herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxyphenyl)

专利摘要:
COMPOSITIONS OF HERBICIDES UNDERSTANDING 4-AMINO-3-CHLORINE-5-FLUORO-6- (4-CHLORINE-2- FLUORO-3-METOXYphenyl) ACID PYRIDINE-2-CARBOXYLIC OR ITS DERIVATIVE FROM SAME AND GLYPHOSATE OR GLUFOSINATE. The present invention relates to synergistic herbicide compositions containing and method for controlling undesirable vegetation using (a) a compound of formula (I): or an agriculturally acceptable salt ester and (b) glufosinate-ammonium, glyphosate -dimethylammonium, glyphosate-isopropylammonium. glyphosate, glufosinate and glyphosate trimesium or an agriculturally acceptable derivative thereof. The methods and compositions here allow control of undesirable vegetation, for example, in directly grown rice, rice grown in water and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, green corn / maize, sugar cane, sunflower, rapeseed, canola, beet, soy, cotton, pineapple, pastures, fields, pastures, idle land, grass, trees and orchards, aquatic plants, industrial vegetation management (Industrial Vegetation Management - IVM) or easements (Rights-Of-Way - ROW). 1/1
公开号:BR102013018645B1
申请号:R102013018645-7
申请日:2013-07-22
公开日:2020-10-27
发明作者:Carla Yerkes；Richard Mann；Paul Schmitzer
申请人:Dow Agrosciences Llc；
IPC主号:

专利说明:

Priority Claim
[001] This Application claims the benefit of Provisional Patent Application number US 61 / 675,083, filed on July 24, 2012, and Patent Application serial number US 13 / 836,653, deposited on March 15, 2013, the description of each of which is incorporated herein by reference in full. Field
[002] Herbicidal compositions comprising and methods for controlling undesirable vegetation using (a) 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxy) acid are provided herein - phenyl) pyridine-2-carboxylic or an agriculturally acceptable ester or salt thereof and (b) glyphosate or glufosinate or an agriculturally acceptable ester or salt thereof. Background
[003] The protection of crops against weeds and other vegetation which inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in controlling this unwanted growth. Chemical herbicides of many types have been described in the literature and a large number are in commercial use. However, there remains a need for compositions and methods that are effective in controlling undesirable vegetation. summary
[004] A first embodiment of the invention provided here includes herbicidal compositions comprising a herbicidally effective amount of (a) a compound of Formula (I)

[005] or an agriculturally acceptable salt or ester thereof, and (b) selected from the group consisting of glyphosate and glufosinate or an agriculturally acceptable salt or ester thereof.
[006] A second embodiment includes mixing the first modality in which Formula (I) is present in the form of at least one of the following forms: a carboxylic acid, a carboxylate salt, an aralkyl ester, an alkyl ester, a unsubstituted benzyl ester, substituted benzyl ester, C1-4 alkyl ester and / or n-butyl ester.
[007] A third embodiment includes mixtures according to any of the first or second embodiments in which (b) is glyphosphate or an agriculturally acceptable salt or ester thereof, wherein the weight ratio of the compound of Formula (I ) for glyphosate or salt or ester thereof is supplied in units of gae / ha for gai / ha or gae / ha for gae / ha and is selected from the group of ranges of proportions and proportions consisting of about: 1 : 1120 to 3.1, 1: 852 to 10.1, 1: 509 to 1: 3, 1: 280 to 1: 7, 1:29, 1:14, 1:57, 1: 7, 1:24 , 1:12, 1:48, 1: 6, 1:96, 1:19, 1:26, 1:13, 1:28, 1:56, 1: 105, 1: 52,5, 1:64 , 1: 127, 1: 210, 1: 112, 1: 255, 1: 420, 1: 509, 1: 800 or within any defined range between any two of the preceding values.
[008] A fourth embodiment includes mixtures according to any one of the first or second embodiments in which (b) is glu-phosinate or an agriculturally acceptable salt or ester thereof, wherein the weight ratio of the compound of Formula (I ) for glufosinate or a salt or ester thereof is supplied in units of gae / ha for gai / ha or gae / ha for gae / ha and is selected from the group of ranges of proportions and proportions consisting of about: 1: 780 to 11: 1, 1: 271 to 1: 1, 1: 125 to 1: 3, 1:31, 1: 15.5, 1:15, 11: 1, 1:62, 1: 7,7, 1: 39, 1:14, 1: 7, 1: 3,5, 1: 3,8, 1: 1,9, 1: 7,5, 1:72, 1:34, 1:18, 1: 145, 1: 72,3, 1:36, 1: 112, 1:56, 1: 112,5, 1:28, 1: 7, 1: 225 or within any defined range between any two of the preceding values.
[009] A fifth embodiment includes any composition according to any one of the first to fourth embodiments, wherein the mixture further comprises at least one agriculturally acceptable agent selected from the group consisting of an adjuvant, a vehicle or a sunscreen.
[0010] A sixth modality includes methods of controlling undesirable vegetation comprising the stage of application or otherwise contact of vegetation and / or soil and / or water with a herbicidally effective amount of at least one mixture according to any one of the first to fifth modalities.
[0011] A seventh modality includes methods according to the sixth modality in which the method is practiced in at least one member of the group consisting of rice directly grown, grown in water and / or transplanted, cereals, wheat, barley, oats, rye , sorghum, green corn / maize, sugar cane, sunflower, rapeseed, canola, beet, soy, cotton, pineapple, pasture, fields, pasture, idle land, lawns, trees and orchards, aquatic plants, crops, vegetables, management industrial vegetation (Industrial Vegetation Management - IVM) or rights of way (Rights-Of-Way - ROW).
[0012] An eighth modality includes methods according to any of the sixth and seventh modalities, in which a herbicidally effective amount of the mixture is applied pre- or post-emergently to at least one of the following: a crop, a field, an ROW or a rice field.
[0013] A ninth modality includes methods according to any of the sixth to eighth modalities, in which undesirable vegetation can be controlled in: glyphosate-tolerant crops, 5-chiquimatoenolpyruvylchiquimato-3-phosphate synthase (5- EnolPyruvylShikimate- 3-Phosphate - EPSP), glufosinate, glutamine synthase inhibitor, dicamba, phenoxy auxin, pyridyloxy auxin, synthetic auxin, auxin transport inhibitor, aryloxy phenoxy propionates, cyclohexanedione, phenylpyrazoline, acetyl CoA carboxylase inhibitor (Acetyl CoA Carboxylase - ACCase), imidazolinone, sulfonylurea, pyrimidinylthiobenzoate, triazolopyrimidine, sulfonylaminocarbonyltriazolinone, acetolactate synthase inhibitor (AcetoLactate Synthase - ALS) or acetohydroxy acid oxide synthase (AcidHydroxy acid) (AcidHydroxy acid) 4-hydroxyphenyl-pyruvate (4-HydroxyPhenyl-Pyruvate-Di oxygen ase - HPPD), phytoene desaturase inhibitor, carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase inhibitor (ProtoPorphyrinogen Oxidase - PPO), cellulose biosynthesis inhibitor, mitosis inhibitor, microtubule inhibitor, very long chain fatty acid inhibitor, lipid and fatty acid biosynthesis inhibitor, photosystem I inhibitor , photosystem II inhibitor, triazine or bromoxynil.
[0014] The tenth modality includes at least one method according to any of the sixth to ninth modalities, in which a plant that is resistant or tolerant to at least one herbicide is treated and where the resistant or tolerant crop has stacked or multiple features that confer tolerance to multiple herbicides or inhibitors of multiple modes of herbicidal action. In some modalities, the treated plant that expresses resistance or tolerance to a herbicide is undesirable vegetation itself.
[0015] An eleventh modality includes methods according to the eleventh modality, in which the resistant or tolerant weed is a biotype with resistance or tolerance to multiple herbicides, multiple chemical classes, inhibitors of multiple modes of herbicidal action or via multiple resistance mechanisms.
[0016] A twelfth modality includes at least one of the methods according to the eleventh or eleventh modality, in which the resistant or tolerant unwanted plant is a resistant or tolerant biotype to at least one or more modes of action consisting of: acetolactate synthase inhibitors (AcetoLactate Synthase - ALS) or acetohydroxy acid synthase inhibitors (AceHydroxy Acid Synthase - AHAS), photosystem II inhibitors, acetyl-CoA carboxylase inhibitors (Acetyl ÇoA Carboxylase - ACCase) , synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylchiquimate-3-phosphate synthase inhibitors (5-EnolPyruvylShikimate-3-Phosphate - EPSP), microtubule assembly inhibitors, lipid synthesis inhibitors and fatty acids, protoporphyrinogen oxidase inhibitors (ProtoPorphyrinogen Oxidase - PPO), carotenoid biosynthesis inhibitors, very long chain fatty acid inhibitors (Very Long Ch ain Fatty Acid - VLCFA) inhibitors, phytoene desaturase inhibitors (Phytoene DeSaturase - PDS), protease inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate (4-HydroxyPhenyl-Pyruvate-Dioxygenase) dioxigenase inhibitors - HPPD , cell division inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes of action, quinclorac, arylaminopropionic acids, difenzoquat, endothal or organoarsenic.
[0017] A thirteenth modality includes methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the third modality, in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha, glyphosate or a glyphosate salt or ester selected from the group of rates consisting of about: 124.5, 249, 105, 210, 420, 280, 377, 560, 840, 1120, 2240, 25, 50, 75, 100 or within any defined range between any two of the preceding values.
[0018] A fourteenth modality includes methods according to any one of the third and thirteenth modalities, in which the controlled plant is at least one plant selected from the group consisting of: ECHCG, ECHCO, LEFCH, CYPDI, IPOHE, DIGSA, ECHCG, SCPMA, SORHA, VIOTR, SETFA, CHEAL, CYPES, POLCO and AVEFA and still other modalities include plant control of the genera consist of Echinochloa, Leptochloa, Cyperus, Ipomoea, Digitaria, Echinochloa, Schoenoplectus, Viola, Setaria, Chenopodium, Cyop , Polygonum and Avena.
[0019] A fifteenth modality includes methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the fourth modality, in which the amount of the mixture is applied at a rate, expressed in gai / ha or gae / ha, of glufosinate or an agriculturally acceptable salt or ester thereof selected from the group of rates consisting of about: 25, 28.3, 56.5, 113, 271, 542, 135.5, 112.5, 225, 450, 1560 or in any range defined between any two of the preceding values.
[0020] A sixteenth modality includes methods according to any of the fourth and fifth modalities, in which the controlled plant is at least one plant selected from the group consisting of: DIGSA, ECHCG, ECHCO, CYPDI, LEFCH, IPOHE , AVEFA, ELEIN, SORHA, CIRAR, AMARE, CHEAL, CYPES and SETFA, yet other modalities include control of plants of the genera that consist of: Digitaria, Echinochloa, Leptochloa, Ipomoea, Avena, Eleusine, Sorghum, Cirsium, Amaranthus, Chenopodium, Cyperus and Setaria.
[0021] Herbicidal compositions comprising a herbicidally effective amount of (a) a compound of Formula (I) are provided herein

[0022] or an agriculturally acceptable salt or ester thereof and (b) glyphosate or glufosinate or an agriculturally acceptable salt or ester thereof. The compositions may also contain an agriculturally acceptable adjuvant or vehicle.
[0023] Methods of controlling undesirable vegetation comprising application of (a) a compound of Formula (I) or an agriculturally acceptable salt or ester thereof and (b) glyphosate or glufosinate or an agriculturally acceptable salt or ester of the same. Detailed Description DEFINITIONS
[0024] As used here, the compound of Formula (I) has the following structure:

[0025] The compound of Formula (I) can be identified by the name of 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methoxyphenyl) -5-fluorpyridine-2-carboxylic acid and was described in North American Patent 7,314,849 (B2), which is incorporated herein by reference in its entirety. Exemplary uses of the Formula (I) compound include control of undesirable vegetation, including grass, broadleaved weeds and rush, in multiple crop and other situations.
[0026] Glufosinate is 2-amino-4- [hydroxy (methyl) phosphinoyl] - butyric acid. An exemplary form of glufosinate is ammonium glufosinate, the ammonium salt of glufosinate. It can be referred to as 2-amino-4- (hydroxymethylphosphinyl) butanoic acid monoammonium salt and has the following structure:

[0027] Other chemical forms of glufosinate (or phosphinothricin) include bialaphos, which is 2-amino-4- (methylphosphino) butyrylalanylalanine and has the following structure:

