EA046289B1 - COMPOSITIONS CONTAINING HERBICIDES BASED ON PYRIDINE CARBOXYLATE AND HERBICIDES REPRESENTING INHIBITORS OF FATTY ACIDS AND LIPIDS SYNTHESIS - Google Patents

Description

Technical field of the invention

The invention includes compositions containing (a) a pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt or ester thereof and (b) a fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide or its agriculturally acceptable salt or ester. 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 may, 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 suppressing 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 thereof and (b) a fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide, an agriculturally acceptable salt or ester thereof or mixtures thereof. The weight ratio of (a) and (b) may be from 1:250 to 1:5, from 1:150 to 1:112, from 1:20 to 1:25, from 1:8 to 1:2 or from 1 :7 to 1:1).

In some aspects, the composition contains (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 represent hydrogen;

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

or an agriculturally acceptable salt thereof, and (b) a fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide, an agriculturally acceptable salt or ester thereof, or mixtures thereof, and wherein the weight ratio (a) (in g eq. k./ha) and (b) (in g a. i./ha) is from 1: 250 to 1:5.

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 salt thereof, and (b) a fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide, an agriculturally acceptable salt or ester thereof, or mixtures thereof.

In some aspects, the composition contains:

(a) propargyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-III-indol-6-yl)pyridin-2-carboxylate, herbicide

- 1046289 pyridine carboxylate compound, hereinafter referred to as Compound B:

compound B, or an agriculturally acceptable salt thereof, and (b) a fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide, an agriculturally acceptable salt or ester thereof, or mixtures thereof.

In some aspects, (b) the FA/LSI herbicide may be selected from the group consisting of benfuresate, bensulide, butylate, cycloate, dalapone, EPTC (S-ethyldipropylthiocarbamate), esprocarb, ethophumesate, flupropanate, molinate, orbenecarb, prosulfocarb , thiobencarb, thiocarbazyl, triallate, vernolate, agriculturally acceptable salts or esters thereof and mixtures thereof.

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, to an area adjacent to vegetation, or to soil or water to control the emergence or growth of vegetation, a composition containing (a) a herbicide on pyridine carboxylate base or an agriculturally acceptable N-oxide, salt or ester thereof and (b) a fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide, an agriculturally acceptable salt or ester thereof or mixtures of them. 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, (a) the pyridine carboxylate herbicide can be applied in an amount from 0.5 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 cases, (b) the FA/LSI herbicide can be applied in quantities as low as 300 g a. i./ha up to 7500 g a. i./ha (for example, from 650 to 2500 g a.i./ha, from 375 to 6500 g a.i./ha, from 1500 to 5000 g a.i./ha, from 450 to 3200 g a.i./ha. i./ha or from 900 to 7000 g a.i./ha). In some cases, (a) and (b) may be used in a weight ratio of 1:250 to 1:5, 1:150 to 1:112, 1:20 to 1:25, 1:8 to 1 :2 or from 1:7 to 1:1).

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 fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide and an agriculturally acceptable salt thereof or ester, or mixtures thereof, where the weight ratio of (a) (in g eq./ha) and (b) (in g a.i./ha) is from 1: 250 to 1:5.

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 used in this document

- 2 046289 include references to the plural unless the context clearly indicates otherwise. 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 to the site 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, cover, pasture, erosion control, etc. Example crops include cereals, legumes, vegetables, turf, meadows, fruit plants and logs, cultivated grape species, 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 daltons and the salt form of Z has a molecular weight of 130 daltons, 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.

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 (for example, C1- _C6 -alkyl), haloalkyl (for example, C1- _C6 -haloalkyl), alkenyl (for example, _C2 - _C6 -alkenyl), haloalkenyl (for example, _C2 -C ₆ haloalkenyl), alkynyl (for example, C ₂ -C ₆ -alkynyl), aryl or heteroaryl, or arylalkyl (for example, C7C1 ₀ arylalkyl).

As used herein, the term alkyl may include straight chain

- 3 046289 point, branched or cyclic saturated hydrocarbon fragments. Unless otherwise indicated, C1- _C20 alkyl groups are meant (for example, Ο ₁ -Ο ₁₂ , C ₁ -C ₁₀ , Ο ₁ -Ο ₈ , Ο ₁ -Ο ₆ or Ο ₁ -Ο ₄ ). 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, C1- _C6 alkoxy, _C1 - _C6 haloalkoxy, _C1 - _C6 acyl, C1- _C6 alkylthio, C1- _C6 haloalkylthio _{. ​ ​ ​} C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, aminocarbonyl, _C1 - _C6 -alkylaminocarbonyl, haloalkylaminocarbonyl, _C1 - _C6- dialkylaminocarbonyl and _C1 - _C6 dihaloalkylaminocarbonyl, provided that the substituents are sterically compatible and the rules are satisfied chemical binding and deformation energy. Preferred substituents include cyano and C ₁ -C ₆ -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, 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 -C ₆ -halocarbamoyl, hydroxycarbonyl, C 1 -C _{6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl , aminocarbonyl} , C ₁ -C ₆ -alkylamino carbonyl, haloalkylaminocarbonyl, C1 -C6-dialkylaminocarbonyl and C1-C6-dihaloalkylaminocarbonyl, provided that the substituents are sterically compatible and the rules of chemical bonding and strain energy are satisfied. Preferred substituents include cyano and C1C6-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 where R is a C ₁ -C ₂₀ alkyl group (for example, C 1 -C ₁₂ , C 1 -C 10 , C ₁ -C ₈ , C ₁ -C ₆ or C ₁ -C ₄ ). 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 indicated, alkoxycarbonyl groups are meant, where R represents a C1- _C20 alkyl group (for example, _C1 - _C12 , C1- _C10 , _C1 - _C8 , _C1 - _C6 or _C1 -C ₄ ). Examples include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1methylpropoxycarbonyl, 2-methylpropoxycarbonyl, 1,1-dimethylethoxycarbonyl, pentoxycarbonyl, 1methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl bo nyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl , 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpenthoxycarbonyl, 1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-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 C1- _C20 alkyl group, (for example, _C1 - _C12 , C1- _C10 , _C1 - _C8 , _C1 - _C6 or _C1 -C ₄ ). Examples include chlorine

- 4 046289 methoxy, 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 C ₆ -C ₁₀ 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, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₁ - C ₆ -haloalkyl, C ₁ -C ₆ -haloalkoxy, C ₁ -C ₆ -acyl, C ₁ -C ₆ -alkylthio, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₆ -alkoxycarbonyl, C ₁ -C ₆ carbamoyl, hydroxycarbonyl, C ₁ -C ₆ -alkylcarbonyl, aminocarbonyl, C ₁ -C ₆ -alkylaminocarbonyl, C ₁ -C ₆ -dialkylaminocarbonyl, provided that the substituents are sterically compatible and the rules of chemistry are satisfied binding and deformation energy. 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 ' represent hydrogen;

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

or an agriculturally acceptable salt thereof, and (b) a fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide, an agriculturally acceptable salt or ester thereof, or mixtures thereof, and wherein the weight ratio (a) (in g eq. k./ha) and (b) (in g a. i./ha) is from 1: 250 to 1:5.

In some aspects, the compositions and methods of the present invention include a composition comprising (a) a pyridine carboxylate herbicide being cyanomethyl-4-amino3-chloro-5-fluoro-6-(7-fluoro-III-indol-6-yl) pyridine-2-carboxylate, compound A:

- 5 046289

compound A, or an agriculturally acceptable salt thereof; and (b) a fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide, an agriculturally acceptable salt or ester thereof, or mixtures thereof.

In some aspects, the compositions and methods of the present invention include a composition comprising (a) a pyridine carboxylate herbicide being propargyl-4-amino3-chloro-5-fluoro-6-(7-fluoro-III-indol-6-yl) pyridine-2-carboxylate, compound B:

NH ₂

Compound B, or an agriculturally acceptable salt thereof; and (b) a fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide, an agriculturally acceptable salt or ester thereof, or mixtures 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 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.

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 alkyl ammonium salts such as methyl ammonium, dimethyl ammonium, 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)ammonium salts, 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, R 9 - R ¹² ) may independently represent hydrogen, C ₁ -C ₁₀ -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.

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.

- 6 046289

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 preceding values, such as 0.1300 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 fatty acid and lipid synthesis inhibitors (FA/LSI)

In addition to the pyridine carboxylate herbicide or an agriculturally acceptable N-oxide, salt or ester thereof, the compositions may include a fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide, an agriculturally acceptable salt thereof or ester or mixtures thereof. FA/LSI herbicides apparently interfere with the biosynthesis of fatty acids and lipids, thereby reducing the accumulation of wax in the cuticle, which leads to abnormal cell development or inhibition of cell division in seedlings. Examples of FA/LSI herbicides include benfuresate, bensulide, butylate, cycloate, dalapon, EPTC, esprocarb, etofumesate, flupropanate, molinate, orbencarb, prosulfocarb, thiobencarb, thiocarbazyl, triallate, vernolate.

In some aspects, the composition may include an FA/LSI herbicide selected from the group consisting of benfuresate, bensulide, butylate, cycloate, dalapone, EPTC, esprocarb, ethophumesate, flupropanate, molinate, orbencarb, prosulfocarb, thiobencarb, thiocarbazyl, triallate, vernolate, their agriculturally acceptable salts or esters and mixtures thereof.

