EA045740B1 - COMPOSITIONS CONTAINING pyridine carboxylate-based herbicides and herbicides that are 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors - Google Patents

Description

Technical field of the invention

The present invention includes compositions containing (a) a pyridine carboxylate herbicide or an agriculturally acceptable salt thereof and (b) a 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide or an agriculturally acceptable salt thereof 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 desirable vegetation. To help control unwanted growth, researchers have come up with a variety of chemicals and chemical formulations that are effective in controlling such unwanted growth. However, there is a need for new herbicidal compositions and methods for controlling the growth of unwanted vegetation in desired crops.

Brief description of the invention

Disclosed herein are compositions that can be used as herbicides, for example, on agricultural crops. The compositions contain (a) a pyridine carboxylate herbicide or an agriculturally acceptable salt thereof and (b) a 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide or an agriculturally acceptable salt or ester thereof. Weight ratio of herbicide based on pyridine carboxylate in g eq. k./ha to (b) HPPD inhibitor herbicide, in g a. i./ha ranges from 1:500 to 50:1.

In some aspects, the composition contains (a) a pyridine carboxylate herbicide defined by formula (I):

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 independently represent hydrogen;

or an agriculturally acceptable salt thereof; and (b) a 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide or an agriculturally acceptable salt or ester thereof.

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 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide, or an agriculturally acceptable salt or ester thereof.

In some aspects, the composition contains (a) propargyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridin-2-carboxylate, a pyridine carboxylate herbicidal compound called later in this document by connection B:

- 1 045740

Compound B, or an agriculturally acceptable salt thereof; and (b) a 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide, or an agriculturally acceptable salt or ester thereof.

In some aspects, (b) may include a herbicide that is an HPPD inhibitor. In some aspects, (b) may include benzobicyclone, benzophenap, bicyclopyrone, fenquinotrione, isoxachlortol, isoxaflutole, mesotrione, pyrasulfotol, pyrazolinate, pyrazoxifene, sulcotrione, tembotrione, tefuryltrione, topramesone, or an agriculturally acceptable salt thereof, or combinations 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 based on pyridine carboxylate or an agriculturally acceptable salt thereof; and (b) a 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor herbicide or an agriculturally acceptable salt or ester thereof. In some aspects, (a) and (b) are used simultaneously. In some aspects, (a) and (b) are applied sequentially. In some aspects, (a) and (b) are applied before the emergence of unwanted vegetation. In some aspects, (a) and (b) are applied after the unwanted vegetation has emerged. In some aspects, the unwanted vegetation is found in cereal crops. In some aspects, the unwanted vegetation is found in maize, wheat, barley, rice, sorghum, millet, or oat species. In some aspects, unwanted vegetation is found in broadleaf crops. In some aspects, the unwanted vegetation is found in canola, flax, sunflower, soybean or cotton.

In some aspects, the pyridine carboxylate(a) herbicide can be applied in an amount from 0.1 grams acid equivalent per hectare (g eq/ha) to 300 g eq. k./ha. In some cases, (a) and (b) may be used in a weight ratio of 1:50 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 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide or an agriculturally acceptable salt or salt thereof. ester. The present invention also includes methods for controlling unwanted vegetation. In some aspects, the unwanted vegetation is found in cereal crops. In some aspects, the unwanted vegetation is found in maize, wheat, barley, rice, sorghum, millet, or oat species. In some aspects, unwanted vegetation is found in broadleaf crops. In some aspects, the unwanted vegetation is found in canola, flax, sunflower, soybean or cotton.

I. Definitions.

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

As used herein, the terms herbicide and herbicidal active ingredient can be understood to include an active ingredient that kills, controls or otherwise

- 2045740 adversely modifies the growth of vegetation, in particular undesirable 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 term warn or similar terms, 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 a weed relative to a 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, pre-emergence contacting soil or water, post-emergence contacting unwanted vegetation, or contacting an area adjacent to unwanted vegetation.

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

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

As used herein, the term undesirable vegetation refers to vegetation that is undesirable in a specified area, such as weed species. Herbicides or 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.

As used herein, agriculturally acceptable salts and esters may be meant 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.

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):

formula I,

- 3 045740 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 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide or an agriculturally acceptable salt or ester thereof.

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-1H-indol-6-yl) pyridine-2-carboxylate, compound A:

Compound A, or an agriculturally acceptable salt thereof; and (b) a 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide, or an agriculturally acceptable salt or ester 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-1H-indol-6-yl) pyridine-2-carboxylate, compound B:

Compound B, or an agriculturally acceptable salt thereof; and (b) a 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor herbicide, or an agriculturally acceptable salt or ester thereof.

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

In some aspects, the pyridine carboxylate herbicide may be provided in the form of an agriculturally acceptable salt. Exemplary agriculturally acceptable pyridine carboxylate herbicide salts include, but are not limited to, sodium salts, potassium salts, ammonium salts, or substituted ammonium salts, particularly mono-, di-, and tri- _C1C8 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 R ⁹ - R ¹² are sterically compatible.

The pyridine carboxylate herbicide or agriculturally acceptable salts thereof may be applied to vegetation or an area adjacent to vegetation, or applied to soil or water, to prevent the emergence or growth of vegetation in an amount sufficient to cause herbicidal effect. In some aspects, the pyridine carboxylate herbicide or agriculturally acceptable salts thereof are applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent emergence or growth of vegetation in an amount of 0.1 gram equivalent acid 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. sq./ha

- 4 045740 or more, 1 g eq. k./ha or more, 1.1 g eq. k./ha or more, 1.2 g eq. k./ha or more, 1.3 g eq. k./ha or more, 1.4 g eq. k./ha or more, 1.5 g eq. k./ha or more, 1.6 g eq. k./ha or more, 1.7 g eq. k./ha or more, 1.8 g eq. k./ha or more, 1.9 g eq. k./ha or more, 2 g eq. k./ha or more, 2.25 g eq. k./ha or more, 2.5 g eq. k./ha or more, 2.75 g eq. k./ha or more, 3 g eq. k./ha or more, 4 g eq. k./ha or more, 5 g eq. k./ha or more, 6 g eq. k./ha or more, 7 g eq. k./ha or more, 8 g eq. k./ha or more, 9 g eq. k./ha or more, 10 g eq. k./ha or more, 11 g eq. k./ha or more, 12 g eq. k./ha or more, 13 g eq. k./ha or more, 14 g eq. k./ha or more, 15 g eq. k./ha or more, 16 g eq. k./ha or more, 17 g eq. k./ha or more, 18 g eq. k./ha or more, 19 g eq. k./ha or more, 20 g eq. k./ha or more, 22 g eq. k./ha or more, 24 g eq. k./ha or more, 25 g eq. k./ha or more, 26 g eq. k./ha or more, 28 g eq. k./ha or more, 30 g eq. k./ha or more, 32 g eq. k./ha or more, 34 g eq. k./ha or more, 35 g eq. k./ha or more, 36 g eq. k./ha or more, 38 g eq. k./ha or more, 40 g eq. k./ha or more, 42.5 g eq. k./ha or more, 45 g eq. k./ha or more, 47.5 g eq. k./ha or more, 50 g eq. k./ha or more, 52.5 g eq. k./ha or more, 55 g eq. k./ha or more, 57.5 g eq. k./ha or more, 60 g eq. k./ha or more, 65 g eq. k./ha or more, 70 g eq. k./ha or more, 75 g eq. k./ha or more, 80 g eq. k./ha or more, 85 g eq. k./ha or more, 90 g eq. k./ha or more, 95 g eq. k./ha or more, 100 g eq. k./ha or more, 110 g eq. k./ha or more, 120 g eq. k./ha or more, 130 g eq. k./ha or more, 140 g eq. k./ha or more, 150 g eq. k./ha or more, 160 g eq. k./ha or more, 170 g eq. k./ha or more, 180 g eq. k./ha or more, 190 g eq. k./ha or more, 200 g eq. k./ha or more, 210 g eq. k./ha or more, 220 g eq. k./ha or more, 230 g eq. k./ha or more, 240 g eq. k./ha or more, 250 g eq. k./ha or more, 260 g eq. k./ha or more, 270 g eq. k./ha or more, 280 g eq. k./ha or more or 290 g eq. k./ha or more; in the amount of 300 g eq. k./ha or less, such as 290 g eq. k./ha or less, 280 g eq. k./ha or less, 270 g eq. k./ha or less, 260 g eq. k./ha or less, 250 g eq. k./ha or less, 240 g eq. k./ha or less, 230 g eq. k./ha or less, 220 g eq. k./ha or less, 210 g eq. k./ha or less, 200 g eq. k./ha or less, 190 g eq. k./ha or less, 180 g eq. k./ha or less, 170 g eq. k./ha or less, 160 g eq. k./ha or less, 150 g eq. k./ha or less, 140 g eq. k./ha or less, 130 g eq. k./ha or less, 120 g eq. k./ha or less, 110 g eq. k./ha or less, 100 g eq. k./ha or less, 95 g eq. k./ha or less, 90 g eq. k./ha or less, 85 g eq. k./ha or less, 80 g eq. k./ha or less, 75 g eq. k./ha or less, 70 g eq. k./ha or less, 65 g eq. k./ha or less, 60 g eq. k./ha or less, 57.5 g eq. k./ha or less, 55 g eq. k./ha or less, 52.5 g eq. k./ha or less, 50 g eq. k./ha or less, 47.5 g eq. k./ha or less, 45 g eq. k./ha or less, 42.5 g eq. k./ha or less, 40 g eq. k./ha or less, 38 g eq. k./ha or less, 36 g eq. k./ha or less, 35 g eq. k./ha or less, 34 g eq. k./ha or less, 32 g eq. k./ha or less, 30 g eq. k./ha or less, 28 g eq. k./ha or less, 26 g eq. k./ha or less, 25 g eq. k./ha or less, 24 g eq. k./ha or less, 22 g eq. k./ha or less, 20 g eq. k./ha or less, 19 g eq. k./ha or less, 18 g eq. k./ha or less, 17 g eq. k./ha or less, 16 g eq. k./ha or less, 15 g eq. k./ha or less, 14 g eq. k./ha or less, 13 g eq. k./ha or less, 12 g eq. k./ha or less, 11 g eq. k./ha or less, 10 g eq. k./ha or less, 9 g eq. k./ha or less, 8 g eq. k./ha or less, 7 g eq. k./ha or less, 6 g eq. k./ha or less, 5 g eq. k./ha or less, 4 g eq. k./ha or less, 3 g eq. k./ha or less, 2.75 g eq. k./ha or less, 2.5 g eq. k./ha or less, 2.25 g eq. k./ha or less, 2 g eq. k./ha or less, 1.9 g eq. k./ha or less, 1.8 g eq. k./ha or less, 1.7 g eq. k./ha or less, 1.6 g eq. k./ha or less, 1.5 g eq. k./ha or less, 1.4 g eq. k./ha or less, 1.3 g eq. k./ha or less, 1.2 g eq. k./ha or less, 1.1 g eq. k./ha or less, 1 g eq. k./ha or less, 0.9 g eq. k./ha or less, 0.8 g eq. k./ha or less, 0.7 g eq. k./ha or less, 0.6 g eq. k./ha or less, 0.5 g eq. k./ha or less, 0.4 g eq. k./ha or less, 0.3 g eq. k./ha or less or 0.2 g eq. kg/ha or less; or in an amount within any range defined between any pair of the preceding values, such as 0.1-300 g eq. k./ha, 1-150 g eq. k./ha, 10-200 g eq. k./ha, 25 g eq. k./ha - 75 g eq. k./ha or 40-100 g eq. k./ha.

III. Herbicides that are HPPD inhibitors.

In addition to the pyridine carboxylate herbicide of formula (I) or agriculturally acceptable salts thereof, the compositions may contain an inhibitor of 4-hydroxyphenylpyruvate dioxygenase (HPPD), an oxygenase enzyme involved in energy production in plants and higher eukaryotes. Examples of HPPD inhibitors include benzobicyclone, benzophenap, bicyclopyrone, fenquinotrione, isoxachlortol, isoxaflutole, lancotrione, mesotrione, pyrasulfotol, pyrazolinate, pyrazoxifene, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramesone, or agriculturally acceptable salts and esters thereof, and combinations thereof .

