EA046237B1 - COMPOSITIONS CONTAINING HALAUXIFEN AND OTHER HERBICIDES, AND RELATED METHODS - Google Patents

Description

Cross reference to related applications

This application is an international application that claims priority to U.S. Provisional Patent Application No. 62/755083, filed November 2, 2018, entitled Compositions Containing Halauxifen and Other Herbicides and Related Methods, the contents of which are incorporated herein into in full by reference.

Field of technology to which the invention relates

Provided herein are herbicidal compositions containing a herbicidal effective amount of (a) halauxifen-methyl; (b) a second herbicide being 2,4-D DMA; and (c) a third glufosinate ammonium herbicide; where the weight ratio of (a), (b) and (c) is from 1:400:400 to 1:130:70.

State of the art

Protecting crops from weeds and other vegetation that inhibit crop growth is an ongoing challenge in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have created a wide variety of chemicals and chemical compounds that are effective in controlling this unwanted growth. Many types of chemical herbicides are described in the literature, and a large number are used commercially. However, there remains a need for compositions and methods that are effective in controlling unwanted vegetation.

Short description

The first embodiment provided herein includes herbicidal compositions containing a herbicidal effective amount of (a) halauxifen-methyl; (b) a second herbicide being 2,4-D DMA; and (c) a third herbicide of glufosinatammonium; where the weight ratio of (a), (b) and (c) is from 1:400:400 to 1:130:70.

The second embodiment includes the composition according to the first embodiment further comprising an agriculturally acceptable excipient or carrier.

The third embodiment includes a composition according to the first or second embodiments, wherein the weight ratio of (a), (b) and (c) is 1:130:70, 1:131:70, 1:132:70,

1:133:70, 1:134:70, 1:135:70, 1:136:70, 1:137:70, 1:138:70, 1:139:70, 1:140:70, 1: 150:70, 1:200:70, 1:130:75,

1:131:75, 1:132:75, 1:133:75, 1:134:75, 1:135:75, 1:136:75, 1:137:75, 1:138:75, 1: 139:75, 1:140:75, 1:150:75,

1:200:75, 1:130:77, 1:131:77, 1:132:77, 1:133:77, 1:134:77, 1:135:77, 1:136:77, 1: 137:77, 1:138:77, 1:139:77,

1:140:77, 1:150:77, 1:200:77 or 1:200:200.

A fourth embodiment includes a method of controlling unwanted vegetation, comprising the step of contacting a plant, where the plant is the unwanted vegetation, or a habitat thereof, soil or water, where the soil or water supports the growth of the unwanted vegetation, with a herbicidal effective amount of a combination containing ( a) galauxifen-methyl; (b) a second herbicide being 2,4-D DMA; and (c) a third herbicide being ammonium glufosinate; where the weight ratio of (a), (b) and (c) is from 1:400:400 to 1:130:70.

The fifth embodiment includes the method according to the fourth embodiment, wherein the weight ratio of (a), (b) and (c) is 1:130:70, 1:131:70, 1:132:70, 1:133:70 , 1:134:70,

1:135:70, 1:136:70, 1:137:70, 1:138:70, 1:139:70, 1:140:70, 1:150:70, 1:200:70, 1: 130:75, 1:131:75, 1:132:75,

1:133:75, 1:134:75, 1:135:75, 1:136:75, 1:137:75, 1:138:75, 1:139:75, 1:140:75, 1: 150:75, 1:200:75, 1:130:77,

1:131:77, 1:132:77, 1:133:77, 1:134:77, 1:135:77, 1:136:77, 1:137:77, 1:138:77, 1: 139:77, 1:140:77, 1:150:77,

1:200:77 or 1:200:200.

The sixth embodiment includes the method in accordance with the fourth and/or fifth embodiments, wherein control of unwanted vegetation is carried out in soil-seeded rice, water-seeded rice and seedling rice, cereal crops, wheat, barley, types of oats, rye, sorghum, corn/maize, sugar cane, sunflower, oilseed rape, canola, sugar beets, soybeans, cotton, pineapple, pastures, meadows, pastures, fallow land, lawn grass, tree and grape orchards, aquatic environments, control objects vegetation in industrial areas (IVM) or rights-of-way (ROW).

The seventh embodiment includes the method of any of the fourth to sixth embodiments, wherein (a), (b) and (c) are applied pre-emergence to the weed or crop.

The eighth embodiment includes the method according to any of the fourth to seventh embodiments, wherein control of unwanted vegetation is carried out in crops tolerant to glyphosate, 5-enolpyruvylshikimate-3phosphate synthase (EPSP) inhibitor, glufosinate, glutamine synthetase inhibitor, dicamba, phenoxyauxin, pyridyloxyauxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl-CoA carboxylase (ACCase) inhibitor, imidazolinone, sulfonylurea, pyrimidinylthiobenzoate, triazolopyrimidine, sulfonylaminocarbonyl

- 1 046237 Triazolinon, acetolactatsintase inhibitors (ALS) or syntase acetohydroxy acids (AHAS), 4-hydroxyphenilpyuruvatdoxygenase inhibitor (HPPD), phytoenesiaceline inhibitor, inhibitor of carotinoids, inhibitor of protoportorinum of protopophynoids Genoxidase (PPO), inhibitor of cellulose biosynthesis, mitosis inhibitor, microtubuleuity inhibitor, inhibitor very long chain fatty acid biosynthesis inhibitor, fatty acid and lipid biosynthesis inhibitor, photosystem I inhibitor, photosystem II inhibitor, triazine or bromoxynil.

The ninth embodiment includes a method according to any of embodiments four through eight, wherein the hardy crop has multiple traits conferring tolerance to multiple herbicides or multiple modes of action.

The tenth embodiment includes a method according to any of the fourth to ninth embodiments, wherein the unwanted vegetation comprises a weed with resistance or tolerance to the herbicide.

Detailed description

Although the teachings of the present invention have been illustrated and described in detail in the figures and description herein, the teachings in the figures and description thereof are to be considered as illustrative and not limiting in nature; It is understood, however, that only illustrative embodiments are shown and described and that all changes and modifications that fall within the spirit of the disclosure are intended to be protected.

Definitions

Unless otherwise indicated, scientific and technological nomenclature have the same meaning as commonly understood by one skilled in the art pertaining to the present invention.

As used herein, unless expressly stated or otherwise implied, the expression approximately refers to a range of values plus or minus 10%, for example, approximately 1.0 covers values from 0.9 to 1.1.

