EA045664B1 - COMPOSITIONS CONTAINING HALAUXIFEN AND OTHER HERBICIDES, AND RELATED METHODS - Google Patents

Description

Field of technology to which the invention relates

Provided herein are herbicidal compositions comprising at least one pyridine or pyrimidine carboxylic acid herbicide, a second herbicide and a third herbicide, or agriculturally acceptable salts, esters and amides thereof. Also provided herein are methods for controlling unwanted vegetation, including the use of the compositions disclosed herein.

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) halauxifene methyl; (b) a second herbicide comprising 2,4-D DMA; and (c) a third herbicide comprising saflufenacil; where the weight ratio of the components [(a)+(b)] to [c] is from 20:1 to 10:1.

The second embodiment includes a composition in accordance with the first embodiment, which further includes an agriculturally acceptable excipient or carrier.

The third embodiment includes a composition in accordance with the first or second embodiments, which further includes at least one herbicide antidote.

A fourth embodiment includes a method of controlling unwanted vegetation, comprising the steps 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 composition comprising (a ) halauxifenemethyl; (b) a second herbicide comprising 2,4-D DMA; and (c) a third herbicide comprising saflufenacil; where the weight ratio of the components [(a)+(b)] to [c] is from 20:1 to 10:1.

The fifth embodiment includes a method where the 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 beet, soybean, cotton, pineapple, in pastures, meadows, pastures, fallow land, turfgrass, tree and vineyards, aquatic environments, industrial vegetation control (IVM) sites or rights-of-way (ROW).

A sixth embodiment includes a method wherein (a), (b) and (c) are applied pre-emergence to a weed or crop.

A seventh embodiment includes a method wherein control of unwanted vegetation can be achieved in crops tolerant to glyphosate, 5-enolpyruvylshikimate-3-phosphate synthase (EPSP) inhibitor, glufosinate, glutamine synthetase inhibitor, dicamba, phenoxyauxin, pyridyloxyauxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl-CoAcarboxylase (ACCase) inhibitor, imidazolinone, sulfonylurea, pyrimidinylthiobenzoate, triazolopyrimidine, sulfonylaminocarbonyltriazolinone, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor ), 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor, phytoene desaturase inhibitor , carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase inhibitor (PPO), 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, protoporphyrinogen oxidase inhibitor (PPO ), triazine or bromoxynil.

An eighth embodiment includes a method wherein the hardy crop has multiple or stacked traits conferring tolerance to multiple herbicides or multiple modes of action.

A ninth embodiment includes a method wherein the unwanted vegetation includes a weed with resistance or tolerance to a herbicide.

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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 percent, for example, approximately 1.0 covers values from 0.9 to 1.1.

As used herein, halauxifenemethyl (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:

The compound 2,4-D used herein is 2-(2,4dichlorophenoxy)acetic acid and has the following structure:

Exemplary uses of 2,4-D are described in Tomlin, C, ed. A World Compendium The Pesticide Manual. 15 ^th ed. Alton: BCPC Publications, 2009 (hereinafter referred to in this document as The Pesticide Manual, Fifteenth Edition, 2009).

Exemplary uses of 2,4-D include its use for post-emergence control of annual and perennial broadleaf weeds, for example, in grain crops, maize, sorghum, grasslands, established grass turf, grass crops, orchards, cranberry species, asparagus, sugarcane , rice fields and on land not used for agriculture. Exemplary chemical forms of 2,4-D include salt or ester forms, for example 2,4-D EHE, which is 2-ethylhexyl-2-(2,4-dichlorophenoxy)acetate and has the following structure:

2,4-D DMA, which is 2-(2,4-dichlorophenoxy)acetic acid with Nmethylmethanamine and has the following structure:

WITH]

Saflufenacil as used herein is 2-chloro-5-[3,6-dihydro-3methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro^-[[methyl (1-methylethyl)amino]sulfonyl]benzamide and has the following structure:

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Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Illustrative uses of saflufenacil include its use for foliar and post-root control of broadleaf weeds.

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, such as 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 spray) 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

R^^R ⁴ ^, 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 optional is substituted with one or more hydroxy, C1- _C4 alkoxy, C1- _C4 alkylthio or phenyl groups, provided that ^R1 , ^R2 , ^R3 and ^R4 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.

Compositions and methods

Provided herein are herbicidal compositions containing a herbicidal effective amount of (a) halauxifen-methyl; (b) a second herbicide comprising 2,4-D DMA; and (c) a third herbicide comprising saflufenacil; where the weight ratio of the components [(a)+(b)] to [c] is from 20:1 to 10:1.