The HPPD inhibitor, or an agriculturally acceptable salt or ester thereof, may be applied to vegetation or an area adjacent to vegetation, or applied to soil or water, to prevent the emergence or growth of vegetation in an amount sufficient to cause a herbicidal effect. In some aspects, an HPPD inhibitor or an agriculturally acceptable salt or ester thereof is applied to vegetation or an area adjacent to vegetation, or is applied to soil or water to prevent the emergence or growth of vegetation in a plant.

- 5 045740 as 1 gram of active ingredient per hectare (g a.i./ha) or more, such as 1.1 g a. i./ha or more, 1.25 g a. i./ha or more, 1.5 g a. i./ha or more, 1.75 g a. i./ha or more, 2 g a. i./ha or more, 2.5 g a. i./ha or more, 3 g a. i./ha or more, 3.5 g a. i./ha or more, 4 g a. i./ha or more, 5 g a. i./ha or more, 6 g a. i./ha or more, 7 g a. i./ha or more, 8 g a. i./ha or more, 9 g a. i./ha or more, 10 g a. i./ha or more, 11 g a. i./ha or more, 12 g a. i./ha or more, 13 g a. i./ha or more, 14 g a. i./ha or more, 15 g a. i./ha or more, 16 g a. i./ha or more, 17 g a. i./ha or more, 18 g a. i./ha or more, 19 g a. i./ha or more, 20 g a. i./ha or more, 21 g a. i./ha or more, 22 g a. i./ha or more, 23 g a. i./ha or more, 24 g a. i./ha or more, 25 g a. i./ha or more, 26 g a. i./ha or more, 27 g a. i./ha or more, 28 g a. i./ha or more, 29 g a. i./ha or more, 30 g a. i./ha or more, 31 g a. i./ha or more, 32 g a. i./ha or more, 33 g a. i./ha or more, 34 g a. i./ha or more, 35 g a. i./ha or more, 36 g a. i./ha or more, 37 g a. i./ha or more, 38 ha. i./ha or more, 39 g a. i./ha or more, 40 g a. i./ha or more, 41g a. i./ha or more, 42 g a. i./ha or more, 43 g a. i./ha or more, 44 g a. i./ha or more, 45 g a. i./ha or more, 50 g a. i./ha or more, 55 g a. i./ha or more, 60 g a. i./ha or more, 65 g a. i./ha or more, 70 g a. i./ha or more, 75 g a. i./ha or more, 80 g a. i./ha or more, 85 g a. i./ha or more, 90 g a. i./ha or more, 95 g a. i./ha or more, 100 g a. i./ha or more, 110 g a. i./ha or more, 120 g a. i./ha or more, 130 g a. i./ha or more, 140 g a. i./ha or more, 150 g a. i./ha or more, 160 g a. i./ha or more, 170 g a. i./ha or more, 180 g a. i./ha or more, 190 g a. i./ha or more, 200 g a. i./ha or more, 220 g a. i./ha or more, 240 g a. i./ha or more, 250 g a. i./ha or more, 260 g a. i./ha or more, 280 g a. i./ha or more, 300 g a. i./ha or more, 320 g a. i./ha or more, 340 g a. i./ha or more, 350 g a. i./ha or more, 360 g a. i./ha or more, 380 g a. i./ha or more, 400 g a. i./ha or more, 450 g a. i./ha or more, 500 g a. i./ha or more, 550 g a. i./ha or more, 600 g a. i./ha or more, 650 g a. i./ha or more, 700 g a. i./ha or more, 750 g a. i./ha or more, 800 g a. i./ha or more, 850 g a. i./ha or more, 900 g a. i./ha or more, 950 g a. i./ha or more, 1000 g a. i./ha or more, 1050 g a. i./ha or more, 1100 g a. i./ha or more, 1150 g a. i./ha or more, 1200 g a. i./ha or more, 1250 g a. i./ha or more, 1300 g a. i./ha or more, 1350 g a. i./ha or more, 1400 g a. i./ha or more, 1450 g a. i./ha or more, 1500 g a. i./ha or more, 1600 g a. i./ha or more, 1700 g a. i./ha or more, 1800 g a. i./ha or more, 1900 g a. i./ha or more, 2000 g a. i./ha or more, 2050 g a. i./ha or more, 2100 g a. i./ha or more, 2150 g a. i./ha or more, 2200 g a. i./ha or more, 2240 g a. i./ha or more, 2250 g a. i./ha or more, 2300 g a. i./ha or more, 2350 g a. i./ha or more, 2400 g a. i./ha or more, 2450 g a. i./ha or more, 2500 g a. i./ha or more, 2600 g a. i./ha or more, 2700 g a. i./ha or more, 2750 g a. i./ha or more, 2800 g a. i./ha or more, 2900 g a. i./ha or more, 3000 g a. i./ha or more, 3100 g a. i./ha or more, 3200 g a. i./ha or more, 3250 g a. i./ha or more, 3300 g a. i./ha or more, 3400 g a. i./ha or more, 3500 g a. i./ha or more, 3600 g a. i./ha or more, 3700 g a. i./ha or more, 3750 g a. i./ha or more, 3800 g a. i./ha or more, 3900 g a. i./ha or more, 3950 g a. i./ha or more, 4000 g a. i./ha or more, 4100 g a. i./ha or more, 4200 g a. i./ha or more, 4250 g a. i./ha or more, 4250 g a. i./ha or more, 4300 g a. i./ha or more, or 4350 g a. i./ha or more, or 4400 g a. i./ha or more; in the amount of 4500 g a. i./ha or less, such as 4450 g a. i./ha or less, 4400 g a. i./ha or less, 4350 g a. i./ha or less, 4300 g a. i./ha or less, 4250 g a. i./ha or less, 4100 g a. i./ha or less, 4000 g a. i./ha or less, 3950 g a. i./ha or less, 3900 g a. i./ha or less, 3800 g a. i./ha or less, 3750 g a. i./ha or less, 3700 g a. i./ha or less, 3600 g a. i./ha or less, 3500 g a. i./ha or less, 3400 g a. i./ha or less, 3300 g a. i./ha or less, 3250 g a. i./ha or less, 3200 g a. i./ha or less, 3100 g a. i./ha or less, 3000 g a. i./ha or less, 2900 g a. i./ha or less, 2800 g a. i./ha or less, 2750 g a. i./ha or less, 2700 g a. i./ha or less, 2600 g a. i./ha or less, 2500 g a. i./ha or less, 2450 g a. i./ha or less, 2400 g a. i./ha or less, 2350 g a. i./ha or less, 2300 g a. i./ha or less, 2250 g a. i./ha or less, 2240 g a. i./ha or less, 2200 g a. i./ha or less, 2150 g a. i./ha or less, 2100 g a. i./ha or less, 2050 g a. i./ha or less, 2000 g a. i./ha or less, 1900 g a. i./ha or less, 1800 g a. i./ha or less, 1750 g a. i./ha or less, 1700 g a. i./ha or less, 1600 g a. i./ha or less, 1500 g a. i./ha or less, 1450 g a. i./ha or less, 1400 g a. i./ha or less, 1350 g a. i./ha or less, 1300 g a. i./ha or less, 1250 g a. i./ha or less, 1240 g a. i./ha or less, 1200 g a. i./ha or less, 1150 g a. i./ha or less, 1100 g a. i./ha or less, 1050 g a. i./ha or less, 1000 g a. i./ha or less, 950 g a. i./ha or less, 900 g a. i./ha or less, 850 g a. i./ha or less, 800 g a. i./ha or less, 750 g a. i./ha or less, 700 g a. i./ha or less, 650 g a. i./ha or less, 600 g a.

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

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

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

i./ha or less, 250 g a. i./ha or less, 240 g a. i./ha or less, 220 g a. i./ha or less, 200 g a.

i./ha or less, 190 g a. i./ha or less, 180 g a. i./ha or less, 170 g a. i./ha or less, 160 g a.

i./ha or less, 150 g a. i./ha or less, 140 g a. i./ha or less, 130 g a. i./ha or less, 120 g a.

i./ha or less, 110 g a. i./ha or less, 100 g a. i./ha or less, 95 g a. i./ha or less, 90 g a. i./ha or less, 85 g a. i./ha or less, 80 g a. i./ha or less, 75 g a. i./ha or less, 70 g a. i./ha

- 6 045740 or less, 65 g a. i./ha or less, 60 g a. i./ha or less, 55 g a. i./ha or less, 50 g a. i./ha or less, 45 g a. i./ha or less, 44 g a. i./ha or less, 43 g a. i./ha or less, 42 g a. i./ha or less, 41 g a. i./ha or less, 40 g a. i./ha or less, 39 g a. i./ha or less, 38 g a. i./ha or less, 37 g a. i./ha or less, 36 g a. i./ha or less, 35 g a. i./ha or less, 34 g a. i./ha or less, 33 g a. i./ha or less, 32 g a. i./ha or less, 31 g a. i./ha or less, 30 g a. i./ha or less, 29 g a. i./ha or less, 28 g a. i./ha or less, 27 g a. i./ha or less, 26 g a. i./ha or less, 25 g a. i./ha or less, 24 g a. i./ha or less, 23 g a. i./ha or less, 22 g a. i./ha or less, 21 g a. i./ha or less, 20 g a. i./ha or less, 19 g a. i./ha or less, 18 g a. i./ha or less, 17 g a. i./ha or less, 16 g a. i./ha or less, 15 g a. i./ha or less, 14 g a. i./ha or less, 13 g a. i./ha or less, 12 g a. i./ha or less, 11 g a. i./ha or less, 10 g a. i./ha or less, 9 g a. i./ha or less, 8 g a. i./ha or less, 7 g a. i./ha or less, 6 g a. i./ha or less, 5 g a. i./ha or less, 4 g a. i./ha or less, 3.5 g a. i./ha or less, 3 g a. i./ha or less, 2.5 g a. i./ha or less, 2 g a. i./ha or less, 1.75 g a. i./ha or less, 1.5 g a. i./ha or less, 1.25 g a. i./ha or less or 1.1 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 1-4500 g a. i./ha, 4-3900 g a. i./ha, 1.75-2500 g a. i./ha, 75-3100 g a. i./ha, 90-900 g a. i./ha, 55-4200 g a. i./ha, 50-2350 g a. i./ha, 80-2900 g a. i./ha, 120-4100 g a. i./ha, 65-2700 g a. i./ha, 300-4000 g a. i./ha, 1200-3600 g a. i./ha, 250-2000 g a. i./ha, 1.75-250 g a. i./ha, 7004250 g a. i./ha, 39-1100 g a. i./ha or 1.1-4450 g a. i./ha.

In some aspects, the herbicidal composition contains a herbicidal effective amount of (a) a pyridine carboxylate herbicide or agriculturally acceptable salts thereof and (b) benzobicyclone, benzophenap, bicyclopyrone, fenquinotrione, isoxachlortol, isoxaflutole, lancotrione, mesotrione, pyrasulfotole, pyrazolinate, pyrazoxyphene , sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramesone, agriculturally acceptable salts or esters thereof, or combinations thereof.

Benzobicyclone.

In some aspects, the HPPD inhibitor herbicide may comprise a benzobicyclone or an agriculturally acceptable salt or ester thereof. The benzobicyclone shown below is 3-[2-chloro-4-(methylsulfonyl)benzoyl]-4(phenylthio)bicyclo[3.2.1]oct-3-en-2-one. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of benzobicyclone include its use for pre-emergence and early post-emergence control of annual and perennial paddy weeds in seed-seeded rice and seedbed rice.

