HERBICIDAL COMPOSITIONS COMPENDING 4-AMINO-3-CHLORO-5-FLUORO-6- (4-CHLORO-2-FLUORO-3-METHOXY-PHENYL)

专利摘要:
patent summary: "herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)-pyridine-2-carboxylic acid or a derivative thereof and triazolopyrimidine sulfonamides" provided herein are synergistic herbicidal compositions containing (a) a compound of formula (i): or an agriculturally acceptable salt or ester thereof and (b) tri-azolopyrimidine sulfonamides, including, but not limited to, chloransulam -methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam and pirox-sulam. The compositions provide control of undesirable vegetation, for example in directly cultivated, irrigated and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn , sugarcane, sunflower, rapeseed, canola, sugar beet, soybeans, cotton, pineapple, pastures, lawns, pastures, fallow, peat, orchards and vineyards, aquatic plants, plantations, vegetables, vegetation management industrial (ivm) and rights of way (row).
公开号:BR102013018646B1
申请号:R102013018646-5
申请日:2013-07-22
公开日:2019-06-18
发明作者:Richard Mann；Carla Yerkes；Norbert Satchivi；Monte Weimer；Nelson Carranza
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 6- (4-CHLORINE-2-FLUORO-3-METOXY-PHENY) ACID PYRIDINE-2-CARBOXYLIC OR A DERIVED FROM THE SAME AND TRIDIAZOPHYL SULPHONAMIDES, AND METHOD TO CONTROL UNDESIRABLE VEGETATION.
PRIORITY CLAIM [001] This application claims the benefit of Provisional Patent Application number US 61 / 675,037, filed on July 24, 2012, and Utility Patent Application serial number US 13 / 832,978, filed on March 15, 2012 2013, each of which is incorporated herein by reference in its entirety.
FIELD [002] Provided here are herbicidal compositions comprising (a) 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3methoxyphenyl) pyridine-2-carboxylic acid or an agriculturally acceptable ester or salt thereof and (b) triazolopyrimidine sulfonamides.
[003] Provided here are also methods of controlling undesirable vegetation comprising applying (a) 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or an agriculturally acceptable ester or salt thereof and (b) triazolopyrimidine sulfonamides.
BACKGROUND [004] The protection of crops from weeds and other vegetation that inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in controlling such unwanted growth. Chemical herbicides of many types have been reported in the literature and a large number
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2/84 is in commercial use. However, there remains 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 of Formula (I)
[006] or an agriculturally acceptable salt or ester thereof, and (b) at least one triazolopyrimidine sulfonamide.
[007] A second embodiment includes mixing the first embodiment in which Formula (I) is present in the form of at least one of the following forms: a carboxylic acid, a carboxylate salt, an aralkyl, an alkyl ester, a benzyl unsubstituted, a substituted benzyl, a C1-4 alkyl, and / or an n-butyl ester.
[008] A third modality includes mixing according to the first or second modalities in which triazolopyrimidine sulfonamide (b) is at least one compound selected from the group consisting of: cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, or pyroxsulam or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof of at least one of the aforementioned triazolopyrimidine sulfonamides.
[009] A fourth embodiment includes mixtures according to the first, second, or third embodiment in which the triazolopyrimidine sulfonamide in the mixture is chloransulam-methyl in which the weight ratio
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3/84 of the compound of Formula (I) for chloransulam-methyl 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: from about 1 : 31 to about 137: 1, about 1: 1, about 2: 1, about 4: 1, about 2: 1, about 2.5: 1, about 1: 1, about 0 5: 1, about 10: 1, about 20: 1, about 2.4: 1, about 4.8: 1, about 1: 1.17, about 1: 1.2, about 2.4: 1, about 1:17, about 1: 1.1, about 1.0: 0.55, about 1.0: 1.1, about 1.8: 1, about from 1.2: 1, about 0.15: 1, about 0.3: 1, about 1: 2.2, about 1.0: 4.4, from about 1; 20 to about 1: 100, about 1:10 to about 1:50, about 1; 5 to about 1:25, about 1: 8 to about 15; 1 and about 2; 1 to about 1: 1. [0010] A fifth embodiment includes mixtures according to the first, second, or third embodiment in which the triazolopyrimidine sulfonamide in the mixture is penoxsulam in which the weight ratio of the compound of Formula (I) to penoxsulam is 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: from about 1:23 to about 65: 1, about 1: 1, about 2: 1 , about 1: 4, about 2: 1 to about 1: 4; about 1: 2 to about 2: 1, about 1: 2 to about 4: 1, about 1: 1 to about 4: 1, about 1: 2.5 to about 1: 0, 65, about 1: 1.5, about 1: 0.75; about 1: 0.38, about 2.6: 1, about 1: 4 to about 1: 2, about 1: 4 to about 1: 1, 1.2: 1 to about 10: 1, about 5: 1, about 2.4: 1, about 4.8: 1, about 17: 1, about 11: 1, about 4.3: 1, about 3; 1, about 2.2; 1, about 2.7: 1, about 0.6; 1, about 0.4; 1, about 0.7: 1, about 1.0: 1.25, about 1.0: 1.7, about 3: 1, about 4: 1, about 9.6: 1, about 1; 20 to 1:60, about 1:15 to 50; 1, about 1: 2 to 40: 1, about 1:10 to 30; 1, about 1: 8 to 20: 1, about 1: 7 to 15; 1, about 1 : 6 to about 10: 1, about 1: 5 to 8; 1, about 1: 4 to 6; 1, about 1; 3 to 5; 1, about 1: 2 to about from 4: 1, from about 1: 1 to about 3: 1, from
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4/84 about 1:11 to about 1:46 and about 1: 1 to about 5: 1.
[0011] A sixth embodiment includes mixtures according to the first, second, or third embodiment in which the triazolopyrimidine sulfonamide in the mixture is diclosulam in which the weight ratio of the compound of Formula (I) to diclosulam is 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: about 1:26 to about 26: 1, about 1: 0.38, about 1: 0.75, about 1: 0.38, about 1.3: 1, about 0.7: 1, about 2.6: 1, about 0.7: 1 to about 1.3: 1, about 1.5: 1, about 1:25 to 25: 1, about 1:20 to 20: 1, about 1:15 to 15: 1, about 1:10 to 10: 1, from 1: 5 to about 5: 1, from 1: 4 to about 4: 1, from about 1: 3 to about 3: 1, and about 1.3: 1 to about 0.6: 1.
[0012] A seventh embodiment includes mixtures according to the first, second, or third embodiment in which the triazolopyrimidine sulfonamide in the mixture is flumetsulam in which the weight ratio of the compound of Formula (I) to flumetsulam given in units of gae / ha to gai / ha or gae / ha to gae / ha is selected from the group of ratios of ratios and ratios consisting of: from 1:40 to about 272: 1, about 1.25: 1, about 2.5 : 1, about 5: 1, about 1.5: 1, about 0.32: 1, about 6.4: 1, about 1:35 to 270: 1, about 1:30 to 250: 1, from about 1:20 to 150: 1, from about 1:15 to 100: 1, from 1:10 to 75: 1, from about 1: 9 to about 70: 1, about 1: 8 to about 60: 1, about 1: 7 to 50: 1, about 1: 6 to 40: 1, about 1: 5 to 30: 1, about 1: 4 to 20: 1, from about 1: 3 to 15: 1, from about 1: 2 to 10: 1, from about 1: 3 to about 5: 1 and from about 1.28: 1 to about 1.5: 1.
[0013] An eighth embodiment includes mixtures according to the first, second, or third embodiment in which the triazolopyrimidine sulfonamide in the mixture is metosulam in which the weight ratio of the compound of Formula (I) to metosulam is given in units of gae / there is
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5/84 for gai / ha or gae / ha for gae / ha is selected from the group of ratios of ratios and ratios consisting of: from about 1: 5 to about 300: 1, about 1: 0.8, about from 1: 0.4, about 1.5: 1, from about 1: 4 to 200: 1, from about 1: 3 to 100: 1, from about 1: 2 to about 50: 1 and about 1.28 to about 5.1: 1., A ninth embodiment includes mixtures according to the first, second, or third embodiment in which the triazolopyrimidine sulfonamide in the mixture is florasulam in which the weight ratio of the compound of Formula (I) for florasulam given in units of gae / ha to gai / ha or gae / ha to gae / ha is selected from the group of ratios of ratios and ratios consisting of: from about 1: 5 to about 300: 1 , about 1.0: 0.75, about 7.0: 1.0, about 4: 1, about 2: 3, about 2.1, about 1: 1, about 1: 2 , about 1: 4 about 7: 1, about 1: 4 to 200: 1, about 1: 3 to about 100: 1, about 1:25 to about 50: 1, about 1: 2 to about 30: 1, about 1: 1 to about 25: 1, d and from about 1.35: 1 to about 7: 1 and from about 4: 1 to about 2.3: 1.
[0014] A tenth embodiment includes mixtures according to the first, second, or third modalities in which the triazolopyrimidine sulfonamide in the mixture is pyroxsulam in which the weight ratio of the compound of Formula (I) to pyroxsulam is 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: from about 1:11 to about 75: 1, about 1: 1, about 2: 1 , about 2.3: 1, about 4: 1, about 8: 1, about 11: 1, about 1.0: 0.4, about 1:10 to about 1:70, from about 1: 9 to about 1:60, about 1: 8 to about 1:50, about 1: 7 to about 1:40, about 1: 6 to about 1:30 , from about 1: 5 to about 1:25, from about 1: 4 to about 1:20, from about 1: 3 to about 1:15, from about 1: 2 to about 1 : 10, from about 1: 1 to about 1: 8 and about 2.33: 1.
[0015] An eleventh modality includes any composition
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6/84 according to the first to the tenth modalities in which the mixture further comprises at least one agriculturally acceptable agent selected from the group consisting of an adjuvant, a vehicle, or a protector.
[0016] A twelfth modality includes methods of controlling undesirable vegetation comprising the step of applying or otherwise contacting vegetation and / or soil, and / or water with a herbicidally effective amount of at least one mixture according to the first up to the eleventh modalities.
