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

专利摘要:
herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and auxin transport inhibitors. a composition containing herbicide is provided here, and a method for controlling undesirable vegetation using (a) a compound according to formula (1): 4-amino-3-chloro-5-fluoro-6- (4-chloro acid) -2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic or an agriculturally acceptable salt or ester thereof and (b) an auxin transport inhibitor. examples of auxin transport inhibitors include chlorflurenol-methyl, diflufenzopyr-sodium, flurenol-methyl and naptalam-sodium, or an agriculturally acceptable salt or ester derivative thereof. the methods and compositions described here provide control of undesirable vegetation, for example, in rice, cereals, wheat, barley, oats, rye, sorghum, corn or hominy, sugar cane, sunflower, rapeseed, canola, sugar beet sugar, soy, cotton, pineapple, vegetables, pasture, pasture, fallow land, lawn, orchards of trees and vines, aquatic vegetation, plantation harvest, industrial vegetation management (ivm) or strips of easement (row).
公开号:BR102013018482B1
申请号:R102013018482
申请日:2013-07-19
公开日:2020-02-04
发明作者:Yerkes Carla；Mann Richard
申请人:Dow Agrosciences Llc；
IPC主号:

专利说明:

Invention Patent Descriptive Report for HERBICIDAL COMPOSITIONS UNDERSTANDING 4-AMINO-3-CHLORINE-5-FLUORIC ACID (6- (4-CHLORINE-2-FLUOR-3-METOXYPHYL) PYRIDINE-2-CARBOXYLIC OR A DERIVATIVE OF THE SAME AND TRANSPORT INHIBITORS OF AUXINE, AND METHOD TO CONTROL THE UNDESIRABLE VEGETATION.
Priority Claim [001] This application claims the benefit of provisional patent application No. US 61 / 675,093, filed on July 24, 2012, and patent application No. US 13 / 834,706, filed on 15 March 2013, the disclosure of each of which is incorporated here by reference in its entirety.
Field of the Art [002] Herbicidal compositions are provided here comprising (a) 4-amino-3-chloro-5-fluorine-6- (4-chloro-2-fluor-3methoxyphenyl) pyridine-2-carboxylic acid or an ester agriculturally acceptable or salt thereof and (b) an auxin transport inhibitor.
[003] Methods are also provided here to control undesirable vegetation comprising the application of (a) 4 amino-3-chloro-5-fluorine-6- (4-chloro-2-fluor-3-methoxyphenyl) pyridine-2-carboxylic acid or an agriculturally acceptable ester or salt thereof and (b) an inhibitor of auxin transport.
Background [004] Crop protection against weeds and other vegetation that inhibits crop growth is a problem that constantly occurs in agriculture. To help combat this problem, researchers in the field of chemical synthesis have produced an extensive variety of chemicals and chemical formulations effective in controlling such unwanted growth. Many types of chemical herbicides have been reported in the literature and a large number
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2/86 ro is in commercial use. However, there is a need for compositions and methods that are effective in controlling undesirable vegetation.
Summary [005] A first embodiment of the invention provided here includes herbicidal compositions comprising a herbicidally effective amount of (a) a compound according to Formula (I)
X '(h H ^ C or an agriculturally acceptable salt or ester thereof, and (b) at least one auxin transport inhibitor.
[006] A second embodiment includes mixing the first embodiment in which the compound of Formula (I) is present in the form of at least one of the following forms: a carboxylic acid, a carboxylate salt, an aralkyl, an alkyl ester, an unsubstituted benzyl, a substituted benzyl, a C1-4 alkyl, and / or an n-butyl ester.
[007] A third modality includes the mixture according to either the first or the second modality in which (b) at least one auxin transport inhibitor is at least one compound selected from the group consisting of: methyl chlorflurenol, chlorflurenol, diflufenzopyr , diflufenzopyr sodium, methyl flurenol, flurenol, and naptalam, or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof of at least one of the above mentioned inhibitors of
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3/86 transport of the auxin.
[008] A fourth embodiment includes mixtures according to any of the first, second, or third embodiments in which the auxin transport inhibitor in the mixture is methyl chlorflurenol or chlorflurenol in which the weight ratio of the compound according to Formula ( I) for methyl chlorflurenol or chlorflurenol given in units of gae / ha to gai / ha or gae / ha to gae / ha is selected from the group of ranges of ratios and ratios consisting of: 4.4: 1, 1: 3.9, 1: 7.9, 1: 15.7, 1: 31.4, 1: 62.8, 1: 125.6, from 1: 15.7 to 1: 62.8, 1: 1680 , from 1: 3.9 to 1: 62.8, from 1: 7.9 to 1: 62.8, from 1: 15.7 to 1: 125.6 from 1: 15.7 to 1:62, 8, from approximately 1: 125 to approximately 1: 2, from approximately 1:16 to approximately 1:31, from approximately 1: 8 to approximately 1:16, from 4.4: 1 to approximately 1: 1680, or within any of the ranges of variation defined between any pairs of the preceding values.
[009] A fifth embodiment includes mixtures according to any of the first, second, or third embodiments in which the auxin transport inhibitor. in the mixture is diflufenzopyr or diflufenzopyr sodium in which the weight ratio between the compound according to Formula (I) to diflufenzopyr or diflufenzopyr sodium given in units of gae / ha to gai / ha or gae / ha to gae / ha is selected of the range of ranges of ratios and ratios consisting of: 86: 1, 2: 1, 1.8: 1, 1: 1, 1: 1.1, 1: 2, 1: 2.2, 1: 4 , 1: 4,4, 1: 8, 1: 8,8, 1:18, 2: 1 to 1: 4, 2: 1 to 1: 8, 1.8: 1 to 1: 8, 8, from approximately 1:16 to 4: 1, from approximately 1: 2 to approximately 1: 4, from approximately 1: 1 to approximately 1: 2, from 1: 1680 to 4.4: 1, or within any one the ranges of variation defined between any pairs of the preceding values.
[0010] A sixth modality includes mixtures according to any of the first, second, or third modalities in
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4/86 which inhibitor of auxin transport in the mixture is methyl flurenol or flurenol in which the weight ratio between the compound according to Formula (I) and the methyl flurenol or flurenol given in units of gae / ha to gai / ha or gae / ha for gae / ha is selected from the group of ranges of ratios and ratios consisting of: 4.4: 1, 1: 2.2, 1: 4.3, 1: 8.6, 1:17 , 2, 1: 34,4, from 1: 8.6 to 1: 34,4, 1: 1680, from approximately 1:35 to approximately 1: 2, from approximately 1: 8 to approximately 1:17, from 1 : 2.2 to 1: 17.2, from 4.4: 1 to 1: 1680, or within any of the ranges of variation defined between any pairs of the preceding values.
[0011] A seventh embodiment includes mixtures according to any of the first, second, or third embodiments in which the auxin transport inhibitor in the mixture is naptalam in which the weight ratio of the compound according to Formula (I) for naptalam given in units of gae / ha to gai / ha or gae / ha to gae / ha it is selected from the group of ranges of variation of ratios and ratios consisting of: 2: 1, 1.1: 1, 1: 1 , 9, 1: 3.8, 1: 7.5, 1: 10.3, 1:15, 1: 20.6, 1: 41.3; 1: 82.5, 1: 165, 1: 2250, from 1: 1.9 to 1:15, from 1.1: 1 to 1:15, from approximately 1: 165 to 1: 1, from approximately 1: 4 to approximately 4: 1, from 1: 10.31 to 1: 165, from 2: 1 to 1: 2250, or within any of the ranges of variation defined between any pairs of the preceding values.
[0012] An eighth modality includes any composition according to any one of the first to the seventh modalities wherein the mixture additionally comprises at least one component selected from the group consisting of an agriculturally acceptable agent, an adjuvant, a vehicle, or a protector.
[0013] A ninth modality includes methods for controlling undesirable vegetation comprising the application stage or otherwise contacting vegetation and / or soil, and / or water with a quantity
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5/86 herbicidally effective of at least one mixture according to any one of the first to eighth modalities.
[0014] A tenth modality includes methods according to the ninth modality in which the method is practiced in at least one member of the group consisting of: rice directly sown, sown in water, and / or transplanted, cereals, wheat, barley, oats , rye, sorghum, corn / hominy, sugar cane, sunflower, rapeseed, canola, sugar beet, soy, cotton, pineapple, pasture, pasture, fallow land, lawn, tree and vine orchards, aquatic vegetation, plantation crops, vegetables, industrial vegetation management (IVM), or easements of passage (ROW).
[0015] An eleventh modality includes methods according to any of the ninth and eleventh modalities in which a herbicidally effective amount of the mixture is applied pre- or post-sprouting to at least one of the following: a crop, a field, a ROW, or a Rice with pell.
[0016] A twelfth modality includes methods according to any of the modalities from the ninth to the eleventh in which undesirable vegetation can be controlled in: glyphosate tolerant crops, 5-enolpyruvylshikimato-3-phosphate (EPSP) synthase inhibitor, glufosinate , glutamine synthetase inhibitor, dicamba, phenoxy auxin, pyridyloxy auxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl CoA carboxylase inhibitor (ACCase), imidazolinone, sulfonylylamine, trifluimylylamine triazolinone, acetolactate synthase (ALS) or acetohydroxy acid synthetase (AHAS) inhibitors, 4-hydroxy phenyl pyruvate dehydrogenase (HPPD) inhibitor, phytene desaturase inhibitor, carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase inhibitor, oxidase protease cellulose biosynthesis, mitosis inhibitor, miPetition inhibitor 87018 0163099, of 12/14/2018, p. 10/112
6/86 crotubule, very long chain fatty acid inhibitor, fatty acid and lipid biosynthesis inhibitor, photosystem I inhibitor, photosystem II inhibitor, protoporphyrinogen oxidase (PPO) inhibitor, or to triazine or bromoxynil.
[0017] A thirteenth modality includes at least one method according to any of the ninth modalities until the twelfth in which a plant that is resistant or tolerant to at least one herbicide is treated, and where the resistant or tolerant crop has characteristics multiple or stacked giving tolerance to multiple herbicides or herbicide inhibitors of multiple modes of action, in some modalities the treated plant that expresses tolerance or resistance to an herbicide is the vegetation itself undesirable.
[0018] A fourteenth modality includes methods according to the thirteenth modality, in which the resistant or tolerant weed is a biotype with resistance or tolerance to multiple herbicides, multiple chemical classes, hebicide inhibitors with multiple modes of action, or via multiple herbicide resistance mechanisms.
[0019] A fifteenth modality includes at least one of the methods according to the thirteenth and fourteenth modalities, in which the resistant or tolerant undesirable plant is a resistant or tolerant biotype to at least one agent selected from the group consisting of: inhibitors acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS), photosystem II inhibitors, acetyl CoA carboxylase inhibitors (ACCase), synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5enolpyruvylshikimato-3-phosphate inhibitors (EPSP) synthetase, microtubule assembly inhibitors, fatty acid synthesis and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, inhibitors
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7/86 carotenoid biosynthesis, very long chain fatty acid inhibitors (VLCFA), phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenylpyruvatodioxigenase (HPPD) inhibitors, mitosis inhibitors, inhibitors of cellulose biosynthesis, herbicides with multiple modes of action, quinclorac, arylaminopropionic acids, difenzoquat, endothal, or organoarsenic.
[0020] A sixteenth modality includes methods for 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 in a rate, expressed in gai / ha or gae / ha of methyl chlorflurenol or chlorflurenol selected from the group of rates and rate ranges consisting of approximately: 68.75, 137.5, 275, 550 or within any of the ranges defined between any pairs of previous values.
[0021] A seventeenth modality includes methods according to any of the fourth and sixteenth modalities in which the controlled plant is at least one plant selected from the group consisting of: ECHCG, ECHCO, CYPIR, LEFCH, IPOHE, DIGSA, ECHOR, SCPMA, in any case other modalities include genus control plants consisting of: Echinochloa, Cyperus, Leptochloa, Ipomoea, Digitaria, Schoenoplectus, and Bolboschoenus.
[0022] An eighteenth modality includes methods for controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the fifth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of diflufenzopyr or diflufenzopyr sodium selected from the group of rates and rate ranges consisting of approximately: 8.75, 17.5, 35, 70, or within any of the range ranges defined among whichPetition 870180163099 , of 12/14/2018, p. 10/13
8/86 or pairs of previous values.
[0023] A nineteenth modality includes methods according to any of the fifth and eighteenth modalities in which the controlled plant is at least one plant selected from the group consisting of: BRAPP, LEFCH, DIGSA, IPOHE, ECHCG, CYPRO, FIMMI, in any case, other modalities include genus control plants consisting of: Brachiaria, Leptochloa, Digitaria, Ipomoea, Echinochloa, Cyperus, and Fimbristylis.
[0024] A twentieth modality includes methods to control undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the sixth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gaur / ha of flurenol or methyl flurenol selected from the group of rates and rate ranges consisting of approximately: 68.75, 137.5, 275, or within any of the ranges defined between any pairs of the preceding values .
[0025] A twenty-first modality includes methods according to any of the sixth and twentieth modalities in which the controlled plant is at least one plant selected from the group consisting of: BRAPP, CYPIR, ECHCG, FIMMI, CYPRO yet other modalities include plants of genus control consisting of: Brachiaria, Cyperus, Echinochloa, Fimbristylis, and Cyperus.
[0026] A twenty-second modality includes methods to control undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the seventh modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of naptalam selected from the group of rates and rate range ranges consisting of approximately: 30, 60, 120, 330, 660, 1320, or within which
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9/86 or one of the ranges of variation defined between any pairs of the preceding values.
[0027] A twenty-three modality includes methods according to any of the seventh and twenty-second modalities in which the controlled plant is at least one plant selected from the group consisting of: BRAPP, LEFCH, IPOHE, ECHCG, FIMMI, ECHOR, CYPRO, in any case other modalities include plants of genus control consisting of: Brachiaria, Leptochloa, Ipomoea, Echinochloa, Fimbristylis, Echinochloa, and Cyperus.
[0028] Herbicidal compositions are provided herein comprising a herbicidally effective amount of (a) a compound according to Formula (I)
or an agriculturally acceptable salt or ester thereof, and (b) an inhibitor of auxin transport. The compositions can also contain an agriculturally acceptable adjuvant or vehicle.
[0029] Methods for controlling undesirable vegetation are also provided here comprising the application of (a) a compound according to Formula (I) or an agriculturally acceptable ester or salt thereof and (b) an inhibitor of auxin transport .
Detailed Description
Definitions [0030] As used herein, the compound according to Formula (I) has the following structure:
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[0031] The compound according to Formula (I) can be identified by the name of 4-amino-3-chloro-6- (4-chloro-2-fluoro-3methoxyphenyl) -5-fluoropyridine-2-carboxylic acid and has been described in US Patent 7,314,849 (B2), which is incorporated herein by reference in its entirety. Exemplary uses of the compound according to Formula (I) include the control of undesirable vegetation, including grass, hardwoods and sedge weeds, in multiple non-harvest and harvest situations.
[0032] Without being limited to any theory, auxin transport inhibitors interfere with the abilities of auxins to mediate plant growth and development. Examples of auxin transport inhibitors include, but are not limited to, methyl chlorflurenol, diflufenzopyr sodium, flurenol, methyl flurenol and naptalam, or salts or esters thereof.
[0033] As used herein, methyl chlorflurenol is methyl oxy-2-chloro-9hydroxy-9H-fluorene-9-carboxylate. Exemplary uses of methyl chlorflurenol are described in Tomlin, C., ed. The World Compendium Te Pesticide Manual. 15th ^to Ed. Alton: BCPC Publications, 2009 (hereafter, Te Pesticide Manual, Fifteenth Edition, 2009.). Exemplary uses of methyl chlorflurenol include its use as a plant growth retardant and weed suppressor, for example, in soft grass, roadside, railroads, and moat edges. Methyl chlorflurenol has the following structure:
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[0034] As used herein, diflufenzopyr is 2 - {(E) -1- [4 (3,5-difluorophenyl) -semicarbazone] -ethyl} nicotinic acid. Exemplary uses of diflufenzopyr are described in Te Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of diflufenzopir include its use of the control of post-sprouting of annual weeds from drop and perennial leaves, for example, in corn, pastures and non-harvest areas. Diflufenzopir has the following structure:
[0035] An exemplary form of diflufenzopyr includes its acid and its sodium salt form, ie diflufenzopyr sodium.
[0036] As used herein, flurenol is 9-hydroxy-9Hfluorene-9-carboxylic acid. Exemplary uses of flurenol are described in Te Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of flurenol include its use of broadleaf weed pest control, for example, in cereal grass and rice. Flurenol has the following structure:
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Ο
[0037] An exemplary form of flurenol includes butyl flurenol, flurenol-dimethylammonium, and methyl florenol.