[0028] Bialaphos can also be used in the form of salt, such as sodium bialaphos.
[0029] Exemplary uses are described in Tomlin, C. & Ed. A World Compendium The Pesticide Manual. 15th Ed. Alton: BCPC Publications, 2009 (hereinafter "The Pesticide Manual, Fifteenth Edition, 2009"). Exemplary uses include its use to control broadleaf weeds and annual and perennial grasses. Other chemical forms include glufosinate-P, that is, S-2-amino-4- [hydroxy (methyl) phosphinoyl] butyric acid.
[0030] As used here, glyphosate is N- (phosphonomethyl) glycine and has the following structure:

[0031] Exemplary uses of glyphosate are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of glyphosate include its use for the control of broadleaf weeds and annual and perennial grasses. Other forms of glyphosate include its dimethylammonium salt, dimethylamino salt, isopropyl ammonium salt, trimesium (sulfosate) salt, monoammonium salt, diamonium salt, potassium salt and sesqui-sodium salt.
[0032] As used here, herbicide means a compound, for example, an active ingredient, which kills, controls or otherwise adversely modifies the growth of plants.
[0033] As used here, an amount herbicidally effective or for vegetation control is an amount of active ingredient which causes a modifying effect adversely to the vegetation, for example, causes deviations from natural development, death, performs regulation, causes drought, causes delay and the like.
[0034] As used here, control of undesirable vegetation means avoiding, reducing, killing or otherwise adversely modifying the development of plants and vegetation. Methods for controlling undesirable vegetation by applying certain combinations of herbicides or compositions are described here. Application methods include, but are not limited to, applications to the vegetation or its location, for example, application to the area adjacent to the vegetation, as well as pre-emergence, post-emergence, foliar application methods (diffusion, directed, banded , point, mechanics, overhead or rescue) and water applications (above-water and submerged vegetation, diffusion, point, mechanics, injected into water, granular diffusion, granular point, bottle with agitator or spray stream) manual, by backpack, machine, tractor or aerial (plane and helicopter).
[0035] As used here, plants and vegetation include, but are not limited to, germinating seeds, seedlings in emergence, plants that emerge from vegetative propagules, immature vegetation and established vegetation.
[0036] As used herein, salts and esters acceptable in agriculture refers to salts and esters that exhibit herbicidal activity or that are or can be converted to the herbicide mentioned in plants, soil or water. Examples of esters acceptable in agriculture are those that are or can be hydrolyzed, oxidized, metabolized or otherwise converted, for example, in plants, water or soil, to the corresponding carboxylic acid which, depending on the pH, can be in dissociated or non-dissociated form.
[0037] Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium and amine cations of the Formula: R1R2R3R4N +
[0038] wherein R1, R2, R3 and R4 each independently represent hydrogen or C1-C12 alkyl, C3-C12 alkenyl or C3-C12 alkynyl, each of which is optionally substituted by 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 R1, R2, R3 and R4 together can represent an aliphatic difunctional portion containing 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, with an amine, such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisalylamine, 2-butoxyethylamine, morpholine, cyclodedecylamine or benzylamine or with a tetra alkyl ammonium hydroxide, such as tetra methyl ammonium hydroxide or choline hydroxide.
Exemplary esters include those derived from C1-C12 alkyl-, C3-C12 alkenyl-, C3-C12 alkynyl- or C7-C10 aryl-substituted alkyl alcohols, such as methyl alcohol, isopropyl alcohol, 1-butanol, 2- ethylhexanol, butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or benzyl alcohols not substituted or substituted. Benzyl alcohols can be substituted by 1-3 substituents selected independently from halogen, C1-C4 alkyl or C1-C4 alkoxy. Esters can be prepared by coupling the acids with 0 alcohol using any variety of suitable activating agents, such as those used for peptide couplings, such as dicyclohexylcarbodiimide (DiÇyclohexylylcarbodiimide - DCC) or carbonyl diimidazole (Carbonyl Dilmidazole - CDI); by reacting the 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 corresponding acid chloride of an acid with an appropriate alcohol; by reacting the corresponding acid with an appropriate alcohol in the presence of an acid catalyst; or by means of transesterification. COMPOSITIONS AND METHODS
[0040] Herbicidal compositions are provided here comprising a herbicidally effective amount of (a) a compound of Formula (I)