FA/LSI herbicides can be applied to vegetation or

- 7 046289 area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in quantities sufficient to cause a herbicidal effect. In some aspects, the FA/LSI herbicide 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 300 g a. i./ha or more, such as 310 g a. i./ha or more, 320 g a. i./ha or more, 325 g a.

i./ha or more, 330 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, 370 g a. i./ha or more, 375 ha. i./ha or more, 380 g a. i./ha or more, 390 g a.

i./ha or more, 400 g a. i./ha or more, 410 ha. i./ha or more, 420 g a. i./ha or more, 425 g a.

i./ha or more, 430 g a. i./ha or more, 440 g a. i./ha or more, 450 g a. i./ha or more, 460 g a.

i./ha or more, 470 g a. i./ha or more, 475 g a. i./ha or more, 480 g a. i./ha or more, 490 g a.

i./ha or more, 500 g a. i./ha or more, 525 g a. i./ha or more, 550 g a. i./ha or more, 575 g a.

i./ha or more, 600 g a. i./ha or more, 625 g a. i./ha or more, 650 g a. i./ha or more, 675 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, 1100 g a.

i./ha or more, 1200 g a. i./ha or more, 1300 g a. i./ha or more, 1400 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, 2100 g a. i./ha or more, 2200 g a. i./ha or more, 2300 g a. i./ha or more, 2400 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, 2800 g a. i./ha or more, 2900 g a. i./ha or more, 3000 g a. i./ha or more, 3250 g a. i./ha or more, 3500 g a. i./ha or more, 3750 g a. i./ha or more, 4000 g a. i./ha or more, 4250 g a. i./ha or more, 4500 g a. i./ha or more, 4750 g a. i./ha or more, 5000 g a. i./ha or more, 5250 g a. i./ha or more, 5500 g a. i./ha or more, 5750 g a. i./ha or more, 5000 g a. i./ha or more, 5250 g a. i./ha or more, 5500 g a. i./ha or more, 5750 g a. i./ha or more, 6000 g a. i./ha or more, 6250 g a. i./ha or more, 6500 g a. i./ha or more, 6750 g a. i./ha or more, 7000 g a. i./ha or more, 7250 g a. i./ha or more, 7500 g a. i./ha or more, 7750 g a. i./ha or more, 8000 g a. i./ha or more, 8250 g a. i./ha or more, 8500 g a. i./ha or more, 8750 g a. i./ha or more, 9000 g a. i./ha or more, 9250 g a. i./ha or more, 9500 g a. i./ha or more, 9750 g a. i./ha or more, 10 kg a. i./ha or more, 10.5 kg a. i./ha or more, 11 kg a. i./ha or more, 11.5 kg a. i./ha or more, 12 kg a. i./ha or more, 12.5 kg a. i./ha or more, 13 kg a. i./ha or more, 13.5 kg a. i./ha or more, 14 kg a. i./ha or more, 14.5 kg a. i./ha or more, 15 kg a. i./ha or more, 15.5 kg a. i./ha or more, 16 kg a. i./ha or more, 16.5 kg a. i./ha or more, 16.75 kg a. i./ha or more, 17 kg a. i./ha or more, 17.5 kg a. i./ha or more, 18 kg a. i./ha or more, 18.5 kg a. i./ha or more, 19 kg a. i./ha or more, 19.5 kg a. i./ha or more, 20 kg a. i./ha or more or 20.5 kg a. i./ha or more; in the amount of 21 kg a. i./ha or less, such as 20.5 kg a. i./ha or less, 20 kg a. i./ha or less, 19.5 kg a. i./ha or less, 19 kg a. i./ha or less, 18.5 kg a. i./ha or less, 18 kg a. i./ha or less, 17.5 kg a. i./ha or less, 17 kg a. i./ha or less, 16.5 kg a. i./ha or less, 16 kg a. i./ha or less, 15.5 kg a. i./ha or less, 15 kg a. i./ha or less, 14.5 kg a. i./ha or less, 14 kg a. i./ha or less, 13.5 kg a. i./ha or less, 13 kg a. i./ha or less, 12.5 kg a. i./ha or less, 12 kg a. i./ha or less, 11.5 kg a. i./ha or less, 11 kg a. i./ha or less, 10.5 kg a. i./ha, 10 kg a. i./ha or less, 9750 g a. i./ha or less, 9500 g a. i./ha or less, 9250 g a. i./ha or less, 9000 g a. i./ha or less, 8750 g a. i./ha or less, 8500 g a. i./ha or less, 8250 g a. i./ha or less, 8000 g a. i./ha or less, 7750 g a. i./ha or less, 7500 g a. i./ha or less, 7250 g a. i./ha or less, 7000 g a. i./ha or less, 6750 g a. i./ha or less, 6500 g a. i./ha or less, 6250 g a. i./ha or less, 6000 g a. i./ha or less, 6750 g a. i./ha or less, 6500 g a. i./ha or less, 5250 g a. i./ha or less, 5000 g a. i./ha or less, 4750 g a. i./ha or less, 4500 g a. i./ha or less, 4250 g a. i./ha or less, 4000 g a. i./ha or less, 3750 g a. i./ha or less, 3500 g a. i./ha or less, 3250 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, 2700 g a. i./ha or less, 2600 g a. i./ha or less, 2500 g a. i./ha or less, 2400 g a. i./ha or less, 2300 g a. i./ha or less, 2200 g a. i./ha or less, 2100 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, 1700 g a. i./ha or less, 1600 g a. i./ha or less, 1500 g a. i./ha or less, 1400 g a. i./ha or less, 1300 g a. i./ha or less, 1200 g a. i./ha or less, 1100 g a. i./ha or less, 1000 g a. i./ha or less, 950 g a. i./ha or less, 900 g a.

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

i./ha or i./ha or i./ha or less, less, less, less, less, less, less, less,

850

675

575

490

460

425

390

360 g y y y y y

A. A. A. A. A. A. A. A.

i./ha or less, 800

i./ha or less, 650

i./ha or less, 550

i./ha or less, 480

i./ha i./ha i./ha i./ha y y y or less, 450 or less, 420 or less, 380 or less, 350

A. i./ha or less, 750

A. i./ha or less, 625

A. i./ha or less, 525

A. i./ha or less, 475 g g g g

A.

A.

A.

A.

and./ha and./ha and./ha and./ha or or or less, less, less, less,

700

600

500

470 g g g g

A.

A.

A.

A.

g a. i./ha or less, 440 g a. i./ha or less, 430 ha. g a. i./ha or less, 410 g a. i./ha or less, 400 g a. g a. i./ha or less, 375 g a. i./ha or less, 370 g a. g a. i./ha or less, 340 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 or 310 g a. i./ha or less; or in

- 8 046289 an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 300 g - 21 kg a. i./ha, 950-4500 g a. i./ha, 4603750 g a. i./ha, 6-15 kg a. i./ha, 900-1700 g a. i./ha, 320-450 g a. i./ha, 8500 g - 14 kg a. i./ha, 750-2200 g a. i./ha, 390-5250 g a. i./ha, 400-1200 g a. i./ha, 1200-3500 g a. i./ha or 310 g - 20.5 kg a. i./ha.

Benfuresat

In some aspects, the FA/LSI herbicide may comprise benfuresate or an agriculturally acceptable salt or ester thereof. Benfuresat, shown below, is a benzofuran-based herbicide used for post-emergence control of grass and broadleaf weeds in paddy, fruit crops, beans, maize, sugar cane and perennial crops at 450-600 g/ha and for control by pre-sowing seeding in cotton and tobacco in the amount of 2000-3000 g/ha. Benfuresate, as well as methods for producing benfuresate, are known from the prior art. Its herbicidal activity is described, for example, in Tomlin, C. DS, 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).

Benfuresat 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, benfuresat 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 150 g a. i./ha or more, such as 160 g a. i./ha or more, 170 g a. i./ha or more, 175 ha. 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, 210 ha. i./ha or more, 220 g a. i./ha or more, 225 g a. i./ha or more, 230 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, 270 g a.

i./ha or more, 275 g a. i./ha or more, 280 g a. i./ha or more, 290 g a. i./ha or more, 300 g a.

i./ha or more, 310 g a. i./ha or more, 320 g a. i./ha or more, 325 g a. i./ha or more, 330 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, 370 g a.

i./ha or more, 375 ha. i./ha or more, 380 g a. i./ha or more, 390 ha. i./ha or more, 400 g a. i./ha or more, 410 ha. i./ha or more, 420 g a. i./ha or more, 425 g a. i./ha or more, 430 g a. i./ha or more, 440 g a. i./ha or more, 450 g a. i./ha or more, 460 g a. i./ha or more, 470 g a.

i./ha or more, 475 g a. i./ha or more, 480 g a. i./ha or more, 490 g a. i./ha or more, 500 g a.

i./ha or more, 525 g a. i./ha or more, 550 g a. i./ha or more, 575 g a. i./ha or more, 600 g a.

i./ha or more, 625 g a. i./ha or more, 650 g a. i./ha or more, 675 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, 1750 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, 2100 g a. i./ha or more, 2200 g a. i./ha or more, 2300 g a. i./ha or more, 2400 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, 2800 g a. i./ha or more or 2900 g a. i./ha or more; in the amount of 3000 g a. i./ha or less, such as 2900 g a. i./ha or less, 2800 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, 2400 g a. i./ha or less, 2300 g a. i./ha or less, 2200 g a. i./ha or less, 2100 ha. 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, 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, 675 g a. i./ha or less, 650 g a. i./ha or less, 625 g a. i./ha or less, 600 g a. i./ha or less, 575 g a. i./ha or less, 550 g a. i./ha or less, 525 g a. i./ha or less, 500 g a. i./ha or less, 490 g a. i./ha or less, 480 g a. i./ha or less, 475 g a. i./ha or less, 470 g a. i./ha or less, 460 g a. i./ha or less, 450 g a. i./ha or less, 440 g a. i./ha or less, 430 g a. i./ha or less, 425 g a. i./ha or less, 420 g a. i./ha or less, 410 ha. i./ha or less, 400 g a. i./ha or less, 390 g a.

i./ha or less, 380 g a. i./ha or less, 375 ha. i./ha or less, 370 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, 330 g a. i./ha or less, 325 g a.

i./ha or less, 320 g a. i./ha or less, 310 ha. i./ha or less, 300 g a. i./ha or less, 290 g a.