[0038] As used herein, naptalam is 2 - [(1naphthalenylamino) carbonyl] benzoic acid. It is described in Te Pesticide Manual, Fifteenth Edition, 2009. naptalam has the following structure:
[0039] Exemplary forms of naptalam include its sodium salt, naptalam sodium.
[0040] As used herein, the herbicide means a compound, for example, an active ingredient that kills, controls or otherwise adversely modifies the growth of plants.
[0041] As used herein, a herbicidally effective or vegetation control amount is an amount of the active ingredient that adversely modifies the vegetation, for example, causing deviations from natural development, extermination, effecting regulation, causing desiccation, causing delay, and so on.
[0042] As used herein, controlling undesirable vegetation means preventing, reducing, exterminating, or otherwise adversely modifying the development of plants and vegetation. Are described
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13/86 here methods for controlling undesirable vegetation by applying certain combinations of the herbicide or compositions. Application methods include, but are not limited to, applications to the vegetation or location of the same, for example, application to the area adjacent to the vegetation, as well as pre-sprouting, post-sprouting, leaf (transmitted, directed, joined, blur, mechanically, excessively , or rescue), and water applications (immersed and immersed vegetation, transmitted, blur, mechanical transmitted, water-injected, granular, granular blur, mixer bottle, or spray flow), via manual application methods, spray backpack, spray machine, tractor, or aerial (airplane and helicopter).
[0043] As used herein, plants and vegetation include, but are not limited to, germinating seeds, seedling plants, plants that sprout from vegetative propagules, immature vegetation, and established vegetation.
[0044] As used herein, agriculturally acceptable salts and esters refer to salts and esters that expose herbicide activity, or that are or can be converted to plants, water, or soil in the reference herbicide. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, for example, in plants, in water, or in the soil, to the corresponding carboxylic acid which, depending on the pH, may be in the dissociated or non-dissociated form.
[0045] Exemplary salts include those derived from alkali metals or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium, and amine cations of the Formula:
R1R ² R ³ R ⁴ N ⁺
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14/86 where R ¹ , R ² , R ³ and R ⁴ 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, with the proviso that R ¹ , R ² , R ³ and R ⁴ are sterically compatible. In addition, any two of R ¹ , R ² , R ³ and R ⁴ together can represent an aliphatic difunctional portion containing from one to twelve carbon atoms and up to two sulfur or oxygen 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, cyclododecylamine, or benzylamine or with a tetraalkylammonium hydroxide, such as tetramethylammonium choline hydroxide or hydroxide.
Exemplary esters include derivatives of C1C12-alkyl, C3-C12-alkenyl, C3-C12-alkynyl or aryl alcohols substituted with C-C10-alkyl, such as methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethylanol , butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or substituted or unsubstituted benzyl alcohol. Benzyl alcohols can be substituted with 1 to 3 substituents independently selected from halogen, C1-C4-alkyl or C1-C4-alkoxy. Esters can be prepared by binding acids to alcohol using any number of suitable activating agents such as those used for peptide bonds such as dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); 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; reacting the corresponding acid chloride of an acid with an appropriate alcohol; reacting the corresponding acid with an appropriate alcohol in the presence of an acid catalyst or by transesterification.
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Compositions and Methods [0047] A first embodiment of the invention provided here includes herbicidal compositions comprising a herbicidally effective amount of (a) a compound according to Formula (I)
or an agriculturally acceptable salt or ester thereof, and (b) at least one auxin transport inhibitor.
[0048] A second embodiment includes mixing the first embodiment in which the compound of Formula (I) is present in the form of at least one of the following forms: a carboxylic acid, a carboxylate salt, an aralkyl, an alkyl ester, an unsubstituted benzyl, a substituted benzyl, a C1-4 alkyl, and / or an n-butyl ester.
[0049] A third embodiment includes the mixture according to either the first or the second embodiment in which (b) the at least one auxin transport inhibitor is at least one compound selected from the group consisting of: methyl chlorflurenol, chlorflurenol, diflufenzopyr , diflufenzopyr sodium, methyl flurenol, flurenol, and naptalam, or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester of at least one of the aforementioned auxins carries the inhibitor.
[0050] A fourth embodiment includes mixtures according to any of the first, second, or third embodiments in which the auxin transport inhibitor in the mixture is methyl chlorflurenol or chlorflurenol in which the weight ratio of the compound according
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16/86 with Formula (I) for methyl chlorflurenol or chlorflurenol given in units of gae / ha to gai / ha is selected from the group of ranges of ratios and ratios consisting of 4.4: 1, 1: 3, 9, 1: 7,9, 1: 15,7, 1: 31,4, 1: 62,8, 1: 125,6, from 1: 15,7 to 1: 62,8, 1: 1680, from 1: 3.9 to 1: 62.8, 1: 7.9 to 1: 62.8, 1: 15.7 to 1: 125.6, 1: 15.7 to 1: 62.8 , from approximately 1: 125 to approximately 1: 2, from approximately 1:16 to approximately 1:31, forms approximately 1: 8 to approximately 1:16, from 4.4: 1 to approximately 1: 1680, or within any one of the ranges of variation defined between any pairs of the preceding values.
[0051] A fifth embodiment includes mixtures according to any of the first, second, or third modalities in which the auxin transport inhibitor in the mixture is diflufenzopyr or diflufenzopyr sodium in which the weight ratio of the compound according to Formula (I) for diflufenzopyr or diflufenzopyr sodium given in units of gae / ha to gai / ha is selected from the group of ranges of ratios and ratios consisting of: 86: 1, 2: 1, 1.8: 1, 1: 1, 1: 1,1, 1: 2, 1: 2,2, 1: 4, 1: 4,4, 1: 8, 1: 8,8, 1:18, from 2: 1 to 1 : 4, from approximately 1:16 to approximately 4: 1, from approximately 1: 2 to approximately 1: 4, from approximately 1: 1 to approximately 1: 2, from 2: 1 to 1: 8, from 1.8: 1 to 1: 8.8, 1: 1680 to 4.4: 1, or within any of the ranges defined between any pairs of the preceding values.
[0052] A sixth modality includes mixtures according to any of the first, second, or third modalities in which the auxin transport inhibitor in the mixture is methyl flurenol or flurenol in which the weight ratio between the compound according to the Formula (I) and the methyl flurenol or flurenol given in units of gae / ha to gai / ha is selected from the group of variation ranges of the ratios and ratios consisting of: 4.4: 1, 1: 2.2, 1: 4 , 3, 1: 8,6, 1: 17,2,
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1: 34.4, from 1: 8.6 to 1: 34.4, 1: 1680, from 1: 2.2 to 1: 17.2, from approximately 1:34 to 1: 2, from approximately 1: 8 to approximately 1:17, from 4.4: 1 to 1: 1680, or within any of the ranges of variation defined between any pairs of the preceding values.
[0053] A seventh embodiment includes mixtures according to any of the first, second, or third embodiments in which the auxin transport inhibitor in the mixture is naptalam in which the weight ratio of the compound according to Formula (I) for naptalam given in units of gae / ha to gai / ha it is selected from the group of ranges of variation of the ratios and ratios consisting of: 2: 1, 1.1: 1, 1: 1.9, 1: 3.8 , 1: 7,5, 1: 10,3, 1:15, 1: 20,6, 1: 41,3; 1: 82.5, 1: 165, 1: 2250, from 1: 165 to approximately 1; the 1, from approximately 1: 4 to approximately 1:41, from 1: 1.9 to 1:15, from 1.1: 1 to 1:15, from 1: 10.31 to 1: 165, from 2: 1 to 1: 2250, or within any of the ranges defined between any pairs of the preceding values.
[0054] An eighth embodiment includes any composition according to any one of the first to the seventh embodiments wherein the mixture additionally comprises at least one component selected from the group consisting of an agriculturally acceptable agent, an adjuvant, a vehicle, or a protector.
[0055] A ninth modality includes methods for controlling undesirable vegetation comprising the application stage or otherwise contacting vegetation and / or soil, and / or water with a herbicidally effective amount of at least one mixture according to any of the first to eighth modalities.
[0056] A tenth modality includes methods according to the ninth modality in which undesirable vegetation is controlled according to at least one technique selected from the group consisting of: rice directly sown, sown in water, and / or transplanted, cereals, wheat , barley, oats, rye, sorghum, corn / hominy, cane
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18/86 sugar, sunflower, rapeseed, canola, sugar beet, soy, cotton, pineapple, pasture, pasture, fallow land, lawn, tree and vine orchards, aquatic vegetation, plantation crops, vegetables, industrial management vegetation (IVM), or easements of passage (ROW).
[0057] An eleventh modality includes methods according to any of the ninth and eleventh modalities in which a herbicidally effective amount of the mixture is applied pre- or post-sprouting to at least one of the following: a crop, a field, a ROW, or a Rice with pell.
[0058] A twelfth modality includes methods according to any of the modalities from the ninth to the eleventh in which undesirable vegetation can be controlled in crops tolerant to: be controlled in: crops tolerant to glyphosate, 5-enolpiruvilshikimato synthase inhibitor -3-phosphate (EPSP), glufosinate, glutamine synthetase inhibitor, dicamba, phenoxy auxin, pyridyloxy auxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl CoA carboxylase inhibitor (ACCase), ACCase imidazolinone, sulfonylurea, pyrimidinylthiobenzoate, triazolpyrimidine, sulfonylaminocarbonyltriazolinone, acetolactate synthase (ALS) or acetohydroxy acid synthetase (AHAS) inhibitor, 4-hydroxyphenyl pyruvate dehydrogensis, protease inhibitor, protease inhibitor (HPP) inhibitor (PPO), cellulose biosynthesis inhibitor, d mitosis, microtubule inhibitor, very long chain fatty acid inhibitor, fatty acid and lipid biosynthesis inhibitor, photosystem I inhibitor, photosystem II inhibitor, protoporphyrinogen oxidase (PPO) inhibitor, or triazine or bromoxynil .
[0059] A thirteenth modality includes at least one method according to any of the ninth to the thirteenth modalities
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19/86 second in which a plant that is tolerant to at least one herbicide is treated, and where the tolerant crop has multiple or stacked characteristics conferring tolerance to multiple herbicides or inhibitors of multiple modes of action, in some modalities the treated plant that expresses resistance to a herbicide is undesirable vegetation itself.
[0060] A fourteenth modality includes methods according to the thirteenth modality, in which the resistant or tolerant weed is a biotype with resistance or tolerance to multiple herbicides, multiple chemical classes, hebicide inhibitors with multiple modes of action, or via multiple resistance mechanisms.
[0061] A fifteenth modality includes at least one of the methods according to the thirteenth and fourteenth modalities, in which the resistant or tolerant undesirable plant is a resistant biotype or tolerant to at least one agent selected from the group consisting of: inhibitors acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS), photosystem II inhibitors, acetyl CoA carboxylase inhibitors (ACCase), synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5enolpyruvylshikimato-3-phosphate inhibitors (EPSP) synthase, microtubule assembly inhibitors, fatty acid synthesis and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid inhibitors (VLCFA), inhibitors phytene desaturase (PDS), glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvatodioxigenase (HPPD) inhibitors, inhibitor s of mitosis, cellulose biosynthesis inhibitors, herbicides with multiple modes of action, quinclorac, arylaminopropionic acids, difenzoquat, endothal, or organoarsenic.
[0062] A sixteenth modality includes methods to control undesirable vegetation comprising the stage of applying a
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20/86 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 ai / ha of methyl chlorflurenol or chlorflurenol selected from the group of rates and rate ranges consisting of approximately: 68.75, 137.5, 275, 550 or within any of the ranges defined between any pairs of the preceding values.
[0063] A seventeenth modality includes methods according to any of the fourth and sixteenth modalities in which the controlled plant is at least one plant selected from the group consisting of: ECHCG, ECHCO, CYPIR, LEFCH, IPOHE, DIGSA, ECHOR, SCPMA, in any case other modalities include genus control plants consisting of: Echinochloa, Cyperus, Leptochloa, Ipomoea, Digitaria, Schoenoplectus, and Bolboschoenus.
[0064] An eighteenth modality includes methods for controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the fifth modality in which the amount of the mixture is applied at a rate, expressed in ai / ha of diflufenzopyr or diflufenzopyr sodium selected from the group of rates and rate ranges consisting of approximately: 8.75, 17.5, 35, 70, or within any of the ranges defined between any pairs of the preceding values.
[0065] A nineteenth modality includes methods according to any of the fifth and eighteenth modalities in which the controlled plant is at least one plant selected from the group consisting of: BRAPP, LEFCH, DIGSA, IPOHE, ECHCG, CYPRO, FIMMI, in any case, other modalities include genus control plants consisting of: Brachiaria, Leptochloa, Digitaria, Ipomoea, Echinochloa, Cyperus, and Fimbristylis.
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21/86 [0066] A twentieth modality includes methods to control undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the sixth modality in which the amount of the mixture is applied in a rate, expressed in ai / ha of flurenol or methyl flurenol selected from the group of rates and rate ranges consisting of approximately: 68.75, 137.5, 275, or within any of the ranges defined between any pairs of the preceding values.
[0067] A twenty-first modality includes methods according to any of the sixth and twentieth modalities in which the controlled plant is at least one plant selected from the group consisting of: BRAPP, CYPIR, ECHCG, FIMMI, CYPRO yet other modalities include plants of genus control consisting of: Brachiaria, Cyperus, Echinochloa, Fimbristylis, and Cyperus.
[0068] A twenty-second modality includes methods for controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the seventh modality in which the amount of the mixture is applied at a rate, expressed in ai / ha of naptalam selected from the group of rates and rate ranges consisting of approximately: 30, 60, 120, 330, 660, 1320, or within any of the ranges defined between any pairs of the preceding values.
[0069] A twenty-three modality includes methods according to any of the seventh and twenty-second modalities in which the controlled plant is at least one plant selected from the group consisting of, BRAPP, LEFCH, IPOHE, ECHCG, FIMMI, ECHOR, CYPRO, in any case other modalities include genus control plants consisting of: Brachiaria, Leptochloa, Ipomoea,
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Echinochloa, Fimbristylis, Echinochloa, and Cyperus.
[0070] Herbicidal compositions are provided herein comprising a herbicidally effective amount of (a) a compound according to Formula (I)
or an agriculturally acceptable salt or ester thereof, and (b) an inhibitor of auxin transport.
[0071] Methods are also provided here to control undesirable vegetation comprising contacting the vegetation or its location, that is, the area adjacent to the vegetation, with or applying to the soil or water to prevent the sprouting or growth of the vegetation a herbicidally effective amount of the compound according to Formula (I) or an agriculturally acceptable salt or ester thereof and (b) an auxin transport inhibitor. In certain embodiments, the methods employ the compositions described here.
[0072] In certain embodiments of the compositions and methods, the auxin transport inhibitor is methyl chlorflurenol, diflufenzopyr, flurenol and naptalam, or an agriculturally acceptable salt or ester thereof.
[0073] In addition, in some embodiments, the combination of compound (I) or agriculturally acceptable salt or ester thereof, and an auxin transport inhibitor, including, but not limited to methyl chlorflurenol, diflufenzopyr, flurenol and naptalam, or an agriculturally acceptable salt or ester exposes synergy, for example, the active ingredients of the herbicide are more effective in combination with
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23/86 than when applied individually. Synergy 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. 9 Ed Lawrence. Weed Science Society of America, 2007. In certain embodiments, the compositions exhibit synergy as determined by Colby equation. Colby, SR 1967. Calculation of te synergistic and antagonistic response of herbicide combinations. Weeds 15: 20-22.
[0074] In certain embodiments of the compositions and methods described here, the compound according to Formula (I), that is, carboxylic acid, is employed. In certain embodiments, a carboxylate salt of the compound according to Formula (I) is employed. In certain embodiments, an aralkyl or alkyl ester is employed. In certain embodiments, benzyl, substituted benzyl, or C1-4-alkyl, for example, the n-butyl ester is employed. In certain embodiments, the benzyl ester is used.