[0041] or an agriculturally acceptable salt or ester thereof and (b) glufosinate or glyphosate or agriculturally acceptable salts or esters thereof.
[0042] Unwanted vegetation control methods comprising contact with vegetation or its location, that is, the area adjacent to the vegetation, with or application to the soil or water to prevent the emergence or growth of vegetation of an amount, are also provided here herbicidally effective compound of Formula (I) or agriculturally acceptable salt or ester thereof and (b) glufosinate or glyphosate or agriculturally acceptable salts or esters thereof. In certain embodiments, the methods employ the compositions described here.
[0043] Furthermore, in some embodiments, the combination of compound (I) or an agriculturally acceptable salt or ester thereof and glyphosate or glufosinate herbicides or an agriculturally acceptable salt or ester thereof exhibits synergism, for example, the active herbicidal ingredients they are more effective in combination than when applied individually. Synergism was defined as "an interaction of two or more factors in such a way that the effect, when combined, is greater than the effect predicted based on the response of each factor applied separately". Senseman, S. Ed. Herbicide Handbook. 9th Ed. Lawrence: Weed Science Society of America, 2007. In certain modalities, the compositions exhibit synergy, as determined by Colby's equation. Colby, S.R. 1967. Calculation of The Synergistic and Antagonistic Response of Herbicide Combinations. Weeds 15: 20-22.
[0044] In certain embodiments of the compositions and methods described here, the compound of Formula (I), that is, the carboxylic acid, is employed. In certain embodiments, a carboxylate salt of the compound of Formula (I) is employed. In certain modalities, an aralkyl or alkyl ester is employed. In certain embodiments, a benzyl ester, substituted benzyl ester or C1-4 alkyl ester, for example, n-butyl ester, is used. In certain modalities, benzyl ester is used.
[0045] In some embodiments, the compound of Formula (I) or salt or ester thereof and glufosinate or glyphosate or an agriculturally acceptable salt or ester thereof are formulated in a composition, mixed in a tank, applied simultaneously or applied sequentially .
[0046] Herbicidal activity is exhibited by the compounds when they are applied directly to the plant or to the location of the plant at any stage of growth. The observed effect depends on the plant species to be controlled, the plant's growth stage, the application parameters, the dilution and spray droplet size, the particle size of solid components, the environmental conditions at the time of use, the specific compound used, the specific adjuvants and vehicles used, the type of soil and the like, as well as the amount of chemical product applied. These and other factors can be adjusted to promote selective or non-selective herbicidal action. In some embodiments, the compositions described here are applied as a pre-emergence application, post-emergence application or water application in flooded rice fields or bodies of water (for example, ponds, lakes and streams), to relatively immature undesirable vegetation , for maximum weed control.
[0047] In some embodiments, the compositions and methods provided here are used to control weeds in crops including, but not limited to, rice directly grown, grown in water and / or transplanted, cereals, wheat, barley, oats, rye , sorghum, green corn / maize, sugar cane, sunflower, rapeseed, canola, beet, soy, cotton, pineapple, pasture, fields, pasture, idle land, lawns, trees and orchards, aquatic plants, crops, vegetables, management industrial vegetation (Industrial Vegetation Management - IVM) or rights of way (Rights-Of-Way - ROW).
[0048] In certain embodiments, the compositions and methods provided here are used to control weeds in rice. In certain modalities, rice is rice directly grown, grown in water and / or transplanted.
[0049] The compositions and methods described here can be used to control undesirable vegetation in glyphosate-tolerant crops, tolerant to a 5-enolpyruvylchiquimate-3-phosphate (5-EnolPyruvylShikimate-3-Phosphate - EPSP) synthase inhibitor, tolerant to glufosinate, tolerant to a glutamine synthase inhibitor, tolerant to dicamba, tolerant to phenoxy auxin, tolerant to pyridyloxy auxin, tolerant to synthetic auxin, tolerant to an auxin transport inhibitor, tolerant to phenoxy aryloxy propionates, tolerant to cyclohexanedione , phenylpyrazoline tolerant, tolerant to an acetyl CoA carboxylase inhibitor (Acetyl ÇoA Carboxylase - ACCase), imidazolinone tolerant, sulphonylurea tolerant, pyrimidinylthiobenzoate tolerant, triazolopyrimidine tolerant, a tolerant to a sulfonyl acetate and a tolerant to a sulfonyl acetate. (AcetoLactate Synthase - ALS) or acetohydroxy acid synthase (AcetoHydroxy Ac id Synthase - AHAS), tolerant to a 4-hydroxyphenyl-pyruvate dioxigenase inhibitor (4-HydroxyPhenyl- Pyruvate-Di oxygenase - HPPD), tolerant to a phytene desaturase inhibitor, tolerant to a carotenoid biosynthesis inhibitor, tolerant to a protoporphyrinogen oxidase inhibitor (ProtoPorphyrinogen Oxidase - PPO), tolerant to a cellulose biosynthesis inhibitor, tolerant to a mitosis inhibitor, tolerant to a microtubule inhibitor, tolerant to a very long chain fatty acid inhibitor, tolerant to a lipid and fatty acid biosynthesis inhibitor, tolerant to a photosystem I inhibitor, tolerant to a photosystem II inhibitor, tolerant to triazine or tolerant to bromoxynil (such as, but not limited to, soy, cotton, canola / rapeseed) oily seed, rice, cereals, corn, sorghum, sunflower, sugar beet, sugar cane, peat, etc.), for example, together with glyphosate, EPSP synthase inhibitors, glufosinate, inhibitor s of glutamine synthetase, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxy phenoxy propionates, cyclohexanediones, phenylpyrazolines, ACCase inhibitors, imidazolinones, sulfonylurines, pyrimidinylthiozolinones, trinidinylsilaminolines , ALS or AHAS inhibitors, HPPD inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, inhibitors of lipid and fatty acid biosynthesis, inhibitors of photosystem I, inhibitors of photosystem II, triazines and bromoxynil.
[0050] The compositions and methods can be used to control undesirable vegetation in crops presenting multiple or stacked traits that confer tolerance to multiple chemicals and / or inhibitors of multiple modes of action. In some embodiments, the compound of Formula (I) or salt or ester thereof and complementary herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop to be treated and which complement the spectrum of weeds controlled by these compounds at the application rate used. In some embodiments, the compositions described here and other complementary herbicides are applied at the same time, either as a combined formulation, as a tank mix or sequentially.
[0051] The compositions and methods can be used to control undesirable vegetation in crops presenting multiple or stacked traits that confer tolerance to various chemicals and / or inhibitors of multiple modes of action. In some modalities, the compound of Formula (I) or salt or ester thereof and the complementary herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop to be treated and that complement the spectrum of weeds controlled by these compounds at the rate of application used. In some embodiments, the compositions described here and other complementary herbicides are applied at the same time or as a combined formulation, such as a tank mix or sequentially.
[0052] The compositions and methods that can be used in the control of undesirable vegetation in crops showing signs of tolerance to agronomic stress (including, but without limitation, drought, cold, salt, water, nutrients, fertility, pH), tolerance to pra -gas (including, but not limited to, insects, fungi and pathogens) and crop improvement (including, but not limited to, protein, carbohydrate or oil content; protein, carbohydrate or oil composition; plant stature and plant architecture) .
[0053] The compositions and methods provided here are used to control undesirable vegetation. Undesirable vegetation includes, but without limitations, undesirable vegetation that occurs in rice directly cultivated, grown in water and transplanted, cereals, wheat, barley, oats, rye, sorghum, corn / maize, sugar cane, sunflower, rapeseed, canola, beet, soy, cotton, pineapple, pastures, fields, pastures, idle land, lawns, trees and orchards, aquatic plants, crops, vegetables, industrial vegetation management (Industrial Vegetation Management - IVM) or rights of way (Rights- Of-Way - ROW). In some embodiments, the methods provided here are used to control undesirable vegetation in rice. In certain embodiments, the undesirable vegetation is Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf brachiaria, BRAPP), Digitaria sanguinalis (L.) Scop. (large mattress grass, DIGSA), DIGSA species), Echino-chloa species (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (rice grass, ECHCG), Echinochloa crus-pavonis (Kunth) Schult, (Gulf jute, ECHCV), Echinochloa colonum (L.) LINK (rice grass, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (aquatic grass early, Echor), Echinochloa oryzicola (Vasinger) Vasinger (late water grass, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (rice grass, ECHPH), Echinochloa polystachya (Kunth) Hitchc. (crisp river grass, ECHPO), Ischaemum rugosum Salisb. (male grass, ISCRU), Leptochloa chinensis (L.) Nees (Chinese mimoso grass, LEFCH), Lep- tochloa fascicularís (Lam.) Gray (bearded mimoso grass, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazon grass, LEFPA), Oryza species (red and weed rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (millet, PANDI), Paspalum dila- tatum Poir. (honeygrass, PASDI), Rottboellia cochinchinensis (Lour.) W.D. Clayton (camalote grass, ROOEX), Cyperus species (CYPSS), Cyperus difformis L. (small-flowered sedge, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (yellow sedge, CYPES), Cyperus would L. (flat rice sedge, CYPIR), Cyperus rotundus L. (purple tiririca, CYPRO), Cyperus serotinus Rottb./CBClarke (tiririca swamp flat, CYPSE), Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (cuminho, FIMMI), Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb. (Japanese reed, SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus L. Lye (aquatic reed, SCPMA), Schoenoplectus mucronatus L. (rice field reed, SCPMU), Aeschynomene species (angiquinho, AESSS), Alternanthera philoxeroides (Mart.) Griseb. (frog gut, ALRPH), Alisma plantago-aquatica L. (water plantain, ALSPA), Amaranthus species (carurus and amaranths, AMASS), Ammannia coccinea Rottb. (horse mackerel, AMMCO), Commelina benghalensis L. (trapoeraba, COMBE), Eclipta alba (L.) Hassk. (false American daisy, ECLAL), Heteranthera limosa (SW.) Willd./Vahl (deer-tongue, HETLI), Heteranthera reniformis R. & P. (marsh cress, HETRE), Ipomoea species de-viola, IPOSS), Ipomoea hederacea (L.) Jacq. (ivy-leaf viola string, IPOHE), Lindernia dubia (L.) Pennell (water-crested watercress, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia POIR. (primrose- willow of the southeast, LUDLI), Ludwigia octovalvis (Jacq.) Raven (primrose-willow of long fruits, LUDOC), Monochoria korsakowii Regel & Maack (monorail, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monorail, MOOVA), Murdannia nudiflora (L.) Brenan (muleina, MUDNU), Polygonum pensylvanicum L. (Pennsylvania buckwheat, POLPY), Polygonum persicaria L. (persicaria, POLPE), Polygonum hydropiperoides Michx. (POLHP, soft buckwheat), Rotala indica (Willd.) Koehne (Indian Itoothcup, ROTIN), Sagittaria species (aguape, SAGSS), Sesbania exaltata (Raf.) Cory / Rydb. Ex Hill (pigeon pea, SEBEX) or Sphenoclea zeylanica Gaertn. (majuba, SPDZE).
[0054] In some embodiments, the methods provided here are used to control undesirable vegetation on cereals. In certain modalities, the undesirable vegetation is Alopecurus myosuroides Huds. (foxtail, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oats, AVEFA), Bro- mus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz. (ema-cabecinha, PHAMI), Poa annua L. (dog-hair, POANN), Setaria pumila (Poir.) Roemer & J.A. Schultes (yellow vulpino, SETLU), Setaria viridis (L.) Beauv. (vulpino verde, SETVI), Amaranthus retroflexus L. (caruru, AMARE), Brassica species (BRSSS), Chenopodium album L. (common anthurium, CHEAL), Cirsium arvense (L.) Scop. (Canadian thistle, CIRAR), Galium aparine L. (peppermint love, GALAP), Kochia scoparia (L.) Schrad. (summer cypress, KCHSC), Lamium purpurreum L. (purple lamina, LAMPU), Matricaria recutita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.) Porter (wild chamomile, MATMT), Papaver rhoeas L. ( common poppy, PAPRH), Polygonum Convolvulus L. (wild wheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Sinapis species (SINSS), Sinapis arvenisis L. (wild mustard, SINAR), Stellaria media (L.) Vill. (common morugem, STEME), Veronica persica Poir. (lie, VERPE), Viola arvensis Murr. (field violet, VIOAR) or Viola tricolor L. (wild violet, VIOTR).
[0055] In some modalities, the methods provided here are used to control undesirable vegetation in the field and pasture, idle land, IVM and ROW. In certain modalities, the undesirable vegetation is Ambrosia artemisiifolia L. (common ambrosia, AM-BEL), Cassia obtusifolia (fedegoso, CASOB), Centaurea maculosa auct. non Lam. (painted brush, CENMA), Cirsium arvense (L.) Scop. (Canadian thistle, CIRAR), Convolvulus arvensis L. (field vine, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L. (leafy Christ's crown, EPHES), Serial-lactuca L./Torn. (prickly lettuce, LACSE), Plantago lanceolata L. (hardwood banana, PLALA), Rumex obtusifolius L. (sorrel, RUMOB), Sida spinosa L. (prickly guanxuma, SIDSP), Sinapis arvensis L. (wild mustard, SINAR ), Sonchus arvensis L. (perennial milkweed, SONAR), Solidago species (golden rod, SOOSS), Taraxacum officinale GH Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE) or Urtica dioica L. (common nettle, URTDI).
[0056] In some modalities, the methods provided here are used to control undesirable vegetation found in furrowed crops, trees and orchards and perennial crops. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (foxtail, ALOMY), Avena fatua L. (wild oats, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) R.D. Webster (Suriname grass, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) RD (grass beard, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) RD Webster (broadleaf brachiaria, BRAPP), Brachiaria plantaginea (Link) Hitchc . or Urochloa plantaginea (Link) R.D. Webster (marmalade grass, BRAPL), Cenchrus echinatus L. (southern grasshopper, CENEC), Digitaria horizontalis Willd. (Jamaican mattress grass, DIGHO), Digitaria insularis (L.) Mez ex Ekman (bitter grass, TRCIN), Digitaria sanguinalis (L.) Scop. (large mattress grass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (rice grass, ECHCG), Echinochloa colonum (L.) Link (rice grass, ECHCO), Eleusine indica (L.) Gaertn. (burdock, ELEIN), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (millet, PANDI), Panicum miliaceum L. (wild millet, PANMI), Setaria fabi Herrm. (giant vulpino, SETFA), Setaria viridis (L.) Beauv. (green vulpine, SETVI), Sorghum halepense (L.) Pers, (massambará grass, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (sorghum bicolor, SORVU), Cyperus esculentus L. (yellow sedge, CYPES), Cyperus rotundus L. (purple sedge, CYPRO), Abutilon theophrasti Medik. (mallow, ABUTH), Amaranthus species (carurus and amaranth, AMASS), Ambrosia artemisiifolia L. (common ambrosia, AMBEL), Ambrosia psilostachya DC. (western ambrosia, AMBPS), Ambrosia trifida L. (giant ambrosia, AMBTR), Anoda cristata (L.) Schlecht. (papua, ANVCR), Asclepias syriaca L. (common milkweed, ASCSY), Bidens piloosa L. (hairy black prick, BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (large-leaved hedge, BOILF), Spermacose latifolia (broad-leaved hedge, BOILF), Chenopodium album L. (common anthracite, CHEAL), Cirsium arvense (L.) Scop, (Canada thistle, CIRAR), Commelina benghalensis L. (tropical trapoeraba, COMBE), Datura stramonium L. (hell fig, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (wild peanuts, EPHHL) , Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden shrub, EPHHI), Euphorbia dentata Michx. (Crown-of-Christ, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy coniza, ERI-BO), Erigeron canadensis L. or Conyza canadensis (L.) Cronq. (Canadian coniza, ERICA), Conyza sumatrensis (Retz.) E. H. Walquer (tall coniza, ERIFL), Helianthus annuus L. (common sunflower, HELAN), Jac- Quemontia tamnifolia (L.) Griseb. (small-flowered viola string, IA-QTA), Ipomoea hederacea (L.) Jacq. (ivy leaf viola string, IPOHE), Ipomoea lacunosa L. (white viola string, IPOLA), Lactuca serriola L./Torn. (prickly lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Richardia species (purslane, RCHSS), Sida species (guanxuma, SIDSS), Sida spinosa L. (spiny guanxuma, SIDSP), Sinapis arvensis L. ( wild mustard, SINAR), Soanranum ptychanthum Dunal (eastern blackberry, SOLPT), Tridax procum- bens L. (bullgrass, TRQPR) or Xanthium strumarium L. (common thistle, XANST).
[0057] In some embodiments, the methods provided here are used to control unwanted grass vegetation. In some ways, the undesirable vegetation is Bellis perennis L. (English marl, BELPE), Cyperus esculentus L. (yellow sedge, CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L.) Scop. (big mattress grass, DIGSA), Diodia virginiana L. (Virginia hot herb, DIQVI), Euphorbia species (shrub, EPHSS), Glechoma hederacea L. (earth ivy, GLEHE), Hydrocotyle umbellata L. (dollar- silver, HYDUM), Kyllinga species (lemongrass, KYLSS), Lamium amplexicule L. (lamina, LAMAM), Murdannia nudiflora (L.) Brenan (muleína, MUDNU), Oxalis species (sorrel, OXASS), Plantago major L. (broad-leafed banana, PLAMA), Plantago lanceolata L. (leafy / narrow-leafed banana, PLALA), Phyllanthus urinaria L. (stone breaker, PYLTE), Rumex obtusifolius L. (sour-crimson , RUMOB), Stachys floridana Shuttlew. (Florida beton, STAFL), Stellaria media (L.) Vill. (common morugem, STEME), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE) or Viola species (wild violet, VIOSS).
[0058] In some embodiments, the compositions and methods provided here are used to control undesirable vegetation consisting of grass weeds, broadleaf weeds and reeds. In certain embodiments, the compositions and methods provided here are used to control undesirable vegetation, including Amaranthus, Avena, Chenopodium, Cirsium, Cyperus, Digitaria, Echinochloa, Eleusine, Ipomoea, Leptochloa, Polygonum, Setaria, Bol- boschoenus or Schoenoplectus, Sorghum and Viola.