[0017] A thirteenth modality includes methods according to the twelfth modality in which undesirable vegetation is controlled according to at least the technique selected from the group consisting of: cultivated, irrigated, and / or transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn, sugar cane, sunflower, rapeseed, canola, beet, soy, cotton, pineapple, pastures, lawns, grassland, fallow, peat, orchards and vineyards, aquatic plants, plantations, vegetables , industrial vegetation management (IVM), or easements of passage (ROW).
[0018] A fourteenth modality includes methods according to the twelfth and / or thirteenth modalities in which a herbicidally effective amount of the mixture is applied pre- or postemergentially to at least one of the following: a crop, a field, a ROW , or a rice field.
[0019] A fifteenth modality includes methods according to the eleventh to the fourteenth modalities in which undesirable vegetation can be controlled by practicing at least one of the methods on plants that are resistant or tolerant of agents that act for at least a mode selected from the groups consisting of: glyphosate-, 5-enolpyruvylxiquimate-3-phosphate (EPSP) synthase-, glufosinate-, glutamine synthase-, dicamba-, phenoxy
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7/84 auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanediona-, phenylpyrazoline-, acetyl CoA carboxylase inhibitor (ACCase) -, imidazolinone-, sulfonylurea-, pyrimidinyl thiozine, pyrimidinyl thiozine -, sulfonylaminocarbonyltriazolinone-, acetolactate synthase inhibitor (ALS) or acetohydroxy acid synthase (AHAS) -, 4-hydroxyphenyl-pyruvate dioxigenase (HPPD) inhibitor -, phytene desaturase inhibitor-, carotenoid-biosynthesis inhibitor prototype inhibitor, oxidase (PPO) -, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I- inhibitor, inhibitor of photosystem II-, protoporphyrinogen oxidase (PPO) inhibitor -, triazine-, or bromoxynil.
[0020] A sixteenth modality includes at least one method according to the eleventh to the fifteenth modalities in which a plant that is resistant or tolerant to at least one herbicide is treated, and where the resistant or tolerant crop has traces multiple or overlapping giving tolerance to multiple herbicides or inhibitors of multiple herbicide modes of action, in some modalities the treated plant that expresses resistance to a herbicide is an undesirable vegetation itself.
[0021] A seventeenth modality includes methods according to the sixteenth modality, in which the resistant or tolerant weed is a biotype with resistance or tolerance to multiple herbicides, multiple chemical classes, inhibitors of multiple herbicide modes of action, or through multiple resistance mechanisms.
[0022] An eighteenth modality includes at least one of the methods according to the sixteenth or seventeenth modalities, in which the resistant or tolerant undesirable plant is a biotype
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8/84 resistant or tolerant to at least one agent and / or an agent that acts through at least one mode selected from the group of one or more modes of action consisting of: acetolactate synthase (ALS) inhibitors or acetohydroxy acid synthase (AHAS) ), photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylxiquimate-3-phosphate (EPSP) synthase inhibitors, microtubule assembly inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors, phytene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxigenase (HPPD), mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes of action, quinclorac, arylaminopropionic acids ical, difenzoquat, endotal, or organoarsenic.
[0023] A nineteenth modality includes methods of 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 penoxsulam selected from the group of rates and rate ranges consisting of, approximately: 2, 4.28, 4.8, 8.75, 17, 35, 50 and 100.
[0024] A twentieth modality includes methods according to the fifth and nineteenth modalities in which the controlled plant is at least one plant selected from the group consisting of: IPOHE, LEFCH, LEFPA, BRAPP, ECHCG, SCPMA, CYPDI, CYPES and ISCRU , yet other modalities include controlling plants of the genera consisting of: Ipohe, Leptochloa, Brachiaria, Echinochloa, Scirpus, Cyperus and Ischaemum.
[0025] A twenty-first modality includes methods of competition 870180158415, of 12/04/2018, p. 14/99
9/84 controlling 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 gae / ha of disclosure selected from the group of rates and rate ranges consisting of, approximately: 2, 6.62, 13.25, and 26.5.
[0026] A twenty-second modality includes methods according to the sixth and twenty-first modalities in which the controlled plant is at least one plant selected from the group consisting of: LEFCH, CYPRO, and ECHCG, yet other modalities include controlling plants of the genera consisting in: Leptochloa, Cyperus, and Echinochloa.
[0027] A twenty-third modality includes methods of 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 in a rate, expressed in gai / ha or gae / ha of flumetsulam selected from the group of rates and rate ranges consisting of, approximately: 2, 6.25, 12.5, 25, and 50.
[0028] A twenty-fourth modality includes methods according to the seventh and twenty-third modalities in which the controlled plant is at least one plant selected from the group consisting of: BRARP and CYPIR, yet other modalities include controlling plants of the genera consisting of: Brachiaria and Cyperus.
[0029] A twenty-fifth modality includes methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the eighth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of metosulam selected from the group of rates and rate ranges consisting of, about
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10/84 of: 2, 6.25, 12.5, and 25.
[0030] A twenty-sixth modality includes methods according to the eighth and twenty-fifth modalities in which the controlled plant is at least one plant selected from the group consisting of, LEFCH, yet other modalities include controlling plants of the genus Leptochloa.
[0031] A twenty-seventh modality includes methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the ninth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of florasulam selected from the group of rates and rate ranges consisting of, approximately: 2, 1.25, 3.75, 6.65, 12.5, 25, and 50.
[0032] A twenty-eighth modality includes methods according to the ninth and twenty-seventh modalities in which the controlled plant is at least one plant selected from the group consisting of: SASKR, VEPRE, VIOTR, MATCH, CIRAR, and LAMPU, yet other modalities include controlling plants of the genera consisting of: Salsola, Veronica, Viola, Chamomilla, Cirscum, and Lamium.
[0033] A twenty-ninth modality includes methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the tenth modality in which the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of pyroxsulam selected from the group of rates and rate ranges consisting of, approximately: 2, 3.75, 7.5, and 50.
[0034] A thirtieth modality includes methods according to the tenth and twenty-ninth modalities in which the controlled plant is at least one plant selected from the group consisting of: CIRAR, yet other modalities include controlling plants of the genus Cirsium.
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11/84 [0035] A thirty-first modality includes methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the fourth modality in which the amount of the mixture is applied at a rate, expressed in gai / ha or gae / ha of chloransulam-methyl selected from the group of rates and rate ranges consisting of, approximately: 1.2, 2.19, 4.38, 8.75, 17.5, 35, and 70.
[0036] A thirty-second modality includes methods according to the fourth and thirty-first modalities in which the controlled plant is at least one plant selected from the group consisting of: DIGSA, LEFCH, CYPIR, ECHCG, CYPDI, and FIMMI, yet other modalities include controlling plants of the genera consisting of: Digitaria, Leptochloa, Cyperus, Echinochloa, and Fimbristylis.
[0037] Provided here are also methods of controlling undesirable vegetation comprising applying (a) a compound of Formula (I) or an agriculturally acceptable ester or salt thereof and (b) triazolopyrimidine sulfonamides.
Exemplary triazolopyrimidine sulfonamides include, but are not limited to, cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, and pyroxsulam or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or the same ester.
[0039] Provided here are herbicidal compositions comprising a herbicidally effective amount of (a) a compound of Formula (I)
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12/84 [0040] or an agriculturally acceptable salt or ester thereof, and (b) triazolopyrimidine sulfonamides. The compositions can also contain an agriculturally acceptable adjuvant or vehicle.
[0041] Provided here are also methods of controlling undesirable vegetation comprising applying (a) a compound of Formula (I) or an agriculturally acceptable ester or salt thereof and (b) triazolopyrimidine sulfonamides or an agriculturally acceptable salt or ester thereof.
DETAILED DESCRIPTION
DEFINITIONS [0042] As used here, the compound of Formula (I) has the following structure:
4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methoxyphenyl) -5-fluoropyridine-
2-carboxylic and has been described in U.S. Patent 7,314,849 (B2), which is incorporated herein by reference in its entirety. Exemplary uses of the compound of Formula (I) include controlling undesirable vegetation, including grassy, broadleaf and cyperaceous weeds, in crop and non-crop situations.
[0044] As used here, triazolopyrimidine sulfonamides are a chemical class of herbicides having a triazolopyrimidine sulfonamide core structure. Without being limited to any theory, it is believed that its mode of action involves the inhibition of acetolactate synthase (ALS), an enzyme common to plants and microorganisms but not found in animals. Exemplary herbicidal uses of triazolopi
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13/84 rimidine sulfonamides include, but are not limited to, use for the control of uncomfortable ciperaceae, broadleaved and grassy weeds.
Exemplary triazolopyrimidine sulfonamides include, but are not limited to, chloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, and pyroxsulam.
[0046] As used here, chloransulam-methyl is 3-chloro-2 - [[((5-ethoxy7-fluoro [1,2,4] triazolo [1,5-c] pyrimidin-2-yl) sulfonyl] amino] methyl benzoate and has the following structure:
[0047] Its herbicidal activity is exemplified in Tomlin, C., ed. A World Compendium The Pesticide Manual. 15th ed. Alton: BCPC Publications, 2009 (hereafter The Pesticide Manual, Fifteenth Edition, 2009. ”). Exemplary uses of chloransulam-methyl include its use as a herbicide for post-emergence control of broadleaved weeds in soybeans and other broadleaved crops.
[0048] As used here, diclosulam is M- (2,6-dichlorophenyl) -5-ethoxy7-fluoro [1,2,4] triazolo [1,5-c] pyrimidine-2-sulfonamide and has the following structure:
[0049] Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of diclosulam include its use as a herbicide for the control of broadleaf weeds in peanuts and soybeans.
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14/84 [0050] As used here, florasulam is V- (2,6-difluorophenyl) -8-fluoro5-methoxy [1,2,4] triazolo [1,5-c] pyrimidine-2-sulfonamide and presents the following structure:
[0051] Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of florasulam include its use as a herbicide in the post-emergence control of broadleaved weeds in cereals and corn.