[0075] In some embodiments, the compound according to Formula (I) or salt or ester thereof and the auxin transport inhibitor, or agriculturally acceptable salt or ester thereof, is formulated in a composition, mixed in a tank, applied simultaneously, or applied sequentially.
[0076] The activity of the herbicide is exposed by the compounds when they are applied directly to the plant or to the place of the plant at any stage of growth. The observed effect depends on the plant species to be controlled, the plant growth stage, the application parameters of dilution and low spray size, the particle size of solid components, the environmental conditions at the time of use, the compound specific employee, the specific adjuvants and vehicles employed, the type of soil, and so
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24/86 onwards, as well as the amount of chemical applied. These and other factors can be adjusted to promote the non-selective or selective action of the herbicide. In some embodiments, the compositions described here are applied as a post-sprouting application, pre-sprouting application, or water application to the flooded rice grain or bodies of water (eg, ponds, lakes and streams), to relatively immature undesirable vegetation for achieve maximum weed control.
[0077] In some embodiments, the compositions and methods provided here are used to control weeds in crops, including, but not limited to rice directly sown, rice sown in water, transplanted rice, cereals, wheat, barley, oats, rye , sorghum, corn / hominy, sugar cane, sunflower, rapeseed, canola, sugar beet, soy, cotton, pineapple, pasture, pasture, fallow land, lawn, orchards of trees and vines, aquatic vegetation, crops of planting, vegetables, industrial vegetation management (IVM) and easements (ROW).
[0078] In certain embodiments, the compositions and methods provided here are used to control weeds in rice. In certain modalities, rice is directly sown, sown in water, or transplanted rice.
[0079] The compositions and methods described here can be used to control undesirable vegetation in glyphosate-tolerant, 5-enolylatopyruvylshikimato-3-phosphate (EPSP) synthase inhibitor - tolerant to glufosinate, tolerant to glutamine synthetase inhibitor - tolerant to dicamba - tolerant to phenoxy auxin - tolerant to pyridyloxy auxin - tolerant to auxin - tolerant to auxin transport inhibitor - tolerant to aryloxyphenoxypropionate - tolerant to cyclohexanedione - tolerant to phenylpyrazoline - acetyl CoA carboxylase (ACCase) tolerant to inhibitor - tolerant to inhibitor imidazolinone, tolerant to the south
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25/86 phonylurea, tolerant to pyrimidinylthiobenzoate - tolerant to triazolopyrimidine - tolerant to sulfonylaminocarbonyltriazolinone - acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) tolerant to inhibitor - 4-hydroxyphenyl-pyruvate inhibitor (tolerant of the dioxigenase) phytoene desaturase - carotenoid biosynthesis, inhibitor tolerant - protoporphyrinogen oxidase (PPO), inhibitor tolerant - cellulose biosynthesis inhibitor tolerant - mitotic inhibitor tolerant - inhibitor microtubule tolerant - very long chain fatty acid tolerant inhibitor - fatty acid and lipid biosynthesis tolerant of inhibitor - tolerant of photosystem inhibitor I tolerant of photosystem inhibitor II - tolerant to triazine, and bromoxynil-tolerant-crops (such as, but not limited to, soy, cotton, canola / oilseed theft , rice, cereals, corn, sorghum, sunflower, sugar beet, sugar cane, lawn, etc. .) for example, in conjunction with glyphosate, EPSP synthase inhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, inhibitors of AColinazones, , sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD inhibitors, phytene desaturase inhibitors, carotenoid biosynthesis inhibitors, cellulose inhibitor inhibitors, cellulose inhibitor inhibitors, cellulose inhibitors, cellulose inhibitors very long chains, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil. The compositions and methods can be used to control undesirable vegetation in crops that have multiple or stacked characteristics giving tolerance to multiple chemical compositions and / or inhibitors of multiple modes of action. In some embodiments, the compound according to Formula (I) or salt or ester
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26/86 of the same and complementary herbicide or salt or ester of the same is used in combination with herbicides that are selective for the crop that is treated and that complete the spectrum of weeds controlled by these compounds at the application rate employed. In some embodiments, the compositions described here and other complementary herbicides are applied at the same time, as a combination formulation or as a tank mixture, or sequentially.
[0080] The compositions and methods can be used to control undesirable vegetation in crops that have tolerance to agronomic stress (including but not limited to drought, cold, heat, salt, water, nutrient, fertility, pH), tolerance to plague (including but not limited to insects, fungi and pathogens) and crop improvement characteristics (including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and architecture plant).
[0081] The compositions and methods provided here are used to control undesirable vegetation. Undesirable vegetation includes, but is not limited to, undesirable vegetation that occurs in rice, cereals, wheat, barley, oats, rye, sorghum, corn / hominy, cane sugar, sunflower, rapeseed, canola, sugar beet, soy, cotton, pineapple, pasture, pasture, fallow land, lawn, orchards of trees and vines, aquatic vegetation, plantation crops, vegetables, industrial vegetation management (IVM) and easements (ROW).
[0082] In some embodiments, the methods provided here are used to control undesirable vegetation in rice. In certain modalities, the undesirable vegetation is Brachiaria platyfilla (Groseb). Nash or Urochloa platyfilla (Nash) R.D. Webster (leafy signalgrass, BRAPP), Digitaria sanguinalis (L). Scop. (large crabgrass, DIGSA),
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27/86 species Echinochloa (ECHSS), Echinochloa crus-galli (L). P. Beauv. (barnyardgrass, ECHCG), Echinochloa crus-pavonis (Kunt) Schult. (gulf cockspur, ECHCV), Echinochloa colonum (L). CONNECTION (junglerice, ECHCO), Echinochloa oryzoides (Ard). Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Echinochloa fillopogon (Stapf) Koso-Pol. (barnyardgrass rice, ECHPH), Echinochloa polystachya (Kunt) Hitchc. (dragging river grass, ECHPO), Ischaemum rugosum Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L). Nees (Chinese sprangletop, LEFCH), Leptochloa fascicularis (Lam). Gray (faced sprangletop, LEFFA), Leptochloa panicoides (Presl). Hitchc. (The Amazon sprangletop, LEFPA), Oryza species (red and weed rice, ORYSS), Panicum dichotomiflorum (L). Michx. (fall panicum, PANDI), Paspalum dilatatum Poir. (dallisgrass, PASDI), Rottboellia os cochinchinensis (Frown). W.D. Clayton (itchgrass, ROOEX), Cyperus species (CYPSS), Cyperus difformis L. (smallflower flatsedge, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus would L. (flatsedge rice, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Cyperus serotinus Rottb./CBClarke (tidalmarsh flatsedge, CYPSE) , Eleocharis species (ELOSS), Fimbristylis miliacea (L). Vahl (globe fringerush, FIMMI), Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb. (Japanese Junco, SCPJU), Bolboschoenus maritimus (L). Palla or Schoenoplectus maritimus L. Lye (clubrush sea, SCPMA), Schoenoplectus mucronatus L. (rice paddy, SCPMU), Aeschynomeno species, (jointvetch, AESSS), Alternantera philoxeroides (Market). Griseb. (alligatorweed, ALRPH), Alisma plantago-aquatica L. (common waterplantain, ALSPA), Amarantus species, (pigweeds and amaranths, ACCUMULATE), Ammannia coccinea Rottb. (redstem, AMMCO), Commelina benghalensis L. (Benghal dayflower,
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VALE), Eclipta alba (L). Hassk. (American fake daisy, ECLAL), Heterantera limosa (SW). Willd./Vahl (ducksalad, HETLI), Heterantera reniformis R. & P. (roundleaf mudplantain, HETRE), Ipomoea species (morningglories, IPOSS), Ipomoea hederacea (L). Jacq. (ivyleaf morningglory, IPOHE), Lindernia dubia (L). Pennell (false bass, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (the primrose willow to the southeast, LUDLI), Ludwigia octovalvis (Jacq). Crow (longfruited willow primrose, LUDOC), Monochoria korsakowii Regel & Maack (monorail, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl except Kuht, (monorail, MOOVA), Murdannia nudiflora (L). Brenan (doveweed, MUDNU), Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladystumb, POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Rotala indica (Willd). Koehne (Indian tootcup, ROTIN), Sagittaria species, (arrowhead, SAGSS), Sesbania exaltata (Raf). Cory / Rydb. Except Colina (sesbania hemp, SEBEX), or Sfenoclea zeylanica Gaertn. (gooseweed, SPDZE).
[0083] In some embodiments, the methods provided here are used to control undesirable vegetation in cereals. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L). Beauv. (windgrass, APESV), Avena fatua L. (wild oats, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian Ryegrass, LOLMU), Phalaris Retz minor. (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria pumila (Poir). Roemer & J.A. Schultes (yellow foxtail, SETLU), Setaria viridis (L). Beauv. (green foxtail, SETVI), Amarantus retroflexus L. (redroot pigweed, AMARE), Brassica species (BRSSS), Chenopodium L. album (ançarinhas - branco, CHEAL), Cirsium arvense (L). Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed bedstraw, GALAP),
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Kochia scoparia (L). Schrad. (kochia, KCHSC), Lamium purpureum L. (purple deadnettle, LAMPU), Matricaria recutita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.). Porter (pineappleweed, MATMT), Papaver rhoeas L. (common poppy, PAPRH), Polygonum L. (wild buckwheat, POLCO) convolvulus, Salsola tragus L. (Russian thistle, SASKR), Sinapis species (SINSS), Sinapis arvensis L (wild mustard, SINAR), Stellaria means (L). Vill. (common gray-winged moray, STEME), Verônica persica Poir. (Persian Veronica, VERPE), Viola arvensis Murr. (field violet, VIOAR), or tricolor flag of Viola L. (wild violet, VIOTR).
[0084] In some modalities, the methods provided here are used to control undesirable vegetation in range and pasture, fallowland, IVM and ROW. In certain modalities, the undesirable vegetation is Ambrosia artemisiifolia L. (common snail, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct. not Lam. (noted knapweed, CENMA), Cirsium arvense (L). Scop. (Canada thistle, CIRAR), Convólvulo arvensis L. (field climbing, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola L./Torn. (prickly lettuce, LACSE), Plantago lanceolata L. (banana buckhorn, PLALA), Rumex obtusifolius L. (hardwood dock, RUMOB), Sida spinosa L. (prickly aids, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennial sowtistle, SONAR), Solidago species (solidago, SOOSS), Taraxacum officinale GH Weber except Wiggers (dandelion, TAROF), Trifolium L. reeds (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).
[0085] In some embodiments, the methods provided here are used to control the undesirable vegetation found in row crops, tree and vine crops, and perennial crops. In
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30/86 certain modalities, the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wild oats, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) R.D. Webster (grass from Surinan, BRADC), Brachiaria brizanta (Hochst. except A. Rich.) Stapf. or Urochloa brizanta (Hochst. except A. Rich.) R.D. (beard grass, BRABR), Brachiaria platyfilla (Groseb). Nash or Urochloa platyfilla (Nash) R.D. Webster (leafy signalgrass, BRAPP), Brachiaria plantaginea (Connection) Hitchc. or Urochloa plantaginea (Connection) R.D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (Southern sandbur, CENEC), Digitaria horizontalis Willd. (Jamaican crabgrass, DIGHO), Digitaria insularis (L). Mez except Ekman (sourgrass, TRCIN), Digitaria sanguinalis (L). Scop. (large crabgrass, DIGSA), Echinochloa crus-galli (L). P. Beauv. (barnyardgrass, ECHCG), Echinochloa colonum (L). Connection (junglerice, ECHCO), Eleusina indica (L). Gaertn. (goosegrass, ELEIN), Lolium multiflorum Lam. (Italian Ryegrass, LOLMU), Panicum dichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild millet, PANMI), Setaria faberi Herrm. (giant foxtaila, SETFA), Setaria viridis (L). Beauv. (green foxtail, SETVI), Sorghum halepense (L). Pers. (Johnsongrass, SORHA), Sorghum bicolor (L). Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilon teophrasti Medik. (velvetleaf, ABUT), Amarantus species (pigweeds and amaranths, ACCUMULATE), Ambrosia artemisiifolia L. (common hedge, AMBEL), Ambrosia psilostachya DC. (western raft, AMBPS), Ambrosia trifida L. (giant raft, AMBTR), Anoda cristata (L). Schlecht. (spur anoda, ANVCR), Asclepias syriaca L. (common milkweed, ASCSY), Bidens pilosa L. (hairy beggarticks, BIDPI), Borreria species (BOISS), Borreria alata (Aubl). A.D. or Spermacoce alata Aubl. (leafy buttonweed, BOILF), Sper
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31/86 macose latifolia (broadleaved bud weed, BOILF), Chenopodium album L. (ançarinhas de branco, CHEAL), Cirsium arvense (L). Scop. (Canada thistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, VALE), Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterofilla L. (wild poinsetia, EPHHL) , Euphorbia hirta L. or Chamaesyce hirta (L). Millsp. (garden spurge, EPHHI), Euphorbia dentata Michx. (toothed spurge, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L). Cronq. (hairy fleabano, ERIBO), Erigeron canadensis L. or Conyza canadensis (L). Cronq. (Canadian fleabano, ERICA), Conyza sumatrensis (Retz). E. H. Walker (high fleaban, ERIFL), Heliantus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L). Griseb. (morningglory smallflower, IAQTA), Ipomoea hederacea (L). Jacq. (ivyleaf morningglory, IPOHE), Ipomoea lacunosa L. (white morningglory, IPOLA), Lactuca serriola L./Torn. (prickly lettuce, LACSE), Portulaca oleracea L. (purslane, POROL), Richardia species (pusley, RCHSS), Sida species (aids, SIDSS), Sida spinosa L. (prickly aids, SIDSP), Sinapis arvensis L. (mustard wild, SINAR), Solanum ptychantum Dunal (oriental wild tomato, SOLPT), Tridax procumbens L. (lining buds, TRQPR), or Xantium strumarium L. (common cocklebur, XANST).
[0086] In some modalities, the methods provided here are used to control undesirable vegetation on the lawn. In certain modalities, the undesirable vegetation is Bellis perennis L. (English daisy, BELPE), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L). Scop. (large crabgrass, DIGSA), Diodia virginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (spurges, EPHSS), Glechoma hederacea L. (found ivy, GLEHE), Hydrocotyle umbellata L. (dollarweed, HYDUM), Kylinga species (kylinga, KYSS), Lamium amplexicaule L.
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32/86 (henbit, LAMAM), Murdannia nudiflora (L). Brenan (doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L. (leafy banana type, PLAMA), Plantago lanceolata L. (buckhorn / banana tree type, PLALA), Fillantus urinaria L. (chamberbitter, PYLTE), Rumex obtusifolius L. (hardwood dock, RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL), Stellaria media (L). Vill. (common chickweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Viola species (wild violet, VIOSS).
[0087] In some embodiments, the compositions and methods provided here are used to control undesirable vegetation consisting of grass, hardwood and sedge weeds. In certain embodiments, the compositions and methods provided here are used to control undesirable vegetation including Brachiaria or Urochloa, Cyperus, Digitaria, Echinochloa, Fimbristylis, Ipomoea, Leptochloa and Schoenoplectus / Bolboschoenus.
[0088] In some embodiments, the combination of compound (I) or agriculturally acceptable ester or salt thereof and chlorflurenol, diflufenzopyr, flurenol and naptalam, or agriculturally acceptable salt or ester thereof is used to control Brachiaria platyfilla (Griseb). Nash or Urochloa platyfilla (Nash) R.D. Webster (leafy signalgrass, BRAPP), Cyperus would L. (flatsedge rice, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Digitaria sanguinalis (L). Scop. (large crabgrass, DIGSA), Echinochloa crus-galli (L). Beauv. (barnyardgrass, ECHCG), Echinochloa colona (L). Connection (junglerice, ECHCO), Echinochloa oryzoides (Ard). Fritsch (early watergrass, ECHOR), Fimbristylis miliacea (L). Vahl (globe fringerush, FIMMI), Ipomoea hederacea Jacq. (ivyleaf morningglory, IPOHE), Leptochloa chinensis (L). Nees (Chinese sprangletop, LEFCH) and Schoenoplectus
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33/86 maritimus (L). Bleach or Bolboschoenus maritimus (L). Palla (sea clubrush, SCPMA).
[0089] The compounds of Formula I or agriculturally acceptable salt or ester thereof can be used to control herbicide resistant or tolerant weeds. The methods that employ the combination of a compound according to Formula I 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 biotypes to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, inhibonylaminocarbons) photosystem II (for example, phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, urea, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (for example aryloxyphenoxypropionines, cyclohexanines, cyclohexanodines, cyclohexane eg benzoic acids, phenoxycarboxylic acids, pyridine carboxylic acids, quinoline carboxylic acids), auxin transport inhibitors (eg phtalamates, semicarbazones), photosystem I inhibitors (eg bipyridyliums), 5-enolpiruvilshiktoto3- phosphate (EPSP) synthase (e.g., gl ifosate), glutamine synthetase inhibitors (eg, glufosinate, bialafos), microtubule assembly inhibitors (eg, benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (eg carbamates), inhibitors of very long chain fatty acid (VLCFA) (for example, acetamides, chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipid biosynthesis inhibitors (for example, phosphorodithioates, thiocarbamates, benzofurans, acid