As used herein, halauxifene-methyl (methyl-4-amino-3-chloro-6-(4-chloro-2-fluoro-3methoxyphenyl)picolinate) has the following structure

This compound is described in US Pat. No. 7,314,849 B2, which is incorporated herein by reference in its entirety. Exemplary uses of halauxifen-methyl include its use for the control of broadleaf weeds, such as in cereal crops. Galauxifen-methyl can be used in other forms, for example, halauxifen K+ (potassium 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl) picolinate), which has the following structure

2,4-D DMA, which is methylmethanamine and has the following structure

2-(2,4-dichlorophenoxy)acetic acid with N-

As used herein, glufosinate is 2-amino-4[hydroxy(methyl)phosphinoyl]butyric acid. An exemplary form of glufosinate is glufosinate ammonium, that is, the ammonium salt of glufosinate. It may be referred to as the monoammonium salt of 2-amino-4-(hydroxymethylphosphinyl)butanoic acid and has the following structure

- 2 046237

Other chemical forms of glufosinate (or phosphinothricin) include bialaphos, which is 2-amino-4-(methylphosphino)butyrylalanylalanine and has the following structure

Bialaphos can also be used in salt form such as bialaphos sodium. Exemplary applications are described in Tomlin, C, and ed. A World Compendium The Pesticide Manual. 15th ed. Alton: BCPC Publications, 2009 (hereinafter referred to in this document as The Pesticide Manual, Fifteenth Edition, 2009). Exemplary uses include the use of the compound to control annual and perennial broadleaf weeds and grass weeds. Other chemical forms include glufosinate-P, i.e. S-2-amino-4-[hydroxy(methyl)phosphinoyl]butyric acid.

As used herein, herbicide means a compound, such as an active ingredient, that kills, controls, or otherwise adversely modifies plant growth.

As used herein, a herbicidally effective amount or a sufficient amount to control vegetation is an amount of the active ingredient that causes an adverse modifying effect on vegetation, e.g., aberration, killing, control, moisture loss, growth retardation, etc. .P.

In the context of this document, control of undesirable vegetation means the prevention, weakening, destruction or other adverse modification of the development of plants and vegetation. This document describes methods for controlling unwanted vegetation through the use of certain combinations of herbicides or compositions based thereon. Applications include, but are not limited to, applications to vegetation or its habitat, such as application to an area adjacent to vegetation, as well as pre-emergent, post-emergent, foliar (broadcast, directed, band, hole, mechanized, aerial, or emergency) applications. and water applications (for fully or partially submerged vegetation, broadcast, in holes, mechanized, injected into water, broadcast for granules, in granule holes, by aerosol mixer or sprayer) using hand, backpack, machine, tractor or aviation (plane and helicopter) methods of application.

As used herein, plants and vegetation include, but are not limited to, germinating seeds, emerging seedlings, plants growing from vegetative cuttings, immature vegetation, and mature vegetation.

As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity or that are or can be converted in plants, water or soil into the herbicide mentioned. Exemplary agriculturally acceptable esters are those esters 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, it can be in dissociated or undissociated form.

Exemplary salts include salts derived from alkali or alkaline earth metals, and salts derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium and ammonium cations according to the formula R1R ² R ³ R ⁴ N+;

wherein R ¹ , R ² , R ³ and R ⁴ are each independently hydrogen or C 1 -C ₁₂ alkyl, C ₃ -C ₁₂ alkenyl or C ₃ -C ₁₂ alkynyl, each of which is optionally substituted with one or more hydroxy, C 1 C ₄ alkoxy, C ₁ -C ₄ alkylthio or phenyl groups, provided that R ¹ , R ² , R ³ and R ⁴ are sterically compatible. In addition, any two of R ¹ , R ² , R ³ and R ⁴ together may be an aliphatic bifunctional moiety containing from one to twelve carbon atoms and up to two oxygen or sulfur atoms. Salts can be prepared by treatment with a metal hydroxide such as sodium hydroxide, an amine such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bis-allylamine, 2-butoxyethylamine, morpholine, cyclododecylamine or benzylamine, or a tetraalkylammonium hydroxide such as tetramethylammonium hydroxide or Choline hydroxide.

Exemplary esters include those derived from C1C ₁₂ alkyl, C ₃ -C ₁₂ alkenyl, C ₃ -C ₁₂ alkynyl, or C ₇ -C ₁₀ aryl-substituted alkyl alcohols, such as methyl alcohol, isopropyl alcohol , 1-butanol, 2-ethylhexanol, butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or unsubstituted or substituted benzyl alcohols. Benzyl alcohols may be substituted with 1-3 substituents independently selected from halogen, C1- _C4 alkyl or C1- _C4 alkoxy. Esters can be prepared by combining acids with spir

- 3 046237 volume using any number of suitable activating agents, such as those used for the formation of peptide bonds, such as dicyclohexylcarbodiimide (DCC) or carbonyldiimidazole (CDI); by reacting acids with alkylating agents such as alkyl halides or alkyl sulfonates in the presence of a base such as triethylamine or lithium carbonate; by reacting the acid chloride of the corresponding acid with the corresponding alcohol; by reacting the acid chloride of the corresponding acid with the corresponding alcohol in the presence of an acid catalyst or by a transesterification reaction.

Compositions and methods

Provided herein are herbicidal compositions containing a herbicidal effective amount of (a) halauxifen-methyl; (b) a second herbicide being 2,4-D DMA; and (c) a third glufosinate ammonium herbicide; where the weight ratio of (a), (b) and (c) is from 1:400:400 to 1:130:70.

Also provided herein are methods for controlling unwanted vegetation, comprising the step of contacting a plant, where the plant is the unwanted vegetation, or a habitat thereof, soil or water, where the soil or water supports the growth of the unwanted vegetation, with a herbicidal effective amount of a combination comprising (a) halauxifene-methyl; (b) a second herbicide being 2,4-D DMA; and (c) a third herbicide being ammonium glufosinate; where the weight ratio of (a), (b) and (c) is from 1:400:400 to 1:130:70.

The compounds exhibit herbicidal activity when applied directly to the plant or to the plant's location at any stage of plant growth. The observed effect depends on the type of plant being controlled, the stage of growth of the plant, the application parameters, namely the dilution and droplet size of the liquid sprayed, the particle size of the solid components, the environmental conditions at the time of application, the specific compound used, the specific excipients and carriers used, the type soil, etc., as well as the amount of chemical used. These and other factors can be adjusted to provide non-selective or selective herbicidal action. In some embodiments, the compositions described herein are applied as post-emergence, pre-emergence, or water applications in flooded rice fields or bodies of water (e.g., ponds, lakes, and streams) against relatively immature unwanted vegetation to achieve maximum control weeds.