[0052] As used here, flumetsulam is V- (2,6-difluorophenyl) -5methyl [1,2,4] triazolo [1,5-a] pyrimidine-2-sulfonamide and has the following structure:
[0053] Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of flumetsulam include its use as a herbicide for the control of broadleaf weeds and grasses in soybeans, forage peas and corn.
[0054] As used here, metosulam is V- (2,6-dichloro-3-methylphenyl) 5,7-dimethoxy [1,2,4] triazolo [1,5-a] pyrimidine-2-sulfonamide and presents the following structure:
[0055] Its herbicidal activity is exemplified in The Pesticide
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Manual, Fifteenth Edition, 2009. Exemplary uses of metosulam include its use as a herbicide for post-emergence control of broadleaf weeds in wheat, barley and rye, and pre- or post-emergence control of broadleaf weeds in corn.
[0056] As used here, penoxsulam is 2- (2,2-difluoroethoxy) -N (5,8-dimethoxy [1,2,4] triazolo [1,5-c] pyrimidin-2-yl) -6 ( trifluoromethyl) benzenesulfonamide and has the following structure:
[0057] Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of penoxsulam include its use as a herbicide for post-emergence control of Echinochloa spp., Broadleaf weeds and annual cyperaceous weeds in rice, as well such as Echinochloa spp. and broadleaf weeds in sorghum, peat, cereals and orchards and vineyards. In another example, penoxsulam is used to control aquatic weeds in lakes and ponds.
[0058] As used here, piroxsulam is N- (5,7dimethoxy [1,2,4] triazolo [1,5-a] pyrimidin-2-yl) -2-methoxy-4- (trifluoromethyl) -3pyridinesulfonamide the following structure:
[0059] Its herbicidal activity is exemplified in The Pesticide
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16/84
Manual, Fifteenth Edition, 2009. Exemplary uses of pyroxsulam include its use as a herbicide for the post-emergence control of a broad spectrum of annual grass and broadleaf weeds in cereals.
[0060] As used here, herbicide means a compound, for example, an active ingredient that kills, controls or otherwise adversely modifies the growth of plants.
[0061] As used here, an herbicidally effective or vegetation control amount is an amount of active ingredient that causes an adversely modifying effect on vegetation for example, causing variations in natural development, death, effecting regulation, causing desiccation, causing delay , and the like.
[0062] As used here, controlling undesirable vegetation means preventing, reducing, killing, or otherwise adversely modifying the development of plants and vegetation. Described here are methods of controlling undesirable vegetation until the application of certain herbicidal combinations or compositions. Application methods include, but are not limited to, applications to the vegetation or locus thereof, for example, application to the area adjacent to the vegetation, as well as pre-emergence, post-emergence, foliar applications (hand sowing, directed, oriented, by points , mechanical, total area, or rescue), and applications in water (immersed and submerged vegetation, hand sowing, points, mechanics, water injected, granular hand sowing, granular points, agitator bottle or jet spray) manual application methods, by backpack, machine, tractor, or aerial (airplane and helicopter).
[0063] As used here, plants and vegetation include, but are not limited to, germinating seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and vegetation
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17/84 established.
[0064] As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity, or that are or can be converted into plants, water, or soil to the referenced herbicide. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, for example, into plants, water, or soil, to the corresponding carboxylic acid which, depending on the pH, may be in dissociated or not dissociated.
[0065] Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium, and ammonium cations of the Formula:
R ¹ R ² R ³ R ⁴ N + [0066] where R ¹ , R ² , R ³ and R ⁴ all independently represent hydrogen or C1-C12 alkyl, C3-C12 alkenyl or C3C12 alkynyl, each of which is optionally replaced by one or more hydroxy, C1-C4 alkoxy, C1-C4 alkylthio or phenyl groups, provided that R ¹ , R ² , R ³ and R ⁴ are sterically compatible. In addition, any two of R ¹ , R ² , R ³ and R ⁴ together can represent an aliphatic bifunctional portion containing one to twelve carbon atoms and up to two oxygen or sulfur atoms. Salts can be prepared by treatment with a metal hydroxide, such as sodium hydroxide, with an amine, such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisalylamine, 2-butoxy-ethylamine, morpholine, cyclododecylamine, or benzylamine or with a tetraalkylammonium hydroxide, such as tetramethylammonium hydroxide or choline hydroxide.
Exemplary esters include those derived from C1-C12 alkyl, C3-C12 alkenyl, C3-C12 alkynyl or C7-C10 aryl substituted alkyl alcohols, such as methyl alcohol, isopropyl alcohol, 1
Petition 870180158415, of 12/04/2018, p. 23/99
18/84 butanol, 2-ethylhexanol, butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or benzyl alcohols not substituted or substituted. 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 the acids to the alcohol using any number of suitable activating agents such as those used for peptide bonds such as dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); the acids being reacted 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; the corresponding acid being reacted with an appropriate alcohol in the presence of an acid catalyst or by transesterification. COMPOSITIONS AND METHODS [0068] Provided here are herbicidal compositions comprising a herbicidally effective amount of (a) a compound of Formula (I)
[0069] or an agriculturally acceptable salt or ester thereof, and (b) triazolopyrimidine sulfonamides. Exemplary triazolopyrimidine sulfonamides include, but are not limited to, chloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, and pyroxsulam or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof.
[0070] Provided here are also methods of controlling the vegetation
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19/84 undesirable tact comprising contacting vegetation or locus thereof, that is, area adjacent to vegetation, with or applying to the soil or water to prevent the emergence or growth of vegetation a herbicidally effective amount of the compound of Formula (I) or salt agriculturally acceptable or ester thereof and (b) triazolopyrimidine sulfonamides. In certain embodiments, the methods use the compositions described here.
[0071] In addition, in some embodiments, the combination of compound (I) or an agriculturally acceptable salt or ester thereof and triazolopyrimidine sulfonamides, or an agriculturally acceptable salt or ester thereof exhibits synergism, for example, the herbicidal active ingredients are more effective in combination than when applied individually. Synergism was defined as an interaction of two or more factors such that the effect when combined is greater than the effect predicted based on the response of each factor applied separately. ”Senseman, S., ed. Herbicide Handbook. 9th ed. Lawrence: Weed Science Society of America, 2007. In certain embodiments, the compositions exhibit synergy as determined by Colby's equation. Colby, SR 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15: 20-22.
[0072] In some embodiments, the compound of Formula (I) or salt or ester thereof and chloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, and pyroxsulam or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof, are formulated into a composition, mixed in a tank, applied simultaneously, or applied sequentially.
[0073] Herbicidal activity is exhibited by the compounds when they are applied directly to the plant or the locus of the plant at any stage of growth. The observed effect depends on the species of plant to be controlled, the growth stage of the plant,
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20/84 of the application parameters of dilution and spray droplet size, particle size of solid components, environmental conditions at the time of use, the specific compound used, the specific adjuvants and vehicles used, the type of soil, and similar, as well as the amount of chemical applied. These and other factors can be adjusted to promote non-selective or selective herbicidal action. In some embodiments, the compositions described here are applied as a post-emergence application, pre-emergence application, or application in water to irrigated rice fields or bodies of water (for example, ponds, lakes and rivers), to relatively undesirable immature vegetation to obtain maximum weed control.
[0074] In some embodiments, the compositions and methods provided here are used to control weeds in crops, including but not limited to cultivated, irrigated and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn, cane sugar, sunflower, rapeseed, canola, beet, soy, cotton, pineapple, pastures, lawns, pastures, fallow, peat, orchards and vineyards, plantations, vegetables, aquatic plants, industrial vegetation management (IVM) and easements (ROW).
[0075] In certain embodiments, the compositions and methods provided here are used to control weeds in rice. In certain modalities, rice is cultivated, irrigated, or transplanted rice.
[0076] The compositions and methods described here can be used to control undesirable vegetation in glyphosate-tolerant crops, tolerant to 5-enolpyruvylxyquimate-3-phosphate (EPSP) synthase, tolerant to glufosinate, tolerant to glutamine synthase inhibitor, tolerant to dicamba, tolerant to phenoxy auxin, tolerant to pyridyloxy auxin, tolerant to auxin, tolerant to inhibitor of
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21/84 auxin transport, tolerant to aryloxyphenoxypropionate, tolerant to cyclohexanedione, tolerant to phenylpyrazoline, tolerant to acetyl CoA carboxylase (ACCase) inhibitor, tolerant to imidazolinone, tolerant to sulfonylurea, tolerant to pyrimidinylthiobenzoate, tolerant to pyrimidine tolerants triazolopyrimidine, tolerant to sulfonylaminocarbonyltriazolinone, tolerant to acetolactate synthase (ALS) inhibitor or tolerant to acetohydroxy acid synthase (AHAS), tolerant to 4-hydroxyphenylpyruvate dioxigenase (HPPD) inhibitor, tolerant to phytate inhibitor, tolerant to phytate inhibitor carotenoid biosynthesis, tolerant to protoporphyrinogen oxidase (PPO) inhibitor, tolerant to cellulose biosynthesis inhibitor, tolerant to mitosis inhibitor, tolerant to microtubule inhibitor, tolerant to very long chain fatty acid inhibitor, tolerant to biosynthesis inhibitor of fatty acid and lipid, tolerant to photosystem inhibitor I, tolerant to photosystem inhibitor II, tolerant to triazine, and tolerant to bromoxynil (such as, but not limited to, soy, cotton, canola / rapeseed, rice, cereals, corn, sorghum, sunflower, beet, cane sugar, peat, etc.), for example, in combination with glyphosate, EPSP synthase inhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, ACCase inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, dimethoxy-pyrimidines, triazolopyrimidines, sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD inhibitors, inhibitors, inhibitors, phyto inhibitors, inhibitors cellulose, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, inhibited ores of fatty acid and lipid biosynthesis, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil. Compositions and methods can
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22/84 be used to control undesirable vegetation in crops having multiple or overlapping traits, giving tolerance to multiple chemicals and / or inhibitors of multiple modes of action. In some embodiments, the compound of Formula (I) or salt or ester thereof and complementary herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop being treated and that complement the spectrum of weeds controlled by these compounds at the application rate used. In some embodiments, the compositions described here and other complementary herbicides are applied at the same time, as a combination formulation, a tank mixture or sequentially.