Petition 870180163099, of 12/14/2018, p. 10/39
34/86 of chlorocarbons), protoporphyrinogen oxidase (PPO) inhibitors (for example Diphenyl ethers, N-phenylphthalamides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles, triazolinones), carotenoid (eg. ), phytoene desaturase (PDS) inhibitors (eg, amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxigenase (HPPD) inhibitors (eg, callistemones, isoxazoles, pyrazoles, tricetones), cellulose biosynthesis inhibitors (for example, nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes of action such as quinclorac, and unclassified herbicides such as arylaminopropionic, 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 multiple modes of action of the herbicide, and biotypes with multiple mechanisms of tolerance or resistance (for example, target site resistance or metabolic resistance).
[0090] In certain embodiments of the compositions and methods described herein, the compound according to Formula (I) or salt or ester thereof is used in combination with methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester. As for the compositions, in some embodiments, the weight ratio between the compound according to Formula (I) or its salt or ester to methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester is within a range of variation of approximately 1: 1680 to approximately 4.4: 1. In certain embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or other ester is within a range of vari
Petition 870180163099, of 12/14/2018, p. 40/102
35/86 1:63 action to approximately 1: 4. In certain embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester is within a range of approximately 1: 250 approximately 1: 4. In certain embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester is within a range of approximately 1: 125 to approximately 1: 7.8. In certain embodiments, the compositions provided herein comprise the compound according to Formula (I) or its benzyl ester and methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester. In one embodiment, the composition comprises the compound according to Formula (I) and methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester, in which the weight ratio between the compound according to Formula (I) to the methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester is approximately 1:63 to approximately 1: 7.8. In one embodiment, the composition comprises the benzyl ester of the compound according to Formula (I) and methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester, wherein the weight ratio between the benzyl ester of the compound according to with Formula (I) for methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester is approximately 1: 125 to approximately 1: 7.8. Regarding the methods, in certain modalities, the methods comprise contacting the undesirable or local vegetation of the same or applying to the soil or water to prevent the sprouting or growth of the vegetation a composition described here. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 70 grams per
Petition 870180163099, of 12/14/2018, p. 41/102
36/86 hectare (gai / ha) to approximately 3360 gai / ha based on the total sum of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 72 grams per hectare (gai / ha) to approximately 300 gai / ha based on the total sum of active ingredients in the composition. In some modalities, the methods comprise contacting the undesirable or local vegetation of the same or applying to the soil or water to prevent the sprouting or growth of the vegetation with a compound according to Formula (I) or salt or ester thereof and methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester, for example, sequentially or simultaneously. In some embodiments, methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester applied at a rate of approximately 280 gai / ha to approximately 3360 gai / ha and the compound according to Formula (I) of salt or ester thereof it is applied at a rate of approximately 2 gae / ha to approximately 300 gae / ha. In some embodiments, methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester is applied at a rate of approximately 35 gai / ha to approximately 1100 gai / ha and the compound according to Formula (I) of salt or the ester it is applied at a rate of approximately 2 gram equivalent of acid per hectare (gae / ha) to approximately 70 gae / ha. In some embodiments, methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester is applied at a rate of approximately 68.75 gai / ha to approximately 550 gai / ha and the compound according to Formula (I) of salt or the ester thereof is applied at a rate of approximately 4.38 gram-equivalents of acid per hectare (gae / ha) to approximately 35 gae / ha. In certain embodiments, the methods use the compound according to Formula (I), or its benzyl ester and methyl chlorflurenol or acid
Petition 870180163099, of 12/14/2018, p. 42/102
37/86 carboxylic or carboxylate salt of the same or another ester. In one embodiment, the methods use the compound according to Formula (I) and methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester, in which the compound according to Formula (I) is applied at a rate of approximately 4.38 gram-equivalents of acid per hectare (gae / ha) to approximately 35 gae / ha, and methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or other ester is applied at a rate of approximately 68.8 gai / ha to approximately 550 gai / ha. In one embodiment, the methods use the benzyl ester of the compound according to Formula (I) and methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester, wherein the benzyl ester of the compound according to Formula ( I) is applied at a rate of approximately 4.38 gram-equivalents of acid per hectare (gae / ha) to approximately 17.5 gae / ha, and methyl chlorflurenol or carboxylic acid or carboxylate salt of the same or another ester is applied in a rate of approximately 68.75 gai / ha to approximately 550 gai / ha. In certain embodiments, methods and compositions using the compound according to Formula (I) or its salt or ester in combination with methyl chlorflurenol or carboxylic acid or the carboxylate salt of the same or another ester are used to control ECCHG, ECHCO, CYPIR, LEFCH, IPOHE, DIGSA, ECHOR, or SCPMA.
[0091] In certain embodiments of the compositions and methods described herein, the compound according to Formula (I) or salt or ester thereof is used in combination with diflufenzopyr, diflufenzopyr sodium, or salt, carboxylic acid, carboxylate salt, or ester the same. As for the compositions, in some modalities, the weight ratio between the compound according to Formula (I) or salt or ester thereof to diflufenzopyr, diflufenzopyr sodium, salt, carboxylic acid, carboxylate salt, or ester thereof is within a variation range of approxiPetition 870180163099, from 12/14/2018, p. 43/102
38/86 only 1:18 to approximately 86: 1. In certain embodiments, the weight ratio between the compound according to Formula (I) or its salt or ester to diflufenzopyr, diflufenzopyr sodium or salt, carboxylic acid, carboxylate salt, or ester thereof is within a range of variation of 1: 8 to approximately 2: 1. In certain embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof is within a range of approximately 1: 14 to approximately 4: 1. In certain embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof is within a range of approximately 1: 7 to approximately 2: 1. In certain embodiments, the compositions provided herein comprise the compound according to Formula (I) or its benzyl and diflufenzopyr ester or salt, carboxylic acid, carboxylate salt, or ester thereof. In one embodiment, the composition comprises the compound according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof, wherein the weight ratio of the compound according to Formula (I) to diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof is approximately 1: 7 to approximately 2: 1. In one embodiment, the composition comprises the benzyl ester of the compound according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof, wherein the weight ratio between the benzyl ester of the compound of according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof is approximately 1: 4 to approximately 2: 1. In relation to the methods, in certain modalities, the methods comprise contacting the undesirable or local vegetation of the same or applying to the soil or water to prevent the sprouting
Petition 870180163099, of 12/14/2018, p. 44/102
39/86 growth or vegetation growth a composition described here. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 5 grams per hectare (gai / ha) to approximately 335 gai / ha based on the total sum of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 12 grams per hectare (gai / ha) to approximately 60 gai / ha based on the total sum of active ingredients in the composition. In some modalities, the methods comprise contacting the undesirable or local vegetation of the same or applying to the soil or water to prevent the sprouting or growth of the vegetation with a compound according to Formula (I) or salt or ester thereof and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof, for example, sequentially or simultaneously. In some embodiments, diflufenzopyr or salt or ester thereof is applied at a rate of approximately 3.5 gai / ha to approximately 35 gai / ha and the compound according to Formula (I) of salt or the ester thereof is applied at a rate of approximately 2 gae / ha to approximately 300 gae / ha. In some embodiments, diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof is applied at a rate of approximately 4 gai / ha to approximately 70 gai / ha and the compound according to Formula (I) of salt or the ester thereof is applied at a rate of approximately 2 gram equivalent of acid per hectare (gae / ha) to approximately 35 gae / ha. In some embodiments, diflufenzopyr or salt, carboxylic acid, carboxylate salt, or the ester thereof is applied at a rate of approximately 8.75 gai / ha to approximately 35 gai / ha and the compound according to Formula (I) of salt or the ester thereof is applied at a rate of approximately 4.38 gram-equivalents of acid per hectare (gae / ha) to approximately 17.5 gae / ha. In
Petition 870180163099, of 12/14/2018, p. 45/102
40/86 certain methods, the methods use the compound according to Formula (I), or its benzyl and diflufenzopyr ester or salt, carboxylic acid, carboxylate salt, or ester thereof. In one embodiment, the methods use the compound according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof, in which the compound according to Formula (I) is applied at a rate from approximately 4.38 gram-equivalents of acid per hectare (gae / ha) to approximately 17.5 gae / ha, and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or the ester thereof is applied at a rate of approximately 8 75 gai / ha to approximately 35 gai / ha. In one embodiment, the methods use the benzyl ester of the compound according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof, wherein the benzyl ester of the compound according to Formula (I) is applied at a rate of approximately 4.38 gram-equivalents of acid per hectare (gae / ha) to approximately 17.5 gae / ha, and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or the ester thereof it is applied at a rate of approximately 8.75 gai / ha to approximately 35 gai / ha. In certain embodiments, the methods and compositions use the compound according to Formula (I) or its salt or ester in combination with diflufenzopyr, diflufenzopyr sodium, or salt, carboxylic acid, carboxylate salt, or ester thereof or salt or esters of the same are used to control BRAPP, CYPRO, ECHCG, ECHCO, LEFCH, DIGSA, or IPOHE.
[0092] In certain embodiments of the compositions and methods described herein, the compound according to Formula (I) or salt or ester thereof is used in combination with diflufenzopyr, diflufenzopyr sodium, or salt, carboxylic acid, carboxylate salt, or ester the same. As for the compositions, in some modalities, the weight ratio between the compound according to Formula (I) or its salt or ester to
Petition 870180163099, of 12/14/2018, p. 46/102
41/86 diflufenzopyr, diflufenzopyr sodium, salt, carboxylic acid, carboxylate salt, or ester thereof is within a range of approximately 1:18 to approximately 86: 1. In certain embodiments, the weight ratio between the compound according to Formula (I) or its salt or ester to diflufenzopyr, diflufenzopyr sodium or salt, carboxylic acid, carboxylate salt, or ester thereof is within a range of variation of 1: 8 to approximately 2: 1. In certain embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof is within a range of approximately 1: 14 to approximately 4: 1. In certain embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof is within a range of approximately 1: 7 to approximately 2: 1. In certain embodiments, the compositions provided herein comprise the compound according to Formula (I) or its benzyl and diflufenzopyr ester or salt, carboxylic acid, carboxylate salt, or ester thereof. In one embodiment, the composition comprises the compound according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof, wherein the weight ratio of the compound according to Formula (I) to diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof is approximately 1: 7 to approximately 2: 1. In one embodiment, the composition comprises the benzyl ester of the compound according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof, wherein the weight ratio between the benzyl ester of the compound of according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof is approximately 1: 4 to approximately 2: 1. In one embodiment, the composition comprises
Petition 870180163099, of 12/14/2018, p. 47/102
42/86 of the benzyl ester of the compound according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof, wherein the weight ratio between the benzyl ester of the compound according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof is approximately 1:16 to approximately 4: 1. Regarding the methods, in certain modalities, the methods comprise contacting the undesirable or local vegetation of the same or applying to the soil or water to prevent the sprouting or growth of the vegetation a composition described here. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 5 grams per hectare (gai / ha) to approximately 335 gai / ha based on the total sum of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 12 grams per hectare (gai / ha) to approximately 60 gai / ha based on the total sum of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of approximately 12 grams per hectare (gai / ha) to approximately 102 gai / ha based on the total sum of active ingredients in the composition. In some modalities, the methods comprise contacting the undesirable or local vegetation of the same or applying to the soil or water to prevent the sprouting or growth of the vegetation with a compound according to Formula (I) or salt or ester thereof and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof, for example, sequentially or simultaneously. In some embodiments, diflufenzopyr or salt or ester thereof is applied at a rate of approximately 3.5 gai / ha to approximately 35 gai / ha and the compound according to Formula (I) of salt or the ester thereof is applied in a rate of approximately 2 gae / ha to approximately 300 gae / ha. And bad
Petition 870180163099, of 12/14/2018, p. 48/102
43/86 In some embodiments, diflufenzopyr or salt, carboxylic acid, carboxylate salt, or the ester thereof is applied at a rate of approximately 4 gai / ha to approximately 70 gai / ha and the compound according to Formula (I) of salt or its ester is applied at a rate of approximately 2 gram equivalent of acid per hectare (gae / ha) to approximately 35 gae / ha. In some embodiments, diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof is applied at a rate of approximately 8.75 gai / ha to approximately 35 gai / ha and the compound according to Formula (I) salt or its ester is applied at a rate of approximately 4.38 gram-equivalents of acid per hectare (gae / ha) to approximately 17.5 gae / ha. In some embodiments, diflufenzopyr or salt, carboxylic acid, carboxylate salt, or the ester thereof is applied at a rate of approximately 8.75 gai / ha to approximately 70 gai / ha and the compound according to Formula (I) of salt or the ester thereof is applied at a rate of approximately 4.38 gram-equivalents of acid per hectare (gae / ha) to approximately 32 gae / ha. In certain embodiments, the methods use the compound according to Formula (I), or its benzyl and diflufenzopyr ester or salt, carboxylic acid, carboxylate salt, or ester thereof. In one embodiment, the methods use the compound according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof, in which the compound according to Formula (I) is applied at a rate from approximately 4.38 gram-equivalents of acid per hectare (gae / ha) to approximately 17.5 gae / ha, and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or the ester thereof is applied at a rate of approximately 8 75 gai / ha to approximately 35 gai / ha. In one embodiment, the methods use the compound according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof, in which the compound of
Petition 870180163099, of 12/14/2018, p. 49/102
44/86 according to Formula (I) is applied at a rate of approximately 4.38 gram-equivalents of acid per hectare (gae / ha) to approximately 32 gae / ha, and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or the ester thereof is applied at a rate of approximately 8.75 gai / ha to approximately 70 gai / ha. In one embodiment, the methods use the benzyl ester of the compound according to Formula (I) and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or ester thereof, wherein the benzyl ester of the compound according to Formula (I) is applied at a rate of approximately 4.38 gram-equivalents of acid per hectare (gae / ha) to approximately 17.5 gae / ha, and diflufenzopyr or salt, carboxylic acid, carboxylate salt, or the ester thereof it is applied at a rate of approximately 8.75 gai / ha to approximately 35 gai / ha. In certain embodiments, the methods and compositions use the compound according to Formula (I) or its salt or ester in combination with diflufenzopyr, diflufenzopyr sodium, or salt, carboxylic acid, carboxylate salt, or ester thereof or salt or esters of the same are used to control BRAPP, CYPRO, ECHCG, ECHCO, LEFCH, DIGSA, or IPOHE.
