EA046295B1 - COMPOSITIONS CONTAINING PYRIDINE CARBOXYLATE-BASED HERBICIDES AND PDS INHIBITOR HERBICIDES - Google Patents

Description

Cross reference to related applications

This application claims the benefit of U.S. Provisional Patent Application No. 62/756,788, filed Nov. 07, 2018, which is incorporated herein by reference in its entirety.

Technical field of the invention

The present invention includes compositions containing: (a) a pyridine carboxylate herbicide or an agriculturally acceptable salt thereof and (b) a phytoene desaturase (PDS) inhibitor or an agriculturally acceptable salt or ester thereof. The present invention also includes methods for controlling unwanted vegetation using them.

State of the art

Many recurring problems in agriculture involve controlling the growth of undesirable vegetation, which can, for example, negatively affect the growth of target vegetation. To help control unwanted growth, researchers have come up with a variety of chemicals and chemical formulations that are effective in controlling such unwanted growth. However, there is a need for new herbicidal compositions and methods for suppressing the growth of unwanted vegetation among target crops.

Brief description of the invention

Disclosed herein are compositions that can be used as herbicides, for example, on agricultural crops. The compositions may contain (a) a pyridine carboxylate herbicide or an agriculturally acceptable salt or ester thereof and (b) a phytoene desaturase (PDS) inhibitor herbicide or an agriculturally acceptable salt or ester thereof. The weight ratio of (a) and (b) may be from 1:2000 to 12:1 (for example, from 1:280 to 2:1, from 1:30 to 10:10, from 1:24 to 1:18, from 1:16 to 1:12 or from 1:5 to 5:1).

In some aspects, the composition contains:

(a) a pyridine carboxylate herbicide defined by formula (I)

NHR ^{2 r3F} yV' θ

VN R ^{3 7} ' ^r! ' formula I, where R ¹ represents cyanomethyl or propargyl;

R ² and R ² represent hydrogen;

R ³ , R ³ , R ³ and R ³ represent hydrogen;

or an agriculturally acceptable salt thereof; and (b) a PDS inhibitor herbicide, or an agriculturally acceptable salt or ester thereof, wherein the pyridine carboxylate herbicide is used in an amount of at least 0.1 heq . k./ha, and the PDS inhibitor herbicide is applied in an amount of at least 12.5 g a. i./ha; and the weight ratio of the pyridine carboxylate herbicide (in g eq/ha) to the PDS inhibitor herbicide (in g ai/ha) is from 1:2000 to 12:1.

In some aspects, the composition contains:

(a) cyanomethyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridin-2-carboxylate, a pyridine carboxylate herbicidal compound, hereinafter referred to as compound

Compound A, or an agriculturally acceptable salt thereof; and (b) a phytoene desaturase (PDS) inhibitor, or an agriculturally acceptable salt or ester thereof.

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In some aspects, the composition contains:

(a) propargyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, a pyridine carboxylate herbicidal compound, hereinafter referred to as compound IN

Compound B, or an agriculturally acceptable salt thereof; and (b) a phytoene desaturase (PDS) inhibitor, or an agriculturally acceptable salt or ester thereof.

In some aspects, (b) the PDS inhibitor may include beflubutamide, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, or combinations thereof.

In some aspects, the composition contains a mixture of a pyridine carboxylate herbicide (a) and (b) a PDS inhibitor. In some aspects, the composition contains a mixture of pyridine carboxylate herbicides (a) and one or more (b) PDS inhibitors. In some aspects, the composition contains a mixture of one or more pyridine carboxylate herbicides (a) and one or more PDS inhibitors (b). In some aspects, (b) is a mixture of diflufenican and flurtamone.

In some aspects, the composition may further comprise an agriculturally acceptable excipient or carrier, a herbicidal antidote, an additional pesticide, or combinations thereof. In some aspects, the only active ingredients in the composition are (a) and (b). In some aspects, the composition may be provided as a herbicidal concentrate.

Also disclosed herein are methods for controlling unwanted vegetation, including applying to vegetation or an area adjacent to vegetation or to soil or water to inhibit the emergence or growth of vegetation, a composition containing (a) a pyridine carboxylate herbicide or a suitable herbicide thereof an agriculturally acceptable salt; and (b) a phytoene desaturase (PDS) inhibitor or an agriculturally acceptable salt or ester thereof, wherein the pyridine carboxylate herbicide is used in an amount of at least 0.1 g eq. k./ha, where the PDS inhibitor herbicide is applied in an amount of at least 12.5 g a. i./ha; and wherein the weight ratio of the pyridine carboxylate herbicide (in g eq/ha) and the PDS inhibitor herbicide (in g ai/ha) is from 1:2000 to 12:1.

In some aspects, (a) and (b) apply simultaneously. In some aspects, (a) and (b) are applied sequentially. In some aspects, (a) and (b) are applied before the emergence of unwanted vegetation. In some aspects, (a) and (b) are applied after the unwanted vegetation has emerged. In some aspects, the unwanted vegetation is found in cereal crops. In some aspects, the unwanted vegetation is found in maize, wheat, barley, rice, sorghum, millet, or oat species. In some aspects, unwanted vegetation is found in broadleaf crops. In some aspects, the unwanted vegetation is found in canola, flax, sunflower, soybean or cotton.

In some aspects, the pyridine carboxylate(a) herbicide can be applied in an amount from 0.1 grams acid equivalent per hectare (g eq/ha) to 300 g eq. k./ha (for example, from 30 g eq. k./ha to 40 g eq. k./ha). In some aspects, (b) the PDS inhibitor may be used in an amount of 12.5 g a. i./ha up to 4500 g a. i./ha (for example, from 30 g a.i./ha to 400 g a.i./ha). In some cases, (a) and (b) may be used in a weight ratio of 1:2000 to 12:1 (e.g., 1:280 to 2:1, 1:30 to 10:1, 1:24 to 1:18 or from 1:16 to 1:12).

The description below sets forth details of one or more aspects of the present invention. Other properties, purposes and advantages will be apparent from the present description and claims.

Detailed description

The present invention includes compositions containing (a) a pyridine carboxylate herbicide or an agriculturally acceptable salt thereof and (b) a phytoene desaturase (PDS) inhibitor or an agriculturally acceptable salt or ester thereof, wherein the pyridine carboxylate herbicide is used in an amount of at least 0.1 g eq. k./ha, where the PDS inhibitor herbicide is applied in an amount of at least 12.5 g a. i./ha; and wherein the weight ratio of the pyridine carboxylate herbicide (in g eq/ha) and the PDS inhibitor herbicide (in g ai/ha) is from 1:2000 to 12:1.

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The present invention also includes methods for controlling unwanted vegetation. In some aspects, the unwanted vegetation is found in cereal crops. In some aspects, the unwanted vegetation is found in maize, wheat, barley, rice, sorghum, millet, or oat species. In some aspects, unwanted vegetation is found in broadleaf crops. In some aspects, the unwanted vegetation is found in canola, flax, sunflower, soybean or cotton.

I. Definitions.

Terms used herein will have their commonly accepted meaning in the art unless otherwise noted. Singular forms include plural references unless otherwise noted. In cases in which the conjunction or is used (for example, A or B), it is intended to mean A or B, or both. If this disclosure is intended to refer only to A or B, but not both, then the expression only A or B, but not both, will be used. Thus, the use of the conjunction or in this document is an inclusive and not an exclusive use.

Chemical moieties mentioned in the definition of variable positions within the general formula described herein (eg, the term alkyl) are collective terms for the individual substituents covered by the chemical moiety. The prefix Cn-Cm preceding a group or fragment indicates in each case the possible number of carbon atoms in the group or fragment that follow it.

As used herein, the terms herbicide and herbicidal active ingredient can be understood to include an active ingredient that kills, controls or otherwise adversely modifies the growth of vegetation, particularly unwanted vegetation such as weed species, when applied in an appropriate amount.

As used herein, the term herbicidal effect can be understood to include the adverse modifying effect of the active ingredient on vegetation, including, for example, deviation from natural growth or development, killing, controlling, dehydration, growth inhibition, growth reduction and growth retardation. The term herbicidal activity generally refers to the herbicidal effects of the active ingredient. As used herein, the expression warns or similar expressions, such as warning, may be understood by one of ordinary skill to include any combination that exhibits a herbicidal effect or reduces the competitiveness of the weed relative to the crop.

As used herein, the expression application of a herbicide or herbicidal composition means its delivery directly to the target vegetation, or where it grows, or to an area where control of unwanted vegetation is necessary. Methods of application include, but are not limited to, bringing soil or water into contact before emergence, bringing unwanted vegetation into contact, or bringing an area adjacent to unwanted vegetation into contact after emergence.

As used herein, the term vegetation may include, for example, dormant seeds, sprouted seeds, emerging seedlings, plants developing from vegetative cuttings, immature vegetation, and established vegetation.

As used herein, the term crop refers to target vegetation, such as plants grown for food, shelter, pasture, erosion control, etc. Examples of crops include cereals, legumes, vegetables, fruiting plants and logs, types of cultivated grapes, etc. Preferably, the herbicides or herbicidal compositions have no or minimal herbicidal effect on crops.

As used herein, the term undesirable vegetation refers to vegetation that is undesirable in a specified area, such as weed species. Herbicides or herbicidal compositions are used to control unwanted vegetation. Preferably, the herbicides or herbicidal compositions have a significant or pronounced herbicidal effect against unwanted vegetation.

As used herein, the term active ingredient or a. And. can be understood to include a chemical compound or composition that has an effect on vegetation, for example, a herbicidal effect or a vegetation preservative effect.

As used herein, the term acid equivalent or equivalent. can be understood to include the amount of the acid form of the active ingredient, which is calculated on the basis of the amount of the salt or ester form of the active ingredient. For example, if the acid form of active ingredient Z has a molecular weight of 100 Da and the salt form of Z has a molecular weight of 130 Da, the application is 130 ha. i./ha of salt Z will be equal to the use of 100 g eq. k./ha acid form Z: 130 g a. i./ha salt Z · (100 Da acid Z/130 Da salt Z) represents 100 g eq. K./ha acid Z.

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Unless otherwise indicated, the term acyl as used herein may be intended to include a group of the formula -C(O)R, where C(O) is a short form for C=O. In the acyl group, R may be alkyl (eg C1- _C6 alkyl), haloalkyl (eg C1- _C6 haloalkyl), alkenyl (eg _C2 - _C6 alkenyl), haloalkenyl (eg _C2 - _C6 haloalkenyl), alkynyl (eg C ₂ -C ₆ alkynyl), aryl or heteroaryl, or arylalkyl (eg C 7 -C 10 arylalkyl).

As used herein, the term alkyl may be intended to include saturated, straight-chain, branched or cyclic saturated hydrocarbon moieties. Unless otherwise indicated, C1- _C20 alkyl groups are meant (eg _{C1 - C12} , _C1 - _C1o , C1-C8, _C1 - _C6 or _C1C4 ). Examples of alkyl groups include methyl, ethyl, propyl, cyclopropyl, 1-methylethyl, butyl, cyclobutyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, cyclopentyl, 1-methylbutyl, 2methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, cyclohexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2- dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1- ethyl-1-methylpropyl and 1-ethyl-2methylpropyl. Alkyl substituents may also be substituted by one or more chemical moieties. Examples of suitable substituents include, for example, hydroxy, nitro, cyano, formyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₆ -haloalkoxy, C ₁ -C ₆ -acyl, C ₁ -C ₆ -alkylthio, C ₁ - C ₆ haloalkylthio, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -haloalkylsulfinyl, C 1 -C ₆ -alkylsulfonyl, C _{1 -C 6} haloalkylsulfonyl, C ₁ -C ₆ -alkoxycarbonyl, C ₁ -C ₆ -haloalkoxycarbonyl , C ₁ -C ₆ -carbamoyl, C ₁ C6-halocarbamoyl, hydroxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, aminocarbonyl, C1-C6-alkylaminocarbonyl, haloalkylaminocarbonyl, C1-C6-dialkylaminocarbonyl and C1-C6dihaloalkylaminocarbonyl , at provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied. Preferred substituents include cyano and C1-C6 alkoxy.

As used herein, the term haloalkyl may be intended to include alkyl groups in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Unless otherwise indicated, C1- _C20 alkyl groups are meant (eg C1- _C12 , C1-C10, C1-C8, C1-C6 or C1- _C4 ). 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-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl. Haloalkyl substituents may also be substituted by one or more chemical moieties. Examples of suitable substituents include, for example, hydroxy, nitro, cyano, formyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 acyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1 -C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C1-C6-carbamoyl, C1-C6-halocarbamoyl, hydroxycarbonyl, _C1 - _C6 -alkylcarbonyl , C ₁ -C ₆ -haloalkylcarbonyl, aminocarbonyl, C ₁ -C ₆ alkylaminocarbonyl, haloalkylaminocarbonyl, C ₁ -C ₆ -dialkylaminocarbonyl and C ₁ -C ₆ -dihaloalkylaminocarbonyl, provided that the substituents are sterically compatible and the rules of chemical bonding and deformation energy. Preferred substituents include cyano and C ₁ -C ₆ -alkoxy.

As used herein, the term alkoxy may include a group of the formula RO-, wherein R is unsubstituted or substituted alkyl as defined above. Unless otherwise specified, alkoxy groups are meant wherein R is a Cj-C'20 alkyl group (eg C1- _C12 , C1-C10, C1-C8, C1- _C6 or C1- _C4 ). Examples include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1methylbutyloxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy.

As used herein, the term alkoxycarbonyl may be intended to include a group of the formula -C(O)OR, wherein R is unsubstituted or substituted alkyl as defined above. Unless otherwise specified, alkoxycarbonyl groups are meant, where R represents a C1- _C20 alkyl group (eg C1- _C12 , C1- _C10 , C1-C8, C1-C6 or C1-C4). Examples include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1methylpropoxycarbonyl, 2-methylpropoxycarbonyl, 1,1-dimethylethoxycarbonyl, pentoxycarbonyl, 1methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl bonyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3

- 4 046295 dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl -1-methylpropoxycarbonyl and 1-ethyl-2-methylpropoxycarbonyl.

As used herein, the term haloalkoxy may be intended to include a group of the formula RO-, wherein R is an unsubstituted or substituted haloalkyl as defined above. Unless otherwise indicated, haloalkoxy groups are meant, where R represents a C ₁ -C ₂₀ -alkyl group, (for example, C ₁ -C ₁₂ , C ₁ -C _1O , C ₁ -C ₈ , C ₁ -C ₆ or C ₁ -C ₄ ). 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.

As used herein, the term aryl, as well as derivative terms such as aryloxy, can be understood to include groups that include a monovalent aromatic carbocyclic group of 6-14 carbon atoms. Aryl groups may include a single ring or multiple fused rings. In some aspects, aryl groups include C6-C10 aryl groups. Examples of aryl groups include, but are not limited to, phenyl, biphenyl, naphthyl, tetrahydronaphthyl, phenylcyclopropyl and indanyl. In some aspects, the aryl group may be a phenyl, indanyl, or naphthyl group.

As used herein, the term heteroaryl, as well as derivative terms such as heteroaryloxy, may imply the inclusion of a 5- or 6-membered aromatic ring containing one or more heteroatoms, such as N, O, or S. Heteroaryl rings may be fused to other aromatic systems . Aryl or heteroaryl substituents may also be substituted by one or more chemical moieties. Examples of suitable substituents include, for example, hydroxy, nitro, cyano, formyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1 -C6acyl, C1-C6-alkylthio, C1-C6-alkylsulfinyl, _C1 -C6-alkylsulfonyl, C1- _C6 -alkoxycarbonyl, _C1 - _C6 -carbamoyl, hydroxycarbonyl, _C1 - _C6 -alkylcarbonyl, aminocarbonyl, C ₁ -C ₆ alkylaminocarbonyl, C ₁ -C ₆ -dialkylaminocarbonyl, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied. Preferred substituents include halogen, C ₁ -C ₄ alkyl and C ₁ -C ₄ haloalkyl.

As used herein, the term halogen, including derivative terms such as halogen, means fluorine, chlorine, bromine and iodine.

As used herein, agriculturally acceptable salts and esters may be intended to include salts and esters that exhibit herbicidal activity or that are or can be converted in plants, water or soil into the herbicide mentioned. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, for example, in plants, water, or soil, to the corresponding carboxylic acid, which depending on pH may be in dissociated or undissociated form.