[0059] In some embodiments, the combination of compound (I) or ester or agriculturally acceptable salt thereof and glyphosate or glufo-sinate or agriculturally acceptable salt or ester thereof is used to control Amaranthus retroflexus L. (caruru, AMARE), Avena fossa (wild oats, AVEFA), Chenopodium album L. (common anquinha, CHEAL), Cirsium arvense (L.) Scop (Canada thistle, CIRAR), Cyperus difformis L. (small flower curls, CYP-Dl), Cyperus esculentus L. (yellow sedge, CYPES), Digitaria sanguinalis (L.) Scop. (large mattress grass, DIGSA), Echinochloa crus-galli (L.) Beauv. (rice grass, ECHCG), Echinochloa colona (L.) Link (rice grass, ECHCO), Eleusine indica (L.) Gaertn. (burdock, ELEIN), Ipomoea hederacea Jacq. (ivy-leaf viola rope, IPOHE), Leptochloa chinensis (L.) Nees (Chinese honeygrass, LEFCH), Polygonum convolvulus L. (wild wheat, POLCO) Schoenoplectus maritimus (L.) Lye or Bolboschoenus maritimus (L.) Palia (aquatic reed, SCPMA), Setaria faberi Herrm. (giant vulpino, SETFA), Sorghum halepense (L.) Pers. (massambará grass, SORHA) and Viola tricolor L. (pansy, VIOTR).
[0060] The Formula I compound or an agriculturally acceptable salt or ester thereof can be used to control resistant or herbicide tolerant weeds. The methods that employ the combination of a Formula I compound or an agriculturally acceptable salt or ester thereof and the compositions described here can also be employed to control herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, resistant or tolerant biotype inhibitors of acetolactate synthase (AcetoLactate Syn-thase - ALS) or acetohydroxy acid synthase (AcetoHydroxy Acid Synthase - AHAS) (eg, imidazolinones, sulfonylureas) , triazolopyrimidines, pyrimidinylthiobenzoates, sulphonylaminocarbonyltriazolinones), photosystem II inhibitors (for example, phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, urea, nitriles, benzothiadiazines, carboxylases, acetylsylases - ACCase) (for example, aryloxy phenoxy propionates, cyclohexanediones, phenylpyrazolines), synthetic auxins (for example, benzoic acids, phenoxy carboxylic acids, pyridine carboxylic acids, quinoline carboxylic acids), auxin transport inhibitors (for example, phthalates) , semicarbazones), photosystem I inhibitors (e.g., bipyridyl) , 5-enolpyruvylchiquimate-3-phosphate synthase inhibitors (5-EnolPyruvylShikimate-3 Phosphate - EPSP) (eg glyphosate), glutamine synthase inhibitors (eg glufosinate, bialaphos), microtubule assembly inhibitors ( for example benzamides, benzoic acids, dinitroanilines, pyridines, phosphoramidates), mitosis inhibitors (eg carbamates), very long chain fatty acid inhibitors (VLCFA) (eg acetamides, chloroacetamides, oxyacetamides, tetrazolinones), inhibitors of the synthesis of lipids and fatty acids (for example, phosphorodithioates, thio-carbamates, benzofurans, chlorocarbonic acids), protoporphyrinogen oxidase inhibitors (ProtoPorphyrinogen Oxidase - PPO) (for example, diphenylses pheniftalimides, oxadiazoles, oxazolidinedines, phenylpyrazoles, pyrimidindiones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors (eg clomazone, amitrole, aclonifene), in phytoene desaturase (Phytoene DeSaturase - PDS) inhibitors (for example, starches, anilidex, furanones, phenoxybutan-amides, pyridiazinones, pyridines), 4-hydroxy-phenyl-pyruvate (4-HydroxyPhenyl-Pyruvate-Dioxigenase) dioxigenase inhibitors (eg calisthenones, isoxazoles, pyrazoles, tricetones), cellulose biosynthesis inhibitors (eg nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes of action, such as quinclorac and unclassified herbicides, such as arylaminopropionic acids, difenzoquat, endotal and organoarsenic acids. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes, biotypes with resistance or tolerance to herbicides with multiple modes of action and biotypes with multiple resistance mechanisms or tolerance (for example, resistance at the target site or metabolic resistance).
[0061] In some embodiments, an agriculturally acceptable ester or salt of compound (I) is used. In certain modalities, an agriculturally acceptable ester is employed. In certain embodiments, the ester is a C1-4 alkyl ester. In certain embodiments, the ester is an n-butyl ester. In certain embodiments, the ester is a benzyl ester. In certain embodiments, compound (I), which is a carboxylic acid, is employed.
[0062] In some embodiments, an agriculturally acceptable salt or ester of glyphosate or glufosinate is employed in the methods or compositions described here.
[0063] In certain embodiments of the compositions and methods described herein, the compound of Formula (I) or salt or ester thereof is used in combination with the herbicide glufosinate-ammonium or a salt thereof. In relation to the compositions, in some embodiments, the weight ratio of the compound of Formula I to 0 glufosinate-ammonium or a salt thereof is about 1: 780 to about 11:01. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl ester or n-butyl ester and glufosinate-ammonium. In some embodiments, the proportion by weight of the compound of Formula (I) or a benzyl ester thereof to glufosinate-ammonium is in the range of about 1: 780 to about 11:01. In certain embodiments, the weight ratio of the compound of Formula (I) or benzyl ester thereof to glufosinate-ammonium is in the range of about 1: 271 to about 1: 1. In a fashion, the composition comprises the compound of Formula I and glufosinate-ammonium, in which the weight ratio of the compound of Formula I to the herbicide glufosinate-ammonium is about 1: 2 to about 1: 145 . In one embodiment, the composition comprises the benzyl ester of the Formula I compound and glufosinate-ammonium, in which the weight ratio of the benzyl ester of the Formula I compound to the herbicide glufosynate-ammonium is about 1: 3, 5 to about 1: 225. In relation to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or its location or application to the soil or water to prevent the appearance or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of about 30 grams of acid equivalent per hectare (GAE / ha) and about 1,860 GAE / ha, based on the total amount of active ingredients in the composition. In certain modalities, the composition is applied at an application rate between about 31 grams of acid equivalent per hectare (GAE / ha) and about 574 GAE / ha, based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or its location or application to soil or water to prevent the appearance or growth of vegetation of a compound of Formula (I) or salt or ester thereof and glufosinate or a salt thereof , for example, sequentially or simultaneously. In some embodiments, glufosin-to-ammonium or a salt thereof is applied at a rate of about 28 GAE / ha and about 1560 GAE / ha and the compound of Formula (I), salt or ester thereof is applied in a level of about 2 GAE / ha to about 300 GAE / ha. In some embodiments, glufosinate-ammonium or a salt thereof is applied at a rate of about 14 GAE / ha and about 1120 GAE / ha and the compound of Formula (I), salt or ester thereof is applied in a level of about 1.5 g acid equivalent per hectare (GAE / ha) to about 100 GAE / ha. In some embodiments, glufosinate-ammonium or a salt thereof is applied at a rate of about 28 GAE / ha to about 542 GAE / ha and the compound of Formula (I), salt or ester thereof is applied in a rate of about 2 g acid equivalent per hectare (GAE / ha) to about 32 GAE / ha. In certain embodiments, the methods use the compound of Formula (I) or its benzyl ester and glufosinate-ammonium. In one embodiment, the methods use the benzyl ester of the Formula (I) compound and glufosinate-ammonium, in which the benzyl ester of the Formula (I) compound is applied at a rate of about 2 to about 32 GAE / ha and glu-phosinate-ammonium is applied at a rate of about 112 to about 545 GAE / ha. In one embodiment, the methods use the compound of Formula (I) and glufosinate-ammonium, where the compound of Formula (I) is applied at a rate of about 2 to about 32 GAE / ha and the herbicide glufosinate -ammonium is applied at a rate of about 28 to about 271 GAE / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in association with glufosinate-ammonium or a salt thereof are used to control SORHA, DIGSA, ECHCG, ECHCG, CYPDI, LEFCH, ELEIN , AVEFA, IPOHE, CIRAR, AMARE, CHEAL, CYPES or SETFA.
[0064] In certain embodiments of the compositions and methods described herein, the compound of Formula (I) or salt or ester thereof is used in combination with glyphosate or a salt thereof. In some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to glyphosate or a salt thereof is within the range of about 1: 1120 to about 3: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to glyphosate or a salt thereof is within the range of 1:95 to about 1: 3. In some embodiments, the weight ratio of the Formula I compound or salt or ester thereof and glyphosate or a salt thereof is about 1: 3 to about 1: 220. In some embodiments, the weight ratio of the Formula I compound or salt or ester thereof and glyphosate or a salt thereof is about 1: 6 to about 1: 112. Regarding the methods, in certain modalities, the methods comprise contact of undesirable vegetation or its location or application to the soil or water to prevent the emergence or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate between about 107 grams of acid equivalent per hectare (GAE / ha) and about 2540 GAE / ha, based on the total amount of active ingredients in the composition. In certain modalities, the composition is applied at an application rate of about 109 grams of acid equivalent per hectare (GAE / ha) and about 450 GAE / ha, based on the total amount of active ingredients in the composition. In some modalities, the methods comprise contact of undesirable vegetation or its location or application to the soil or water to avoid the appearance or growth of vegetation of a compound of Formula (I) or salt or ester thereof and glypho- sato or a salt thereof, for example, sequentially or simultaneously. In some embodiments, the glyphosate or its salt or ester is applied at a rate of about 30 GAE / ha and about 2240 GAE / ha and the compound of Formula (I), salt or ester thereof is applied in a level from about 2 GAE / ha to about 300 GAE / ha. In some embodiments, the rate of application of a compound of Formula I or its salt or ester is about 2 GAE / ha to about 70 GAE / ha and the rate of application of glyphosate or its salt is about from 100 to about 1000 gai / ha. In some embodiments, the rate of application of a Formula I compound or salt or ester thereof is about 1.1 GAE / ha to about 35 GAE / ha and the rate of application of glyphosate or its salt is from about 105 to about 840 gai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof, in combination with glyphosate or a salt thereof, are used to control ECHCG, ECHCO, LEFCH, CYPDI, SCPMA, IPOHE, DIGSA, SORHA, AVEFA or POLCO.
[0065] In certain embodiments, the glyphosate dimethylammonium salt (DMA) is used. In some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to glyphosate dimethylammonium is within the range of about 1: 1120 to about 3: 1. In certain embodiments, the weight ratio of the Formula (I) compound or salt or ester thereof to glyphosate dimethylammonium is within the range of 1: 420 to about 1: 4. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to glyphosate dimethylammonium is 1:10 to about 1: 220. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to glyphosate dimethylammonium is from about 1:22 to about 1: 112. In some embodiments, the composition comprises the compound of Formula I and glyphosate dimethylammonium. In some embodiments, the composition comprises the compound of Formula I and glyphosate dimethylammonium, wherein the weight ratio of the compound of Formula I to glyphosate dimethylammonium is from about 1:22 to about 1: 112. In some embodiments, the composition comprises the n-butyl ester of the compound of Formula I and glyphosate dimethylammonium. In some embodiments, the composition comprises the n-butyl ester of the Formula I compound and glyphosate dimethylammonium, wherein the weight ratio of the Formula I compound to glyphosate dimethylammonium is about 1:26. In some embodiments, the composition comprises the benzyl ester of the compound of Formula I and glyphosate dimethylammonium. In some embodiments, the composition comprises the benzyl ester of the Formula I compound and glyphosate dimethylammonium, wherein the weight ratio of the Formula I compound to glyphosate dimethylammonium is about 1:26. In relation to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or its location or application to the soil or water to prevent the appearance or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of about 75 grams of acid equivalent per hectare (GAE / ha) and about 2,540 GAE / ha, based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate comprised between about 107 grams of acid equivalent per hectare (GAE / ha) and about 872 GAE / ha, based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or its location or application to soil or water to prevent the appearance or growth of vegetation of a compound of Formula (I) or salt or ester thereof and glyphosate dimethylammonium, for example , sequentially or simultaneously. In certain embodiments, the methods use the compound of Formula I and glyphosate dimethylammonium, where the compound of Formula I is applied at an application rate of about 3 to about 32 GAE / ha and glyphosate dimethylammonium is applied in a rate of about 105 to about 840 g ai / ha. In certain embodiments, the methods use the n-butyl ester or benzyl ester of the Formula I compound and glyphosate dimethylammonium, where the n-butyl ester or benzyl ester of the Formula I compound is applied at a rate of about 32 gae application / ha and glyphosate dimethylammonium is applied at a rate of about 840 g ai / ha. In some embodiments, glyphosate is applied at a rate of about 105 g ai / ha and about 2240 g ai / ha and the compound of Formula (I), its salt or ester is applied at a rate of about 2 GAE / ha to about 300 GAE / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with glyphosate dimethylammonium are used to control CYPES, DIGSA, ECHCG, LEFCH, SETFA, SORHA and VIOTR.
[0066] In certain embodiments, the glyphosate isopropylammonium salt (IPA) is used. In some embodiments, the weight ratio of the Formula (I) compound or glyphosate isopro-pylammonium salt or ester is in the range of about 1: 1120 to about 3: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to glyphosate isopropylammonium is within the range of 1: 509 to about 1: 3. In some embodiments, the weight ratio of the Formula I compound or salt or ester thereof to glyphosate isopropylammonium is about 1: 3 to about 1: 200. In some embodiments, the weight ratio of the Formula I compound or glyphosate isopropylammonium salt or ester is about 1: 3 to about 1: 509 In some embodiments, the composition comprises the Formula I compound and isopropylammonium glyphosate. In certain embodiments, the weight ratio of the glyphosate isopropylammonium Formula I compound is from about 1: 6 to about 1:96. In some embodiments, the composition comprises the n-butyl ester of the compound of Formula I and glyphosate isopropylammonium. In some embodiments, the composition comprises the n-butyl ester of the Formula I compound and glyphosate isopropylammonium, wherein the weight ratio of the Formula I compound to glyphosate isopropylammonium is about 1:26. In some embodiments, the composition comprises the benzyl ester of the compound of Formula I and glyphosate isopropylammonium. In certain embodiments, the weight ratio of the benzyl ester of the Formula I compound to glyphosate isopropylammonium is about 1: 6 to about 1: 509. In relation to the methods, in certain modalities, the methods comprise contact of undesirable vegetation or its location or application to the soil or water to prevent the appearance or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate comprised between about 107 grams of acid equivalent per hectare (GAE / ha) and about 2.540 GAE / ha, based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 109 grams of acid equivalent per hectare (GAE / ha) and about 564 GAE / ha, based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of undesirable vegetation or its location or application to soil or water to prevent the appearance or growth of vegetation of a compound of Formula (I) or a salt or ester thereof and glyphosate isopropylammon, for example example, sequentially or simultaneously. In some embodiments, glyphosate isopropylammonium is applied at a rate of about 105 GAE / ha and about 2240 GAE / ha and the compound of Formula (I), salt or ester thereof is applied at a level of about 2 GAE / ha to about 300 GAE / ha. In certain embodiments, glyphosate isopropylammonium is applied at a rate of about 50 GAE / ha to about 800 GAE / ha and the compound of Formula (I), salt or ester thereof is applied at a level of about 2 GAE / ha at about 70 GAE / ha. In certain embodiments, glyphosate isopropylammonium is applied at a rate of about 105 GAE / ha to about 560 GAE / ha and the compound of Formula (I), salt or ester thereof is applied at a rate of about from 4 GAE / ha to about 35 GAE / ha. In certain modalities, the methods use the compound of Formula I and isopropylammonium glyphosate, where the compound of Formula I is applied at an application rate of about 1 to about 35 GAE / ha and the glyphosate isopropylammonium applied at a rate of about 100 to about 560 g ai / ha. In certain embodiments, the methods use the benzyl ester of the compound of Formula I and isopropylammonium of glyphosate, where the benzyl ester of the compound of Formula I is applied at a rate of about 4 g of application at about 35 ia / ha and the glyphosphate isopropylammonium is applied at a rate of about 100 to about 450 g ai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in association with glyphosate isopropylammonium are used to control ECHCG, ECHCO, LEFCH, CYPDI, SCPMA, IPOHE, AVEFA or POLCO.
[0067] In certain embodiments of the compositions and methods described here, the compound of Formula (I) or salt or ester thereof is used in combination with glyphosate trimesium (also known as sulfosate). In some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to glyphosate trimesium is within the range of about 1: 852 to about 10: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester of the glyphosate trimesium is within the range of 1: 136 to about 1: 1. In some embodiments, the composition is applied at an application rate comprised between about 30 grams of acid equivalent per hectare (GAE / ha) and about 2000 GAE / ha, based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 35 grams of acid equivalent per hectare (GAE / ha) and about 650 GAE / ha based on the total amount of active ingredients in the composition. In some embodiments, glyphosate trimesium is applied at a rate of about 30 GAE / ha and about 1705 GAE / ha and the compound of Formula (I), salt or ester thereof is applied at a level of about from 2 GAE / ha to about 300 GAE / ha.