[0093] In certain embodiments of the compositions and methods described herein, the compound according to Formula (I) or salt or ester thereof is used in combination with flurenol, methyl flurenol or carboxylate salt or ester thereof. As for the compositions, in some embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to flurenol or carboxylate salt or ester thereof is within a range of approximately 1: 1680 to approximately 4.4: 1. In certain embodiments, the weight ratio between the compound according to Formula (I) or its salt or ester to flurenol or its carboxylate salt or ester is within a range of 1:63 to approximately 1: 4. In certain embodiments, the compositions comprise the compound
Petition 870180163099, of 12/14/2018, p. 50/102
45/86 according to Formula (I) or its benzyl or n-butyl ester and flurenol or carboxylate salt or ester thereof. Regarding the methods, in certain modalities, the methods comprise contacting the undesirable or local vegetation of the same or applying to the soil or water to prevent the sprouting or growth of the vegetation a composition described here. In some embodiments, the composition is applied at an application rate of approximately 70 grams per hectare (gai / ha) to approximately 3360 gai / ha based on the total sum of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the active ingredient of approximately 72 grams per hectare (gai / ha) to approximately 300 gai / ha based on the total sum of active ingredients in the composition. In some modalities, the methods include contacting the undesirable or local vegetation of the same or applying to the soil or water to prevent the sprouting or growth of the vegetation with a compound according to Formula (I) or salt or ester thereof and flurenol or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, the flurenol or carboxylate salt or ester thereof is applied at a rate of approximately 280 gai / ha to approximately 3360 gai / ha and the compound according to Formula (I) of salt or the ester thereof is applied at a rate of approximately 2 gae / ha to approximately 300 gae / ha. In certain embodiments, the methods use the compound according to Formula (I) or its benzyl or n-butyl ester and flurenol or the carboxylate salt or ester thereof are used to control BRAPP, ECHCG, CYPIR, CYPRO, or FIMMI.
[0094] In certain embodiments of the compositions and methods described herein, the compound according to Formula (I) or salt or ester thereof is used in combination with naptalam or salt or carboxyl salt
Petition 870180163099, of 12/14/2018, p. 51/102
46/86 to or ester thereof. As for the compositions, in some embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to naptalam or salt or salt carboxylate or ester thereof is within a range of approximately 1: 2250 to approximately 4.2: 1. In certain embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to naptalam or salt or salt carboxylate or ester thereof is within a range of 1: 250 to approximately 1: 2. In certain embodiments, the compositions comprise the compound according to Formula (I) or its benzyl or n-butyl ester and naptalam or salt or carboxylate salt or ester thereof. Regarding the methods, in certain modalities, the methods comprise contacting the undesirable or local vegetation of the same or applying to the soil or water to prevent the sprouting or growth of the vegetation a composition described here. In some embodiments, the composition is applied at an active ingredient application rate of approximately 142 grams per hectare (gai / ha) to approximately 4,800 gai / ha based on the total sum of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the acid equivalent of approximately 145 grams per hectare (gai / ha) to approximately 1,170 gai / ha based on the total sum of active ingredients in the composition. In some modalities, the methods comprise contacting the undesirable or local vegetation of the same or applying to the soil or water to prevent the sprouting or growth of the vegetation with a compound according to Formula (I) or salt or ester thereof and naptalam or salt or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, naptalam or carboxylate or ester salt is applied at a rate of approximately 140 gai / ha to approximately 4,500 gai / ha and the compound
Petition 870180163099, of 12/14/2018, p. 52/102
47/86 according to Formula (I) of salt or the ester thereof is applied at a rate of approximately 2 gae / ha to approximately 300 gae / ha. In certain embodiments, the methods use the compound according to Formula (I) or its benzyl or n-butyl ester and naptalam or salt or the carboxylate salt or ester thereof are used to control BRAPP, CYPRO, ECHCG ECHOR or FIMMI.
[0095] In certain embodiments of the compositions and methods described herein, the compound according to Formula (I) or salt or ester thereof is used in combination with naptalam or salt or carboxylate salt or ester thereof. As for the compositions, in some embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to naptalam or salt or salt carboxylate or ester thereof is within a range of approximately 1: 2250 to approximately 4.2: 1. In certain embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to naptalam or salt or salt carboxylate or ester thereof is within a range of 1: 165 to approximately 1: 1. In certain embodiments, the weight ratio between the compound according to Formula (I) or salt or ester thereof to naptalam or salt or salt carboxylate or ester thereof is within a range of 1: 250 to approximately 1: 2. In certain embodiments, the compositions comprise the compound according to Formula (I) or its benzyl or n-butyl ester and naptalam or salt or carboxylate salt or ester thereof. Regarding the methods, in certain modalities, the methods comprise contacting the undesirable or local vegetation of the same or applying to the soil or water to prevent the sprouting or growth of the vegetation a composition described here. In some embodiments, the composition is applied at an application rate of the active ingredient of approximately 142 grams per hectare (gai / ha) to approximately 4,800 gai / ha based on the sum
Petition 870180163099, of 12/14/2018, p. 53/102
48/86 total active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the acid equivalent of approximately 145 grams per hectare (gai / ha) to approximately 1,170 gai / ha based on the total sum of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of the acid equivalent of approximately 38 grams per hectare (gai / ha) to approximately 1,352 gai / ha based on the total sum of active ingredients in the composition. In some modalities, the methods comprise contacting the undesirable or local vegetation of the same or applying to the soil or water to prevent the sprouting or growth of the vegetation with a compound according to Formula (I) or salt or ester thereof and naptalam or salt or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, naptalam or salt or carboxylate salt or ester thereof is applied at a rate of approximately 140 gai / ha to approximately 4,500 gai / ha and the compound according to Formula (I) of salt or the ester thereof it is applied at a rate of approximately 2 gae / ha to approximately 300 gae / ha. In some embodiments, naptalam or salt or carboxylate salt or ester thereof is applied at a rate of approximately 30 gai / ha to approximately 1,320 gai / ha and the compound according to Formula (I) of salt or the ester thereof it is applied at a rate of approximately 8 gae / ha to approximately 32 gae / ha. In certain embodiments, the methods use the compound according to Formula (I) or its benzyl or n-butyl ester and naptalam or salt or the carboxylate salt or ester thereof are used to control BRAPP, CYPRO, ECHCG ECHOR or FIMMI.
[0096] The components of the mixtures described here can be applied separately or as part of a multi-part herbicidal system.
Petition 870180163099, of 12/14/2018, p. 54/102
49/86 [0097] The mixtures described here can be applied together with one or more different herbicides to control a wider variety of undesirable vegetation. When used in conjunction with other herbicides, the composition can be formulated with another herbicide or herbicides, mixed in tank with another herbicide or herbicides or applied sequentially with another herbicide or herbicides. Some 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; choline salt 2,4-D, 2,4D esters and amines, 2,4-DB; 3,4-DA; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifene, acrolein, alachlor, allidochlor, alloxidim, allyl alcohol, alorac, ametridione, amethrine, amibuzine, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralide, amiprophos methyl, amitrol, anhydrol, anhydrol, anhydrol, sulfamide atrazine, azafenidin, azimsulfuron, aziprotrine, barban, BCPC, beflubutamide, benazoline, bencarbazone, benfluralin, benfuresate, methylsulfuron, bensulide, bentiocarb, sodium bentazon, benzadox, benzfend, benzofen, benzofen, benzyl, benz, benzyl bicyclopyrone, biphenox, bilanaphos, bispiribac sodium, borax, bromacila, bromobonyl, bromobutide, bromophenoxy, bromoxynil, brompirazon, butachlor, butafenacil, butamiphos, butenachlor, butidazole, butyuron, butyuron, butyuron, butyuron, butyuron, butyuron calcium, calcium cyanamide, cambendichlor, carbassulam, carbetamide, carboxazole, chlorprocarb, ca ethyl rfentrazone, CDEA, CEPC, clomethoxyfen, chlorambene, chloranocril, chlorazifop, chlorazin, clorbromuron, chlororbam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chloridazon, chlorimuron, chlorornitrophen, chloropon, chlorothexuron, chlorotoururon , ethyl cinidon, cinmethyline, cinosulfuron, cisanilide, clethodim, cliodinate, propargyl clodinafop,
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50/86 clofop, clomazone, clomeprop, cloprop, cloproxidim, clopyralide, methyl chloransulam, CMA, copper sulphate, CPMF, CPPC, credazine, cresol, cumiluron, cyanatrine, cyanazine, cyclate, cyclopyrimorate, cyclosulfamuron, cycloxidimuron, cycloxidimyclone , cyperquat, cyprazine, cyprazole, cypromide, daimuron, dalapon, dazomet, delaclor, desmedifam, desmetrine, di-alate, dicamba, diclobenyl, dichloralurea, dichlormate, dichorprop, dichlorprop-P, diclofen, diethyl, diclofen, diethyl diphenoxuron, difenzoquat, diflufenican, dimefuron, dimepiperate, dimetachlor, dimetamethrin, dimethenamide, dimethenamid-P, dimexane, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamide, dipropetrine, dipropetrine, dipropetrine, dipropetrine, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, etalfluralin, etbenzamide, etametsulfuron, etidimuron, etiolate, etobenzamide, etobenzamide, etofumesate, ethoxy sulfide, ethoxysulfide uron, ethinophene, etnipromide, etobenzanide, EXD, fenassulam, fenoprop, fenoxaprop, phenoxaprop-P-ethyl, phenoxaprop-Petila + ethyl isoxadifen, phenoxasulfone, phenteracol, fentiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flammable, flammable, flammable, flammable, flammable, flammable, flammable, flammable, flammable, flammable, flammable, flammable. florassulam, fluazifop, fluazifop-P-butyl, fluazolate, flucarbazone, flucethosulfuron, flucloralin, flufenacet, flufenican, flufenpir-ethyl, flumetsulam, flumezine, flumichlorac-pentyl, flumoxorine, fluoro, fluoro, fluoro, fluoro, fluoro, fluoro, fluoro, fluoro flupoxam, flupropacil, flupropanate, flupirsulfuron, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptila, flurtamone, flutiacet, fomesafen, foramsulfuron, phosamine, fumichlorac, furyloxifene, glufosinate, glufosinate, glufosinate, gluten ammonium halauxifene, methyl halauxifene, halosafen, methyl halosulfuron, haloxidine, methyl haloxifop, methyl haloxifop-P, hexachloroacetone, hexafluorate, hexazinone, imazametabenz, imazamox, imazapic, imazapyr, imazaquine, imazosulfuron, imazetapyr, indanofan, indazi
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51/86 flam, iodobonyl, iodomethane, iodosulfuron, sodium ethyl iodosulfuron, iofensulfuron, ioxynil, ipazin, ipfencarbazone, iprimidam, isocarbamide, isocyl, isometiozine, isonoruron, isopolinate, isopropyl, isopropyl, isopropylin, isopropalin, isopropylin , cetospiradox, lactofen, lenacil, linuron, MAA, MAMA, MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecopropP, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metamon, metamifon, metamifam , metflurazon, metabenztiazuron, metallopralin, metazol, methiobencarb, methiozoline, methuron, metometon, methoprotrin, methyl bromide, methyl isothiocyanate, methyldimron, metobenzuron, metobromuron, metolachlor, metholuron, methromon, methoxyuron, methoxyuron, methoxyuron, methoxyuron, , monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, neburon, nicosulfuron, ni pyraclofen, nitralin, nitrophen, nitrofluorphene, norflurazon, noruron, OC, orbencarb, orthodichlorobenzene, orthosulfamuron, orizaline, oxadiargyl, oxadiazon, oxapirazon, oxassulfuron, oxaziclomefone, oxificlofen, to pufluffen, pufluphen pentachlorophenol, pentanochlor, pentoxazone, perfluidone, petoxamide, fenisofam, fenmedifam, fenmedifam-ethyl, phenobenzuron, phenylmercury acetate, picloram, picolinafene, pinoxadene, piperophos, potassium arsenite, potassium azide, potassium, potassium azide, potassium, potassium azide , prodiamine, profluazole, profluralin, profoxidim, proglinazine, prohexadione-calcium, prometon, promethrin, pronamide, propachlor, propanyl, propaquizafop, propazine, profam, propisochlor, propoxycarbazone, propyrisulfuron, propaminide, prosulfanxine, prosulfanxine, prosulfurine, prosulfin , pyraclonyl, ethyl piraflufen, pyrasulfotol, pyrazogyl, pyrazolinate, ethyl pyrazosulfuron, pyrazoxifene, pyribenzoxim, pyributicarb, pyrichlor, pyri
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52/86 dafol, pyridate, pyriftalide, piriminobac, pyrimisulfan, sodium piritiobac, pyroxassulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamide, quizalofop, quizalofop-P-ethyl, rhodetanila, rufetulfine, rimsulfacon, rimsulfacur, setoxidim, siduron, simazine, simeton, symmetrine, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfalate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglicapine, swep, SIN-523, TCA, tebut , tebutiuron, tefuriltrione, tembotrione, tepraloxidim, terbacil, terbucarb, terbuclor, terbumeton, terbutilazine, terbutrin, tetrafluron, tenilchlor, thiazafluron, thiazopyr, tidiazimine, tidiazuron, tidiazuron, tidiazuron, tenciazuron, tenciazuron, tenciazone , triafamone, tri-alate, triasulfuron, triaziflam, tribenuron, methyl tribenuron, tricamba, triclopyroline choline salt, esters, amines, and salts of triclopyr, tridifan, trietazine, trifloxysulfuron, trifluralin, triflussulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron, vernolate, xylachlor and salts, the same esters and isomers.
[0098] The compositions and methods described here, can additionally be used in conjunction with glyphosate, 5-enolpyruvylshikimato-3-phosphate (EPSP) synthetase inhibitor, glufosinate, glutamine synthetase inhibitor, dicamba, phenoxy auxin, pyridyloxy auxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl CoA carboxylase inhibitor (ACCase), imidazolinone, sulfonylurea, pyrimidinylthiobenzoate, triazolpyrimidine, acetonyl acetate, sulfonyl acetate (AHAS), 4-hydroxy phenyl pyruvate dehydrogenase (HPPD) inhibitor, phytoene desaturase inhibitor, carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase (PPO) inhibitor, cellulose biosynthesis inhibitor, mitosis inhibitor, microtubule inhibitor, microtubule inhibitor chain fatty too
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53/86 long, fatty acid and lipid biosynthesis inhibitor, photosystem I inhibitor, photosystem II inhibitor, triazines, and bromoxynil in glyphosate tolerant, tolerant to EPSP synthetase inhibitor, glufosinate tolerant, tolerant to glutamine inhibitor synthase, tolerant to dicamba, tolerant to phenoxy auxin, tolerant to pyridyloxy auxin, tolerant to auxin, tolerant to auxin transport inhibitor, tolerant to aryloxyphenoxypropionate, tolerant to cyclohexanedione, tolerant to phenylpyrazoline, tolerant to ACCase, tolerant to imidazolinone tolerant to sulfonylurea, tolerant to pyrimidinylthiobenzoate, tolerant to triazolopyrimidine, tolerant to sulfonylaminocarbonyltriazolinone, tolerant to ALS or AHAS, tolerant to HPPD, tolerant to phytene inhibitor desaturase, tolerant to carotide inhibitor, PPT tolerant cellulose biosynthesis, tolerant to mitosis inhibitor, tolerant microtubule inhibitor, tolerant to very long chain fatty acid inhibitor, tolerant to fatty acid and lipid biosynthesis inhibitor, tolerant to photosystem I inhibitor, tolerant to photosystem II inhibitor, tolerant to triazine, tolerant to bromoxynil, and crops that have multiple or stacked characteristics giving tolerance to multiple chemical compositions and / or multiple modes of action via single and / or multiple resistance mechanisms. In some embodiments, the compound according to Formula (I) or salt or ester thereof and complementary herbicide or salt or ester thereof is used in combination with herbicides that are selective for the crop that is treated and that complete the spectrum. weeds controlled by these compounds at the application rate employed. In some embodiments, the compositions described here and other complementary herbicides are applied at the same time, as a combination formulation or as a tank mixture.
[0099] In some modalities, the compositions described here