The benzobicyclone 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, benzobicyclone is applied to vegetation or an area adjacent to vegetation, or applied to soil or water to prevent the emergence or growth of vegetation in an amount of 50 g a. i./ha or more, such as 55 g a. i./ha or more, 60 g a. i./ha or more, 65 g a. i./ha or more, 70 g a. i./ha or more, 75 g a. i./ha or more, 80 g a. i./ha or more, 85 g a. i./ha or more, 90 g a. i./ha or more, 100 g a. i./ha or more, 110 g a. i./ha or more, 120 g a. i./ha or more, 130 g a. i./ha or more, 140 g a. i./ha or more, 150 g a. i./ha or more, 160 g a. i./ha or more, 170 g a. i./ha or more, 180 g a. i./ha or more, 190 g a. i./ha or more, 200 g a. i./ha or more, 220 g a. i./ha or more, 240 g a. i./ha or more, 260 g a. i./ha or more, 280 g a. i./ha or more, 300 g a. i./ha or more, 320 g a. i./ha or more, 340 g a. i./ha or more, 360 g a. i./ha or more, 380 g a. i./ha or more or 400 g a. i./ha or more; in the amount of 401 g a. i./ha or less, such as 400 g a. i./ha or less, 380 g a. i./ha or less, 360 g a. i./ha or less, 340 g a. i./ha or less, 320 g a. i./ha or less, 300 g a. i./ha or less, 280 g a. i./ha or less, 260 g a. i./ha or less, 240 g a. i./ha or less, 220 g a. i./ha or less, 200 g a. i./ha or less, 190 g a. i./ha or less, 180 g a. i./ha or less, 170 g a. i./ha or less, 160 g a. i./ha or less, 150 g a. i./ha or less, 140 g a. i./ha or less, 130 g a. i./ha or less, 120 g a. i./ha or less, 110 g a. i./ha or less, 100 g a. i./ha or less, 90 g a. i./ha or less, 85 g a. i./ha or less, 80 g a. i./ha or less, 75 g a. i./ha or less, 70 g a. i./ha or less, 65 g a. i./ha or less, 60 g a. i./ha or less, 55 g a. i./ha or less or 50 g a. i./ha or

- 7 045740 less; or in an amount ranging from any of the minimum values described above to any of the maximum values described above, such as 50-401 g a. i./ha, 75-360 g

A. i./ha, 100-240 g a. i./ha, 150-300 g a. i./ha, 170-280 g a. i./ha, 140-360 g a. i./ha, 200-320 g a. i./ha, 80-260 g

A. i./ha or 55-400 g a. i./ha.

Benzophenap.

In some aspects, the HPPD inhibitor herbicide may comprise benzophenap or an agriculturally acceptable salt or ester thereof. Benzophenap, shown below, is 2-[[4-(2,4-dichloro-3-methylbenzoyl)-1,3-dimethyl-1H-pyrazol5-yl]oxy]-1-(4-methylphenyl)ethanone. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Illustrative uses of benzophenap include its use for the control of broadleaf weeds in rice.

Benzophenap 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, benzophenap 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, 340 g a. i./ha or more, 360 g a. i./ha or more, 380 g a. i./ha or more, 400 g a. i./ha or more, 450 g a. i./ha or more, 500 g a. i./ha or more, 550 g a. i./ha or more, 600 g a. i./ha or more, 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, 725 g a. i./ha or more, 750 g a. i./ha or more, 775 g a. i./ha or more, 800 g a. i./ha or more, 825 g a. i./ha or more, 850 g a. i./ha or more, 875 g a. i./ha or more, 900 g a. i./ha or more, 925 g a. i./ha or more, 950 g a. i./ha or more, 975 g a. i./ha or more or 1000 g a. i./ha or more; in the amount of 1001 g a. i./ha or less, such as 1000 g a. i./ha or less, 975 g a. i./ha or less, 950 g a. i./ha or less, 925 g a. i./ha or less, 900 g a.

i./ha or less, 875 g a. i./ha or less, 850 g a. i./ha or less, 825 g a. i./ha or less, 800 ha.

i./ha or less, 775 g a. i./ha or less, 750 g a. i./ha or less, 725 g a. i./ha or less, 700 ha.

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 ha.

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 ha.

i./ha or less, 475 g a. i./ha or less, 450 g a. i./ha or less, 425 g a. i./ha or less, 400 ha.

i./ha or less, 380 g a. i./ha or less, 360 g a. i./ha or less, 340 g a. i./ha or less, 320 ha.

i./ha or less or 310 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 300-1001 g a. i./ha, 450-1000 g a. i./ha, 380-825 g a. i./ha, 400-900 g a. i./ha, 450-925 g a. i./ha, 550-775 g a. i./ha, 600-850 g a. i./ha, 475-950 g a. i./ha, 340-925 g a. i./ha, 650-975 g a. i./ha, 725-1000 g a. i./ha, 450-850 g a. i./ha, 800-950 g a. i./ha or 310-975 g a. i./ha.

Bicyclopyrone.

In some aspects, the HPPD inhibitor herbicide may comprise bicyclopyrone or an agriculturally acceptable salt or ester thereof. Bicyclopyrone shown below is 4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6(trifluoromethyl)-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-ene-2 -He. Its herbicidal activity is described in The Pesticide Manual, Seventeenth Edition, 2016. Exemplary uses of bicyclopyrone include its use for pre-emergence and early post-emergence control of broadleaf and grass weeds in maize and cereal crops.

- 8 045740

Bicyclopyrone 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, bicyclopyrone 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 20 g a. i./ha or more, such as 25 g a. i./ha or more, 30 g a. i./ha or more, 35 g a. i./ha or more, 40 g a. i./ha or more, 45 g a. i./ha or more, 50 g a. i./ha or more, 55 g a. i./ha or more, 60 g a. i./ha or more, 65 g a. i./ha or more, 70 g a. i./ha or more, 75 g a. i./ha or more, 80 g a. i./ha or more, 85 g a. i./ha or more, 90 g a. i./ha or more, 100 g a. i./ha or more, 110 g a. i./ha or more, 120 g a. i./ha or more, 130 g a.

i./ha or more, 140 g a. i./ha or more, 150 g a. i./ha or more, 160 g a. i./ha or more, 170 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, 220 ha.

i./ha or more, 240 g a. i./ha or more, 260 g a. i./ha or more, 280 g a. i./ha or more, 300 ha.

i./ha or more, 320 g a. i./ha or more, 340 g a. i./ha or more, 360 g a. i./ha or more, 380 ha.

i./ha or more or 400 g a. i./ha; in the amount of 401 g a. i./ha or less, such as 400 g a. i./ha or less, 380 g a. i./ha or less, 360 g a. i./ha or less, 340 g a. i./ha or less, 320 g a. i./ha or less, 300 g a. i./ha or less, 280 g a. i./ha or less, 260 g a. i./ha or less, 240 g a. i./ha or less, 220 g a. i./ha or less, 200 g a. i./ha or less, 190 g a. i./ha or less, 180 g a. i./ha or less, 170 g a. i./ha or less, 160 g a. i./ha or less, 150 g a. i./ha or less, 140 g a. i./ha or less, 130 g a. i./ha or less, 120 g a. i./ha or less, 110 g a. i./ha or less, 100 g a. i./ha or less, 90 g a. i./ha or less, 85 g a. i./ha or less, 80 g a. i./ha or less, 75 g a. i./ha or less, 70 g a. i./ha or less, 65 g a. i./ha or less, 60 g a. i./ha or less, 55 g a. i./ha or less, 50 g a. i./ha or less, 45 g a. i./ha or less, 40 g a. i./ha or less, 35 g a. i./ha or less, 30 g a. i./ha or less, 25 g a. i./ha or less or 20 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 20-401 g a. i./ha, 30-260 g a. i./ha, 40-380 g a. i./ha, 55-300 g a. i./ha, 60-340 g a. i./ha, 45-320 g a. i./ha, 25-300 g a. i./ha, 100-190 g a. i./ha, 200-380 g a. i./ha, 50-200 g a. i./ha, 30-300 g a. i./ha, 85-220 g a. i./ha, 30-65 g a. i./ha or 25-400 g a. i./ha.

Fenquinotrion.

In some aspects, the HPPD inhibitor herbicide may comprise a phenquinotrione or an agriculturally acceptable salt or ester thereof. Phenquinotrione shown below is 2-[[8-chloro-3,4-dihydro-4-(4-methoxyphenyl)-3-oxo-2quinoxalinyl]carbonyl]-1,3-cyclohexanedione. Phenquinotrione is an herbicide being developed for use on rice, according to the online version of The Pesticide Manual.

Isoxachlortol.

In some aspects, the HPPD inhibitor herbicide may comprise isoxachlortol or an agriculturally acceptable salt or ester thereof. Isoxachlortol, shown below, is [4-chloro-2-(methylsulfonyl)phenyl](5-cyclopropyl-4isoxazolyl)methanone. According to the online version of The Pesticide Manual, isoxachlorthol is a herbicide whose effectiveness has been studied by Rhone-Poulenc.

Isoxaflutol.

In some aspects, the HPPD inhibitor herbicide may comprise isoxaflutole or an agriculturally acceptable salt or ester thereof. Isoxaflutole, shown below, is (5-cyclopropyl-4-isoxazolyl)[2-(methylsulfonyl)4-(trifluoromethyl)phenyl]methanone. Its herbicidal activity is described in The Pesticide Manual. Exemplary uses of isoxaflutole include its use for pre-emergence and early post-emergence control of grass and broadleaf weeds in maize and sugarcane.

- 9 045740

Isoxaflutole 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, isoxaflutole 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 20 g a. i./ha or more, such as 25 g a. i./ha or more, 30 g a. i./ha or more, 35 g a. i./ha or more, 40 g a. i./ha or more, 45 g a. i./ha or more, 50 g a. i./ha or more, 55 g a. i./ha or more, 60 g a. i./ha or more, 65 g a. i./ha or more, 70 g a. i./ha or more, 75 g a. i./ha or more, 80 g a. i./ha or more, 85 g a. i./ha or more, 90 g a.

i./ha or more, 100 g a. i./ha or more, 110 g a. i./ha or more, 120 g a. i./ha or more, 130 ha.

i./ha or more, 140 g a. i./ha or more, 150 g a. i./ha or more, 160 g a. i./ha or more, 170 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, 220 ha.

i./ha or more, 240 g a. i./ha or more, 260 g a. i./ha or more, 280 g a. i./ha or more or 300 g a. i./ha or more; in the amount of 301 g a. i./ha or less, such as 300 g a. i./ha or less, 280 g a. i./ha or less, 260 g a. i./ha or less, 240 g a. i./ha or less, 220 g a. i./ha or less, 200 g a. i./ha or less, 190 g a. i./ha or less, 180 g a. i./ha or less, 170 g a. i./ha or less, 160 g a. i./ha or less, 150 g a. i./ha or less, 140 g a. i./ha or less, 130 g a. i./ha or less, 120 g a. i./ha or less, 110 g a. i./ha or less, 100 g a. i./ha or less, 90 g a. i./ha or less, 85 g a. i./ha or less, 80 g a. i./ha or less, 75 g a. i./ha or less, 70 g a. i./ha or less, 65 g a. i./ha or less, 60 g a. i./ha or less, 55 g a. i./ha or less, 50 g a. i./ha or less, 45 g a. i./ha or less, 40 g a. i./ha or less, 35 g a. i./ha or less, 30 g a. i./ha or less or 25 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 20-301 g a. i./ha, 30-300 g a. i./ha, 40-170 g a. i./ha, 25-260 g a. i./ha, 60-120 g a. i./ha, 70-190 g a. i./ha, 75-240 g a. i./ha, 35-200 g a. i./ha, 65-220 g a. i./ha, 85-140 g a. i./ha, 100-300 g a. i./ha, 150-280 g a. i./ha, 200-301 g a. i./ha, 130-200 g a. i./ha, 25-100 g a. i./ha, 70-90 g a. i./ha or 25-300 g a. i./ha.

Lancotrione.

In some aspects, the HPPD inhibitor herbicide may comprise lancotrione or an agriculturally acceptable salt or ester thereof. Lancotrione shown below is 2-[2-chloro-3-[2-(1,3-dioxolan-2-yl)ethoxy]-4(methylsulfonyl)benzoyl]-3-hydroxy-2-cyclohexene-1- He. Lancotrione is a herbicide currently under development by Ishihara Sangyo Kaisha, Ltd., according to the online version of The Pesticide Manual.

Cl O O

Mesotrione.