[0077] The compositions and methods can be used to control undesirable vegetation in crops having tolerance to agronomic stress (including but not limited to drought, cold, heat, salt, water, nutrient, fertility, pH), tolerance to pests (including but not limited to insects, fungi and pathogens) and traits of crop improvement (including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant height and plant architecture) .
[0078] 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, sugar cane, sunflower, rapeseed, canola, beet, soy, cotton, pineapple , pastures, lawns, pastures, fallow, peat, orchards and vineyards, aquatic plants, plantations, vegetables, industrial vegetation management (IVM) and easements (ROW).
[0079] In some embodiments, the methods provided here are used to control undesirable vegetation in rice. In certain modalities, the undesirable vegetation is Brachiaria platyphylla (Gro
Petition 870180158415, of 12/04/2018, p. 28/99
23/84 seb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf papua, BRAPP), Digitaria sanguinalis (L.) Scop. (mattress grass, DIGSA), Echinochloa species (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (rice grass, ECHCG), Echinochloa crus-pavonis (Kunth) Schult. (jaú grass, ECHCV), Echinochloa colonum (L.) LINK (colony grass, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (corn-rice, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH) , Echinochloa phyllopogon (Stapf) Koso-Pol. (hairy corn, ECHPH), Echinochloa polistachya (Kunth) Hitchc. (capimcanarana, ECHPO), Ischaemum rugosum Salisb. (male grass, ISCRU), Leptochloa chinensis (L.) Nees (Chinese sprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray (bearded rice, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazon sprangletop, LEFPA), Oryza species (red rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (swamp grass, PANDI), Paspalum dilatatum Poir. (capimmelado, PASDI), Rottboellia cochinchinensis (Lour.) W.D. Clayton (carmalote grass, ROOEX), Cyperus species (CYPSS), Cyperus difformis L. (junquinho, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (yellow sedge, CYPES), Cyperus would L. (marsh sedge, CYPIR), Cyperus rotundus L. (aromatic junction, CYPRO), Cyperus serotinus Rottb./CBClarke ( junça brava, CYPSE), species Eleocharis (ELOSS), Fimbristylis miliacea (L.) Vahl (false-cumin, FIMMI), species Schoenoplectus (SCPSS), Schoenoplectus juncoides Roxb. (jonquil, SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus L. Lye (sea clubrush, SCPMA), Schoenoplectus mucronatus L. (chestnut, SCPMU), species Aeschynomene, (jointvetch, AESSS), Alternanthera philoxero. ) Griseb. (alligator grass, ALRPH), Alisma plantago-aquatica L. (rice lettuce, ALSPA), Amaranthus species, (anserinas and amarantos, AMASS), Ammannia coccinea Rottb. (horse mackerel, AMMCO), Commelina benghalensis L. (tra
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24/84 poeraba, COMBE), Eclipta alba (L.) Hassk. (button-grass, ECLAL), Heteranthera limosa (SW.) Willd./Vahl (rice-weed, HETLI), Heteranthera reniformis R. & P. (marshmint, HETRE), species Ipomoea (morning glory, IPOSS), Ipomoea hederacea (L.) Jacq. (viola string, IPOHE), Lindernia dubia (L.) Pennell (false chickweed, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (southeastern cross, LUDLI), Ludwigia octovalvis (Jacq.) Raven (cross-demalta, LUDOC), Monochoria korsakowii Regel & Maack (monocory, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monocory, MOOVA), Murdannia nudiflora (L.) Brenan (trapoeraba, MUDNU), Poligonum pensylvanicum L., (Pennsylvania smartweed, POLPY), Poligonum persicaria L. (silkworm, POLPE), Poligonum hydropiperoides Michx. (POLHP, water pepper), Rotala indica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species, (arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory / Rydb. Ex Hill (sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).
[0080] 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. (fox tail, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oats, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (azevémitaliano, LOLMU), Phalaris minor Retz. (head herb, PHAMI), Poa annua L. (annual dog-hair, POANN), Setaria pumila (Poir.) Roemer & JA Schultes (yellow fox-grass, SETLU), Setaria viridis (L .) Beauv. (green foxtail grass, SETVI), Amarantous retroflexus L. (giant caruru, AMARE), Brassica species (BRSSS), Chenopodium album L. (ançarinha-branca, CHEAL), Cirsium arvense (L.) Scop . (vine thistle, CIRAR /, Galium aparine L. (dehortelão amor, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), La
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25/84 mium purpureum L. (purple lamio, LAMPU), Matricaria recutita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.) Porter (pineapple weed, MATMT), Papaver rhoeas L. (common poppy, PAPRH ), Poligonum convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (sable, SASKR), Sinapis species (SINSS), Sinapis arvensis L. (wild mustard, SINAR), Stellaria media (L.) Vill. (chickweed, STEME), Veronica persica Poir. (verónica-dapérsia, VERPE), Viola arvensis Murr. (field violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR).
[0081] In some modalities, the methods provided here are used to control undesirable vegetation in pasture and pasture, fallow, IVM and ROW. In certain modalities, the undesirable vegetation is Ambrosia artemisiifolia L. (Santiago grass, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaureia maculosa auct. non Lam. (spotted cornflower, CENMA), Cirsium arvense (L.) Scop. (Cardodas-vines, CIRAR), Convolvulus arvensis L. (creeper, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L. (leafy euphorbia, EPHES), Lactuca serriola L./Torn. (prickly lettuce, LACSE), Plantago lanceolata L. (deer horn plantain, PLALA), Rumex obtusifolius L. (cow tongue, RUMOB), Sida spinosa L. (thorn guanxuma, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidago species (solidago, SOOSS), Taraxacum officinale GH Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).
[0082] In some modalities, the methods provided here are used to control the undesirable vegetation found in row crops, orchards and vineyards, and perennial crops. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (foxtail, ALOMY), Avena fatua L. (wild oats, AVEFA), Brachia
Petition 870180158415, of 12/04/2018, p. 31/99
26/84 ria decumbens Stapf. or Urochloa decumbens (Stapf) R.D. Webster (Suriname grass, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R.D. (brachiarian, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf, BRAPP), Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) R.D. Webster (marmalade grass, BRAPL), Cenchrus echinatus L. (grass grass, CENEC), Digitaria horizontalis Willd. (Jamáica mattress grass, DIGHO), Digitaria insularis (L.) Mez ex Ekman (bitter grass, TRCIN), Digitaria sanguinalis (L.) Scop. (mattress grass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (rice grass, ECHCG), Echinochloa colonum (L.) Link (colony grass, ECHCO), Eleusine indica (L.) Gaertn. (potentilla, ELEIN), Lolium multiflorum Lam. (Azevémitaliano, LOLMU), Panicum dichotomiflorum Michx. (dobanhado grass, PANDI), Panicum miliaceum L. (common millet, PANMI), Setaria faberi Herrm. (giant fox-tailed grass, SETFA), Setaria viridis (L.) Beauv. (green foxtail grass, SETVI), Sorghum halepense (L.) Pers. (Capim-maçambará, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (wild sorghum, SORVU), Cyperus esculentus L. (yellow sedge, CYPES), Cyperus rotundus L. (aromatic junction, CYPRO), Abutilon theophrasti Medik. (malvão, ABUTH), Amarantous species (anserinas and amarantos, AMASS), Ambrosia artemisiifolia L. (santiago's herb, AMBEL), Ambrosia psilostachya DC. (western desantiago herb, AMBPS), Ambrosia trifida L. (giant santiago herb, AMBTR), Anoda cristata (L.) Schlecht. (spiked anoda, ANVCR), Asclepias syriaca L. (room captain, ASCSY), Bidens pilosa L. (black sting, BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (field poaia, BOILF), Spermacose latifolia (hot grass, BOILF), Chenopodium album L. (ançarinhawhran, CHEAL), Cirsium arvense (L.) Scop. (Vine thistle, CI
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27/84
RAR), Commelina benghalensis L. (tropical tradescence, COMBE), Datura stramonium L. (estramonio, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden euphorbia, EPHHI), Euphorbia dentata Michx. (toothed euphorbia, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy pulicaria, ERIBO), Erigeron canadensis L. or Conyza canadensis (L.) Cronq. (Canadian erigeron, ERICA), Conyza sumatrensis (Retz.) E. H. Walker (tall fleabane, ERIFL), Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (morning glory of small leaves, IAQTA), Ipomoea hederacea (L.) Jacq. (viola-string, IPOHE), Ipomoea lacunosa L. (white morning glory, IPOLA), Lactuca serriola L./Torn. (prickly lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Richardia species (purslane, RCHSS), Sida species (sida, SIDSS), Sida spinosa L. (thorn guanxuma, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (nightshade, SOLPT), Tridax procumbens L. (bullgrass, TRQPR), or Xanthium strumarium L. (common thistle, XANST).
[0083] In some embodiments, the methods provided here are used to control undesirable vegetation in peat. In certain modalities, the undesirable vegetation is Bellis perennis L. (Margarida, BELPE), Cyperus esculentus L. (yellow tiririca, CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L.) Scop. (mattress grass, DIGSA), Diodia virginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (euphorbia, EPHSS), Glechoma hederacea L. (terrestrial ivy, GLEHE), Hydrocotyle umbellata L. (acariçaba, HYDUM), Kyllinga species (kyllinga, KYLSS), Lamium amplexicaule L. (mint, LAMAM), Murdannia nudiflora (L.) Brenan (trapoeraba, MUDNU), Oxalis species (acetosela, OXASS), Plantago major L. (broadleaf plantain, PLA
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28/84
MA), Plantago lanceolata L. (deer horn / narrow leaf plantain, PLALA), Phyllanthus urinaria L. (stone break, PYLTE), Rumex obtusifolius L. (cow tongue, RUMOB), Stachys floridana Shuttlew. (Betônica, STAFL), Stellaria media (L.) Vill. (chickweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Viola species (wild violet, VIOSS).