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54/86 are used in combination with one or more herbicide protectors, such as AD-67 (MON 4660), benoxacor, bentiocarb, brassinolid, cloquintocet (mexil), ciometrinyl, daimuron, dichlormid, diciclonon, dimepiperate, disulfoton, fenclorazol ethyl, fenclorim, flurazol, fluxofenim, furilazol, protein harpina, isoxadifen-ethyl, jiecaowan, jiecaóxi, mefenpir diethyl, mefenato, naphthalic anhydride (NA), oxabetrinil, R29148 and acid amides V-phenyl-sulfonylbenz to improve its. In some embodiments, protectors are used in rice, cereal, corn, or corn settings. In some embodiments, the protector is cloquintocet or an ester or salt thereof. In certain embodiments, cloquintocet is used to contract dangerous effects of the compositions on rice and cereals. In some modalities, the protector is cloquintocet (mexila).
[00100] 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 acetic acids, benzyladenine , 4-hydroxyphenothyl alcohol, kinatin, zeatin, endotal, etefon, pentachlorophenol, tidiazuron, tribufos, aviglycine, etefon, maleic hydrazide, gibberellins, gibberellic acid, abscisic acid, ancimidol, phosamine, glyphosine, jasmine, jasmine , 2,3,5-triiodobenzoic acid, morphactins, dichlorflurenol, flurprimidol, mefluidide, paclobutrazol, tetciclacis, uniconazole, brassinolid, ethyl brassinolid, cycloheximide, ethylene, metasulfocarb, prohexadione, triapentenol and triapentenol.
[00101] In some modalities, plant growth regulators are used in one or more crops or crops, such as rice, cereal, corn, corn, leafy crops, rape / canola berry, lawn, pineapple, cane -sugar, sunflower, pasture, pasture, fallow land, lawn, tree orchards and saw
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55/86 deiras, plantation crops, vegetables, and non-harvest (ornamental) settings. In some embodiments, the plant growth regulator is mixed with the compound according to Formula (I), or mixed with the compound according to Formula (I) and auxin transport inhibitors to cause a preferentially beneficial effect on plants.
[00102] In some embodiments, the compositions provided here additionally 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 selective weed control compositions in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients. Such mixtures can be designed for application directly to weeds or their place or they can be concentrated or formulations that are usually diluted with additional vehicles and adjuvants before application. They can be solids, such as, for example, powder, granules, water-dispersible granules, or wettable powder, or liquids, such as, for example, concentrated emulsifiable solution, solutions, emulsions or suspensions. They can also be supplied as a cake mix or tank mix.
[00103] Suitable agricultural adjuvants and vehicles include, but are not limited to, cereal oil concentrates; nonylphenol ethoxylate; benzylcocoalkylimethyl quaternary ammonium salt; mixture of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9-C11 alkyl polyglycoside; phosphate alcohol ethoxylate; natural primary alcohol (C12-C16) ethoxylate; the di-sec-butylphenol EO-PO block copolymer; polysiloxane methyl flap; nonylphenol ethoxylate + urea ammonium nitrate; seed oil
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56/86 emulsified methylated; tridecyl alcohol ethoxylate (synthetic) (8EO); tallow amine ethoxylate (15 EO); PEG (400) dioleate-99.
[00104] Liquid vehicles that can be used include water and organic solvents. Organic solvents include, but are not limited to, petroleum or hydrocarbon fractions such as mineral oil, aromatic solvents, paraffinic oils, and so on; vegetable oils such as soybean oil, rapeseed oil, olive oil, linseed oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, palm oil peanuts, safflower oil, sesame oil, tung oil and so on; esters of the above vegetable oils; esters of mono-alcohols or dihydric, trihydric, or other lower polyalcohol (containing 4-6 hydroxy), such as 2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, adipate di-butyl, di-octyl phthalate and so on; esters of mono-, di- and polycarboxylic acids and so on. Specific organic solvents include, but are not limited to, toluene, xylene, petroleum naphtha, cereal oil, acetone, methyl ethyl ketone, cyclohexanone, trichlorethylene, perchlorethylene, ethyl acetate, amyl acetate, butyl acetate, ether propylene glycol monomethyl and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerin, Nmethyl-2-pyrrolidinone, N, N-dimethyl alkylamides, sulfoxide dimethyl, liquid fertilizers and so on. In certain modalities, water is the vehicle for diluting concentrates.
[00105] Suitable solid vehicles include, but are not limited to, talc, pyrophyllite clay, silica, atapulgite clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, mistletoe, calcium carbonate, bentonite clay, Fuller earth , cotton seed husks, wheat flour, soy flour, pumice stone, wood flour, fariPetição 870180163099, from 12/14/2018, p. 62/102
57/86 nutshell, lignin, cellulose, and so on.
[00106] In some embodiments, the compositions described here additionally comprise one or more surfactants. In some embodiments, such surfactants are used in both solid and liquid compositions, and in certain embodiments, those designed to be diluted with the vehicle prior to application. Surfactants can be anionic, cationic or non-ionic in character and can be used as emulsifying agents, wetting agents, or agents for other purposes. Surfactants that can also be used in the present formulations are described, among other things, in McCutcheon's Detergents and Emulsifiers Annual MC Publishing Corp., Ridgewood, New Jersey, 1998 and Encyclopedia of Surfactants, Vol. I-III, Chemical Publishing Co. , New York, 1980-81. Surfactants include, but are not limited to, alkyl sulfate salts, such as diethylammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as C18 nonylphenol ethoxylate; alcohol alkylene oxide addition products, such as alcohol tridecyl ethoxylate-Cw; soaps, such as sodium stearate; alkylnaphthalene sulfonate salts, such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di (2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as trimethylammonium lauryl chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; dialkyl mono phosphate salts and esters; vegetable or seed oils such as soybean oil, rapeseed / canola oil, olive oil, linseed oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, olive oil palm oil, peanut oil, safflower oil, palm oil
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58/86 sesame, tung oil and so on; and esters of the above vegetable oils, and in certain embodiments, methyl esters.
[00107] In some embodiments, these materials, such as vegetable or seed oils and their esters, can be used interchangeably as an agricultural adjuvant, as a liquid vehicle or as a surface active agent.
[00108] Other exemplary additives for use in the compositions provided here include, but are not limited to compatibilizing agents, antifoaming agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorizers, spreading agents, penetration aids, agents adhesion agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and so on. The compositions can also contain other compatible components, for example, other herbicides, plant growth regulators, fungicides, insecticides, and so on and can be formulated with liquid fertilizers or particulate solid fertilizer vehicles, such as ammonium nitrate, urea and so on.
[00109] In some embodiments, the concentration of active ingredients in the compositions described here is approximately 0.0005 to 98 weight percent. In some embodiments, the concentration is approximately 0.0006 to 90 weight percent. In compositions designed to be used as concentrates, the active ingredients, in certain embodiments, are present in a concentration of approximately 0.1 to 98 percent by weight, and in a certain embodiment approximately 0.5 to 90 percent by weight. Such compositions are, in certain embodiments, diluted with an inert carrier, such as water, prior to application. The diluted compositions normally applied to weeds or to the location of weeds contain, in certain embodiments, from approximately 0.0006 to
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3.0 weight percent of active ingredient in certain embodiments contains approximately 0.01 to 1.0 weight percent.
[00110] The present compositions can be applied to weeds or their location by the use of conventional grounded or overhead sprinklers, sprayers, and granule applicators, by adding irrigation or rice-growing water with husk, and by other means conventional known to those skilled in the art.
[00111] The modalities described and the following examples exist for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses, or compositions in relation to combinations described here will be evident to a person of normal skill in the technique without departing from the spirit and scope of the claimed subject matter.
Examples [00112] The results in Examples I and II are the results of greenhouse tests.
Example I. Post-sprouting Foliage-Herbicidal Mixtures Applied to Control Herbs in Directly Seeded Rice.
[00113] The seeds or sowing of the desired test plant species were planted in a soil matrix prepared by mixing a loam or sandy loam soil (for example, 28.6 percent mud, 18.8 percent clay, and 52.6 percent sand, with a pH of approximately 5.8 and an organic matter content of approximately 1.8 percent) and limestone sand in a ratio of 80 to 20. The soil matrix was contained in pots plastics with a volume of 1 quarter and a surface area of 83.6 square centimeters (cm ² ). 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 to 22 days in a greenhouse with an approximate photoperiod of 14 hours that was maintained
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60/86 at approximately 29 ° C during the day and 26 ° C at night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg and iron chelate) were applied to the irrigation solution as needed and water was added on a regular basis. Supplementary lighting was provided with over 1000 watt metal halide lamps as needed. The plants were used in testing when they reached the first quarter of the stage of true foliage.
[00114] 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) one formulated as a SC (concentrated suspension), and several herbicidal components alone and in combination.
[00115] Compound A forms were applied on an acid equivalent basis.
[00116] The forms of compound A (compound according to Formula I) tested include:
Acid Compound
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N 11,
Benzyl Ester Compound [00117] Other herbicidal components have been applied on an active ingredient basis and include the auxin transport inhibitor (ATI), chlorflurenol herbicides (technical material), methyl chlorflurenol (technical material), diflufenzopir (technical material) , diflufenzopyr sodium (technical material), methyl flurenol (technical material) and naptalam (technical material).
[00118] The treatment requirements were calculated based on the rates that are 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.
[00119] For treatments comprised of formulated compounds, the measured amounts of compounds can be placed individually in 25 ml glass bottles and diluted in a volume of 1.25% (v / v) Agri-Dex® concentrated cereal oil for get 12X stock solutions. If a test compound does not readily dissolve, the mixture can be heated and / or subjected to ultrasound. 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 a 1.25% (v / v) aqueous mixture of concentrated cereal oil so that the final spray solutions contain 1.25% + / 0.05 (v / v) of concentrated cereal oil.
[00120] For treatments comprising technical compounds
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62/86 formulated, the weighed quantities can be placed individually in 25 ml glass vials and dissolved in a volume of 97: 3 v / v acetone / DMSO to obtain 12X stock solutions. If a test compound does not readily dissolve, the mixture can be heated and / or subjected to ultrasound. 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 a 1.5% (v / v) aqueous mixture in concentrated cereal oil so that the final spray solutions contain 1.25% (v / v) of the concentrated cereal oil. When technical materials are used, concentrated stock solutions can be added to spray solutions so that the final acetone and DMSO concentrations of the application solutions are 16.2% and 0.5%, respectively.
[00121] For treatments comprised of formulated and technical compounds, the heavy quantities of the technical materials were placed individually in 25 mL glass bottles and dissolved in a volume of 97: 3 v / v acetone / DMSO to obtain 12X stock solutions, and the measured quantities of the formulated compounds were placed individually in 25 ml glass vials and diluted in a volume of 1.5% (v / v) in concentrated cereal oil or water to obtain 12X stock solutions. If a test compound did not readily dissolve, the mixture was heated and / or subjected to ultrasound. Application solutions were 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% (v / v) aqueous mixture of concentrated cereal oil so that the final spray solutions contained 1.25% (v / v) of the concentrated cereal oil. When necessary, additional water and / or 97: 3 v / v acetone / DMSO was added
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63/86 to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared were 8.1% and 0.25%, respectively.
[00122] All stock solutions and application solutions were visually inspected for compound compatibility before application. The spray solutions were applied to the plant material with a Mandel trail sprayer equipped with an 8002E nozzle calibrated to release 187 L / ha over an application area of 0.503 m ² at a spray height of 46 to 50 cm above the height average plant canopy. The control plants were sprayed in the same way with a blank solution with only solvent.
[00123] The treated plants and the control plants were placed in a greenhouse as described above and irrigated by sub-irrigation to prevent washing of the test compounds. After approximately 3 weeks, the condition of the test plants compared to that of untreated plants was determined visually and marked on a scale of 0 to 100 percent where 0 corresponds to no damage or no growth inhibition and 100 equates to complete extermination .
[00124] Colby's equation was used to determine the expected effects of the herbicide on the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15: 20-22.).
[00125] 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)
A = the observed effectiveness of active ingredient A at the same concentration as used in the mixture.
B = the observed effectiveness of active ingredient B at the same concentration as used in the mixture.
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64/86 [00126] The tested compounds, the application rates employed, the species of plants tested, and the results are given in Tables 1 to 6.
Table 1.
[00127] Synergistic Activity of Acid Compound applied to Leaves and Herbicidal Compositions of Methyl Chlorflurenol Ester in the Control of Common Weeds for Rice Growing Systems.
Acid Compound Methyl chlorflurenol Visual herb control (%) - 20DAA ECHCG gae / ha gai / ha Note Exp 4.38 0 60 - 8.75 0 80 - 0 275 0 - 4.38 275 99 60 8.75 275 95 80
CompoundThe Acid Methyl chlorflurenol Visual herb control (%) - 20 DAA ECHCO CYPIR gae / ha gai / ha Note Exp Note Exp 4.38 0 40 - 30 - 0 68.75 0 - 0 - 0 137.5 0 - 0 - 0 275 0 - 0 - 4.38 68.75 90 40 60 30 4.38 137.5 90 40 60 30 4.38 275 90 40 99 30
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Acid Compound ChlorflurenolMethyl Visual herb control (%) - 20 DAA LEFCH IPOHE gae / ha gai / ha Note Exp Note Exp 4.38 0 0 - 20 - 8.75 0 30 - 20 - 17.5 0 30 - 50 - 0 275 10 - 55 - 4.38 275 55 10 85 64 8.75 275 50 37 80 64 17.5 275 50 37 80 78
Table 2.
[00128] Synergistic activity of Herbicidal Compositions of Methyl Chlorflurenol and Compound A Benzyl Ester Applied for Control of Foliar Weeds Common to Rice Cultivation Systems.
Benzyl Ester of Compound A Methyl chlorflurenol Visual herb control (%) - 20DAA DIGSA gae / ha gai / ha Note Exp 4.38 0 40 - 8.75 0 40 - 0 68.75 0 - 0 137.5 0 - 0 275 0 - 4.38 68.75 25 40 8.75 68.75 60 40 4.38 137.5 60 40 8.75 137.5 60 40 4.38 275 40 40 8.75 275 85 40
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Benzyl Ester of Compound A ChlorflurenolMethyl Visual herb control (%) - 20 DAA ECHCG CYPIR gae / ha gai / ha Note Exp Note Exp 4.38 0 60 - 70 - 0 68.75 0 - 0 - 0 137.5 0 - 0 - 0 275 0 - 0 - 4.38 68.75 80 60 95 70 4.38 137.5 90 60 80 70 4.38 275 85 60 100 70
Benzyl ester ofCompound A ChlorflurenolMethyl Visual herb control (%) - 20 DAA ECHCO IPOHE gae / ha gai / ha Note Exp Note Exp 4.38 0 60 - 10 - 8.75 0 80 - 15 - 0 137.5 0 - 50 - 0 275 0 - 55 - 4.38 137.5 80 60 75 55 8.75 137.5 95 80 70 58 4.38 275 85 60 85 60 8.75 275 99 80 85 62
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Benzyl ester ofCompound A ChlorflurenolMethyl Visual herb control (%) - 20DAA LEFCH gae / ha gai / ha Note Exp 4.38 0 15 - 8.75 0 30 - 0 68.75 0 - 0 137.5 10 - 0 275 10 - 4.38 68.75 50 15 8.75 68.75 55 30 4.38 137.5 30 24 8.75 137.5 55 37 4.38 275 75 24 8.75 275 45 37
Table 3.
[00129] Synergistic activity of Foliar Acid Compound and Diflufenzopyr herbicidal compositions for weeds control common to rice cultivation systems.
Acid Compound Diflufenzopyr Visual herb control (%) - 21DAA BRAPP gae / ha gai / ha Note Exp 8.75 0 60 - 0 8.75 0 - 0 17.5 40 - 0 35 80 - 8.75 8.75 95 60 8.75 17.5 90 76 8.75 35 95 92
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Acid Compound Diflufenzopyr Visual herb control (%) - 21 DAA ECHCO gae / ha gai / ha Note Exp 4.38 0 60 - 0 8.75 30 - 0 17.5 30 - 0 35 40 - 4.38 8.75 95 72 4.38 17.5 95 72 4.38 35 95 76
Acid Compound Diflufenzopyr Visual herb control (%) - 21 DAA LEFCH gae / ha gai / ha Note Exp 8.75 0 30 - 17.5 0 30 - 0 8.75 0 - 0 17.5 10 - 8.75 8.75 15 30 17.5 8.75 50 30 8.75 17.5 50 37 17.5 17.5 65 37
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Table 4.
[00130] Synergistic activity of Compound A-applied benzyl ester and Diflufenzopir herbicidal compositions for weed control common to rice cultivation systems.
Benzyl Ester of Compound A Diflufenzopyr Visual herb control (%) - 21DAA BRAPP gae / ha gai / ha Note Exp 4.38 0 70 - 8.75 0 75 - 17.5 0 95 - 0 8.75 0 - 4.38 8.75 95 70 8.75 8.75 95 75 17.5 8.75 95 95