The compounds described herein may include N-oxides. Pyridine N-oxides can be prepared by oxidation of the corresponding pyridines. Suitable oxidation methods are described, for example, in Houben-Weyl, Methoden der organischen Chemie [Methods in organic chemistry], expanded and subsequent volumes to the 4th edition, volume E 7b, page 565 f.

II. Herbicides based on pyridine carboxylate.

The compositions and methods of the present invention include a composition containing:

(a) a pyridine carboxylate herbicide defined by formula (I)

NHR ²

formula I, where R ¹ represents cyanomethyl or propargyl;

R ² and R ² independently represent hydrogen, C ₁ -C ₆ alkyl, formyl, alkoxycarbonyl or acyl;

R ³ , R ³ , R ³ and R ³ are independently hydrogen, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, ^-C^alkoxy or ^-C^haloalkoxy;

or an agriculturally acceptable N-oxide, salt or ester thereof; and (b) a phytoene desaturase (PDS) inhibitor or an agriculturally acceptable salt or ester thereof.

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In some aspects, the composition contains:

(a) cyanomethyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridin-2-carboxylate, a pyridine carboxylate herbicidal compound, hereinafter referred to as compound A

Compound A, or an agriculturally acceptable N-oxide, salt or ester thereof; and (b) a phytoene desaturase (PDS) inhibitor, or an agriculturally acceptable salt or ester thereof.

In some aspects, the composition contains:

(a) propargyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-III-indol-6-yl)pyridine-2-carboxylate, a pyridine carboxylate herbicidal compound, hereinafter referred to as compound IN

NH ₂

R.-L^.CI

T T ,,CH compound B, or an agriculturally acceptable N-oxide, salt or ester thereof; and (b) a phytoene desaturase (PDS) inhibitor or an agriculturally acceptable salt or ester thereof.

The pyridine carboxylate herbicides defined by formula (I), as well as methods for preparing such pyridine carboxylate herbicides, are disclosed in application PCT/US2018/031004, filed May 4, 2018, the entire disclosure of which is expressly incorporated herein by reference.

In some aspects, the pyridine carboxylate herbicide may be provided in the form of an agriculturally acceptable salt. Exemplary agriculturally acceptable pyridine carboxylate herbicide salts include, but are not limited to, sodium salts, potassium salts, ammonium salts, or substituted ammonium salts, particularly mono-, di-, and _tri - _C1C8 -alkylammonium salts such as methyl ammonium, dimethylammonium and isopropylammonium, mono-, di- and trihydroxy-C ₂ -C ₈ -alkylammonium salts, such as hydroxyethylammonium, di(hydroxyethyl)ammonium, tri(hydroxyethyl)ammonium, hydroxypropylammonium, di(hydroxypropyl)ammonium and tri(hydroxypropyl) salts ammonium, olamine salts, diglycolamine salts, choline salts and quaternary ammonium salts, such as those represented by the formula R ⁹ R ¹⁰ R ¹¹ R ¹² N ⁺ , and each of R ⁹ , R ¹⁰ , R ¹¹ and R ¹² (for example, R9 -R ¹² ) may independently represent hydrogen, ^-C alkyl, C ₂ -C ₈ -alkenyl, C ₂ C ₈ -alkynyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₈ -alkylthio or aryl groups , provided that R9-R ¹² are sterically compatible.

In some aspects, the pyridine carboxylate herbicide may be provided as an agriculturally acceptable ester. Exemplary agriculturally acceptable pyridine carboxylate herbicide esters include, but are not limited to: methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl , 1-ethylpropyl, hexyl, 1-methylhexyl (mexyl), 2-ethylhexyl, heptyl, 1-methylheptyl (meptyl), octyl, isooctyl (isoctyl), butoxyethyl (butothyl) and benzyl.

A pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof may be applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in quantity , sufficient to determine the herbicidal effect. In some aspects, a pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof is applied to vegetation or an area adjacent to vegetation, or is applied to soil or water to prevent the emergence or growth of vegetation in an amount of 0.1 grams of acid equivalent per hectare (g eq./ha) or more, such as 0.2 g eq. k./ha or more, 0.3 g eq. k./ha or more, 0.4 g eq. k./ha or more, 0.5 g eq. k./ha or more, 0.6 g eq. k./ha or more, 0.7 g eq. k./ha or more, 0.8 g eq. k./ha or more, 0.9 g eq. k./ha or more, 1 g eq. k./ha or more, 1.1 g eq.

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k./ha or more, 1.2 g eq. k./ha or more, 1.3 g eq. k./ha or more, 1.4 g eq. k./ha or more, 1.5 g eq. k./ha or more, 1.6 g eq. k./ha or more, 1.7 g eq. k./ha or more, 1.8 g eq. k./ha or more, 1.9 g eq. k./ha or more, 2 g eq. k./ha or more, 2.25 g eq. k./ha or more, 2.5 g eq. k./ha or more, 2.75 g eq. k./ha or more, 3 g eq. k./ha or more, 4 g eq. k./ha or more, 5 g eq. k./ha or more, 6 g eq. k./ha or more, 7 g eq. k./ha or more, 8 g eq. k./ha or more, 9 g eq. k./ha or more, 10 g eq. k./ha or more, 11 g eq. k./ha or more, 12 g eq. k./ha or more, 13 g eq. k./ha or more, 14 g eq. k./ha or more, 15 g eq. k./ha or more, 16 g eq. k./ha or more, 17 g eq. k./ha or more, 18 g eq. k./ha or more, 19 g eq. k./ha or more, 20 g eq. k./ha or more, 22 g eq. k./ha or more, 24 g eq. k./ha or more, 25 g eq. k./ha or more, 26 g eq. k./ha or more, 28 g eq. k./ha or more, 30 g eq. k./ha or more, 32 g eq. k./ha or more, 34 g eq. k./ha or more, 35 g eq. k./ha or more, 36 g eq. k./ha or more, 38 g eq. k./ha or more, 40 g eq. k./ha or more, 42.5 g eq. k./ha or more, 45 g eq. k./ha or more, 47.5 g eq. k./ha or more, 50 g eq. k./ha or more, 52.5 g eq. k./ha or more, 55 g eq. k./ha or more, 57.5 g eq. k./ha or more, 60 g eq. k./ha or more, 65 g eq. k./ha or more, 70 g eq. k./ha or more, 75 g eq. k./ha or more, 80 g eq. k./ha or more, 85 g eq. k./ha or more, 90 g eq. k./ha or more, 95 g eq. k./ha or more, 100 g eq. k./ha or more, 110 g eq. k./ha or more, 120 g eq. k./ha or more, 130 g eq. k./ha or more, 140 g eq. k./ha or more, 150 g eq. k./ha or more, 160 g eq. k./ha or more, 170 g eq. k./ha or more, 180 g eq. k./ha or more, 190 g eq. k./ha or more, 200 g eq. k./ha or more, 210 g eq. k./ha or more, 220 g eq. k./ha or more, 230 g eq. k./ha or more, 240 g eq. k./ha or more, 250 g eq. k./ha or more, 260 g eq. k./ha or more, 270 g eq. k./ha or more, 280 g eq. k./ha or more or 290 g eq. k./ha or more; in the amount of 300 g eq. k./ha or less, such as 290 g eq. k./ha or less, 280 g eq. k./ha or less, 270 g eq. k./ha or less, 260 g eq. k./ha or less, 250 g eq. k./ha or less, 240 g eq. k./ha or less, 230 g eq. k./ha or less, 220 g eq. k./ha or less, 210 g eq. k./ha or less, 200 g eq.

k./ha or less, 190 g eq. k./ha or less, 180 g eq. k./ha or less, 170 g eq. k./ha or less, 160 g eq. k./ha or less, 150 g eq. k./ha or less, 140 g eq. k./ha or less, 130 g eq. k./ha or less, 120 g eq. k./ha or less, 110 g eq. k./ha or less, 100 g eq. k./ha or less, 95 g eq.

k./ha or less, 90 g eq. k./ha or less, 85 g eq. k./ha or less, 80 g eq. k./ha or less, 75 g eq. k./ha or less, 70 g eq. k./ha or less, 65 g eq. k./ha or less, 60 g eq. k./ha or less, 57.5 g eq. k./ha or less, 55 g eq. k./ha or less, 52.5 g eq. k./ha or less, 50 g eq. k./ha or less, 47.5 g eq. k./ha or less, 45 g eq. k./ha or less, 42.5 g eq. k./ha or less, 40 g eq. k./ha or less, 38 g eq. k./ha or less, 36 g eq. k./ha or less, 35 g eq. k./ha or less, 34 g eq. k./ha or less, 32 g eq. k./ha or less, 30 g eq. k./ha or less, 28 g eq. k./ha or less, 26 g eq. k./ha or less, 25 g eq. k./ha or less, 24 g eq. k./ha or less, 22 g eq. k./ha or less, 20 g eq. k./ha or less, 19 g eq. k./ha or less, 18 g eq. k./ha or less, 17 g eq. k./ha or less, 16 g eq. k./ha or less, 15 g eq. k./ha or less, 14 g eq. k./ha or less, 13 g eq. k./ha or less, 12 g eq. k./ha or less, 11 g eq. k./ha or less, 10 g eq. k./ha or less, 9 g eq. k./ha or less, 8 g eq. k./ha or less, 7 g eq. k./ha or less, 6 g eq. k./ha or less, 5 g eq. k./ha or less, 4 g eq. k./ha or less, 3 g eq. k./ha or less, 2.75 g eq. k./ha or less, 2.5 g eq. k./ha or less, 2.25 g eq. k./ha or less, 2 g eq. k./ha or less, 1.9 g eq. k./ha or less, 1.8 g eq. k./ha or less, 1.7 g eq. k./ha or less, 1.6 g eq. k./ha or less, 1.5 g eq. k./ha or less, 1.4 g eq. k./ha or less, 1.3 g eq. k./ha or less, 1.2 g eq. k./ha or less, 1.1 g eq. k./ha or less, 1 g eq. k./ha or less, 0.9 g eq. k./ha or less, 0.8 g eq. k./ha or less, 0.7 g eq. k./ha or less, 0.6 g eq. k./ha or less, 0.5 g eq. k./ha or less, 0.4 g eq. k./ha or less, 0.3 g eq. k./ha or less or 0.2 g eq. kg/ha or less; or in an amount within any range defined between any pair of the preceding values, such as 0.1-300 g eq. k./ha, 1-150 g eq. k./ha, 10-200 g eq. k./ha, 25 g eq. k./ha - 75 g eq. k./ha or 40-100 g eq. k./ha.

III. Herbicides that are PDS inhibitors.

In addition to the pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt or ester thereof, the compositions may include a phytoene desaturase (PDS) inhibitor herbicide or an agriculturally acceptable salt or ester thereof. PDS inhibitors block carotenoid biosynthesis by inhibiting phytoene desaturase, a key enzyme in the carotenoid biosynthetic pathway. The absence of carotenoids leads to the destruction of membrane fatty acid and chlorophyll through excess energy. Examples of PDS inhibitors include, but are not limited to, beflubutamide, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon and picolinafen.

In some aspects, the composition may include a PDS inhibitor herbicide that is selected from the group consisting of beflubutamide, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, agriculturally acceptable salts and esters thereof, and combinations thereof.

The PDS inhibitor herbicide, or an agriculturally acceptable salt or ester thereof, may be applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent emergence or growth. vegetation in quantities sufficient to cause a herbicidal effect. In some aspects, a PDS inhibitor herbicide, or an agriculturally acceptable salt or ester thereof, is applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 12.5 grams of active ingredient per hectare (g a.i./ha) or more, such as 15 g a. i./ha or more, 20 g a. i./ha or more, 25 g a. i./ha or more, 30 g a. i./ha or more, 35 g a. i./ha or more, 40 g a. i./ha or more, 45 g a. i./ha or more, 50 g a. i./ha or more, 55 g a. i./ha or more, 60 g a. i./ha or more, 65 g a. i./ha or more, 70 g a. i./ha or more, 75 g a. i./ha or more, 80 g a. i./ha or more, 85 g a. i./ha or more, 90 g a. i./ha or more, 95 g a. i./ha or more, 100 g a. i./ha or more, 110 g a. i./ha or more, 120 g a. i./ha or more, 130 g a. i./ha or more, 140 g a. i./ha or more, 150 g a. i./ha or more, 160 g a. i./ha or more, 170 g a. i./ha or more, 180 g a. i./ha or more, 190 g a. i./ha or more, 200 g a. i./ha or more, 220 g a. i./ha or more, 240 g a. i./ha or more, 250 g a. i./ha,

260 g a. i./ha or more, 280 g a. i./ha or more, 300 g a. i./ha or more, 320 g a. i./ha or more,

340 g a. i./ha or more, 350 g a. i./ha or more, 360 g a. i./ha or more, 380 g a. i./ha or more,

400 g a. i./ha or more, 450 g a. i./ha or more, 500 g a. i./ha or more, 550 g a. i./ha or more,

600 g a. i./ha or more, 650 g a. i./ha or more, 700 g a. i./ha or more, 750 g a. i./ha or more,

800 g a. i./ha or more, 850 g a. i./ha or more, 900 g a. i./ha or more, 950 g a. i./ha or more,

1000 g a. i./ha or more, 1050 g a. i./ha or more, 1100 g a. i./ha or more, 1150 g a. i./ha or more, 1200 g a. i./ha or more, 1250 g a. i./ha or more, 1300 g a. i./ha or more, 1350 g a. i./ha or more, 1400 g a. i./ha or more, 1450 g a. i./ha or more, 1500 g a. i./ha or more, 1600 g a. i./ha or more, 1700 g a. i./ha or more, 1800 g a. i./ha or more, 1900 g a. i./ha or more, 2000 g a. i./ha or more, 2050 g a. i./ha or more, 2100 g a. i./ha or more, 2150 g a. i./ha or more, 2200 g a. i./ha or more, 2240 g a. i./ha or more, 2250 g a. i./ha or more, 2300 g a. i./ha or more, 2350 g a. i./ha or more, 2400 g a. i./ha or more, 2450 g a. i./ha or more, 2500 g a. i./ha or more, 2600 g a. i./ha or more, 2700 g a. i./ha or more, 2750 g a. i./ha or more, 2800 g a. i./ha or more, 2900 g a. i./ha or more, 3000 g a. i./ha or more, 3100 g a. i./ha or more, 3200 g a. i./ha or more, 3250 g a. i./ha or more, 3300 g a. i./ha or more, 3400 g a. i./ha or more, 3500 g a. i./ha or more, 3600 g a. i./ha or more, 3700 g a. i./ha or more, 3750 g a. i./ha or more, 3800 g a. i./ha or more, 3900 g a. i./ha or more, 3950 g a. i./ha or more, 4000 g a. i./ha or more, 4100 g a. i./ha or more, 4200 g a. i./ha or more, 4250 g a. i./ha or more, 4300 g a. i./ha or more, 4400 g a. i./ha or more or 4450 g a. i./ha or more; in the amount of 4500 g a. i./ha or less, such as 4450 g a. i./ha or less, 4400 g a. i./ha or less, 4300 g a. i./ha or less, 4250 g a. i./ha or less, 4100 g a. i./ha or less, 4000 g a. i./ha or less, 3950 g a. i./ha or less, 3900 g a. i./ha or less, 3800 g a. i./ha or less, 3750 g a. i./ha or less, 3700 g a. i./ha or less, 3600 g a. i./ha or less, 3500 g a. i./ha or less, 3400 g a. i./ha or less, 3300 g a. i./ha or less, 3250 g a. i./ha or less, 3200 g a. i./ha or less, 3100 g a. i./ha or less, 3000 g a. i./ha or less, 2900 g a. i./ha or less, 2800 g a. i./ha or less, 2750 g a. i./ha or less, 2700 g a. i./ha or less, 2600 g a. i./ha or less, 2500 g a. i./ha or less, 2450 g a. i./ha or less, 2400 g a. i./ha or less, 2350 g a. i./ha or less, 2300 g a. i./ha or less, 2250 g a. i./ha or less, 2240 g a. i./ha or less, 2200 g a. i./ha or less, 2150 g a. i./ha or less, 2100 g a. i./ha or less, 2050 g a. i./ha or less, 2000 g a. i./ha or less, 1900 g a. i./ha or less, 1800 g a. i./ha or less, 1750 g a. i./ha or less, 1700 g a. i./ha or less, 1600 g a. i./ha or less, 1500 g a. i./ha or less, 1450 g a. i./ha or less, 1400 g a. i./ha or less, 1350 g a. i./ha or less, 1300 g a. i./ha or less, 1250 g a. i./ha or less, 1240 g a. i./ha or less, 1200 g a. i./ha or less, 1150 g a. i./ha or less, 1100 g a. i./ha or less, 1050 g a. i./ha or less, 1000 g a. i./ha or less, 950 g a. i./ha or less, 900 g a. i./ha or less, 850 g a. i./ha or less, 800 g a. i./ha or less, 750 g a. i./ha or less, 700 g a. i./ha or less, 650 g a. i./ha or less, 600 g a. i./ha or less, 550 g a.

i./ha or less, 500 g a. i./ha or less, 450 g a. i./ha or less, 400 g a. i./ha or less, 380 g a.

i./ha or less, 360 g a. i./ha or less, 350 g a. i./ha or less, 340 g a. i./ha or less, 320 g a.

i./ha or less, 300 g a. i./ha or less, 280 g a. i./ha or less, 260 g a. i./ha or less, 250 g a.

i./ha or less, 240 g a. i./ha or less, 220 g a. i./ha or less, 200 g a. i./ha or less, 190 g a.

i./ha or less, 180 g a. i./ha or less, 170 g a. i./ha or less, 160 g a. i./ha or less, 150 g a.

i./ha or less, 140 g a. i./ha or less, 130 g a. i./ha or less, 120 g a. i./ha or less, 110 g a.

i./ha or less, 100 g a. i./ha or less, 95 g a. i./ha or less, 90 g a. i./ha or less, 85 g a. i./ha or less, 80 g a. i./ha or less, 75 g a. i./ha or less, 70 g a. i./ha or less, 65 g a. i./ha or less, 60 g a. i./ha or less, 55 g a. i./ha or less, 50 g a. i./ha or less, 45 g a. i./ha or less, 40 g a. i./ha or less, 35 g a. i./ha or less, 30 g a. i./ha or less, 25 g a. i./ha or less, 20 g a. i./ha or less or 15 g a. i./ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 12.5-4500 g a. i./ha, 15-2250 g a. i./ha, 20-2500 g a. i./ha, 25-3150 g a. i./ha, 30-900 g a. i./ha,

- 8 046295

45-4200 g a. i./ha, 50-1200 g a. i./ha, 50-4100 g a. i./ha, 60-750 g a. i./ha, 75-2100 g a. i./ha, 100-4000 g a. i./ha, 200-3600 g a. i./ha, 250-3000 g a. i./ha, 250-1000 g a. i./ha, 700-4250 g a. i./ha, 800-1400 g a. i./ha or 1000-3700 g a. i./ha.