- 9 046289

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, 250 g a. i./ha or less, 240 g a. i./ha or less, 230 g a. i./ha or less, 225 g a. i./ha or less, 220 g a. i./ha or less, 210 ha. i./ha or less, 200 g a. i./ha or less, 190 ha. i./ha or less, 180 g a. i./ha or less, 175 ha. i./ha or less, 170 g a. i./ha or less or 160 ha. 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 150-3000 g a. i./ha, 950-2800 g a. i./ha, 575-850 g a. i./ha, 250-2500 g a. i./ha, 1350-2700 g a. i./ha, 1150-2300 g a. i./ha, 19002600 g a. i./ha, 270-1200 g a. i./ha, 480-5250 g a. i./ha, 500-1400 g a. i./ha, 440-1700 g a. i./ha or 160-2900 g a. i./ha.

Bensulide

In some aspects, the FA/LSI herbicide may comprise a bensulide or an agriculturally acceptable salt or ester thereof. Bensulide shown below is a phosphorodithioate herbicide used for pre-emergence control of broadleaf weeds in Brassica plants, squash species, lettuce, onion species, etc. at 5600-6700 g/ha and in established grass turf in the amount of 8400-28000 g/ha per season. Bensulide, as well as methods for producing bensulide, are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

CH ₃

Bensulide 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, bensulide 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 5000 g a. i./ha or more, such as 5250 g a. i./ha or more, 5500 g a. i./ha or more, 5750 g a. i./ha or more, 6000 g a. i./ha or more, 6250 g a. i./ha or more, 6500 g a. i./ha or more, 6750 g a. i./ha or more, 7000 g a. i./ha or more, 7250 g a. i./ha or more, 7500 g a. i./ha or more, 7750 g a. i./ha or more, 8000 g a. i./ha or more, 8250 g a. i./ha or more, 8500 g a. i./ha or more, 8750 g a. i./ha or more, 9000 g a. i./ha or more, 9250 g a. i./ha or more, 9500 g a. i./ha or more, 9750 g a. i./ha or more, 10 kg a. i./ha or more, 10.5 kg a. i./ha or more, 11 kg a. i./ha or more, 11.5 kg a. i./ha or more, 12 kg a. i./ha or more, 12.5 kg a. i./ha or more, 13 kg a. i./ha or more or 13.5 kg a. i./ha or more; in the amount of 14 kg a. i./ha or less, such as 13.5 kg a. i./ha or less, 13 kg a. i./ha or less, 12.5 kg a. i./ha or less, 12 kg a. i./ha or less, 11.5 kg a. i./ha or less, 11 kg a. i./ha or less, 10.5 kg a. i./ha, 10 kg a. i./ha or less, 9750 g a. i./ha or less, 9500 g a. i./ha or less, 9250 g a. i./ha or less, 9000 g a. i./ha or less, 8750 g a. i./ha or less, 8500 g a. i./ha or less, 8250 g a. i./ha or less, 8000 g a. i./ha or less, 7750 g a. i./ha or less, 7500 g a. i./ha or less, 7250 g a. i./ha or less, 7000 g a. i./ha or less, 6750 g a. i./ha or less, 6500 g a. i./ha or less, 6250 g a. i./ha or less, 6000 g a. i./ha or less, 5750 g a. i./ha or less, 5500 g a. i./ha or less or 5250 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 5-15 kg a. i./ha, 9500 g - 13 kg a. i./ha, 6250-8750 g a. i./ha, 7-12 kg a. i./ha, 8500-9750 g a. i./ha, 11-13.5 kg a. i./ha, 5750-7750 g a. i./ha, 9750 g - 12 kg a. i./ha, 10-11 kg a. i./ha, 7500-9500 g a. i./ha or 5250 g -13.5 kg a. i./ha.

Butylate

In some aspects, the FA/LSI herbicide may comprise butylate or an agriculturally acceptable salt or ester thereof. Butylate, shown below, is a thiocarbamate herbicide used for pre-plant control of annual grass weeds and Cyperus spp. in maize and pineapple species in an amount of 3000-4000 g/ha. Butylate, as well as methods for producing butylate, are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

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CH ₃ k^CH ₃ CH ₃

The butylate 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 cause a herbicidal effect. In neko

- 10 046289 In other aspects, butylate 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 3000 g a. i./ha or more, such as 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, 3750 g a. i./ha or more, 4000 g a. i./ha or more, 4250 g a. i./ha or more, 4500 g a. i./ha or more, 4750 g a. i./ha or more, 5000 g a. i./ha or more, 5250 g a. i./ha or more, 5500 g a. i./ha or more, 5750 g a. i./ha or more, 6000 g a. i./ha or more, 6250 g a. i./ha or more, 6500 g a. i./ha or more or 6750 g a. i./ha or more; in the amount of 7000 g a. i./ha or less, such as 6750 g a. i./ha or less, 6500 g a. i./ha or less, 6250 g a. i./ha or less, 6000 g a. i./ha or less, 5750 g a. i./ha or less, 5500 g a. i./ha or less, 5250 g a. i./ha or less, 5000 g a. i./ha or less, 4750 g a. i./ha or less, 4500 g a. i./ha or less, 4250 g a. i./ha or less, 4000 g a. i./ha or less, 3750 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 or 3100 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 30,007,000 g a. i./ha, 4500-6500 g a. i./ha, 3100-3750 g a. i./ha, 6000-7000 g a. i./ha, 3750-5500 g a. i./ha, 3300-4250 g a. i./ha, 5000-6000 g a. i./ha, 4250-5750 g a. i./ha, 3250-5250 g a. i./ha, 3500-4000 g a. i./ha or 3100-6750 g a. i./ha.

Cycloate

In some aspects, the FA/LSI herbicide may comprise a cycloate or an agriculturally acceptable salt or ester thereof. Cycloate, shown below, is a thiocarbamate herbicide used for seedbed control of annual and some perennial grass weeds, Cyperus spp. and some annual broadleaf weeds in sugar beets, fodder beets, beets and spinach in an amount of 3000-4000 g/ha. The cycloate, as well as methods for producing cycloate, are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

ABOUT

The cycloate 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, the cycloate 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 2500 g a. i./ha or more, such as 2600 g a. i./ha or more, 2700 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, 3750 g a. i./ha or more, 4000 g a. i./ha or more or 4250 g a. i./ha or more; in the amount of 4500 g a. i./ha or less, such as 4250 g a. i./ha or less, 4000 g a. i./ha or less, 3750 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, 2700 g a. i./ha or less or 2600 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 2500-4500 g a. i./ha, 3200-4000 g a. i./ha, 2800-3750 g a. i./ha, 3600-4250 g a. i./ha, 3750-4250 g a. i./ha, 2900-4000 g a. i./ha, 3250-4500 g a. i./ha, 3100-4000 g a. i./ha, 2500-3400 g a. i./ha or 2600-4250 g a. i./ha.

Dalapon

In some aspects, the FA/LSI herbicide may comprise dalapon or an agriculturally acceptable salt or ester thereof. Dalapone, shown below, is a thiocarbamate herbicide used for pre- and post-emergence control of annual and perennial grass weeds on land not used for agriculture, such as earthen embankments, roadsides, industrial sites, railroad tracks, irrigation canals, irrigation canals, etc., in pome fruit crop, stone fruit crop, fruit bush, citrus crop, nut species, olive species, grape species, woodland, banana species, sugar cane, rhubarb, asparagus, potato species, pea species , types of soybeans, types of beets, oilseed rape, flax, maize, sorghum, coffee, tea, ficus rubber, cotton and ornamental shrubs; for control of weeds of the genus Phragmites, sedges, weeds

- 11 046289 genus Juncus, halophytic and semi-aquatic grass weeds in watercourses. Typical agriculturally acceptable salts of dalapone include its magnesium and sodium salts. Dalapone, as well as methods for producing dalapon, are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

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Dalapon 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, dalapon 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 1500 g a. i./ha or more, such as 1600 g a. i./ha or more, 1700 g a. i./ha or more, 1750 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, 2100 g a. i./ha or more, 2200 g a. i./ha or more, 2300 g a. i./ha or more, 2400 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, 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, 3750 g a. i./ha or more, 4000 g a. i./ha or more, 4250 g a. i./ha or more, 4500 g a. i./ha or more, 4750 g a. i./ha or more, 5000 g a. i./ha or more, 5250 g a. i./ha or more, 5500 g a. i./ha or more, 5750 g a. i./ha or more, 6000 g a. i./ha or more, 6250 g a. i./ha or more, 6500 g a. i./ha or more, 6750 g a. i./ha or more, 7000 g a. i./ha or more, 7250 g a. i./ha or more, 7500 g a. i./ha or more, 7750 g a. i./ha or more, 8000 g a. i./ha or more, 8250 g a. i./ha or more, 8500 g a. i./ha or more, 8750 g a. i./ha or more, 9000 g a. i./ha or more, 9250 g a. i./ha or more, 9500 g a. i./ha or more, 9750 g a. i./ha or more, 10 kg a. i./ha or more, 10.5 kg a. i./ha or more, 11 kg a. i./ha or more, 11.5 kg a. i./ha or more, 12 kg a. i./ha or more, 12.5 kg a. i./ha or more, 13 kg a. i./ha or more, 13.5 kg a. i./ha or more, 14 kg a. i./ha or more, 14.5 kg a. i./ha or more, 15 kg a. i./ha or more, 15.5 kg a. i./ha or more, 16 kg a. i./ha or more, 16.5 kg a. i./ha or more, 16.75 kg a. i./ha or more, 17 kg a. i./ha or more,