In some embodiments, the compositions and methods provided herein are used to control weeds in crops including, but not limited to, soil-seeded rice, water-seeded rice and/or seedling rice, cereals, wheat, barley, spp. oats, rye, sorghum, corn/maize, sugar cane, sunflower, oilseed rape, canola, sugar beets, soybeans, cotton, pineapple, in pastures, meadows, pastures, fallow land, lawn grass, tree and grape orchards, water environments, plantation crops, vegetable crops, industrial vegetation control (IVM) or right-of-way (ROW).

The compositions and methods can be used in the control of unwanted 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 crop improvement traits (including, but not limited to, yield; protein, carbohydrate or oil content; protein, carbohydrate or oil composition; plant structure and plant architecture).

The compositions and methods presented herein are used to control unwanted vegetation. Undesirable vegetation includes, but is not limited to, undesirable vegetation that occurs in rice, grain crops, wheat, barley, oats, rye, pastures, meadows, pastures, fallow land, row crops (e.g., corn/maize, sugar cane, sunflowers , oilseed rape, canola, sugar beet, soybean, cotton), turfgrass, tree and vineyards, plantation crops, vegetable crops, ornamental species, aquatic environments or non-agricultural plantings (e.g. rights-of-way, vegetation control facilities in industrial areas) .

In some embodiments, the methods presented herein are used to control unwanted vegetation in rice. In certain embodiments, the unwanted vegetation is Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf grass, BRAPP), Digitaria sanguinalis (L.) Scop, (blood red crabgrass, DIGSA), Echinochloa spp. (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (common barnyard grass, ECHCG), Echinochloa crus-pavonis (Kunth) Schult. (peacock barnyard, ECHCV), Echinochloa colonum (L.) LINK (peacock barnyard, ECHPH), Echinochloa oryzoides (Ard.) Fritsch (rice barnyard, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (bearded barnyard, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (rice grass, ECHPH), Echinochloa polystachya (Kunth) Hitchc.

- 4 046237 (multi-haired wool, ECHPO), Ischaemum rugosum Salisb. (ischemum, ISCRU), Leptochloa chinensis (L.) Nees (LEFCH), Leptochloa fascicularis (Lam.) Gray (LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazonian weedgrass, LEFPA), Oryza spp. (red weedy rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (split-flowered millet, PANDI), Paspalum dilatatum Poir. (expanded buckwheat, PASDI), Rottboellia cochinchinensis (Lour.) W.D. Clayton (high rottbelia, ROOEX), Cyperus spp. (CYPSS), Cyperus difformis L. (heterogeneous orchard, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (edible cornwort, CYPES), Cyperus iria L. (round cornwort, CYPIR), Cyperus rotundus L. (round cornwort, CYPRO), Cyperus serotinus Rottb./C.B.Clarke (late cottonmouth, CYPSE) , Eleocharis spp. (ELOSS), Fimbristylis miliacea (L.) Vahl (fimbristylis, FIMMI), Schoenoplectus spp. (SCPSS), Schoenoplectus juncoides Roxb. (Japanese reed, SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus L. Lye (marine reed, SCPMA), Schoenoplectus mucronatus L. (Schoenoplectus acuminate, SCPMU), Aeschynomene species (Virginian pennywort, AESSS), Alternanthera philoxeroides ( Mart.) Griseb. (alternanthera phylloxeroides, ALRPH), Alisma plantago-aquatica L. (common chastocha, ALSPA), Amaranthus spp., (chenozematodes and amaranthaceae, AMASS), Ammannia coccinea Rottb. (Ammania benghalensis, AMMSO), Commelina benghalensis L. (Commelina bengal, COMBE), Eclipta alba (L.) Hassk. (eclipta alba, ECLAL), Heteranthera limosa (SW.) Willd./Vahl (heteranthera muddy, HETLI), Heteranthera reniformis R. & P. (heteranthera reniform, HETRE), Ipomoea spp. (IPOSS), Ipomoea hederacea (L .) Jacque. (Ipomoea ivy, IPOHE), Lindernia dubia (L.) Pennell (LIDDU), Ludwigia spp. (LUDSS), Ludwigia linifolia Poir. (Ludwigia hyssopolis, LUDLI), Ludwigia octovalvis (Jacq.) Raven (Ludwigia octovalvis, LUDOC), Monochoria korsakowii Regel & Maack (monochory, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth (monochory, MOOVA) , Murdannia nudiflora (L.) Brenan (MUDNU), Polygonum pensylvanicum L. (Pennsylvanian knotweed, POLPY), Polygonum persicaria L. (POLPE), Polygonum hydropiperoides Michx. (POLHP), Rotala indica (Willd.) Koehne (ROTIN), Sagittaria spp. (SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (sesbania tall, SEBEX) or Sphenoclea zeylanica Gaertn. (Sphenoclea ceylonensis, SPDZE).

In some embodiments, the methods presented herein are used to control unwanted vegetation in crops. In certain embodiments, the unwanted vegetation is Alopecurus myosuroides Huds. (foxtail mousetail, ALOMY), Apera spica-venti (L.) Beauv. (common broom, APESV), Avena fatua L. (empty oats, AVEFA), Bromus tectorum L. (brome, BROTE), Lolium multiflorum Lam. (multiflora tares, LOLMU), Phalaris minor Retz. (small canary grass, PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria pumila (Poir.) Roemer & J.A. Schultes (low bristle grass, SETLU), Setaria viridis (L.) Beauv. (green bristleweed, SETVI), Amaranthus retroflexus (Amaranthus amaranth, AMARE), Brassica spp. (BRSSS), Chenopodium album L. (white pigweed, CHEAL), Cirsium arvense (L.) Scop, (thistle, CIRAR), Galium aparine L. (grass bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureum L. (purple lily, LAMPU), Matricaria recutita L. (chamomile, MATCH), Matricaria matricarioides (Less.) Porter (chamomile, MATMT), Papaver rhoeas L. (poppy, PAPRH), Polygonum convolvulus L. (convolvulus, POLCO), Salsola tragus L. (Russian solyanka, SASKR), Sinapis species (SINSS), Sinapis arvensis (field mustard, SINAR), Stellaria media (L.) Vill. (chickweed, STEME), Veronica persica Poir. (Veronica Persica, VERPE), Viola arvensis Murr. (field violet, VIOAR) or Viola tricolor L. (tricolor violet, VIOTR).