In some aspects, the composition contains (a) a pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof and (b) diflufenican, flurtamone, picolinafen, or mixtures thereof.

Beflubutamide.

In some aspects, the PDS inhibitor herbicide may comprise beflubutamide or an agriculturally acceptable salt or ester thereof. Beflubutamide, shown below, is 2-[4-fluoro-3-(trifluoromethyl)phenoxy]-I-(phenylmethyl)butanamide. Its herbicidal activity is described, for example, by Tomlin, CDS, Ed. The Pesticide Manual: A World Compendium, ^17th ed.; BCPC: Alton, 2016 (hereinafter referred to in this document as The Pesticide Manual, Seventeenth Edition, 2016). Exemplary uses of beflubutamide 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.

Beflubutamide can be applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to cause a herbicidal effect. In some aspects, beflubutamide is applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 25 g a. i./ha or more, such as 30 g a. i./ha or more, 35 ha. i./ha or more, 40 g a. i./ha or more, 42.5 g a. i./ha or more, 45 g a. i./ha or more, 50 g a. i./ha or more, 60 g a. i./ha or more, 70 g a. i./ha or more, 80 g a. i./ha or more, 90 g a. i./ha or more, 100 g a. i./ha or more, 110 ha. i./ha or more, 120 g a. i./ha or more, 130 g a. i./ha or more, 140 g a. i./ha or more, 150 g a. i./ha or more, 160 g a. i./ha or more,

170 g a. i./ha or more, 180 g a. i./ha or more, 190 ha. i./ha or more, 200 g a. i./ha or more,

220 g a. i./ha or more, 240 g a. i./ha or more, 250 g a. i./ha or more, 255 g a. i./ha or more,

260 g a. i./ha or more, 270 g a. i./ha or more, 275 g a. i./ha or more, 280 g a. i./ha or more or 290 g a. i./ha or more; in the amount of 300 g a. i./ha or less, such as 290 g a. i./ha or less, 280 g a. i./ha or less, 275 g a. i./ha or less, 270 g a. i./ha or less, 260 g a. i./ha or less, 255 g a. i./ha or less, 250 g a. i./ha or less, 240 g a. i./ha or less, 220 g a. i./ha or less, 200 g a. i./ha or less, 190 g a. i./ha or less, 180 g a. i./ha or less, 170 g a. i./ha or less, 160 g a. i./ha or less, 150 g a. i./ha or less, 140 g a. i./ha or less, 130 g a. i./ha or less, 120 g a. i./ha or less, 110 g a. i./ha or less, 100 g a. i./ha or less, 90 g a. i./ha or less, 80 g a. i./ha or less, 70 g a. i./ha or less, 60 g a. i./ha or less, 50 g a. i./ha or less, 45 g a. i./ha or less, 42.5 g a. i./ha or less, 40 g a. i./ha or less, 35 ha. i./ha or less or 30 g a. i./ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 25-300 g a. i./ha, 45-250 g a. i./ha, 60-275 g a. i./ha, 120-255 g a. i./ha, 90-200 g a. i./ha, 130-260 g a. i./ha, 150-275 g a. i./ha or 42.5-300 g a. i./ha.

Diflufenican.

In some aspects, the PDS inhibitor herbicide may comprise diflufenican or an agriculturally acceptable salt or ester thereof. Diflufenican, as well as methods for producing diflufenican, are known in the art. Diflufenican, shown below, is N(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]-3-pyridinecarboxamide. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Illustrative uses of diflufenican include its use as a selective contact and post-emergence herbicide that is applied pre-emergence and early post-emergence to fall-seeded wheat and barley for grass and broadleaf control. weeds.

- 9 046295

Diflufenican can be applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to cause a herbicidal effect. In some aspects, diflufenican is applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g a. i./ha or more, such as 55 g a. i./ha or more, 60 g a. i./ha or more, 65 g a. i./ha or more, 70 g a. i./ha or more, 75 g a. i./ha or more, 80 g a. i./ha or more, 85 g more, more, more, more, more,

100

120

140

160

180 g y y y

A. i./ha a. i./ha a. i./ha a. i./ha a. i./ha or or or more, more, more, more,

105

125

145

165 g

g g

G

A.

A.

A.

A.

A. i./ha or more, 90 g a. i./ha or more, 95

and./ha and./ha and./ha and./ha or or or more, more, more, more,

110

130

150

170 g

g g

G

A. i./ha a. i./ha a. i./ha a. i./ha or or or more, more, more, more,

115

135

155

175 g y y y

A.

A.

A.

A.

A.

and./ha and./ha and./ha and./ha and./ha or or or or or more or 185 ha. i./ha or more; in the amount of 187.5 g a. i./ha or less, such as 185 g a. i./ha or less, 180 g a. i./ha or less, 175 g a. i./ha or less, 170 g a. i./ha or less, less, less, less, less,

165

145

125

105 g y y

A. i./ha or less, 160 g a. i./ha or less, 155

A. i./ha or less, 140 g a. i./ha or less, 135

A. i./ha or less, 120 g a. i./ha or less, 115

A. i./ha or less, 100 g a. i./ha or less, 95 g a. i./ha or less, 150 g a. i./ha or g a. i./ha or less, 130 g a. i./ha or g a. i./ha or less, 110 g a. i./ha or g a. i./ha or less, 90 g a. i./ha or g a. i./ha or less, 80 g a. i./ha or less, 75 g a. i./ha or less, 70 g a. i./ha or less, 65 g a. i./ha or less, 60 g a. i./ha or less or 55 g a. i./ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 50-187.5 g a. i./ha, 55-180 g a. i./ha, 60-175 g a. i./ha, 65-150 g a. i./ha, 70-175 g a. i./ha, 75-160 g a. i./ha, 80-180 g a. i./ha, 80-175 g a. i./ha, 85-185 g a. i./ha, 85-150 g a. i./ha, 90-185 g a. i./ha, 90-180 g a. i./ha, 90-175 g a. i./ha or 90-170 g a. i./ha.

Fluridone.

In some aspects, the PDS inhibitor herbicide may comprise fluridone or an agriculturally acceptable salt or ester thereof. Fluridone, shown below, is 1-methyl-3-phenyl-5-[3-(trifluoromethyl)phenyl]-4(III)-pyridinone. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Illustrative uses of fluridone include its use as an aquatic herbicide for the control of most partially or fully submerged aquatic plants (including Utricularia spp., Ceratophyllum demersum, Elodea canadensis, Myriophyllum spp. ., Najas guadalupensis, Potamogeton spp., Hydrilla verticillata and Panicum purpiirascens) in ponds, lakes, reservoirs, irrigation canals.

Fluridone can be applied to vegetation or an area adjacent to vegetation, or applied to water to prevent the emergence or growth of vegetation in an amount sufficient to cause a herbicidal effect. In some aspects, fluridone can be applied to water to prevent the emergence or growth of vegetation in an amount of 200 g a. i./ha or more, such as 220 g more, 240 more, 300 more, 360 more, 500 more, 700 g y y y

A. i./ha a. i./ha a. i./ha a. i./ha a. i./ha or or or or more, 250 more, 320 more, 380 more, 550 more, 750 g y y y

A. i./ha a. i./ha a. i./ha a. i./ha a. i./ha or more, 260 or more, 340 or more, 400 or more, 600 g

g g

G

A.

A.

A.

A.

and./ha and./ha and./ha and./ha or or or or more, 280 more, 350 more, 450 more, 650 g

g g

G

A.

A.

A.

A.

A.

and./ha and./ha and./ha and./ha and./ha or or or or or or more, 800 g a. i./ha or more or

850 g a. i./ha or more; in the amount of 900 g a. i./ha or less, such as 850 g a. i./ha or less, 800 g a. i./ha or or or or less, 750 less, 550 less, 380 less, 320 g

g g

G

A. i./ha or a. i./ha or a. i./ha or a. i./ha or less, 250 g a. i./ha or less, less, less, less, less,

700

500

360

300

240 g a.

g a.

g a.

g a.

g a.

and./ha and./ha and./ha and./ha or or or or

i./ha or less, 650 less, 450 less, 350 less, 280 g

g g

G

A.

A.

A.

A.

i./ha or less, 600

i./ha or less, 400

i./ha or less, 340

i./ha or less, 260 g

g g

G

A. i./ha a. i./ha a. i./ha a. i./ha less or 220 g a. i./ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 200-900 g a. i./ha, 280-750 g a. i./ha, 250-800 g a. i./ha, 450-600 g a. i./ha, 350-700 g a. i./ha, 250-650 g a. i./ha, 400-700 g a. i./ha or 220-900 g a. i./ha.

Flurochloridone.

In some aspects, the PDS inhibitor herbicide may comprise flurochloridone or an agriculturally acceptable salt or ester thereof. Flurochloridone, shown below, is 3-chloro-4-(chloromethyl)-1-[3-(trifluoromethyl)phenyl]-2-10046295 pyrrolidinone. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Illustrative uses of flurochloridone include its use for pre-emergence control of a wide range of broadleaf and grass weeds in sunflower species, carrot species and other umbrella crops, winter wheat, winter rye, and potato species. .

Flurochloridone can be applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to cause a herbicidal effect. In some aspects, flurochloridone is applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 200 g a. i./ha or more, such as 220 g a. i./ha or more, 240 g a. i./ha or more, 250 g a. i./ha or more, 260 g a. i./ha or more, 280 g a.

i./ha or more, 300 g a. i./ha or more, 320 g a. i./ha or more, 340 g a. i./ha or more, 350 g a.

i./ha or more, 360 g a. i./ha or more, 380 g a. i./ha or more, 400 g a. i./ha or more, 450 g a.

i./ha or more, 500 g a. i./ha or more, 550 g a. i./ha or more, 600 g a. i./ha or more, 650 g a.

i./ha or more, 700 g a. i./ha or more, 750 g a. i./ha or more, 800 g a. i./ha or more or 850 g a. i./ha or more; in the amount of 900 g a. i./ha or less, such as 850 g a. i./ha or less, 800 g a. i./ha or less, 750 g a. i./ha or less, 700 g a. i./ha or less, 650 g a. i./ha or less, 600 g a. i./ha or less, 550 g a. i./ha or less, 500 g a. i./ha or less, 450 g a. i./ha or less, 400 g a.

i./ha or less, 380 g a. i./ha or less, 360 g a. i./ha or less, 350 g a. i./ha or less, 340 g a.

i./ha or less, 320 g a. i./ha or less, 300 g a. i./ha or less, 280 g a. i./ha or less, 260 g a.

i./ha or less, 250 g a. i./ha or less, 240 g a. i./ha or less or 220 g a. i./ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 200-900 g a. i./ha, 220-750 g a. i./ha, 250-800 g a. i./ha, 450-900 g a. i./ha, 350-700 g a. i./ha, 250-600 g a. i./ha, 400-700 g a. i./ha or 500-900 g a. i./ha.

Flurtamon.

In some aspects, the PDS inhibitor herbicide may 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 described in The Pesticide Manual, Seventeenth Edition, 2016. Illustrative uses of flurtamone include its use for pre-plant, pre- or post-emergence control of broadleaf and some grass weeds in small grain crops, peanut species, cotton, pea species and types of sunflower.

Flurtamone can be applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in sufficient quantities to cause a herbicidal effect. In some aspects, flurtamone is applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 40 g a. i./ha or more, such as 42.5 g a. i./ha or more, g a. i./ha or more, 50 g a. i./ha or more, 60 g a. i./ha or more, 70 g a. i./ha or more, 80 g a.

and./ha and./ha and./ha and./ha and./ha and./ha and./ha and./ha and./ha and./ha or or or or or or or or more, 90 g a. i./ha or more,

100 g a. i./ha or more,

110 g a. i./ha or more, 120 g a.

more, 130 more, 170 more, 220 more, 260 more, 280 more, 300 more, 320 more, 340 more, 360 g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or more, 140 more, 180 more, 240 more, 265 more, 285 more, 305 more, 325 more, 345 g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or more, 150 more, 190 more, 250 more, 270 more, 290 more, 310 more, 330 more, 350 g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or more, 160 more, 200 more, 255 more, 275 more, 295 more, 315 more, 335 more, 355 g a. i./ha or more, 365 g a. i./ha or more or 370 g a. i./ha or more; in g a.

g a.

g a.

g a.

g a.

g a.

g a.

g a. quantity 11 046295 375 g a. i./ha or less, such as 370 g a. i./ha or less, 365 g a. i./ha or less, 360 g a. i./ha or less, 355 g a. i./ha or less, 350 g a. i./ha or less, 345 g a. i./ha or less,

340 g a. i./ha or less, 335 g a. i./ha or less, 330 g a. i./ha or less, 325 g a. i./ha or less,

320 g a. i./ha or less, 315 g a. i./ha or less, 310 g a. i./ha or less, 305 g a. i./ha or less,

300 g a. i./ha or less, 295 g a. i./ha or less, 290 g a. i./ha or less, 285 g a. i./ha or less,

280 g a. i./ha or less, 275 g a. i./ha or less, 270 g a. i./ha or less, 265 g a. i./ha or less,

260 g a. i./ha or less or 255 g a. i./ha or less, 250 g a. i./ha or less, 240 g a. i./ha or less, 220 g a. i./ha or less, 200 g a. i./ha or less, 190 g a. i./ha or less, 180 g a. i./ha or less, 170 g a. i./ha or less, 160 g a. i./ha or less, 150 g a. i./ha or less, 140 g a. i./ha or less, 130 g a. i./ha or less, 120 g a. i./ha or less, 110 g a. i./ha or less, 100 g a. i./ha or less, 90 g a. i./ha or less, 80 g a. i./ha or less, 70 g a. i./ha or less, 60 g a. i./ha or less, g a. i./ha or less, 45 g a. i./ha or less or 42.5 g a. i./ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 40-375 g a. i./ha, 125-355 g a. i./ha, 60-335 g a. i./ha, 80-300 g a. i./ha, 265-375 g a. i./ha, 170-325 g a. i./ha, 45-300 g a. i./ha, 190-375 g a. i./ha, 120-295 g a. i./ha, 180-355 g a. i./ha, 220-335 g a. i./ha or 42.5-325 g a. i./ha.