17.5 kg a. i./ha or more, 18 kg a. i./ha or more, 18.5 kg a. i./ha or more, 19 kg a. i./ha or more, 19.5 kg a. i./ha or more, 20 kg a. i./ha or more or 20.5 kg a. i./ha or more; in the amount of 21 kg a. i./ha or less, such as 20.5 kg a. i./ha or less, 20 kg a. i./ha or less, 19.5 kg a. i./ha or less, 19 kg a. i./ha or less, 18.5 kg a. i./ha or less, 18 kg a. i./ha or less, 17.5 kg a. i./ha or less, 17 kg a. i./ha or less, 16.5 kg a. i./ha or less, 16 kg a. i./ha or less, 15.5 kg a. i./ha or less, 15 kg a. i./ha or less, 14.5 kg a. i./ha or less, 14 kg a. i./ha or less, 13.5 kg a. i./ha or less, 13 kg a. i./ha or less, 12.5 kg a. i./ha or less, 12 kg a. i./ha or less, 11.5 kg a. i./ha or less, 11 kg a. i./ha or less, 10.5 kg a. i./ha, 10 kg a. i./ha or less, 9750 g a. i./ha or less, 9500 g a. i./ha or less, 9250 g a. i./ha or less, 9000 g a. i./ha or less, 8750 g a. i./ha or less, 8500 g a. i./ha or less, 8250 g a. i./ha or less, 8000 g a. i./ha or less, 7750 g a. i./ha or less, 7500 g a. i./ha or less, 7250 g a. i./ha or less, 7000 g a. i./ha or less, 6750 g a. i./ha or less, 6500 g a. i./ha or less, 6250 g a. i./ha or less, 6000 g a. i./ha or less, 5750 g a. i./ha or less, 5500 g a. i./ha or less, 5250 g a. i./ha or less, 5000 g a. i./ha or less, 4750 g a. i./ha or less, 4500 g a. i./ha or less, 4250 g a. i./ha or less, 4000 g a. i./ha or less, 3750 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, 2700 g a. i./ha or less, 2600 g a. i./ha or less, 2500 g a. i./ha or less, 2400 g a. i./ha or less, 2300 g a. i./ha or less, 2200 g a. i./ha or less, 2100 ha. 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 or 1600 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 1500 g - 21 kg a. i./ha, 7250-8500 g a. i./ha, 14-20 kg a. i./ha, 6500-8250 g a. i./ha, 5-15 kg a. i./ha, 11-14.5 kg a. i./ha, 12.5-19 kg a. i./ha, 7500 g 17 kg a. i./ha, 1800-5250 g a. i./ha, 4500-8500 g a. i./ha, 6750-9750 g a. i./ha or 1600 g - 20.5 kg a. i./ha

ERTS

In some aspects, the FA/LSI herbicide may comprise S-ethyldipropylthiocarbamate, better known as EPTC, or an agriculturally acceptable salt or ester thereof. EPTC, shown below, is a thiocarbamate herbicide used for pre-plant control of annual and perennial grasses, particularly wheatgrass, sedges such as Cyperus spp., and some broadleaf weeds in potato species, bean species, pea species, forage crops, legumes, beets, types

- 12 046289 sugar beets, alfalfa, horned lambswort, clover, cotton, maize, flax, types of sweet potatoes, types of safflower, types of sunflowers, types of strawberries, citrus crops, types of almonds, types of walnuts, ornamental plants, types of pineapple and pine seedlings in in an amount of 4500-6700 g/ha and in maize with the antidote dichlormide. EPTC, as well as methods for producing EPTC, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

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CH ₃

EPTS 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, EPTC 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 1000 g a. i./ha or more, such as 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, 1750 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, 2100 g a. i./ha or more, 2200 g a. i./ha or more, 2300 g a. i./ha or more, 2400 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, 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, 3750 g a. i./ha or more, 4000 g a. i./ha or more, 4250 g a. i./ha or more, 4500 g a. i./ha or more, 4750 g a. i./ha or more, 5000 g a. i./ha or more, 5250 g a. i./ha or more, 5500 g a. i./ha or more, 5750 g a. i./ha or more, 6000 g a. i./ha or more, 6250 g a. i./ha or more, 6500 g a. i./ha or more, 6750 g a. i./ha or more, 7000 g a. i./ha or more, 7250 g a. i./ha or more, 7500 g a. i./ha or more, 7750 g a. i./ha or more, 8000 g a. i./ha or more, 8250 g a. i./ha or more, 8500 g a. i./ha or more or 8750 g a. i./ha or more; in the amount of 9000 g a. i./ha or less, such as 8750 g a. i./ha or less, 8500 g a. i./ha or less, 8250 g a. i./ha or less, 8000 g a. i./ha or less, 7750 g a. i./ha or less, 7500 g a. i./ha or less, 7250 g a. i./ha or less, 7000 g a. i./ha or less, 6750 g a. i./ha or less, 6500 g a. i./ha or less, 6250 g a. i./ha or less, 6000 g a. i./ha or less, 5750 g a. i./ha or less, 5500 g a. i./ha or less, 5250 g a. i./ha or less, 5000 g a. i./ha or less, 4750 g a. i./ha or less, 4500 g a. i./ha or less, 4250 g a. i./ha or less, 4000 g a. i./ha or less, 3750 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, 2700 g a. i./ha or less, 2600 g a. i./ha or less, 2500 g a. i./ha or less, 2400 g a. i./ha or less, 2300 g a. i./ha or less, 2200 g a. i./ha or less, 2100 ha. 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, 1200 g a. i./ha or less, 1150 g a. i./ha or less, 1100 g a. i./ha or less or 1050 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 1000-9000 g a. i./ha, 2200-6500 g a. i./ha, 1450-3750 g a. i./ha, 2600-7500 g a. i./ha, 1050-4000 g a. i./ha, 2100-4500 g a. i./ha, 1900-5500 g a. i./ha, 7250-8500 g a. i./ha, 3300-6250 g a. i./ha, 1500-3000 g a. i./ha, 2500-8250 g a. i./ha or 1050-8750 ha. i./ha.

Esprocarb

In some aspects, the FA/LSI herbicide may comprise esprocarb or an agriculturally acceptable salt or ester thereof. Esprocarb, shown below, is a thiocarbamate herbicide used for pre- and post-emergence control of annual weeds such as Echinochloa spp. in a rice field at 1500-4000 g/ha. Esprocarb, as well as methods for producing esprocarb, are known in the art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

ABOUT SN _E

Esprocarb 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, esprocarb 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 400 g a. i./ha or more, such as 410 hectares. i./ha or more, 420 g a. i./ha or more, 425 g a. i./ha or more, 430 g a. i./ha or more, 440 g a. i./ha or more,

450 g a. i./ha or more, 460 g a. i./ha or more, 470 g a. i./ha or more, 475 g a. i./ha or more,

480 g a. i./ha or more, 490 g a. i./ha or more, 500 g a. i./ha or more, 525 g a. i./ha or more,

550 g a. i./ha or more, 575 g a. i./ha or more, 600 g a. i./ha or more, 625 g a. i./ha or more,

650 g a. i./ha or more, 675 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, 1750 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, 2100 g a. i./ha or more, 2200 g a. i./ha or more, 2300 g a. i./ha or more, 2400 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, 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 or 3750 g a. i./ha or more; 4000 g a. i./ha or less, such as 3750 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, 2700 g a. i./ha or less, 2600 g a. i./ha or less, 2500 g a. i./ha or less, 2400 g a. i./ha or less, 2300 g a. i./ha or less, 2200 g a. i./ha or less, 2100 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, 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, 675 g a. i./ha or less, 650 g a.

i./ha or less, 625 g a. i./ha or less, 600 g a. i./ha or less, 575 g a. i./ha or less, 550 ha.

i./ha or less, 525 g a. i./ha or less, 500 g a. i./ha or less, 490 g a. i./ha or less, 480 ha.

i./ha or less, 475 g a. i./ha or less, 470 g a. i./ha or less, 460 g a. i./ha or less, 450 ha.

i./ha or less, 440 g a. i./ha or less, 430 ha. i./ha or less, 425 g a. i./ha or less, 420 g a. i./ha or less or 410 ha. 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 400-4000 g a. i./ha, 2500-3500 g a. i./ha, 600-2700 g a. i./ha, 3100-4000 g a. i./ha, 2000-3000 g a. i./ha, 1800-3250 g a. i./ha, 900-3400 g a. i./ha, 1750-2200 g a. i./ha, 2800-3750 g a. i./ha, 550-1900 g a. i./ha, 1700-3300 g a. i./ha or 410-3750 g a. i./ha.

Etofumesate

In some aspects, the FALSI herbicide may comprise an ethofumesate or an agriculturally acceptable salt or ester thereof. Ethofumesate, shown below, is a benzofuran-based herbicide used for pre- and post-emergence control of grass and broadleaf weeds in sugar beets, other beets, turf, ryegrass and other pasture grasses at 300-2000 g/ha. Ethofumesate, as well as methods for producing ethofumesate are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

Ethofumesate can be applied to vegetation or an area adjacent 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, ethofumesate 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 210 hectares. i./ha or more, 220 g a. i./ha or more, 225 g a. i./ha or more, 230 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, 270 g a. i./ha or more, 275 g a. i./ha or more, 280 g a. i./ha or more, 290 g a. i./ha or more, 300 g a. i./ha or more, 310 ha. i./ha or more, 320 g a. i./ha or more, 325 g a. i./ha or more, 330 g a. i./ha or more, 340 g a. i./ha or