[0068] The mixtures described here can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation. When used in conjunction with other herbicides, the composition can be formulated with the other herbicide or herbicides, mixed in the tank with another herbicide or herbicides or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be used in conjunction with the compositions and methods described here include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 2,4-D choline salt, 2,4-D, 2,4-DB esters and amines; 3,4-DA; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametrine, amibuzine, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-anilone, amylone, amitrone , asulam, atratone, atrazine, azafenidin, azimsulfurone, aziprotrin, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, ben-sulide, benthiocarb, benzenthazine, benzene, benzene - pram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazurone, bialophos, bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil, bromobonil, bromobutide, bromophenoxin, butromoxyl, butromethyl, bromoxyn, - la, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrola, calcium chlorate, calcium cyanamide, cambendichlor, carburetam, carbetamide, carboxazole, chlorprocar b, carfentrazone-ethyl, CDEA, CEPC, clomethoxyfen, chlorambene, chloranocril, chlorazifop, chlorazine, chlorobromurone, chlorbufam, chloreturone, chlorfenac, chlorphenphenone, chlorflurazole, chlorflurenol, chloridazone, chlorimurone, chloride, chloride, chloride chloroxynil, chlorpropham, chlorsulfurone, chlortal, chlortamide, cinidon-ethyl, cinmetilina, cinosulfuroan, cisanilide, clethodim, cliodinato, clodinafop-propargila, clofop, clozone, clomeprop, cloprop, cloproxydans, cloproxydim, cloprma copper sulphate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatrine, cyanazine, cyclate, cyclopyrimorate, cyclosulfa- murona, cycloxydim, cycluron, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, cypromid, daimuron, daimuron, dalapon, dalapon, dalapon, dalapon desme- dipham, desmetrina, di-alate, dicamba, dichlobenil, dichloralurea, di-chlormate, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, di-ethamquat, diethyl, diphenopentene, diphenoxurone, difenzoquurone at, diflufenican, diflufenzopyr, dimefurone, dimepiperate, dimethachlor, dimethatrine, dimethenamid, dimethenamid-P, dimexane, dimidazon, dintramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropine, dipropine dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, etalfluroline, etbenzamide, etametsulfurone, ethidimuron, etiolate, ethobenza-mid, etobenzamid, etofumes, etofumesate, ethoxy etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop, phenoxyprop-P-ethyl, phenoxaprop-P-ethyl + isoxadifen-ethyl, phenoxasulfone, phenteracol, fenthiaprop, fentrazamide, fenurone, ferrous sulfate, flamprop, flamprop, flamprop , florasulam, fluazifop, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfurone, flucloraline, flufena-cet, flufenican, flufenpyr-ethyl, flumetsulam, flumezine, flumiclorac-pentila, flumioxazine, flumipropyl, flumipropyl, flumipropyl , fluoroidine, fluoroitrophen, fluothiurone, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, fluorochloridone, fluroxypyr, flu-roxypyr-meptila, flurtamone, fluthiacet, fomesafene, foramsulfuroxyl, furofla, furofa, , halosulfuron-methyl, haloxidine, haloxyfop-methyl, haloxyfop- P-methyl, hexachloroacetone, hexaflurate, hexazinone, imazametha-benz, imazamox, imazapic, imazapyr, imazaquin, imazosulfurone, imaosulfurone, imaobrazano, , iodosulfurone-ethyl-sodium, iofensulfurone, ioxynil, ipazin, ipfencarbazoine, iprymidam, isocarbamid, isocyl, isomethiozine, isonorurone, isopolinate, isopropalin, isoproturone, isourone, isoxabyr, isoxacyrol, isoxaclate, isoxacl , lactophen, lenacil, linurone, MAA, MAMA, esters and amines of MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazin, mesosul furona, mesotrione, metam, metamifop, metamitron, methazachlor, metazosulfurone, metflurazone, metabenzthiazurone, metallopralin, metazola, methiobencarb, methiozoline, methiuron, methomethon, methoprotrin, methylmethylamine, rhodium-methylene bromide, isothiocyanate, rhodium metobenzuron, metobromuron, metolachlor, metosulam, methoxy-ron, metribuzin, metsulfurone, metsulfurone-methyl, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, mor-famquat, MSMA, naproanilide, naptamide, naptamide, , nipyraclofen, nitralin, nitrophen, nitrofluorphene, norflurazone, norurone, OCH, orbencarb, o / to-dichlorobenzene, ortosulfamurone, orizaline, oxadiargyl, oxadiazone, oxapirazone, oxasulfurone, oxazufurene, paraoxyfluifome, , pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenyl mercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron-methyl, prociazine, prodiamine, profluazole, profluralin, propoxy-dim, progoxazine, progoxazine -calcium, prometon, promethin, prone- mide, propachlor, propanyl, propaquizafop, propazine, propham, propi- sochlor, propoxycarbazone, propyrisulfurone, propizamide, prosulfaline, prosulfocarb, prosulfurone, proxan, prynachlor, pydanon, pyraclon, pyraclon, pyraclon , pyrazogyl, pyrazolinate, pyrazosulfurone-ethyl, pyrazoxifene, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinofac, quinqual, quinqual, quinqual -P-ethyl, rhodetanil, rimsulfurone, saflufenacil, S- metolachlor, sebutilazine, secbumeton, sethoxydim, siduron, simazine, simeton, symmetry, SMA, SYN-523, arsenite sodium, sodium azide, sodium chlorate, sulcotrione, sulfalate, sulfentrazone, sulfometurone, sulfosulfurone, sulfuric acid, sulglicapine, swep, TCA, tebutam, tebutiurone, tefuriltrione, tembotrione, tepraloxydim, terbacil, terbacil, terbacil, terbacil, terbacil terbumetone, terbuthylin, terbutrin, tetraflurone, thenylchlor, thiazaflurone, thiazopyr, thidiazimin, tidiazurone, tiencarbazone-methyl, tifensulfuron, tifensulfurone-methyl, thiobencaria, trifluoro, trilammon, triloxin, trilimone, trilimone tribenurone-methyl, tricamba, choline salt of triclopyr, esters and salts of triclopyr, tridifan, trietazine, trifloxysulfurone, trifluralin, triflusulfurone, trifop, trifopsim, trihydroxytriazine, trimeturone, trpropin-tr, tritinite, trpropin-dan, tritinyl, tracin, trpropin esters, optically active isomers and mixtures thereof.
[0069] The compositions and methods described here can also be used in conjunction with glyphosate, 5-enolpyruvylchiquimate-3-phosphate synthase inhibitors (5-EnolPyruvylShikimate-3-Phosphate - EPSP, glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxy phenoxy propionates, cyclohexanediones, phenylpiperazolines, acetyl CoA carboxylase inhibitors (Acetyl ÇoA Carboxylase - ACCase), imidazolinines, sulfonylsulfines , sulfonylaminocarbonyltriazolinones, acetolactate synthase inhibitors (AcetoLactate Synthase - ALS) or acetohydroxy acid synthase (AcetoHydroxy Acid Synthase - AHAS), 4-hydroxyphenyl-pyruvate dioxigenase inhibitors (4-HydroxyPhene-Di-Pyryl-Pyrene-Pyryl-Pyryl , phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, protoporphyrinogen oxidase inhibitors (ProtoPorphyrinogen O xidase - PPO), cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, lipid and fatty acid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines and bromoxynil in glyphosate-tolerant crops, tolerant to a 5-enolpyruvylchiquimate-3-phosphate synthase inhibitor (5-EnolPyruvylShikimate-3-Phosphate - EPSP), tolerant to glufosinate, tolerant to a glutamine synthase inhibitor, tolerant to dicamba, tolerant to phenoxy auxin, tolerant to pyridyloxy auxin, tolerant to synthetic auxin, tolerant to an inhibitor of auxin transport, tolerant to aryloxy phenoxy propionates, tolerant to cyclohexanedione, tolerant to phenylpyrazoline, tolerant to an acetyl carboxylase inhibitor CoA (Acetyl ÇoA Carboxylase - ACCase), tolerant to imidazolinone, tolerant to sulfonylurea, tolerant to pyrimidinylthiobenzoate, tolerant to triazolop irimidine, tolerant to sulfonylaminocarbonyltriazolinone, tolerant to an acetolactate synthase inhibitor (AcetoLactate Synthase - ALS) or acetohydroxy acid synthase (AcetoHydroxy Acid Synthase - AHAS), tolerant to a 4-hydroxyphenyl dioxigenase inhibitor (4-hydroxyphenyl) HydroxyPhenyl- Pyruvate-Dioxygenase - HPPD), tolerant to a phytoene desaturase inhibitor, tolerant to a carotenoid biosynthesis inhibitor, tolerant to a protoporphyrinogen oxidase inhibitor (ProtoPorphyrinogen Oxidase - PPO), tolerant to an inhibitor of biosynthesis cellulose, tolerant to a mitosis inhibitor, tolerant to a microtubule inhibitor, tolerant to a very long chain fatty acid inhibitor, tolerant to a lipid and fatty acid biosynthesis inhibitor, tolerant to a photosystem I inhibitor, tolerant to a photosystem II inhibitor, tolerant to triazine or tolerant to bromoxynil and crops that have multiple or stacked traits that confer tol erance to various chemicals and / or several modes of action via a single or multiple resistance mechanisms. In some embodiments, the compound of Formula (I) or salt or ester thereof and the complementary herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop to be treated and that complement the spectrum of weeds controlled by these compounds at the application rate used. In some embodiments, the compositions described here and other complementary herbicides are applied at the same time either as a combined formulation or as a tank mix.
[0070] In some embodiments, the compositions described here are used in combination with one or more herbicide protectors, such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolid, cloquintocet (mexila), ciometrinila, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenclorazola-ethyl, fenclorim, flurazola, flux-phenim, furilazola, proteins harpina, isoxadifeno-ethyl, jiecaowan, jieca-oxy, mefenpyr-dietila, mefenato, oxytranic anhydride (NA); of N-phenylsulfonyl benzoic acid, to increase its selectivity. In some modalities, protectors are used in rice, cereals, maize or green maize fields. In some embodiments, the protector is cloquintocet or an ester or salt thereof. In certain embodiments, cloquintocet is used to antagonize the harmful effects of the compositions on rice and cereals. In some embodiments, the protective agent is cloquintocet (mexila).
[0071] In some embodiments, the compositions described here are used in combination with one or more plant growth regulators, such as 2,3,5-triiodiodobenzoic acid, IAA, IBA, naphthalene acetamide, α-naphthalene acids acetic, benzyladenine, 4-hydroxy phenethyl alcohol, kinetin, zeatin, endothal, ethephon, pentachlorophenol, thidiazuron, tributes, aviglycine, ethephon, maleic hydrazide, gibberellins, gibberellic acid, abscisic acid, glyphidine, phosphidolin, , isopyrimol, jasmonic acid, maleic hydrazide, mepiquat, 2,3, 5-triiodiodobenzoic acid, morphactins, dichlorflurenol, flurprimidol, mefluidide, paclobutrazol, tetcyclacis, uniconazole, brassinolide, brassinolide-ethyl, cyclohexane, ethyl-cyclohexyl, ethylene oxide, cyclohexane proexadione, triapentenol and trinexapac.
[0072] In some modalities, plant growth regulators are used in one or more crops or environments, such as rice, cereals, corn, leafy crops, rapeseed / canola, grass, pineapple, sugar cane, sunflower, pasture, meadows, arable land, idle land, trees and orchards, plantation crops, vegetables and non-agricultural (ornamental) environments. In some embodiments, the plant growth regulator is mixed with the compound of Formula (I) or mixed with the compound of Formula (I) and glyphosate or glufosinate to cause a preferential beneficial effect on plants.
[0073] In some embodiments, the compositions provided here further comprise at least one agriculturally acceptable adjuvant or vehicle. Suitable adjuvants or vehicles should not be phytotoxic to valuable crops, particularly at the concentrations used in applying weed control compositions in the presence of crops and should not react chemically with the herbicide components or other ingredients in the composition. Such mixtures can be designed for application directly to weeds or their location or they can be concentrated or formulations that are normally diluted with additional vehicles and adjuvants before application. They can be solids such as, for example, powders, granules, water-dispersible granules or wetting powders or liquids such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be supplied as a premix or mixed in a tank.
[0074] Suitable adjuvants and agricultural vehicles include, but are not limited to, concentrated Crop Oil; nonylphenol ethoxylate; benzylcocoalkylimethyl quaternary ammonium salt; mixture of petroleum hydrocarbons, alkyl esters, organic acid and anionic surfactant; C9-C11 alkyl polyglycoside; phosphate alcohol ethoxylate; (C12-C16) ethoxylate natural primary alcohol; di-sec-butylphenol; EO-PO block copolymer; methyl polysiloxane buffer; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); dioleate-99 of PEG (400).
[0075] Liquid vehicles that can be used include water and organic solvents. Organic solvents include, but are not limited to, oil fractions or hydrocarbons, such as mineral oil, aromatic solvents, paraffinic oils and the like; vegetable oils, such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, flaxseed oil, palm oil, oil peanut, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric or other lower polyalcohols (containing 4-6 hydroxy), such as hexyl 2-ethyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono-, di- and poly-carboxylic acids; and the like. Specific organic solvents include, but are not limited to, toluene, xylene, petroleum naphtha, Crop Oil, acetone, methyl ethyl ketone, cyclohexanone, trichlorethylene, perchlorethylene, ethyl acetate, amyl acetate, butyl acetate, monomethyl ether propylene glycol and monomethyl ether, diethylene glycol, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerin, N-methyl-2-pyrrolidinone, N, N-dimethylalkylamides, sulfoxide dimethyl, liquid fertilizers and the like. In certain modalities, water is the vehicle for the dilution of concentrates.
[0076] Suitable solid vehicles include, but are not limited to, talc, pyrophyllite clay, silica, atapulgite clay, kaolin, diatomaceous earth, chalk, lime, calcium carbonate, bentonite clay, Fuller earth, cotton husks, flour wheat, soy flour, pumice, wood flour, nutshell flour, lignin, cellulose and the like.
[0077] In some embodiments, the compositions described here further comprise one or more of surfactants. In some embodiments, such surfactants are used in solid and liquid compositions and, in certain embodiments, are intended to be diluted with a vehicle before application. Surfactants can be anionic, cationic or non-ionic and can be used as emulsifying agents, wetting agents, suspending agents or for other purposes. Surfactants that can also be used in the present formulations are described, inter alia, in "McCutcheon Detergents and Emulsifiers Annual", MC Publis-hing Corp, Ridgewood, New Jersey, 1998 and in "Encyclopedia of Sur-factants", vol. I-III, Chemical Publishing Co., New York, 1980-1981. Surfactants include, but are not limited to, alkyl sulphate salts, such as diethanolammonium lauryl sulfate; alkyl aryl sulfonate salts, such as calcium dodecyl benzene sulfonate; alkyl phenol-alkylene oxide addition products, such as nonylphenol-Cw ethoxylate; products of the addition of alcohol - alkylene oxide, such as C1-6 tridecyl alcohol ethoxylate; soaps, such as sodium stearate; alkyl naphthalene sulfonate salts, such as sodium dibutyl naphthalene sulfonate; dialkyl esters of sulfo-succinate salts, such as sodium di- (2-ethylhexyl) sulfo-succinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as trimethyl ammonium lauryl chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; mono and dialkyl phosphate esters; vegetable or seed oils, such as soybean oil, rapeseed / canola oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils and, in certain embodiments, methyl esters.
[0078] In some embodiments, these materials, such as vegetable oils or seed oils and their esters, can be used alternatively as an agricultural adjuvant, such as a liquid excipient or as a surfactant.
[0079] Other exemplary additives for use in the compositions provided here include, but are not limited to, compatibility agents, anti-foaming agents, capture agents, neutralizing agents and buffers, corrosion inhibitors, colorants, odorants, dispersing agents , penetration aids, bonding agents, spreading agents, thickeners, freezing point depressants, antimicrobial agents and the like. The compositions can also contain other compatible components, for example, other herbicides, plant growth regulators, fungicides, insecticides and the like and can be formulated with liquid or solid fertilizers, particulate fertilizers, such as nitrate ammonium, urea and the like.
[0080] In some embodiments, the concentration of the active ingredients in the compositions described here is about 0.0005 to 98 weight percent. In some embodiments, the concentration is about 0.0006-90 weight percent. In compositions designed to be used as concentrates, the active ingredients, in certain embodiments, are present in a concentration of about 0.1 to 98 percent by weight and, in certain embodiments, are about 0.5 to 90 percent in Weight. These compositions are, in certain embodiments, diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the weed site contain, in certain embodiments, about 0.0006 to 15.0 weight percent of the active ingredient and, in certain embodiments, contain about 0.01 to 10, 0 weight percent.
[0081] The present compositions can be applied to weeds or their location using conventional soil or aerial atomizers, sprayers and granule applicators, by adding to irrigation water and by other conventional means known to those skilled in the art .
[0082] The modalities described and examples below are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses or combinations in relation to the compositions described here will be evident to those skilled in the art without departing from the spirit and scope of the claimed subject. Examples
[0083] Results of Examples I, II, III, IV and V are results of tests in the greenhouse. Example I. Evaluation of Herbicidal Mixtures for Post-emergence Foliar Application for Weed Control in Rice Directly Cultivated
[0084] Seeds or grains of the desired test plant species were planted in a soil matrix prepared by mixing a sandy or clay-covered soil (eg 28.6 percent sludge, 18.8 percent clay and 52.6 percent sand, with a pH of about 5.8 and an organic matter content of about 1.8 percent) and limestone in a ratio of 80 to 20. The soil matrix was contained in pots of plastic with a volume of 1 liter and a surface area of 83.6 square centimeters (cm2). When necessary to ensure good germination and healthy plants, a fungicide treatment and / or other chemical or physical treatment was applied. The plants were grown for 8-22 days in a greenhouse with a photoperiod of approximately 14 h, which was maintained at about 29 C during the day and 26 C C during the evening. Nutrients (Pe-ters Excel® 15-5-15 5-Ca 2-Mg & Iron Chelate) were applied to the irrigation solution as needed and water was added on a regular basis. Supplementary lighting was provided with 1000 Watt metal halide lamps, if necessary. The plants were used for testing when they reached the stage of first to fourth true leaves.
[0085] The treatments consisted of 4- amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) -pyridine-2-carboxylic acid or esters (Compound A ), each formulated as a SC (Suspen-sion Concentrate - concentrated in suspension) and several herbicidal components individually and in combination. Compound A forms were applied based on acid equivalent.
[0086] Forms of compound A (compound of Formula I) tested include:

[0087] Other herbicidal components were applied based on an acid equivalent or active ingredient and included the synthase inhibiting herbicide 5-enolpyruvylchiquimate-3-phosphate (5- EnolPyruvylShikimate-3-Phosphate Synthase - EPSPS), isopropylamine salt glyphosate, formulated as Glyphomax®, Durango® or Rodeo®, glyphosate dimethylamine salt formulated as Durango DMA® and the glutamine synthase inhibiting herbicide (Glutamine Synthase - GS), ammonium glufosinate, formulated as Ignite® 280.
[0088] Treatment requirements have been calculated based on the rates being tested, the concentration of the active ingredient or acid equivalent in the formulation and an application volume of 12 ml_ at a rate of 187 L / ha.
[0089] For treatments comprised of formulated compounds, measured amounts of compounds were individually placed in 25 ml_ glass bottles and diluted in a 1.25% (v / v) volume of concentrated Crop Oil Agri-Dex® to obtain solutions of stock 12X. If a test compound did not readily dissolve, the mixture was heated and / or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (eg 1 ml) and diluted to the appropriate final concentrations with the addition of 10 ml of an aqueous mixture of Crop Oil 1.25% (v / v) concentrate, so that the final spray solutions contain 1.25 ± 0.05% (v / v) of concentrated Crop Oil.
[0090] For treatments comprised of technical compounds, heavy amounts can be placed individually in 25 ml glass bottles and dissolved in a 97: 3 v / v volume of acetone / DMSO to obtain 12X stock solutions. If a test compound does not readily dissolve, the mixture can be heated and / or added. Application solutions can be prepared by adding an appropriate amount of each stock solution (for example, 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of Crop Oil concentrated to 1 , 5% (v / v), so that the final spray solutions contain 1.25% (v / v) of concentrated Crop Oil. When technical materials are used, concentrated stock solutions can be added to the spray solutions, so that the final concentrations of acetone and DMSO in the application solutions are 16.2% and 0.5%, respectively.
[0091] For treatments comprised of formulated and technical compounds, heavy amounts of technical materials can be placed individually in 25 ml_ glass vials and dissolved in a 97: 3 v / v acetone / DMSO volume to obtain 12X stock solutions and measured amounts of formulated compounds can be placed individually in 25 ml glass vials and diluted in a volume of 1.5% (v / v) concentrated Crop Oil or water to obtain 12X stock solutions. If a test compound does not readily dissolve, the mixture can be heated and / or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (for example, 1 ml) and diluted to the appropriate final concentrations with the addition of an appropriate amount of a 1.5% aqueous mixture (v / v) concentrated Crop Oil, so that the final spray solutions contain 1.25% (v / v) concentrated Crop Oil. As needed, additional water and / or 97: 3 v / v acetone / DMSO can be added to the individual application solutions, so that the final concentrations of acetone and DMSO of the application solutions being compared are 8.1 % and 0.25%, respectively.
[0092] All stock solutions and application solutions were visually checked for compound compatibility before application. Spray solutions were applied to the plant material with an Overhead Mandel Track sprayer equipped with 8002E nozzles calibrated to distribute 187 L / ha over an application area of 0.503 m2 at a spray height of 46 to 50 cm (18 to 20 inches) above the average height of the canopy of the plants. Control plants were sprayed in the same way with solvent (blank).
[0093] The treated plants and control plants were placed in a greenhouse as described above and watered by means of sub-irrigation to prevent washing of the test compounds. After approximately 3 weeks, the condition of the test plants, when compared to untreated plants, was determined visually and classified on a scale of 0 to 100 percent, where 0 corresponds to the absence of damage or inhibition of growth and 100 corresponds to to complete death.
[0094] Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, SR 1967. Calculation of The Synergistic and Antagonistic Response of Herbicide Combinations-Weeds 15: 20-22).
[0095] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: Expected = A + B - (A x B / 100)
[0096] A = observed effectiveness of active ingredient A at the same concentration as used in the mixture
[0097] B = observed effectiveness of active ingredient B at the same concentration as used in the mixture
[0098] The tested compounds, application rates employed, plant species tested and results are provided in Tables 1-11. Table 1. Synergistic Activity of Herbicidal Compositions of Compound A - Glyphomax® Acid and Isopropylamine Salt (Glyphomax®) for Foliar Application in the Control of Weeds Common to Rice Culture Systems

