selected from the group consisting of 1,4-dimethylnapththalene, 1-methylcyclopropene, 1-napthylacetic acid, 2,6- diisopropylnaphthalene, 2-naphthyloxyacetic acid, 4-chlorophenoxyacetic acid (4-CPA), 6- benzylaminopurine, abscisic acid, amidochlor, ancymidol, aviglycine, butralin, carbaryl, chlorflurenol, chlormequat, chlorphonium chloride, chlorpropham, clofencet, cloprop, cloxyfonac, cuprous chloride, cyanamide, cyclanilide, cycloheximide, cytokinins, daminozide, decan-1-ol, dikegulac, dimethipin, dimexano, endothal, et messagingl, ethephon, ethychlozate,
  • PGRs can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the PGR is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 0.020 g ai/ha or more, such as 0.025 g ai/ha or more, 0.03 g ai/ha or more, 0.04 g ai/ha or more, 0.05 g ai/ha or more, 0.06 g ai/ha or more, 0.07 g ai/ha or more, 0.08 g ai/ha or more, 0.09 g ai/ha or more, 0.1 g ai/ha or more, 0.11 g ai/ha or more, 0.125 g ai/ha or more, 0.15 g ai/ha or more, 0.175
  • 1,4-Dimethylnaphthalene Compositions and methods of the present disclosure can include 1,4- dimethylnaphthalene or an agriculturally acceptable salt or ester thereof.
  • 1,4- Dimethylnaphthalene shown below, is an aromatic hydrocarbon that provides inhibition of sprouting in potatoes after packaging, during shipping and in storage or in seed potatoes, at a spray rate of 5-20 mg/kg of potatoes.
  • 1,4-Dimethylnaphthalene, as well as methods of preparing 1,4-dimethylnaphthalene are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • 1-Methylcyclopropene Compositions and methods of the present disclosure can include 1- methylcyclopropene or an agriculturally acceptable salt or ester thereof.
  • 1- Methylcyclopropene shown below, is a cyclic hydrocarbon that extends the life of cut and potted flowering plants and of harvested fruit and vegetables. It is formulated as a powder and released as a gas when the product is added to water.
  • 1-Methylcyclopropene, as well as methods of preparing 1-methylcyclopropene are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • 1-Methylcyclopropene can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • 1-methylcyclopropene is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 5 g ai/ha or more, such as 5.25 g ai/ha or more, 5.5 g ai/ha or more, 5.75 g ai/ha or more, 6 g ai/ha or more, 6.25 g ai/ha or more, 6.5 g ai/ha or more, 6.75 g ai/ha or more, 7 g ai/ha or more, 7.25 g ai/ha or more, 7.5 g ai/ha or more, 8 g ai/ha or more, 8.5 g ai/ha or more, 9 g ai/ha or more,
  • 1-Naphthylacetic acid Compositions and methods of the present disclosure can include 1-naphthylacetic acid or an agriculturally acceptable salt or ester thereof.
  • 1-Naphthylacetic acid shown below, is a naphthylacetic acid that: stimulates root formation in cuttings of woody and herbaceous plants and vines at 0.1-0.6 g/plant; prevents premature flower and fruit drop in apples, pears, grapes, guavas, mangoes, watermelons, pawpaws, citrus, aubergines, cucumbers, cotton, soybeans, etc.; increases fruit setting; provides thinning of fruit in apples, pears, olives, citrus and other fruit; and induces flowering in pineapples.
  • 1-Naphthylacetic acid as well as methods of preparing 1-naphthylacetic acid, are known in the art.
  • Exemplary salts of 1-Naphthylacetic acid include ammonium 1-Naphthylacetic acetate, sodium 1-Naphthylacetic acetate, and potassium 1-Naphthylacetic acetate, while esters include ethyl 1-Naphthylacetic acetate. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • 1-Naphthylacetic acid can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • 1-naphthylacetic acid is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 g ai/ha or more, such as 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more, 2
  • 2,6-Diisopropylnaphthalene Compositions and methods of the present disclosure can include 2,6- diisopropylnaphthalene or an agriculturally acceptable salt or ester thereof.
  • 2,6- Diisopropylnaphthalene shown below, is an aromatic hydrocarbon that inhibits sprouting in potatoes, at a spray rate of 2.5-25 mg/kg of potatoes.
  • 2,6-Diisopropylnaphthalene, as well as methods of preparing 2,6-diisopropylnaphthalene are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • 2-Naphthyloxyacetic acid Compositions and methods of the present disclosure can include 2- naphthyloxyacetic acid or an agriculturally acceptable salt or ester thereof.
  • 2- Naphthyloxyacetic acid shown below, is a phenoxycarboxylic acid that increases fruit setting in tomatoes, strawberries, blackberries, peppers, aubergines, grapes and pineapples.
  • 2- Naphthyloxyacetic acid, as well as methods of preparing 2-naphthyloxyacetic acid are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • 4-Chlorophenoxyacetic acid (4-CPA) Compositions and methods of the present disclosure can include 4- chlorophenoxyacetic acid (4-CPA) or an agriculturally acceptable salt or ester thereof.
  • 4-CPA shown below, is a phenoxycarboxylic acid that improves fruit setting in tomatoes, by application to the flowers, at 1.5–3 g/hl of spray solution; inhibition of sprout formation in mung beans; thinning of fruit in peaches.
  • 4-CPA as well as methods of preparing 4-CPA, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • 6-Benzylaminopurine Compositions and methods of the present disclosure can include 6- benzylaminopurine or an agriculturally acceptable salt or ester thereof.
  • 6-Benzylaminopurine shown below, is a aminopurine that stimulates lateral bud emergence in apples, pears and oranges, formation of basal shoots in roses and orchids, flowering in cyclamens and cacti, fruit set in grapes, oranges and melons, fruit thinning, flower bud formation and regular bearing in tree fruit, inhibition of senescence in rice seedlings, enhancement of lateral bud break and shoot growth in white pine trees, uniform bolting and increased seed production in spinach, all by foliar application, soaking, or painting, at 75 g/ha in apples.
  • 6-Benzylaminopurine as well as methods of preparing 6-benzylaminopurine, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. 6-Benzylaminopurine can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • 6-benzylaminopurine is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 10 g ai/ha or more, such as 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g
  • Abscisic acid Compositions and methods of the present disclosure can include abscisic acid or an agriculturally acceptable salt or ester thereof.
  • Abscisic acid shown below, is a plant hormone that reduces drought stress and controls wilting in ornamental plants; decreases water requirements during shipping of ornamental plants; accelerates and enhances the color development of grapes, using a spray solution at 7.5-50 g/hl concentration. Abscisic acid, as well as methods of preparing abscisic acid, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Abscisic acid can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • abscisic acid is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 75 g ai/ha or more, such as 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180
  • Ancymidol Compositions and methods of the present disclosure can include ancymidol or an agriculturally acceptable salt or ester thereof.
  • Ancymidol shown below, is a pyrimidine carbinol used to reduce internode elongation to produce more compact greenhouse plants, by application to either foliage or soil, at 0.6–6.6 g/hl for bedding plants, 0.3–3.5 g/hl for bedding plant plugs, 2–5 g/hl for flowering and foliage plants, 2.5–5 g/hl for bulbs.
  • Ancymidol, as well as methods of preparing ancymidol are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Aviglycine Compositions and methods of the present disclosure can include aviglycine or an agriculturally acceptable salt or ester thereof.
  • Aviglycine shown below, is an amino acid used to reduce fruit drop, reduce delay of fruit maturity, reduce delay or extension of harvest, improve harvest management, maintain fruit quality (e.g. fruit firmness), enhance size and color as a result of delayed harvest, reduce incidence and/or severity of watercore and superficial scald, enhance storage potential in apples, pears, stone fruit and walnuts and increase nut set in walnut cultivars affected by pistillate flower abortion.
  • Aviglycine, as well as methods of preparing aviglycine are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Aviglycine can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • aviglycine is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 200 g ai/ha or more, such as 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g ai/ha or more, 275 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/ha or more, 310 g ai/ha or more, 320 g a
  • Butralin Compositions and methods of the present disclosure can include butralin or an agriculturally acceptable salt or ester thereof.
  • Butralin shown below, is a dinitroaniline used for pre-emergence control of annual broad-leaved and grass weeds in cotton, soybeans, rice, barley, beans, alliums, vines, ornamentals, fruit and nut trees, at 1120–3400 g/ha; control of suckers in tobacco, at 125 mg/plant.
  • Butralin, as well as methods of preparing butralin are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Butralin can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • butralin is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1100 g ai/ha or more, such as 1120 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1800 g ai/ha or more, 1900 g ai/ha or more, 2000 g ai/ha or more
  • Chlorflurenol Compositions and methods of the present disclosure can include chlorflurenol or an agriculturally acceptable salt or ester thereof.
  • Chlorflurenol shown below, is a polycyclic aromatic carboxylic acid used as a growth retardant, at 2000–4000 g/ha, and for weed suppression, at 500–1500 g/ha as a soil application, in amenity grass, roadsides, railways, ditch banks, etc.
  • Chlorflurenol also increases yield and improve size grading in pickling cucumbers, and induces vegetative planting material in pineapples. Chlorflurenol, as well as methods of preparing chlorflurenol, are known in the art.
  • Chlorflurenol can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • chlorflurenol is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 500 g ai/ha or more, such as 525 g ai/ha or more, 550 g ai/ha or more, 575 g ai/ha or more, 600 g ai/ha or more, 625 g ai/ha or more, 650 g ai/ha or more, 675 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g
  • Chlormequat chloride Compositions and methods of the present disclosure can include chlormequat chloride.
  • Chlormequat chloride shown below, is a quaternary ammonium salt used to: increase resistance to lodging and increase yields in wheat, rye, oats and triticale, at 800–1600 g/ha; promote lateral branching and flowering in azaleas, fuchsias, begonias, poinsettias, geraniums, pelargoniums and other ornamental plants; promote flower formation and improve fruit setting in pears, almonds, vines, olives and tomatoes; and prevent premature fruit drop in pears, apricots and plums.
  • Chlormequat chloride as well as methods of preparing chlormequat chloride, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. Chlormequat chloride can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • chlormequat chloride is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 500 g ai/ha or more, such as 525 g ai/ha or more, 550 g ai/ha or more, 575 g ai/ha or more, 600 g ai/ha or more, 625 g ai/ha or more, 650 g ai/ha or more, 675 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200
  • Chlorpropham Compositions and methods of the present disclosure can include chlorpropham or an agriculturally acceptable salt or ester thereof.
  • Chlorpropham shown below, is a quaternary ammonium salt used to inhibit sprouting in stored potatoes, at 8–64 g/t and control suckers in tobacco.
  • Chlorpropham is also used for pre-emergence control of annual grass and some broad- leaved weeds in onions, leeks, garlic, shallots, alfalfa, clover, sugar beets, spinach, lettuce, endive, chicory, herbs, peas, beans, carrots, celery, black salsify, fennel, soybeans, cotton, rice, safflowers, sunflowers, cranberries, cane berries, ornamentals, ornamental trees and shrubs, perennial grass seed crops, etc., at up to 240 g/ha. Chlorpropham, as well as methods of preparing chlorpropham, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Chlorpropham can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • chlorpropham is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 15 g ai/ha or more, such as 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or
  • Clofencet Compositions and methods of the present disclosure can include clofencet or an agriculturally acceptable salt or ester thereof.
  • Clofencet shown below, is a pyridazinecarboxylic acid used as a chemical hybridizing agent for wheat, at 3000-5000 g/h as the potassium salt.
  • Clofencet, as well as methods of preparing clofencet are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Cloprop Compositions and methods of the present disclosure can include cloprop or an agriculturally acceptable salt or ester thereof.
  • Cloprop shown below, is a phenoxycarboxylic acid used to reduce crown growth in pineapples, in order to increase the fruit size and weight and to delay maturation, and also for thinning of fruit in certain plum varieties. Cloprop, as well as methods of preparing cloprop, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. Cloprop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • cloprop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 g ai/ha or more, such as 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more
  • Cloxyfonac Compositions and methods of the present disclosure can include cloxyfonac or an agriculturally acceptable salt or ester thereof.
  • Cloxyfonac shown below, is a phenoxycarboxylic acid used for fruit setting in tomatoes and aubergines at flowering, producing fruit of uniform size. Cloxyfonac, as well as methods of preparing cloxyfonac, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. Cyanamide Compositions and methods of the present disclosure can include cyanamide or an agriculturally acceptable salt or ester thereof.
  • Cyanamide shown below, is an inorganic compound used for early post-emergence control of broad-leaved weeds in alliums (onions, leeks, chives, shallots and garlic) and bulb flowers. Cyanamide is also used for promotion of bud break and increase of flowering in kiwifruit and apples, and removal of side shoots and inhibition of sprouting in hops and vines. Cyanamide, as well as methods of preparing cyanamide, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. Cyanamide can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • cyanamide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 kg ai/ha or more, such as 1.1 kg ai/ha or more, 1.25 kg ai/ha or more, 1.5 kg ai/ha or more, 1.75 kg ai/ha or more, 2 kg ai/ha or more, 2.25 kg ai/ha or more, 2.5 kg ai/ha or more, 2.75 kg ai/ha or more, 3 kg ai/ha or more, 3.25 kg ai/ha or more, 3.5 kg ai/ha or more, 3.75 kg ai/ha or more, 4 kg ai/ha or more, 4.25 kg ai/ha or more, 4.5 kg ai/ha or more, or 4.75 kg ai/ha or more; in an amount of 5 kg ai/ha or less, such as 4.75 kg ai/ha or less, 4.5 kg ai/ha or more;
  • Cyclanilide Compositions and methods of the present disclosure can include cyclanilide or an agriculturally acceptable salt or ester thereof.