- 14 046289 more, 350 g a. i./ha or more, 360 g a. i./ha or more, 370 g a. i./ha or more, 375 ha. i./ha or more, 380 g a. i./ha or more, 390 ha. i./ha or more, 400 g a. i./ha or more, 410 ha. i./ha or more, 420 g a. i./ha or more, 425 g a. i./ha or more, 430 g a. i./ha or more, 440 g a. i./ha or more, 450 g a. i./ha or more, 460 g a. i./ha or more, 470 g a. i./ha or more, 475 g a. i./ha or more, 480 g a. i./ha or more, 490 g a. i./ha or more, 500 g a. i./ha or more, 525 g a. i./ha or more, 550 g a. i./ha or more, 575 g a. i./ha or more, 600 g a. i./ha or more, 625 g a. i./ha or more, 650 g a. i./ha or more, 675 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, 1750 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, 2100 ha. i./ha or more, 2200 g a. i./ha or more, 2300 g a. i./ha or more, 2400 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, 2800 g a. i./ha or more or 2900 g a. i./ha or more; in the amount of 3000 g a. i./ha or less, such as 2900 g a. i./ha or less, 2800 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, 2400 g a. i./ha or less, 2300 g a. i./ha or less, 2200 g a. i./ha or less, 2100 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, 1200 g a. i./ha or less, 1150 g a. i./ha or less, 1100 ha. 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, 675 g a. i./ha or less, 650 g a. i./ha or less, 625 g a. i./ha or less, 600 g a. i./ha or less, 575 g a. i./ha or less, 550 g a. i./ha or less, 525 g a. i./ha or less, 500 g a. i./ha or less, 490 g a. i./ha or less, 480 g a. i./ha or less, 475 g a. i./ha or less, 470 g a. i./ha or less, 460 g a. i./ha or less, 450 g a. i./ha or less, 440 g a. i./ha or less, 430 g a. i./ha or less, 425 g a. i./ha or less, 420 g a. i./ha or less, 410 ha. i./ha or less, 400 g a. i./ha or less, 390 g a. i./ha or less, 380 g a. i./ha or less, 375 ha. i./ha or less, 370 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, 330 g a. i./ha or less, 325 g a. i./ha or less, 320 g a. i./ha or less, 310 g a. i./ha or less, 300 g a. i./ha or less, 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, 250 g a. i./ha or less, 240 g a. i./ha or less, 230 ha. i./ha or less, 225 g a. i./ha or less, 220 g a. i./ha or less or 210 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 200-3000 g a. i./ha, 950-2500 g a. i./ha, 460-1750 g a. i./ha, 600-2500 g a. i./ha, 350-2200 g a. i./ha, 310-450 g a. i./ha, 500-2400 g a. i./ha, 750-2200 g a. i./ha, 380-1350 g a. i./ha, 575-1300 g a. i./ha, 440-2600 g a. i./ha or 210-2900 g a. i./ha.

Flupropanate

In some aspects, the FA/LSI herbicide may comprise flupropanate or an agriculturally acceptable salt or ester thereof. Flupropanate, shown below, is a halogenated carboxylic acid herbicide used for post-emergence control of annual and perennial grass weeds, such as feather grass species Nassella trichotoma and feather grass species Nassella neesiana, in pastures and non-cropland. One agriculturally acceptable flupropanate salt is sodium flupropanate. Flupropanate, as well as methods for producing flupropanate are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

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Flupropanate 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, flupropanate 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 1000 g a. i./ha or more, such as 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, 1750

- 15 046289 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, 2100 g a. i./ha or more, 2200 g a. i./ha or more, 2300 g a. i./ha or more, 2400 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, 2800 g a. i./ha or more or 2900 g a. i./ha or more; in the amount of 3000 g a. i./ha or less, such as 2900 g a. i./ha or less, 2800 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, 2400 g a. i./ha or less, 2300 g a. i./ha or less, 2200 g a. i./ha or less, 2100 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, 1200 g a. i./ha or less, 1150 g a. i./ha or less, 1100 g a. i./ha or less or 1050 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 1000-3000 g a. i./ha, 1150-2500 g a. i./ha, 1400-1750 g a. i./ha, 1600-2500 g a. i./ha, 1050-2200 g a. i./ha, 1350-2400 g a. i./ha, 2500-2900 g a. i./ha, 1750-2700 g a. i./ha, 1300-1600 g a. i./ha, 1800-2300 g a. i./ha or 1050-2900 g a. i./ha.

Molinate

In some aspects, the FA/LSI herbicide may comprise molinate or an agriculturally acceptable salt or ester thereof. Molinate, shown below, is a thiocarbamate herbicide used to control germinating broadleaf and grass weeds, particularly Echinochloa spp. and Glyceria spp., in rice at a rate of 2500-5000 g/ha, applied either before planting for rice with seeds sown in water or rice with seeds sown in shallow soil or after flooding, in the post-emergence period for other types of rice crops. Molinate, as well as methods for producing molinate, are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

The molinate 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 cause a herbicidal effect. In some aspects, the molinate 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 2500 g a. i./ha or more, such as 2600 g a. i./ha or more, 2700 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, 3750 g a. i./ha or more, 4000 g a. i./ha or more, 4250 g a. i./ha or more, 4500 g a. i./ha or more or 4750 g a. i./ha or more; in the amount of 5000 g a. i./ha or less, such as 4750 g a. i./ha or less, 4500 g a. i./ha or less, 4250 g a. i./ha or less, 4000 g a. i./ha or less, 3750 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, 2700 g a. i./ha or less or 2600 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 2500-5000 g a. i./ha, 3200-4500 g a. i./ha, 2600-3750 g a. i./ha, 3000-3500 g a. i./ha, 2800-3400 g a. i./ha, 2700-3100 g a. i./ha, 2900-4250 g a. i./ha, 3750-4750 g a. i./ha, 3300-4500 g a. i./ha, 2500-3500 g a. i./ha or 2600-4750 g a. i./ha.

Orbencarb

In some aspects, the FA/LSI herbicide may comprise orbecarb or an agriculturally acceptable salt or ester thereof. Orbencarb, shown below, is a thiocarbamate herbicide used for pre-emergence control of annual grasses, excluding wild oat species, and broadleaf weeds in barley, wheat, rye, maize, soybeans, cotton and turf at 4000-5000 g/ ha. Orbencarb, as well as methods for producing orbencarb, are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

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Orbencarb can be applied to vegetation or the area adjacent to the growth

- 16 046289 activity, or applied to soil or water to prevent the emergence or growth of vegetation in quantities sufficient to cause a herbicidal effect. In some aspects, orbencarb 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 4000 g a. i./ha or more, such as 4100 g a. i./ha or more, 4200 g a. i./ha or more, 4300 g a. i./ha or more, 4400 g a. i./ha or more, 4500 g a. i./ha or more, 4600 g a. i./ha or more, 4700 g a. i./ha or more, 4800 g a. i./ha or more or 4900 g a. i./ha or more; in the amount of 5000 g a. i./ha or less, such as 4900 g a. i./ha or less, 4800 g a. i./ha or less, 4700 g a. i./ha or less, 4600 g a. i./ha or less, 4500 g a. i./ha or less, 4400 g a. i./ha or less, 4300 g a. i./ha or less, 4200 g a. i./ha or less or 4100 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 4000-5000 g a. i./ha, 42004500 g a. i./ha, 4600-4900 g a. i./ha, 4100-4400 g a. i./ha, 4500-5000 g a. i./ha or 4100-4900 g a. i./ha.

Prosulfocarb

In some aspects, the FA/LSI herbicide may comprise prosulfocarb or an agriculturally acceptable salt or ester thereof. Prosulfocarb, shown below, is a thiocarbamate herbicide used for pre- and early post-emergence control of cereal and broadleaf weeds in winter wheat, winter barley and rye at 3000-4000 g/ha. Prosulfocarb, as well as methods for producing prosulfocarb, are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

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Prosulfocarb 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, prosulfocarb 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 250 g a. i./ha or more, such as 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, 290 g a. i./ha or more, 300 g a. i./ha or more, 310 ha. i./ha or more, 320 g a. i./ha or more, 325 g a.

i./ha or more, 330 g a. i./ha or more, 340 g a. i./ha or more, 350 g a. i./ha or more, 360 ha.

i./ha or more, 370 g a. i./ha or more, 375 g a. i./ha or more, 380 ha. i./ha or more, 390 ha.

i./ha or more, 400 g a. i./ha or more, 410 ha. i./ha or more, 420 g a. i./ha or more, 425 ha.

i./ha or more, 430 g a. i./ha or more, 440 g a. i./ha or more, 450 g a. i./ha or more, 460 ha.

i./ha or more, 470 g a. i./ha or more, 475 g a. i./ha or more, 480 g a. i./ha or more, 490 ha.

i./ha or more, 500 g a. i./ha or more, 525 g a. i./ha or more, 550 g a. i./ha or more, 575 ha.

i./ha or more, 600 g a. i./ha or more, 625 g a. i./ha or more, 650 g a. i./ha or more, 675 ha.

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 ha.

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, 1750 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, 2100 ha. i./ha or more, 2200 g a. i./ha or more, 2300 g a. i./ha or more, 2400 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, 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 or 3750 g a. i./ha or more; in the amount of 4000 g a. i./ha or less, such as 3750 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, 2700 g a. i./ha or less, 2600 g a. i./ha or less, 2500 g a. i./ha or less, 2400 g a. i./ha or less, 2300 g a. i./ha or less, 2200 g a. i./ha or less, 2100 ha. 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, 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.

- 17 046289

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 ha.

i./ha or less, 700 g a. i./ha or less, 675 g a. i./ha or less, 650 g a. i./ha or less, 625 ha.

i./ha or less, 600 g a. i./ha or less, 575 g a. i./ha or less, 550 g a. i./ha or less, 525 ha.

i./ha or less, 500 g a. i./ha or less, 490 g a. i./ha or less, 480 g a. i./ha or less, 475 ha.

i./ha or less, 470 g a. i./ha or less, 460 g a. i./ha or less, 450 g a. i./ha or less, 440 ha.

i./ha or less, 430 ha. i./ha or less, 425 g a. i./ha or less, 420 g a. i./ha or less, 410 ha. i./ha or less, 400 g a. i./ha or less, 390 g a. i./ha or less, 380 ha. i./ha or less, 375 ha. i./ha or less, 370 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, 330 g a. i./ha or less, 325 g a. i./ha or less, 320 g a. i./ha or less, 310 ha. i./ha or less, 300 g a. i./ha or less, 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; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 250-4000 g a. i./ha, 1350-3500 g a. i./ha, 1600-3750 g a. i./ha, 8002500 g a. i./ha, 1250-2000 g a. i./ha, 1100-3100 g a. i./ha, 1900-2400 g a. i./ha, 320-3200 g a. i./ha, 450-850 g a. i./ha, 2700-3400 g a. i./ha, 1500-2900 g a. i./ha or 260-3750 g a. i./ha.