Benzyl ester ofCompound A Diflufenzopyr Visual herb control (%) - 21 DAA DIGSA gae / ha gai / ha Note Exp 17.5 0 30 - 0 17.5 10 - 0 35 20 - 17.5 17.5 80 37 17.5 35 80 44
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Benzyl Ester of Compound A Diflufenzopyr Visual herb control (%) - 21 DAA LEFCH IPOHE gae / ha gai / ha Note Exp Note Exp 4.38 0 15 - 10 - 8.75 0 40 - 10 - 17.5 0 50 - 25 - 0 8.75 0 - 75 - 0 17.5 10 - 70 - 4.38 8.75 15 15 85 78 8.75 8.75 50 40 85 78 17.5 8.75 65 50 90 81 4.38 17.5 50 24 85 73 8.75 17.5 55 46 85 73 17.5 17.5 60 55 85 78
Table 5.
[00131] Synergistic activity of methyl Flurenol and Compound A benzyl ester herbicidal compositions applied to control common leaf weeds in rice cultivation systems.
Benzyl ester ofCompound A Flurenolmethyl Visual herb control (%) - 22 DAA BRAPP CYPIR gae / ha gai / ha Note Exp Note Exp 8 0 35 - 30 - 0 68.75 0 - 0 - 0 137.5 0 - 0 - 0 275 30 - 60 - 8 68.75 70 35 65 30 8 137.5 80 35 75 30 8 275 75 55 65 72
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Table 6.
[00132] Synergistic activity of Compound-applied benzyl ester Ester and Naptalam herbicidal compositions for control of common weeds in rice cultivation systems.
Benzyl ester ofCompound A Naptalam Visual herb control (%) - 22 DAA BRAPP gae / ha gai / ha Note Exp 8 0 35 - 16 0 80 - 0 30 0 - 0 60 0 - 0 120 0 - 8 30 75 35 16 30 80 80 8 60 70 35 16 60 90 80 8 120 80 35 16 120 85 80
Benzyl Ester of Compound A Naptalam Visual herb control (%) - 22 DAA LEFCH gae / ha gai / ha Note Exp 32 0 40 - 0 60 15 - 0 120 15 - 32 60 60 49 32 120 60 49
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Benzyl ester ofCompound A Naptalam Visual herb control (%) - 22DAA IPOHE gae / ha gai / ha Note Exp 8 0 0 - 16 0 25 - 32 0 50 - 0 60 15 - 0 120 15 - 8 60 25 15 16 60 45 36 32 60 60 58 8 120 40 15 16 120 25 36 32 120 70 58
BRAPP Brachiaria platyphilla (Griseb) .Nash CYPIR Cyperus would L.
DIGSA Digitaria sanguinalis (L). Scop.
ECHCG Echinochloa crusgalli (L). Beauv.
ECHCO Echinochloa colona (L). Link
IPOHE Ipomoea hederacea Jacq.
LEFCH Leptochloa chinensis (L). Nees signal grass, broad flat spargium leaf, crab grass rice, large barn yard grass overgrown rice in the morning, sprangle top ivy leaf, Chinese gae / ha = equivalent grams of acid per hectare gai / ha = grams of active ingredient per hectare
Obs = observed value
Exp = expected value as calculated by the Colby equation
DAA = days after application
Example II. Evaluation of Herbicide Mixtures Applied in Weed Control Water in Rice with Transplanted Rice Husk [00133] The weed seeds or nutlets of the desired test plant species were planted in the muddy soil (mud) prepared by mixing a torn, not sterilized the mineral soil (sludge
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73/86 of 50.5 percent, clay of 25.5 percent, and sand of 24 percent, with a pH of approximately 7.6 and an organic matter content of approximately 2.9 percent) and water in a 1: 1 volumetric ratio. The prepared sludge was dispensed in 365 ml aliquots in 497.6 grams. Unperforated plastic pots with a surface area of 86.59 square centimeters (cm ² ) starting from a 3 cm (cm) headspace in each pot. The sludge was allowed to dry overnight before planting or transplanting. The rice seeds were planted in the Sol Gro MetroMix® 306 planting mix, which typically has a pH of 6.0 to 6.8 and an organic matter content of approximately 30 percent, in plastic outlet trays. Seedling plants in the second or third stage of the growth leaf were transplanted in 840 mL of the mud contained in 995 grams. Unperforated plastic pots with a surface area of 86.59 cm ² 4 days before herbicide application. The paddy rice was created by filling the headspace 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 to 22 days in a greenhouse with a photoperiod of approximately 14h which was maintained at approximately 29 ° C during the day and 26 ° C at night. Nutrients were added as Osmocote® (19: 6: 12, N: P: K + minor nutrients) in 2 g per 497.6 grams per pot and 4 g per 995 grams 960 mL per pot. Water was added on a regular basis to keep the rice paddy flooding, and the supplementary lighting was over 1000 watt metal halide lamps supplied as needed. The plants were used in the test when they reached the second or third stage of true foliage.
[00134] The treatments consisted of the acid or esters of the acid
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4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) pyridine-2-carboxylic (compound A) each formulated as a SC and various herbicidal components alone and in combination . Compound A forms were applied on an equivalent acid base.
[00135] The forms of compound A (the compound according to Formula I) tested include:
Compound A 'acid
Benzyl ester of Compound A [00136] Other herbicidal components have been applied on an active ingredient basis and include auxin transport inhibitor (ATI) methyl chlorflurenol herbicides (technical material), chlorflurenol (technical material), diflufenzopir (technical material ), dilfufenzopyr sodium (technical material), methyl flurenol (technical material) and naptalam (technical material).
[00137] The treatment requirements for each compound or component of the herbicide were calculated based on the rates that are tested
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75/86, the concentration of active ingredient or acid equivalent in the formulation, an application volume of 2 mL per component per pot, and an application area of 86.59 cm ² per pot.
[00138] For formulated compounds, a measured quantity was placed in an individual glass bottle of 100 or 200 mL and was dissolved in a volume of 1.25% (v / v) Agri-Dex® in concentrated cereal oil to obtain application solutions. If the test compound does not readily dissolve, the mixture is heated and / or subjected to ultrasound.
[00139] For technical grade compounds, a heavy quantity was placed in an individual 100 or 200 mL glass bottle and was dissolved in a volume of acetone to obtain concentrated stock solutions. If the test compound did not readily dissolve, the mixture was heated and / or subjected to ultrasound. The concentrated stock solutions obtained were diluted with an equivalent volume of an aqueous mixture containing 2.5% (v / v) in concentrated cereal oil so that the final application solutions contained 1.25% (v / v) cereal oil focused.
[00140] The applications were made by injecting with a pipetter the appropriate amounts of the application solutions, individually and sequentially, in the aqueous layer of the paddy rice. The control plants were treated in the same way with a blank solution composed only of solvent. The applications were made so that all the treated plant material received the same concentrations of acetone and concentrated cereal oil.
[00141] The treated plants and the control plants were placed in a greenhouse as described above and the water was added in quantity to maintain a flood of paddy rice. After approximately 3 weeks the condition of the test plants compared to that of the untreated plants was determined vi
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76/86 and is marked on a scale of 0 to 100 percent where 0 does not correspond to any damage or inhibition of growth and 100 is equivalent to complete extermination.
[00142] Colby's equation was used to determine the herbicide effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15: 20-22.).
[00143] 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)
A = the observed effectiveness of active ingredient A at the same concentration as used in the mixture.
B = the observed effectiveness of active ingredient B at the same concentration as used in the mixture.
[00144] Some compounds tested, rates of application employed, plant species tested, and results are given in Tables 7 to 13.
Table 7.
[00145] Synergistic Activity of Acid Compound Water Applications and Methyl Chlorflurenol Compositions for Weed Control Common to Rice Cultivation Systems.
Compound AAcid Methyl chlorflurenol Visual herb control (%) - 20DAA ECHCG gae / ha gai / ha Note Exp 17.5 0 50 - 35 0 95 - 0 275 15 - 0 550 20 - 17.5 275 100 58 35 275 100 96
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Compound AAcid Methyl chlorflurenol Visual herb control (%) - 20DAA ECHCG gae / ha gai / ha Note Exp 17.5 550 100 60 35 550 100 96
Compound AAcid ChlorflurenolMethyl Visual herb control (%) - 20 DAA ECHOR LEFCH SCPMA gae / ha gai / ha Note Exp Note Exp Note Exp 8.75 0 10 - 20 - 0 - 17.5 0 15 - 0 - 0 - 35 0 25 - 30 - 30 - 0 550 10 - 0 - 80 - 8.75 550 60 19 40 20 100 80 17.5 550 50 24 40 0 100 80 35 550 70 33 30 30 100 86
Table 8.
[00146] Synergistic Activity of Water Applications of Herbicidal Compositions of Methyl Chlorflurenol and Compound A Benzyl Ester for Weed Control Common to Rice Cultivation Systems.
Benzyl Esterrank A ChlorflurenolMethyl Visual herb control (%) - 20 DAA ECHCG gae / ha gai / ha Note Exp 4.38 0 40 - 0 275 15 - 0 550 20 -
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Benzyl Esterrank A ChlorflurenolMethyl Visual herb control (%) - 20 DAA ECHCG 4.38 275 100 49 4.38 550 99 52
Benzyl ester ofCompound A ChlorflurenolMethyl Visual herb control (%) - 20DAA ECHOR gae / ha gai / ha Note Exp 4.38 0 10 - 8.75 0 15 - 0 275 20 - 0 550 10 - 4.38 275 80 28 8.75 275 60 32 4.38 550 55 19 8.75 550 80 24
Benzyl ester ofCompound A ChlorflurenolMethyl Visual herb control (%) - 20DAA LEFCH gae / ha gai / ha Note Exp 4.38 0 0 - 8.75 0 20 - 17.5 0 30 - 0 275 0 - 0 550 0 - 4.38 275 30 0 8.75 275 30 20
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Benzyl ester ofCompound A ChlorflurenolMethyl Visual herb control (%) - 20DAA LEFCH gae / ha gai / ha Note Exp 17.5 275 50 30 4.38 550 100 0 8.75 550 90 20 17.5 550 95 30
Benzyl Ester of Compound A Methyl chlorflurenol Visual herb control (%) - 20 DAA SCPMA gae / ha gai / ha Note Exp 4.38 0 0 - 8.75 0 0 - 17.5 0 0 - 0 275 75 - 4.38 275 95 75 8.75 275 100 75 17.5 275 95 75
Table 9.
[00147] Synergistic Activity of Acid Compound Water Applications and Chlorflurenol Herbicide Compositions for Weed Control Common to Rice Growing Systems.
Acid Compound Chlorflurenol Visual herb control (%) - 22 DAA ECHOR gae / ha gai / ha Note Exp 8.75 0 0 - 17.5 0 20 - 35 0 20 -
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Acid Compound Chlorflurenol Visual herb control (%) - 22 DAA ECHOR gae / ha gai / ha Note Exp 0 550 30 - 8.75 550 40 30 17.5 550 40 44 35 550 70 44
Acid Compound Chlorflurenol Visual herb control (%) - 22 DAA ECHCG SCPMA gae / ha gai / ha Note Exp Note Exp 8.75 0 0 - 0 - 17.5 0 15 - 0 - 35 0 15 - 0 - 0 275 10 - 45 - 8.75 275 20 10 50 45 17.5 275 15 24 70 45 35 275 40 24 50 45
Table 10.
[00148] Synergistic Activity of Compound A Benzyl Ester Water Applications and Chlorflurenol Herbicide Compositions in Weed Control in a Rice Growing System.
Benzyl Ester of Compound A Chlorflurenol Visual herb control (%) - 22 DAA ECHCG gae / ha gai / ha Note Exp 4.38 0 10 - 8.75 0 25 -
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Benzyl Ester of Compound A Chlorflurenol Visual herb control (%) - 22 DAA ECHCG gae / ha gai / ha Note Exp 17.5 0 60 - 0 275 10 - 4.38 275 40 19 8.75 275 35 33 17.5 275 85 64
Benzyl ester ofCompound A Chlorflurenol Visual herb control(%) - 22 DAA SCPMA gae / ha gai / ha Note Exp 8.75 0 0 - 17.5 0 0 - 0 275 45 - 0 550 60 - 8.75 275 60 45 17.5 275 60 45 8.75 550 50 60 17.5 550 80 60
Table 11.
[00149] Synergistic Activity of Compound A Benzyl Ester Water Applications and Sodium Diflufenzopyr Herbicide Compositions in Weed Control in a Rice Growing System.
Benzyl Ester of Compound A Diflufenzopir sodium Visual herb control (%) - 19 DAA ECHCG CYPRO gae / ha gai / ha Note Exp Note Exp 8 0 30 - 50 - 16 0 20 - 85 -
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Benzyl Ester of Compound A Diflufenzopir sodium Visual herb control (%) - 19 DAA ECHCG CYPRO gae / ha gai / ha Note Exp Note Exp 32 0 40 - 90 - 0 17.5 20 - 0 - 0 35 50 - 0 - 0 70 20 - 10 - 8 17.5 50 44 70 50 16 17.5 95 36 85 85 32 17.5 99 52 100 90 8 35 50 65 100 50 16 35 80 60 100 85 32 35 70 70 100 90 8 70 75 44 85 55 16 70 90 36 80 87 32 70 99 52 100 91
Benzyl ester ofCompound A Diflufenzopir sodium Visual herb control (%) - 19DAA FIMMI gae / ha gai / ha Note Exp 16 0 0 - 0 17.5 50 - 0 35 55 - 0 70 60 - 16 17.5 75 50 16 35 75 55 16 70 75 60
Table 12.
[00150] Synergistic Activity of Compound A Benzyl Ester Water Applications and Compositions of Flurenol-methyl Ester HerbiPetição 870180163099, of 12/14/2018, p. 88/102
83/86 cidal in Weed Control in a Rice Growing System.
Benzyl Ester of Compound A Flurenolmethyl Visual herb control (%) - 19 DAA ECHCG FIMMI gae / ha gai / ha Note Exp Note Exp 8 0 30 - 0 - 16 0 20 - 0 - 32 0 40 - 85 - 0 68.75 0 - 0 - 0 137.5 0 - 0 - 0 275 0 - 20 - 8 68.75 35 30 0 0 16 68.75 20 20 20 0 32 68.75 100 40 90 85 8 137.5 30 30 10 0 16 137.5 20 20 20 0 32 137.5 80 40 100 85 8 275 95 30 35 20 16 275 85 20 85 20 32 275 100 40 100 88
Benzyl ester ofCompound A Flurenolmethyl Visual herb control (%) - 19DAA CYPRO gae / ha gai / ha Note Exp 8 0 50 - 16 0 85 - 32 0 90 - 0 68.75 0 - 0 137.5 0 - 8 68.75 85 50
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Benzyl ester ofCompound A Flurenolmethyl Visual herb control (%) - 19DAA CYPRO gae / ha gai / ha Note Exp 16 68.75 80 85 32 68.75 100 90 8 137.5 85 50 16 137.5 100 85 32 137.5 100 90
Table 13.
[00151] Synergistic Activity of Compound A Benzyl Ester Water Applications and Naptalam Herbicide Compositions in Weed Control in a Rice Growing System.
Benzyl ester ofCompound A Naptalam Visual herb control (%) - 19 DAA ECHCG FIMMI gae / ha gai / ha Note Exp Note Exp 8 0 30 - 0 - 16 0 20 - 0 - 32 0 40 - 85 - 0 330 20 - 50 - 8 330 95 44 65 50 16 330 85 36 80 50 32 330 95 52 90 93
Benzyl ester ofCompound A Naptalam Visual herb control (%) - 19 DAA ECHOR gae / ha gai / ha Note Exp 32 0 25 - 0 330 20 -
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Benzyl ester ofCompound A Naptalam Visual herb control (%) - 19 DAA ECHOR gae / ha gai / ha Note Exp 0 660 25 - 0 1320 30 - 32 330 60 40 32 660 20 44 32 1320 70 48
Benzyl ester ofCompound A Naptalam Visual herb control (%) - 19 DAA CYPRO gae / ha gai / ha Note Exp 8 0 50 - 16 0 85 - 32 0 90 - 0 330 0 - 0 1320 50 - 8 330 90 50 16 330 85 85 32 330 100 90 8 1320 90 75 16 1320 100 93 32 1320 100 95
CYPRO Cyperus rotundus L. walnut asparagan, purple ECHCG Echinochloa crusgalli (L). Beauv. barn grass ECHOR Echinochloa oryzoides (Ard). Fritsch water grass, early FIMMI Fimbristylis miliacea (L). Vahl fringe bud, globe LEFCH Leptochloa chinensis (L). Nees sprangle top, chinese SCPMA Schoenoplectus maritimus (L). bleach or
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Bolboschoenus maritimus (L). Palla club sprout, sea gae / ha = equivalent gram of acid per hectare gai / ha = active ingredient in grams per hectare
Obs = observed value
Exp = expected value as calculated by the Colby equation
DAA = days after application
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权利要求:
Claims (9)
[1]
1. Synergistic herbicidal composition, characterized by the fact that it comprises a herbicidally effective amount of:
(a) a compound according to Formula (I) nh ₂
N Y
O
H (D or a benzyl ester of the compound of Formula (I), and (b) an auxin transport inhibitor selected from the group consisting of chlorflurenol-methyl, chlorofurenol, flurenol-methyl and naptalam, when:
(a) is the compound of Formula (I) or benzyl ester thereof and (b) is chlorflurenol-methyl, the weight ratio from (a) to (b) is from 1: 7.8 to 1: 125;
(a) is the compound of Formula (I) or benzyl ester thereof and (b) is chlorofurenol, the weight ratio from (a) to (b) is from 1: 7.9 to 1: 62.8;
(a) is the benzyl ester of the compound of Formula (I) and (b) is flurenol-methyl, the weight ratio of (a) to (b) is from 1: 2 to 1:35; or (a) is the benzyl ester of the compound of Formula (I) and (b) is naptalam, the weight ratio of (a) to (b) is 1: 1 to 1: 165.
[2]
2. Composition according to claim 1, characterized by the fact that it also comprises an agriculturally acceptable adjuvant or vehicle.
[3]
3. Composition according to claim 1 or 2, characterized by the fact that it also comprises a herbicide protector.
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2/3
[4]
4. Method to control undesirable vegetation, characterized by the fact that it comprises the step of contacting a plant, the plant being undesirable vegetation, or the location of the plant, soil or water, with soil or water allowing growth of unwanted vegetation, with a herbicidally effective amount of a combination, as defined in any one of claims 1 to 3.
[5]
5. Method, according to claim 4, characterized by the fact that undesirable vegetation is controlled in rice directly sown, sown in water and transplanted, cereals, wheat, barley, oats, rye, sorghum, corn / canjica, cane sugar, sunflower, rapeseed, canola, sugar beet, soy, cotton, pineapple, pasture, pasture, fallow land, lawn, tree and vine orchards, aquatic vegetation, industrial vegetation management (IVM) or easements (ROW).
[6]
6. Method according to claim 4 or 5, characterized by the fact that (a) and (b) are applied to the plant or to the crop before sprouting.
[7]
Method according to any one of claims 4 to 6, characterized by the fact that undesirable vegetation is controlled in crops tolerant to glyphosate, a synthase inhibitor of
5-enolpyruvilshikimato-3-phosphate (EPSP), glufosinate, glutamine synthetase inhibitor, dicamba, phenoxy auxin, pyridyloxy auxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanodione, phenylpyrazine AC, inhibitor ; gives
Petition 870190048937, of 05/24/2019, p. 9/10
3/3 protoporphyrinogen oxidase (PPO), cellulose biosynthesis inhibitor, mitosis inhibitor, microtubule inhibitor, very long chain fatty acid inhibitor, fatty acid and lipid biosynthesis inhibitor, photosystem I inhibitor, photosystem inhibitor II, triazine, bromoxynil.
[8]
8. Method according to claim 7, characterized by the fact that the tolerant crop has multiple or stacked characteristics conferring tolerance to multiple herbicides or multiple modes of action.
[9]
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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US8883682B2|2014-11-11|