  • Cyclanilide shown below, is cyclopropane carboxylic acid used for promotion of boll opening, defoliation and inhibition of terminal foliar regrowth in cotton. Cyclanilide, as well as methods of preparing cyclanilide, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. Cyclanilide can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • cyclanilide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 3 g ai/ha or more, such as 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.25 g ai/ha or more, 5.5 g ai/ha or more, 5.75 g ai/ha or more, 6 g ai/ha or more, 6.25 g ai/ha or more, 6.5 g ai/ha or more, 6.75 g ai/ha or more, 7 g ai/ha or more, 7.25 g ai/ha or more, 7.5 g
  • Cytokinins Compositions and methods of the present disclosure can include the cytokinins, such as 6-isopentenylaminopurine, zeatin, and kinetin, or agriculturally acceptable salts or esters thereof.
  • cytokinins such as 6-isopentenylaminopurine, zeatin, and kinetin, or agriculturally acceptable salts or esters thereof.
  • These cytokinins shown below, are purines that enhance germination, flowering, fruit and seed set, induction of callus initiation, reduction of apical dominance, breaking lateral bud dormancy and retarding of aging in vegetables, peas, beans, tree fruit, vines, ornamentals, flowers, containerized plants, lawn and turf. Cytokinins, as well as methods of preparing cytokinins, are known in the art.
  • Cytokinins can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • cytokinins are applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 0.02 g ai/ha or more, such as 0.025 g ai/ha or more, 0.03 g ai/ha or more, 0.04 g ai/ha or more, 0.05 g ai/ha or more, 0.06 g ai/ha or more, 0.07 g ai/ha or more, 0.08 g ai/ha or more, 0.09 g ai/ha or more, 0.1 g ai/ha or more, 0.11 g ai/ha or more, 0.125 g ai/ha or more, 0.15 g ai/ha or more, 0.175 g ai/ha or more, 0.20 g ai/ha or more, 0.25 g ai/ha or more, 0.3 g ai/ha or more, 0.4 g ai/ha
  • Daminozide Compositions and methods of the present disclosure can include daminozide or an agriculturally acceptable salt or ester thereof.
  • Daminozide shown below, is succinamic acid used for inhibition of internodal elongation, to produce more compact plants, in chrysanthemums, azaleas, hydrangeas, poinsettias and other ornamentals, at 106–425 g/ha.
  • Daminozide, as well as methods of preparing daminozide are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Daminozide can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • daminozide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 g ai/ha or more, such as 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more
  • Decan-1-ol Compositions and methods of the present disclosure can include decan-1-ol or an agriculturally acceptable salt or ester thereof.
  • Decan-1-ol shown below, is a fatty alcohol used for control of sucker growth in tobacco, at 11000–17000 g/ha.
  • Decan-1-ol, as well as methods of preparing decan-1-ol, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. Decan-1-ol can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • decan-1-ol is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 10 kg ai/ha or more, such as 10.5 kg ai/ha or more, 11 kg ai/ha or more, 11.5 kg ai/ha or more, 12 kg ai/ha or more, 12.5 kg ai/ha or more, 13 kg ai/ha or more, 13.5 kg ai/ha or more, 14 kg ai/ha or more, 14.5 kg ai/ha or more, 15 kg ai/ha or more, 15.5 kg ai/ha or more, 16 kg ai/ha or more, 16.5 kg ai/ha or more, or 16.75 kg ai/ha or more; in an amount of 17 kg ai/ha or less, such as 16.75 kg ai/ha or less, 16.5 kg ai/ha or less, 16 kg ai/ha or less, 15.5 kg ai/
  • Dikegulac Compositions and methods of the present disclosure can include dikegulac or an agriculturally acceptable salt or ester thereof.
  • Dikegulac shown below, is a plant growth regulator used for reducing apical dominance and promotion of side-branching and flower-bud formation in azaleas, fuchsias and other ornamental plants, and to temporarily retard longitudinal growth in hedges and ornamental shrubs; also for growth retardant in trees by trunk injection.
  • Dikegulac, as well as methods of preparing dikegulac are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Dimethipin Compositions and methods of the present disclosure can include dimethipin or an agriculturally acceptable salt or ester thereof.
  • Dimethipin shown below, is a dithiine used for: defoliation of cotton, nursery stock, rubber trees and vines, at 260-720 g/ha; destruction of potato haulm, at 480-720 g/ha; and reduction of seed moisture content at harvest in maize, rice, oilseed rape, flax and sunflowers, at 240-720 g/ha.
  • Dimethipin, as well as methods of preparing dimethipin are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Dimexano Compositions and methods of the present disclosure can include dimexano or an agriculturally acceptable salt or ester thereof.
  • Dimexano shown below, is a thiocarbamate used for: pre-emergence control of broad-leaved weeds in drilled crops, at 9000 g/ha; pre- harvest desiccant for onions and peas, at 28000 g/ha; and control of growth and splitting of carrots.
  • Dimexano, as well as methods of preparing dimexano are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. Endothall Compositions and methods of the present disclosure can include endothall or an agriculturally acceptable salt or ester thereof.
  • Endothall is a bicyclocarboxylic acid used for: pre- and post-emergence control of annual grass and broad-leaved weeds in sugar beets, fodder beets, beetroot, spinach and turf, at 2000–6000 g/ha; control of algae and aquatic weeds at 1-5 ppm; desiccant for alfalfa, clover and hops; defoliant in cotton; and destruction of potato haulms.
  • Endothall, as well as methods of preparing endothall are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Endothall can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • endothall is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 600 g ai/ha or more, such as 625 g ai/ha or more, 650 g ai/ha or more, 675 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/
  • Ethephon Compositions and methods of the present disclosure can include ethephon or an agriculturally acceptable salt or ester thereof.
  • Ethephon shown below, is a phosphonate used for; promotion of pre-harvest ripening in apples, currants, blackberries, blueberries, cranberries, morello cherries, citrus, figs, tomatoes, sugar beet and fodder beet seed crops, coffee and peppers; acceleration of post-harvest ripening in bananas, mangoes and citrus; loosening of fruit in currants, gooseberries, cherries and apples; increase flower bud development in apples; prevention of lodging in cereals, maize and flax; induction of flowering in Bromeliads; stimulation of lateral branching in azaleas, geraniums and roses; shortening of stem length in forced daffodils; induction of flowering and regulation of ripening in pineapples; accelerate of boll opening in cotton; modification of sex expression in cucumbers and squash; increase fruit setting and
  • Ethephon as well as methods of preparing ethephon, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. Ethephon can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • ethephon is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 125 g ai/ha or more, such as 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g ai/ha or more, 275 g ai
  • Fenoprop Compositions and methods of the present disclosure can include fenoprop or an agriculturally acceptable salt or ester thereof.
  • Fenoprop shown below, is a phenoxycarboxylic acid used for postemergence brush control, at 2000-4000 g/hl spray solution; control of aquatic weeds; control of broad-leaved weeds in maize and sugar cane; and reduction of pre-harvest apple drop, at 1400 g ae/hl of amine salt spray solution 7-14 d prior to harvest.
  • Fenoprop, as well as methods of preparing fenoprop are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Flumetralin Compositions and methods of the present disclosure can include flumetralin or an agriculturally acceptable salt or ester thereof.
  • Flumetralin shown below, is a dinitroaniline used for control of sucker growth in tobacco. Flumetralin, as well as methods of preparing flumetralin, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. Flumetralin can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • flumetralin is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 650 g ai/ha or more, such as 675 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, or 1300 g ai/ha or more; in an amount of 1350 g ai/ha or less, such as 1300 g ai/ha or less, 1250 g ai/ha or more
  • Flurenol Compositions and methods of the present disclosure can include flurenol or an agriculturally acceptable salt or ester thereof.
  • Flurenol shown below, is a carboxylic acid used for post-emergence control of broad-leaved weeds in cereals, including wheat, barley, rye, oats, and rice. Flurenol, as well as methods of preparing flurenol, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. Flurenol can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • flurenol is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 200 g ai/ha or more, such 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g ai/ha or more, 275 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/ha or more, 310 g ai/ha or more, 320 g ai/ha or more, 325 g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350 g ai/
  • Flurprimidol Compositions and methods of the present disclosure can include flurprimidol or an agriculturally acceptable salt or ester thereof.
  • Flurprimidol shown below, is a pyrimidine carbinol used to decrease the rate of growth of plants, including perennial turf grasses, ornamental cover species, herbaceous and woody ornamentals and deciduous and coniferous trees, at 140–1100 g/ha in turf grasses, 560–1100 g/ha in flowering and foliage plants, 1100– 3400 g/ha in woody ornamentals.
  • Flurprimidol, as well as methods of preparing flurprimidol are known in the art.
  • Flurprimidol can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • flurprimidol is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 125 g ai/ha or more, such as 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g ai/ha or more, 275 g g g
  • Forchlorfenuron Compositions and methods of the present disclosure can include forchlorfenuron or an agriculturally acceptable salt or ester thereof.
  • Forchlorfenuron shown below, is a phenyl urea used for: increasing the size of kiwifruit, table grapes and peaches; promotion of fruit set in melons, pumpkins and cucumbers; promotion of branching in apples; increasing yields in potatoes, rice and wheat.
  • Forchlorfenuron, as well as methods of preparing forchlorfenuron are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Forchlorfenuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • forchlorfenuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 4 g ai/ha or more, such as 4.25 g ai/ha or more, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.25 g ai/ha or more, 5.5 g ai/ha or more, 5.75 g ai/ha or more, 6 g ai/ha or more, 6.25 g ai/ha or more, 6.5 g ai/ha or more, 6.75 g ai/ha or more, 7 g ai/ha or more, 7.25 g ai/ha or more, 7.5
  • Gibberellins Compositions and methods of the present disclosure can include gibberellins, including gibberellic acid, gibberellin A4, and gibberellin A7, or an agriculturally acceptable salt or ester thereof.
  • Gibberellins shown below, are natural plant compounds used to: improve fruit setting in clementines and pears; loosen and elongate clusters and increase berry size in grapes; control fruit maturity by delaying development of the yellow color in lemons; reduce rind stain and retard rind ageing in navel oranges; promote uniform seedling growth in rice; promote elongation in winter celery; induce uniform bolting and increase seed production in lettuce; stimulate sprouting in seed potatoes; hasten maturation in artichokes; increase yields in forced rhubarb; increase malting quality in barley; produce brighter-colored, firmer fruit and increase fruit size in sweet cherries; increase yields and aid harvesting in hops; reduce internal browning and increase yields in Italian prunes; increase fruit set and yields in tangelos and tanger
  • Gibberellins as well as methods of preparing gibberellins, are known in the art. Their plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. gibberellic acid Gibberellins can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • gibberellins are applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 1.1 g ai/ha or more, 1.25 g ai/ha or more, 1.5 g ai/ha or more, 1.75 g ai/ha or more, 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 g ai/ha or more, 4.5 g ai/ha or more, 4.75 g ai/ha or more, 5 g ai/ha or more, 5.25 g a
  • Heptamaloxyloglucan Compositions and methods of the present disclosure can include heptamaloxyloglucan or an agriculturally acceptable salt or ester thereof.
  • Heptamaloxyloglucan shown below, is a polysaccharide used as a plant elicitor for protection of grapes from spring frost damage. Heptamaloxyloglucan, as well as methods of preparing heptamaloxyloglucan, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Indol-3-butyric acid (IBA) and Indol-3-ylacetic acid (IAA) Compositions and methods of the present disclosure can include indol-3-butyric acid (IBA), indol-3-ylacetic acid (IAA) or an agriculturally acceptable salt or ester thereof.
  • IBA and IAA shown below, are plant hormones used to stimulate rooting of cuttings of herbaceous and woody ornamentals. IBA and IAA, as well as methods of preparing IBA and IAA, are known in the art. Their plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • IBA or IAA can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • IBA or IAA are applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 105 g ai/ha or more, 110 g ai/ha or more, 115 g ai/ha or more, 120 g ai/ha or more, 125
  • Isoprothiolane Compositions and methods of the present disclosure can include isoprothiolane or an agriculturally acceptable salt or ester thereof.
  • Isoprothiolane shown below, is a dithiolane used to accelerate rooting, promote root elongation, and control non-parasitic damping-off in rice.
  • Isoprothiolane, as well as methods of preparing isoprothiolane, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Maleic hydrazide Compositions and methods of the present disclosure can include maleic hydrazide or an agriculturally acceptable salt or ester thereof.
  • Maleic hydrazide shown below, is a pyridazine used for: suppression of grass growth in lawns, roadside verges, embankments and amenity areas and of growth of shrubs and trees; inhibition of sprouting in potatoes, onions, beets, swedes, parsnips and carrots in storage; prevention of sucker development in tobacco; induction of dormancy in citrus, at 1200–5400 g/ha.
  • Maleic hydrazide, as well as methods of preparing maleic hydrazide are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Maleic hydrazide can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • maleic hydrazide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1000 g ai/ha or more, such as 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1800 g ai/ha or more, 1900 g
  • Mefluidide Compositions and methods of the present disclosure can include mefluidide or an agriculturally acceptable salt or ester thereof.
  • Mefluidide shown below, is a sulfonanilide used for: inhibition of growth and suppression of seed production of perennial grasses in turf, lawns, grassland, industrial areas, amenity areas, roadside verges and embankments; inhibition of growth of ornamental trees and shrubs; enhancement of the sucrose content of sugar cane, at 300 to 1100 g/ha; and control of growth and seed production of weeds, particularly Sorghum halepense and volunteer cereals, in soybeans and other crops.
  • Mefluidide, as well as methods of preparing mefluidide are known in the art.