Norflurazon.

In some aspects, the PDS inhibitor herbicide may 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 described in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of norflurazon include its use for pre-emergence control of grass weeds and sedge species including Digitaria spp. (crabgrass species), Echinochloa spp. (barnyard spp.), Setaria spp. (bristleweed species) and Eleocharis acicularis, as well as broadleaf weeds such as Sida spinosa, Portulaca oleracea, Salsola spp. (Russian solyanka) and Capsella bursa-pastoris (shepherd's purse) in cotton, soybeans, peanuts, hops, gardens, ornamental plants and industrial areas.

Norflurazon can be applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to cause a herbicidal effect. In some aspects, norflurazon is applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 500 g a. i./ha or more, such as 550 g a. i./ha or more, 600 g a. i./ha or more, 650 g a. i./ha or more, 700 g a. i./ha or more, 750 g a. i./ha or more, 800 g a. i./ha or more, 850 g a. i./ha or more, 900 g a. i./ha or more, 950 g a. i./ha or more, 1000 g a. i./ha or more, 1050 g a. i./ha or more, 1100 g a. i./ha or more, 1150 g a. i./ha or more, 1200 g a. i./ha or more, 1250 g a. i./ha or more, 1300 g a. i./ha or more, 1350 g a. i./ha or more, 1400 g a. i./ha or more, 1450 g a. i./ha or more, 1500 g a. i./ha or more, 1600 g a. i./ha or more, 1700 g a. i./ha or more, 1800 g a. i./ha or more, 1900 g a. i./ha or more, 2000 g a. i./ha or more, 2050 g a. i./ha or more, 2100 g a. i./ha or more, 2150 g a. i./ha or more, 2200 g a. i./ha or more, 2240 g a. i./ha or more, 2250 g a. i./ha or more, 2300 g a. i./ha or more, 2350 g a. i./ha or more, 2400 g a. i./ha or more, 2450 g a. i./ha or more, 2500 g a. i./ha or more, 2600 g a. i./ha or more, 2700 g a. i./ha or more, 2750 g a. i./ha or more, 2800 g a. i./ha or more, 2900 g a. i./ha or more, 3000 g a. i./ha or more, 3100 g a. i./ha or more, 3200 g a. i./ha or more, 3250 g a. i./ha or more, 3300 g a. i./ha or more, 3400 g a. i./ha or more, 3500 g a. i./ha or more, 3600 g a. i./ha or more, 3700 g a. i./ha or more, 3750 g a. i./ha or more, 3800 g a. i./ha or more, 3900 g a. i./ha or more or 3950 g a. i./ha or more; in the amount of 4000 g a. i./ha or less, such as 3950 g a. i./ha or less, 3900 g a. i./ha or less, 3800 g a. i./ha or less, 3750 g a. i./ha or less, 3700 g a. i./ha or less, 3600 g a. i./ha or less, 3500 g a. i./ha or less, 3400 g a. i./ha or less, 3300 g a. i./ha or less, 3250 g a. i./ha or less, 3200 g a. i./ha or less, 3100 g a. i./ha or less, 3000 g a. i./ha or less, 2900 g a. i./ha or less, 2800 g a. i./ha or less, 2750 g a. i./ha or less, 2700 g a. i./ha or less, 2600 g a. i./ha or less, 2500 g a. i./ha or less, 2450 g a. i./ha or less, 2400 g a. i./ha or less, 2350 g a. i./ha or less, 2300 g a. i./ha or less, 2250 g a. i./ha or less, 2240 g a. i./ha or less, 2200 g a. i./ha or less, 2150 g a. i./ha or less, 2100 g a. i./ha or less, 2050 g a. i./ha or less, 2000 g a. i./ha or less, 1900 g a. i./ha or less, 1800 g a. i./ha or less, 1750 g a. i./ha or less, 1700 g a. i./ha or less, 1600 g a. i./ha or less, 1500 g a. i./ha or less, 1450 g a. i./ha or less,

- 12 046295

1400 g a. i./ha or less, 1350 g a. i./ha or less, 1300 g a. i./ha or less, 1250 g a. i./ha or less, 1240 g a. i./ha or less, 1200 g a. i./ha or less, 1150 g a. i./ha or less, 1100 g a. i./ha or less, 1050 g a. i./ha or less, 1000 g a. i./ha or less, 950 g a. i./ha or less, 900 g a. i./ha or less, 850 g a. i./ha or less, 800 g a. i./ha or less, 750 g a. i./ha or less, 700 g a. i./ha or less, 650 g a. i./ha or less, 600 g a. i./ha or less or 550 g a. i./ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 500-4000 g a. i./ha, 600-3600 g a. i./ha, 12503000 g a. i./ha, 2000-4000 g a. i./ha, 1700-3250 g a. i./ha, 2800-3950 g a. i./ha or 1000-3700 g a. i./ha.

Picolinafen.

In some aspects, the PDS inhibitor herbicide may comprise picolinafen or an agriculturally acceptable salt or ester thereof. Picolinafen, shown below, is N(4-fluorophenyl)-6-[3-(trifluoromethyl)phenoxy]-2pyridinecarboxamide. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of picolinafen include its use as a post-emergence herbicide, either alone or in mixtures, to control a wide range of weeds in cereal crops.

Picolinafen can be applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount sufficient to cause a herbicidal effect. In some aspects, picolinafen is applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 12.5 g a. i./ha or more, such as 15 g a. i./ha or more, 17.5 more, 27.5 more, 37.5 more, 47.5 more, 57.5 more, 67.5 more, 77.5 more, 87.5 g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or more, 20 more, 30 more, 40 more, 50 more, 60 more, 70 more, 80 more, 90 g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or more, 22.5 more, 32.5 more, 42.5 more, 52.5 more, 62.5 more, 72.5 more, 82.5 more, 92.5 g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or more, 25 more, 35 more, 45 more, 55 more, 65 more, 75 more, 85 more, 95 g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or g a. i./ha or more or 97.5 g a. i./ha or more; in quantity or less, 92.5 g a. i./ha or less, 82.5 g a. i./ha or less, 72.5 g a. i./ha or less, 62.5 g a. i./ha or less, 52.5 g a. i./ha or less, 42.5 g a. i./ha or less, 32.5 g a. i./ha or less, 90 g a. i./ha or less, 80 g a. i./ha or less, 70 g a. i./ha or less, 60 g a. i./ha or less, 50 g a. i./ha or less, 40 g a. i./ha or less, 30 g a. i./ha

100 g a. i./ha or less, such as 95 or less, 87.5 g a. i./ha or less, 77.5 g a. i./ha or less, 67.5 g a. i./ha or less, 57.5 g a. i./ha or less, 47.5 g a. i./ha or less, 37.5 g a. i./ha or less, 27.5 g a. i./ha g a. i./ha or less, 85 g a. i./ha or less, 75 g a. i./ha or less, 65 g a. i./ha or less, 55 g a. i./ha or less, 45 g a. i./ha or less, 35 g a. i./ha or less, 25 g a. i./ha or less, 22.5 g a. i./ha or less, 20 g a. i./ha or less, 17.5 g a. i./ha or less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 12.5-100 g a. i./ha, 15-90 g a. i./ha, 20-80 g a. i./ha, 25-75 g a. i./ha, 25-95 g a. i./ha, 25-8o g a. i./ha, 30-75 g a. i./ha, 35-90 g a. i./ha, 40-95 g a. i./ha, 40-75 g a. i./ha, 45-95 g a. i./ha, 45-90 g a. i./ha, 50-80 g a. i./ha or 50-75 g a. i./ha.

IV. Compositions.

A composition comprising (a) a pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt or ester thereof may be mixed with or used in combination with (b) a phytoene desaturase inhibitor or an agriculturally acceptable salt thereof or ester.

In some aspects, (a) and (b) are applied in an amount sufficient to cause an unexpectedly enhanced herbicidal effect (e.g., increased attack or damage to undesirable vegetation) while still demonstrating adequate compatibility with the crop (e.g., missing increased damage to the crop or very slightly increased damage or damage to the crop) compared to the use of herbicidal compounds (a) or (b) separately. In some aspects, the damage or damage to unwanted vegetation caused by the compositions and methods disclosed herein is assessed using a scale of 0% to 100% when compared to untreated control vegetation, where 0% indicates no growth.

- 13 046295 destruction of unwanted vegetation, and 100% indicates the complete destruction of unwanted vegetation.

In some aspects, the combined action of: (a) a pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt or ester thereof and (b) a PDS inhibitor herbicide or an agriculturally acceptable salt or ester thereof ester results in an unexpectedly enhanced herbicidal effect on undesirable vegetation, even at lower application rates than would normally be used for the herbicide to exert a herbicidal effect on its own. In some aspects, the compositions and methods disclosed herein can be used with individual components at lower application rates to achieve herbicidal effect comparable to that obtained with the individual components at optimal application rates.

In some aspects, the weight ratio of (a) a pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof (in g eq/ha) and (b) a PDS inhibitor herbicide, or its agriculturally acceptable salt or ester (in g a.i./ha) may be 1:9000 or more, such as 1:8000 or more, 1:7500 or more, 1:7000 or more, 1:6500 or more, 1:6000 or more,

1:5500 or more, 1:5000 or more, 1:4500 or more, 1:4000 or more, 1:3800 or more,

1:3600 or more, 1:3400 or more, 1:3200 or more, 1:3000 or more, 1:2800 or more,

1:2600 or more, 1:2400 or more, 1:2200 or more, 1:2000 or more, 1:1800 or more,

1:1600 or more, 1:1400 or more, 1:1200 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 more, 1:50 or more, 1:40 or more, 1:30 or more, 1:24 or more, 1:20 or more, 1:18 or more, 1:16 or more, 1:14 or more, 1:13 or more, 1:10 or more, 1:9 or more, 1:8 or more, 1:7 or more, 1:6 or more, 1:5 or more, 1:4 or more, 1: 3 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, 1.5:1 or more, 1.6:1 or more, 1.7:1 or more, 1.8:1 or greater than, 1.9:1 or greater, 2:1 or greater, 3:1 or greater, 4:1 or greater, 5:1 or greater, 6:1 or greater, 7:1 or greater, 8:1 or more, 9:1 or more, 10:1 or more, 12:1 or more, 14:1 or more, 15:1 or more, 16:1 or more, 18:1 or more, 20:1 or more, 22:1 or more or 23:1 or more; the weight ratio of (a) and (b) may be 24:1 or less, such as 23:1 or less, 22:1 or less, 20:1 or less, 18:1 or less, 16:1 or less , 15:1 or less, 14:1 or less, 12:1 or less, 20:1 or less, 10:1 or less, 9:1 or less, 8:1 or less, 7:1 or less, 6 :1 or less, 5:1 or less, 4:1 or less, 3:1 or less, 2:1 or less, 1.9:1 or less, 1.8:1 or less, 1.7:1 or less, 1.6:1 or less, 1.5:1 or less, 1.4:1 or less, 1.3:1 or less, 1.2:1 or less, 1.1:1 or less , 1:1 or less, 1:1.1 or less, 1:1.2 or less, 1:1.3 or less, 1:1.4 or less, 1:1.5 or less, 1:1 .6 or less, 1:1.7 or less, 1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:3 or less, 1:4 or less, 1:5 or less, 1:6 or less, 1:7 or less, 1:8 or less, 1:9 or less, 1:10 or less, 1:12 or less, 1:14 or less, 1:15 or less , 1:16 or less, 1:18 or less, 1:20 or less, 1:24 or less, 1:30 or less, 1:40 or less, 1:50 or less, 1:60 or less, 1 :70 or less, 1:80 or less,

1:90 or less, 1:100 or less, 1:200 or less, 1:300 or less, 1:400 or less, 1:500 or less, 1:600 or less, 1:700 or less, 1: 800 or less, 1:900 or less, 1:1000 or less, 1:1200 or less, 1:1400 or less, 1:1600 or less, 1:1800 or less, 1:2000 or less,

1:2200 or less, 1:2400 or less, 1:2600 or less, 1:2800 or less, 1:3000 or less,

1:3200 or less, 1:3400 or less, 1:3600 or less, 1:3800 or less, 1:4000 or less,

1:4500 or less, 1:5000 or less, 1:5500 or less, 1:6000 or less, 1:6500 or less,

1:7000 or less or 1:7500 or less; or the weight ratio of (a) and (b) may vary in a range of ratios from any of the minimum ratios to any of the maximum ratios set forth above, such as 1:8000 to 24:1, 1:6500 to 10 :1, 1:1500 to 12:1, 1:100 to 16:1, 1:24 to 1:18, 1:16 to 1:12 or 1:5 to 5:1.

In some aspects, the active ingredients in the compositions disclosed herein consist of (a) a pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof and (b) a PDS inhibitor herbicide, or its agriculturally acceptable salt or ester. In some aspects, the composition may include other components, such as antidotes or excipients, but does not include a herbicidal active ingredient in addition to (a) and (b). In some aspects, the compositions may not include one or more of the above herbicidal active ingredients. In some aspects, the compositions may include one or more herbicidal active ingredients in addition to (a) and (b), but may not include one or more of the above herbicidal active ingredients.

- 14 046295

In some aspects, (a) and (b) can be independently used at 90% to 100% purity (eg, 95% to 100%) as determined by nuclear magnetic resonance (NMR) spectroscopy.

V. Compositions.

The present invention also includes the compositions and methods disclosed herein.

A. Additives.

The compositions and methods disclosed herein may also be mixed or used with an additive. In some aspects, the additive is added sequentially. In some aspects, the additive is added simultaneously. In some aspects, the additive is premixed with a pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof.

1. Other pesticides.

Some aspects of the disclosed herbicidal compositions include adding one or more additional pesticide active ingredients to the herbicidal composition. Such pesticide active ingredients may include one or more of a herbicide, insecticide, fungicide, nematicide, miticide, arthropodocide, bactericide, plant growth regulator, or combinations thereof that are compatible with the compositions of the present invention.

In some aspects, the additive is an additional herbicide. For example, the compositions described herein can be used in combination with one or more additional herbicides to control unwanted vegetation. The composition may be formulated from one or more additional herbicides, formulated as a tank mix with one or more additional herbicides, or applied sequentially with one or more additional herbicides. Exemplary additional herbicides include, but are not limited to, 4-CPA, 4-CPB, 4-CPP, 2,4-D, choline salt 2,4-D, salts, esters and amines of 2,4-D, 2,4-DB, 3,4-DA, 3,4-DB, 2,4-DEB, 2,4-DEP, 2,4-DP, 3,4-DP, 2,3,6-TBA; 2,4,5-T, 2,4,5-TB, acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allylic alcohol, alorac, ametridione, ametrine, amibusin, amicarbazone, amidosulfuron, aminocyclopyrachlor, herbicides based 4-aminopicolinic acid, such as halauxifen, halauxifen-methyl, florpyrauxifen and the herbicides described in US Pat. Nos. 7,314,849 and 7,432,227 to Balko, et al.; aminopyralid, amiprofosmethyl, amitrol, ammonium sulfamate, anilofos, anizuron, asulam, atratone, atrazine, azaphenidine, azimsulfuron, aziprotrin, barban, BCRS, beflubutamide, benazolin, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron, benthiocar b, bentazone, benzadox, benzphendizone , benzipram, benzobicyclone, benzofenap, benzofluor, benzoylprop, benzthiazuron, bialaphos, bicyclopyrone, bifenox, bilanafos, bispyribac, borax, bromacil, bromobonil, bromobutide, bromophenoxime, bromoxynil, brompyrazone, butachlor, butafenacil, butamiphos, butenachlor, butidazole, butiuron, butralin , butroxydim, buturon, butylate, cacodylic acid, cafenstrol, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole, chlorprocarb, carfentrazone-ethyl, CDEA, SEPC, chlomethoxifene, chloramben, chloranocryl, chlorazifope, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazol, chlorflurenol, chloridazon, chlorimuron, chlornitrophen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorprofam, chlorsulfuron, chlorthal, chlorthiamide, cinidone-ethyl, cinmethylin, cinosulfuron, cisanilide, claciphos, clethodim, cliodinate, clodinaf op- propargyl, clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid, cloransulam-methyl, SMA, copper sulfate, CPMF, CPRS, credazine, cresol, cumyluron, cyanathrine, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop-butyl , cyperquat, cyprazine, cyprazole, cypromide, daimuron, dalapon, dazomet, delachlor, desmedipham, desmethrin, diallate, dicambu, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, dietamquat, dietyl, diphenopentene, difenoxuron , difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethamethrin, dimethenamid, dimethenamid-P, dimexano, dimidazone, dinitramine, dinophenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamide, dipropetrin, diquat, disul, dithiopyr, diuron, DM PA , DNOC, DSMA, EVER, eglinasine, endothal, epronaz, ERTS, erbon, esprocarb, ethalfluralin, etamethsulfuron, etbenzamide, etamethsulfuron, etidimuron, etiolate, ethobenzamide, etofumesate, ethoxyphene, ethoxysulfuron, etinophen, etnipromide, etobenzanide, EXD, fenasulam, phenopro n , fenoxaprop, fenoxaprop-P-ethyl, fenoxaprop-P-ethyl+isoxadifen-ethyl, fenoxasulfone, fenquinotrione, fenteracol, fentiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-R- butyl, fluazolate, flucarbazone, flusetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumetsulam, flumesin, flumiclorac-pentyl, flumioxazin, flumipropine, fluometuron, fluorodifen, fluoroglycophene, fluoromidin, fluoronitrophen, fluotiuron, flupoxam, flupropacil, flupropanate, flupirsulfuron, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, flutiacet, fomesafen, foramsulfuron, fosamine, furyloxifene, glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosate salts and esters,