Thiobencarb

In some aspects, the FA/LSI herbicide may comprise thiobencarb or an agriculturally acceptable salt or ester thereof. Thiobencarb, shown below, is a thiocarbamate herbicide used for pre- and early post-emergence control of Echinochloa, Leptochloa and Cyperus spp. and other cereal and annual broadleaf weeds of rice fields with sowing seeds in the ground and in seedling rice in an amount of 1500-7500 g/ha. Thiobencarb, as well as methods for producing thiobencarb, are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

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Thiobencarb 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, thiobencarb 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 1100 hectares. i./ha or more, such as 1120 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, 1750 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, 2100 ha. i./ha or more, 2200 g a. i./ha or more, 2300 g a. i./ha or more, 2400 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, 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, 3750 g a. i./ha or more, 4000 g a. i./ha or more, 4250 g a. i./ha or more, 4500 g a. i./ha or more, 4750 g a. i./ha or more, 5000 g a. i./ha or more, 5250 g a. i./ha or more, 5500 g a. i./ha or more, 5750 g a. i./ha or more, 6000 g a. i./ha or more, 6250 g a. i./ha or more, 6500 g a. i./ha or more, 6750 g a. i./ha or more, 7000 g a. i./ha or more or 7250 g a. i./ha or more; in the amount of 7500 g a. i./ha or less, such as 7250 g a. i./ha or less, 7000 g a. i./ha or less, 6750 g a. i./ha or less, 6500 g a. i./ha or less, 6250 g a. i./ha or less, 6000 g a. i./ha or less, 5750 g a. i./ha or less, 5500 g a. i./ha or less, 5250 g a. i./ha or less, 5000 g a. i./ha or less, 4750 g a. i./ha or less, 4500 g a. i./ha or less, 4250 g a. i./ha or less, 4000 g a. i./ha or less, 3750 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, 2700 g a. i./ha or less, 2600 g a. i./ha or less, 2500 g a. i./ha or less, 2400 g a. i./ha or less, 2300 g a. i./ha or less, 2200 g a. i./ha or less, 2100 ha. 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, 1200 g a. i./ha or less, 1150 g a. i./ha or less or 1120 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 1100-7500 g a. i./ha, 3750-6500 g a. i./ha, 1250-3400 g a. i./ha, 2600-5500 g a. i./ha, 1800-5000 g a. i./ha, 2100-6250 g a. i./ha, 1900-4000 g a. i./ha, 2700-4500 g a. i./ha, 2000-5250 g a. i./ha, 6500-7500 g a. i./ha,

- 18 046289

1300-4000 g a. i./ha or 1120-7250 g a. i./ha.

Thiocarbazil

In some aspects, the FA/LSI herbicide may comprise a thiocarbazyl or an agriculturally acceptable salt or ester thereof. Thiocarbazyl, shown below, is a thiocarbamate herbicide used for pre- or post-emergence control of grass weeds such as Echinochloa spp. and Lolium perenne, as well as sedge weeds such as Cyperus spp., in rice fields at 4000 g/ha. Thiocarbazyl, as well as methods for preparing thiocarbazyl, are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

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Triallat

In some aspects, the FA/LSI herbicide may comprise a triallate or an agriculturally acceptable salt or ester thereof. Triallate, shown below, is a thiocarbamate herbicide used for pre- or post-plant control of wild oat species and some annual grass weeds in wheat, barley, rye, broad beans, pea species, lentil species, beet species, oilseed rape, maize , flax, alfalfa, clover, vetch species, sainfoin, safflower species, sunflower species and vegetable plants in an amount of 1120-1680 g/ha. The triallate, as well as methods for producing the triallate, are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

CH ₃ O CI Η ₃ Ο^Ν

НзС^СНз θ’

The triallate 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, the triallate 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 1100 hectares. i./ha or more, such as 1120 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, 1550 g a. i./ha or more, 1600 g a. i./ha or more, 1650 g a. i./ha or more or 1680 g a. i./ha or more; in the amount of 1700 g a. i./ha or less, such as 1680 g a. i./ha or less, 1650 g a. i./ha or less, 1600 g a. i./ha or less, 1550 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, 1200 g a. i./ha or less, 1150 g a. i./ha or less or 1120 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 11001700 g a. i./ha, 1250-1600 g a. i./ha, 1550-1650 g a. i./ha, 1200-1500 g a. i./ha, 1150-1300 g a. i./ha, 1120-1400 g a. i./ha, 1450-1700 g a. i./ha, 1100-1350 g a. i./ha or 1120-1680 g a. i./ha.

Vernolat

In some aspects, the FA/LSI herbicide may comprise vernolate or an agriculturally acceptable salt or ester thereof. Vernolate, shown below, is a thiocarbamate herbicide used for pre- or post-plant control of wild oat species and some annual grass weeds in wheat, barley, rye, broad beans, pea species, lentil species, beet species, oilseed rape, maize , flax, alfalfa, clover, vetch species, sainfoin, safflower species, sunflower species and vegetable plants in an amount of 1120-1680 g/ha. Vernolate, as well as methods for producing vernolate, are known from the prior art. Its herbicidal activity is described, for example, in The Pesticide Manual, seventeenth edition, 2016.

O ^h ₃ ^c s^nA;-''''-- ^CH3

NzS.A

Vernolat can be applied to vegetation or the area adjacent to the growth

- 19 046289 activity, or applied to soil or water to prevent the emergence or growth of vegetation in quantities sufficient to cause a herbicidal effect. In some aspects, vernolate 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 1500 g a. i./ha or more, such as 1600 g a. i./ha or more, 1700 g a. i./ha or more, 1750 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, 2100 g a. i./ha or more, 2200 g a. i./ha or more, 2300 g a. i./ha or more, 2400 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, 2800 g a. i./ha or more or 2900 g a. i./ha or more; in the amount of 3000 g a. i./ha or less, such as 2900 g a. i./ha or less, 2800 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, 2400 g a. i./ha or less, 2300 g a. i./ha or less, 2200 g a. i./ha or less, 2100 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 or 1600 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 15,003,000 g a. i./ha, 1800-2500 g a. i./ha, 1700-1900 g a. i./ha, 1600-2800 g a. i./ha, 1750-2200 g a. i./ha, 2350-2900 g a. i./ha, 1600-2100 g a. i./ha, 1750-2700 g a. i./ha, 2100-2600 g a. i./ha, 1800-2300 g a. i./ha or 1600-2900 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 fatty acid and lipid synthesis inhibitor herbicide ( FA/LSI), its agriculturally acceptable salt or ester or mixtures thereof.

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 infestation or damage to undesirable 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 infestation of undesirable vegetation and 100% indicates for 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) an FA/LSI herbicide, an agriculturally acceptable salt or ester thereof ester or mixtures thereof results in an unexpectedly enhanced herbicidal effect on undesirable vegetation, even at application rates that are lower than those typically used for the herbicide to produce 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) the pyridine carboxylate herbicide or agriculturally acceptable N-oxide, salt, or ester thereof (in g eq/ha) and (b) the FA/LSI herbicide, its agriculturally acceptable salt or ester or mixtures thereof (in g a.i./ha) may be 1:7500 or more, such as 1:7000 or more, 1:6000 or more, 1: 5000 or more, 1:4000 or more, 1:3000 or more, 1:2500 or more, 1:2000 or more, 1:1500 or more, 1:1000 or more, 1:900 or more, 1:800 or more more, 1:700 or more, 1:600 or more, 1:500 or more, 1:400 or more, 1:300 or more, 1:250 or more, 1:200 or more, 1:150 or more, 1:100 or more, 1:90 or more, 1:80 or more, 1:75 or more, 1:70 or more, 1:60 or more, 1:50 or more, 1:40 or more, 1: 35 or more, 1:30 or more, 1:28 or more, 1:26 or more, 1:25 or more, 1:24 or more, 1:22 or more, 1:21 or more, 1:20 or more more, 1:18 or more, 1:16 or more, 1:15 or more, 1:14 or more, 1:12 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 or 1:1.1 or more; the weight ratio of (a) and (b) may be 1:1 or less, such as 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,

- 20 046289

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, 1:21 or less, 1: 22 or less, 1:24 or less, 1:25 or less, 1:26 or less, 1:28 or less, 1:30 or less, 1:35 or less, 1:40 or less, 1:50 or less less, 1:60 or less, 1:70 or less, 1:80 or less, 1:90 or less, 1:100 or less, 1:150 or less, 1:200 or less, 1:250 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: 1500 or less, 1:2000 or less, 1:2500 or less, 1:3000 or less, 1:4000 or less, 1:5000 or less, 1:6000 or less, or 1:7000 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 presented above, such as 1:7500 to 1:1, 1:5000 to 1: 1.2, from 1:2000 to 1:100, from 1:250 to 1:5, from 1:150 to 1:112, from 1:20 to 1:25, from 1:8 to 1:2 or from 1:7 to 1:1.5.

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) an FA/LSI herbicide its agriculturally acceptable salt or ester or mixtures thereof. 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.