  • Mefluidide can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • mefluidide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 200 g ai/ha or more, such as 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g ai/ha or more, 275 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/ha or more, 310 g ai/ha or more, 320 g ai/ha or more, 325 g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350
  • Mepiquat Compositions and methods of the present disclosure can include the mepiquat ion or an agriculturally acceptable salt thereof.
  • Mepiquat shown below as the chloride or pentaborate salt, is a quaternary ammonium ion used for: reduction of vegetative growth and promotion of boll maturation in cotton, at up to 75 g/ha; inhibition of sprouting in onions, garlic and leeks; prevention of lodging, by shortening the stem and strengthening the stem wall, in cereals, grass seed crops and flax, at up to 762.5 g/ha.
  • Mepiquat, as well as methods of preparing mepiquat are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Mepiquat can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • mepiquat is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 5 g ai/ha or more, such as 6 g ai/ha or more, 7 g ai/ha or more, 7.5 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g a
  • N-Acetylthiazolidine-4-carboxylic acid Compositions and methods of the present disclosure can include N- acetylthiazolidine-4-carboxylic acid or an agriculturally acceptable salt or ester thereof.
  • N- Acetylthiazolidine-4-carboxylic acid shown below, is a carboxylic acid used to increase size of fruit, berries and kernels, increase yield, increase vitamins and improve skin color, using a spray solution at 20-75 ppm concentration.
  • N-Acetylthiazolidine-4-carboxylic acid, as well as methods of preparing N-acetylthiazolidine-4-carboxylic acid, are known in the art.
  • Naphthaleneacetamide Compositions and methods of the present disclosure can include naphthaleneacetamide or an agriculturally acceptable salt or ester thereof.
  • Naphthaleneacetamide shown below, is an aromatic amide used to: stimulate root production at 0.1-0.6 g/plant; thin fruit in apples and pears; and prevent premature fruit fall in apples and cherries.
  • Naphthaleneacetamide, as well as methods of preparing naphthaleneacetamide are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Nitrophenolates Compositions and methods of the present disclosure can include the nitrophenolate mixture (sodium 5-nitroguaiacolate, sodium o-nitrophenolate, and sodium p-nitrophenolate) or an agriculturally acceptable salt or ester thereof.
  • Nitrophenolates shown below, are a mixture of phenolate salts used to increase nutrient uptake in cotton, cereals, cucumbers, grapes, melons, paprika, rice, soybeans, sugar beets and vegetables, at 3–6 g/ha. Nitrophenolates, as well as methods of preparing nitrophenolates, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Nitrophenolates can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • nitrophenolates are applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 1.1 g ai/ha or more, 1.25 g ai/ha or more, 1.5 g ai/ha or more, 1.75 g ai/ha or more, 2 g ai/ha or more, 2.25 g ai/ha or more, 2.5 g ai/ha or more, 2.75 g ai/ha or more, 3 g ai/ha or more, 3.25 g ai/ha or more, 3.5 g ai/ha or more, 3.75 g ai/ha or more, 4 g ai/ha or more, 4.25 g ai/ha or more,
  • Paclobutrazol Compositions and methods of the present disclosure can include paclobutrazol or an agriculturally acceptable salt or ester thereof.
  • Paclobutrazol shown below, is triazole used for: inhibition of vegetative growth and enhancement of fruit set in tree fruit; inhibition of growth in pot-grown ornamentals and flowers, e.g. chrysanthemums, begonias, freesias, poinsettias and bulbs, as a spray at a concentration of 1-200 ppm; prevent lodging and increase yield in rice; growth retardation in turf and reduction of height and prevention of lodging in grass seed crops and oilseed rape.
  • Paclobutrazol, as well as methods of preparing paclobutrazol are known in the art.
  • Paclobutrazol can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • paclobutrazol is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 40 g ai/ha or more, such as 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g a
  • Pelargonic acid Compositions and methods of the present disclosure can include pelargonic acid or an agriculturally acceptable salt or ester thereof.
  • Pelargonic acid shown below, is fatty acid used for: thinning of blossoms in apples and pears; control of annual weeds in potatoes and peanuts; total weed control in non-crop areas; control of mosses in lawns and other domestic areas.
  • Pelargonic acid, as well as methods of preparing pelargonic acid are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Pelargonic acid can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pelargonic acid is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 750 g ai/ha or more, such as 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1800 g
  • Prohexadione Compositions and methods of the present disclosure can include prohexadione or an agriculturally acceptable salt or ester thereof, particularly the calcium salt.
  • Prohexadione shown below, is fatty acid used for: control of lodging in small-grain cereals, at 75–100 g/ha; growth retardant in turf, at 200–400 g/ha, peanuts, at 100–300 g/ha, and flowers, at 50–100 g/ha; inhibition of new twig elongation in tree fruit, at 200–400 g/ha.
  • Prohexadione, as well as methods of preparing prohexadione are known in the art.
  • prohexadione is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 15 g ai/ha or more, such as 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g
  • Prohydrojasmon Compositions and methods of the present disclosure can include prohydrojasmon or an agriculturally acceptable salt or ester thereof.
  • Prohydrojasmon shown below, is a synthetic plant hormone used for: prevention of rind puffing in Satsuma mandarin oranges and promotion of red color development in apples.
  • Prohydrojasmon, as well as methods of preparing prohydrojasmon are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Propham Compositions and methods of the present disclosure can include propham or an agriculturally acceptable salt or ester thereof.
  • Propham is a carbamate used for control of annual grass and some broad-leaved weeds in alfalfa, clover, sugar beets, spinach, lettuce, peas, beans, flax, safflowers, beetroot, fodder beets, lettuce, chard, lentils and perennial grass seed crops, at 2300–5000 g/ha, and as a sprouting inhibitor in potatoes.
  • Propham, as well as methods of preparing propham are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Propham can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • propham is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2000 g ai/ha or more, such as 2100 g ai/ha or more, 2200 g ai/ha or more, 2300 g ai/ha or more, 2400 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2700 g ai/ha or more, 2800 g ai/ha or more, 2900 g ai/ha or more, 3000 g ai/ha or more, 3100 g ai/ha or more, 3200 g ai/ha or more, 3250 g ai/ha or more, 3300 g ai/ha
  • Sintofen Compositions and methods of the present disclosure can include sintofen or an agriculturally acceptable salt or ester thereof.
  • Sintofen shown below, is a carboxylic acid used for sterilizing spring and winter wheat for use in hybridization, at 800 g/ha.
  • Sintofen, as well as methods of preparing sintofen, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Thidiazuron Compositions and methods of the present disclosure can include thidiazuron or an agriculturally acceptable salt or ester thereof.
  • Thidiazuron shown below, is a carboxylic acid used for defoliation of cotton, at 210 g/ha.
  • Thidiazuron as well as methods of preparing thidiazuron, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. Thidiazuron can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • thidiazuron is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175
  • Triacontanol Compositions and methods of the present disclosure can include triacontanol or an agriculturally acceptable salt or ester thereof.
  • Triacontanol shown below, is a fatty alcohol used to increase the yields in cotton, potato, chilis, tomatoes, rice, grains and peanuts, and to increase the dry matter content, plant height, root spread and uniform, early maturity in crops.
  • Triacontanol, as well as methods of preparing triacontanol are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Trinexapac Compositions and methods of the present disclosure can include trinexapac or an agriculturally acceptable salt or ester thereof.
  • Trinexapac shown below, is a cyclohexanedione used to: prevent lodging in cereals and winter oilseed rape, at 100–300 g/ha; retard growth in turf, at 150–500 g/ha; and promote maturation in sugar cane, at 100–250 g/ha.
  • Trinexapac as well as methods of preparing trinexapac, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016. Trinexapac can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • trinexapac is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g
  • Uniconazole Compositions and methods of the present disclosure can include uniconazole or an agriculturally acceptable salt or ester thereof.
  • Uniconazole shown below, is a triazole used to: reduce lodging in rice; reduce vegetative growth and increase flowering in ornamentals, at a spray concentration of 0.5-50 ppm; and reduce vegetative growth in trees.
  • Uniconazole-P is an optically active form of uniconazole.
  • Uniconazole, as well as methods of preparing uniconazole, are known in the art. Its plant growth regulation activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • compositions comprising compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof) may be mixed with or applied in combination with (b) a plant growth regulator (PGR), an agriculturally acceptable salt or ester thereof, or mixtures thereof.
  • PGR plant growth regulator
  • (a) and (b) are used in an amount sufficient to induce an enhanced herbicidal effect (e.g., increased damage or injury to undesirable vegetation) while still showing good crop compatibility (e.g., no increased damage to crops or minimal increased damage or injury to crops) when compared to the individual application of the herbicidal compounds (a) or (b).
  • the damage or injury to undesirable vegetation caused by the compositions and methods disclosed herein is evaluated using a scale from 0% to 100%, when compared with the untreated control vegetation, wherein 0% indicates no damage to the undesirable vegetation and 100% indicates complete destruction of the undesirable vegetation.
  • the joint action of (a) the compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) the PGR, an agriculturally acceptable salt or ester thereof, or mixtures thereof results in enhanced herbicidal effect against undesirable vegetation, even at application rates below those typically used for the herbicide to have a herbicidal effect on its own.
  • the compositions and methods disclosed herein can, based on the individual components, be used at lower application rates to achieve a herbicidal effect comparable to the effect produced by the individual components at normal application rates.
  • the weight ratio of (a) the compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof) (in g ae/ha) to (b) the PGR, an agriculturally acceptable salt or ester thereof, or mixtures thereof (in g ai/ha) is 1:7500 or more, such as 1:7000 or more, 1:6000 or more, 1:5000 or more, 1:4000 or more, 1:3000 or more, 1:2500 or more, 1:2000 or more, 1:1500 or more, 1:1000 or more, 1: 900 or more, 1: 800 or more, 1:700 or more, 1:600 or more, 1:500 or more, 1:400 or more, 1:300 or more, 1:250 or more, 1:200 or more, 1:150 or more, 1:100 or more,
  • the active ingredients in the compositions disclosed herein consist of compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), and (b) a PGR, an agriculturally acceptable salt or ester thereof, or mixtures thereof.
  • the composition may include other components, such as safeners or adjuvants, but does not include a herbicidal active ingredient in addition to (a) and (b).
  • the compositions may exclude one or more herbicidal active ingredients specified above.
  • the compositions may include one or more herbicidal active ingredients in addition to (a) and (b), but may exclude one or more herbicidal ingredients specified above.
  • compositions include an acetyl CoA carboxylase (ACCase) inhibitor herbicide or an agriculturally acceptable salt or ester thereof.
  • ACCase inhibitor herbicides inhibit lipid biosynthesis in the plant. Examples of ACCase inhibitor herbicides include aryloxyphenoxypropionates, cyclohexanediones, and phenylpyrazolines.
  • the ACCase inhibitor herbicide can include an aryloxyphenoxypropionate herbicide. In some aspects, the ACCase inhibitor herbicide can include a cyclohexanedione herbicide. In some aspects, the ACCase inhibitor herbicide can include a phenylpyrazoline herbicide. In some aspects, the composition can include an ACCase inhibitor selected from the group of cyclohexanediones, aryloxyphenoxypropionates, phenylpyrazolines, or combinations thereof.
  • the composition can include clodinafop, cyhalofop, diclofop, fenoxaprop, fenthiaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, agriculturally acceptable salts or esters thereof, or combinations thereof.
  • the composition can include, alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim, agriculturally acceptable salts or esters thereof, or combinations thereof.
  • the composition can include pinoxaden.
  • the composition can include an ACCase inhibitor herbicide selected from the group consisting of alloxydim, butroxydim, clethodim, clodinafop, cloproxydim, cycloxydim, cyhalofop, diclofop, fenoxaprop, fenthiaprop, fluazifop, haloxyfop, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim, tralkoxydim, agriculturally acceptable salts and esters thereof, and combinations thereof.
  • an ACCase inhibitor herbicide selected from the group consisting of alloxydim, butroxydim, clethodim, clodinafop, cloproxydim, cycloxydim, cyhalofop, diclofop, fenoxaprop, fenthiaprop, flua
  • the ACCase inhibitor herbicide or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the ACCase inhibitor herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2 g ai/ha or more, such as 2.5 g ai/ha or more, 3 g ai/ha or more, 3.5 g ai/ha or more, 4 g ai/ha or more, 4.5 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 15 g ai/ha or more
  • the composition contains: compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof); and (b) alloxydim, butroxydim, clethodim, clodinafop, cloproxydim, cycloxydim, cyhalofop, diclofop, fenoxaprop, fenthiaprop, fluazifop, haloxyfop, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, sethoxydim, tepraloxydim, tralkoxydim, agriculturally acceptable salts and esters thereof, and combinations thereof.
  • Alloxydim Compositions and methods of the present disclosure can include alloxydim or an agriculturally acceptable salt or ester thereof.
  • Alloxydim shown below, is a cyclohexanedione herbicide that provides post-emergence control of grass weeds and volunteer cereals in sugar beet, vegetables and broad-leaved crops. Alloxydim, as well as methods of preparing alloxydim, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Alloxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • alloxydim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 299 g ai/ha or more, such as 300 g ai/ha or more, 320 g ai/ha or more, 340 g ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, 400 g ai/ha or more, 420 g ai/ha or more, 440 g ai/ha or more, 460 g ai/ha or more, 480 g ai/ha or more, 500 g ai/ha or more, 520 g ai/ha or more, 540 g ai/ha or more, 560 g ai/ha or more, 580 g ai/ha or more, 600 g ai/ha or more, 620 g ai/ha or more, 640 g ai/
  • Butroxydim Compositions and methods of the present disclosure can include butroxydim or an agriculturally acceptable salt or ester thereof.