[0084] In some embodiments, the compositions and methods provided here are used to control undesirable vegetation consisting of grassy, broadleaved and cyperaceous weeds. In certain embodiments, the compositions and methods provided here are used to control undesirable vegetation including Brachiaria, Chamomilla, Cirsium, Cyperus, Digitaria, Echinochloa, Fimbristylis, Ischaemum, Ipomoea, Lamium, Leptochloa, Matricaria, Salsola, Schoenoplectus, Veronica and Viola.
[0085] In some embodiments, the combination of compound (I) or agriculturally acceptable ester or salt thereof and chloransulammethyl, diclosulam, florasulam, metosulam, penoxsulam, and pyroxsulam or agriculturally acceptable salt or ester thereof is used to control Brachiaria platyphylla ( Griseb.) Nash or Urochloa platyphylla (Nash) RD Webster (broadleaf papua, BRAPP), Chamomilla chamomilla (L.) Rydb. (scented mayweed, MATCH), Cyperus difformis L. (junquinho, ciperácea, CYPDI), Cyperus esculentus L. (yellow nut, CYPES), Cirsium arvense (L.) Scop. (Vine thistle, CIRAR), Cyperus would L. (tiririca-do-brejo, CYPIR), Digitaria sanguinalis (L.) Scop. (mattress grass, DIGSA), Echinochloa crus-galli (L.) Beauv. (rice grass, ECHCG), Echinochloa spp (ECHSS), Fimbristylis miliacea (L.) Vahl (false cumin, FIMMI), Ipomoea hederacea Jacq. (string-deviola, IPOHE), Ischaemum rugosum Salisb. (male grass, ISCRU), Lamium purpureum (L.) (purple lamio, LAMPU), Leptochloa chinensis
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29/84 (L.) Nees (Chinese sprangletop, LEFCH), Leptochloa panicoides (J. Presl) UM.S. Hitchc. (Amazon sprangletop, LEFPA), Salsola iberica (L.) (Barrilha, SASKR), Schoenoplectus juncoides (Roxb.) Palla (Junquilho, SCPJU), Veronica persica Poir. (veronica, VERPE) and Viola tricolor (L.) (wild pansy, VIOTR).
[0086] The compounds of Formula I or agriculturally acceptable salt or ester thereof can be used to control herbicide-resistant or tolerant weeds. The methods using a combination of a Formula I compound or an agriculturally acceptable salt or ester thereof and the compositions described here can also be used to control herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbons) photosystem II (for example, phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g. benzoic acids, phenoxycarboxylic acids, pyridine carboxylic acids, quinoline carboxylic acids), auxin transport inhibitors (eg, phthalates, semicarbazones), photosystem I inhibitors (eg, bipyridyls), 5-enolpyruvylxyquime-3-inhibitors phosphate (EPSP) synthase (eg glyphosate o), glutamine synthetase inhibitors (eg, glufosinate, bialafos), microtubule assembly inhibitors (eg, benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (eg carbamates), acid inhibitors very long-chain fatty acid (VLCFA) (eg acetamides, chloro
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30/84 roacetamides, oxyacetamides, tetrazolinones), fatty acid and lipid synthesis inhibitors (eg, phosphorodithioates, thiocarbamates, benzofurans, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibitors (eg, diphenyl ethers, N-phenylphthalides) oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors (eg clomazone, amitrol, aclonifen), phytene desaturase (PDS) inhibitors (eg amides, ananide, furanides, phenyl, oxides pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxigenase (HPPD) inhibitors (eg, calistemones, isoxazoles, pyrazoles, tricetones), cellulose biosynthesis inhibitors (eg nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides multiple modes of action such as quinclorac, and unclassified herbicides such as arylaminopropionic acids, difenzoquat, endotal, and or ganoarsenics. 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 herbicide modes of action, and biotypes with mechanisms of multiple resistance or tolerance (for example, resistance to the target site or metabolic resistance).
[0087] In certain embodiments of the compositions and methods described herein, the compound of Formula (I) or salt or ester thereof is used in combination with chloransulam-methyl or salt, carboxylic acid, carboxylate salt, or ester thereof. As for the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to chloransulam-methyl or salt, carboxylic acid, carboxylate salt, or ester thereof is within the range of about 1:31 to about 137: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to chloransulam
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31/84 methyl or salt, carboxylic acid, carboxylate salt, or ester thereof is within the range of about 1: 2 to about 10: 1. In special embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to chloransulam-methyl or salt, carboxylic acid, carboxylate salt, or ester thereof is within the range of about 1: 8 to about 15: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to chloransulam-methyl or salt, carboxylic acid, carboxylate salt, or ester thereof is within the range of about 1: 4 to about 22: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to chloransulam-methyl or salt, carboxylic acid, carboxylate salt, or ester thereof is within the range of about 1: 2 to about 11: 1. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl ester and chloransulam-methyl. In one embodiment, the composition comprises the compound of Formula (I) and chloransulam-methyl, wherein the weight ratio of the compound of Formula (I) to chloransulam-methyl is from about 1: 1.7 to about 11: 1. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and chloransulam-methyl, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to chloransulam-methyl is about 1: 2 to about 4: 1. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and chloransulam-methyl, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to chloransulam-methyl is about 1: 2 to about 4: 1. In a special embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and chloransulam-methyl, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to chloransulam-methyl is about 1: 8 at about 15: 1. With respect to the methods, in certain modalities, the methods comprise contacting the undesirable vegetation or locus of this or
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32/84 apply to the soil or water to prevent the emergence or growth of vegetation a composition described here. In some embodiments, the composition is applied at an application rate of about 4 grams of active ingredient per hectare (gai / ha) to about 362 gai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 6 gai / ha to about 40 gai / ha based on the total amount of active ingredients in the composition. In special embodiments, the composition is applied at an application rate of about 6 gai / ha to about 67 gai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting undesirable vegetation or locus thereof or applying to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and chloransulam-methyl or salt, acid carboxylic, carboxylate salt, or ester thereof, for example, sequentially or simultaneously. In some embodiments, chloransulam-methyl or salt, carboxylic acid, carboxylate salt, or ester thereof is applied at a rate of about 2.2 gai / ha to about 62 gai / ha and the compound of Formula (I ) or salt or ester thereof is applied at a rate of about 2 grams of acid equivalent per hectare (gae / ha) to about 300 gae / ha. In some embodiments, chloransulam-methyl or salt, carboxylic acid, carboxylate salt, or ester thereof is applied at a rate of about 1 gai / ha to about 16 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate of about 2 g of acid equivalent per hectare (gae / ha) to about 45 gae / ha. In some embodiments, chloransulam-methyl or salt, carboxylic acid, carboxylate salt, or ester thereof is applied at a rate of about 2.19 gai / ha to about 8.75 gai / ha and the compound of the Formula (I) or salt or ester thereof is applied at a rate of cer
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33/84 ca 4.38 g of acid equivalent per hectare (gae / ha) to about 21.2 gae / ha. In some embodiments, chloransulam-methyl or salt, carboxylic acid, carboxylate salt, or ester thereof is applied at a rate of about 2.19 gai / ha to about 35 gai / ha and the compound of Formula (I ) or salt or ester thereof is applied at a rate of about 4.38 g of acid equivalent per hectare (gae / ha) to about 32 gae / ha. In certain embodiments, the methods use the compound of Formula (I), or its benzyl ester and chloransulam-methyl. In one embodiment, the methods use the compound of Formula (I) and chloransulam-methyl, in which the compound of Formula (I) is applied at a rate of about 5.3 g of acid equivalent per hectare (gae / ha) at about 21.2 gae / ha, and chloransulam-methyl is applied at a rate of about 2.19 gai / ha to about 8.75 gai / ha. In one embodiment, the methods use the compound of Formula (I) and chloransulam-methyl, in which the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare (gae / ha) at about 32 gae / ha, and chloransulam-methyl is applied at a rate of about 2.19 gai / ha to about 35 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and chloransulam-methyl, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare (gae / ha) about
17.5 gae / ha, and chloransulam-methyl is applied at a rate of about 2.19 gai / ha to about 8.75 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and chloransulammethyl, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare ( gae / ha) at about 32 gae / ha, and chloransulam-methyl is applied at a rate of about 2.19 gai / ha to about 35 gai / ha. In certain embodiments, the methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with chloransulam
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34/84 methyl or salt, carboxylic acid, carboxylate salt, or ester thereof are used to control CYPDI, CYPIR, DIGSA, ECHCG, FIMMI, or LEFCH.
[0088] In certain embodiments of the compositions and methods described herein, the compound of Formula (I) or salt or ester thereof is used in combination with diclosulam or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to diclosulam or salt thereof is within the range of about 1:26 to about 26: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to diclosulam or salt thereof is within the range of about 1: 3 to about 2.6: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to diclosulam or salt thereof is within the range of about 1: 3 to about 6: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to diclosulam or salt thereof is within the range of about 1: 1.5 to about 3: 1. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl ester and diclosulam. In one embodiment, the composition comprises the compound of Formula (I) and diclosulam, wherein the weight ratio of the compound of Formula (I) to diclosulam is from about 1: 1.5 to about 3: 1. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and diclosulam, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to diclosulam is from about 1.3: 1 to about 3: 1. With respect to the methods, in certain modalities, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of the vegetation a composition described here. In some embodiments, the composition is applied at an application rate of about 9 grams of
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35/84 active ingredient per hectare (gai / ha) to about 353 gai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 10 gai / ha to about 40 gai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods include contacting undesirable vegetation or locus thereof or applying to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and diclosulam or salt thereof, for example for example, sequentially or simultaneously. In some embodiments, the diclosulam or salt thereof is applied at a rate of about 6.6 gai / ha to about 53 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate from about 2 grams of acid equivalent per hectare (gae / ha) to about 300 gae / ha. In some embodiments, the diclosulam or salt thereof is applied at a rate of about 3 gai / ha to about 26 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate of about from 2 g of acid equivalent per hectare (gae / ha) to about 35 gae / ha. In some embodiments, the diclosulam or salt thereof is applied at a rate of about 6.62 gai / ha to about 13.25 gai / ha and the compound of Formula (I) or its salt or ester is applied in a rate of about 4.38 g of acid equivalent per hectare (gae / ha) to about 17.5 gae / ha. In certain embodiments, the methods use the compound of Formula (I), or its benzyl ester and diclosulam. In one embodiment, the methods use the compound of Formula (I) and diclosulam, in which the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare (gae / ha) to about of 17.5 gae / ha, and diclosulam is applied at a rate of about 6.6 gai / ha to about 13.2 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and diclosulam, in which the benzyl ester of the
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36/84 post of Formula (I) is applied at a rate of about 17.5 g of acid equivalent per hectare (gae / ha), and diclosulam is applied at a rate of about 6.6 gai / ha to about 13.2 gai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with diclosulam or salt thereof are used to control CYPRO, ECHCG, or LEFCH.