- 15 046295 halosafen, halosulfuron, haloxidin, haloxyfop, hexachloracetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron , iodosulfuron-ethyl-sodium, iofensulfuron, ioxynil , ipazine, ipfencarbazone, iprimidam, isocarbamide, isocyl, isomethiosine, isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortol, isoxaflutole, isoxapirifop, carbutylate, ketospiradox, lactofen, lenacyl, linuron, MAA, MAMA, MCPA esters and amines , MSRAthioethyl, MSRP, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metham, metamifop, metamitron, metazachlor, metflurazon, metabenzthiazuron, metalpropalin, metazol, methiobencarb, methiozolin, met iuron, metometon, methoprothrin, methyl bromide , methylisothiocyanate, methyldimron, methobenzuron, metobromuron, metolachlor, methosulam, methoxuron, metribuzin, metsulfuron, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morphamquat, MSMA, naproanilide, napropamide, napropamide-M, napt alam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, orthodichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazone, oxapirazone, oxasulfuron, oxaziclomefon, oxyfluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate, pelargon oic acid, pendimethalin, penoxulam , pentachlorophenol, pentanochlor, pentoxazone, perfluidone, petoxamide, phenizofam, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercuracetate, pichloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron, procyazine , prodiamine, profluazole, profluralin, profoxydim, proglinazine, prohexadione-calcium, promethone, prometrin, pronamide, propachlor, propanil, propaquizafop, propazine, profam, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanone, pyraclonil, piraflu hair dryer, pyrasulfotol, pyrazogyl, pyrazone, pyrazolinate, pyrazosulfuron, pyrazoxifene, pyribenzoxime, pyributicarb, pyrichlor, pyridafol, pyridate, pyrifthalide, pyriminobac, pyrimisulfan, pyrithiobac sodium, pyroxasulfone, pyroxulam, quinclorac, quinmerac, quinoclamine, quinonamide, quizalofop, quizalofop-P- ethyl, quizalofop-P-tefuryl, rodetanil, rimsulfuron, saflufenacil, S-metolachlor, sebutylazine, secbumetone, sethoxydim, siduron, simazine, simeton, simethrine, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron , sulfosate, sulfosulfuron, sulfuric acid, sulglicapine, swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumetone, terbutylazine, terbutryn, tetrafluron, tenylchlor, thiameturon, thiazafluron, thiazopyr, thidiazimine, thidiazuron, thiencarbazone, thifensulfuron, thiobencarb, thiaphenacyl, thiocarbazyl, thioclorim, tolpyralate, topramesone, tralkoxydim, triallate, triafamone, triasulfuron, triaziflam, tribenuron, tribenuron, tricambu, trichloropyr choline salt, trichloropyr esters and amines, tridifane, triethazine, trifloxysulf damage, trifludimoxazine, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron, vernolate, xylachlor; as well as their salts, esters, optically active isomers and mixtures. In some aspects, the additional herbicide is selected from halauxifen, florpyrauxifen, flufenacet, iodosulfuron, mesosulfuron, an agriculturally acceptable salt or ester thereof, or combinations thereof.

An additional pesticide or an agriculturally acceptable salt or ester thereof may be applied to vegetation or an area adjacent to vegetation, or applied to soil or water, to prevent the emergence or growth of vegetation in an amount sufficient to determine the herbicidal effect. In some aspects, the additional pesticide or agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent to vegetation, or is applied to soil or water to prevent emergence or growth of vegetation in an amount of 12.5 grams active ingredient per hectare (g a.i./ha) or more, such as 15 g a. i./ha or more, 20 g a. i./ha or more, 25 g a. i./ha or more, 30 g a. i./ha or more, 35 g a. i./ha or more, 40 g a. i./ha or more, 45 g a. i./ha or more, 50 g a. i./ha or more, 55 g a. i./ha or more, 60 g a. i./ha or more, 65 g a. i./ha or more, 70 g a. i./ha or more, 75 g a. i./ha or more, 80 g a. i./ha or more, 85 g a. i./ha or more, 90 g a. i./ha or more, 95 g a. i./ha or more, 100 g a. i./ha or more, 110 g a. i./ha or more, 120 g a. i./ha or more, 130 g a. i./ha or more, 140 g a. i./ha or more, 150 g a. i./ha or more, 160 g a. i./ha or more,

170 g a. i./ha or more, 180 g a. i./ha or more, 190 g a. i./ha or more, 200 g a. i./ha or more,

220 g a. i./ha or more, 240 g a. i./ha or more, 250 g a. i./ha or more, 260 g a. i./ha or more,

280 g a. i./ha or more, 300 g a. i./ha or more, 320 g a. i./ha or more, 340 g a. i./ha or more,

350 g a. i./ha or more, 360 g a. i./ha or more, 380 g a. i./ha or more, 400 g a. i./ha or more,

450 g a. i./ha or more, 500 g a. i./ha or more, 550 g a. i./ha or more, 600 g a. i./ha or more,

650 g a. i./ha or more, 700 g a. i./ha or more, 750 g a. i./ha or more, 800 g a. i./ha or more,

850 g a. i./ha or more, 900 g a. i./ha or more, 950 g a. i./ha or more, 1000 g a. i./ha or more, 1050 g a. i./ha or more, 1100 g a. i./ha or more, 1150 g a. i./ha or more, 1200 g a. i./ha or more, 1250 g a. i./ha or more, 1300 g a. i./ha or more, 1350 g a. i./ha or more, 1400 g a. i./ha or

- 16 046295 more, 1450 g a. i./ha or more, 1500 g a. i./ha or more, 1600 g a. i./ha or more, 1700 g a. i./ha or more, 1800 g a. i./ha or more, 1900 g a. i./ha or more, 2000 g a. i./ha or more, 2050 g a. i./ha or more, 2100 g a. i./ha or more, 2150 g a. i./ha or more, 2200 g a. i./ha or more, 2240 g a. i./ha or more, 2250 g a. i./ha or more, 2300 g a. i./ha or more, 2350 g a. i./ha or more, 2400 g a. i./ha or more, 2450 g a. i./ha or more, 2500 g a. i./ha or more, 2600 g a. i./ha or more, 2700 g a. i./ha or more, 2750 g a. i./ha or more, 2800 g a. i./ha or more, 2900 g a. i./ha or more, 3000 g a. i./ha or more, 3100 g a. i./ha or more, 3200 g a. i./ha or more, 3250 g a. i./ha or more, 3300 g a. i./ha or more, 3400 g a. i./ha or more, 3500 g a. i./ha or more, 3600 g a. i./ha or more, 3700 g a. i./ha or more, 3750 g a. i./ha or more, 3800 g a. i./ha or more, 3900 g a. i./ha or more, 3950 g a. i./ha or more, 4000 g a. i./ha or more, 4100 g a. i./ha or more, 4200 g a. i./ha or more, 4250 g a. i./ha or more, 4300 g a. i./ha or more, 4400 g a. i./ha or more or 4450 g a. i./ha or more).

In some aspects, an additional pesticide or an agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 4500 g a. i./ha or less, such as 4450 g a. i./ha or less, 4400 g a. i./ha or less, 4300 g a. i./ha or less, 4250 g a. i./ha or less, 4100 g a. i./ha or less, 4000 g a. i./ha or less, 3950 g a. i./ha or less, 3900 g a. i./ha or less, 3800 g a. i./ha or less, 3750 g a. i./ha or less, 3700 g a. i./ha or less, 3600 g a. i./ha or less, 3500 g a. i./ha or less, 3400 g a. i./ha or less, 3300 g a. i./ha or less, 3250 g a. i./ha or less, 3200 g a. i./ha or less, 3100 g a. i./ha or less, 3000 g a. i./ha or less, 2900 g a. i./ha or less, 2800 g a. i./ha or less, 2750 g a. i./ha or less, 2700 g a. i./ha or less, 2600 g a. i./ha or less, 2500 g a. i./ha or less, 2450 g a. i./ha or less, 2400 g a. i./ha or less, 2350 g a. i./ha or less, 2300 g a. i./ha or less, 2250 g a. i./ha or less, 2240 g a. i./ha or less, 2200 g a. i./ha or less, 2150 g a. i./ha or less, 2100 g a. i./ha or less, 2050 g a. i./ha or less, 2000 g a. i./ha or less, 1900 g a. i./ha or less, 1800 g a. i./ha or less, 1750 g a. i./ha or less, 1700 g a. i./ha or less, 1600 g a. i./ha or less, 1500 g a. i./ha or less, 1450 g a. i./ha or less, 1400 g a. i./ha or less, 1350 g a. i./ha or less, 1300 g a. i./ha or less, 1250 g a. i./ha or less, 1240 g a. i./ha or less, 1200 g a. i./ha or less, 1150 g a. i./ha or less, 1100 g a. i./ha or less, 1050 g a. i./ha or less, 1000 g a. i./ha or less, 950 g a. i./ha or less, 900 g a. i./ha or less, 850 g a. i./ha or less, 800 g a. i./ha or less, 750 g a. i./ha or less, 700 g a. i./ha or less, 650 g a. i./ha or less,

600 g a. i./ha or less, 550 g a. i./ha or less, 500 g a. i./ha or less, 450 g a. i./ha or less,

400 g a. i./ha or less, 380 g a. i./ha or less, 360 g a. i./ha or less, 350 g a. i./ha or less,

340 g a. i./ha or less, 320 g a. i./ha or less, 300 g a. i./ha or less, 280 g a. i./ha or less,

260 g a. i./ha or less, 250 g a. i./ha or less, 240 g a. i./ha or less, 220 g a. i./ha or less,

200 g a. i./ha or less, 190 g a. i./ha or less, 180 g a. i./ha or less, 170 g a. i./ha or less,

160 g a. i./ha or less, 150 g a. i./ha or less, 140 g a. i./ha or less, 130 g a. i./ha or less,

120 g a. i./ha or less, 110 g a. i./ha or less, 100 g a. i./ha or less, 95 g a. i./ha or less, 90 g a. i./ha or less, 85 g a. i./ha or less, 80 g a. i./ha or less, 75 g a. i./ha or less, g a. i./ha or less, 65 g a. i./ha or less, 60 g a. i./ha or less, 55 g a. i./ha or less, g a. i./ha or less, 45 g a. i./ha or less, 40 g a. i./ha or less, 35 g a. i./ha or less, g a. i./ha or less, 25 g a. i./ha or less, 20 g a. i./ha or less or 15 g a. i./ha or less).

The additional pesticide or agriculturally acceptable salt or ester thereof may be applied to vegetation or an area adjacent to vegetation, or applied to soil or water, to prevent emergence or growth of vegetation in an amount ranging from any from the minimum values described above to any of the maximum values described above, for example, 12.5-4500 g a. i./ha, 15-2250 ha. i./ha, 20-2500 ha. i./ha, 25-3150 ha. i./ha, 30-900 ha. i./ha, 45-4200 ha. i./ha, 50-1200 g a. i./ha, 50-4100 g a. i./ha, 60-750 g a. i./ha, 75-2100 g a. i./ha, 100-4000 g a. i./ha, 200-3600 g a. i./ha, 250-3000 g a. i./ha, 250-1000 g a. i./ha, 700-4250 g a. i./ha, 800-1400 g a. i./ha or 1000-3700 g a. i./ha.

In some aspects, the additional pesticide or an agriculturally acceptable salt or ester thereof is premixed with (a) and (b) or combinations thereof. In some aspects, the pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt, or ester thereof is premixed with an additional pesticide. In some aspects, the PDS inhibitor herbicide, or an agriculturally acceptable salt or ester thereof, is premixed with an additional pesticide.

In some aspects, the compositions may include one or more herbicidal active ingredients in addition to (a) and (b). In some aspects, the compositions do not include a herbicidal active ingredient in addition to (a) and (b). In some aspects, the composition may include other components, such as antidotes or excipients, but does not include a herbicidal active

- 17 046295 ingredient in addition to (a) and (b). In some aspects, the compositions may not include one or more of the above herbicidal active ingredients. In some aspects, the compositions may include one or more herbicidal active ingredients in addition to (a) and (b), but may not include one or more of the above herbicidal active ingredients.

2. Excipients.

In some aspects, the additive includes an agriculturally acceptable excipient. Exemplary agriculturally acceptable excipients include, but are not limited to, antifreezes, antifoams, compatibilizers, binding agents, neutralizing agents and buffers, corrosion inhibitors, colorants, fragrances, penetration enhancers, wetting agents, distribution aids, dispersants, thickeners, freezing point depressants, antimicrobial agents, crop oil aids, adhesives (for example for use in seed treatment formulations), surfactants, protective colloids, emulsifiers, tackifiers and their mixtures.

Exemplary agriculturally acceptable excipients include, but are not limited to, crop oil excipient concentrates (eg, 85% mineral oil+15% emulsifiers); nonylphenol ethoxylates; benzylcocoalkyldimethyl quaternary ammonium salts; mixtures of petroleum hydrocarbons, alkyl esters, organic acids and anionic surfactants; C ₉ -C ₁₁ -alkyl polyglycoside; phosphoric acid and alcohol ethoxylates; natural primary (C ₁₂ -C ₁ 6) alcohol ethoxylate; di-sec-butylphenol block copolymers EO-PO; methyl-terminated polysiloxane; 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(400) dioleate-99.

Exemplary surfactants (e.g., wetting agents, tackifiers, dispersants, emulsifiers) include, but are not limited to, alkali metal salts, alkaline earth metal salts, and ammonium salts of fatty acids or aromatic sulfonic acids (e.g., lignosulfonic acids, phenolsulfonic acids, naphthalene sulfonic acids). acids and dibutylnaphthalene sulfonic acid); alkyl and alkylaryl sulfonates; alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates; salts of sulfated hexa-, hepta- and octadecanols; salts of glycol ethers of fatty alcohols; condensates of sulfonated naphthalene and its derivatives with formaldehyde; condensates of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde; polyoxyethylene octylphenol ether; ethoxylated isooctyl, octyl or nonylphenol, polyglycol ether of alkylphenyl or tributylphenyl; alkylaryl polyethers of alcohols; isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil; polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers; lauryl alcohol polyglycol ether acetate; sorbitol esters; spent lignosulfite solution and proteins, denatured proteins, polysaccharides (for example, methylcellulose); hydrophobically modified starches; and polyvinyl alcohol, polycarboxylates, polyalkoxylates, polyvinyl amine, polyethylenimine, polyvinylpyrrolidone and copolymers thereof.

Exemplary thickeners include, but are not limited to, polysaccharides (eg, xanthan gum), organic and inorganic leaf silicates, and mixtures thereof.

Exemplary antifoams include, but are not limited to, silicone-based emulsions, long chain alcohols, fatty acids, fatty acid salts, organofluorine compounds, and mixtures thereof.

Exemplary antimicrobial agents include, but are not limited to, dichlorophen and benzyl alcohol hemiformicides; isothiazolinone derivatives such as alkyl isothiazolinones and benzisothiazolinones, and mixtures thereof.

Exemplary antifreezes include, but are not limited to, ethylene glycol, propylene glycol, urea, glycerin, and mixtures thereof.

Exemplary colorants include, but are not limited to, the dyes known as 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, red pigment 112, red pigment 48:2, red pigment 48:1, red pigment 57:1, red pigment 53:1, orange pigment 43, orange pigment 34, orange pigment 5, green pigment 36, green pigment 7, white pigment 6, brown pigment 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.