  • Butroxydim shown below, is a cyclohexanedione herbicide that provides post-emergence control of annual grasses in many broad-leaved crops.
  • Butroxydim, as well as methods of preparing butroxydim are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Butroxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • butroxydim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 9 g ai/ha or more, such as10 g ai/ha or more, 15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or
  • Clethodim Compositions and methods of the present disclosure can include clethodim or an agriculturally acceptable salt or ester thereof.
  • Clethodim shown below, is a cyclohexanedione herbicide that provides post-emergence control of annual and perennial grasses in a wide range of broad-leaved crops, including such field crops as canola/oilseed rape, soybean, cotton, flax, sunflowers, alfalfa, peanuts, sugar beet, tobacco, and potatoes, as well as vegetable crops, trees, and vines.
  • Clethodim, as well as methods of preparing clethodim are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Clethodim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • clethodim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2 g ai/ha or more, such as 3 g ai/ha or more, 4 g ai/ha or more, 6 g ai/ha or more, 8 g ai/ha or more, 10 g ai/ha or more, 12 g ai/ha or more, 14 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g ai/ha or more, 30 g
  • Clodinafop Compositions and methods of the present disclosure can include clodinafop or an agriculturally acceptable salt or ester thereof.
  • Clodinafop-propargyl shown below, is prop-2- ynyl (R)-2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionate and is used for post- emergence control of annual grasses, including Avena, Lolium, Setaria, Phalaris, and Alopecurus spp., in cereals. .
  • Clodinafop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • clodinafop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 10 g ai/ha or more, such as 11 g ai/ha or more, 12 g ai/ha or more, 13 g ai/ha or more, 14 g ai/ha or more,15 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/
  • Cloproxydim Compositions and methods of the present disclosure can include cloproxydim or an agriculturally acceptable salt or ester thereof.
  • Cloproxydim shown below, is a cyclohexanedione herbicide that has been evaluated by the Chevron Chemical Company. Cloproxydim provides post-emergence control of a wide range of annual and perennial grasses in beans, cotton, potatoes, sugar beets, and most vegetable crops. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Cycloxydim Compositions and methods of the present disclosure can include cycloxydim or an agriculturally acceptable salt or ester thereof.
  • Cycloxydim shown below, is a cyclohexanedione herbicide that provides post-emergence control of annual and perennial grasses (except red fescue and Poa spp.) in canola/oilseed rape, beans, potatoes, brassicas, cotton, celery, fennel, beetroot, sugar beets, fodder beets, sunflowers, soybeans, flax, alfalfa, crucifers, and alliums. Cycloxydim, as well as methods of preparing cycloxydim, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Cycloxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • cycloxydim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190
  • Cyhalofop Compositions and methods of the present disclosure can include cyhalofop or an agriculturally acceptable salt or ester thereof.
  • Cyhalofop as well as methods of preparing cyhalofop, are known in the art.
  • Cyhalofop is an aryloxyphenoxypropionate ester that is used for post-emergence control of grass weeds in rice.
  • Cyhalofop-butyl shown below, is an ester of cyhalofop.
  • Cyhalofop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • cyhalofop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 20 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 120 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 180 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, 275
  • Diclofop Compositions and methods of the present disclosure can include diclofop or an agriculturally acceptable salt or ester thereof.
  • Diclofop-methyl shown below, is an aryloxyphenoxypropionate that is used for post-emergence control of wild oats, wild millets, and other annual grass weeds in wheat, barley, rye, red fescue, and broad-leaved crops such as soybeans, sugar beets, fodder beets, flax, legumes, canola/oilseed rape, sunflowers, clover, alfalfa, peanuts, brassicas, carrots, celery, parsnips, lettuce, spinach, potatoes, cucumbers, peas, beans, tomatoes, fennel, alliums, and herbs.
  • Diclofop as well as methods of preparing diclofop, are known in the art. Diclofop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • diclofop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount 100 g ai/ha or more, such as 150 g ai/ha or more, 175 g ai/ha or more, 200 g ai/ha or more, 220 g ai/ha or more, 240 g ai/ha or more, 260 g ai/ha or more, 280 g ai/ha or more, 300 g ai/ha or more, 320 g ai/ha or more, 340 g ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, 400 g ai/ha or more, 420 g ai/ha or more, 440 g ai/ha or more, 460 g ai/ha or more, 480 g ai/ha or more, 500 g ai/ha or
  • Fenoxaprop Compositions and methods of the present disclosure can include fenoxaprop or an agriculturally acceptable salt or ester thereof.
  • Fenoxaprop is an aryloxyphenoxypropionate that is used for post-emergence control of annual and perennial grass weeds in potatoes, beans, soybeans, beets, vegetables, peanuts, and cotton; and (when applied with the herbicide safener fenchlorazole-ethyl) annual and perennial grass weeds and wild oats in wheat, rye, and triticale.
  • Fenoxaprop-P-ethyl shown below, is an ester of fenoxaprop.
  • Fenoxaprop, as well as methods of preparing fenoxaprop are known in the art.
  • Fenoxaprop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • fenoxaprop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 25 g ai/ha or more, such as 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g a
  • Fenthiaprop Compositions and methods of the present disclosure can include fenthiaprop or an agriculturally acceptable salt or ester thereof.
  • Fenthiaprop shown below, is an aryloxyphenoxypropionate herbicide that is used for post-emergence control of many annual and perennial grasses and volunteer cereals in canola/oilseed rape, potatoes, and sugar beets.
  • Fenthiaprop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • fenthiaprop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount 150 g ai/ha or more, such as 160 g ai/ha or more,170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 220 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 280 g ai/ha or more, 300 g ai/ha or more, 320 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 380 g ai/ha or more, 400 g ai/ha or more, 420 g ai/ha or more
  • Fluazifop Compositions and methods of the present disclosure can include fluazifop or an agriculturally acceptable salt or ester thereof.
  • Fluazifop is an aryloxyphenoxypropionate that is used for post-emergence control of annual and perennial grass weeds in broad-leaved crops, including control of volunteer cereals and other grass weeds in canola/oilseed rape, sugar beet, fodder beet, potatoes, cotton, soybeans, peanuts, pome fruit, bush fruit, vines, citrus fruit, pineapples, bananas, strawberries, sunflowers, alfalfa, coffee, ornamentals and many vegetables.
  • Fluazifop-P-butyl shown below, is an ester of fluazifop.
  • Fluazifop as well as methods of preparing fluazifop, are known in the art. Fluazifop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • fluazifop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 grams active ingredient per hectare (g ai/ha) or more, such as 105 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more, 275 g ai/ha or more, 300 g ai/ha or more, 325 g ai/ha or more, 350 g ai/ha or more, 375
  • Haloxyfop Compositions and methods of the present disclosure can include haloxyfop or an agriculturally acceptable salt or ester thereof.
  • Haloxyfop is an aryloxyphenoxypropionate that is used post-emergence for control of annual and perennial grasses in sugar beets, fodder beets, canola/oilseed rape, potatoes, leafy vegetables, onions, flax, sunflowers, soybeans, vines, strawberries and other crops.
  • Haloxyfop-P-methyl shown below, is an ester of haloxyfop; haloxyfop-R-methyl is the racemic form of this herbicide.
  • Haloxyfop, as well as methods of preparing haloxyfop are known in the art.
  • Haloxyfop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • haloxyfop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 24 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g a
  • Metamifop Compositions and methods of the present disclosure can include metamifop.
  • Metamifop shown below, is an aryloxyphenoxypropionate that is used for post-emergence control of annual and perennial grass weeds (including Echinochloa spp., Leptochloa chinensis, Digitaria spp. and Eleusine indica) in rice, wheat, soybeans, cotton, and turf grass.
  • Metamifop as well as methods of preparing metamifop, are known in the art. Metamifop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • metamifop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 105 g ai/ha or more, 110 g ai/ha or more, 115 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 135 g ai/ha or more, 140 g ai/ha or more, 145
  • Pinoxaden Compositions and methods of the present disclosure can include pinoxaden or an agriculturally acceptable salt or ester thereof.
  • Pinoxaden shown below, is a phenylpyrazoline herbicide that provides post-emergence control of grass weeds in wheat, barley, lawns, and turf.
  • Pinoxaden, as well as methods of preparing pinoxaden are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Pinoxaden can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pinoxaden is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2 g ai/ha or more, such as 2.5 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 8 g ai/ha or more, 10 g ai/ha or more, 12 g ai/ha or more, 14 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more
  • Profoxydim Compositions and methods of the present disclosure can include profoxydim or an agriculturally acceptable salt or ester thereof.
  • Profoxydim shown below, is a cyclohexanedione herbicide.
  • Profoxydim is used for control of grass weeds, including Echinochloa spp., Brachiaria spp., Digitaria spp., Eleusine spp., Leptochloa spp., Setaria spp., Ischaemum rugosum and Rottboellia exaltata, in rice.
  • Profoxydim, as well as methods of preparing profoxydim are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Profoxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • profoxydim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 105 g ai/ha or more, 110 g ai/ha or more, 115 g ai/ha or more, 120 g ai/ha or more, 125 g g
  • Propaquizafop Compositions and methods of the present disclosure can include propaquizafop.
  • Propaquizafop shown below, is an aryloxyphenoxypropionate that is to control a wide range of annual and perennial grasses in soybeans, cotton, sugar beets, potatoes, peanuts, peas, canola/oilseed rape and vegetables.
  • Propaquizafop, as well as methods of preparing propaquizafop are known in the art.
  • Propaquizafop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • propaquizafop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 29 g ai/ha or more, such as 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/
  • Quizalofop Compositions and methods of the present disclosure can include quizalofop or an agriculturally acceptable salt or ester thereof.
  • Quizalofop is an aryloxyphenoxypropionate that is used for selective post-emergence control of annual and perennial grass weeds in potatoes, soybeans, sugar beets, peanuts, canola/oilseed rape, sunflowers, vegetables, cotton and flax.
  • Quizalofop-P-ethyl shown below, is an ester of quizalofop.
  • Quizalofop, as well as methods of preparing quizalofop, are known in the art.
  • Quizalofop can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • quizalofop is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 24 g ai/ha or more, such as 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g a
  • Sethoxydim Compositions and methods of the present disclosure can include sethoxydim or an agriculturally acceptable salt or ester thereof.
  • Sethoxydim shown below, is a cyclohexanedione herbicide that is used for controlling annual and perennial grasses in broad- leaved crops, including canola/oilseed rape, soybean, cotton, fodder beets, sunflowers, spinach, potatoes, tobacco, peanuts, strawberries, alfalfa, flax, vegetables, and sugar beet.
  • Sethoxydim, as well as methods of preparing sethoxydim are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Sethoxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • sethoxydim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2 g ai/ha or more, such as 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 8 g ai/ha or more, 10 g ai/ha or more, 12 g ai/ha or more, 14 g ai/ha or more, 16 g ai/ha or more, 18 g ai/ha or more, 20 g ai/ha or more, 22 g ai/ha or more, 24 g ai/ha or more, 26 g ai/ha or more, 28 g a
  • Tepraloxydim Compositions and methods of the present disclosure can include tepraloxydim or an agriculturally acceptable salt or ester thereof.
  • Tepraloxydim shown below, is a cyclohexanedione herbicide that is used for broad-spectrum post-emergence grass weed control, especially Poa annua and volunteer maize, and also Sorghum halepense and Elymus repens, in broad-leaved crops.
  • Tepraloxydim, as well as methods of preparing tepraloxydim are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016.
  • Tepraloxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • tepraloxydim is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 25 g ai/ha or more, such as 27.5 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more,
  • Tralkoxydim Compositions and methods of the present disclosure can include tralkoxydim or an agriculturally acceptable salt or ester thereof.
  • Tralkoxydim is a cyclohexanedione herbicide that has the chemical name 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-mesitylcyclohex-2-enone, and has the following structure: Tralkoxydim is used for post-emergence control of annual grass weeds (including Avena spp., Lolium spp., Setaria viridis, Phalaria spp., Alopecurus myosuroides, and Apera spica-venti) in wheat and barley.
  • Tralkoxydim as well as methods of preparing tralkoxydim, are known in the art. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Tralkoxydim can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 95 g ai/ha or more, such as 100 g ai/ha or more, 105 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 225 g ai/ha or more, 250 g ai/ha or more,
  • VLCFA SYNTHESIS INHIBITOR HERBICIDES In addition to the compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof), the compositions include a very long chain fatty acid (VLCFA) synthesis inhibitor herbicide.
  • VLCFA very long chain fatty acid
  • Very long chain fatty acids have multiple functions in the plant, primarily serving as precursors of cuticle wax biosynthesis, and as components of storage lipids, sphingolipids and phospholipids.
  • VLCFA synthesis inhibitors include, but are not limited to, acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fentrazamide, flufenacet, ipfencarbazone, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, and thenylchlor.
  • the composition can include a VLCFA synthesis inhibitor herbicide selected from the group consisting of acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fentrazamide, flufenacet, ipfencarbazone, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, thenylchlor, agriculturally acceptable salts and esters thereof, and combinations thereof.
  • a VLCFA synthesis inhibitor herbicide selected from the group consisting of acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fentrazamide, flufenacet, ipfencarbazone, mefenacet,
  • the VLCFA synthesis inhibitor herbicide or agriculturally acceptable salt or ester thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the VLCFA synthesis inhibitor herbicide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 40 gram active ingredient per hectare (g ai/ha) or more, such as 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g a
  • the composition contains: compounds according to Formula I or the compounds PYR-1 through PYR-21 (and all stereoisomers thereof); and (b) acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethenamid, diphenamid, fentrazamide, flufenacet, ipfencarbazone, mefenacet, metazachlor, metolachlor, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone, thenylchlor, or combinations thereof.