[0089] In certain embodiments of the compositions and methods described here, the compound of Formula (I) or salt or ester thereof is used in combination with florasulam or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to florasulam or salt thereof is within the range of about 1: 5 to about 300: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to florasulam or salt thereof is within the range of about 1.5: 1 to about 4: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to florasulam or salt thereof is within the range of about 1: 1.5 to about 14: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to florasulam or salt thereof is within the range of about 1: 0.75 to about 7: 1. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl ester and florasulam. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and florasulam, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to florasulam is from about 1: 0.75 to about 7: 1. With respect to the methods, in certain modalities, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of the vegetation a composition described here. In some
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37/84 modalities, the composition is applied at an application rate of about 3 grams of active ingredient per hectare (gai / ha) to about 310 gai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 6 gai / ha to about 15 gai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods include contacting undesirable vegetation or locus thereof or applying to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and florasulam or salt thereof, for example for example, sequentially or simultaneously. In some embodiments, florasulam or salt thereof is applied at a rate of about 1.0 gai / ha to about 10 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate from about 2 grams of acid equivalent per hectare (gae / ha) to about 300 gae / ha. In some embodiments, florasulam or salt thereof is applied at a rate of about 0.62 gai / ha to about 8 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate from about 2.5 g of acid equivalent per hectare (gae / ha) to about 18 gae / ha. In some embodiments, florasulam or its salt is applied at a rate of about 1.25 gai / ha to about 3.75 gai / ha and the compound of Formula (I) or its salt or ester is applied in a rate of about 5 g of acid equivalent per hectare (gae / ha) to about 8.75 gae / ha. In certain embodiments, the methods use the compound of Formula (I), or its benzyl ester and florasulam. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and florasulam, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 5 g of acid equivalent per hectare (gae / ha) at about 8.75 gae / ha, and florasulam is applied at a rate of about 1.25 gai / ha to about 3.75 gai / ha. In
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38/84 certain modalities, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with florasulam or salt thereof are used to control CIRAR, LAMPU, MATCH, SASKR, VERPE, or VIOTR.
[0090] In certain embodiments of the compositions and methods described herein, the compound of Formula (I) or salt or ester thereof is used in combination with flumetsulam or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to flumetsulam or salt thereof is within the range of about 1:40 to about 272: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to flumetsulam or salt thereof is within the range of about 1:32 to about 45: 1. In special embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to flumetsulam or salt thereof is within the range of about 1: 3 to about 5: 1. In certain embodiments, the compositions comprise the compound of Formula (I) or its benzyl or butyl ester and flumetsulam or salt thereof. With respect to the methods, in certain modalities, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of the vegetation a composition described here. In some embodiments, the composition is applied at an application rate of about 3 grams of active ingredient per hectare (gai / ha) to about 380 gai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 4 gai / ha to about 120 gai / ha based on the total amount of active ingredients in the composition. In special embodiments, the composition is applied at an application rate of about 14 gai / ha to about 57 gai / ha based on the total amount of active ingredients in the composition. In
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39/84 some modalities, the methods include contacting undesirable vegetation or locus thereof or applying to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and flumetsulam or salt thereof , for example, sequentially or simultaneously. In some embodiments, flumetsulam or salt thereof is applied at a rate of about 1.1 gai / ha to about 80 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate from about 2 grams of acid equivalent per hectare (gae / ha) to about 300 gae / ha. In special modalities, flumetsulam or salt thereof is applied at a rate of about 6 gai / ha to about 25 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate of about from 8 grams of acid equivalent per hectare (gae / ha) to about 32 gae / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with flumetsulam or salt thereof are used to control BRAPP or CYPIR.
[0091] In certain embodiments of the compositions and methods described herein, the compound of Formula (I) or salt or ester thereof is used in combination with metosulam or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to metosulam or salt thereof is within the range of about 1: 5 to about 300: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to metosulam or salt thereof is within the range of about 1: 2 to about 70: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to metosulam or salt thereof is within the range of about 1: 0.75 to about 5: 1. In certain embodiments, the compositions comprise the compound of Formula (I) or its benzyl or n-butyl ester and metho
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40/84 sulam. With respect to the methods, in certain modalities, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of the vegetation a composition described here. In some embodiments, the composition is applied at an application rate of about 4 grams of active ingredient per hectare (gai / ha) to about 310 gai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 6 gai / ha to about 70 gai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods include contacting undesirable vegetation or locus thereof or applying to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and metosulam or salt thereof, for example for example, sequentially or simultaneously. In some embodiments, the metosulam or salt thereof is applied at a rate of about 2 gai / ha to about 10 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate of about from 2 grams of acid equivalent per hectare (gae / ha) to about 300 gae / ha. In some embodiments, the metosulam or salt thereof is applied at a rate of about 2 gai / ha to about 10 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate of about from 8 grams of acid equivalent per hectare (gae / ha) to about 32 gae / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with metosulam or salt thereof are used to control LEFCH.
[0092] In certain embodiments of the compositions and methods described herein, the compound of Formula (I) or salt or ester thereof is used in combination with penoxsulam or salt thereof. As for the compositions, in some modalities, the weight ratio of the compound of the
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Formula (I) or salt or ester thereof for penoxsulam or salt thereof is within the range of about 1:25 to about 69: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to penoxsulam or salt thereof is within the range of about 1:11 to about 46: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to penoxsulam or salt thereof is within the range of about 1: 8 to about 8: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to penoxsulam or salt thereof is within the range of about 1: 4 to about 4: 1. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl or n-butyl ester and penoxsulam. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and penoxsulam, wherein the weight ratio of the compound of Formula (I) to penoxsulam is from about 1: 4 to about 2: 1. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and penoxsulam, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to penoxsulam is from about 1: 4 to about 4: 1. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and penoxsulam, wherein the weight ratio of the compound of Formula (I) to penoxsulam is from about 1:11 to about 46: 1. In one embodiment, the composition comprises the n-butyl ester of the compound of Formula (I) and penoxsulam, wherein the weight ratio of the n-butyl ester of the compound of Formula (I) to penoxsulam is about 1: 4 to about 4: 1. With respect to the methods, in certain modalities, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of the vegetation a composition described here. In some embodiments, the composition is applied at an application rate of about 7 grams
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42/84 but of active ingredient per hectare (gai / ha) at about 350 gai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 9 gai / ha to about 250 gai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting undesirable vegetation or locus thereof or applying to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and penoxsulam or salt thereof, for example for example, sequentially or simultaneously. In some embodiments, penoxsulam or salt thereof is applied at a rate of about 7.5 gai / ha to about 50 gai / ha and the compound of Formula (I) or its salt or ester is applied at a rate from about 2 grams of acid equivalent per hectare (gae / ha) to about 300 gae / ha. In some embodiments, penoxsulam or salt thereof is applied at a rate of about 2 gai / ha to about 100 gai / ha and the compound of Formula (I) or its salt or ester is applied at a rate of about from 2 g of acid equivalent per hectare (gae / ha) to about 400 gae / ha. In some embodiments, penoxsulam or salt thereof is applied at a rate of about 4.38 gai / ha to about 50 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate from about 4.38 g of acid equivalent per hectare (gae / ha) to about 200 gae / ha. In certain embodiments, the methods use the compound of Formula (I), or its benzyl or n-butyl ester and penoxsulam. In one embodiment, the methods use the compound of Formula (I) and penoxsulam, in which the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare (gae / ha) to about 35 gae / ha, and penoxsulam is applied at a rate of about 8.75 gai / ha to about 40 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and penoxsulam, in which the
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43/84 benzyl ester of the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare (gae / ha) to about 200 gae / ha, and penoxsulam is applied at a rate of about 4.38 gai / ha to about 50 gai / ha. In one embodiment, the methods use the n-butyl ester of the compound of Formula (I) and penoxsulam, in which the n-butyl ester of the compound of Formula (I) is applied at a rate of about 4.38 g of equivalent acid per hectare (gae / ha) at about 17.5 gae / ha, and penoxsulam is applied at a rate of about 4.38 gai / ha to about 17.5 gai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with penoxsulam or salt thereof are used to control BRAPP, CYPDI, CYPES, ECHCG, ECHSS, IPOHE, ISCRU, LEFCH, LEFPA, or SCPJU.