Also provided herein are methods for controlling unwanted vegetation, comprising the steps 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 composition comprising:

(a) halauxifenemethyl;

- 3 045664 (b) a second herbicide comprising 2,4-D DMA; and (c) a third herbicide comprising saflufenacil; where the weight ratio of the components [(a)+(b)] to [c] is from 20:1 to 10:1.

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 described herein can be used to control unwanted vegetation in glyphosate-tolerant, 5-enolpyruvylshikimate-3-phosphate synthase (EPSP) inhibitor-tolerant, glufosinate-tolerant, glutamine synthetase inhibitor, dicamba tolerant, phenoxyauxin tolerant, pyridyloxyauxin tolerant, auxin tolerant, auxin tolerant, auxin transport inhibitor tolerant, aryloxyphenoxypropionate tolerant, auxin tolerant to cyclohexanedione, tolerant to phenylpyrazoline, tolerant to acetyl-CoA carboxylase (ACCase) inhibitor, tolerant to imidazolinone, tolerant to sulfonylurea, tolerant to pyrimidinyl thiobenzoate, tolerant to thiazolpyrimidine, tolerant to to sulfonylaminocarbonyltriazolinone, tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor, tolerant to 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor, tolerant to phytoene desaturase inhibitor, tolerant to carotenoid biosynthesis inhibitor, tolerant to protoporphyrinogen oxidase (PPO) inhibitor, tolerant to cellulose biosynthesis inhibitor, tolerant to mitosis inhibitor, tolerant to microtubule assembly inhibitor, tolerant to very long chain fatty acid biosynthesis inhibitor, tolerant to fatty acid biosynthesis inhibitor and photosystem I inhibitor-tolerant, photosystem II inhibitor-tolerant, triazine-tolerant, and bromoxynil-tolerant lipids in crops (such as, but not limited to, soybean, cotton, canola/oilseed rape, rice, cereals , corn, sorghum, sunflower, sugar beet, sugar cane, turfgrass, etc.), for example, in combination with glyphosate, EPSP synthase inhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors , aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, ACCase inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule assembly inhibitors, inhibitors very long chain fatty acid biosynthesis, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines and bromoxynil. The compositions and methods can be used in the control of unwanted vegetation in crops having multiple or stacked traits that confer tolerance to multiple chemicals and/or inhibitors with multiple mechanisms of action.

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 insect restrictions, 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 structure).

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 grasshopper, 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 grass, ECHCV), Echinochloa colonum (L.) LINK (peacock barnyard grass, ESNSO), Echinochloa oryzoides (Ard.) Fritsch (rice barnyard grass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (bearded barnyard grass, ESNRN), Echinochloa phyllopogon (Stapf) Koso-Pol. (Rice barnyard grass, ESNRN), Echinochloa polystachya (Kunth) Hitchc. (multiple 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 squab, CYPES), Cyperus iria L. (spot iria, CYPIR), Cyperus rotundus L. (round squirrel, CYPRO), Cyperus serotinus Rottb./S.V. Clarke , CYPSE), Eleocharis spp. (ELOSS), Fimbristylis miliacea (L.) Vahl (fringeweed, 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 .), Jakq. (Ipomoea ivy, IPOHE), Lindernia dubia (L.) Pennell (LIDDU), Ludwigia spp. (LUDSS), Ludwigia linifolia Poir. (Ludwigia issopolis, 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 foxtail, SETVI), Amaranthus retroflexus (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