In some aspects, the HPPD inhibitor herbicide may comprise mesotrione or an agriculturally acceptable salt or ester thereof. Mesotrione, shown below, is 2-[4-(methylsulfonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione. Its herbicidal activity is described in The Pesticide Manual. Exemplary uses of mesotrione include its use for pre-emergence or early post-emergence control of broadleaf weeds and certain grassy weeds in maize.

o o no ₂

Mesotrione 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

- 10 045740 In some aspects, mesotrione 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 20 g a. i./ha or more, such as 25 g a. i./ha or more, 30 g a. i./ha or more, 35 g a. i./ha or more, 40 g a. i./ha or more, 45 g a. i./ha or more, 50 g a. i./ha or more, 55 g a. i./ha or more, 60 g a. i./ha or more, 65 g a. i./ha or more, 70 g a. i./ha or more, 75 g a. i./ha or more, 80 g a. i./ha or more, 85 g a. i./ha or more, 90 g a. i./ha or more, 100 g a. i./ha or more, 110 g a. i./ha or more, 120 g a. i./ha or more, 125 g a. i./ha or more, 130 g a. i./ha or more, 140 g a. i./ha or more, 150 g a. i./ha or more, 160 g a. i./ha or more, 170 g a. i./ha or more, 175 g a. i./ha or more, 180 g a. i./ha or more, 190 g a. i./ha or more, 200 g a. i./ha or more, 220 g a. i./ha or more, 225 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, 275 g a. i./ha or more, 280 g a. i./ha or more or 300 g a. i./ha or more; in the amount of 301 g a. i./ha or less, such as 300 g a. i./ha or less, 280 g a. i./ha or less, 275 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, 225 g a. i./ha or less, 220 g a. i./ha or less, 200 g a. i./ha or less, 190 g a. i./ha or less, 180 g a. i./ha or less, 175 ha. i./ha or less, 170 g a. i./ha or less, 160 g a. i./ha or less, 150 g a. i./ha or less, 140 g a. i./ha or less, 125 g a. i./ha or less, 130 g a. i./ha or less, 120 g a. i./ha or less, 110 g a. i./ha or less, 100 g a. i./ha or less, 90 g a. i./ha or less, 85 g a. i./ha or less, 80 g a. i./ha or less, 75 g a. i./ha or less, 70 g a. i./ha or less, 65 g a. i./ha or less, 60 g a. i./ha or less, 55 g a. i./ha or less, 50 g a. i./ha or less, 45 g a. i./ha or less, 40 g a. i./ha or less, 35 g a. i./ha or less, 30 g a. i./ha or less or 25 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 20-301 g a. i./ha, 30-275 g a. i./ha, 40-140 g a. i./ha, 50-250 g a. i./ha, 60-301 g a. i./ha, 25-280 g a. i./ha, 60-125 g a. i./ha, 70-250 g a. i./ha, 90-225 g a. i./ha, 110-220 g a. i./ha, 40-175 g a. i./ha, 65160 g a. i./ha, 70-200 g a. i./ha, 80-180 g a. i./ha, 90-250 g a. i./ha, 140-225 g a. i./ha, 110-240 g a. i./ha, 120175 g a. i./ha, 110-150 g a. i./ha, 25-85 g a. i./ha or 25-300 g a. i./ha.

Pyrasulfotol.

In some aspects, the HPPD inhibitor herbicide may comprise pyrasulfotol or an agriculturally acceptable salt or ester thereof. Pyrasulfotol, shown below, is (5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)[2(methylsulfonyl)-4-(trifluoromethyl)phenyl]methanone. Its herbicidal activity is described in The Pesticide Manual. Exemplary uses of pyrasulfotole include its use in a mixture with mefenpyr-diethyl and bromoxynil or MCPA ester for post-emergence control of broadleaf weeds in cereal crops.

Pyrasulfotol 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, pyrasulfotol 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 1 g a. i./ha or more, such as 1.1 g a. i./ha or more, 1.25 g a. i./ha or more, 1.4 g a. i./ha or more, 1.5 g a. i./ha or more, 1.6 g a.

i./ha or more, 1.75 g a. i./ha or more, 1.9 g a. i./ha or more, 2 g a. i./ha or more, 2.25 g a. i./ha or more, 2.5 g a. i./ha or more, 2.75 g a. i./ha or more, 3 g a. i./ha or more, 3.25 g a. i./ha or more, 3.5 g a. i./ha or more, 3.75 g a. i./ha or more, 4 g a. i./ha or more, 4.5 g a. i./ha or more, 5 g a. i./ha or more, 6 g a. i./ha or more, 7 g a. i./ha or more, 8 g a. i./ha or more, 9 g a. i./ha or more, 9.5 g a. i./ha or more, 10 g a. i./ha or more, 10.5 g a. i./ha or more, 11 g a. i./ha or more, 11.5 g a. i./ha or more, 12 g a. i./ha or more, 12.5 g a. i./ha or more, 13 g a.

i./ha or more, 13.5 g a. i./ha or more, 14 g a. i./ha or more, 14.5 g a. i./ha or more, 15 g a.

i./ha or more, 15.5 g a. i./ha or more, 16 g a. i./ha or more, 16.5 g a. i./ha or more, 17 g a.

i./ha or more, 17.5 g a. i./ha or more, 18 g a. i./ha or more, 18.5 g a. i./ha or more, 20 g a.

i./ha or more, 21 g a. i./ha or more, 22 g a. i./ha or more, 23 g a. i./ha or more, 24 g a. i./ha or more, 25 g a. i./ha or more, 26 g a. i./ha or more, 27 g a. i./ha or more, 28 g a. i./ha or more, 29 g a. i./ha or more, 30 g a. i./ha or more, 31 g a. i./ha or more, 32 g a. i./ha or more, 33 g a. i./ha or more, 34 g a. i./ha or more, 35 g a. i./ha or more, 36 g a. i./ha or more, 37 g a. i./ha or more, 38 g a. i./ha or more, 39 g a. i./ha or more, 40 g a. i./ha or more, 41 g a.

- 11 045740

i./ha or more, 42 g a. i./ha or more, 43 g a. i./ha or more, 44 g a. i./ha or more, 45 g a. i./ha or more or 47 g a. i./ha or more; in the amount of 50 g a. i./ha or less, such as 47 g a. i./ha or less, 45 g a. i./ha or less, 44 g a. i./ha or less, 43 g a. i./ha or less, 42 g a. i./ha or less, 41 g a. i./ha or less, 40 g a. i./ha or less, 39 g a. i./ha or less, 38 g a. i./ha or less, 37 g a. i./ha or less, 36 g a. i./ha or less, 35 g a. i./ha or less, 34 g a. i./ha or less, g a. i./ha or less, 32 g a. i./ha or less, 31 g a. i./ha or less, 30 g a. i./ha or less, 29 g a. i./ha or less, 28 g a. i./ha or less, 27 g a. i./ha or less, 26 g a. i./ha or less, 25 g a. i./ha or less, 24 g a. i./ha or less, 23 g a. i./ha or less, 22 g a. i./ha or less, 21 g a. i./ha or less, 20 g a. i./ha or less, 19 g a. i./ha or less, 18.5 g a. i./ha or less, 18 g a. i./ha or less, 17.5 g a. i./ha or less, 17 g a. i./ha or less, 16.5 g a. i./ha or less, 16 g a. i./ha or less, 15.5 g a. i./ha or less, 15 g a. i./ha or less, 14.5 g a. i./ha or less, 14 g a. i./ha or less, 13.5 g a. i./ha or less, 13 g a. i./ha or less, 12.5 g a. i./ha or less, 12 g a. i./ha or less, 11.5 g a. i./ha or less, 11 g a. i./ha or less, 10.5 g a. i./ha or less, 10 g a. i./ha or less, 9.5 g a. i./ha or less, 9 g a. i./ha or less, 8.5 g a. i./ha or less, 8 g a. i./ha or less, 7.5 g a. i./ha or less, 7 g a. i./ha or less, 6.5 g a. i./ha or less, 6 g a. i./ha or less, 5.5 g a. i./ha or less, 5 g a. i./ha or less, 4.5 g a. i./ha or less, 4 g a. i./ha or less, 3.75 g

A. i./ha or less, 3.5 g a. i./ha or less, 3.25 g a. i./ha or less, 3 g a. i./ha or less, 2.75 g a. i./ha or less, 2.5 g a. i./ha or less, 2.25 g a. i./ha or less, 2 g a. i./ha or less, 1.9 g a. i./ha or less, 1.75 g a. i./ha or less, 1.6 g a. i./ha or less, 1.5 g a. i./ha or less, 1.4 g a. i./ha or less, 1.25 g a. i./ha or less or 1.1 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 1-50 g a. i./ha, 1.4-45 g a. i./ha, 1.2-42 g a. i./ha, 2.5-35 g a. i./ha, 430 g a. i./ha, 6.5-29 g a. i./ha, 1.25-24 g a. i./ha, 3.75-18.5 g a. i./ha, 2.5-38 g a. i./ha, 11-17 g a. i./ha, 8-16 g a. i./ha, 2.75-19 g a. i./ha, 3-25 g a. i./ha, 7-23 g a. i./ha, 3.5-16 g a. i./ha, 10-41 g a. i./ha, 25-50 g a. i./ha, 14-44 g a. i./ha, 35-45 g a. i./ha, 40-51 g a. i./ha or 1.1-47 g a. i./ha.

Pyrazolinate.

In some aspects, the HPPD inhibitor herbicide may comprise a pyrazolinate or an agriculturally acceptable salt or ester thereof. The pyrazolinate shown below is (2,4-dichlorophenyl)[1,3-dimethyl-5-[[(4methylphenyl)sulfonyl]oxy]-1H-pyrazol-4-yl]methanone. Its herbicidal activity is described in The Pesticide Manual. Exemplary uses of pyrazolinate include its use for the control of grasses, sedge species, Potamogeton distinctus, Sagittaria pygmaea, Sagittaria trifolia and Alisma canaliculatum in rice fields.

Pyrazolinate 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, pyrazolinate 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 225 g a. i./ha or more, 250 g a. i./ha or more, 275 g a. i./ha or more, 300 g a. i./ha or more, 350 g a. i./ha or more, 400 g a. i./ha or more, 450 g a. i./ha or more, 500 g a. i./ha or more, 550 g a. i./ha or more, 600 g a. i./ha or more, 650 g a. i./ha or more, 700 g a. i./ha or more, 750 g a. i./ha or more, 800 g a. i./ha or more, 850 g a. i./ha or more, 900 g a. i./ha or more, 950 g a. i./ha or more, 1000 g a. i./ha or more, 1050 g a. i./ha or more, 1100 g a. i./ha or more, 1200 g a. i./ha or more, 1400 g a. i./ha or more, 1600 g a. i./ha or more, 1800 g a. i./ha or more, 2000 g a. i./ha or more, 2200 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, 2800 g a. i./ha or more, 3000 g a. i./ha or more, 3200 g a. i./ha or more, 3400 g a. i./ha or more, 3500 g a. i./ha or more, 3600 g a. i./ha or more, 3800 g a. i./ha or more, 4000 g a. i./ha or more, 4200 g a. i./ha or more or 4400 g a. i./ha or more; in the amount of 4500 g a. i./ha or less, such as 4400 g a. i./ha or less, 4200 g a. i./ha or less, 4000 g a. i./ha or less, 3800 g a. i./ha or less, 3600 g a. i./ha or less, 3500 g a. i./ha or less, 3400 g a. i./ha or less, 3200 g a. i./ha or less, 3000 g a. i./ha or less, 2800 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, 2200 g a. i./ha or less, 2000 g a. i./ha or less, 1800 g a. i./ha or less, 1600 g a. i./ha or less, 1400 g a. i./ha or less, 1200 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

- 12 045740 less, 950 g a. i./ha or less, 900 g a. i./ha or less, 850 g a. i./ha or less, 800 g a. i./ha or less, 750 g a. i./ha or less, 700 g a. i./ha or less, 650 g a. i./ha or less, 600 g a. i./ha or less, 550 g a. i./ha or less, 500 g a. i./ha or less, 450 g a. i./ha or less, 400 g a. i./ha or less, 350 g a. i./ha or less, 300 g a. i./ha or less, 275 g a. i./ha or less, 250 g a. i./ha or less or 225 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 200-4500 g a. i./ha, 2000-4000 g a. i./ha, 400-1600 g a. i./ha, 1600-3800 g a. i./ha, 750-3000 g a. i./ha, 500-2200 g a. i./ha, 1600-2500 g a. i./ha, 250-800 g a. i./ha, 2500-3400 g a. i./ha, 1200-3500 g a. i./ha, 3501000 g a. i./ha or 225-4400 g a. i./ha.

Pyrazoxifene.

In some aspects, the HPPD inhibitor herbicide may comprise pyrazoxyphene or an agriculturally acceptable salt or ester thereof. Pyrazoxifene, shown below, is 2-[[4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5yl]oxy]-1-phenylethanone. Its herbicidal activity is described in The Pesticide Manual. Exemplary uses of pyrazoxifene include pre-emergence or early post-emergence control of annual and perennial rice field weeds in seed-seeded and seedbed rice.