In some embodiments, the methods presented herein are used to control unwanted vegetation in pastures and pastures, fallow land, IVM and ROW. In certain embodiments, the unwanted vegetation is Ambrosia artemisiifolia L. (ambrosia ragweed, AMBEL), Cassia obtusifolia (senna obtusifolia, CASOB), Centaurea maculosa auct. non Lam. (spotted cornflower, CENMA), Cirsium arvense (L.) Scop, (field thistle, CIRAR), Convolvulus arvensis L. (field bindweed, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L. (euphorbia acute, EPHES), Lactuca serriola L./Torn. (wild lettuce, LACSE), Plantago lanceolata L. (plantain, PLALA), Rumex obtusifolius L. (sorrel, RUMOB), Sida spinosa L. (sedum, SIDSP), Sinapis arvensis L. (field mustard, SINAR) , Sonchus arvensis L. (Sow thistle, SONAR), Solidago spp. (goldenrod, SOOSS), Taraxacum officinale G.H. Weber ex Wiggers (common dandelion, TAROF), Trifolium repens L. (creeping clover, TRFRE) or Urtica dioica L. (nettle, URTDI).

In some embodiments, the methods presented herein are used to control unwanted vegetation that occurs in row crops, tree crops, vine crops, and perennial crops. In certain embodiments, the unwanted vegetation is Alopecurus myosuroides Huds. (Mousetail foxtail, ALOMY), Avena fatua L. (Empty oats, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) R.D. Webster (branchwort, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. Or Urochloa brizantha (Hochst. ex A. Rich.) R.D. (brachiaria palisade, BRABR), Brachiaria platyphylla

- 5 046237 (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf branch, BRAPP), Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) R.D. Webster (BRAPL), Cenchrus echinatus L. (CENEC), Digitaria horizontalis Willd. (horizontal crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman (island crabgrass, TRCIN), Digitaria sanguinalis (L.) Scop, (blood-red crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (common barnyard grass, ECHCG), Echinochloa colonum (L.) Link (peasant barnyard grass, ECHCG), Eleusine indica (L.) Gaertn. (Eleusina indica, ELEIN), Lolium multiflorum Lam. (multiflora tares, LOLMU), Panicum dichotomiflorum Michx. (forked millet, PANDI), Panicum miliaceum L. (common millet, PANMI), Setaria faberi Herrm. (Faber's bristleweed, SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum halepense (L.) Pers. (Aleppo sorghum, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (grass sorghum, SORVU), Cyperus esculentus L. (edible sorghum, CYPES), Cyperus rotundus L. (round sorghum, CYPRO), Abutilon theophrasti Medik. (Theophrastus's rope, ABUTH), Amaranthus spp. (Chenopodiaceae and amaranthaceae, AMASS), Ambrosia artemisiifolia L. (Ambrosia wormwood, AMBEL), Ambrosia psilostachya DC. (ragweed, AMBPS), Ambrosia trifida L. (ambrosia tripartite, AMBTR), Anoda cristata (L.) Schlecht. (anode comb, ANVCR), Asclepias syriaca L. (Syrian cottonweed, ASCSY), Bidens pilosa L. (hairy comb, BIDPI), Borreria spp. (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (Borenia, BOILF), Spermacose latifolia, Chenopodium album L., Cirsium arvense (L.) Scop, Commelina benghalensis L. COMBE), Datura stramonium L. (datura, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (spurge, EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (Spurge spurge, EPHHI), Euphorbia dentata Michx. (spurge spurge, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (ERIBO), Erigeron sumatrensis or Conyza sumatrensis (ERISU), Erigeron canadensis L. or Conyza canadensis (ERICA) or other related species (Conyza spp, ERISS), Helianthus annuus L. (sunflower common, HELAN), Jacquemontia tamnifolia (L.) Griseb. (Jakemontia tamnifolia, IAQTA), Ipomoea hederacea (L.) Jacq. (Ipomoea ivy, IPOHE), Ipomoea lacunosa L. (Ipomoea pitta, IPOLA), Lactuca serriola L./Torn. (wild lettuce, LACSE), Portulaca oleracea L. (POROL), Richardia spp., RCHSS, Sida spp., SIDSS, Sida spinosa L. (SIDSP), Sinapis arvensis L. ( field mustard, SINAR), Solanum ptychanthum Dunal (SOLPT), Tridax procumbens L. (TRQPR) or Xanthium strumarium L. (XANST).

In some embodiments, the methods presented herein are used to control unwanted vegetation in turfgrass. In certain embodiments, the unwanted vegetation is Bellis perennis L., Cyperus esculentus L., Cyperus spp. (CYPSS), Digitaria sanguinalis (L.) Scop, DIGSA), Diodia virginiana L. (DIQVI), Euphorbia species (spurge, EPHSS), Glechoma hederacea L. (ivy bud, GLEHE), Hydrocotyle umbellata L. (money, HYDUM), Kyllinga species (KYLSS) , Lamium amplexicaule L. (LAMAM), Murdannia nudiflora (L.) Brenan (MUDNU), Oxalis spp. (OXASS), Plantago major L. (PLAMA), Plantago lanceolata L. ( plantain, PLALA), Phyllanthus urinaria L., Rumex obtusifolius L., Stachys floridana Shuttlew. (Florida chickweed, STAFL), Stellaria media (L.) Vill. (Starweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers (common dandelion, TAROF), Trifolium repens L. (creeping clover, TRFRE) or Viola spp. (tricolored violet, VIOSS).

In some embodiments, the compositions provided herein are used to control unwanted vegetation, including grasses, broadleaf and sedge weeds. In certain embodiments, the compositions and methods presented herein are used to control unwanted vegetation, including, but not limited to, Alopecurus, Avena, Centaurea, Cyperus, Digitaria, Echinochloa, Ipomoea, Leptochloa, and Sonchus.

With respect to methods, in certain embodiments, the methods include bringing the composition described herein into contact with or applying to undesirable vegetation or vegetation to soil or water to prevent the emergence or growth of vegetation. In some embodiments, the composition is applied at an application rate of from about 1 g of active ingredient per hectare (ha.i./ha) to about 1000 g of active ingredient per hectare (ha.i./ha) based on the total amount of active ingredients in the composition . In certain embodiments, the composition is applied at an application rate of from about 4 g acid equivalent per hectare (g eq/ha) to about 1000 g eq. k./ha in terms of the total amount of active ingredients in the composition.