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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. (spurge, 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 (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. (split-flowered 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. (ragweed, AMBTR), Anoda cristata (L.) Schlecht. (anode comb, ANVCR), Asclepias syriaca L. (Syrian cottonweed, ASCSY), Bidens pilosa L. (hairy row, BIDPI), Borreria spp. (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (boreria winged, BOILF), Spermacose latifolia (boreria winged, BOILF), Chenopodium album L. (white pigweed, CHEAL), Cirsium arvense (L.) Scop. (field thistle, CIRAR), Commelina benghalensis L. (COMBE), Datura stramonium L. (Datura stramonium, 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. (common cocklebur, 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. (BELPE), Cyperus esculentus L. (CYPS), Cyperus spp. (CYPSS), Digitaria sanguinalis (L.), Scop. (blood red crabgrass, DIGSA), Diodia virginiana L. (DIQVI), Euphorbia spp. (Euphorbia, EPHSS), Glechoma hederacea L. (GLEHE), Hydrocotyle umbellata L. (money, HYDUM), spp. Kyllinga (KYLSS), Lamium amplexicaule L. (LAMAM), Murdannia nudiflora (L.), Brenan (MUDNU), Oxalis species (Oxalis, OXASS), Plantago major L. (Plantain, PLAMA ), Plantago lanceolata L. (PLALA), Phyllanthus urinaria L. (PYLTE), Rumex obtu- 6 045664 sifolius L. (sorrel, RUMOB), 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 administered at an application rate of from about 1 gram of active ingredient per hectare (g ai/ha) to about 70 grams (g ai/ha) based on the total amount of active ingredients in the composition. In certain embodiments, the composition is used at a dosage rate of about 4 g a. i./ha up to approximately 70 g a. i./ha in terms of the total amount of active ingredients in the composition. In some embodiments, the methods include contacting the unwanted vegetation or site thereof with halauxifen-methyl or a salt thereof and saflufenacil, or agriculturally acceptable salts, esters and amides thereof, or a salt or ester thereof, or applying them to to soil or water to prevent the emergence or growth of vegetation, for example sequentially or simultaneously. In some embodiments, saflufenacil or its agriculturally acceptable salts, esters and amides are used at a rate of about 1 g a. i./ha up to approximately 70 g a. i./ha, and halauxifen-methyl or its salt is used at a rate of approximately 1 g a. i./ha up to approximately 4 g a. i./ha. In some embodiments, saflufenacil or its agriculturally acceptable salts, esters and amides are used at a rate of about 17.5 g a. i./ha up to approximately 70 g a. i./ha, and the compound of formula (I) or its salt or ester is used at a rate of about 1 g a. i./ha up to approximately 4 g a. i./ha. In some embodiments, saflufenacil or its agriculturally acceptable salts, esters and amides are used at a rate of about 35 g a. i./ha up to approximately 70 g a. i./ha, and halauxifen-methyl or its salt is used at a rate of approximately 1 g a. i./ha up to approximately 4 g a. i./ha. In one embodiment, the methods use halauxifen-methyl and saflufenacil, where halauxifen-methyl is used at a rate of about 1 g a. i./ha up to approximately 4 g a. i./ha, and saflufenacil is used at a rate of approximately 1 g a. i./ha up to approximately 50 g a. i./ha. In certain embodiments, the methods and compositions use halauxifen methyl or a salt thereof in combination with saflufenacil or a salt thereof to control at least one of Conyza sumatrensis, Conyza canadensis, ERICA, Conyza bonariensis, , ERIBO) or other related species of small petals (Conyza spp, ERISS).

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.

In some embodiments, the compositions provided herein further comprise at least one agriculturally acceptable excipient or carrier. Suitable excipients or carriers should not be phytotoxic to valuable crops, in particular at the concentrations used when applying compositions for selective weed control in the presence of crops, and they should not react chemically with herbicidal components or other ingredients in composition composition. Such mixtures may be formulated for use directly on weeds or their habitats, or they may be concentrates or formulations that are typically diluted with additional carriers and excipients before use. They may be in the form of solids, such as, for example, dusts, granules, water-dispersible granules or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be provided in the form of a premix or tank mixture.

Agriculturally suitable excipients and carriers include, but are not limited to, crop aid oil concentrate;

- 7 045664 nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; a mixture of petroleum hydrocarbon, alkyl esters, organic acid and anionic surfactant; C ₉ -C ₁₁ alkyl polyglycoside; phosphoric acid alcohol ethoxylate; natural primary alcohol ethoxylate (C ₁₂ -C ₁₆ ); 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 solvents include, but are not limited to, 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), 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, etc.

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 wt%. 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 embodiments, such embodiment compositions are diluted with an inert carrier, such as water, before use. 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 wt.% and in certain embodiments in an amount from about 0.01 to 1 ,0 wt.%.

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 bed in a ratio of 80 to 20. The soil base was placed in 1 quart plastic pots with a surface area of 83.6 cm ² . 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® 155-15 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 halauxifene methyl esters (methyl 4amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate), each formulated as a SC (suspension concentrate), and different herbicidal components individually and in combination. The form of the compound of formula I was used on an acid equivalent basis.

The form of the test compound of formula I included

NH-

halauxifenemethyl

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 stock 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 solutions for sprays contained 1.25±0.05 vol./vol.% of oil concentrate for agricultural crops.

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. mixtures

- 9 045664 acetone/DMSO 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 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 1.5 v/v% crop oil concentrate so that the final solutions for spraying contained 1.25 v/v% of oil concentrate for agricultural crops. 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. Application solutions were prepared by adding 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 contained 1.25% v/v of 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 to an application area of 0.503 m ² at a spray height of 18-20 inches (46-20 inches). 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 compounds tested, application rates used, plant species tested and results are shown in the table.