Pyrazoxifene 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, pyrazoxifene 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 1100 g a. i./ha or more, 1200 g a. i./ha or more, 1400 g a. i./ha or more, 1600 g a. i./ha or more, 1800 g a. i./ha or more, 2000 g a. i./ha or more, 2200 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, 2800 g a. i./ha or more, 3000 g a. i./ha or more, 3200 g a. i./ha or more, 3400 g a. i./ha or more, 3500 g a. i./ha or more, 3600 g a. i./ha or more, 3800 g a. i./ha or more, 4000 g a. i./ha or more, 4200 g a. i./ha or more or 4400 g a. i./ha or more; in the amount of 4500 g a. i./ha or less, such as 4400 g a. i./ha or less, 4200 g a. i./ha or less, 4000 g a. i./ha or less, 3800 g a. i./ha or less, 3600 g a. i./ha or less, 3500 g a. i./ha or less, 3400 g a. i./ha or less, 3200 g a. i./ha or less, 3000 g a. i./ha or less, 2800 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, 2200 g a. i./ha or less, 2000 g a. i./ha or less, 1800 g a. i./ha or less, 1600 g a. i./ha or less, 1400 g a. i./ha or less, 1200 g a. i./ha or less or 1100 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 1000-4500 g a. i./ha, 1100-4000 g a. i./ha, 1400-3600 g a. i./ha, 1200-1800 g a. i./ha, 1800-4000 g a. i./ha, 2200-4500 g a. i./ha, 1500-3200 g a. i./ha, 2000-3500 g a. i./ha, 2500-3400 g a. i./ha or 1100-4400 g a. i./ha.

Sulcotrione.

In some aspects, the HPPD inhibitor herbicide may comprise sulcotrione or an agriculturally acceptable salt or ester thereof. Sulcotrione, shown below, is 2-[2-chloro-4-(methylsulfonyl)benzoyl]-1,3cyclohexanedione. Its herbicidal activity is described in The Pesticide Manual. Exemplary uses of sulcotrione include its use for the control of broadleaf weeds and post-emergence grasses in maize and sugarcane.

O O CI

Sulcotrione 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, sulcotrione 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 20 g a. i./ha or more, such as 25 g a. i./ha or

- 13 045740 more, 30 g a. i./ha or more, 35 g a. i./ha or more, 40 g a. i./ha or more, 45 g a. i./ha or more, 50 g a. i./ha or more, 55 g a. i./ha or more, 60 g a. i./ha or more, 65 g a. i./ha or more, g a. i./ha or more, 75 g a. i./ha or more, 80 g a. i./ha or more, 85 g a. i./ha or more, 90 g a.

i./ha or more, 100 g a. i./ha or more, 110 g a. i./ha or more, 120 g a. i./ha or more, 130 g a.

i./ha or more, 140 g a. i./ha or more, 150 g a. i./ha or more, 160 g a. i./ha or more, 170 g a.

i./ha or more, 180 g a. i./ha or more, 190 g a. i./ha or more, 200 g a. i./ha or more, 220 ha.

i./ha or more, 240 g a. i./ha or more, 260 g a. i./ha or more, 280 g a. i./ha or more, 300 ha.

i./ha or more, 320 g a. i./ha or more, 340 g a. i./ha or more, 360 g a. i./ha or more, 380 ha.

i./ha or more, 400 g a. i./ha or more, 420 g a. i./ha or more, 440 g a. i./ha or more, 460 ha.

i./ha or more, 480 g a. i./ha or more, 500 g a. i./ha or more, 520 g a. i./ha or more, 540 ha.

i./ha or more, 560 g a. i./ha or more or 580 g a. i./ha or more; in the amount of 600 g a. i./ha or less, such as 580 g a. i./ha or less, 560 g a. i./ha or less, 540 g a. i./ha or less, 520 g a. i./ha or less, 500 g a. i./ha or less, 480 g a. i./ha or less, 460 g a. i./ha or less,

440 g a. i./ha or less, 420 g a. i./ha or less, 400 g a. i./ha or less, 380 g a. i./ha or less,

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

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

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

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

120 g a. i./ha or less, 110 g a. i./ha or less, 100 g a. i./ha or less, 90 g a. i./ha or less, 85 g a. i./ha or less, 80 g a. i./ha or less, 75 g a. i./ha or less, 70 g a. i./ha or less, 65 g a. i./ha or less, 60 g a. i./ha or less, 55 g a. i./ha or less, 50 g a. i./ha or less, 45 g a. i./ha or less, 40 g a. i./ha or less, 35 g a. i./ha or less, 30 g a. i./ha or less or 25 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 20-600 g a. i./ha, 40400 g a. i./ha, 65-420 g a. i./ha, 120-240 g a. i./ha, 300-460 g a. i./ha, 400-580 g a. i./ha, 30-500 g a. i./ha, 250560 g a. i./ha, 250-440 g a. i./ha, 75-520 g a. i./ha, 35-300 g a. i./ha, 90-540 g a. i./ha, 150-400 g a. i./ha, 400560 g a. i./ha, 50-300 g a. i./ha, 110-480 g a. i./ha, 75-420 g a. i./ha, 65-360 g a. i./ha, 170-300 g a. i./ha, 200300 g a. i./ha, 220-600 g a. i./ha or 25-580 g a. i./g a.

Tefuryltrione.

In some aspects, the HPPD inhibitor herbicide may comprise tefuryltrione or an agriculturally acceptable salt or ester thereof. Tefuryltrione, shown below, is 2-[2-chloro-4-(methylsulfonyl)-3-[[(tetrahydro-2furanyl)-methoxy]-methyl]-benzoyl]-1,3-cyclohexanedione. Tefuryltrione is a herbicide jointly developed by Bayer CropScience, Hokko Chemical and Zen-Noh for pre- and post-emergence control of annual and perennial broadleaf weeds in rice and cereal crops, according to The Pesticide Manual online. CI O O

Tembotrion

In some aspects, the HPPD inhibitor herbicide may comprise tembotrione or an agriculturally acceptable salt or ester thereof. Tembotrione, shown below, is 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2trifluoroethoxy)methyl]benzoyl]-1,3-cyclohexanedione. Its herbicidal activity is described in The Pesticide Manual. Exemplary uses of tembotrione include its use for post-emergence control of grass and broadleaf weed species in maize.

Tembotrione can be applied to vegetation or an area adjacent 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, tembotrione 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 1 g a. i./ha or more, such as 1.1 g a. i./ha or more, 1.25 g a. i./ha or more, 1.4 g a. i./ha or more, 1.5 g a. i./ha or more, 1.6 g a. i./ha or more,

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1.75 g a. i./ha or more, 1.9 g a. i./ha or more, 2 g a. i./ha or more, 2.25 g a. i./ha or more, 2.5 g

A. i./ha or more, 2.75 g a. i./ha or more, 3 g a. i./ha or more, 3.25 g a. i./ha or more, 3.5 g a. i./ha or more, 3.75 g a. i./ha or more, 4 g a. i./ha or more, 4.5 g a. i./ha or more, 5 g a. i./ha or more, 6 g a. i./ha or more, 7 g a. i./ha or more, 8 g a. i./ha or more, 9 g a. i./ha or more,

9.5 g a. i./ha or more, 10 g a. i./ha or more, 10.5 g a. i./ha or more, 11 g a. i./ha or more, 11.5 g a. i./ha or more, 12 g a. i./ha or more, 12.5 g a. i./ha or more, 13 g a. i./ha or more,

13.5 g a. i./ha or more, 14 g a. i./ha or more, 14.5 g a. i./ha or more, 15 g a. i./ha or more,

15.5 g a. i./ha or more, 16 g a. i./ha or more, 16.5 g a. i./ha or more, 17 g a. i./ha or more,

17.5 g a. i./ha or more, 18 g a. i./ha or more, 18.5 g a. i./ha or more, 20 g a. i./ha or more, 25 g

A. i./ha or more, 30 g a. i./ha or more, 35 g a. i./ha or more, 40 g a. i./ha or more, 45 g a. i./ha or more, 50 g a. i./ha or more, 55 g a. i./ha or more, 60 g a. i./ha or more, 65 g a. i./ha or more, 70 g a. i./ha or more, 75 g a. i./ha or more, 80 g a. i./ha or more, 85 g a. i./ha or more, 90 g a. i./ha or more, 95 g a. i./ha or more, 100 g a. i./ha or more, 110 g a. i./ha or more,

120 g a. i./ha or more, 130 g a. i./ha or more, 140 g a. i./ha or more, 150 g a. i./ha or more, 160 g a. i./ha or more, 170 g a. i./ha or more, 180 g a. i./ha or more, 190 g a. i./ha or more or 200 g a. i./ha or more; in the amount of 200 g a. i./ha or less, such as 190 g a. i./ha or less, 180 g a. i./ha or less, 170 g a. i./ha or less, 160 g a. i./ha or less, 150 g a. i./ha or less, 140 g a. i./ha or less, 130 g a. i./ha or less, 120 g a. i./ha or less, 110 g a. i./ha or less, 100 g a. i./ha or less, 95 g a. i./ha or less, 90 g a. i./ha or less, 85 g a. i./ha or less, 80 g a. i./ha or less, 75 g a. i./ha or less, 70 g a. i./ha or less, 65 g a. i./ha or less, 60 g a. i./ha or less, 55 g a. i./ha or less, 50 g a. i./ha or less, 45 g a. i./ha or less, g a. i./ha or less, 35 g a. i./ha or less, 30 g a. i./ha or less, 25 g a. i./ha or less, 20 g a.

i./ha or less, 19 g a. i./ha or less, 18.5 g a. i./ha or less, 18 g a. i./ha or less, 17.5 ha.

i./ha or less, 17 g a. i./ha or less, 16.5 g a. i./ha or less, 16 g a. i./ha or less, 15.5 ha.

i./ha or less, 15 g a. i./ha or less, 14.5 g a. i./ha or less, 14 g a. i./ha or less, 13.5 ha.

i./ha or less, 13 g a. i./ha or less, 12.5 g a. i./ha or less, 12 g a. i./ha or less, 11.5 ha.

i./ha or less, 11 g a. i./ha or less, 10.5 g a. i./ha or less, 10 g a. i./ha or less, 9.5 g a. i./ha or less, 9 g a. i./ha or less, 8.5 g a. i./ha or less, 8 g a. i./ha or less, 7.5 g a. i./ha or less, 7 g a. i./ha or less, 6.5 g a. i./ha or less, 6 g a. i./ha or less, 5.5 g a. i./ha or less, 5 g a. i./ha or less, 4.5 g a. i./ha or less, 4 g a. i./ha or less, 3.75 g a. i./ha or less, 3.5 g a. i./ha or less, 3.25 g a. i./ha or less, 3 g a. i./ha or less, 2.75 g a. i./ha or less, 2.5 g a. i./ha or less, 2.25 g a. i./ha or less, 2 g a. i./ha or less, 1.9 g a. i./ha or less, 1.75 g a. i./ha or less, 1.6 g a. i./ha or less, 1.5 g a. i./ha or less, 1.4 g a. i./ha or less, 1.25 g a. i./ha or less or 1.1 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 1-200 g a. i./ha, 1.4-75 g a. i./ha, 3.5-150 g a. i./ha, 10-140 g a. i./ha, 6-75 g a. i./ha, 8180 g a. i./ha, 1.5-25 g a. i./ha, 2.5-15 g a. i./ha, 2.25-10 g a. i./ha, 25-120 g a. i./ha, 1.9-130 g a. i./ha, 20-40 g a. i./ha, 30-180 g a. i./ha, 45-190 g a. i./ha, 3.5-70 g a. i./ha, 6-130 g a. i./ha, 70-90 g a. i./ha, 15-110 g a. i./ha, 120-140 g a. i./ha or 1.1-190 g a. i./g a.

Tolpiralate.

In some aspects, the HPPD inhibitor herbicide may comprise tolpyralate or an agriculturally acceptable salt or ester thereof. Tolpiralate shown below is 1-[[1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl]oxy]ethyl methyl carbonate . According to the online version of The Pesticide Manual, tefuryltrione is a herbicide developed by Ishihara Sangyo Kaisha Ltd. for pre- and post-emergence control of broadleaf and grass weeds, including Palmer amaranth, hemp grass, ragweed and Faber bristleweed, in maize.

Topramezon.

In some aspects, the HPPD inhibitor herbicide may comprise topramesone or an agriculturally acceptable salt or ester thereof. Topramesone shown below is [3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone . Its herbicidal activity is described in The Pesticide Manual. Exemplary uses of topramesone include its use for post-emergence weed control in maize.