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

Certain aspects of the disclosed herbicidal compositions include the addition of one or more additional pesticide active ingredients to the herbicidal compositions. 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, amiprofos-methyl, amitrol, ammonium sulfamate, anilofos, anizuron, asulam, atratone, atrazine, azaphenidine, azimsulfuron, aziprotrin, barban, BCRS, beflubutamide, benazolin, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron, benthio carb, bentazone, benzadox , benzfendizone, benzipram, benzobicyclone, benzophenap, benzofluor, benzoylprop, benzthiazuron, bilanaphos, bicyclopyrone, bifenox, bilanafos, bispiribac, borax, bromacil, bromobonil, bromobutide, bromophenoxime, bromoxynil, brompyrazone, butachlor, butafenacil, butamiphos, butenach ENT, butidazole, butiuron , butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrol, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole, chlorprocarb, carfentrazone-ethyl, CDEA, SEPC, chlomethoxyphene, chloramben, chloranocryl, chlorazifope, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazone, chlorimuron, chlornitrophen, chloropon, chloro

- 21 046289 toluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamide, cinidone-ethyl, cinmethylin, cinosulfuron, cisanilide, clacifos, clethodim, cliodinate, clodinafop-propargyl, clofop, clomazone, clomeprop, cloprop, cloproxydim, k lopiralide, 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, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, dietamquat, dietyl, diphenopentene, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, di methamethrin, dimethenamid, dimethenamid-P, dimexano, dimidazone, dinitramine, dinophenate, dinoprop, dinosam, dinoseb, dinoterb, difenamide, dipropetrin, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EVER, eglinasine, endothal, epronase, EPTC, Erbon, Esprokarb, Etalfluralin, this metesulfuron, ethbenzamide, etofenzulfuron, ethi-dimon, etilat, it isbenzamide, ethoxifen, ethoxyphon, ethinophen, ethnipromide, this is Benzanide, EXD, Fenasulas, Fenoproprop, Fenoksaprop, Fenksaprop-P. Fonoksapasprop-p-ethyl+ isoxadifen-ethyl, phenoxasulfone, fenquinotrione, fenteracol, fentiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P-butyl, fluazolate, flucarbazone, flusetosulfuron, fluchloralin, flufenacet , flufenican, flufenpyr -ethyl, flumetsulam, flumesin, flumiclorac-pentyl, flumioxazin, flumipropin, fluometuron, fluorodifen, fluoroglycophene, fluoromidine, 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, 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, isopolynate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortol, isoxaflutol , isoxapirifop, carbutylate, ketospiradox, lactofen, lenacyl, linuron, MAA, MAMA, esters and amines MCPA, MCPAthioethyl, MSRP, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metham, metamifop , metamitron , metazachlor, metflurazon, metabenzthiazuron, metalpropalin, metazol, methiobencarb, methiozolin, methiuron, metometon, metoprothrin, methyl bromide, methyl isothiocyanate, methyldimron, metobenzuron, methobromuron, metolachlor, metosulam, methoxuron, metribuzin, meth sulfuron, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morphamquat, MSMA, naproanilide, napropamide, napropamide-M, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrophen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, orthodichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon , oxapyrazone, oxasulfuron, oxaziclomefon, oxyfluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, petoxamide, phenizofam, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercurace tat, picloram, 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, profame, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prinachlor, pydanone, pyraclonil, pyraflufen, pyrasulfotol, pyrazogyl, pyrazone, pyrazolinate, pyrazosulfuron, pyrazoxifene, pyribenzoxime, pyributicarb, pyrichlor, pyridafol, pyridate, pyrifthalide, pyri minobak, pyrimisulfan, pyrithiobac-sodium, pyroxasulfone, piroxulam, quinclorac, quinmerac, quinoclamine, quinonamide, quizalofop, quizalofop-P-ethyl, quizalofop-P-tefuryl, rodetanil, rimsulfuron, saflufenacil, C-metolachlor, sebutylazine, sebumetone, sethoxydim, siduron, simazine , simeton, simethrine, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglicapin, swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumetone, terbutylazine, terbutryn, tetrafluron, tenylchlor, thiameturon, thiazafluron, thiazopyr, tidiazimine, tidiazuron, thiencarbazone, thifensulfuron, thiobencarb, thiaphenacyl, thiocarbazil, thioclorim, tolpiralate, topramesone, trawl koxidim, triallate, triafamone, triasulfuron, triaziflam, tribenuron, tricamba, triclopyr choline salt, triclopyr esters and amines, tridifan, triethazine, trifloxysulfuron, trifludimoxazine, trifluralin, triflusulfuron, triphop, trifopsim, trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron, vernolate, xylachlor and their salts, esters, optically active isomers and mixtures.

In some aspects, the additional pesticide or an agriculturally acceptable salt or ester thereof is premixed with (a), (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, a herbicide representing

- 22 046289 is an FA/LSI, its agriculturally acceptable salt or ester or mixtures thereof, presented in a premixed formulation with an additional pesticide.

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.

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 -Sc-alkylpolyglycoside; phosphoric acid and alcohol ethoxylates; natural primary (C1 ₂ -C16) 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 polyglycol ether of isooctyl, octyl or nonylphenol, 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 amines, polyethylenimine, polyvinylpyrrolidone and their copolymers.

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.

- 23 046289

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 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, isoxadifen-ethyl, jiecaowan, jiecaosi, mefenpyr, mefenpyr-diethyl, mephenate, naphthalene anhydride, 2,2,5-trimethyl-3(dichloroacetyl)-1,3-oxazolidine, 4- (dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane, oxabetrinyl, R29148 and N-phenylsulfonylbenzoic acid amides, as well as their agriculturally acceptable salts and, provided they contain a carboxyl group, their agriculturally acceptable salts agricultural derivatives view. 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;Ndimethylalkylamides, 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 husks, wheat flour, soy 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) an FA/LSI herbicide or an agriculturally acceptable salt thereof or ester may be in suspended, emulsified, dissolved or solid forms. 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 in an aqueous solution that can be diluted before use. In various aspects, (a) or (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

- 24 046289 at temperatures -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 centipoise (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 total amounts 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 the total amount at a concentration of only about 1 wt. %, approximately 2.5 wt. %, approximately 5 wt. %, approximately 7.5 wt. %, approximately 10 wt. %, approximately 15 wt. %, approximately 20 wt. %, approximately 25 wt. %, approximately 30 wt. %, approximately 35 wt. %, approximately 40 wt. %, approximately 45 wt. %, up to approximately 50 wt. %, approximately 55 wt. %, approximately 60 wt. %, approximately 65 wt. %, approximately 70 wt. %, approximately 75 wt. %, approximately 80 wt. %, approximately 85 wt. %, approximately 90 wt. %, approximately 95 wt. %, approximately 97 wt. % or within any range defined by any two of the above values, for example from about 1 wt. % to approximately 97 wt. %, from about 10 wt. % to approximately 90 wt. %, from about 20 wt. % to approximately 45 wt. % and from about 25 wt. % to approximately 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.%) based on 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) an FA/LSI herbicide, an agriculturally acceptable salt or ester thereof, or mixtures thereof. In some aspects, the composition may be presented in the form of a single package composition comprising both (a) and (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 in 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 composition

- 25 046289 tions described in this document.

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-emergence (before the emergence of unwanted vegetation) or post-emergence (eg, during 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 an FA/LSI herbicide are used simultaneously. In some aspects, the pyridine carboxylate herbicide and the FA/LSI herbicide are applied sequentially, such as without or with minimal delay, within about 10 minutes, within about 20 minutes, within about 30 minutes, within within approximately 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 if 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, and nature 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

- 26 046289 latent 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, the compositions and methods disclosed herein can also be used in forestry applications (eg, 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 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 dicamba, phenoxyauxines, pyridyloxyauxines, aryloxyphenoxypropionates, acetyl-CoA carboxylase (ACCase) inhibitors, imidazolinones, acetolactate synthase (ALS) inhibitors, 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors ), 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 auxin herbicides, HPPD inhibitors, PPO, 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, more, or packaged characteristics that impart tolerance to one or more chemicals or several 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) and (b) 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.,

- 27 046289 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), common rosebush (Galeopsis tetrahit), bedstraw (Galium aparine), common sunflower (Helianthus annuus), Desmodium tortuosum, ryegrass (Lolium multiflorum), kochia scoparia, Medicago arabica, Mercurialis annua, Myosotis arvensis , self-seeded poppy (Papaver rhoeas), Raphanus raphanistrum, blunt-leaved sorrel (Rumex obtusifolius), Russian saltwort (Salsola kali), field mustard (Sinapis arvensis), Sonchus arvensis, Thlaspi arvense, Tagetes minuta, Richardia brasiliensis, Plantago major, Plantago lanceolata, Veronica persica (Veronica persica), amaranth (Amaranthus retroflexus), winter rapeseed (Brassica napus), white pigweed (Chenopodium album), thistle (Cirsium arvense), edible milkweed (Cyperus esculentus), spurge (Euphorbia heterophylla), wild lettuce (Lactuca serriola), purple lamium (Lamium purpureum), chamomile (Matricaria chamomilla), odorless chamomile (Matricaria inodora), navel (Anthemis arvensis), buckwheat (Fagopyrum esculentum), knotweed (Polygonum convulvus), Faber's foxtail ( 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 that are resistant or tolerant to a herbicide. 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 procedure - assessment of post-emergence herbicidal 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 from 5.2 to 6.2 and organic matter content,

- 28 046289 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 supplemental lighting was provided as needed using ceiling-mounted 1000-watt metal halide 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 FA/LSI herbicide) were prepared by adding weighed amounts or aliquots of FA/LSI herbicide to stock solutions of Compound A or Compound B to produce 12 ml spray solutions in two-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 herbicides based on pyridine carboxylate (component a) are given in g equivalent. l./ha, and all rates of application of herbicides representing FA/LSI (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 benfuresat were tested on undesirable vegetation species, including spring rape (BRSNN, Brassica napus), knotweed (POLCO, Polygonum convolvulus), field mustard (SINAR, Sinapis arvensis), Russian solyanka (SASKR, Salsola kali) , kochia (KCHSC, Kochia scoparia), amaranth (AMARE, Amaranthus retroflexus), 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 1 below.