[0093] In certain embodiments of the compositions and methods described herein, the compound of Formula (I) or salt or ester thereof is used in combination with pyroxsulam or salt thereof. As for the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to pyroxsulam or salt thereof is within the range of about 1:11 to about 75: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to pyroxsulam or salt thereof is within the range of about 1:10 to about 3: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to pyroxsulam or salt thereof is within the range of about 1: 1 to about 2: 0.4. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to pyroxsulam or salt thereof is within the range of about 1:, 4 to about 1: 0.4. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl ester and pyroxsulam. In one embodiment, the composition comprises the benzyl ester of the compound of the
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Formula (I) and pyroxsulam, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to pyroxsulam is about 1: 0.4. With respect to the methods, in certain modalities, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of the vegetation a composition described here. In some embodiments, the composition is applied at an application rate of about 4 grams of active ingredient per hectare (gai / ha) to about 362 gai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 5 gai / ha to about 22 gai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods include contacting undesirable vegetation or locus thereof or applying to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and pyroxsulam or salt thereof, for example for example, sequentially or simultaneously. In some embodiments, pyroxsulam or salt thereof is applied at a rate of about 3 gai / ha to about 23 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate of about from 2 grams of acid equivalent per hectare (gae / ha) to about 300 gae / ha. In some embodiments, pyroxsulam or salt thereof is applied at a rate of about 1 gai / ha to about 12 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate of about from 4 g of acid equivalent per hectare (gae / ha) to about 20 gae / ha. In some embodiments, pyroxsulam or salt thereof is applied at a rate of about 2 gai / ha to about 6 gai / ha and the compound of Formula (I) or its salt or ester is applied at a rate of about from 8 g of acid equivalent per hectare (gae / ha) to about 10 gae / ha. In certain modalities, the methods use the compound of Formula (I), or its is
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45/84 have benzyl and pyroxsulam. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and pyroxsulam, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 8.75 g of acid equivalent per hectare ( gae / ha), and pyroxsulam or salt thereof is applied at a rate of about 3.75 gai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with pyroxsulam or salt thereof are used to control CIRAR.
[0094] The components of the mixtures described here can be applied separately or as part of a multi-part herbicide system.
[0095] The mixtures described here can be applied in combination with one or more other herbicides to control a wider variety of undesirable vegetation. When used in combination with another herbicide, the composition can be formulated with the other herbicide or herbicides, mixed in tank with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be used in combination with the compositions and methods described here include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 2,4-D choline salt, 2,4-D, 2,4-DB esters and amines; 3,4-DA; 3,4-DB; 2,4-DEB; 2.4DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, alidochlor, aloxidim, allyl alcohol, alorac, ametridione, amethrine, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitron, amitrol, anhydrol, sulfamide , atrazine, azafenidin, azimsulfuron, aziprotrin, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentiocarb, bentazon-sodium, benzadox, benzfend, benzofen, benzofen , bia
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46/84 lafos, bicyclopyrone, bifenox, bilanafos, bispiribac-sodium, borax, bromacil, bromobonyl, bromobutide, bromophenoxin, bromoxynil, brompirazon, butachlor, butafenacil, butamiphos, butenachlor, buturidone, buthidazol, buthidazol, buthidazol, buthidazol, buthidazol, buthidazol, buthidazol, buthidazol, buturidone, buthidazol, buthidazol, butydroxyl, buturidone cacodyl, cafenstrol, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazol clorprocarb, carfentrazone-ethyl, CDEA, CEPC, clomethoxyfen, chloramben, chloranocril, chlorazifop, chlorazine, chlorinfurur, chlorlorflon, chlorinflour chlorflurenol, chloridazon, chlorimuron, chlornitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorprofam, chlorsulfuron, chlortal, chlortiamid, cinidon-ethyl, cinmetilin, cinosulfuron, cisanilide, cletodim, cliodinate, cliodinate, cliodinophar, propionate cloproxidim, clopyralid, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumiluron, cyanatrine, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxidim, cycluron, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, cipromid, daimuron, dalapon, dazomet, delaclor, desmedifam, desmethrin, di-alate, dicamba, diclobenil, dichloralurea, dichloromethane, dichloro-dichlorohydrochloride, dichlorohydrochloride dietamquat, dietathyl, diphenopenten, diphenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimetachlor, dimetamethrin, dimethenamid, dimethenamid-P, dimexane, dimidazon, dinitramine, dinofenate, dinimide, dinino, dinoprop, dinino disul, dithiopir, diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, endotal, epronaz, EPTC, erbon, esprocarb, etalfluralin, etbenzamide, etametsulfuron, etidimuron, etiolate, etobenzamid, etobenzamid, etofenzate, etofumesate, etofumesate, etoxum, ethoxy etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop, fenoxapropP-ethyl, phenoxaprop-P-ethyl + isoxadifen-ethyl, phenoxasulfone, fenteracol, fentiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flampropM, fla zasulfuron, fluazifop, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, flucloralin, flufenacet, flufenican, flufenpir-ethyl, flume
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47/84 zin, flumiclorac-pentila, flumioxazin, flumipropin, fluometuron, fluorodifen, fluoroglycophen, fluoromidine, fluoronitrofen, fluotiuron, flupoxam, flupropacil, flupropanate, flupirsulfuron, fluridone, fluroxuron, fluroxyrone, fluroxyrone, fluroxyrone, fluroxyrone , phosamine, fumichlorac, furyloxifen, glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosate salts and esters, halauxifen, halauxifenmethyl, halosafen, halosulfuron-methyl, haloxidine, haloxifop-metha, , hexazinone, imazametabenz, imazamox, imazapic, imazapyr, imazaquin, imazosulfuron, chloransulam-methyl, indanofan, indaziflam, iodobonyl, iodomethane, iodosulfuron, iodosulfuron-ethyl-sodium, iofensulfuron, isoxamine, ipoxyl, isoxyzone , isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxaclortol, isoxaflutol, isoxapyrifop, carbutilate, cetospiradox, lactofen, l enacil, linuron, MAA, MAMA, esters and amines of MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazuron, metazurach, metabenztiazuron, metalpropalin, metazol, metiobencarb, metiozolin, metiuron, metometon, metoprotrin, methyl bromide, methyl isothiocyanate, metildimron, metobenzuron, metobromuron, metolachlor, methoxy, mono-methoxy, methoxyuron, metulfuron, metulfuris, , monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipiraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, orto-dichloronadine, oxo-oxide, oxo-oxide, oxo , oxaziclomefone, oxifluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate, pelargonic acid, pendimetalin, pentachlorophenol, pentanochlor, pentoxazone, perf luidone, petoxamid, fenisofam, fenmedifam, fenmedifam-ethyl, fenobenzuron, phenylmercury acetate, picloram,
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48/84 picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanide, pretilachlor, primisulfuron-methyl, prociazine, prodiamine, profluazole, profluralin, profoxidim, proglinazine, proexadione-calcic, propetramide, prometon, prometon, prometon, prometon, propanil, propaquizafop, propazin, profam, propisochlor, propoxycarbazone, propyrisulfuron, propizamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prinaclor, pidanon, piraclonil, piraflufen-ethyl, pirasulfotol, pyrazoxyl, pyrazoxyl, pyrazuryl, pyrazuryl, pyrazuryl, pyrazol, pyrichlor, pyridafol, pyridate, pyriftalid, piriminobac, pyrimisulfan, piritiobacsodium, pyroxassulfone, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-P-ethyl, rhodetanil, rimsulfuron, saflufenacil, metlufenacil, seclufenacil, simazine, simeton, symmetrine, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfalate, sulfentrazone, south fometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglicapin, swep, SYN-523, TCA, tebutam, tebutiuron, tefuriltrione, tembotrione, tepraloxidim, terbacil, terbucarb, terbuclor, terbumeton, tertururine, terbutyrine, terbutyrin, terbutilin, terbutyl, terbutyrin, terbutyl, terbutyrin, terbutyl, terzutyl, terturutine, terbutyrin , tidiazuron, tiencarbazone-methyl, tifensulfuron, tifensulfurn-methyl, thiobencarb, thiocarbazil, thioclorin, topramezone, tralcoxidim, triafamone, tri-alate, triasulfuron, triaziflam, trilzone, tribenuron, triclinone, tribenon, triluron, tribenuron triclopir, tridifano, trietazine, trifloxisulfuron, trifluralin, triflusulfuron, trifop, trifopsima, trihydroxythriazine, trimeturon, tripropindan, tritac tritosulfuron, vernolate, xylachlor and salts, the same esters and isomers, and isomers.
[0096] The compositions and methods described here, can also be used in combination with glyphosate, 5enolpyruvylxiquimate-3-phosphate (EPSP) synthase, glufosinate, glutamine synthetase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropio
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49/84 natos, cyclohexanediones, phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, dimethoxy-pyrimidines, triazolopyrimidines, sulfonylaminocarbonyltriazolides, (acidosis) inhibitors 4-hydroxyphenyl-pyruvate dioxigenase (HPPD), phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, fatty acid inhibitors very long, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines, and tolerant to bromoxynil in glyphosate, tolerant to EPSP synthase inhibitor, tolerant to glufosinate, tolerant to glutamine synthetase inhibitor, tolerant dicamba, tolerant to phenoxy auxin, tolerant to pyridyloxy auxin, tol auxin-erant, 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 triazolone, triazolone and trinilinolinone; tolerant to ALS or AHAS, tolerant to HPPD, tolerant to phyteno desaturase inhibitor, tolerant to carotenoid biosynthesis inhibitor, tolerant to PPO, tolerant to cellulose biosynthesis inhibitor, tolerant to mitosis inhibitor, tolerant to 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 cultures having multiple or overlapping traits giving tolerance to multiple chemicals and / or multiple modes of action through single and / or multiple resistance mechanisms. In some embodiments, the compound of Formula (I) or salt or ester thereof and her
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50/84 complementary bicide or salt or ester thereof are used in combination with herbicides that are selective for the crop being treated and that complement the spectrum of weeds controlled by these compounds at the rate of application used. In some embodiments, the compositions described here and other complementary herbicides are applied at the same time, as a combination formulation, as a tank mixture or sequentially.
[0097] In some embodiments, the compositions described here are used in combination with one or more herbicide protectors, such as AD-67 (MON 4660), benoxacor, bentiocarb, brassinolide, cloquintocet (mexila), ciometrinila, daimuron, diclormid, dicyclonon, dimepiperate, disulfoton, fenclorazol-ethyl, fenclorin, flurazole, fluxofenim, furilazol, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpir-diethyl, mefenate, naphthalic anhydride (NA), amine oxide and Na14 oxide; phenyl-sulfonylbenzoic, to enhance its selectivity. In some modalities, protectors are used in rice, cereal, or corn environments. In some embodiments, the protector is cloquintocet or an ester or salt thereof. In certain embodiments, cloquintocet is used to antagonize the harmful effects of the compositions on rice and cereals. In some modalities, the protector is cloquintocet (mexila).