- 15 045740

Topramesone 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, topramesone 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 1 g a. i./ha or more, such as 1.1 g a. i./ha or more, 1.25 g a. i./ha or more, 1.4 g a. i./ha or more, 1.5 g a. i./ha or more, 1.6 g a. i./ha or more, 1.75 g a. i./ha or more, 1.9 g a. i./ha or more, 2 g a. i./ha or more, 2.25 g a. i./ha or more, 2.5 g a. i./ha or more, 2.75 g a. i./ha or more, 3 g a. i./ha or more, 3.25 g a. i./ha or more, 3.5 g a.

i./ha or more, 3.75 g a. i./ha or more, 4 g a. i./ha or more, 4.5 g a. i./ha or more, 5 g a. i./ha or more, 6 g a. i./ha or more, 7 g a. i./ha or more, 8 g a. i./ha or more, 9 g a. i./ha or more,

9.5 g a. i./ha or more, 10 g a. i./ha or more, 10.5 g a. i./ha or more, 11 g a. i./ha or more, 11.5 g a. i./ha or more, 12 g a. i./ha or more, 12.5 g a. i./ha or more, 13 g a. i./ha or more,

13.5 g a. i./ha or more, 14 g a. i./ha or more, 14.5 g a. i./ha or more, 15 g a. i./ha or more,

15.5 g a. i./ha or more, 16 g a. i./ha or more, 16.5 g a. i./ha or more, 17 g a. i./ha or more,

17.5 g a. i./ha or more, 18 g a. i./ha or more, 18.5 g a. i./ha or more, 20 g a. i./ha or more, 25 g

A. i./ha or more, 30 g a. i./ha or more, 35 g a. i./ha or more, 40 g a. i./ha or more, 45 g a. i./ha or more, 50 g a. i./ha or more, 55 g a. i./ha or more, 60 g a. i./ha or more, 65 g a. i./ha or more, 70 g a. i./ha or more, 75 g a. i./ha or more, 80 g a. i./ha or more, 85 g a. i./ha or more, 90 g a. i./ha or more, 95 g a. i./ha or more or 100 g a. i./ha or more; in the amount of 100 g a. i./ha or less, such as 95 g a. i./ha or less, 90 g a. i./ha or less, 85 g a. i./ha or less, 80 g a. i./ha or less, 75 g a. i./ha or less, 70 g a. i./ha or less, 65 g a. i./ha or less, 60 g a. i./ha or less, 55 g a. i./ha or less, 50 g a. i./ha or less, 45 g a. i./ha or less, 40 g a. i./ha or less, 35 g a. i./ha or less, 30 g a. i./ha or less, 25 g a. i./ha or less, 20 g a. i./ha or less, 19 g a. i./ha or less, 18.5 g a. i./ha or less, 18 g a. i./ha or less, 17.5 g a. i./ha or less, 17 g a. i./ha or less, 16.5 g a. i./ha or less, 16 g a. i./ha or less, 15.5 g a. i./ha or less, 15 g a. i./ha or less, 14.5 g a. i./ha or less, 14 g a. i./ha or less, 13.5 g a. i./ha or less, 13 g a. i./ha or less, 12.5 g a. i./ha or less, 12 g a. i./ha or less, 11.5 g a. i./ha or less, 11 g a. i./ha or less, 10.5 g a. i./ha or less, 10 g a. i./ha or less, 9.5 g a. i./ha or less, 9 g a. i./ha or less, 8.5 g a. i./ha or less, 8 g a. i./ha or less, 7.5 g a. i./ha or less, 7 g a. i./ha or less, 6.5 g a. i./ha or less, 6 g a. i./ha or less, 5.5 g a. i./ha or less, 5 g a. i./ha or less, 4.5 g a. i./ha or less, 4 g a. i./ha or less, 3.75 g a. i./ha or less, 3.5 g a. i./ha or less, 3.25 g a. i./ha or less, 3 g a. i./ha or less, 2.75 g a. i./ha or less, 2.5 g a. i./ha or less, 2.25 g a. i./ha or less, 2 g a. i./ha or less, 1.9 g a. i./ha or less, 1.75 g a. i./ha or less, 1.6 g a. i./ha or less, 1.5 g a. i./ha or less, 1.4 g a. i./ha or less, 1.25 g a. i./ha or less or 1.1 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 1-100 g a. i./ha, 2-90 g a. i./ha, 4-80 g a. i./ha, 2.5-75 g a. i./ha, 9-60 g a. i./ha, 10-55 g a. i./ha, 325 g a. i./ha, 8-15 g a. i./ha, 1.5-10 g a. i./ha, 5-80 g a. i./ha, 6.5-45 g a. i./ha, 15-85 g a. i./ha, 20-90 g a. i./ha, 2.5-40 g a. i./ha, 3-30 g a. i./ha, 9-85 g a. i./ha or 1.5-95 g a. i./g a.

IV. Compositions.

A composition comprising (a) a pyridine carboxylate herbicide or an agriculturally acceptable salt thereof may be mixed with or used in combination with (b) an HPPD inhibitor herbicide or an agriculturally acceptable salt or complex thereof. ether.

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

- 16 045740 vegetation.

In some aspects, the combined action of (a) a pyridine carboxylate herbicide or an agriculturally acceptable salt thereof and (b) an HPPD inhibitor herbicide or an agriculturally acceptable salt or ester thereof results in an unexpectedly enhanced herbicidal effect against unwanted vegetation even at lower application rates than those typically used to ensure that the herbicide itself exhibits a herbicidal effect. 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 salts thereof (in g eq/ha) and (b) the HPPD inhibitor herbicide or agriculturally acceptable salts thereof or ester (in g a.i./ha) may be 1:4500 or more, such as 1:4000 or more, 1:3500 or more, 1:3000 or more, 1:2500 or more, 1 :2000 or more, 1:1500 or more, 1:1000 or more, 1:900 or more, 1:800 or more, 1:700 or more, 1:600 or more, 1:500 or more, 1:400 or more, 1:300 or more, 1:200 or more, 1:100 or more, 1:90 or more, 1:80 or more, 1:70 or more, 1:60 or more, 1:50 or more , 1:40 or more, 1:30 or more, 1:24 or more, 1:20 or more, 1:18 or more, 1:15 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, 1:1.1 or more, 1:1 or more, 1.1:1 or more, 1.2:1 or more, 1.3:1 or more, 1 ,4:1 or more, 1.5:1 or more, 1.6:1 or more, 1.7:1 or more, 1.8:1 or more, 1.9:1 or more, 2:1 or more, 3:1 or more, 4:1 or more, 5:1 or more, 6:1 or more, 7:1 or more, 8:1 or more, 9:1 or more, 10:1 or more , 15:1 or greater, 20:1 or greater, 22:1 or greater, 24:1 or greater, 25:1 or greater, 26:1 or greater, 28:1 or greater, 30:1 or greater, 35 :1 or more, 40:1 or more, 45:1 or more, 50:1 or more, or 55:1 or more; the weight ratio of (a) and (b) may be 300:1 or less, such as 250:1 or less, 200:1 or less, 150:1 or less, 125:1 or less, 100:1 or less , 90:1 or less, 80:1 or less, 70:1 or less, 60:1 or less, 50:1 or less, 40:1 or less, 30:1 or less, 20:1 or less, 10 :1 or less, 9:1 or less, 8:1 or less, 7:1 or less, 6:1 or less, 5:1 or less, 4:1 or less, 3:1 or less, 2:1 or less, 1.9:1 or less, 1.8:1 or less, 1.7:1 or less, 1.6:1 or less, 1.5:1 or less, 1.4:1 or less , 1.3:1 or less, 1.2:1 or less, 1.1:1 or less, 1:1 or less, 1:1.1 or less, 1:1.2 or less, 1:1 .3 or less, 1:1.4 or less, 1:1.5 or less, 1:1.6 or less, 1:1.7 or less, 1:1.8 or less, 1:1.9 or less, 1:2 or less, 1:3 or less, 1:4 or less, 1:5 or less, 1:6 or less, 1:7 or less, 1:8 or less, 1:9 or less , 1:10 or less, 1:20 or less, 1:30 or less, 1:40 or less, 1:50 or less, 1:60 or less, 1:70 or less, 1:80 or less, 1 :90 or less, 1:100 or less, 1:200 or less, 1:300 or less, 1:400 or less, 1:500 or less, 1:1000 or less, 1:1500 or less, 1:2000 or less, 1:2500 or less, 1:3000 or less, 1:3500 or less, or 1:4000 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 1:4500 to 300:1, 1:700 to 6: 1, 1:40 to 90:1, 1:10 to 16:1, 1:14 to 10:1, 1:8 to 1:6 or 1:5 to 5:1.

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

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 agriculturally acceptable salts thereof.

2. Excipients.

- 17 045740

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, oil adjuvants, adhesives (for example for use in seed treatment formulations), surfactants, protective colloids, emulsifiers, tackifiers and mixtures thereof .

Exemplary agriculturally acceptable adjuvants include, but are not limited to, oil adjuvant 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 -Spalkyl polyglycoside; phosphoric acid and alcohol ethoxylates; natural primary ethoxylate (C ₁₂ -C ₁₆ ); di-sec-butylphenol block copolymer EO-PO; methyl-terminated polysiloxane; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oils; tridecyl alcohol (synthetic) ethoxylates (e.g. 8 EO); tallow amine ethoxylates (e.g. 15 EO) and PEG(400) dioleate-99.

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

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

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

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

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

Exemplary colorants include, but are not limited to, the dyes known as Rhodamine B, Pigment Blue 15:4, Pigment Blue 15:3, Pigment Blue 15:2, Pigment Blue 15:1, Pigment Blue 80, Pigment Yellow 1, Pigment Yellow 13, red pigment 112, red pigment 48:2, red pigment 48:1, red pigment 57:1, red pigment 53:1, orange pigment 43, orange pigment 34, orange pigment 5, green pigment 36, green pigment 7, white pigment 6, brown pigment 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108 and mixtures thereof.

Exemplary adhesives include, but are not limited to, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, tylose, and mixtures thereof.

3. Antidotes.

In some aspects, the additive is an antidote. Antidotes are compounds that lead to better compatibility of the crop plant 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 the crop plant from damage that might otherwise occur due to application of the herbicide. Illustrative antidotes include, but are not limited to, AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintoset, cloquintoset-mexil, ciometrinil, cyprosulfa

- 18 045740 mid, daimuron, dichlormide, dicyclonone, dietolate, dimepiperate, disulfoton, fenchlorazole, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, tsecaowan, jiecaosi, mefenpyr, mefenpyr-di ethyl, 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 derivatives. In some aspects, the antidote may be cloquintoset or an ester or salt thereof, such as cloquintoset-mexil. In some aspects, the antidote may be mefenpyr or an ester or salt thereof, such as mefenpyr diethyl. In some aspects, the antidote is applied to rice, cereal or maize. For example, mefenpyr 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, N-methyl-2-pyrrolidinone; N,Ndimethylalkylamides, dimethyl sulfoxide and liquid fertilizers, as well as mixtures thereof. Exemplary solid carriers include, but are not limited to, forms of silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, particulate synthetics, pyrophyllite clay , attapulgite clay, diatomaceous earth, calcium carbonate, bentonite clay, fuller's earth, cotton seed husk, wheat flour, soybean flour, pumice, wood flour, walnut flour, lignin, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, wholemeal flour grinding, tree bark flour, wood and nut shell flour, cellulose-based powders and mixtures thereof.