3. Antidotes.

In some aspects, the additive is an antidote. Antidotes are compounds that lead to better compatibility of cultivated plants with the herbicide when applied. IN

- 18 046295 In some aspects, the antidote itself is herbicidal active. In some aspects, the antidote acts as an antidote or antagonist in crop plants and can protect crop plants from injury that might otherwise occur due to application of the herbicide. Exemplary antidotes include, but are not limited to, AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintoset, cloquintoset-mexil, ciometrinil, cyprosulfamide, daimuron, dichlormide, dicyclonone, dietolate, dimepiperate, disulfoton, fenchlorazole, fenchlorazole-ethyl, fenclor im, flurazol , fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaosi, mefenpyr, mefenpyr-diethyl, mephenate, naphthalene anhydride, 2,2,5-trimethyl-3-(dichloroacetyl)-1,3oxazolidine, 4-(dichloroacetyl) -1-oxa-4-azaspiro[4.5]decane, oxabetrinyl, R29148 and Nphenylsulfonylbenzoic acid amides, as well as their agriculturally acceptable salts and, provided they contain a carboxyl group, their agriculturally acceptable derivatives. In some aspects, the antidote may be cloquintoset or an ester or salt thereof, such as cloquintoset-mexil. In some aspects, the antidote may be mefenpyr or an ester or salt thereof, such as mefenpyr diethyl. In some aspects, the antidote is applied to rice, cereal or maize. For example, mefenpir or cloquintoset can be used to counteract the adverse effects of the compositions on rice, row crops and cereal crops.

4. Media.

In some aspects, the additive includes a carrier. In some aspects, the additive includes a liquid or solid carrier. In some aspects, 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, canola oil, olive oil, castor oil, sunflower oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil, etc., esters of the above vegetable oils, esters of monoalcohols or dibasic, tribasic or other lower polyalcohols ( containing 4-6 hydroxy groups), such as 2-ethylhexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, dioctyl succinate, dibutyl adipate, dioctyl phthalate, etc., esters of mono-, di- and polycarboxylic acids, etc., toluene , xylene, ligroin, oil crop aid, acetone, methyl ethyl ketone, cyclohexanone, trichlorethylene, perchlorethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerin, Nmethyl-2-pyrrolidinone; N.N-dimethylalkylamides, dimethyl sulfoxide and liquid fertilizers, as well as mixtures thereof. Exemplary solid carriers include, but are not limited to, silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, particulate synthetics, pyrophyllite clay , attapulgite clay, diatomaceous earth, calcium carbonate, bentonite clay, fuller's earth, cotton seed husk, wheat flour, soybean flour, pumice, wood flour, walnut flour, lignin, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, wholemeal flour grinding, tree bark meal, wood feed meal and nut shell meal, cellulose-based powders and mixtures thereof.

B. Physical condition.

In some aspects, a composition based on (a) a pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt or ester thereof and (b) a PDS inhibitor herbicide or an agriculturally acceptable salt or ester thereof. ester may be present in suspended, emulsified, dissolved or solid form. Illustrative formulations include, but are not limited to, aqueous solutions, aqueous suspensions, aqueous dispersions, aqueous emulsions, aqueous microemulsions, aqueous suspoemulsions, oil solutions, oil suspensions, oil dispersions, oil emulsions, oil microemulsions, oil suspoemulsions, self-emulsifying formulations, pastes, powders, dust preparations , granules and distribution materials.

In some aspects, (a) and (b) are aqueous solutions that can be diluted before use. In various aspects, (a) and (b) may be provided in the form of a concentrated formulation, such as a concentrate. In some aspects, the concentrate is stable and remains effective during storage and transportation. In various aspects, the concentrate is a clear, homogeneous liquid that is stable at temperatures of 54°C or higher. In some aspects, the concentrate does not exhibit any precipitation of solids at temperatures of -10°C or higher. In some aspects, the concentrate does not exhibit separation, precipitation, or crystallization of any of the components at low temperatures. For example, the concentrate remains a clear solution at temperatures below 0°C (eg, below -5°C, below -10°C, below -15°C). In some aspects, the concentrate has a viscosity of less than 50 centigrade

- 19 046295 typoise (50 megapascals), even at temperatures as low as 5°C. In some aspects, the concentrate does not experience separation, precipitation, or crystallization of any of the components during storage for a period of 2 weeks or longer (e.g., 4 weeks, 6 weeks, 8 weeks, 3 months, 6 months, 9 months, or 12 months or longer).

In some aspects, emulsions, pastes, or oil dispersions can be prepared by homogenizing (a) and (b) in water with a wetting agent, tackifier, dispersant, or emulsifier. In some aspects, concentrates suitable for dilution with water may be prepared comprising (a), (b), a wetting agent, a tackifier, and a dispersant or emulsifier.

In some aspects, powders, distribution materials, or particulate preparations can be prepared by mixing or simultaneously grinding (a) and (b), and optionally other additives, with a solid carrier.

In some aspects, granules (eg, coated granules, impregnated granules, and homogeneous granules) can be prepared by binding (a) and (b) to solid supports.

In some aspects, the formulations contain from 1% to 99% (a) and 1% to 99% (b), (e.g., 95% (a) and 5% (b); 70% (a) and 30% (b) ; or 40% (a) and 60% (b)) of the total weight of (a) and (b). In formulations intended for use as concentrates, (a) and (b) may be present in a total amount at a concentration of from about 0.1 to about 98 weight percent (wt.%) based on the total weight of the formulation. For example, (a) and (b) may be present in total concentrations of as little as about 1 wt.%, about 2.5 wt.%, about 5 wt.%, about 7.5 wt.%, about 10 wt. %, about 15 wt.%, about 20 wt.%, about 25 wt.%, about 30 wt.%, about 35 wt.%, about 40 wt.%, about 45 wt.%, to about 50 wt.%, about 55 wt.%, about 60 wt.%, about 65 wt.%, about 70 wt.%, about 75 wt.%, about 80 wt.%, about 85 wt.%, about 90 wt.%, about 95 wt.%, about 97 wt.%, or within any range defined by any two of the above values, for example from about 1 wt.% to about 97 wt.%, from about 10 wt.% to about 90 wt.%, from from about 20 wt.% to about 45 wt.% and from about 25 wt.% to about 50 wt.% based on the total weight of the composition. Before use, concentrates may be diluted with an inert carrier such as water. Diluted formulations applied to unwanted vegetation or the location of unwanted vegetation may contain from 0.0006 to 8.0 wt.% of the total amount of (a) and (b) (for example, from 0.001 to 5.0 wt.% ) in terms of the total weight of the diluted composition.

C. Packaging.

In some aspects, the composition may be in the form of a single package formulation comprising (a) a pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt or ester thereof and (b) a PDS inhibitor herbicide, or its agriculturally acceptable salt or ester. In some aspects, the composition may be presented in the form of a single package composition comprising (a) or (b) and further including at least one additive. In some aspects, the composition may be in the form of a formulation in multiple packages, such as in the form of a composition in two packages, where one package contains (a) and optionally at least one additive, while the other package contains (b) and optionally at least one additive. In some aspects, in the case of a two-pack formulation, the formulation comprising (a) and optionally at least one additive and the formulation comprising (b) and optionally at least one additive are mixed prior to use and then administered simultaneously. In some aspects, mixing is carried out as a tank mix (eg, the formulations are mixed immediately before or after dilution with water). In some aspects, the composition comprising (a) and the composition comprising (b) are not mixed, but are applied sequentially (in turn), for example, immediately or within 1 hour, within 2 hours, within 4 hours, within 8 hours, within 16 hours, within 24 hours, within 2 days or within 3 days between.

VI. Methods of application.

The compositions disclosed herein can be used in any known herbicide application technique. Exemplary application techniques include, but are not limited to, atomizing, misting, dusting, spreading, or direct application to water. The method of application may vary depending on the intended purpose. In some aspects, the method of application can be selected to provide the best possible distribution of the compositions described herein.

In some aspects, a method of controlling unwanted vegetation that involves contacting the vegetation or its habitat with any of the compositions or applying it to soil or water to prevent the emergence or growth of vegetation is disclosed herein.

The compositions disclosed herein can be applied pre-emergently (before

- 20 046295 emergence of unwanted vegetation) or after emergence (for example, during and/or after the emergence of unwanted vegetation). In some aspects, the composition is applied post-emergence to unwanted vegetation. In some aspects, a pyridine carboxylate herbicide and a PDS inhibitor herbicide are used simultaneously. In some aspects, the pyridine carboxylate herbicide and the PDS inhibitor herbicide are applied sequentially to each other, such as without or with minimal delay, within about 10 minutes, within about 20 minutes, within about 30 minutes, within about 40 minutes, within approximately 1 hour, within approximately 2 hours, within approximately 4 hours, within approximately 8 hours, within approximately 16 hours, within approximately 24 hours, within approximately 2 days, or within approximately 3 days .

When the compositions are applied to crops, the compositions can be applied after sowing and before or after emergence of the crop plants. In some aspects, the compositions disclosed herein exhibit good tolerance to the crop, even when the crop has already emerged, and can be applied during or after the crop has emerged. In some aspects, if the compositions are applied to crops, the compositions can be applied before the crop plants are sown.

In some aspects, the compositions disclosed herein are applied to vegetation or an area adjacent to vegetation, or applied to soil or water, to prevent the emergence or growth of vegetation through spraying (eg, foliar spraying). In some aspects, spray techniques use, for example, water as a carrier and spray at volume levels ranging from 2 liters per hectare (L/ha) to 2000 L/ha (for example, 10-1000 L/ha or 50-500 L /ha). In some aspects, the compositions disclosed herein are administered in a low-volume or ultra-low-volume manner, in which application is in the form of microbeads. In some aspects, if the compositions disclosed herein are not well tolerated by certain crop plants, the compositions can be applied using a spray device such that they come into little or no contact with the leaves of sensitive crop plants, while reaching the leaves of unwanted vegetation growing below or on bare soil (for example, post-emergence directional treatment or laying). In some aspects, the compositions disclosed herein can be administered in the form of dry formulations (eg, granules, powders, or dusts).

In some aspects, if unwanted vegetation is treated after emergence, the compositions described herein are applied through foliar application. In some aspects, the compounds in the mixture exhibit herbicidal activity when applied directly to the plant or plant site at any stage of growth or prior to planting or emergence. The observed effect may depend on the type of unwanted vegetation being controlled, the growth stage of the unwanted vegetation, application parameters such as dilution and droplet size of the spray liquid, particle size of the solid components, environmental conditions during application, the specific compound used, the specific excipients used and carriers, soil type, etc., and the amount of chemical used. In some aspects, these and other factors can be adjusted to provide non-selective or selective herbicidal effects.

The compositions and methods disclosed herein can be used to control unwanted vegetation in a variety of applications. The compositions and methods disclosed herein can be used to control unwanted vegetation in areas including, but not limited to, agricultural lands, lawn, pastures, meadows, natural grasslands, fallow land, rights-of-way, water installations, trees and vineyards, natural reserves or natural pasture. In some aspects, control of unwanted vegetation is carried out in a row crop. Exemplary crops include, but are not limited to, wheat, barley, triticale, rye, teff, oats, maize, cotton, soybeans, sorghum, rice, millet, sugarcane, and natural pasture (eg, pasture grasses). In some aspects, the compositions and methods disclosed herein can be used to control unwanted vegetation in maize, wheat, barley, rice, sorghum, millet, oat species, or combinations thereof. In some aspects, the compositions and methods disclosed herein can be used to control unwanted vegetation in broadleaf crops. In some aspects, the compositions and methods disclosed herein can be used to control unwanted vegetation in canola, flax, sunflower, soybean or cotton. In some aspects, the compositions and methods disclosed herein can be used for industrial vegetation control (IVM) or utility right-of-way, pipeline, roadside, and railroad applications. In some aspects of composition and

- 21 046295 The agents disclosed in this document can also be used in forestry (for example, for site preparation or for controlling unwanted vegetation in planted forests). In some aspects, the compositions and methods disclosed herein can be used to control unwanted vegetation on lands in a highly erodible conservation program (CRP), plantings, vineyards, meadows, and grasses grown for seed. In some aspects, the compositions and methods disclosed herein can be used on artificial lawns (eg, residential, industrial, and institutional), golf courses, parks, cemeteries, athletic fields, and turf farms.

The compositions and methods disclosed herein can also be applied to crop plants that are resistant to, for example, herbicides, pathogens and/or insects. In some aspects, the compositions and methods disclosed herein can be applied to crop plants that have been rendered resistant to one or more herbicides through genetic engineering or breeding. In some aspects, the compositions and methods disclosed herein can be applied to crop plants that are resistant to one or more pathogens, such as plant pathogenic fungi, due to the use of genetic engineering or breeding. In some aspects, the compositions and methods disclosed herein can be applied to crop plants that are resistant to insect attack due to genetic engineering or breeding. Exemplary resistant crops include, but are not limited to, crops that are resistant to photosystem II inhibitors, or crops that, due to the introduction of a Bacillus thuringiensis (or Bt) toxin gene by genetic modification, are resistant to attack by certain insects. In some aspects, the compositions and methods described herein can also be used in combination with glyphosate, glufosinate, dicamba, phenoxyauxins, pyridyloxyauxins, aryloxyphenoxypropionates, acetyl-CoA carboxylase (ACCase) inhibitors, imidazolinones, acetolactate synthase (ALS) inhibitors, 4 -hydroxyphenylpyruvate dioxygenase (HPPD), protoporphyrinogen oxidase (PPO) inhibitors, triazines and bromoxynil for vegetation control in crops with tolerance to glyphosate, glufosinate, dicamba, phenoxyauxins, pyridyloxyauxins, aryloxyphenoxypropionates, ACCase inhibitors, imidazolinones, synthetic herbicides auxin, HPPD inhibitors, PPO inhibitors, triazines, bromoxynil or combinations thereof. In some aspects, unwanted vegetation is controlled in crops with tolerance to glyphosate, glufosinate, dicamba, phenoxyauxins, pyridyloxyauxins, aryloxyphenoxypropionates, ACCase inhibitors, synthetic auxin herbicides, HPPD inhibitors, PPO inhibitors, triazines, and bromoxynil, having one or more or packaged features conferring tolerance to one or more chemicals and/or multiple mechanisms of action. In some aspects, unwanted vegetation can be controlled in a crop that is tolerant to ACCase, ALS, or a combination thereof. The combination of (a), (b) and optionally (c) can be used in combination with one or more herbicides that are selective for the crop to be treated and that complement the spectrum of weeds that the compounds control at the applied application rate. In some aspects, the compositions described herein and other complementary herbicides are applied at the same time, either as a combination formulation, tank mix, or sequential applications. The compositions and methods can be used in the control of undesirable vegetation in crops having tolerance to agronomic stress (including, but not limited to, drought, cold, heat, salinity, water, nutrients, fertility, pH), tolerance to pests (including, but not limited to insects). , fungi and pathogens) and signs of crop improvement (including, but not limited to, yield; protein, carbohydrate or oil content; protein, carbohydrate or oil composition; plant structure and plant architecture).

In some aspects, the compositions disclosed herein can be used to control unwanted vegetation, including grasses, broadleaf weeds, sedge weeds, and combinations thereof. In some aspects, the compositions disclosed herein can be used to control unwanted vegetation, including, but not limited to, Polygonum spp., Amaranthus spp., Chenopodium spp., Sida spp., Ambrosia spp., Cyperus spp., Setaria spp., Sorghum spp., Acanthospermum spp., Anthemis spp., Atriplex spp., Brassica spp., Cirsium spp., Convolvulus spp., Conyza spp., Cassia spp., Commelina spp., Datura spp., Euphorbia spp., Geranium spp., Galinsoga spp., Ipomea spp., Lamium spp., Lolium spp., Malva spp., Matricaria spp., Prosopis spp. , Rumex spp., Sisymbrium spp., Solanum spp., Trifolium spp., Xanthium spp., Veronica spp., and Viola spp. In some aspects, undesirable vegetation includes Stellaria media, Abutilon theophrasti, Sesbania exaltata Cory, Anoda cristata, Bidens pilosa, Brassica kaber, Capsella bursa-pastoris, Centaurea cyanus or Cyanus segetum), pi

- 22 046295 common grasshopper (Galeopsis tetrahit), bedstraw (Galium aparine), common sunflower (Helianthus annum), Desmodium tortuosum, multiflowered chaff (Lolium multiflorum), kochia scoparia, Medicago arabica, Mercurialis annua, Myosotis arvensis, poppy common sorrel (Papaver rhoeas), Raphanus raphanistrum, sorrel (Rumex obtusifolius), Russian solyanka (Salsola kali), field mustard (Sinapis arvensis), Sonchus arvensis, Thlaspi arvense, Tagetes minuta, Richardia brasiliensis, Plantago major, Plantago lanceolata, Persian speedwell (Veronica persica), amaranth (Amaranthus retroflexus), winter rape (Brassica napus), white pigweed (Chenopodium album), field thistle (Cirsium arvense), edible milkweed (Cyperus esculentus), variegated spurge (Euphorbia heterophylla), wild lettuce (Lactuca serriola), Lamium purpureum, Matricaria chamomilla, Matricaria inodora, Anthemis arvensis, Fagopyrum esculentum, Polygonum convulvus, Setaria faberi ), green bristle grass (Setaria viridis), common sorghum (Sorghum vulgare), tricolor violet (Viola tricolor) or combinations thereof.