Table 2. Synergistic Activity of Herbicidal Compositions of Compound A - Glyphosate Isopropylamine (Rodeo®) Acid and Foliar Application in the Control of Weeds Common to Rice Culture Systems

Table 3. Synergistic Activity of Herbicidal Compositions of Compound A - Acid and Glyphosate Isopropylamine Salt (Durango®) for Foliar Application in the Control of Weeds Common to Rice Culture Systems
Table 4. Synergistic Activity of Herbicidal Compositions of Compound A - n-Butyl Ester and Glyphosate Isopropylamine Salt (Durango®) for Foliar Application in the Control of Weeds Common to Rice Culture Systems
Table 5. Synergistic Activity of Herbicidal Compositions of Compound A - Benzyl Ester and Glyphomax® Isopropylamine Salt (Glyphomax®) for Foliar Application in the Control of Weeds Common to Rice Culture Systems

Table 6. Synergistic Activity of Herbicidal Compositions of Compound A - Benzyl Ester and Glyphosate Isopropylamine Salt (Rodeo®) for Foliar Application in the Control of Weeds Common to Rice Culture Systems

Table 7. Synergistic Activity of Herbicidal Compositions of Compound A - Benzyl Ester and Glyphosate Isopropylamine Salt (Durango®) for Foliar Application in the Control of Weeds Common to Rice Culture Systems
Table 8. Synergistic Activity of Herbicidal Compositions of Compound A - Benzyl Ester and Glyphosate Dimethylamine Salt (Durango DMA®) for Foliar Application in the Control of Weeds Common to Rice Culture Systems

Table 9. Synergistic Activity of Herbicidal Compositions of Compound A - Glufosinate Acid and Salt Foliar Application in the Control of Weeds Common to Rice Culture Systems

Table 10. Synergistic Activity of Herbicidal Compositions of Compound A - n-Butyl Ester and Glufosinate Ammonium Salt for Foliar Application in the Control of Weeds Common to Rice Culture Systems
Table 11. Synergistic Activity of Herbicidal Compositions of Compound A - Benzyl Ester and Glufosinate Ammonium Salt for Foliar Application in the Control of Weeds Common to Rice Culture Systems


Example II. Evaluation of Herbicidal Mixtures Applied in Water to Control Weeds in Transplanted Rice
[0099] Weed seeds or grains of the desired test plant species were planted in flooded soil (mud) prepared by mixing a non-sterilized ground mineral soil (50.5 percent sludge, 25.5 percent clay and 24 percent sand, with a pH of about 7.6 and an organic matter content of about 2.9 percent) and water in a volumetric ratio of 1: 1. The prepared sludge was distributed in 365 mL aliquots in 16-ounce (oz) unperforated plastic pots with a surface area of 86.59 square centimeters (cm2), leaving a top space of 3 centimeters (cm) in each vase. The mud was left to dry overnight before planting or transplanting. Rice seeds were planted in a Sun Gro MetroMix® 306 planting mix which typically has a pH of 6.0 to 6.8 and an organic matter content of around 30 percent, in plastic trays. Seedlings in the second or third leaf growth stage were transferred to 840 ml_ of mud contained in 32 oz plastic pots. not drilled with a surface area of 86.59 cm2 four days before herbicide application. The rice field was created by filling the upper space of the pots with 2.5 to 3 cm of water. When necessary to ensure good germination and healthy plants, a fungicide treatment and / or other chemical or physical treatment was applied. The plants were grown for 4-22 days in a greenhouse with a photoperiod of approximately 14 h, which was maintained at about 29 C during the day and 26 C C during the night. Nutrients were postponed, such as Osmocote® (19: 6: 12, N: P: K + micronutrients) to 2 g per 16 oz. and 4 g per 32 oz. pot. Water was added on a regular basis to keep flooding the paddy and supplemental lighting was provided with 1000 Watt metal halide lamps, if necessary. The plants were used for testing when they reached the stage of first to fourth true leaves.
[00100] The treatments consisted of 4- amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) -pyridine-2-carboxylic acid or esters (compound A ), each formulated as a SC (Suspension Concentrate - concentrate in suspension) and several herbicidal components individually and in combination. Compound A forms were applied based on acid equivalent.
[00101] Forms of compound A (compound of Formula I) tested include:

[00102] Other herbicidal components were applied based on an acid equivalent or active ingredient and included the synthase inhibiting herbicide 5-enolpyruvylchiquimate-3-phosphate (5- EnolPyruvylShikimate-3-Phosphate Synthase - EPSPS), isopropylamine salt glyphosate, formulated as Rodeo®.
[00103] Treatment requirements for each compound or herbicidal component were calculated based on the rates being tested, the concentration of the active ingredient or acid equivalent in the formulation, an application volume of 2 ml_ per component per pot and an area application rate of 86.59 cm2 per pot.
[00104] For formulated compounds, a measured amount was placed in an individual glass bottle of 100 to 200 ml_ and was dissolved in a volume of 1.25% (v / v) of concentrated Agri-Dex® Crop Oil to obtain solutions for application. If a test compound did not readily dissolve, the mixture was heated and / or sonicated.
[00105] For technical grade compounds, a heavy amount can be placed in an individual glass bottle of 100 to 200 ml_ and dissolved in a volume of acetone to obtain concentrated stock solutions. If the test compound does not readily dissolve, the mixture can be heated and / or sonicated. The concentrated stock solutions obtained can be diluted with an equivalent volume of an aqueous mixture containing 2.5% (v / v) concentrated Crop Oil, so that the final solutions for application contain 1.25% (v / v) of concentrated Crop Oil.
[00106] The applications were made by injection with a pipette of appropriate quantities of the solutions for application, individually and sequentially, in the aqueous layer of the rice field. Control plants were treated in the same way with the solvent in a blank assay. The applications were made so that all the treated plant material received the same concentrations of acetone and concentrated Crop Oil.
[00107] The treated plants and control plants were placed in a greenhouse as described above and water was added as needed to keep a paddy field flooded. After approximately 3 weeks, the condition of the test plants, when compared to untreated plants, was determined visually and rated on a scale of 0 to 100 percent, where 0 corresponds to the absence of damage or inhibition of growth and 100 corresponds to death complete.
[00108] Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, SR 1967. Calculation of The Synergistic and Antagonistic Response of Herbicide Combinations. L / l / eeds 15: 20-22.).
[00109] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: Expected = A + B - (A x B / 100)
[00110] A = observed effectiveness of active ingredient A at the same concentration as used in the mixture
[00111] B = observed effectiveness of active ingredient B at the same concentration as used in the mixture
[00112] Some of the tested compounds, application rates employed, plant species tested and results are provided in Table 12. Table 12. Synergistic Activity of Herbicidal Compositions of Compound A - Glyphosate Isopropylamine Acid and Water Application in Control of Weeds Common to Rice Culture Systems
SCPMA Schoenoplectus maritimus (L.) Lye or Bolboschoenus maritimus (L.) Palia aquatic reed gae / ha = acid equivalent in grams per hectare gai / ha = active ingredient in grams per hectare Obs = observed value Esp = expected value as calculated by the equation Colby DAA = days after application (Days After Application) Example III. Evaluation of Post-emergence Foliar Herbicidal Mixtures to Control Weeds in Crops, such as Corn and Soy
[00113] Seeds or grains of the desired test plant species were planted in a soil matrix prepared by mixing a sandy or clay-covered soil (eg 43 percent sludge, 19 percent clay and 38 percent percent sand, with a pH of about 8.1 and an organic matter content of about 1.5 percent) and limestone in a ratio of 80 to 20. The soil matrix was contained in plastic pots with an area surface area of 84.6 square centimeters (cm2) and a volume of 560 cubic centimeters (cm3). When necessary to ensure good germination and healthy plants, a fungicide treatment and / or other chemical or physical treatment was applied. The plants were grown for 7-31 days in a greenhouse with a photoperiod of approximately 15 h, which was maintained at about 23-29 'C during the day and 22-28' C during the night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg) and water were added on a regular basis and supplementary lighting was provided with 1000 Watt metal halide lamps as needed. The plants were used for testing when they reached the stage of first, second or third true leaves.
[00114] Treatment requirements were calculated based on the rates being tested, the concentration of active ingredient or acid equivalent in the formulation and an application volume of 12 mL at a rate of 187 L / ha.
[00115] The treatments consisted of 4- amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) -pyridine-2-carboxylic acid or esters (compound A ), each formulated as a SC (Suspensi- on Concentrate - concentrate in suspension) and several herbicidal components individually and in combination. Compound A forms were applied based on acid equivalent.
[00116] Forms of compound A (compound of Formula I) tested include:

[00117] Other herbicidal components were applied based on an acid equivalent or active ingredient and included the synthase inhibiting herbicide 5-enolpyruvylchiquime-3-phosphate (5- EnolPyruvylShikimate-3-Phosphate Synthase - EPSPS), isopropylamine salt glyphosate, formulated as Durango DMA® and the glutamine synthase inhibiting herbicide (Glutamine Synthase - GS), glufosinate ammonium, formulated as Ignite® 280.
[00118] For treatments comprised of formulated compounds, measured amounts of compounds were placed individually in 25 ml_ glass bottles and diluted in a volume of 1.25% (v / v) of Agri-Dex® Crop Oil concentrated for obtain 6X stock solutions. If a test compound did not readily dissolve, the mixture was heated and / or sonicated. Application solutions were prepared by adding an adequate amount of each stock solution (typically 2 ml) and diluted to the appropriate final concentrations with the addition of a 1.25% (v / v) aqueous Crop Oil mixture and water, so that the final spray solutions contain 1.25% (v / v) of concentrated Crop Oil.
[00119] For treatments comprised of technical compounds, heavy amounts can be placed individually in 25 ml_ glass vials and dissolved in a 97: 3 v / v volume of acetone / DMSO to obtain 6X stock solutions. If a test compound does not readily dissolve, the mixture can be heated and / or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (eg 2 ml) and diluted to the appropriate final concentrations with the addition of a 1.5% aqueous Crop Oil concentrate (v / v), so that the final spray solutions contain 1.25% (v / v) of concentrated Crop Oil. When technical materials are used, concentrated stock solutions can be added to the spray solutions, so that the final concentrations of acetone and DMSO of the solutions for application are 16.2% and 0.5%, respectively.
[00120] For treatments comprised of formulated and technical compounds, heavy quantities of the technical materials can be placed individually in 25 ml_ glass vials and dissolved in a 97: 3 v / v volume of acetone / DMSO to obtain 6X stock solutions and measured amounts of the formulated compounds can be placed individually in 25 ml glass bottles and diluted in a volume of 1.5% (v / v) concentrated Crop Oil or water to obtain 6X stock solutions. If a test compound does not readily dissolve, the mixture can be heated and / or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (for example, 2 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of a 1.5% aqueous mixture (v / v) concentrated Crop Oil, so that the final spray solutions contain 1.25% (v / v) concentrated Crop Oil. When required, additional water and / or 97: 3 v / v acetone / DMSO can be added to the individual application solutions, so that the final acetone and DMSO concentrations of the application solutions being compared are 8.1 % and 0.25%, respectively.
[00121] All stock solutions and application solutions were visually checked for compound compatibility before application. Compost requirements were based on an application volume of 12 mL at a rate of 187 liters per hectare (L / ha). Formulated compounds were applied to the plant material with an Overhead Mandel Track sprayer equipped with 8002E nozzles calibrated to distribute 187 L / ha over an application area of 0.503 square meters (m2) at a spray height of 46 to 50 cm (18 to 20 inches) above the average plant crown height. Control plants were sprayed in the same way with solvent (blank).
[00122] The treated plants and control plants were placed in a greenhouse as described above and watered by means of sub-irrigation to prevent washing of test compounds. After approximately 2 weeks, the condition of the test plants, when compared to untreated plants, was determined visually and rated on a scale of 0 to 100 percent, where 0 corresponds to the absence of damage or inhibition of growth and 100 corresponds to death complete.
[00123] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: Expected = A + B - (A x B / 100)
[00124] A = observed effectiveness of active ingredient A at the same concentration as used in the mixture
[00125] B = observed effectiveness of active ingredient B at the same concentration as used in the mixture
[00126] Some of the tested compounds, application rates employed, plant species tested and results are provided in Tables 13-15. Table 13. Synergistic Activity of Herbicidal Compositions of Compound A - Acid and Glyphosate Dimethylamine Salt (Durango DMA®) for Foliar Application in the Control of Weeds Common to Crops in Grooves, such as Corn and Soy Culture Systems
Table 14. Synergistic Activity of Compound A Herbicidal Compositions - Glufosinate Acid and Salt Foliar Application in the Control of Weeds Common to Crops in Grooves, such as Corn and Soy Culture Systems