  • the VLCFA synthesis inhibitor herbicide can comprise acetochlor or an agriculturally acceptable salt or ester thereof.
  • Acetochlor shown below, is 2-chloro-N- (ethoxymethyl)-N-(2-ethyl-6-methylphenyl)acetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of acetochlor include its use pre-emergence or pre-plant to control annual grasses, certain annual broadleaf weeds and yellow nutsedge (Cyperus esculentus) in maize, peanuts, soybeans, cotton, potatoes and sugarcane.
  • Acetochlor can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • acetochlor is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2500 g ai/ha or more, such as 2600 g ai/ha or more, 2700 g ai/ha or more, 2750 g ai/ha or more, 2800 g ai/ha or more, 2900 g ai/ha or more, 3000 g ai/ha or more, 3100 g ai/ha or more, 3200 g ai/ha or more, 3250 g ai/ha or more, 3300 g ai/ha or more, 3400 g ai/ha or more, 3500 g ai/ha or more, 3600 g ai/ha or more, 3700
  • the VLCFA synthesis inhibitor herbicide can comprise alachlor or an agriculturally acceptable salt or ester thereof.
  • Alachlor show below, is 2-chloro-N-(2,6- diethylphenyl)-N-(methoxymethyl) acetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of alachlor include its use for pre-emergence control of annual grasses and many broadleaf weeds in cotton, brassicas, maize, oilseed rape, peanuts, radish, soybeans and sugar cane.
  • Alachlor can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • alachlor is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1500 g ai/ha or more, such as 1550 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1800 g ai/ha or more, 1900 g ai/ha or more, 2000 g ai/ha or more, 2050 g ai/ha or more, 2100 g ai/ha or more, 2150 g ai/ha or more, 2200 g ai/ha or more, 2240 g ai/ha or more, 2250 g ai/ha or more, 2300 g ai/ha or more, 2350 g ai/ha or more
  • the VLCFA synthesis inhibitor herbicide can comprise anilofos or an agriculturally acceptable salt or ester thereof.
  • Anilofos shown below, is S-[2-[(4- chlorophenyl)(1-methylethyl)amino]-2-oxoethyl] O,O-dimethyl phosphorodithioate. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of anilofos include its use for control of annual grassy weeds and sedges in transplanted rice.
  • Anilofos can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • anilofos is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 250 g ai/ha or more, such as 260 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/ha or more, 325 g ai/ha or more, 350 g ai/ha or more, 375 g ai/ha or more, 400 g ai/ha or more, 425 g ai/ha or more, 450 g ai/ha or more, 475 g ai/ha or more, 500 g ai/ha or more, 525 g ai/ha or more, 550 g ai
  • the VLCFA synthesis inhibitor herbicide can comprise butachlor or an agriculturally acceptable salt or ester thereof.
  • Butachlor shown below, is N- (butoxymethyl)-2-chloro-N-(2,6-diethylphenyl) acetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of butachlor include its use for pre-emergence control of annual grasses and certain broadleaf weeds in seeded and transplanted rice, barley, sugar beets, wheat, and brassicas.
  • Butachlor thereof can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • butachlor is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 400 g ai/ha or more, such as 450 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more
  • the VLCFA synthesis inhibitor herbicide can comprise cafenstrole or an agriculturally acceptable salt or ester thereof.
  • cafenstrole shown below, is N,N-diethyl- 3-[(2,4,6-trimethylphenyl)sulfonyl]-1H-1,2,4-triazole-1-carboxamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of cafenstrole include its use for pre- and post-emergence control of Echinochloa oryzicola, Cyperus difformis and other weeds in paddy rice.
  • cafenstrole can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • cafenstrole is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 60 g ai/ha or more, 75 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 220 g
  • the VLCFA synthesis inhibitor herbicide can comprise dimethachlor or an agriculturally acceptable salt or ester thereof.
  • Dimethachlor shown below, is 2-chloro-N-(2,6-dimethylphenyl)-N-(2-methoxyethyl)acetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of dimethachlor include its use for pre-emergence control of most annual grass (Alopecurus myosuroides, Apera spica-venti and Poa annua) and broadleaf weeds in oilseed rape.
  • Dimethachlor can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • dimethachlor is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1250 g ai/ha or more, such as 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1800 g ai/ha or more, 1900 g ai/ha or more, or 1950 g ai/ha or more; in an amount of 2000 g ai/ha or less, such as 1950 g ai/ha or less, 1900 g ai/ha or less, 1800 g
  • the VLCFA synthesis inhibitor herbicide can comprise dimethenamid or an agriculturally acceptable salt or ester thereof.
  • Dimethenamid shown below, is (RS)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1-methylethyl) acetamide.
  • Herbicidal activity for dimethenamid is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of dimethenamid include its use for pre- or early post- emergence control of annual grass and broadleaf weeds in maize, soybeans, sugar beet, potatoes, dry beans and other crops.
  • Dimethenamid-P (S)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-1- methyl-ethyl)acetamide, is a herbicidally active enantiomer of dimethenamid. Dimethenamid can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • dimethenamid is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 400 g ai/ha or more, such as 450 g ai/ha or more, 500 g ai/ha or more, 550 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g
  • the VLCFA synthesis inhibitor herbicide can comprise diphenamid or an agriculturally acceptable salt or ester thereof.
  • Diphenamid shown below, is N,N- dimethyl- ⁇ -phenylbenzeneacetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of diphenamid include its use for pre- emergence control of annual grasses and broadleaf weeds in a wide range of crops, including cotton, potatoes, sweet potatoes, tomatoes, vegetables, capsicums, okra, soybeans, peanuts, tobacco, orchard fruit, bush fruit, strawberries, forestry nurseries, and ornamental plants, shrubs and trees.
  • Diphenamid can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • diphenamid is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 3500 g ai/ha or more, such as 3600 g ai/ha or more, 3700 g ai/ha or more, 3750 g ai/ha or more, 3800 g ai/ha or more, 3900 g ai/ha or more, 3950 g ai/ha or more, 4000 g ai/ha or more, 4100 g ai/ha or more, 4200 g ai/ha or more, 4250 g ai/ha or more, 4300 g ai/ha or more, 4400 g ai/ha or more, 4500 g ai/ha or more, 4600 g
  • the VLCFA synthesis inhibitor herbicide can comprise fenoxasulfone or an agriculturally acceptable salt or ester thereof.
  • Fenoxasulfone shown below, is 2,5-dichloro-4-ethoxybenzyl-4,5-dihydro-5,5-dimethyl-1,2-oxazol-3-yl sulfone. Its herbicidal use is reported in the online version of The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of fenoxasulfone include control of grass and broadleaf weeds in rice.
  • Fentrazamide In some aspects, the VLCFA synthesis inhibitor herbicide can comprise fentrazamide or an agriculturally acceptable salt or ester thereof.
  • Fentrazamide shown below, is 4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo-1H-tetrazole-1-carboxamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of fentrazamide include its use for pre-and early post-emergence control of barnyard grass (Echinochloa spp.) and annual sedges in rice. Flufenacet In some aspects, the VLCFA synthesis inhibitor herbicide can comprise flufenacet or an agriculturally acceptable salt or ester thereof.
  • Flufenacet shown below, is N-(4- fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of flufenacet include its use for control of grass and broadleaf weeds in maize, wheat, rice, soybeans, tomatoes, potatoes, and sunflowers. Flufenacet can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • flufenacet is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 40 g ai/ha or more, such as 45 g ai/ha or more, 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 120 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more,160 g ai/ha or more, 180 g ai/ha or more, 200 g ai/ha or more, 220 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 280 g ai/ha or more, 290
  • the VLCFA synthesis inhibitor herbicide can comprise indanofan or an agriculturally acceptable salt or ester thereof.
  • Indanofan shown below, is (RS)-2-[2-(3- chlorophenyl)-2,3-epoxypropyl]-2-ethylindan-1,3-dione. Its herbicidal activity is exemplified in the online edition of The Pesticide Manual. Exemplary uses of indanofan include pre- and post-emergence control of Echinochloa crus-galli, Monochoria vaginalis, Lindernia procumbens, Cyperus difformis, Scirpus juncoides, and Eleocharis acicularis in transplanted rice.
  • the VLCFA synthesis inhibitor herbicide can comprise ipfencarbazone or an agriculturally acceptable salt or ester thereof.
  • Ipfencarbazone shown below, is 1-(2,4-dichlorophenyl)-N-(2,4-difluorophenyl)-1,5-dihydro-N-(1-methylethyl)-5- oxo-4H-1,2,4-triazole-4-carboxamide. Its herbicidal activity is exemplified in the online edition of The Pesticide Manual. Exemplary uses of ipfencarbazone include its use for pre- or early post-emergence control of grass, sedge, and some broadleaf weeds in rice.
  • Ipfencarbazone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • ipfencarbazone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 150 g ai/ha or more, such as 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g a
  • the VLCFA synthesis inhibitor herbicide can comprise mefenacet or an agriculturally acceptable salt or ester thereof.
  • Mefenacet shown below, is 2-(2- benzothiazolyloxy)-N-methyl-N-phenylacetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of mefenacet include its use for pre-emergence and early post-emergence control of grass weeds in transplanted rice. Mefenacet can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • mefenacet is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 40 g ai/ha or more, such as 50 g ai/ha or more, 60 g ai/ha or more, 70 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 250 g ai/ha or more, 300 g ai/ha or more, 350 g ai/
  • the VLCFA synthesis inhibitor herbicide can comprise metazachlor or an agriculturally acceptable salt or ester thereof.
  • Metazachlor shown below, is 2-chloro-N-(2,6-dimethylphenyl)-N-(1H-pyrazol-1-ylmethyl)acetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of metazachlor include its use for pre- and early post-emergence control of winter and annual grasses and broadleaf weeds in a variety of vegetable, fruit, grain, and orchard crops.
  • Metazachlor can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • metazachlor is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 750 g ai/ha or more, such as 775 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g a
  • the VLCFA synthesis inhibitor herbicide can comprise metolachlor or an agriculturally acceptable salt or ester thereof.
  • Metolachlor shown below, is 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016.
  • metolachlor examples include its use for control of annual grasses and broadleaf weeds in maize, sorghum, cotton, sugar beet, fodder beet, sugarcane, potatoes, peanuts, soybeans, safflowers, sunflowers, various vegetables, fruit and nut trees, and woody ornamentals.
  • S-metolachlor is a mixture of isomers, containing of 80-200% (S) to 20-0% (R) isomers of metolachlor.
  • Metolachlor can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • metolachlor is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 500 g ai/ha or more, such as 550 g ai/ha or more, 600 g ai/ha or more, 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g
  • the VLCFA synthesis inhibitor herbicide can comprise naproanilide or an agriculturally acceptable salt or ester thereof.
  • Naproanilide shown below, is 2-(2-naphthalenyloxy)-N-phenyl propanamide. Its herbicidal activity is exemplified in the online edition of The Pesticide Manual. Exemplary uses of naproanilide include its use for control of annual and some perennial weeds, but not Echinochloa crus-galli, in paddy rice, as well as good control of young Sagittaria pygmaea.
  • Naproanilide can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • naproanilide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2000 g ai/ha or more, such as 2050 g ai/ha or more, 2100 g ai/ha or more, 2150 g ai/ha or more, 2200 g ai/ha or more, 2240 g ai/ha or more, 2250 g ai/ha or more, 2300 g ai/ha or more, 2350 g ai/ha or more, 2400 g ai/ha or more, 2450 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2700 g ai/ha or more, 2
  • the VLCFA synthesis inhibitor herbicide can comprise napropamide or an agriculturally acceptable salt or ester thereof.
  • Napropamide shown below, is (RS)-N,N-diethyl-2-(1-naphthyloxy) propionamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016.
  • napropamide examples include its use for pre-emergence control of annual grasses and broadleaf weeds in asparagus, rhubarb, cucurbits, brassicas, oilseed rape, tomatoes, capsicums, potatoes, peas, nuts, fruit trees and bushes (including citrus), vines, strawberries, sunflowers, safflowers, ornamentals, tobacco, olives, figs, mint, turf, and other crops.
  • Napropamide can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • napropamide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2000 g ai/ha or more, such as 2050 g ai/ha or more, 2100 g ai/ha or more, 2150 g ai/ha or more, 2200 g ai/ha or more, 2240 g ai/ha or more, 2250 g ai/ha or more, 2300 g ai/ha or more, 2350 g ai/ha or more, 2400 g ai/ha or more, 2450 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2700 g ai/ha or more, 2750 g ai/ha or more, 2800 g ai/ha or more, 2900 g ai/ha or more, 3000 g ai/ha or more, 3100
  • the VLCFA synthesis inhibitor herbicide can comprise pethoxamid or an agriculturally acceptable salt or ester thereof.
  • Pethoxamid is 2-chloro-N-(2-ethoxyethyl)- N-(2-methyl-1-phenyl-1-propen-1-yl)acetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of pethoxamid include its use for pre- and early post-emergence control of grass weeds and broadleaf weeds in maize, oilseed rape and soybeans.
  • Pethoxamid can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pethoxamid is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 600 g ai/ha or more, such as 650 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g
  • the VLCFA synthesis inhibitor herbicide can comprise piperophos or an agriculturally acceptable salt or ester thereof.