The compositions described herein can be used to control weeds with herbicide resistance or tolerance. Methods using the compositions described herein can also be used to control weeds with herbicide resistance or tolerance. Exemplary weeds with resistance or tolerance include, but are not limited to, biotypes with resistance or tolerance to acetolactate synthase (ALS) or acetohydroxyacid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcar bamatam, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl-CoA carboxylase (ACCase) inhibitors (e.g. aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines), synthetic auxins (e.g. benzoic acids, phenoxycarboxylic acids, pyr idinecarboxylates , quinolinecarboxylic acids), auxin transport inhibitors (e.g., phthalamates, semicarbazones), photosystem I inhibitors (e.g., bipyridylium), 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthetase inhibitors (e.g., glufosinate, bialaphos), microtubule assembly inhibitors (e.g. benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (e.g. carbamates), very long chain fatty acid (VLCFA) inhibitors (e.g. acetamides, chloroacetamides, hydroxyacetamides, tetrazolinones) , fatty acid and lipid synthesis inhibitors (e.g. phosphorodithiolates, thiocarbamates, benzofurans, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibitors (e.g. diphenylethers, Nphenylphthalimides, oxadiazoles, oxazolidinediones, phenylpyrazolams, pyrimidinediones, thiadiazolams, triazolinones), biosynthesis inhibitors carotenoids (eg , clomazone, amitrol, aclonifen), phytoene desaturase (PDS) inhibitors (e.g. amides, anilidex, furanones, phenoxybutanamides, pyridiazinones, pyridines), 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors (e.g. callistemons, isoxazolams, pyrazolams, triketones), biosynthesis inhibitors cellulose (e.g. nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes of action such as quinclorac and unclassified herbicides such as arylaminopropionic acids, difenzoquat, endothal and organoarsenic compounds. Exemplary weeds with resistance or tolerance include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple classes of chemicals, biotypes with resistance or tolerance to multiple mechanisms of herbicidal action, and biotypes with multiple mechanisms resistance or tolerance (eg, target site resistance or metabolic resistance).

Below, for purposes of non-limiting illustration, examples of certain aspects of the present invention are provided. Parts and percentages are by weight unless otherwise noted.

Examples

Greenhouse test method - assessment of post-emergence herbicide effect.

Seeds of the required species of the studied plants were planted in a mixture of 90:10% v/v. (volume/volume) PRO-MIX® BX (Premier Tech Horticulture, Quakertown, PA, USA) and PROFILE® GREENS GRADE™ planting mixes (Profile Products LLC, Buffalo Grove, IL, USA), which typically characterized by a pH value of 5.2 to 6.2 and an organic content of at least 50 percent in plastic pots with a surface area of 103.2 square centimeters (cm ² ). In some aspects, fungicide and/or other chemical or physical treatments are used to ensure proper germination and healthy plants. Plants were grown for 7–36 days (d) in a greenhouse with an approximately 14-hour (h) photoperiod in which the temperature was maintained at approximately 23°C during the day and 22°C during the night. Nutrients and water were added regularly and provided where necessary.

- 23 046295 additional lighting with 1000 watt metal halide ceiling lamps. Plants were used for testing when they reached the second or third true leaf stage.

Emulsifiable concentrates of each pyridine carboxylate herbicide (Compound A or Compound B) were prepared at a concentration of 100 grams acid equivalent per liter (g eq/L). The emulsifiable concentrates also included the antidote, cloquintocet-mexil, with a concentration of 120 grams of 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 1.25% (v/v) ACTIROB® B esterified rapeseed oil (Bayer Crop Science, Research Triangle Park, NC, USA) or MSO® Concentrate with LECI-TECH® methylated soybean oil (Loveland Products, Loveland, CO, USA) to produce concentrated stock solutions at the highest application rate for each herbicide, based on an application volume of 12 milliliters (ml) at a rate of 187 liters per hectare ( l/ha). The concentrated stock solutions were further diluted with a 1.25% v/v aqueous mixture. ACTIROB® B or MSO® Concentrate with LECI-TECH® to produce stock solutions with reduced application rates for each herbicide. Solutions of herbicide spray combinations (Compound A or Compound B with PDS inhibitor herbicide) were prepared by adding weighed amounts or aliquots of PDS inhibitor herbicides to stock solutions of Compound A or Compound B to produce 12 ml spray solutions in two - or three-component combinations.

Spray solutions were applied to the plant material using a Mandel down-jet sprayer equipped with 8002E nozzles calibrated to deliver 187 L/ha to 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 plants were sprayed in the same way using solvent blank. All application rates for herbicide based on pyridine carboxylate (component a) are given in g equivalent. l./ha, and all rates of application of the herbicide, which is a PDS inhibitor (component b), are given in ha. i./ha.

Treated plants and control plants were placed in a greenhouse as described above and watered by subsurface irrigation to prevent leaching of test compounds. After 2022 days, the condition of the studied plants was visually determined in comparison with that of the control plants and assessed on a scale from 0 to 100 percent, where 0 corresponds to the absence of lesions and 100 corresponds to complete destruction.

Details of the compositions and crops tested are detailed in the following examples.

Example 1.

Compositions containing compound A and diflufenican were tested on undesirable vegetation species, including winter rape (BRSNW, Brassica napus), knotweed (POLCO, Polygonum convolvulus), field mustard (SINAR, Sinapis arvensis), Russian solyanka (SASKR, Salsola kali) , kochia (KCHSC, Kochia scoparia), white pigweed (CHEAL, Chenopodium album L), amaranth (AMARE, Amaranthus retroflexus), chamomile (MATCH, Matricaria chamomilla) and thistle (CIRAR, Cirsium arvense), in order to determine the effectiveness of the compositions against these types of unwanted vegetation. The compositions were also tested on spring wheat (TRZAS) and spring barley (HORVS) and the phytotoxicity of the compositions to each crop was measured.

The results are summarized in table. 1 below.

Table 1

Herbicidal effects (% visible damage) of compound A and diflufenican on weeds and grain crops

Application rate (g/ha) Compound A 7.5 10 0 7.5 10 Diflufenican 0 0 60 60 60 BRSNW 35 43 18 90 88 POLCO 78 93 10 95 97 SINAR 88 90 23 100 100 SASKR 60 63 18 68 73 KCHSC 63 63 13 65 68

- 24 046295

CHEAL 88 93 13 90 98 AMARE 78 73 20 88 93 MATCH 20 thirty 0 15 45 CIRAR thirty 40 5 75 78 TRZAS 0 0 0 0 0 HORVS 0 0 13 0 0

g/ha=grams per hectare

BRSNW=/4ra.s.s/cz7 napus (winter rape) POLCO=Polygonum convolvulus (convolvulus) STNAR.=Sinapis arvensis (field mustard) SASKR=54Zso/a kali (Russian solyanka) KCHSC=Xoc/wa scoparia (kochia)

C.V[E.\L=('he nopodium album L. (white pigweed) NMARE=Amaranthus retroflexus (amaranth) MATSN=LA///7С7//77/ chamomilla (chamomile) ClRAR=Cirsium arvense (field thistle) TRZAS =7/7//c7//7z aestivum (spring wheat) HORVS=Z/orafewm vulgarе (spring barley)

Example 2.

Compositions containing compound A and beflubutamide were tested on types of undesirable vegetation, including spring rape (BRSNN, Brassica napus), knotweed (POLCO, Polygonum convolvulus), field mustard (SINAR, Sinapis arvensis), Russian solyanka (SASKR, Salsola kali) , kochia (KCHSC, Kochia scoparia), white pigweed (CHEAL, Chenopodium album L.) and chamomile (MATCH, Matricaria chamomilla), in order to determine the effectiveness of the compositions against these types of unwanted vegetation. The compositions were also tested on spring wheat (TRZAS) and spring barley (HORVS) and the phytotoxicity of the compositions to each crop was measured.

The results are summarized in table. 2 below.

table 2

Herbicidal effects (% visible damage) of compound A and beflubutamide on weeds and grain crops

Application rate (g/ha) Compound A 7.5 10 0 7.5 10 Beflubutamide 0 0 42.5 42.5 42.5 BRSNN Observable 55 60 25 75 88 Expected — — — 66 70 R 9 18

- 25 046295

POLCO Observable 70 78 0 94 98 Expected — — — 70 78 P 24 20 SINAR Observable 88 92 5 99 100 Expected — — — 88 92 P 10 8 SASKR Observable 45 60 0 60 68 Expected — — — 45 60 R 15 8 KCHSC Observable 50 58 0 68 85 Expected — — — 50 58 R 18 28 CHEAL Observable 70 83 0 83 92 Expected — — — 70 83 R 13 9 MATCH Observable 13 15 0 20 50 Expected — — — 13 15 R 8 35 TRZAS Observable 0 0 0 0 0 Expected — — — 0 0 R 0 0 HORVS Observable 8 0 18 8 8 Expected — — — 24 18 R -16 -10

g/ha=grams per hectare

BRSNN=/ira.s.s/cz7 napus (spring rapeseed) POLCO=Polygomim convolvulus (convolvulus knotweed) S\NPJk=Sinapis arvensis (field mustard)

SASKR=Salsola kali (Russian solyanka) KCHSC=Xoc/wa scoparia (kochia) CYPENL=Chenopodium album L. (white pigweed) MATCH=A /77//7cz7/777 chamomilla (chamomile) TRZAS=7/7//c7 //77 aestivum (spring wheat) HORVS=Zforafewm vulgare (spring barley)

- 26 046295

Example 3.

Compositions containing compound A and fluridone were tested on types of undesirable vegetation, including spring rape (BRSNN, Brassica napus), knotweed (POLCO, Polygonum convolvulus), field mustard (SINAR, Sinapis arvensis), Russian solyanka (SASKR, Salsola kali) , amaranth (AMARE, Amaranthus retrojlexus), white pigweed (CHEAL, Chenopodium album L), chamomile (MATCH, Matricaria chamomilla) and thistle (CIRAR, Cirsium arvense), in order to determine the effectiveness of the compositions against these types of unwanted vegetation . The compositions were also tested on spring wheat (TRZAS) and spring barley (HORVS) and the phytotoxicity of the compositions to each crop was measured.

The results are summarized in table. 3 below.

Table 3

Herbicidal effects (% visible damage) of compound A and fluridone on weeds and grain crops

Application rate (g/ha) Compound A 7.5 10 0 7.5 10 Fluridone 0 0 280 280 280 BRSNN Observable 55 70 18 100 89 Expected — — — 63 75 R 37 13 POLCO Observable 88 96 13 98 95 Expected — — — 89 97 R 8 -2 SINAR Observable 85 90 45 100 100 Expected — — — 92 95 R 8 6 SASKR Observable 38 63 0 83 88 Expected — — — 38 63 R 45 25 AMARE Observable 70 98 23 98 100

- 27 046295

Expected — — — 77 98 P 21 2 CHEAT Observable 60 90 13 98 100 Expected — — — 65 91 R 33 9 MATCH Observable 0 33 5 93 95 Expected — — — 5 36 R 88 59 CIRAR Observable 10 23 18 80 85 Expected — — — 26 36 R 54 49 TRZAS Observable 0 0 0 0 0 Expected — — — 0 0 R 0 0 HORVS Observable 0 0 0 0 0 Expected — — — 0 0 R 0 0

g/ha=grams per hectare

BRSNN=Ara.s.s/cz/ napus (spring rapeseed)

POLCO=Polygonum convolvulus (convolvulus knotweed)

STNAR=Sinapis arvensis (field mustard)

SASKR=&Zso/a kali (Russian solyanka)

AMNRE=Amaranthus retroflexus (amaranth)

CW,NL=Chenopodium album L. (white pigweed)

MATCH=AA7//7cz7/7a chamomilla (chamomile)

CJRAR=Cirsium arvense (field thistle)

TRZAS=7/7//c7//77 aestivum (spring wheat)

HO9NS=Hordeum vulgare (spring barley)

Example 4.

Compositions containing compound A and picolinafen were tested on undesirable vegetation species including VIOTR, Viola tricolor, CHEAL, Chenopodium album L, LOLMU, Lolium multiflorum, and common rice (ORYSA, Oryza sativa ), common barnacle (ECHCG, Echinochloa crus-galli), blood-red crabgrass (DIGSA, Digitaria sanguinalis), Theophrastus rope (ABUTH, Abutilon theophrasti), field thistle (CIRAR, Cirsium arvense), spring rape (BRSNN, Brassica napus) , Faber's bristle grass (SETFA, Setaria faberi), common dock (RUMOB, Rumex obtusifolius), soybean (GLXMA, Glycine max) and morning glory (IPOHE, Ipomoea hederacea), in order to determine the effectiveness of the compositions against these types of unwanted vegetation.

The results are summarized in table. 4 below.

- 28 046295

Table 4

Herbicidal effects (% visible damage) of compound A and picolinafen on weeds

Application rate (g/ha) Compound A 7.5 10 0 7.5 10 Picolinafen 0 0 12.5 12.5 12.5 VIOTR Observable 10 18 0 45 53 Expected - - - 10 18 R 35 35 CHEAL Observable 97 93 20 100 100 Expected - - - 97 94 R 3 6 LOLMU Observable 0 0 0 10 18 Expected - - - 0 0 R 10 18 ORYSA Observable 13 10 5 35 45 Expected - - - 17 15 R 18 31 ECHCG Observable 73 78 0 84 92 Expected - - - 73 78 R 12 14 DIGSA Observable 45 25 50 75 80 Expected - - - 73 63 R 3 18 ABUTH Observable 68 78 15 82 78 Expected - - - 72 81 R 9 -3 CIRAR Observable 23 20 5 65 70 Expected - - - 26 24 R 39 46 BRSNN Observable 73 83 28 85 90

- 29 046295

Expected - - - 80 87 R 5 3 SETFA Observable 70 70 0 93 95 Expected - - - 70 70 R 23 25 RUMOB Observable 8 10 0 20 23 Expected - - - 8 10 R 13 13 GLXMA Observable 93 95 20 100 100 Expected - - - 94 96 R 6 4 IPOHE Observable 3 8 5 40 40 Expected - - - 7 12 R 33 28

g/ha=grams per hectare

VIOTR=J 7W<7 tricolor (tricolor violet)

CGEAE=Chenopodium album L. (white pigweed)

LOLMU=Zo/zwm multiflorum (multifloral chaff)

ORYSA=O/j'z<7 sativa (common rice)

ECHCG=Echinochloa crus-galli (common barnyard grass)

T)\GSA=Digitaria sanguinalis (blood red crabgrass)

ABUTH=4Z>zz/z7on theophrasti (Ropeman of Theophrastus)

CTRAR=C//'.s////77 arvense (field thistle)

BRSNN=/izzmzczz napus (spring rapeseed)

SETF\=Setaria faberi (Faber's bristleweed)

RUMOB=7?zzzzzex obtusifolius (blunt-leaved sorrel)

GLXMA=Glycine max (soybean)

ΙΡΟΗΕ=7ροζζζοβα hederacea (Ipomoea ivy)

Example 5.

Compositions containing Compound A, diflufenican and flurtamone were tested on undesirable vegetation species including viola tricolor (VIOTR, Viola tricolor), Abutilon theophrasti (ABUTH), bindweed (POLCO, Polygonum convolvulus), euphorbia varifolia (EPHHL, Euphorbia heterophylla), thistle (CIRAR, Cirsium arvense), morning glory (IPOHE, Ipomoea hederacea), amaranth (AMARE, Amaranthus retroflexus), common sunflower (HELAN, Helianthus annuus) and kochia (KCHSC, Kochia scoparia), in order to determine the effectiveness of the compositions in relation to these types of unwanted vegetation. The compositions were also tested on spring wheat (TRZAS) and the phytotoxicity of the compositions to this crop was measured.