- 29 046289

Table 1

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

Application rate (g/ha) Connection A 7.5 10 0 7.5 10 Benfuresat 0 0 150 150 150 BRSNN Observable 55 60 5 90 90 Expected - - - 57 62 P 32 28 POLCO Observable 70 78 0 98 100 Expected - - - 70 78 R 28 23 SINAR Observable 88 92 0 94 98 Expected - - - 88 92 R 6 6 SASKR Observable 45 60 0 73 70 Expected - - - 45 60 R 28 10 KCHSC Observable 50 58 0 70 78 Expected - - - 50 58 R 20 20 AMARE Observable 100 100 10 97 100 Expected - - - 100 100 R -3 0 CHEAL Observable 70 83 0 95 96 Expected - - - 70 83 R 25 14 MATCH Observable 13 15 0 15 20 Expected - - - 13 15 R 3 5 TRZAS Observable 0 0 0 0 0 Expected - - - 0 0 R 0 0 HORVS Observable 8 0 10 8 18 Expected - - - 17 10 R -9 8

g/ha=grams per hectare

BRSNN=/fra.s.s/cz7 napus (spring rapeseed)

POLCO=Polygonum convolvulus (convolvulus) STNAR.=Sinapis arvensis (field mustard)

SASKR.=Salsola kali (Russian solyanka) KCHSC=Xoc/wa scoparia (kochia)

AMNRE=Amaranthus retroflexus (amaranth) CW.AL=Chenopodium album L. (white pigweed) MATCH=AA7//7cz7/777 chamomilla (chamomile) TRZAS=7/7//c7//7z aestivum (spring wheat) HORVS= Zforafewm vulgare (spring barley)

- 30 046289

Example 2

Compositions containing compound A and prosulfocarb were tested on undesirable vegetation species, including VIOTR, Viola tricolor, CHEAL, Chenopodium album L., STEME, Stellaria media, LOLMU, Lolium multiflorum), common barnacle (ECHCG, Echinochloa crus-galli), blood red crabgrass (DIGSA, Digitaria sanguinalis), bindweed (POLCO, Polygonum convolvulus), thistle (CIRAR, Cirsium arvense), spring rape (BRSNN, Brassica napus ), Faber's foxtail (SETFA, Setaria faberi), soybean plant (GLXMA, Glycine max) and kochia (KCHSC, Kochia scoparia), in order to determine the effectiveness of the compositions against these types of unwanted vegetation.

The results are summarized in table. 2 below.

table 2

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

Application rate (g/ha) Compound A 7.5 10 0 7.5 10 Prosulfocarb 0 0 250 250 250 VIOTR Observable 10 18 0 15 23 Expected - - - 10 18 R 5 5 CHEAL Observable 97 93 0 99 100 Expected - - - 97 93 R 2 7 STEM Observable 100 97 0 99 100 Expected - - - 100 97 R -2 4 LOLMU Observable 0 0 0 15 20 Expected - - - 0 0 R 15 20 ECHCG Observable 73 78 0 83 88 Expected - - - 73 78 R 10 10 DIGSA Observable 45 25 0 thirty 43 Expected - - - 45 25 R -15 18 POLCO Observable 75 70 0 85 75 Expected - - - 75 70 R 10 5 CIRAR Observable 23 20 0 28 40 Expected - - - 23 20 R 5 20 BRSNN Observable 73 83 0 83 78 Expected - - - 73 83 R 10 -5 SETFA Observable 70 70 0 75 88 Expected - - - 70 70

- 31 046289

R 5 18 GLXMA Observable 93 95 0 98 100 Expected - - - 93 95 R 5 5 KCHSC Observable 60 65 0 68 73 Expected - - - 60 65 R 8 8

g/ha=grams per hectare

VIOTR=Fzo/6z tricolor (tricolor violet) CHEM^=Chenopodium album L. (white pigweed) STEME=Ste//izrza media (medium chickweed) LOLMU=Zo/zzzz?z multiflorum (multifloral chaff) ECHCG=Echinochloa crus-galli (common barnyard grass) DIGSk=Digitaria sanguinalis (blood red crabgrass) EOECO=Polygonum convolvulus (convolvulus knotweed) CIRAR=C//'.s////z? arvense (field thistle) BRSNN=Bra55zc6/ napus (spring rape) SETFA=5etariafaberi (Faber's bristle grass) GLXMA=G/yczz?e max (soybean) KCHSC=Koc/zzzz scoparia (kochia)

Example 3

Compositions containing compound A and thiobencarb 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), amaranth (AMARE, Amaranthus retroflexus), 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. 3 below.

Table 3

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

Application rate (g/ha) Compound A 7.5 10 0 7.5 10 Thiobencarb 0 0 1120 1120 1120 BRSNN Observable 55 60 10 93 95 Expected - - - 60 64

- 32 046289

P 33 31 POLCO Observable 70 78 0 90 99 Expected - - - 70 78 P 20 21 SINAR Observable 88 92 5 100 89 Expected - - - 88 92 P 12 -3 SASKR Observable 45 60 0 73 75 Expected - - - 45 60 R 28 15 KCHSC Observable 50 58 0 68 70 Expected - - - 50 58 R 18 13 AMARE Observable 100 100 10 98 98 Expected - - - 100 100 R -3 -3 CHEAL Observable 70 83 0 85 85 Expected - - - 70 83 R 15 3 MATCH Observable 13 15 15 73 77 Expected - - - 26 28 R 47 49 TRZAS Observable 0 0 0 0 0 Expected - - - 0 0 R 0 0 HORVS Observable 8 0 0 0 10 Expected - - - 8 0 R -8 10

g/ha=grams per hectare

BRSNN=/7zz/.s.szcz/ napus (spring rapeseed)

POLCO=Polygonum convolvulus (convolvulus knotweed)

S\NPJk=Sinapis arvensis (field mustard)

S ASKR=5"Ao/" kali (Russian solyanka)

KCHSC=Kochia scoparia (kochia)

MANRE=Amaranthus retroflexus (amaranth)

C\AENL=Chenopodium album L. (white pigweed)

MATCH=AfaZrzcarza chamomilla (chamomile)

TRZAS=7z7/zc7zz7? aestivum (spring wheat)

HORV S=Horde and m vulgare (spring barley)

Example 4

Compositions containing Compound A and esprocarb were tested on undesirable vegetation species including spring rape (BRSNN, Brassica napus), field mustard (SINAR, Sinapis arvensis), kochia (KCHSC, Kochia scoparia), Russian solyanka (SASKR, Salsola kali), amaranth (AMARE, Amaranthus retroflexus), 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 was measured

- 33 046289 in relation to each agricultural crop.

The results are summarized in Table 4 below.

Table 4

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

Application rate (g/ha) Connection A 7.5 10 0 7.5 10 Esprocarb 0 0 420 420 420 BRSNN Observable 55 70 0 80 73 Expected - - - 55 70 P 25 3 SINAR Observable 85 90 0 100 100 Expected - - - 85 90 R 15 3 KCHSC Observable 50 55 0 63 63 Expected - - - 50 55 R 13 8 SASKR Observable 38 63 0 70 75 Expected - - - 38 63 R 33 13 AMARE Observable 70 98 15 99 87 Expected - - - 75 98 R 24 -AND CHEAL Observable 60 90 0 90 85 Expected - - - 60 90 R thirty -5 MATCH Observable 0 33 5 33 33 Expected - - - 5 36 R 28 -3 CIRAR Observable 10 23 0 60 45 Expected - - - 10 23 R 50 23 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

- 34 046289 g/ha=grams per hectare

BRSNN=//ra.s.s7c<7 napus (spring rapeseed)

SINAR=,S7//ap/.s arvensis (field mustard) KCHSC=Xoc/wa scoparia (kochia) SASKR.=Salsola kali (Russian solyanka) AMARE=Amaranthus reirof/exus (amaranth) CUEAL=Chenopodium album L. (pigweed white) XI ATCH=AA7//7cz7/7a chamomilla (chamomile) CnkAR=Cirsium arvense (field thistle) TRZAS=7/7//c7//77 aestivum (spring wheat) HORVS=Zforafewm vulgare (spring barley)

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 expressions comprising and including are used herein to describe various aspects, the expressions essentially consisting of and consisting of may be used instead of containing and including to provide more specific aspects of the present invention, 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 (16)

CLAIM 1. Heroicidal 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 fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide, an agriculturally acceptable salt or ester thereof, or mixtures thereof, wherein the weight ratio is ( a) (in g eq. k./ha) and (b) (in g a. i./ha) ranges from 1: 250 to 1:5. 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 : - 35 046289 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 FA/LSI herbicide is selected from the group consisting of benfuresate, bensulide, butylate, cycloate, dalapone, EPTC (S-ethyldipropylthiocarbamate), esprocarb, ethophumesate, flupropanate, molinate, orbencarb, prosulfocarb, thiobencarb, thiocarbazyl, triallate, vernolate, agriculturally acceptable salts or esters thereof, and mixtures thereof. 5. Composition according to any one of claims 1-4, where the weight ratio of (a) (in geq/ha) and (b) (in g a.i./ha) is from 1: 150 to 1: 15 . 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, wherein the composition does not contain a herbicidal active ingredient in addition to (a) and (b). 8. 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): 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 fatty acid and lipid synthesis inhibitor (FA/LSI) herbicide, an agriculturally acceptable salt or ester thereof, or mixtures thereof; wherein the pyridine carboxylate herbicide is used in an amount of at least 0.1 g eq. k./ha, where FA/LSI is applied in an amount of at least 100 g a. i./ha; and where the weight ratio of (a) (in g eq./ha) and (b) (in g a. i./ha) is from 1: 250 to 1:5. 9. The method of claim 8, wherein the pyridine carboxylate herbicidal compound is cyanomethyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate : 10. The method according to claim 8, 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 : - 36 046289 11. The method according to any one of claims 8 to 10, wherein the pyridine carboxylate herbicide and the FA/LSI herbicide are applied simultaneously. 12. The method according to any one of claims 8-11, where the pyridine carboxylate-based herbicide is provided in an amount of 0.1 g eq. k./ha up to 300 g eq. k./ha. 13. The method according to any one of claims 8 to 12, wherein the FA/LSI herbicide is selected from the group consisting of benfuresate, bensulide, butylate, cycloate, dalapone, EPTC (S-ethyldipropylthiocarbamate), esprocarb, ethophumesate, flupropanate, molinate, orbencarb, prosulfocarb, thiobencarb, thiocarbazyl, triallate, vernolate, agriculturally acceptable salts or esters thereof, and mixtures thereof. 14. Method according to any one of claims 8-13, where the weight ratio of (a) (in g eq. k./ha) and (b) (in g a. i./ha) is from 1: 150 to 1: 15. 15. The method according to any one of claims 8-14, further including the use of an antidote. 16. Method according to any one of claims 8 to 15, wherein the composition does not contain a herbicidal active ingredient in addition to (a) and (b).