B. Physical condition.

In some aspects, a formulation of (a) a pyridine carboxylate herbicide or an agriculturally acceptable salt thereof and (b) an HPPD inhibitor herbicide or an agriculturally acceptable salt or ester thereof may be 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) and (b) may be provided in the form of a concentrated formulation, such as a concentrate. In some aspects, the concentrate is stable and remains effective during storage and transportation. In various aspects, the concentrate is a clear, homogeneous liquid that is stable at temperatures of 54°C or higher. In some aspects, the concentrate does not exhibit any precipitation of solids at temperatures of -10°C or higher. In some aspects, the concentrate does not exhibit separation, precipitation, or crystallization of any of the components at low temperatures. For example, the concentrate remains a clear solution at temperatures below 0°C (eg, below -5°C, below -10°C, below -15°C). In some aspects, the concentrate has a viscosity of less than 50 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 total concentrations of as little as about 1 wt.%, about 2.5 wt.%, about 5 wt.%, about 7.5 wt.%, about 10 wt. %, about 15 wt.%, about 20 wt.%, about 25 wt.%, about 30 wt.%, about 35 wt.%, about 40 wt.%, about 45 wt.%, to about 50 wt.%, about 55 wt.%, about 60 wt.%, about 65 wt.%, about 70 wt.%, about 75 wt.%, about 80 wt.%, about 85 wt.%, about 90 wt.%, about 95 wt.%, about 97 wt.%, or within any range defined by any two of the above values, for example from about 1 wt.% to about 97 wt.%, from about 10 wt.% to about 90 wt.%, from from about 20 wt.% to about 45 wt.% and from about 25 wt.% to about 50 wt.% based on the total weight of the composition. Before use, concentrates may be diluted with an inert carrier such as water. Diluted formulations applied to unwanted vegetation or the location of unwanted vegetation may contain from 0.0006 to 8.0 wt.% of the total amount of (a) and (b) (for example, from 0.001 to 5.0 wt.% ) in terms of the total weight of the diluted composition.

C. Packaging.

In some aspects, the composition may be in the form of a single package formulation containing both (a) a pyridine carboxylate herbicide or agriculturally acceptable salts thereof and (b) an HPPD inhibitor herbicide or agriculturally acceptable salts thereof. from an agricultural point of view, salt or ester. In some aspects, the composition may be in the form of a single package composition containing both (a) and (b) and further comprising 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 containing (a) and the composition containing (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 compositions described herein.

In some aspects, a method of controlling unwanted vegetation, which includes 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 and/or after the emergence of unwanted vegetation). In some aspects, the composition is applied post-emergence to unwanted vegetation. In some aspects, a pyridine carboxylate herbicide and an HPPD inhibitor herbicide are used simultaneously. In some aspects, the pyridine carboxylate herbicide and the HPPD inhibitor herbicide are applied sequentially, e.g., without delay

- 20 045740 or with a minimum delay, within approximately 10 minutes, within approximately 20 minutes, within approximately 30 minutes, within approximately 40 minutes, within approximately 1 hour, within approximately 2 hours, within approximately 4 hours, within about 8 hours, within about 16 hours, within about 24 hours, within about 2 days, or within about 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 media, 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, turfgrass, pastures, meadows, natural grasslands, fallow land, rights-of-way, water installations, trees and vineyards, natural nature reserves or natural pastures. In some aspects, control of unwanted vegetation is carried out in a row crop. Exemplary crops include, but are not limited to, wheat, barley, triticale, rye, teff, oats, maize, cotton, soybeans, sorghum, rice, millet, sugarcane, and natural pasture (eg, pasture grasses). In some aspects, the compositions and methods disclosed herein can be used to control unwanted vegetation in maize, wheat, barley, rice, sorghum, millet, oat species, or combinations thereof. In some aspects, the compositions and methods disclosed herein can be used to control unwanted vegetation in broadleaf crops. In some aspects, the compositions and methods disclosed herein can be used to control unwanted vegetation in canola, flax, sunflower, soybean, or cotton crops. 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 Conservation Reserve Program (CRP) lands, plantations, vineyards, meadows, and grasses grown for seed. In some aspects, the compositions and methods disclosed herein can be used on artificial lawns (eg, residential, industrial, and institutional), golf courses, parks, cemeteries, athletic fields, and turf farms.

The compositions and methods disclosed herein can also be applied to crop plants that are resistant to, for example, herbicides, pathogens and/or insects. In some aspects, the compositions and methods disclosed herein can be applied to crop plants that have been rendered resistant to one or more herbicides through genetic engineering or breeding. In some aspects, the compositions and methods disclosed herein can be applied to crop plants that are resistant to one or more pathogens, such as plant pathogenic fungi, due to the use of genetic engineering or breeding. In some aspects, the compositions and methods disclosed herein can be applied to crop plants that are resistant to insect attack due to genetic engineering or breeding. Exemplary resistant crops include, but are not limited to, crops that are resistant to photosystem II inhibitors, or crops that, due to the introduction of a Bacillus thuringiensis (or Bt) toxin gene by genetic modification, are resistant to attack by certain insects. In some aspects, the compositions and methods described herein can also be used in combination with glyphosate, glufosinate, dicamba, phenoxyauxins, pyridyloxyauxins, aryloxyphenoxypropionates, acetyl-CoA carboxylase (ACCase) inhibitors, imidazolinones, acetolactate synthase (ALS) inhibitors, 4 -hydroxyphenyl-pyruvate dioxygenase (HPPD), protoporphyrinogen oxidase (PPO) inhibitors, triazines and bromoxynil for vegetation control in crops with tolerance to glyphosate, glufosinate, dicamba, phenoxyauxins, pyridyloxyauxins, aryloxyphenoxypropionates, ACCase inhibitors, imidazolinones, synthetic herbicides th auxin, HPPD inhibitors, PPO inhibitors, triazines, bromoxynil or combinations thereof. In some aspects, unwanted vegetation is controlled in crops with tolerance to glyphosate, glufosinate, dicamba, phenoxyauxins, pyridyloxyauxins, aryloxyphenoxypropionates, ACCase inhibitors, synthetic auxin herbicides, HPPD inhibitors, PPO inhibitors, triazines, and bromoxynil, having one or more or packaged features conferring tolerance to one or more chemicals and/or multiple mechanisms of action. In some aspects, unwanted vegetation can be controlled in a crop that is tolerant to ACCase inhibitors, 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., Cassia spp., Commelina spp., Datura spp., Euphorbia spp., Geranium spp., Galinsoga spp., Ipomea spp., Lamium spp., Lolium spp., Malva spp., Matricaria spp., Prosopis, 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 solyanka (Salsola kali), field mustard (Sinapis arvensis), Sonchus arvensis, Thlaspi arvense, Tagetes minuta, Richardia brasiliensis, Plantago major, Plantago lanceolata, Persian speedwell (Veronica persica), amaranth (Amaranthus retroflexus), rapeseed

- 22 045740 winter (Brassica napus), white pigweed (Chenopodium album), field thistle (Cirsium arvense), edible milkweed (Cyperus esculentus), variegated milkweed (Euphorbia heterophylla), wild lettuce (Lactuca serriola), purple damselfish (Lamium purpureum) , chamomile (Matricaria chamomilla), odorless chamomile (Matricaria inodora), field navel (Anthemis arvensis), buckwheat (Fagopyrum esculentum), bindweed (Polygonum convulvus), Faber bristle grass (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 (for example, amides, anilidex, furanones, phenoxybutanamides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors (for example, callistemons, isoxazolams, pyrazolams, triketones), cellulose biosynthesis inhibitors (e.g. nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes of action such as quinclorac, and unclassified herbicides such as arylaminopropionic acids, difenzoquat, endothal and organoarsenic compounds. Exemplary weeds with resistance or tolerance include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple classes of chemicals, biotypes with resistance or tolerance to multiple mechanisms of herbicidal action, and biotypes with multiple mechanisms resistance or tolerance (eg, target site resistance or metabolic resistance).

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

Examples

Greenhouse test method - assessment of post-emergence 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 of 5.2 to 6.2 and an organic content of at least 50 percent in plastic pots with a surface area of 103.2 square centimeters (cm ² ). In some aspects, fungicide and/or other chemical or physical treatments are used to ensure proper germination and healthy plants. Plants were grown for 7-36 days 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

- 23 045740 was placed in a 25 ml glass vial and diluted in 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 HPPD inhibitor herbicide) were prepared by adding weighed amounts or aliquots of the HPPD inhibitor 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 that are an HPPD inhibitor (component b) are given in ha. i./ha.

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

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

Example 1.

Compositions containing Compound A and benzobicyclone were tested on undesirable vegetation species including STEME, Stellaria media, spring rape (BRSNN, Brassica napus), Faber's bristle grass (SETFA, Setaria faberi), kochia (KCHSC, Kochia scoparia), LOLMU, Lolium multiflorum, ECHCG, Echinochloa crus-galli and DIGSA, Digitaria sanguinalis, to determine the effectiveness of the compositions against these types of unwanted vegetation.

The results are summarized in table. 1 below.

Table 1 Herbicidal effects (% visible damage) of compound A and benzobicyclone on weeds

Application rate (g/ha) Compound A 7.5 10 0 7.5 10 Benzobicyclone 0 0 50 50 50 STEM Observable 90 85 28 83 85 Expected — — — 93 89 R -10 -4 BRSNN Observable 23 45 8 43 40 Expected — — — 28 49 R 14 -9 SETFA Observable 60 78 0 70 78 Expected — — — 60 78 R 10 0

- 24 045740

KCHSC Observable 63 70 0 60 70 Expected — — — 63 70 P -3 0 LOLMU Observable 8 3 0 10 15 Expected — — — 8 3 R 3 13 ECHCG Observable 80 88 0 68 75 Expected — — — 80 88 R -13 -13 DIGSA Observable 13 25 10 33 35 Expected — — — 21 33 R AND 3

g/ha=grams per hectare.

STEME=Stellaria media (medium chickweed).

BKSNN=Brassica napus (spring rapeseed).

SETFA=Setaria faberi (Faber's bristleweed).

KCHSC=Kochia scoparia (kochia).

LOLMU=Lolium multiflorum (multifloral chaff).

ECHCG=Echinochloa crus-galli (common barnyard grass).

DIGSA=Digitaria sanguinalis (blood red crabgrass).

Example 2.

Compositions containing Compound A and isoxaflutole were tested to determine the effectiveness of the compositions against unwanted vegetation species including ABUTH, Abutilon theophrasti, POLCO, Polygonum convolvulus, thistle (CIRAR, Cirsium arvense), morning glory (IPOHE, Ipomoea hederacea), amaranth (AMARE, Amaranthus retroflexus), common sunflower (HELAN, Helianthus annuus) and kochia (KCHSC, Kochia scoparia).

The results are summarized in table. 2 below.

- 25 045740

table 2

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

Application rate Compound A 7.5 10 0 7.5 10 (g/ha) Isoxaflutole 0 0 60 60 60 VIOTR Observable 3 3 25 48 60 Expected — — — 27 27 R 21 33 ABUTH Observable 40 48 58 99 99 Expected — — — 75 78 R 24 21 POLCO Observable 68 70 0 90 88 Expected — — — 68 70 R 23 18 CIRAR Observable 25 20 70 83 84 Expected — — — 78 76 R 5 8 IPOHE Observable 5 0 38 thirty 25 Expected — — — 41 38 R -AND -13 AMARE Observable 80 85 53 98 97 Expected — — — 91 93 R 7 4 HELAN Observable 83 88 85 99 100 Expected — — — 97 98 R 1 2 KCHSC Observable 63 65 38 70 75 Expected — — — 77 78 R -7 -3

g/ha=grams per hectare.

VIOTR= Fiola tricolor (tricolor violet).

ABUTH=Abutilon theophrasti (Theophrastus' rope).

POLCO=Polygonum convolvulus (convolvulus knotweed).

CIRAR=Cirsium arvense (field thistle).

IPOHE=Ipomoea hederacea (ivy morning glory).

AMARE=Amaranthus retroflexus (amaranth).

HELAN=Helianthus annuus (common sunflower).

KCHSC=Kochia scoparia (kochia).

- 26 045740

Example 3.

Compositions containing Compound A and mesotrione were tested to determine the effectiveness of the compositions against unwanted vegetation species including VIOTR, Viola tricolor, ABUTH, Abutilon theophrasti, POLCO, Polygonum convolvulus, and spurge. (EPHHL, Euphorbia heterophylla), thistle (CIRAR, Cirsium arvense), amaranth (AMARE, Amaranthus retroflexus), common sunflower (HELAN, Helianthus annuus) and kochia (KCHSC, Kochia scoparia).

The results are summarized in table. 3 below.

Table 3 Herbicidal effects (% visible damage) of compound A and mesotrione against weeds and grain crops

Application rate (g/ha) Compound A 7.5 10 0 7.5 10 Mesotrione 0 0 35 35 35 VIOTR Observable 3 3 75 85 90 Expected — — — 76 76 R 9 14 ABUTH Observable 40 48 99 100 100 Expected — — — 99 99 R 1 1 POLCO Observable 68 70 75 80 86 Expected — — — 92 93 R -12 -7 EPHHL Observable 91 83 100 99 98 Expected — — — 100 100 R -2 -3 CIRAR Observable 25 20 84 85 88 Expected — — — 88 87 R -3 1 AMARE Observable 80 85 90 100 90 Expected — — — 2 -9 R 7 4 HELAN Observable 83 88 90 99 100 Expected — — — 98 99 R 0 1 KCHSC Observable 63 65 35 68 75 Expected — — — 76 77 R -8 -2

- 27 045740 g/ha=grams per hectare.