In some embodiments, the composition contains a combination comprising halauxifene-methyl (a), and 2,4-D DMA (b), and glufosinate ammonium, where the weight ratio of (a), (b) and (c) is 1:130 :70, 1:131:70, 1:132:70, 1:133:70, 1:134:70, 1:135:70, 1:136:70, 1:137:70, 1:138:70 , 1:139:70,

- 6 046237

1:140:70, 1:150:70, 1:200:70, 1:130:75, 1:131:75, 1:132:75, 1:133:75, 1:134:75, 1: 135:75, 1:136:75, 1:137:75, 1:138:75, 1:139:75, 1:140:75, 1:150:75, 1:200:75, 1:130: 77, 1:131:77, 1:132:77, 1:133:77, 1:134:77, 1:135:77, 1:136:77, 1:137:77, 1:138:77, 1:139:77, 1:140:77, 1:150:77, 1:200:77 or 1:200:200.

With respect to methods, in certain embodiments, the methods include bringing the composition described herein into contact with or applying to undesirable vegetation or vegetation to soil or water to prevent the emergence or growth of vegetation. In some embodiments, the composition is applied at an application rate of from about 1 g of active ingredient per hectare (g ai/ha) to about 500 g (g ai/ha) based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 4 g acid equivalent per hectare (g eq/ha) to about 400 g eq. k./ha in terms of the total amount of active ingredients in the composition.

The compositions disclosed herein can be applied to AAD1 and AAD12 monocotyledonous and dicotyledonous crops, wherein the crop is tolerant of all 3 modes of action, providing growers with a means to control susceptible and resistant broadleaf weeds, as well as to control development of resistance through the use of a product with 3 mechanisms of action.

The components of the compositions described herein can be used individually or as a component of a multicomponent herbicide system.

The compositions described herein can be used in combination with one or more additional herbicides to control a wider range of unwanted vegetation. When used in combination with other herbicides, the composition may be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides, or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be used in combination with the compositions and methods described herein include, but are not limited to, 4-CPA; 4-SRV; 4-CPP; 3,4-DA; 3,4-DB; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TV; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametrine, amibusin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrol, ammonium sulfamate, anilofos, anizuron, asulam , atraton, atrazine, azaphenidine, azimsulfuron, aziprotrine, barban, BCRS, beflubutamide, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, benthiocarb, bentazone-sodium, benzadox, benzfendizone, benzipram, benzobicyclone, benzophenap, benzofluor , benzoylprop, benzthiazuron, bialaphos, bicyclopyrone, bifenox, bilanafos, bispiribac sodium, borax, bromacil, bromobonil, bromobutide, bromophenoxime, bromoxynil, brompyrazone, butachlor, butafenacil, butamiphos, butenachlor, butidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafen strol , calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole, chlorprocarb, carfentrazone-ethyl, CDEA, SEPC, chlomethoxifene, chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazone , chlorimuron, chlornitrophen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamide, cynidone-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim, cliodinate, clodinafoppropargyl, clofop, clomazone, clomeprop, cloprop, cloproxydim, k lopiralide, cloransulam -methyl, SMA, copper sulfate, CPMF, CPRS, credazine, cresol, cumyluron, cyanathrine, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, cypromide, daimuron, dalapon, dazomet, delachlor, desmedipham, desmethrin, diallate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, dietamquat, dietyl, diphenopentene, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, di methamethrin, dimethenamid, dimethenamid-P, dimexano, dimidazone, dinitramine, dinophenate, dinoprop, dinosam, dinoseb, dinoterb, difenamide, dipropetrin, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EVER, eglinasine, endothal, epronase, EPTC, Erbon, Esprokarb, Etalfluralin, Etbenzamid, ethemetsulfuron, these dyamuron, etilat, it isbenzamide, it isbenzamide, this fumesate, ethoxifen, ethoxyphuron, ethinophen, ethnicoprom, it is bunzanide, fenasulas, phenoprop, fenokasaprop. Enoksaprop-p-ethyl+ isoxadifen-ethyl, fenoxasulfone, fenterakol, fentiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P-butyl, fluazolate, flucarbazone, flusetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr-ethyl , flumetsulam, flumesin, flumiclorac-pentyl, flumioxazin, flumipropin, fluometuron, fluorodifen, fluoroglycophene, fluoromidine, fluoronitrophen, fluotiuron, flupoxam, flupropacil, flupropanate, flupirsulfuron, fluridone, flurochloridone, flurtamone, flutiacet , fomesafen, foramsulfuron, fosamine, fumiclorac, furyloxifene , glyphosate salts and esters, halosaphene, halauxifen, halauxifen-methyl, halosulfuron-methyl, haloxidin, haloxyfop-methyl, haloxyfop-P-methyl, hexachloracetone, hexaflurate, hexazinone, imazosulfuron, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iodosulf damage -ethyl sodium, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprimidam, isocarbamide, isocyl, isomethiosine, isonoruron,

- 7 046237 isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortol, isoxaflutole, isoxapirifop, carbutylate, ketospiradox, lactofen, lenacyl, linuron, MAA, MAMA, esters and amines MCPA, MCPA-thioethyl, MCRP, mecoprop, mecoprop-P , medinoterb, mefenacet, mefluidide, mesoprazine, mezosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazone, metabenzthiazuron, metalpropalin, metazol, methiobencarb, methiozoline, methiuron, metometon, metoprothrin, methylbromine d, methyl isothiocyanate, methyl dimron, metobenzuron, methobromuron , metolachlor, metosulam, methoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morphamquat, MSMA, naproanilide, napropamide, napthalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrophen, nor trofluorfen, norflurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazone, oxapirazone, oxasulfuron, oxaziclomefon, oxyfluorfen, paraflufen-ethyl, parafluron, pebulate, pelargonic acid, pendimethalin, penoxulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone , petoxamide, phenizofam, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercuracetate, pichloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron-methyl, procyazine, prodiamine, profluazole, profluralin, profoxydim , proglinazine, Progosadion-Calcium, between, Primetrin, Pronjon, Perekhalor, Rassaned, Ostakkhafop, Prazin, Profam, Propisochlor, Propoxicarbazon, Propyrisulfuron, Propizamide, Enterprise, Environmentalcarb, Susephuron, Sksan, Prianlor, Pidanon, Py and Pyiraclufin, Pyruclufin, Pyrashefotol Gil, pyrazolinate, pyrazosulfuron-ethyl, pyrazoxifene, pyribenzoxime, pyributicarb, pyrichlor, pyridafol, pyridate, pyrifthalide, pyriminobac-methyl, pyrimisulfan, pyrithiobac-sodium, pyroxasulfone, piroxulam, quinclorac, quinmerac, quinoclamine, quinonamide, quizalofop, quizalofopP-ethyl, rodtanil, rimsulfuron, S-metolachlor, sebutylazine, sebumetone, sethoxydim, siduron, simazine, simeton, symetrine, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfalate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglicapin, swep, SYN523, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumetone, terbutylazine, terbutryn, tetrafluron, tenylchlor, thiazafluron, thiazopyr, thidiazimine, thidiazuron, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiaphenacyl, thiocarbazyl, thioclorim, topramesone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricamba, trichloropyr choline salt, triclopyr esters and amines, tridifan, triethazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop, trifopsim , trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron, vernolate, xylachlor and salts, esters, optically active isomers and mixtures thereof.