  • Piperophos shown below, is S-[2-(2- methyl-1-piperidinyl)-2-oxoethyl] O,O-dipropylphosphorodithioate. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of piperophos include its use as a selective herbicide active against annual grasses and sedges in direct seeded or transplanted rice. Piperophos can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • piperophos is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 300 g ai/ha or more, such as 310 g ai/ha or more, 320 g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 370 g ai/ha or more, 380 g ai/ha or more, 390 g ai/ha or more, 400 g ai/ha or more, 410 g ai/ha or more, 420 g ai/ha or more, 430 g ai/ha or more, 440 g ai/ha or more, 450 g ai/ha or more, 460 g ai/ha or more, 480 g ai/ha or more, 500 g ai/ha
  • the VLCFA synthesis inhibitor herbicide can comprise pretilachlor or an agriculturally acceptable salt or ester thereof.
  • Pretilachlor shown below, is 2-chloro-N- (2,6-diethylphenyl)-N-(2-propoxyethyl)acetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of pretilachlor include its use for control of annual grasses, broadleaf weeds and sedges in transplanted and seeded rice.
  • Pretilachlor can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pretilachlor is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 250 g ai/ha or more, such as 260 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/ha or more, 325 g ai/ha or more, 350 g ai/ha or more, 375 g ai/ha or more, 400 g ai/ha or more, 425 g ai/ha or more, 450 g ai/ha or more, 475 g ai/ha or more, 500 g ai/ha or more, 525 g ai/ha or more, 550 g ai/ha or more, 575 g ai/ha or more, 600 g ai/ha or more, 625 g ai/ha or more, 650 g a
  • the VLCFA synthesis inhibitor herbicide can comprise propachlor or an agriculturally acceptable salt or ester thereof.
  • Propachlor shown below, is 2-chloro-N- (1-methylethyl)-N-phenylacetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. It is used pre-emergence, pre-planting incorporated or early post-emergence control of annual grasses and some broadleaf weeds in beans, brassicas, cotton, sorghum, peanuts, leeks, maize, onions, peas, roses, ornamental trees and shrubs, soybeans and sugar cane.
  • Propachlor can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • propachlor is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 3250 g ai/ha or more, such as 3300 g ai/ha or more, 3360 g ai/ha or more, 3400 g ai/ha or more, 3500 g ai/ha or more, 3600 g ai/ha or more, 3700 g ai/ha or more, 3750 g ai/ha or more, 3800 g ai/ha or more, 3900 g ai/ha or more, 3950 g ai/ha or more, 4000 g ai/ha or more, 4100 g ai/ha or more, 4200 g ai/ha or more, 4250 g a
  • the VLCFA synthesis inhibitor herbicide can comprise propisochlor or an agriculturally acceptable salt or ester thereof.
  • Propisochlor shown below, is 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(isopropoxymethyl)acetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of propisochlor include its use in pre-plant or pre-emergence control of annual grass and some broadleaf weeds in maize, sunflowers, soybeans, potatoes, beans, sweet lupins, peas, and onions.
  • Propisochlor can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • propisochlor is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 900 g ai/ha or more, such as 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1550 g ai/ha or more, 1600 g ai
  • the VLCFA synthesis inhibitor herbicide can comprise pyroxasulfone or an agriculturally acceptable salt or ester thereof.
  • Pyroxasulfone shown below, is 3-[[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4- yl]methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016.
  • Pyroxasulfone provides pre- and early post-emergence control of annual grasses and some broadleaf weeds in maize, soybeans, wheat, triticale, barley, and other crops.
  • the pyroxasulfone can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the pyroxasulfone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 40 g ai/ha or more, such as 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 105 g ai/ha or more, 110 g ai/ha or more, 115 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or
  • the VLCFA synthesis inhibitor herbicide can comprise thenylchlor or an agriculturally acceptable salt or ester thereof.
  • ylchlor shown below, is 2-chloro-N- (2,6-dimethylphenyl)-N-[(3-methoxy-2-thienyl)methyl]acetamide. Its herbicidal activity is exemplified in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of thenylchlor include its use for pre-emergence control of annual grass and broadleaf weeds in paddy rice.
  • thenylchlor can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • thenylchlor is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 225 g ai/ha or more, such as 230 g ai/ha or more, 235 g ai/ha or more, 240 g ai/ha or more, 245 g ai/ha or more, 250 g ai/ha or more, 255 g ai/ha or more, 260 g ai/ha or more, 265 g ai/ha or more, 270 g ai/ha or more, 275 g ai/ha or more, 280 g ai/ha or more, 285 g ai/ha or more, 290 g ai/ha or more, 295
  • compositions can include a microtubule assembly inhibitor (MAI) herbicide, an agriculturally acceptable salt or ester thereof, or mixtures thereof.
  • MAI microtubule assembly inhibitor
  • MAI herbicides may inhibit plant cell division by binding to tubulin, the major protein needed to form the microtubules required in cell division.
  • MAI herbicides examples include benfluralin, butamifos, butralin, carbetamide, chlorpropham, chlorthal, dithiopyr, ethalfluralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, thiazopyr, trifluralin, and agriculturally acceptable salts or esters thereof.
  • MAI herbicides can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the MAI herbicide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 g ai/ha or more, such as 105 g ai/ha or more, 110 g ai/ha or more, 115 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 135 g ai/ha or more, 140 g ai/ha or more, 145 g ai/ha or more, 150 g ai/ha or more, 155 g ai/ha or more, 160 g ai/ha or more, 165 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more,
  • the MAI herbicide can comprise benfluralin or an agriculturally acceptable salt or ester thereof.
  • Benfluralin shown below, is a dinitroaniline herbicide used for pre-plant incorporated control of annual grass and some annual broad-leaved weeds in peanuts, lettuce, cucumbers, chicory, endive, field beans, French beans, lentils, alfalfa, clovers, trefoil, tobacco and established turf, at 1000–1500 g/ha.
  • Benfluralin, as well as methods of preparing benfluralin are known in the art. Its herbicidal activity is described, for example, in Tomlin, C. D. S., Ed.
  • Benfluralin can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • benfluralin is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 900 g ai/ha or more, such as 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1440 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1600 g ai/ha or more, or 1700 g ai/ha or more; in an amount of 1750 g ai/ha or less, such as 1700 g ai/ha or
  • the MAI herbicide can comprise butamifos or an agriculturally acceptable salt or ester thereof.
  • Butamifos shown below, is a phosphoroamidate herbicide used for pre-emergence control of annual grass weeds in beans, turf, rice, at 900–1000 g/ha, and in vegetables, at 1000–2000 g/ha.
  • Butamifos, as well as methods of preparing butamifos are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Butamifos can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • butamifos is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1000 g ai/ha or more, such as 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1800 g ai/ha or more, 1900 g ai/ha or more, or 1950 g ai/ha or more; in an amount of 2000 g ai/ha or less, such as 1950 g ai/ha or less,
  • the MAI herbicide can comprise butralin or an agriculturally acceptable salt or ester thereof.
  • Butralin shown below, is a dinitroaniline herbicide used for pre-emergence control of annual broad-leaved and grass weeds in cotton, soybeans, rice, barley, beans, alliums, vines, ornamentals, fruit and nut trees, at 1120–3400 g/ha; control of suckers in tobacco, at 125 mg/plant.
  • Butralin, as well as methods of preparing butralin are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Butralin can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • butralin is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1100 g ai/ha or more, such as 1120 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1800 g ai/ha or more, 1900 g ai/ha or more, 2000 g ai/ha or more
  • the MAI herbicide can comprise carbetamide or an agriculturally acceptable salt or ester thereof.
  • Carbetamide shown below, is a carbamate herbicide used for control of annual grass weeds, including volunteer cereals, and some broad-leaved weeds in clover, alfalfa, sainfoin, brassicas, field beans, peas, lentils, sugar beets, oilseed rape, chicory, endive, sunflowers, caraway, strawberries, vines and fruit, at 2000 g/ha.
  • Carbetamide, as well as methods of preparing carbetamide are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Carbetamide can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • carbetamide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 900 g ai/ha or more, such as 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/
  • the MAI herbicide can comprise chlorpropham or an agriculturally acceptable salt or ester thereof.
  • Chlorpropham shown below, is a carbamate herbicide used to inhibit sprouting in stored potatoes, at 8–64 g/t and control suckers in tobacco.
  • Chlorpropham is also used for pre-emergence control of annual grass and some broad-leaved weeds in onions, leeks, garlic, shallots, alfalfa, clover, sugar beets, spinach, lettuce, endive, chicory, herbs, peas, beans, carrots, celery, black salsify, fennel, soybeans, cotton, rice, safflowers, sunflowers, cranberries, cane berries, ornamentals, ornamental trees and shrubs, perennial grass seed crops, etc., at up to 240 g/ha. Chlorpropham, as well as methods of preparing chlorpropham, are known in the art. Its herbicide activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Chlorpropham can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • chlorpropham is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 15 g ai/ha or more, such as 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or
  • the MAI herbicide can comprise chlorthal or an agriculturally acceptable salt or ester thereof.
  • Chlorthal shown below, is a benzoic acid herbicide used for preemergence control of annual grass and some broad-leaved weeds in onions, garlic, leeks, tomatoes, lettuce, cucurbits, peppers, aubergines, brassicas, potatoes, sweet potatoes, horseradish, field beans, soybeans, cotton, strawberries, ornamentals, established turf and other crops.
  • One common ester of chlorthal is chlorthal-dimethyl. Chlorthal, as well as methods of preparing chlorthal, are known in the art. Its herbicide activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Chlorthal can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • chlorthal is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 5000 g ai/ha or more, such as 5250 g ai/ha or more, 5500 g ai/ha or more, 5750 g ai/ha or more, 6000 g ai/ha or more, 6250 g ai/ha or more, 6500 g ai/ha or more, 6750 g ai/ha or more, 7000 g ai/ha or more, 7250 g ai/ha or more, 7500 g ai/ha or more, 7750 g ai/ha or more, 8000 g ai/ha or more, 8250 g ai/ha or more, 8500 g ai/
  • the MAI herbicide can comprise dithiopyr or an agriculturally acceptable salt or ester thereof.
  • Dithiopyr shown below, is a pyridine herbicide used for pre- and early post-emergence control of annual grass, e.g. crabgrass, and broad-leaved weeds in turf, at 280–1100 g/ha.
  • Dithiopyr as well as methods of preparing dithiopyr, are known in the art. Its herbicide activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Dithiopyr can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • dithiopyr is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 200 g ai/ha or more, such as 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g ai/ha or more, 275 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/ha or more, 310 g ai/ha or more, 320 g ai/ha or more, 325 g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350 g
  • the MAI herbicide can comprise ethalfluralin or an agriculturally acceptable salt or ester thereof.
  • Ethalfluralin shown below, is a dinitroaniline herbicide used for pre-plant incorporated control of annual grass and broad-leaved weeds in cotton, soybeans, dry beans, lentils, maize, sorghum, safflowers and sunflowers, at 1000–1250 g/ha; and as post- plant surface application for control of annual grass and broad-leaved weeds in peanuts and cucurbits.
  • Ethalfluralin, as well as methods of preparing ethalfluralin are known in the art. Its herbicide activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Ethalfluralin can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • ethalfluralin is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 750 g ai/ha or more, such as 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, or 1450
  • the MAI herbicide can comprise oryzalin or an agriculturally acceptable salt or ester thereof.
  • Oryzalin shown below, is a dinitroaniline herbicide used for pre-emergence control of annual grass and broad-leaved weeds in cotton, at 720–960 g/ha, soybeans, at 960–2160 g/ha, rice, at 240–480 g/ha, tree fruit, nut trees, vines, ornamentals, berries, amenity turf and non-crop areas, at 1920–4500 g/ha.
  • Oryzalin, as well as methods of preparing oryzalin are known in the art. Its herbicide activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Oryzalin can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • oryzalin is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 200 g ai/ha or more, such as 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g ai/ha or more, 275 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/ha or more, 310 g ai/ha or more, 320 g 210
  • the MAI herbicide can comprise pendimethalin or an agriculturally acceptable salt or ester thereof.
  • Pendimethalin shown below, is a dinitroaniline herbicide used for pre-plant incorporated, pre- and early post-emergence control of annual grass and broad- leaved weeds in cereals, onions, leeks, garlic, fennel, maize, sorghum, rice, soybeans, peanuts, brassicas, carrots, celery, black salsify, peas, field beans, lupins, evening primroses, tulips, potatoes, cotton, hops, pome fruit, stone fruit, berries, strawberries, citrus, lettuce, aubergines, peppers, established turf and in transplanted tomatoes, sunflowers and tobacco, at 600–2400 g/ha; control of suckers in tobacco.
  • Pendimethalin as well as methods of preparing pendimethalin, are known in the art. Its herbicide activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Pendimethalin can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • pendimethalin is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 500 g ai/ha or more, such as 525 g ai/ha or more, 550 g ai/ha or more, 575 g ai/ha or more, 600 g ai/ha or more, 625 g ai/ha or more, 650 g ai/ha or more, 675 g ai/ha or more, 700 g ai/ha or more, 750 g ai/ha or more, 800 g ai/ha or more, 850 g ai/ha or more, 900 g ai/ha or more, 950 g ai/ha or more, 1000 g ai/ha or more, 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g
  • Prodiamine shown below, is a dinitroaniline herbicide used for pre- plant or pre-emergence control of annual grass and broad-leaved weeds in non-crop land, ornamentals, turf, conifer and hardwood seedlings, at 375–1600 g/ha.
  • Prodiamine, as well as methods of preparing prodiamine, are known in the art. Its herbicide activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Prodiamine can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • prodiamine is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 350 g ai/ha or more, such as 360 g ai/ha or more, 370 g ai/ha or more, 375 g ai/ha or more, 380 g ai/ha or more, 390 g ai/ha or more, 400 g ai/ha or more, 410 g ai/ha or more, 420 g ai/ha or more, 425 g ai/ha or more, 430 g ai/ha or more, 440 g ai/ha or more, 450 g ai/ha or more, 460 g ai/ha or more, 470 g ai
  • the MAI herbicide can comprise propham or an agriculturally acceptable salt or ester thereof.