The table shows weed control by foliar application of compositions containing halauxifen-methyl + 2,4-O-dimethylammonium (2,4-D-DMA) + saflufenacil to various broadleaf weeds. The table demonstrates that the use of a premix (chemical 1; 3.8 g eq/ha/L halauxifen methyl + 520.4 g eq/ha/L 2,4-D DMA) in an amount of 654 .99 g a. i./ha and saflufenacil 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, saflufenacil 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.

- 10 045664

Table. Results of control of ERISU weed populations (Conyza sumatrensis, Sumatran small petal) on the indicated days after application (DAA) using tank mixtures of halauxifen methyl + 2,4-D dimethylammonium (2,4-D DMA) + saflufenacil

ω S to C and to about S 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 medium, weed control Combined actual avg. % Weed control Combined forecast. avg. % weed control Number of observations 1 1 ERISU 17 DAA Galauxifen methyl+2,4-D dimethylammonium 654.99 35.00 Saflufen cil 49 52.50 82.50 68.62 4 0.031 1 ERISU 28 DAA Galauxifen methyl+2,4-D dimethylammonium 654.99 61.25 Saflufen cil 49 66, 25 100.00 86.81 4 0.004 1 ERISU 43 DAA Galauxifen methyl+2,4-D dimethylammonium 654.99 71.25 Saflufen cil 49 77.50 100.00 93.50 4 0.007 2 ERISU 17 DAA Galauxifen methyl+2,4-D dimethylammonium 654.99 36.25 Saflufen cil 49 66, 25 95.00 78.56 4 0.002 2 ERISU 28 DAA Galauxifenmethyl+2,4-D 654.99 48.75 Saflufen cil 49 97.50 98.25 98.69 4 0.766 dimethylammonium 2 ERISU 43 DAA Galauxifen methyl+2,4-D dimethylammonium 654.99 74.50 Saflufen cil 49 98.25 100.00 99.45 4 0.278

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 (9)

1. Herbicidal composition containing a herbicidal effective amount of: (a) halauxifenemethyl; (b) a second herbicide comprising 2,4-D DMA; and (c) a third herbicide comprising saflufenacil; where the weight ratio of the components [(a)+(b)] to [c] is from 20:1 to 10:1. 2. The composition of claim 1, further comprising an agriculturally acceptable excipient or carrier. 3. The composition according to claim 1 or 2, further comprising at least one herbicide antidote. 4. A method of controlling unwanted vegetation, comprising the steps 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 composition comprising: (a) halauxifenemethyl; (b) a second herbicide comprising 2,4-D DMA; and (c) a third herbicide comprising saflufenacil; where the weight ratio of the components [(a)+(b)] to [c] is from 20:1 to 10:1. 5. The method according to claim 4, 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, types of oats, rye, sorghum, corn/maize, sugar cane , sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, meadows, pastures, fallow land, lawn grass, tree and vineyards, aquatic environments, industrial vegetation control (IVM) or right-of-way (ROW). 6. The method according to claim 4 or 5, where (a), (b) and (c) are applied before emergence to a weed or crop. 7. Method according to any one of claims 4-6, where control of unwanted vegetation is carried out in rural areas - 11 045664 agricultural crops tolerant to glyphosate, 5enolpyruvylshikimate-3-phosphate synthase inhibitor (EPSP), glufosinate, glutamine synthetase inhibitor, dicamba, phenoxyauxin, pyridyloxyauxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, an acetyl-inhibitor CoA carboxylase (ACCase), imidazolinone, sulfonylurea, pyrimidinylthiobenzoate, triazolopyrimidine, sulfonylaminocarbonyltriazolinone, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor, phytoene desaturase inhibitor, caro biosynthesis inhibitor tinoids, protoporphyrinogen oxidase inhibitor (PPO), cellulose biosynthesis inhibitor, mitosis inhibitor, microtubule assembly inhibitor, very long chain fatty acid biosynthesis inhibitor, fatty acid lipid biosynthesis inhibitor, photosystem I inhibitor, photosystem II inhibitor, triazine or bromoxynil. 8. The method of claim 7, wherein the hardy crop has multiple or stacked traits conferring tolerance to multiple herbicides or multiple mechanisms of action. 9. The method according to any one of claims 4 to 8, wherein the unwanted vegetation includes a weed with resistance or tolerance to the herbicide.