In some embodiments, the compositions described herein can be used in combination with one or more additional herbicides to control a broader range of unwanted vegetation. When used in combination with other herbicides, the composition may be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides, or applied sequentially with the other herbicide or herbicides. Some herbicides that may be used in combination with the compositions and methods described herein include, but are not limited to, acifluorfen, acifluorfen sodium, azaphenidine, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxifene, cynidone-ethyl, fluazolate , flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycophene, fluoroglycophene-ethyl, flutiacet, flutiacet-methyl, fomesafen, halosaphene, ipfencarbazone, lactofen, oxadiargyl, oxadiazone, oxyfluorfen, pentoxazone, profluazole, pyra clonil, pyraflufen, pyraflufen -ethyl, saflufenacil, sulfentrazone, thidiazimine, thiaphenacyl, trifludimoxazine, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4 -tetrahydropyrimidin-3yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4trifluoromethylphenoxy)-5-methyl-N-pyrazol- 1-Carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N- ethyl3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-III-pyrazole-1-carboxamide (CAS 452099-05-7), Ntetrahydrofurfuryl-3-(2-chloro-6-fluoro-4 -trifluoromethylphenoxy)-5-methyl-III-pyrazole-1-carboxamide (CAS 45100-03-7) and 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro -2H-benzo[1,4]oxazin-6-yl]-1,5dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione; b5) from the group of bleaching herbicides.

Agriculturally suitable excipients and carriers include, but are not limited to, crop aid oil concentrate; nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; a mixture of petroleum hydrocarbon, alkyl esters, organic acid and anionic surfactant; C9-C11 alkyl polyglycoside; phosphoric acid alcohol ethoxylate; natural primary alcohol ethoxylate (C12-C16); di-sec-butylphenol block copolymer EO-PO; methyl-terminated polysiloxane; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol ethoxylate (synthetic) (8 EO); Tall amine ethoxylate (15 EO) and PEG(400) dioleate-99.

Useful liquid carriers include water and organic solvents. Organic races

- 8 046237 solvents include, without limitation, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffin 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), such as 2-ethylhexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, dioctyl succinate, dibutyl adipate, dioctyl phthalate and the like; esters of mono-, di- and polycarboxylic acids, etc. Specific organic solvents include without restriction of toluene, xylol, ligroin, oil auxiliary, acetone, methylexon, cyclogloexanon, trichlorethilene, perchlorethilene, ethylacetate, amylacetate, butylacetate, monomethyllycol air and monomethylene dietallycol. RT, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerin, N-methyl-2-pyrrolidinone, N.N-dimethylalkylamides. dimethyl sulfoxide, liquid fertilizers, etc. In certain embodiments, water is the vehicle for diluting the concentrates.

Suitable solid carriers include, but are not limited to, talc, pyrophyllite clay, silica, attapulgite clay, kaolin clay, diatomaceous earth, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, nut shell flour, lignin, cellulose, etc.

In some embodiments, the compositions described herein further contain one or more surfactants. In some embodiments, such surfactants are used in both solid and liquid compositions, and in certain embodiments, those intended to be diluted with a carrier prior to use. Surfactants may be anionic, cationic or nonionic in nature and may be used as emulsifiers, wetting agents, suspending agents or other purposes. Surfactants that can also be used in the compositions of the present invention are described, among others, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New Jersey, 1998 and in Encyclopedia of Surfactants, Vol. I-III, Chemical Publishing Co., New York, 1980-81. Surfactants include, but are not limited to, alkyl sulfate salts such as diethanolammonium lauryl sulfate; alkylaryl sulfonate salts such as calcium dodecylbenzenesulfonate; addition products of alkylene oxides and alkylphenols, such as nonylphenol-C18 ethoxylate; addition products of alkylene oxides and alcohols, such as tridecyl alcohol ethoxylate-C16; soaps such as sodium stearate; alkyl naphthalene sulfonate salts such as sodium dibutyl naphthalene sulfonate; dialkyl esters of sulfosuccinate salts such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters such as sorbitan oleate; quaternary amines such as lauryltrimethylammonium chloride; polyethylene glycol fatty acid esters such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono- and dialkylphosphate esters; vegetable or seed oils such as soybean oil, canola/canola oil, olive oil, castor oil, sunflower oil, coconut oil, corn oil, cottonseed oil, flaxseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil, etc.; and esters of the above vegetable oils, and in certain embodiments, methyl esters.

In some embodiments, these materials, such as vegetable or seed oils and their esters, can be used interchangeably as an agricultural excipient, as a liquid carrier, or as a surfactant.

Other exemplary additives for use in the compositions provided herein include, but are not limited to, compatibilizers, antifoams, binding agents, neutralizing agents and buffers, corrosion inhibitors, colorants, fragrances, distribution aids, penetration aids, adhesion aids. , dispersants, thickeners, freezing point depressants, antimicrobial agents, etc. The compositions may also contain other compatible components, for example, other herbicides, plant growth regulators, fungicides, insecticides and the like. and can be formulated with carriers based on liquid fertilizers or solid particulate fertilizers such as ammonium nitrate, urea and the like.