  • Propham shown below, is a carbamate herbicide used for control of annual grass and some broad-leaved weeds in alfalfa, clover, sugar beets, spinach, lettuce, peas, beans, flax, safflowers, beetroot, fodder beets, lettuce, chard, lentils and perennial grass seed crops, at 2300–5000 g/ha, and as a sprouting inhibitor in potatoes.
  • Propham as well as methods of preparing propham, are known in the art. Its herbicide activity is described, for example, in The Pesticide Manual, Eighteenth Edition, 2016.
  • Propham can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • propham is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2000 g ai/ha or more, such as 2100 g ai/ha or more, 2200 g ai/ha or more, 2300 g ai/ha or more, 2400 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2700 g ai/ha or more, 2800 g ai/ha or more, 2900 g ai/ha or more, 3000 g ai/ha or more, 3100 g ai/ha or more, 3200 g ai/ha or more, 3250 g ai/ha or more, 3300 g ai/ha
  • the MAI herbicide can comprise propyzamide or an agriculturally acceptable salt or ester thereof.
  • Propyzamide shown below, is a benzamide herbicide used for pre- and early post-emergence control of annual and perennial grass and some broad-leaved weeds, in fruit, vines, lettuce, endive, chicory, brassicas, oilseed rape, legumes, alfalfa, clover, trefoil, sainfoin, artichokes, sugar beets, roses, ornamental trees and shrubs, warm season amenity grass, fallow land and forestry and Poa annua in Bermuda grass, zoysia grass and certain other turf species, at 560–2200 g/ha.
  • Propyzamide as well as methods of preparing propyzamide, are known in the art. Its herbicide activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Propyzamide can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • propyzamide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 250 g ai/ha or more, such as 260 g ai/ha or more, 270 g ai/ha or more, 275 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/ha or more, 310 g ai/ha or more, 320 g ai/ha or more, 325 g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 370 g ai/ha or more, 375 g ai/ha or more, 380 g ai/ha or more, 390 g ai/ha or more, 400 g
  • the MAI herbicide can comprise thiazopyr or an agriculturally acceptable salt or ester thereof.
  • Thiazopyr shown below, is a pyridine herbicide used for pre- emergence control of annual grass and some broad-leaved weeds in tree fruit, vines, citrus, sugar cane, pineapples, alfalfa and forestry, at 100–560 g/ha.
  • Thiazopyr as well as methods of preparing thiazopyr, are known in the art. Its herbicide activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Thiazopyr can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • thiazopyr is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 100 g ai/ha or more, such as 110 g ai/ha or more, 120 g ai/ha or more, 125 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or
  • the MAI herbicide can comprise trifluralin or an agriculturally acceptable salt or ester thereof.
  • Trifluralin shown below, is a dinitroaniline herbicide used for pre-plant incorporated or pre-emergence control of annual grass and broad-leaved weeds in brassicas, beans, peas, carrots, parsnips, lettuce, peppers, tomatoes, artichokes, onions, garlic, vines, strawberries, raspberries, citrus, oilseed rape, peanuts, soybeans, sunflowers, safflowers, ornamentals, including trees and shrubs, cotton, sugar beets, sugar cane, winter cereals, amenity grass and forestry, at 500–1000 g/ha.
  • Trifluralin as well as methods of preparing trifluralin, are known in the art. Its herbicide activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Trifluralin can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • trifluralin is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 400 g ai/ha or more, such as 410 g ai/ha or more, 420 g ai/ha or more, 425 g ai/ha or more, 430 g ai/ha or more, 440 g ai/ha or more, 450 g ai/ha or more, 460 g ai/ha or more, 470 g ai/ha or more, 475 g ai/ha or more, 480 g ai/ha or more, 490 g ai/ha or more, 500 g ai/ha or more, 525 g ai/ha or more, 550 g ai/ha or more, 575 g ai/ha or more, 600 g ai/ha or more, 625 g ai/ha or more, 650
  • compositions can include a fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide, an agriculturally acceptable salt or ester thereof, or mixtures thereof.
  • FA/LSI herbicides appear to interfere with the biosynthesis of fatty acids and lipids, thereby reducing the deposition of cuticle wax, and to cause abnormal cell development or to inhibit cell division in germinating seedlings.
  • FA/LSI herbicides include benfuresate, bensulide, butylate, cycloate, dalapon, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, prosulfocarb, thiobencarb, tiocarbazil, tri- allate, vernolate.
  • the composition can include a FA/LSI herbicide selected from the group consisting of benfuresate, bensulide, butylate, cycloate, dalapon, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, prosulfocarb, thiobencarb, tiocarbazil, tri- allate, vernolate, agriculturally acceptable salts or esters thereof, and mixtures thereof.
  • FA/LSI herbicides can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • the FA/LSI herbicide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 300 g ai/ha or more, such as 310 g ai/ha or more, 320 g ai/ha or more, 325 g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 370 g ai/ha or more, 375 g ai/ha or more, 380 g ai/ha or more, 390 g ai/ha or more, 400 g ai/ha or more, 410 g ai/ha or more, 420 g ai/ha or more, 425 g ai/ha or more, 430 g ai/ha or more, 440 g ai/ha or more,
  • the FA/LSI herbicide can comprise benfuresate or an agriculturally acceptable salt or ester thereof.
  • Benfuresate shown below, is a benzofuran herbicide used for post-emergence control of grass and broad-leaved weeds in paddy rice, fruit, beans, maize, sugar cane and perennial crops, at 450–600 g/ha and pre-plant incorporated in cotton and tobacco, at 2000–3000 g/ha.
  • Benfuresate, as well as methods of preparing benfuresate are known in the art. Its herbicidal activity is described, for example, in Tomlin, C. D. S., Ed.
  • Benfuresate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • benfuresate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 150 g ai/ha or more, such as 160 g ai/ha or more, 170 g ai/ha or more, 175 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g ai/ha or more, 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g ai/ha or more, 275 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/
  • the FA/LSI herbicide can comprise bensulide or an agriculturally acceptable salt or ester thereof.
  • Bensulide shown below, is a phosphorodithioate herbicide used for pre-emergence control of broad-leaved weeds in brassicas, cucurbits, lettuce, onions, etc., at 5600–6700 g/ha, and in established turf, at 8400–28000 g/ha per season. Bensulide, as well as methods of preparing bensulide, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Bensulide can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • bensulide is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 5000 g ai/ha or more, such as 5250 g ai/ha or more, 5500 g ai/ha or more, 5750 g ai/ha or more, 6000 g ai/ha or more, 6250 g ai/ha or more, 6500 g ai/ha or more, 6750 g ai/ha or more, 7000 g ai/ha or more, 7250 g ai/ha or more, 7500 g ai/ha or more, 7750 g ai/ha or more, 8000 g ai/ha or more, 8250 g ai/ha or more, 8500 g
  • the FA/LSI herbicide can comprise butylate or an agriculturally acceptable salt or ester thereof.
  • Butylate shown below, is a thiocarbamate herbicide used for pre-plant incorporated control of annual grass weeds and Cyperus spp. in maize and pineapples at 3000–4000 g/ha.
  • Butylate, as well as methods of preparing butylate, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016. Butylate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • butylate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 3000 g ai/ha or more, such as 3100 g ai/ha or more, 3200 g ai/ha or more, 3250 g ai/ha or more, 3300 g ai/ha or more, 3400 g ai/ha or more, 3500 g ai/ha or more, 3750 g ai/ha or more, 4000 g ai/ha or more, 4250 g ai/ha or more, 4500 g ai/ha or more, 4750 g ai/ha or more, 5000 g ai/ha or more, 5250 g ai/ha or more, 5500 g ai/ha or more, 5750 g ai/ha or more, 6000 g ai/ha or more, 6250 g ai/ha or more, 6
  • the FA/LSI herbicide can comprise cycloate or an agriculturally acceptable salt or ester thereof.
  • Cycloate shown below, is a thiocarbamate herbicide used for pre-plant incorporated control of annual and some perennial grass weeds, Cyperus spp., and some annual broad-leaved weeds in sugar beets, fodder beets, beetroot and spinach, at 3000– 4000 g/ha. Cycloate, as well as methods of preparing cycloate, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Cycloate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • cycloate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2500 g ai/ha or more, such as 2600 g ai/ha or more, 2700 g ai/ha or more, 2800 g ai/ha or more, 2900 g ai/ha or more, 3000 g ai/ha or more, 3100 g ai/ha or more, 3200 g ai/ha or more, 3250 g ai/ha or more, 3300 g ai/ha or more, 3400 g ai/ha or more, 3500 g ai/ha or more, 3750 g ai/ha or more, 4000 g ai/ha or more, or 4250 g
  • the FA/LSI herbicide can comprise dalapon or an agriculturally acceptable salt or ester thereof.
  • Dalapon shown below, is a thiocarbamate herbicide used for pre- and post-emergence control of annual and perennial grass weeds in non-crop land, e.g.
  • Common agriculturally acceptable salts of dalapon include the magnesium and sodium salts thereof. Dalapon, as well as methods of preparing dalapon, are known in the art.
  • dalapon is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1500 g ai/ha or more, such as 1600 g ai/ha or more, 1700 g ai/ha or more, 1750 g ai/ha or more, 1800 g ai/ha or more, 1900 g ai/ha or more, 2000 g ai/ha or more, 2100 g ai/ha or more, 2200 g ai/ha or more, 2300 g ai/ha or more, 2400 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2700 g ai/ha or more, 2800 g ai/ha or more, 2900 g ai/ha or more, 3000 g ai/ha or more, 3100 g ai/ha or more, 3200 g a
  • EPTC is a thiocarbamate herbicide used for pre-plant incorporated control of annual and perennial grass, especially couch grass, sedge, e.g. Cyperus spp. and some broad-leaved weeds in potatoes, beans, peas, forage legumes, beetroot, sugar beets, alfalfa, trefoil, clover, cotton, maize, flax, sweet potatoes, safflowers, sunflowers, strawberries, citrus, almonds, walnuts, ornamentals, pineapples and pine nurseries, at 4500–6700 g/ha, and in maize, with dichlormid safener.
  • EPTC as well as methods of preparing EPTC, are known in the art.
  • EPTC can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • EPTC is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1000 g ai/ha or more, such as 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1750 g ai/ha or more, 1800 g ai/ha or more, 1900 g ai/ha or more, 2000 g ai/ha or more, 2100 g ai/ha or more, 2200 g ai/ha or more
  • the FA/LSI herbicide can comprise esprocarb, or an agriculturally acceptable salt or ester thereof.
  • Esprocarb shown below, is a thiocarbamate herbicide used for pre- and post-emergence control of annual weeds, e.g. Echinochloa spp., in paddy rice, at 1500–4000 g/ha.
  • Esprocarb, as well as methods of preparing esprocarb are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Esprocarb can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • esprocarb is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 400 g ai/ha or more, such as 410 g ai/ha or more, 420 g ai/ha or more, 425 g ai/ha or more, 430 g ai/ha or more, 440 g ai/ha or more, 450 g ai/ha or more, 460 g ai/ha or more, 470 g ai/ha or more, 475 g ai/ha or more, 480 g ai/ha or more, 490 g ai/ha or more, 500 g ai/ha or more, 525 g ai/ha or more, 550 g
  • the FA/LSI herbicide can comprise ethofumesate, or an agriculturally acceptable salt or ester thereof.
  • Ethofumesate shown below, is a benzofuran herbicide used for pre- and post-emergence control of grass and broad-leaved weeds in sugar and other beets, turf, ryegrass and other pasture grasses, at 300–2000 g/ha.
  • Ethofumesate, as well as methods of preparing ethofumesate are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Ethofumesate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • ethofumesate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 200 g ai/ha or more, such as 210 g ai/ha or more, 220 g ai/ha or more, 225 g ai/ha or more, 230 g ai/ha or more, 240 g ai/ha or more, 250 g ai/ha or more, 260 g ai/ha or more, 270 g ai/ha or more, 275 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/ha or more, 310 g ai/ha or more,
  • the FA/LSI herbicide can comprise flupropanate, or an agriculturally acceptable salt or ester thereof.
  • Flupropanate shown below, is a halogenated alkanoic acid herbicide used for post-emergence control of annual and perennial grass weeds, e.g., serrated tussock and Chilean needle grass, in pastures and in uncultivated land.
  • One agriculturally acceptable salt of flupropanate is flupropanate-sodium. Flupropanate, as well as methods of preparing flupropanate, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Flupropanate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • flupropanate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1000 g ai/ha or more, such as 1050 g ai/ha or more, 1100 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1750 g ai/ha or more, 1800 g ai/
  • the FA/LSI herbicide can comprise molinate, or an agriculturally acceptable salt or ester thereof.
  • Molinate shown below, is a thiocarbamate herbicide used for control of germinating broad-leaved and grass weeds, particularly Echinochloa spp. and Glyceria spp., in rice, at 2500–5000 g/ha, applied either before planting to water-seeded or shallow soil-seeded rice or post-flood, post-emergence in other types of rice culture.
  • Molinate, as well as methods of preparing molinate are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Molinate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • molinate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 2500 g ai/ha or more, such as 2600 g ai/ha or more, 2700 g ai/ha or more, 2800 g ai/ha or more, 2900 g ai/ha or more, 3000 g ai/ha or more, 3100 g ai/ha or more, 3200 g ai/ha or more, 3250 g ai/ha or more, 3300 g ai/ha or more, 3400 g ai/ha or more, 3500 g ai/ha or more, 3750 g ai/ha or more, 4000 g ai/ha or more, 4250 g ai/
  • the FA/LSI herbicide can comprise orbencarb, or an agriculturally acceptable salt or ester thereof.