The results are summarized in table. 5 below.

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Table 5

Herbicidal effects (% visible damage) of compound A, diflufenican and flurtamone against weeds and grain crops

Application rate (g/ha) Compound A 7.5 10 0 7.5 10 Diflufenican 0 0 51.5 51.5 51.5 Flurtamon 0 0 128.5 128.5 128.5 VIOTR Observable 3 3 5 thirty 28 Expected - - - 7 7 R 23 20 ABUTH Observable 40 48 15 83 75 Expected - - - 49 55 R 34 20 POLCO Observable 68 70 0 83 89 Expected - - - 68 70 R 15 19 EPHHL Observable 91 83 20 91 85 Expected - - - 93 86 R -2 -1 CIRAR Observable 25 20 18 63 83 Expected - - - 38 34 R 24 49 IPOHE Observable 5 0 0 60 40 Expected - - - 5 0 R 55 40 AMARE Observable 80 85 5 94 94 Expected - - - 81 86 R 13 8 HELAN Observable 83 88 5 93 92 Expected - - - 83 88 R 9 3

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KCHSC Observable 63 65 40 73 78 Expected - - - 78 79 R -5 -2 TRZAS Observable 0 0 0 0 0 Expected - - - 0 0 R 0 0

g/ha=grams per hectare

VIOTR=J7o/a tricolor (tricolor violet) АВiТН=Л/шь/ои theophrasti (Theophrastus's rope) POLCO=Polygomim convolvulus (convolvulus) EPHHL=Euphorhia heterophyPa (spurge) CIRAR=C//'.s//// 77 arvense IPOHE=7pomoea hederacea AMARE=Amaranthus retroflexus HELNN=Helianthus annuus KCHSC=Xoc/wa scoparia

TRZAS=7/7//c7//7? aestivum (spring wheat)

Example 6.

Compositions containing Compound A and the herbicides PDS inhibitors diflufenican and flurtamone and the VLCFA synthesis inhibitor flufenacet were tested on unwanted vegetation species including VIOTR, Viola tricolor, ABUTH, Abutilon theophrasti, knotweed bindweed (POLCO, Polygonum convolvulus), variegated spurge (EPHHL, Euphorbia heterophylla), thistle (CIRAR, Cirsium arvense), morning glory (IPOHE, Ipomoea hederacea), amaranth (AMARE, Amaranthus retroflexus), common sunflower (HELAN, Helianthus annuus ) and kochia (KCHSC, Kochia scoparia), in order to determine the effectiveness of the compositions in relation to these types of unwanted vegetation. The compositions were also tested on spring wheat (TRZAS) and the phytotoxicity of the compositions to this crop was measured.

The results are summarized in table. 6 below.

Table 6

Herbicidal effects (% visible damage) of compound A, diflufenican, flurtamone and flurtamone on weeds and grain crops

Application rate (g/ha) Compound A 7.5 10 0 7.5 10 Diflufenican 0 0 58.3 58.3 58.3 Flurtamon 0 0 58.3 58.3 58.3 Flufenacet 0 0 58.3 58.3 58.3

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VIOTR Observable 3 3 20 25 28 Expected - - - 22 22 P 3 6 ABUTH Observable 40 48 0 68 53 Expected - - - 40 48 P 28 5 POLCO Observable 68 70 10 73 78 Expected - - - 71 73 R 2 5 EPHHL Observable 91 83 20 90 93 Expected - - - 93 86 R -3 7 CIRAR Observable 25 20 23 75 83 Expected - - - 42 38 R 33 45 IPOHE Observable 5 0 10 20 15 Expected - - - 15 10 R 6 5 AMARE Observable 80 85 5 90 90 Expected - - - 81 86 R 9 4 HELAN Observable 83 88 5 92 98 Expected - - - 83 88 R 8 9 KCHSC Observable 63 65 48 78 79 Expected - - - 80 82 R -3 -3 TRZAS Observable 0 0 15 20 0 Expected - - - 15 15 R 5 -15

g/ha=grams per hectare

VIOTR=I 7o/<7 tricolor (tricolor violet)

ABUTH=/47w//7o// theophrasti (Theophrastus's rope) 'POLCO=Polygonum convolvulus (convolvulus) PPHHL=Euphorbia heterophylla (spurge)

CTRAR=C//.s7>//77 arvense (field thistle)

IPOHE=7pomoecz hederacea (Ipomoea ivy)

AMARE=Amaranthus retroflexus (amaranth)

UELAN=Helianthus anmius (common sunflower)

KCHSC=/<oc/7/tf scoparia (kochia)

TRZ AS=7/7//c7//77 aestivum (spring wheat)

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Example 7.

Compositions containing Compound A, the PDS inhibitor herbicide diflufenican, and the ALS inhibitor herbicides iodosulfuron and mesosulfuron were tested on unwanted vegetation species including amaranth (AMARE, Amaranthus retroflexus), winter rapeseed (BRSNW, Brassica napus) , white pigweed (CHEAL, Chenopodium album L), thistle (CIRAR, Cirsium arvense), kochia (KCHSC, Kochia scoparia), chamomile (MATCH, Matricaria chamomilla), bindweed (POLCO, Polygonum convolvulus) and field mustard (SINAR , Sinapis arvensis), in order to determine the effectiveness of the compositions against these types of unwanted vegetation. The compositions were also tested on spring wheat (TRZAS) and spring barley (HORVS) and the phytotoxicity of the compositions to each crop was measured.

The results are summarized in table. 7 below. In the table, the application rate indicated as X+Y+Z indicates that the diflufenican application rate is X, the iodosulfuron application rate is Y, and the mesosulfuron application rate is Z.

Table 7

Herbicidal effects (% visible damage) of compound A and diflufenican + iodosulfuron + mesosulfuron against weeds and grain crops

Application rate (g/ha) Compound A 7.5 10 0 7.5 10 Diflufenican + Iodine osulfuron + Mesosu lfuron 0 0 150+2+1 0 150+2+ 10 150+2+1 0 AMARE Observable 70 90 98 100 100 Expected - - - 99 100 R 1 0 BRSNW Observable 63 68 95 98 99 Expected - - - 98 98

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P -1 0 CHEAL Observable 70 78 93 90 96 Expected - - - 98 98 P -8 -2 CIRAR Observable 18 thirty thirty 78 85 Expected - - - 42 51 P 35 34 KCHSC Observable 65 70 25 73 80 Expected - - - 74 78 R -1 3 MATCH Observable 18 thirty 80 88 88 Expected - - - 84 86 R 4 2 POLCO Observable 60 70 80 90 93 Expected - - - 92 94 R -2 -2 SINAR Observable 85 88 98 100 100 Expected - - - 100 100 R 0 0 HORVS Observable 0 0 35 43 50 Expected - - - 35 35 R 8 15 TRZAS Observable 0 0 0 0 0 Expected - - - 0 0 R 0 0

g/ha=grams per hectare

AK\APE=Amaraiilhus retroflexus (amaranth) BRSNW=7f/z7s.s7cz/ napus (winter rapeseed) C]AENL=Chenopodium album L. (white pigweed) C.AP\R=Cirsium arvense (field thistle) KCHSC=Kochia scoparia (kohia)

MATSN=L /b///7С7//7b/ chamomilla (chamomile) VOLCQ=Polygonum convolvulus (convolvulus knotweed) STNAR=Sinapis arvensis (field mustard) AQRNS=Hordeum vulgare (spring barley) TRZAS=7/7//c7 //7? aestivum (spring wheat)

Example 8.

Compositions containing Compound A, PDS inhibitor herbicide, diflu phenican, ALS inhibitor herbicides, iodosulfuron and mesosulfuron were tested on unwanted vegetation species including amaranth (AMARE, Amaranthus retroflexus), winter rapeseed (BRSNW, Brassica napus) , white pigweed (CHEAL, Chenopodium album L), kochia (KCHSC, Kochia scoparia), chamomile (MATCH, Matricaria chamomilld), bindweed (POLCO, Poly

- 35 046295 gonum convolvulus) and Russian solyanka (SASKR, Salsola kali), in order to determine the effectiveness of the compositions against these types of unwanted vegetation. The compositions were also tested on spring wheat (TRZAS) and spring barley (HORVS) and the phytotoxicity of the compositions to each crop was measured.

The results are summarized in table. 8 below. In the table, the application rate indicated as X+Y+Z indicates that the diflufenican application rate is X, the iodosulfuron application rate is Y, and the mesosulfuron application rate is Z.

Table 8

Herbicidal effects (% visible damage) of compound A and diflufenican + iodosulfuron + mesosulfuron against weeds and grain crops

Application rate (g/ha) Compound A 7.5 10 15 0 0 7.5 10 15 7.5 10 15 Diflufenican+ Iodosulfuron+ Mesosulfuron 0 0 0 37.5+1, 875+5.6 25 75+3.75 +11.25 37.5+1, 875+5.6 25 37.5+1, 875+5.6 25 37.5+1.8 75+5.62 5 75+3.75 +11.25 75+3.75 +11.25 75+3.75 +11.25 AMARE Observable 78 78 83 38 60 70 80 75 73 70 73 Expected - - - - - 86 86 89 91 91 93 R -16 -6 -14 -19 -21 -21 BRSNW Observable 60 60 75 99 100 99 99 99 99 99 100 Expected - - - - - 99 99 100 100 100 100 R -1 -1 -1 -1 -1 0 CHEAL Observable 70 78 83 45 70 85 85 75 78 83 83 Expected - - - - - 84 88 90 91 93 95 R 2 -3 -15 -14 -AND -12 KCHSC Observable 70 70 70 15 thirty 80 85 83 73 80 78 Expected - - - - - 75 75 75 79 79 79 R 6 AND 8 -7 1 -2 MATCH Observable 8 15 10 45 83 68 75 73 70 75 80

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Expected - - - - - 49 53 51 84 85 84 R 18 22 22 -14 -10 -4 POLCO Observable 63 60 63 43 73 73 70 73 73 70 68 Expected - - - - - 78 77 78 90 89 90 R -6 -7 -6 -17 -19 -22 SASKR Observable 55 58 65 68 75 73 83 75 83 90 94 Expected - - - - - 85 86 89 89 89 91 R -13 -4 -14 -6 1 2 HORVS Observable 8 5 3 18 35 23 25 28 25 38 thirty Expected - - - - - 24 22 20 40 38 37 R -1 3 8 -15 -1 -7 TRZAS Observable 3 3 0 5 3 5 5 5 3 5 5 Expected - - - - - 7 7 5 5 5 3 R -2 -2 0 -2 0 3

g/ha= grams per hectare

AMARE=4zw«raz7//zzz5 retroflexus (amaranth)

BRSNW=/^m.s7czz napus (winter rapeseed)

CHEAL=Chenopodium album L. (white pigweed)

KCHSC=Kochia scoparia (kochia)

MATSN=L/0///7S'b//7b/ chamomilla (chamomile)

POLCO=Polygonum convolvulus (convolvulus knotweed)

SASKR=Ag/.vo/g kali (Russian solyanka)

HOPNS>=Hordeum vulgare (spring barley)

TRZAS=7rz7zczzzw aestivum (spring wheat)

The compositions and methods according to the appended claims are not limited in scope to the specific compositions and methods described herein, which are intended to be illustrative of several aspects of the claims, and it is intended that any compositions and methods that are functionally equivalent are found within the scope of the claims. Various modifications of the compositions and methods, in addition to those set forth and described herein, are intended to be within the scope of the appended claims. In addition, although only certain exemplary compositions and method steps disclosed herein are described in detail, it is intended that other combinations of compositions and method steps also fall within the scope of the appended claims even if not specifically set forth. Thus, a combination of steps, elements, components or constituents may be explicitly mentioned herein; however, other combinations of steps, elements, components and ingredients are included even if not expressly stated. The expression containing and its variants, when used herein, are used synonymously with the expression including and its variants, and they are open-ended, non-limiting expressions. Although the terms comprising and including are used herein to describe various aspects, the terms essentially consisting of and consisting of may be used instead of containing and including to provide more specific aspects and are also disclosed. Except in the examples and where otherwise indicated, all numbers which express amounts of ingredients, reaction conditions, etc., used in the specification and claims are to be construed with regard to the number of significant figures and customary rounding techniques, and should not be construed as an attempt to limit the application of the basic provisions of equivalents to the scope of the claims.

Claims (17)

CLAIM 1. Herbicidal composition containing: (a) a pyridine carboxylate herbicide represented by formula (I) NHR ² formula (I) wherein R ¹ represents cyanomethyl or propargyl; R ² and R ² represent hydrogen; R ^{3 4 5 6 7 8} , R ³ , R ³ and R ³ are hydrogen; or an agriculturally acceptable salt thereof, and (b) a PDS inhibitor herbicide or an agriculturally acceptable salt or ester thereof; where the weight ratio of the herbicide based on pyridine carboxylate (in g eq./ha) and the herbicide, which is a PDS inhibitor (in g a. i./ha), ranges from 1:2000 to 12:1. 2. The composition according to claim 1, where the pyridine carboxylate-based herbicidal compound is cyanomethyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate 3. The composition according to claim 1, where the pyridine carboxylate-based herbicidal compound is propargyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-III-indol-6-yl)pyridine-2-carboxylate 4. The composition according to any one of claims 1 to 3, wherein the PDS inhibitor herbicide is selected from the group consisting of beflubutamide, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, agriculturally acceptable salts thereof, or esters and combinations thereof. 5. The composition according to any one of claims 1 to 4, where the weight ratio of the herbicide based on pyridine carboxylate (in g eq./ha) and the herbicide representing a PDS inhibitor (in g a.i./ha) is from 1:1000 to 5:1. 6. Composition according to any one of claims 1-5, additionally containing an antidote. 7. The composition according to any one of claims 1 to 6, further comprising an additional pesticide selected from the group consisting of flufenacet, iodosulfuron, mesosulfuron, an agriculturally acceptable salt or ester thereof, and combinations thereof. 8. The composition according to any one of claims 1 to 6, wherein the composition does not contain a herbicidal active ingredient in addition to (a) and (b). - 38 046295 9. A method of controlling unwanted vegetation, comprising applying to vegetation or an area adjacent to vegetation, or applying to soil or water to limit the emergence or growth of vegetation, a composition containing: (a) a pyridine carboxylate herbicide defined by formula (I) NHR ² formula (I) wherein R ¹ represents cyanomethyl or propargyl; R ² and R ² represent hydrogen; R ³ , R ³ , R ³ and R ³ represent hydrogen; or an agriculturally acceptable salt thereof, and (b) a PDS inhibitor herbicide, or an agriculturally acceptable salt or ester thereof, wherein the pyridine carboxylate herbicide is used in an amount of at least 0.1 g eq. k./ha, and the PDS inhibitor herbicide is applied in an amount of at least 12.5 g a. i./ha, and the weight ratio of the pyridine carboxylate-based herbicide (in g eq./ha) and the PDS inhibitor herbicide (in g a. i./ha) ranges from 1:2000 to 12:1. 10. The method according to claim 9, wherein the pyridine carboxylate-based herbicidal compound is cyanomethyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate 11. The method according to claim 9, where the pyridine carboxylate-based herbicidal compound is propargyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-III-indol-6-yl)pyridine-2-carboxylate 12. The method according to any one of claims 9 to 11, wherein the PDS inhibitor herbicide is selected from the group consisting of beflubutamide, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, their agriculturally acceptable salts and esters and their combinations. 13. The method according to any one of claims 9-12, where the weight ratio of the herbicide based on pyridine carboxylate (in g eq./ha) and the herbicide representing a PDS inhibitor (in g a.i./ha) is from approximately 1:1000 to 5:1. 14. The method according to any one of claims 9 to 13, wherein the pyridine carboxylate herbicide and the PDS inhibitor herbicide are applied simultaneously. 15. The method according to any one of claims 9-14, where the composition additionally contains an antidote. 16. The method according to any one of claims 10 to 15, wherein the composition further comprises an additional pesticide selected from the group consisting of flufenacet, iodosulfuron, mesosulfuron, an agriculturally acceptable salt or ester thereof, and combinations thereof. 17. The method according to any one of claims 9 to 15, wherein the composition does not contain a herbicidal active ingredient in addition to (a) and (b).