In some embodiments, the concentration of active ingredients in the compositions described herein ranges from about 0.0005 to 98% by weight. In some embodiments, the concentration is from about 0.0006 to 90% by weight. In compositions formulated for use as concentrates, the active ingredients are present in a concentration of from about 0.1 to 98% by weight, and in certain embodiments, from about 0.5 to 90% by weight. In certain cases, before

- 9 046237 application, such embodiment compositions are diluted with an inert carrier such as water. The diluted compositions, which are typically applied to weeds or weed habitats, in certain embodiments contain the active ingredient in an amount of from about 0.0006 to 3.0% by weight and in certain embodiments in an amount from about 0.01 to 1 .0% by weight.

The compositions of the present invention can be applied to weeds or their habitats through the use of conventional ground or aerial sprayers, sprayers and granule spreaders, by addition to irrigation water or by other conventional means known to those skilled in the art.

The described embodiments and the following examples are for illustrative purposes only and are not intended to limit the scope of the claims. Other modifications, uses or combinations with respect to the compositions described herein will be apparent to one of ordinary skill in the art without departing from the spirit and scope of the claimed subject matter.

Examples

The results in the Examples section are from greenhouse tests.

Seeds or nuts of the desired test plant species were planted in a soil base prepared by mixing loam or sandy loam soil (eg, 28.6% loam, 18.8% clay, and 52.6% sand with a pH of approximately 5.8 and organic matter, approximately 1.8%) and calcareous sand formation in a ratio of 80 to 20.

The soil base was placed in 1 quart plastic pots with a surface area of 83.6 cm2. Fungicide and/or other chemical or physical treatments were applied when necessary to ensure good germination and healthy plants. Plants were grown for 8-22 days in a greenhouse with an approximately 14-hour photoperiod in which the temperature was maintained at approximately 29°C during the day and at 26°C during the night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg and iron chelate) were used as a drench solution as needed and water was added regularly. If necessary, additional lighting was provided using ceiling-mounted 1000-watt metal halide lamps. Plants were used for testing when they reached the first to fourth true leaf stage.

The treatments contained acid or halauxifen methyl esters (methyl 4amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate), each formulated as an SC (suspension concentrate), and various herbicidal components individually and in combination.

Treatment parameters were calculated based on the rates tested, the concentration of active ingredient or acid equivalent in the formulation for a volume of 12 ml, based on an application rate of 187 l/ha.

For treatments containing formulated compounds, measured amounts of the compounds can be added individually to 25 mL glass vials and diluted in a volume of 1.25% (v/v) Agri-Dex® Crop Oil Concentrate to produce 12X the original solutions. If the test compound dissolved slowly, the mixture was heated and/or sonicated. Application solutions were prepared by adding the appropriate amount of each stock solution (e.g., 1 mL) and diluting to the appropriate final concentrations by adding 10 mL of an aqueous mixture of 1.25% (v/v) crop oil concentrate so that the final spray solutions contained 1.25+/-0.05% (v/v) crop oil concentrate.

For treatments containing technical compounds, weighed quantities can be added individually to 25 ml glass vials and diluted at a ratio of 97:3 v/v. acetone/DMSO mixtures to obtain 12X stock solutions. If the test compound dissolved slowly, the mixture was heated and/or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluting to appropriate final concentrations by adding 10 mL of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that The final spray solutions contained 1.25% (v/v) crop oil concentrate. When using technical materials, concentrated stock solutions can be added to spray solutions in such quantities that the final concentrations of acetone and DMSO in application solutions are 16.2% and 0.5%, respectively.

For treatments consisting of formulated and technical compounds, weighed quantities of technical materials were added individually into 25 ml glass vials and dissolved in a volume of 97:3 v/v. acetone/DMSO mixture to obtain a 12X stock solution, and measured amounts of the formulated compounds were added individually to 25 mL glass vials and diluted in a volume of 1.5% (v/v) crop oil concentrate or water to obtain a 12X stock solution . If the test compound dissolved slowly, the mixture was heated and/or sonicated. Solutions for use were prepared by adding the proportions

- 10 046237 the appropriate amount of each stock solution (e.g. 1 ml) and diluted to the appropriate final concentrations by adding the appropriate amount of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contain 1.25% (v/v) crop oil concentrate. If necessary, additional water and/or 97:3 v/v were added to individual application solutions. acetone/DMSO mixtures, resulting in final concentrations of acetone and DMSO in the comparison application solutions of 8.1% and 0.25%, respectively.

Before use, all stock and application solutions were visually assessed for compound compatibility. Spray solutions were applied to the plant material using a Mandel down-jet sprayer equipped with an 8002E nozzle calibrated to deliver 187 L/ha over a 0.503 m2 application area at a spray height of 18-20 inches (46-50 cm) above the average plant canopy. Control plants were sprayed in the same way using solvent blank.

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 approximately 7, 28 and 43 days (DAA; days after application), the condition of the test plants was visually determined in comparison with untreated plants and scored on a scale of 0 to 100%, where 0 corresponds to no damage or growth inhibition and 100 corresponds to complete destruction.

The tested compounds, application rates used, test plant species and results are given in Table. 1.

In table Figure 1 shows weed control with foliar application of compositions containing halauxifen-methyl + 2,4-O-dimethylammonium (2,4-D-DMA) + glufosinate to various broadleaf weeds. In table 1 demonstrates that the use of a pre-prepared mixture (chemical 1; 3.8 g eq./ha/l halauxifen-methyl + 520.4 g eq./ha/l 2,4-D DMA) in the amount 654.99 g a. i./ha and glufosinate in the amount of 49 g a. i./ha provides effective control of ERISS (Conyza spp). The compositions disclosed herein can be used in contact application and application to fallow crops or to herbicide-tolerant crops. Such compositions can be used to control a wide range of broadleaf weeds, including, but not limited to, broadleaf weeds resistant to ALS, auxin transport inhibitors, HPPD, PPO, glufosinate and glyphosate. The compositions disclosed herein can be applied to AAD1 and AAD12 monocotyledonous and dicotyledonous crops, wherein the crop is tolerant of all 3 modes of action, providing growers with a means to control susceptible and resistant broadleaf weeds and to inhibit development sustainability through the use of a product with 3 mechanisms of action. The compositions disclosed herein can be used in non-agricultural lands and R&P/IVM, post-emergence contact applications on perennial crops and potentially on a variety of crops that are tolerant to all 3 mechanisms of action.