  • Orbencarb shown below, is a thiocarbamate herbicide used for pre-emergence control of annual grass, except wild oats, and broad-leaved weeds in barley, wheat, rye, maize, soybeans, cotton and turf, at 4000–5000 g/ha.
  • Orbencarb, as well as methods of preparing orbencarb, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Orbencarb can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • orbencarb is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 4000 g ai/ha or more, such as 4100 g ai/ha or more, 4200 g ai/ha or more, 4300 g ai/ha or more, 4400 g ai/ha or more, 4500 g ai/ha or more, 4600 g ai/ha or more, 4700 g ai/ha or more, 4800 g ai/ha or more, or 4900 g ai/ha or more; in an amount of 5000 g ai/ha or less, such as 4900 g ai/ha or less, 4800 g ai/ha or less, 4700 g ai/
  • the FA/LSI herbicide can comprise prosulfocarb, or an agriculturally acceptable salt or ester thereof.
  • Prosulfocarb shown below, is a thiocarbamate herbicide used for pre- and early post-emergence control of grass and broad-leaved weeds in winter wheat, winter barley and rye, at 3000–4000 g/ha.
  • Prosulfocarb, as well as methods of preparing prosulfocarb, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Prosulfocarb can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • prosulfocarb is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 250 g ai/ha or more, such as 260 g ai/ha or more, 270 g ai/ha or more, 275 g ai/ha or more, 280 g ai/ha or more, 290 g ai/ha or more, 300 g ai/ha or more, 310 g ai/ha or more, 320 g ai/ha or more, 325 g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 370
  • the FA/LSI herbicide can comprise thiobencarb, or an agriculturally acceptable salt or ester thereof.
  • Thiobencarb shown below, is a thiocarbamate herbicide used for pre- to early post-emergence control of Echinochloa, Leptochloa and Cyperus spp. and other grass and annual broad-leaved weeds in direct-seeded and transplanted rice, at 1500–7500 g/ha.
  • Thiobencarb, as well as methods of preparing thiobencarb are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • Thiobencarb can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • thiobencarb is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1100 g ai/ha or more, such as 1120 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1600 g ai/ha or more, 1700 g ai/ha or more, 1750 g ai/ha or more, 1800 g ai/ha or more, 1900 g
  • the FA/LSI herbicide can comprise tiocarbazil, or an agriculturally acceptable salt or ester thereof.
  • Tiocarbazil shown below, is a thiocarbamate herbicide used for pre- or post-emergence control of grass weeds, e.g., Echinochloa spp. and Lolium perenne, and sedge weeds, e.g., Cyperus spp., in rice paddies, at 4000 g/ha.
  • Tiocarbazil, as well as methods of preparing tiocarbazil are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, Seventeenth Edition, 2016.
  • the FA/LSI herbicide can comprise tri-allate, or an agriculturally acceptable salt or ester thereof.
  • Tri-allate shown below, is a thiocarbamate herbicide used for pre-plant or post-plant incorporated control of wild oats and some annual grass weeds in wheat, barley, rye, field beans, peas, lentils, beets, oilseed rape, maize, flax, alfalfa, clover, vetches, sainfoin, safflowers, sunflowers and vegetables, at 1120–1680 g/ha. Tri-allate, as well as methods of preparing tri-allate, are known in the art.
  • Tri-allate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • tri-allate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1100 g ai/ha or more, such as 1120 g ai/ha or more, 1150 g ai/ha or more, 1200 g ai/ha or more, 1250 g ai/ha or more, 1300 g ai/ha or more, 1350 g ai/ha or more, 1400 g ai/ha or more, 1450 g ai/ha or more, 1500 g ai/ha or more, 1550 g ai/ha or more, 1600 g ai/ha or more, 1650 g ai/ha or more, or 1680 g ai/ha or more; in an amount of 1700 g ai/ha or less, such as 1680 g ai/ha or less, 1650 g ai/ha or less, 1600 g ai/
  • the FA/LSI herbicide can comprise vernolate, or an agriculturally acceptable salt or ester thereof.
  • Vernolate shown below, is a thiocarbamate herbicide used for pre-plant or post-plant incorporated control of wild oats and some annual grass weeds in wheat, barley, rye, field beans, peas, lentils, beets, oilseed rape, maize, flax, alfalfa, clover, vetches, sainfoin, safflowers, sunflowers and vegetables, at 1120–1680 g/ha. Vernolate, as well as methods of preparing vernolate, are known in the art.
  • Vernolate can be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to induce a herbicidal effect.
  • vernolate is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1500 g ai/ha or more, such as 1600 g ai/ha or more, 1700 g ai/ha or more, 1750 g ai/ha or more, 1800 g ai/ha or more, 1900 g ai/ha or more, 2000 g ai/ha or more, 2100 g ai/ha or more, 2200 g ai/ha or more, 2300 g ai/ha or more, 2400 g ai/ha or more, 2500 g ai/ha or more, 2600 g ai/ha or more, 2700 g ai/ha or more, 2800 g ai/ha or more, or 2900 g ai/ha or more; in an amount of 3000 g ai/ha or less, such as 2900 g ai/ha or
  • Broclozone the ISO name for 2-[(2-bromo-4-chlorophenyl)methyl]-4,4-dimethyl- 3-isoxazolidinone (CAS No. 2766607-82-1), is a DOXP-inhibiting oxazole herbicide from Qingdao KingAgroot Chemical Compound Co. and is disclosed in WO202302027.
  • Broclozone may be used with foliar and/or soil applications, and may be used on crops such as wheat, soybeans, peanuts, oilseed rape, cabbage, rice, cotton, garlic, and watermelon.
  • Broclozone may be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 300 g ai/ha or more, such as 310 g ai/ha or more, 320 g ai/ha or more, 330 g ai/ha or more, 340 g ai/ha or more, 350 g ai/ha or more, 360 g ai/ha or more, 370 g ai/ha or more, 380 g ai/ha or more, 390 g ai/ha or more, 400 g ai/ha or more, 410 g ai/ha or more, 420 g ai/ha or more, 430 g ai/ha or more, 440 g ai/ha or more, 450 g ai/ha or more, 460 g ai/ha or more, 480 g ai/ha or more, 500 g ai/
  • Flufenoximacil Flufenoximacil the ISO name for methyl (2R)-2-[[(E)-[[2-chloro-5-[3,6-dihydro- 3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4- fluorophenyl]methylene]amino]oxy]propanoate (CAS No. 2759011-88-4), is a phenyluracil herbicide for non-selective weed control from Qingdao KingAgroot Chemical Compound Co. and is described in U.S Patent Application Publication No.2023/0111310.
  • Flufenoximacil is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 2 g ai/ha or more, 2.5 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai
  • Flusulfinam Flusulfinam the ISO name for 2-fluoro-N-(5-methyl-1,3,4-oxadiazol-2-yl)-3- (propylsulfinyl)-4-(trifluoromethyl)benzamide (the (R)-enantiomer), is an amide herbicide from Qingdao KingAgroot Chemical Compound Co., and is described in US Patent Application Publication No.2023/0041563.
  • Flusulfinam is effective in controlling weeds commonly found around rice crops (such as indica rice, japonica rice), gramineous weed (such as rice barnyardgrass, Qianjinjin, barnyard grass, horse tang, Setaria), broad-leaved weeds (such as gazania, velvetleaf, amaranth, chickweed), and sedge weeds (such as sedge, fireflies).
  • rice crops such as indica rice, japonica rice
  • gramineous weed such as rice barnyardgrass, Qianjinjin, barnyard grass, horse tang, Setaria
  • broad-leaved weeds such as gazania, velvetleaf, amaranth, chickweed
  • sedge weeds such as sedge, fireflies.
  • Flusulfinam is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 2 g ai/ha or more, 2.5 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai
  • Icafolin Icafolin the ISO name for (2RS,4RS)-4-( ⁇ [(5S)-3-(3,5-difluorophenyl)-5-vinyl- 4,5-dihydroisoxazol-5-yl]carbonyl ⁇ amino)tetrahydrofuran-2-carboxylic acid (including combinations of the (2S,4S), (2R,4R) isomers), is an isoxazole herbicide from Bayer AG (CAS Reg. No.
  • Icafolin can be applied pre-emergence or post-emergence to control various weeds, such as butilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Echinochloca crus, during preemergence treatment. gallium, Hordeum murinum, Lolium rigidum, Pharitis purpurea, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronica persica and Viola tricolor.
  • weeds such as butilon theophrasti, Alopecurus myosuroides, Amaranthus retroflexus, Avena fatua, Echinochloca crus, during preemergence treatment.
  • gallium Hordeum murinum, Lolium rigidum, Pharitis purpurea, Polygonum convolvulus, Setaria viridis, Stellaria media, Veronica persica and Viola tricolor.
  • Icafolin is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 1 g ai/ha or more, such as 2 g ai/ha or more, 2.5 g ai/ha or more, 3 g ai/ha or more, 4 g ai/ha or more, 5 g ai/ha or more, 6 g ai/ha or more, 7 g ai/ha or more, 8 g ai/ha or more, 9 g ai/ha or more, 10 g ai/ha or more, 12.5 g ai/ha or more, 15 g ai/ha or more, 17.5 g ai/ha or more, 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha
  • Iptriazopyrid the ISO name for 3-[[(1-methylethyl)sulfonyl]methyl]-N-(5-methyl- 1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyridine-8-carboxamide, is an amide herbicide from Nissan Chemical Corp. (CAS Reg. No.1994348-72-9) and is disclosed in International PCT Application Publication Nos. WO2014192936 and WO2020189576 (polymorphic crystal forms of Iptriazopyrid may be used as an herbicide for paddy fields in any of the treatment methods of soil treatment and foliage treatment under flooding.
  • iptriazopyrid may also be used with crops such as corn, rice, wheat, barley, lime tree, embaku, sorghum, cotton, soybean, peanut, buckwheat, tensai, rapeseed, sunflower, sugar cane, tobacco and the like.
  • Iptriazopyrid may be applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g ai/ha or more, such as 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/ha or more, 130 g ai/ha or more, 140 g ai/ha or more, 150 g ai/ha or more, 160 g ai/ha or more, 170 g ai/ha or more, 180 g ai/ha or more, 190 g ai/ha or more, 200 g
  • Metproxybicyclone Metproxybicyclone the ISO name for the racemic mixture (1RS,5SR)-3-[2- methoxy-4-(prop-1-yn-1-yl)phenyl]-4-oxobicyclo[3.2.1]oct-2-en-2-yl methyl carbonate, available from Syngenta Crop Protection (CAS Reg. No. 1848207-89-5) and is described in International PCT Application Publication No. WO2015197468.
  • Metproxybicyclone is applied to vegetation or an area adjacent the vegetation or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 15 g ai/ha or more, such as 20 g ai/ha or more, 25 g ai/ha or more, 30 g ai/ha or more, 35 g ai/ha or more, 40 g ai/ha or more, 45 g ai/ha or more, 50 g ai/ha or more, 55 g ai/ha or more, 60 g ai/ha or more, 65 g ai/ha or more, 70 g ai/ha or more, 75 g ai/ha or more, 80 g ai/ha or more, 85 g ai/ha or more, 90 g ai/ha or more, 95 g ai/ha or more, 100 g ai/ha or more, 110 g ai/ha or more, 120 g ai/
  • substituted 5-membered ring molecules, compositions and methods of the appended claims are not limited in scope by the specific compositions and methods described herein, which are intended as illustrations of a few aspects of the claims and any compositions and methods that are functionally equivalent are intended to fall within the scope of the claims.
  • Various modifications of the substituted 5-membered ring molecules, compositions, and methods in addition to those shown and described herein are intended to fall within the scope of the appended claims.
  • Further, while only certain representative substituted 5-membered ring molecules, compositions and method steps disclosed herein are specifically described, other combinations of the compositions and method steps also are intended to fall within the scope of the appended claims, even if not specifically recited.

Abstract

L'invention concerne des molécules cycliques à 5 chaînons substituées substituées par des groupes benzyles fluorés et des groupes acides aminés de formule (I), et des dérivés de ceux-ci. Les molécules cycliques à 5 chaînons substituées ont une activité herbicide et peuvent être utilisées pour lutter contre la végétation indésirable. L'invention concerne également des compositions, des procédés de préparation et des procédés d'utilisation des molécules cycliques à 5 chaînons substituées pour lutter contre la végétation indésirable.
PCT/US2023/076654 2022-10-12 2023-10-12 Cycles à 5 chaînons substitués et leur utilisation en tant que pesticides WO2024081762A1 (fr)

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US7314849B2 (en) 2006-01-13 2008-01-01 Dow Agrosciences Llc 6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides
WO2022200208A1 (fr) * 2021-03-22 2022-09-29 Bayer Aktiengesellschaft Pyrrolidin-2-ones substituées, leurs sels et leur utilisation en tant que substances actives herbicides
WO2022268520A1 (fr) * 2021-06-21 2022-12-29 Bayer Aktiengesellschaft Utilisation de pyrrolidinones substituées ou de leurs sels pour augmenter la tolérance au stress des plantes

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US7314849B2 (en) 2006-01-13 2008-01-01 Dow Agrosciences Llc 6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides
WO2022200208A1 (fr) * 2021-03-22 2022-09-29 Bayer Aktiengesellschaft Pyrrolidin-2-ones substituées, leurs sels et leur utilisation en tant que substances actives herbicides
WO2022268520A1 (fr) * 2021-06-21 2022-12-29 Bayer Aktiengesellschaft Utilisation de pyrrolidinones substituées ou de leurs sels pour augmenter la tolérance au stress des plantes

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