Table 15, Synergistic Activity of Herbicidal Compositions of Compound A - Benzyl Ester and Glufosinate Ammonium Salt for Foliar Application in the Control of Weeds Common to Crops in Grooves, such as Corn and Soy Culture Systems


Example IV. Evaluation of Herbicidal Mixtures of Foliar Application Post-emergence for Weed Control in General
[00127] Seeds or grains of the desired test plant species were planted in a Sun Gro Metro-Mix® 360 planting mix which typically has a pH of 6.0 to 6.8 and an organic matter content about 30 percent, in plastic pots with a surface area of 84.6 square centimeters (cm2). When necessary to ensure good germination and healthy plants, a fungicide treatment and / or other chemical or physical treatment was applied. The plants were grown for 7-31 days in a greenhouse with a photoperiod of approximately 15 h, which was maintained at about 23-29 'C during the day and 22-28' C during the night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg) and water were added on a regular basis and supplementary lighting was provided with 1000 Watt metal halide lamps as needed. The plants were used for testing when they reached the stage of first, second or third true leaves.
[00128] Treatment requirements were calculated based on the rates being tested, the concentration of the active ingredient or acid equivalent in the formulation and an application volume of 12 ml_ at a rate of 187 L / ha.
[00129] The treatments consisted of 4-amino-3-chloro-5-fluor-6- (4-chloro-2-fluor-3-methoxy-phenyl) -pyridine-2-carboxylic acid or benzyl ester ( compound A), each formulated as a SC and several herbicidal components individually and in combination. Compound A forms were applied based on acid equivalent.
[00130] Forms of compound A (compound of Formula I) tested include:

[00131] Other herbicidal components were applied based on an acid equivalent or active ingredient and included the synthase inhibiting herbicide 5-enolpyruvylchiquimate-3-phosphate (5- EnolPyruvylShikimate-3-Phosphate Synthase - EPSPS), glyphosate isopropylamine salt , formulated as Durango DMA® and the glutamine synthase inhibiting herbicide (Glutamine Synthase - GS), glufosinate ammonium, formulated as Ignite® 280.
[00132] For treatments comprised of formulated compounds, measured quantities of compounds were placed individually in 25 ml glass bottles and diluted in a volume of Agri- Dex® Crop Oil concentrated at 1.25% (v / v) to get 12X stock solutions. If a test compound does not readily dissolve, the mixture can be heated and / or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (typically 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of a 1.25% (v / v) aqueous mixture of Agri-Dex® Crop Oil concentrate, so that the final spray solutions contain 1.25% (v / v) of concentrated Agri-Dex® Crop Oil.
[00133] All stock solutions and solutions for application were visually checked for compatibility of compounds before application. Compost requirements were based on an application volume of 12 mL at a rate of 187 liters per hectare (L / ha). Formulated compounds were applied to the plant material with an Overhead Mandel Track sprayer equipped with 8002E nozzles calibrated to distribute 187 L / ha over an application area of 0.503 square meter (m2) at a spray height of 46 to 50 cm (18 to 20 inches) ) above the average plant crown height. Control plants were sprayed in the same way with solvent (blank).
[00134] The treated plants and control plants were placed in a greenhouse as described above and watered by means of sub-irrigation to prevent washing of test compounds. After approximately 3 weeks, the condition of the test plants, when compared to untreated plants, was determined visually and rated on a scale of 0 to 100 percent, where 0 corresponds to the absence of damage or inhibition of growth and 100 corresponds to death complete.
[00135] Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, SR 1967. Calculation of The Synergistic and Antagonistic Response of Herbicide Combinations. Weeds 15: 20-22).
[00136] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: Expected = A + B - (A x B / 100)
[00137] A = observed effectiveness of active ingredient A at the same concentration as used in the mixture
[00138] B = observed effectiveness of active ingredient B at the same concentration as used in the mixture
[00139] Some of the tested compounds, application rates employed, plant species tested and results are provided in Tables 16-17. Table 16. Synergistic Activity of Herbicidal Compositions of Compound A - Benzyl Ester and Glyphosate Dimethylamine Salt (Durango DMA®) for Foliar Application in Weed Control in General


Table 17. Synergistic Activity of Herbicidal Compositions of Compound A - Benzyl Ester and Folium Glufosinate Ammonium Salt for Weed Control in General





Example V, Evaluation of Post-emergence Foliar Herbicidal Mixtures for Weed Control in General
[00140] Seeds or root cuts of the desired test plant species were planted in a Sun Gro Meter-Mix® 360 planting mix which typically has a pH of 6.0 to 6.8 and a content of organic matter of about 30 percent, in plastic pots with a surface area of 126.6 square centimeters (cm2). When necessary to ensure good germination and healthy plants, a fungicide treatment and / or other chemical or physical treatment was applied. The plants were grown for 9-30 days in a greenhouse with a photoperiod of approximately 14 h, which was maintained at about 28 ° C during the day and 24 ° C at night. Nutrients and water were added on a regular basis and supplementary lighting was provided with 1000 Watt metal halide lamps as needed. The plants were used for testing when they reached the stage of BBCH11 to BBCH14 leaves.
[00141] The treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) -pyridine-2-carboxylic acid (compound A) formulated as a SC and a glyphosate-containing herbicide. A measured aliquot of Compound A - Benzyl Ester was placed in a 25 milliliter (ml_) glass bottle and diluted in a volume of distilled water or 1.25% by volume / volume (v / v) of Agridex® Crop Concentrated oil to obtain stock solutions. Compost requirements are based on an application volume of 12 mL at a rate of 187 liters per hectare (L / ha). Solutions for spraying the herbicide containing glyphosate and mixtures of experimental compounds were prepared by adding to the stock solutions the appropriate amount of dilution solution to form 12 mL of spray solution with active ingredients in the biphasic combinations. Formulated compounds were applied to the plant material with an Overhead Mandel Track sprayer equipped with 8002E nozzles calibrated to distribute 187 L / ha over an application area of 0.503 square meters (m2) at a spray height of 18 inches (43 cm) above the average plant crown height. Control plants were sprayed in the same way with solvent (blank).
[00142] The treated plants and control plants were placed in a greenhouse as described above and watered by means of sub-irrigation to prevent washing of test compounds. After approximately 21 days, the condition of the test plants, when compared to the control plants, was determined visually and classified on a scale from 0 to 100 percent, where 0 corresponds to the absence of damage and 100 corresponds to complete death.
[00143] Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, SR 1967. Calculation of The Synergistic and Antagonistic Response of Herbicide Combinations. Weeds 15: 20-22).
[00144] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: Expected = A + B - (A x B / 100)
[00145] A = observed effectiveness of active ingredient A at the same concentration as used in the mixture
[00146] B = observed effectiveness of active ingredient B at the same concentration as used in the mixture
[00147] Some of the tested compounds, application rates employed, plant species tested and results are provided in Tables 18-21. Table 18. Synergistic Activity of Herbicidal Compositions of Compound A - Benzyl Ester and Herbicide Rodeo® (Glyphosate) Foliar Application Formulated in Distilled Water in Weed Control in General
Table 19. Synergistic Activity of Compound A Herbicidal Compositions - Benzyl Ester and Herbicide Glyphomax Plus (Glyphosate) Foliar Application Formulated in Distilled Water to Control Weeds in General
Table 20. Synergistic Activity of Herbicidal Compositions of Compound A - Benzyl Ester and Herbicide Rodeo® (Glyphosate) with Foliar Application Formulated in 1.25% COC in Weed Control in General

Table 21. Synergistic Activity of Compound A Herbicidal Compositions - Benzyl Ester and Glyphomax Plus Herbicide (Glyphosate) Foliar Application Formulated in 1.25% COC in Weed Control in General

权利要求:
Claims (9)
[0001]
1. Synergistic herbicidal composition, characterized by the fact that it comprises a herbicidally effective amount of: (a) a compound of Formula (I),
[0002]
2. Composition, according to claim 1, characterized by the fact that it also comprises an agriculturally acceptable adjuvant or vehicle.
[0003]
3. Composition according to claim 1 or 2, characterized by the fact that it also comprises a herbicide protector.
[0004]
4. Method for controlling undesirable vegetation, characterized by the fact that it comprises the step of contacting a plant, the plant being a vegetation, or location of it, soil or water, with soil or water allowing the growth of undesirable vegetation, with a herbicidally effective amount of a composition, as defined in any one of claims 1 to 3.
[0005]
5. Method, according to claim 4, characterized by the fact that undesirable vegetation is controlled in rice directly grown, rice grown in water and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, green corn / corn , sugar cane, sunflower, rapeseed, canola, beet, soy, cotton, pineapple, pastures, fields, pastures, idle land, grass, trees and orchards, aquatic plants, industrial vegetation management (Industrial Vegetation Management - IVM) or easements (Rights-Of-Way - ROW).
[0006]
6. Method according to claim 4 or 5, characterized by the fact that (a) and (b) are applied pre-emergently to the plant or crop.
[0007]
Method according to any one of claims 4 to 6, characterized by the fact that undesirable vegetation is controlled in tolerants to glyphosate, 5-enolpyruvylchiquimate-3-phosphate synthase (5-EnolPyruvylShikimate-3-Phosphate - EPSP) , glufosinate, glutamine synthase inhibitor, dicamba, phenoxy auxin, pyridyloxy auxin, synthetic auxin, auxin transport inhibitor, aryloxy phenoxy propionates, cyclohexanedione, phenylpyrazoline, acetyl CoA carboxylase inhibitor (Acetyl ÇoA Carboxase), imidazolinone, sulfonylurea, pyrimidinylthiobenzoate, triazolopyrimidine, sulfonylaminocarbonyltriazolinone, acetolactate synthase inhibitor (AcetoLactate Synthase - ALS) or acetohydroxy acid (AcetoHyro-Hydroxy-Hydroxy-4-Hydroxy-Hydroxy-Hydroxy-Hydroxy-Acids), Pyruvate-Dioxygenase - HPPD), phytoene desaturase inhibitor, carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase inhibitor (Pro toPorphyrinogen Oxidase - PPO), cellulose biosynthesis inhibitor, mitosis inhibitor, microtubule inhibitor, very long chain fatty acid inhibitor, lipid and fatty acid biosynthesis inhibitor, photosystem I inhibitor, photosystem II inhibitor, triazine or bromoxynil.
[0008]
8. Method, according to claim 7, characterized by the fact that the tolerant culture has multiple or stacked traits that confer tolerance to multiple herbicides or multiple modes of action.
[0009]
Method according to any one of claims 4 to 8, characterized in that the undesirable vegetation comprises a herbicide resistant or tolerant plant.

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法律状态:
2015-03-03| B03A| Publication of a patent application or of a certificate of addition of invention [chapter 3.1 patent gazette]|

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2016-10-11| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]|

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2018-09-11| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

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2019-01-08| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

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2019-11-05| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

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2020-04-07| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2020-10-27| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 22/07/2013, OBSERVADAS AS CONDICOES LEGAIS. |

优先权:

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申请号 | 申请日 | 专利标题

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US201261675083P| true| 2012-07-24|2012-07-24|

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US61/675,083|2012-07-24|

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US13/836,653|2013-03-15|

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US13/836,653|US8895470B2|2012-07-24|2013-03-15|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and glyphosate or glufosinate|

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