- 11 046237

Table 1

Results of control of ERISU weed (Conyza sumatrensis) populations on the indicated days after application (DAA) using tank mixtures of halauxifen-methyl + 2,4^ dimethylammonium (2,4-D DMA) + glufosinate

TRIAL Weed code according to Bayer Est. interval processed Chemical 1 Chem. thing 1 Application standard (g a.i./ha) Chem. thing 1 Actual avg. % weed control Chemical 2 Chem. thing 2 Application standard (g a.i./ha) Chem. thing 2 Actual avg. % weed control Combined actual avg. % weed control Combined forecast. average% weed control Number of observations A 1 ERISU 17 DAA Galauxifene-methyl+2,4D dimethylammonium 654.99 35.00 Glufosinate -ammonium 366 58.75 80.00 73.19 4 0.074 1 ERISU 28 DAA Galauxifene-methyl+2,4D dimethylammonium 654.99 61.25 Glufosinate -ammonium 366 71.25 97.00 89.00 4 0.058 1 ERISU 43 DAA Galauxifene-methyl+2,4D dimethylammonium 654.99 71.25 Glufosinate -ammonium 366 78.75 97.50 94.06 4 0.252 2 ERISU 17 DAA Galauxifene-methyl+2,4D dimethylammonium 654.99 36.25 Glufosinate -ammonium 366 71.25 94.50 81.50 4 0.025 2 ERISU 28 DAA Galauxifene-methyl+2,4D dimethylammonium 654.99 48.75 Glufosinate -ammonium 366 85.00 97.50 92.38 4 0.023 2 ERISU 43 DAA Galauxifene-methyl+2,4D dimethylammonium 654.99 74.50 Glufosinate -ammonium 366 97.50 100.00 99.29 4 0.198

Although the new technology has been illustrated and described in detail in the drawings and in the foregoing description, it should be considered as illustrative and not limiting in nature, it being understood that only preferred embodiments have been shown and described and that all changes and modifications that correspond to the essence of the new technology are subject to protection. In addition, although the new technology has been illustrated using specific examples, theoretical arguments, reports, and illustrations, these illustrations and the accompanying discussion should in no way be interpreted as a limitation of the technology. All patents, patent applications and references to texts, scientific papers, publications, etc., referenced in this application are incorporated herein by reference in their entirety to the extent they do not conflict with the express teachings of this specification.

Claims (10)

CLAIM 1. Herbicidal composition, which contains a herbicidal effective amount of (a) halauxifen-methyl; (b) a second herbicide being 2,4-D DMA; and (c) a third glufosinate ammonium herbicide; where the weight ratio of (a), (b) and (c) is from 1:400:400 to 1:130:70. 2. The composition according to claim 1, further containing an agriculturally acceptable excipient or carrier. 3. Composition according to claim 1 or 2, where the weight ratio of (a), (b) and (c) is 1:130:70, 1:131:70, 1:132:70, 1:133:70, 1:134:70, 1:135:70, 1:136:70, 1:137:70, 1:138:70, 1:139:70, 1: 140:70, 1:150:70, 1:200:70, 1:130:75, 1:131:75, 1:132:75, 1:133:75, 1:134:75, 1:135:75, 1:136:75, 1:137:75, 1: 138:75, 1:139:75, 1:140:75, 1:150:75, 1:200:75, 1:130:77, 1:131:77, 1:132:77, 1:133:77, 1:134:77, 1:135:77, 1: 136:77, 1:137:77, 1:138:77, 1:139:77, 1:140:77, 1:150:77, 1:200:77 or 1:200:200. 4. A method of controlling unwanted vegetation, comprising the step of contacting a plant, where the plant is the unwanted vegetation, or a place where it is growing, soil or water, where the soil or water supports the growth of unwanted vegetation, with a herbicidal effective amount of a combination containing (a) halauxifene-methyl; (b) a second herbicide being 2,4-D DMA; and (c) a third herbicide being ammonium glufosinate; where the weight ratio of (a), (b) and (c) is from 1:400:400 to 1:130:70. 5. The method according to claim 4, where the weight ratio of (a), (b) and (c) is 1:130:70, 1:131:70, 1:132:70, 1:133:70, 1:134:70, 1:135:70, 1:136:70, 1:137:70, 1:138:70, 1:139:70, 1:140:70, 1: 150:70, 1:200:70, 1:130:75, 1:131:75, 1:132:75, 1:133:75, 1:134:75, 1:135:75, 1:136:75, 1:137:75, 1:138:75, 1: 139:75, 1:140:75, 1:150:75, 1:200:75, 1:130:77, 1:131:77, 1:132:77, 1:133:77, 1:134:77, 1:135:77, 1:136:77, 1: 137:77, 1:138:77, 1:139:77, 1:140:77, 1:150:77, 1:200:77 or 1:200:200. 6. The method according to claim 4 or 5, where control of unwanted vegetation is carried out in rice with sowing seeds in the ground, with sowing seeds in water and seedling rice, cereals, wheat, barley, species - 12 046237 oats, rye, sorghum, corn/maize, sugar cane, sunflower, oilseed rape, canola, sugar beets, soybeans, cotton, pineapple, in pastures, meadows, pastures, fallow land, in lawn grass, trees and grapes gardens, aquatic environments, industrial vegetation control (IVM) or right-of-way (ROW). 7. The method according to any one of claims 4-6, where (a), (b) and (c) are applied before emergence to a weed or crop. 8. The method according to any one of claims 4-7, where the control of unwanted vegetation is carried out in crops tolerant to glyphosate, 5enolpyruvylshikimate-3-phosphate synthase (EPSP) inhibitor, glufosinate, glutamine synthetase inhibitor, dicamba, phenoxyauxin, pyridyloxyauxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl-CoA carboxylase (ACCase) inhibitor, imidazolinone, sulfonylurea, pyrimidinylthiobenzoate, triazolopyrimidine, sulfonylaminocarbonyltriazolinone, acetolactate synthase (ALS) or synthase inhibitors acetohydroxy acids (AHAS), an inhibitor of 4-hydroxyphenylpyruvate dioxygenase ( HPPD), phytoene desaturase inhibitor, carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase (PPO) inhibitor, cellulose biosynthesis inhibitor, mitosis inhibitor, microtubule assembly inhibitor, very long chain fatty acid biosynthesis inhibitor, fatty acid and lipid biosynthesis inhibitor, photosystem I inhibitor, photosystem II inhibitor , triazine or bromoxynil. 9. The method of claim 8, wherein the hardy crop has multiple traits conferring tolerance to multiple herbicides or multiple modes of action. 10. The method according to any one of claims 4 to 9, wherein the unwanted vegetation comprises a weed with resistance or tolerance to the herbicide.