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SA113340755B1|2015-07-07|

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RU2015105957A|2016-09-10|

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US8912120B2|2012-07-24|2014-12-16|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and synthetic auxin herbicides|

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US8871681B2|2012-07-24|2014-10-28|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and certain sulfonylureas|

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US8871680B2|2012-07-24|2014-10-28|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and a di-methoxy-pyrimidine and derivatives thereof|

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US8906826B2|2012-07-24|2014-12-09|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and imidazolinones|

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US8796177B2|2012-07-24|2014-08-05|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-pyridine-2-carboxylic acid or a derivative thereof and acetyl-CoA carboxylaseinhibitors|

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US8912121B2|2012-07-24|2014-12-16|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-pyridine-2-carboxylic acid or a derivative thereof and certain PS II inhibitors|

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US8841233B2|2012-07-24|2014-09-23|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and 4-hydroxyphenyl-pyruvate dioxygenaseinhibitors|

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US8791048B2|2012-07-24|2014-07-29|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and clomazone|

---

US8841234B1|2013-03-15|2014-09-23|Dow Agrosciences, Llc.|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and fungicides|

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AP2015008776A0|2013-03-15|2015-09-30|Dow Agrosciences Llc|Safened herbicidal compositions including pyridine-2-carboxylic acid derivatives for use in corn |

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US9730445B2|2013-03-15|2017-08-15|Dow Agrosciences Llc|Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- pyridine-2-carboxylic acid or a derivative thereof and fungicides|

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TWI689251B|2014-09-15|2020-04-01|美商陶氏農業科學公司|Synergistic weed control from applications of pyridine carboxylic acid herbicides and synthetic auxin herbicides and/or auxin transport inhibitors|

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US11140918B2|2019-03-15|2021-10-12|Flair Products Llc|Personal vaporizer|

法律状态:
2015-02-17| B03A| Publication of a patent application or of a certificate of addition of invention [chapter 3.1 patent gazette]|

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2015-04-14| B03H| Publication of an application: rectification [chapter 3.8 patent gazette]|Free format text: REFERENTE A RPI 2302 DE 18/02/2015, QUANTO AO ITEM (57). |

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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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2018-09-25| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

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2019-03-12| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

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2019-12-10| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2020-02-04| 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 19/07/2013, 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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US201261675093P| true| 2012-07-24|2012-07-24|

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US13/834,706|US8883682B2|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 auxin transport inhibitors|

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