VIOTR=Viola tricolor (tricolor violet).

ABUTH=Abutilon theophrasti (Theophrastus' rope).

POLCO=Polygonum convolvulus (convolvulus knotweed).

EPHHL=Euphorbia heterophylla (spurge).

CTRAR=Cirsium arvense (field thistle).

AMARE=Amaranthus retroflexus (amaranth).

HELAN=Helianthus annuus (common sunflower).

KCHSC=Kochia scoparia (kochia).

Example 4.

Compositions containing Compound A and sulcotrione were tested to determine the effectiveness of the compositions against species of unwanted vegetation, including spring rape (BRSNN, Brassica napus) and kochia (KCHSC, Kochia scoparia), 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. 4 below.

Table 4 Herbicidal effects (% visible damage) of compound A and sulcotrione on weeds and grain crops

Application rate (g/ha) Compound A 7.5 10 0 7.5 10 Sulcotrione 0 0 75 75 75 BRSNN Observable 55 60 75 99 100 Expected - - - 89 90 R 10 10 KCHSC Observable 50 58 thirty 73 78 Expected - - - 65 70 R 8 7 TRZAS Observable 0 0 0 0 0 Expected - - - 0 0 R 0 0 HORVS Observable 8 0 8 10 15 Expected - - - 14 8 R -4 8

g/ha=grams per hectare.

BRSNN=Brassica napus (spring rapeseed).

KCHSC=Kochia scoparia (kochia).

TRZAS=Triticum aestivum (spring wheat).

HORVS=Hordeum vulgare (spring barley).

Example 5.

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

The results are summarized in table. 5 below.

Table 5 Herbicidal effects (% visible damage) of compound A and pyrazolinate on weeds and grain crops

Application rate (g/ha) Connection A 7.5 10 0 7.5 10 Pyrazolinate 0 0 225 225 225 AMARE Observable 90 85 10 100 93 Expected - - - 91 87 P 9 6 BRSNW Observable 35 40 0 35 45 Expected - - - 35 40 R 0 5 CHEAL Observable 75 80 5 85 85 Expected - - - 76 81 R 9 4 CIRAR Observable 40 55 0 60 63 Expected - - - 40 55 R 20 8 KCHSC Observable 70 70 0 70 78 Expected - - - 70 70 R 0 8 MATCH Observable 10 20 0 48 50 Expected - - - 10 20 R 38 thirty POLCO Observable thirty 43 5 60 65 Expected - - - 34 45 R 27 20 SASKR Observable 60 63 0 68 70

- 29 045740

Expected - - - 60 63 R 8 8 SINAR Observable 83 88 5 93 94 Expected - - - 83 88 R 9 6 TRZAS Observable 0 0 0 0 0 Expected - - - 0 0 R 0 0 HORVS Observable 0 0 0 0 0 Expected - - - 0 0 R 0 0

g/ha=grams per hectare.

AMARE=Amaranthus retrojlexus (amaranth).

BRSNW=Brassica napus (winter rapeseed).

CHEAL=Chenopodium album L. (white pigweed).

CIRAR=Cirsium arvense (Cirsium arvense)

KCHSC=Kochia scoparia (kochia).

MATCH=Matricaria chamomilla (chamomile).

POLCO=Polygonum convolvulus (convolvulus knotweed).

SASKR=Salsola kali (Russian solyanka).

SINAR=Sinapis arvensis (field mustard).

TRZAS=Triticum aestivum (spring wheat).

HORVS=Hordeum vulgare (spring barley).

Example 6.

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

The results are summarized in table. 6 below.

- 30 045740

Table 6

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

Application rate (g/ha) Connection A 7.5 10 0 7.5 10 Tembotrion 0 0 25 25 25 AMARE Observable 90 85 100 100 100 Expected - - - 100 100 P 0 0 BRSNW Observable 35 40 88 95 94 Expected - - - 92 93 R 3 1 CHEAL Observable 75 80 100 100 100 Expected - - - 100 100 R 0 0 CIRAR Observable 40 55 75 73 83 Expected - - - 85 89 R -13 -6 KCHSC Observable 70 70 48 80 83 Expected - - - 84 84 R -4 -2 MATCH Observable 10 20 73 85 88 Expected - - - 75 78 R 10 10 POLCO Observable thirty 43 25 70 83 Expected - - - 48 57 R 23 26 SASKR Observable 60 63 78 85 88 Expected - - - 91 92 R -6 -4 SINAR Observable 83 88 95 99 99 Expected - - - 99 99 R -1 -1 TRZAS Observable 0 0 20 15 15 Expected - - - 20 20 R -5 -5 HORVS Observable 0 0 10 10 10 Expected - - - 10 10 R 0 0

- 31 045740 g/ha=grams per hectare.

AMAKE=Amaranthus retroflexus (amaranth).

BRSNW=Brassica napus (winter rapeseed).

CHEAL=Chenopodium album L. (white pigweed).

CIRAR=Cirsium arvense (field thistle).

KCHSC=Kochia scoparia (kochia).

MATCH=Matricaria chamomilla (chamomile).

POLCO=Polygonum convolvulus (convolvulus knotweed).

SASKR=Salsola kali (Russian solyanka).

SINAR=Sinapis arvensis (field mustard).

TRZAS=Triticum aestivum (spring wheat).

HORVS=Hordeum vulgare (spring barley).

Example 7

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

The results are summarized in table. 7 below.

Table 7 Herbicidal effects (% visible damage) of compound A and topramesone against weeds and _____________grain crops_____________

Application rate (g/ha) Connection A 7.5 10 0 7.5 10 Topramaison 0 0 40 40 40 AMARE Observable 70 90 100 98 100 Expected - - - 100 100 R -3 0 BRSNW Observable 63 68 98 99 99 Expected - - - 99 99 R -1 -1 CHEAL Observable 70 78 100 96 98 Expected - - - 100 100 R -4 -3 CIRAR Observable 18 thirty 20 78 85 Expected - - - 34 44 R 44 41 KCHSC Observable 65 70 35 75 83 Expected - - - 77 81 R -2 2 MATCH Observable 18 thirty thirty 53 55 Expected - - - 42 51 R 10 4 POLCO Observable 60 70 43 88 88 Expected - - - 77 83

- 32 045740

R AND 5 SINAR Observable 85 88 100 100 98 Expected - - - 100 100 R 0 -z TRZAS Observable 0 0 33 33 18 Expected - - - 33 33 R 0 -15 HORVS Observable 0 0 38 45 33 Expected - - - 38 38 R 8 -5

g/ha=grams per hectare.

AMARE=Amaranthus retroflexus (amaranth).

BRSNW=Brassica napus (winter rapeseed).

CHEAL=Chenopodium album L. (white pigweed).

CIRAR=Cirsium arvense (field thistle).

KCHSC=Kochia scoparia (kochia).

MATCH=Matricaria chamomilla (chamomile).

POLCO=Polygonum convolvulus (convolvulus knotweed).

SINAR=Sinapis arvensis (field mustard).

TRZAS=Triticum aestivum (spring wheat).

HORVS=Hordeum vulgare (spring barley).

Example 8.

Compositions containing Compound B and mesotrione were tested on unwanted vegetation species including ABUTH, Abutilon theophrasti, thistle (CIRAR, Cirsium arvense) and VIOTR, Viola tricolor, to determine the effectiveness of the compositions in regarding these types of unwanted vegetation.

The results are summarized in table. 8 below.

Table 8

Herbicidal effects (% visible damage) of compound B and mesotrione on weeds

Application rate (g/ha) Connection B 7.5 10 0 7.5 10 Mesotrione 0 0 35 35 35 ABUTH Observable 68 68 85 99 100 Expected - - - 95 95 R 3 5 CIRAR Observable 45 45 73 92 93 Expected - - - 85 85 R 7 8 VIOTR Observable 10 40 78 90 90 Expected - - - 80 87 R 10 4

g/ha=grams per hectare.

ABUTH=Abutilon theophrasti (Theophrastus' rope).

CIRAR=Cirsium arvense (field thistle).

VIOTR= Viola tricolor (tricolor violet).

The compositions and methods in accordance with the attached claims are not limited in scope to the specific compositions and methods described herein, which imply

- 33 045740 are intended to illustrate several aspects of the claims, and it is intended that any compositions and methods that are functionally equivalent are 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 term comprising and its variants, when used herein, is used synonymously with the expression including and its variants, and they are open-ended, non-limiting expressions. Although the terms comprising and including are used herein to describe various aspects, the terms essentially consisting of and consisting of may be used instead of containing and including to provide more specific aspects and are also disclosed. Except in the examples and where otherwise indicated, all numbers that 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 practices, 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)

1. Herbicidal composition containing: (a) a pyridine carboxylate herbicide defined by formula (I): 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 agriculturally acceptable salts thereof; and (b) an HPPD inhibitor herbicide, or an agriculturally acceptable salt or ester thereof; and the weight ratio of the herbicide based on pyridine carboxylate in g eq. k./ha to the HPPD inhibitor herbicide, in ha. i./ha ranges from 1:500 to 50:1. 2. The composition according to claim 1, where the pyridine carboxylate-based herbicidal compound is cyanomethyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate : 3. The composition according to claim 1, where the pyridine carboxylate-based herbicidal compound is propargyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate : - 34 045740 4. The composition according to any one of claims 1 to 3, wherein the HPPD inhibitor herbicide is selected from the group consisting of benzobicyclone, benzophenap, bicyclopyrone, fenquinotrione, isoxachlortol, isoxaflutole, lancotrione, mesotrione, pyrasulfotole, pyrazolinate, pyrazoxifene, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramesone, agriculturally acceptable salts and esters thereof, and combinations thereof. 5. The composition according to any one of claims 1-4, where the weight ratio of the herbicide based on pyridine carboxylate (in g eq./ha) and the herbicide that is an HPPD inhibitor (in g a.i./ha) is from 1 :50 to 1:1. 6. Composition according to any one of claims 1-5, additionally containing an antidote. 7. Composition according to any one of paragraphs. 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 herbicidal composition containing: (a) a pyridine carboxylate herbicide defined by formula (I): NHR ² r ^3F Y^ ^{ci R} %Ak%. Vn. R ³ ' R ² , /t\ ⁿ 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 agriculturally acceptable salts thereof; and (b) an HPPD inhibitor herbicide, or an agriculturally acceptable salt or ester thereof, wherein the pyridine carboxylate herbicide is used in an amount of at least 0.1 g eq. k./ha, where the HPPD inhibitor herbicide is applied in an amount of at least 1 g a. i./ha, and wherein the weight ratio of the herbicide based on pyridine carboxylate in g eq. k./ha to the HPPD inhibitor herbicide, in g a. i./ha ranges from 1:500 to 50:1. 9. The method according to claim 8, where the pyridine carboxylate-based herbicidal compound is cyanomethyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)pyridin-2- carboxylate: 10. The method according to claim 8, wherein the pyridine carboxylate herbicidal compound is propargyl-4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate : 11. The method according to any one of claims 8 to 10, wherein the pyridine carboxylate herbicide and the HPPD inhibitor herbicide are applied simultaneously. - 35 045740 12. The method according to any one of claims 8 to 11, wherein the HPPD inhibitor herbicide is selected from the group consisting of benzobicyclone, benzophenap, bicyclopyrone, fenquinotrione, isoxachlortol, isoxaflutole, lancotrione, mesotrione, pyrasulfotole, pyrazolinate, pyrazoxifene, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramesone, agriculturally acceptable salts and esters thereof, and combinations thereof. 13. The method according to any one of claims 8-12, where the pyridine carboxylate-based herbicide is provided in an amount of 0.1 g eq. κ./ha up to 300 g eq. k./ha. 14. The method according to any one of claims 8-13, where the weight ratio of the herbicide based on pyridine carboxylate (in g eq./ha) and the herbicide that is an HPPD inhibitor (in g eq./ha) is from 1 :50 to 1:1. 15. The method according to any one of claims 8-14, additionally 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).