[0098] 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, naphthaleneacetamide, α-naphthalenoacetic acids, benzyladenine , 4-hydroxyphenethyl alcohol, kinetin, zeatin, endotal, etefon, pentachlorophenol, tidiazuron, tribufos, aviglycine, etefon, maleic hydrazide, gibberellins, gibberellic acid, abscisic acid, ancimidol, phosamine, glyphosine, meziride, jasmine , 2,3,5-triiodobenzoic acid, morphactins, dichlorflurenol, flurprimidol, mefluidide,
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51/84 paclobutrazol, tetcyclacis, uniconazole, brassinolide, brassinolide-ethyl, cycloheximide, ethylene, methasulfocarb, proexadione, triapentenol and trinexapac.
[0099] In some embodiments, plant growth regulators are used in one or more crops or environments, such as rice, cereal crops, maize, broadleaf crops, rapeseed / canola, peat, pineapple, sugar cane, sunflower, pastures, lawns, pastures, fallow, orchards and vineyards, plantations, vegetables, and non-crop environments (ornamental). In some embodiments, the plant growth regulator is mixed with the compound of Formula (I), or mixed with the compound of Formula (I) and a triazolopyrimidine sulfonamide to cause a preferentially beneficial effect on plants.
[00100] In some embodiments, the compositions provided here further comprise at least one agriculturally acceptable adjuvant or vehicle. Suitable adjuvants or vehicles should not be phytotoxic to valuable crops, particularly at the concentrations used in applying the compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other ingredients in the composition. Such mixtures can be designed for application directly to weeds or their location or they can be concentrated or formulations that are usually diluted with additional vehicles and adjuvants before application. They can be solid, such as, for example, dust, granules, water-dispersible granules, or wetting powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be supplied as a premix or mixed in a tank.
[00101] Suitable agricultural adjuvants and vehicles include, but are not limited to, oleaginous culture concentrate; ethoxylate
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52/84 nonylphenol; benzylcocoalkylimethyl quaternary ammonium salt; combination of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9-C11 alkyl polyglycoside; phosphate alcohol ethoxylate; natural primary alcohol ethoxylate (C12-C16); di-sec-butylphenol EO-PO block copolymer; polysiloxanomethyl buffer; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); dioleate-99 of PEG (400).
[00102] Liquid vehicles that can be used include water and organic solvents. Organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (containing 4 to 6 hydroxy), such as 2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, dioctyl succinate, adipate di-butyl, dioctyl phthalate and the like; esters of mono-, di- and polycarboxylic acids and the like. Specific organic solvents include, but are not limited to, toluene, xylene, petroleum naphtha, culture oil, acetone, methyl ethyl ketone, cyclohexanone, trichlorethylene, perchlorethylene, ethyl acetate, amyl acetate, butyl acetate, monomethyl ether propylene glycol and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerin, V-methyl-2-pyrrolidinone, M, M-dimethyl alkylamides, dimethyl sulfoxide, fertilizers liquids and the like. In certain modalities, water is the vehicle for the dilution of
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53/84 concentrates.
[00103] Suitable solid vehicles include, but are not limited to, talc, pyrophyllite clay, silica, atapulgite clay, kaolin clay, diatom, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller earth, stone husks cotton, wheat flour, soy flour, pumice stone, wood flour, nutshell flour, lignin, cellulose and the like.
[00104] In some embodiments, the compositions described here further comprise one or more active surface agents. In some embodiments, such surface-active agents are used in both solid and liquid compositions, and in certain embodiments those designed to be diluted with the vehicle prior to application. Surface active agents can be anionic, cationic or non-ionic in character and can be used as emulsifying agents, wetting agents, suspending agents, or for other purposes. Surfactants that can also be used in the present formulations are described, inter alia, in McCutcheon's Detergents and Emulsifiers Annual, ”MC Publishing Corp., Ridgewood, New Jersey, 1998 and in Encyclopedia of Surfactants,” Vol. I-III, Chemical Publishing Co ., New York, 1980 - 81. Surface active agents include, but are not limited to, salts of alkyl sulfates, such as diethanol-ammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecyl-benzenesulfonate; alkylphenol-alkylene oxide addition products, such as C18 nonylphenol ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol ethoxylate-Cw; soaps, such as sodium stearate; alkylnaphthalene sulfonate salts, such as sodium dibutyl naphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di (2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as trimethyl ammonium lauryl chloride;
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54/84 polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono- and dialkyl phosphate esters; vegetable or seed oils such as soybean oil, rapeseed / canola oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil , palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters from the vegetable oils above, and in certain embodiments, methyl esters.
[00105] 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 carrier or as an active surface agent.
[00106] 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, odorants, diffusion agents, penetration aids, adhesion agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like. The compositions can also contain other compatible components, for example, other herbicides, plant growth regulators, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer vehicles such as ammonium nitrate, urea and the like .
[00107] In some embodiments, the concentration of active ingredients in the compositions described here is about 0.0005 to 98 weight percent. In some embodiments, the concentration is about 0.0006 to 90 weight percent. In compositions designed to be used as concentrates, the active ingredients, in certain
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55/84 modalities are present in a concentration of about 0.1 to 98 weight percent, and in certain modalities of about 0.5 to 90 weight percent. Such compositions are, in certain embodiments, diluted with an inert carrier, such as water, prior to application. The diluted compositions usually applied to weeds or the location of the weeds contain, in certain embodiments, from about 0.0003 to 1.5 weight percent of active ingredient and in certain embodiments contain from about 0.0008 to 1 , 0 weight percent.
[00108] The present compositions can be applied to weeds or to their location by the use of conventional sprinklers, aerial or terrestrial sprayers, and granule applicators, by addition to irrigation water or rice paddies, and by other conventional means known to those skilled in the art. in the technique.
[00109] The modalities and examples described below are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses, or combinations with respect to the compositions described here will be evident to a person of ordinary skill in the technique without departing from the spirit and scope of the claimed subject.
EXAMPLES
Example I. Evaluation of Herbicidal Mixtures Applied Post Foliar Emergence for Weed Control in Rice Sown Directly in the Greenhouse.
[00110] Seeds or small nuts of the desired test plant species were planted in a soil matrix prepared by mixing a loamy or sandy-loam soil (for example, 28.6 percent slime, 18.8 percent clay, and 52.6 percent sand, with a pH of about 5.8 and an organic matter content of about 1.8 percent) and limestone sandstone at a ratio of 80 to 20. The soil matrix contained in plastic vases with a volume of 1 quarter and a
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56/84 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 14 h photoperiod that was maintained at around 29 ° C during the day and around 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 1000 Watt metal halide lamps suspended as needed. The plants were used for the test when they reached the first to the fourth true leaf stage.
[00111] The treatments consisted of 4-amino-3-chloro-5-fluor-6- (4-chloro-2-fluoro-3-methoxy-phenyl) pyridine-2-carboxylic acid or esters (Compound A), each formulated as a SC (suspension concentrate), and various herbicidal components alone and in combination. Compound A forms were applied on an acid equivalent basis.
[00112] The forms of compound A (compound of Formula I) tested include:
OH
Compound A Acid
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O
Compound A n-butyl ester
Benzyl ester of Compound A [00113] Other herbicidal components were applied on an active ingredient basis and included acetolactate synthase (ALS) inhibiting herbicides (chemical class of sulfonamide) penoxsulam formulated as Grasp ^® SC, diclosulam formulated as Strongarm ^® , and chloransulam -methyl formulated as FirstRate ^® , flumetsulam formulated as Flumetsulam WG, and metosulam formulated as Eclipse®.
[00114] The treatment requirements were calculated based on the rates being tested, the concentration of the active ingredient or acid equivalent in the formulation, and an application volume of 12 mL at a rate of 187 L / ha.
[00115] For treatments comprised of formulated compounds, the weighted amounts of the compounds were placed individually in 25 ml glass bottles and diluted in a volume of 1.25% (v / v) of Agri-Dex® culture oil concentrate to get 12X stock solutions. If a test compound did not dissolve easily, the mixture was heated and / or sonicated. Application solutions were prepared by adding an appropriate amount of each
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58/84 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 culture oil concentrate so that the solutions of Final sprays contained 1.25 +/- 0.05% (v / v) of culture oil concentrate.
[00116] For treatments comprised of technical compounds, weighted amounts can be placed individually in 25 ml glass vials and dissolved in a 97: 3 v / v volume of acetone / DMSO to obtain 12X stock solutions. If a test compound does not easily dissolve, the mixture can be heated and / or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (for example, 1 ml) and diluted to the appropriate final concentrations with the addition of 10 ml of a 1.5% (v / v) aqueous mixture of culture oil concentrate so that the final spray solutions contain 1.25% (v / v) of oil culture concentrate. When technical materials are used, concentrated stock solutions can be added to the spray solutions so that the final concentrations of acetone and DMSO in the application solutions are 16.2% and 0.5%, respectively.
[00117] For treatments comprised of formulated and technical compounds, weighted amounts of technical materials can be placed individually in 25 mL glass vials and dissolved in a 97: 3 v / v volume of acetone / DMSO to obtain 12X stock solutions , and measured amounts of the formulated compounds can be placed individually in 25 ml glass vials and diluted in a volume of 1.5% (v / v) of oil or culture concentrate to obtain 12X stock solutions. If a test compound does not easily dissolve, the mixture can be heated and / or sonicated. Application solutions can be prepared by adding a
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59/84 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 oil or culture concentrate water so that the final spray solutions contain 1.25% (v / v) of culture oil concentrate. As needed, additional water and / or 97: 3 v / v acetone / DMSO can be added to the individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared are 8.1% and 0, 25%, respectively.
[00118] All stock solutions and application solutions were visually inspected for compatibility of the compound before application. Spray solutions were applied to the plant material with a suspended 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 18 to 20 inches (46 50 cm) above the cover height of the average plant. Control plants were sprayed in the same way with the blank solvent test.
[00119] 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 when compared to that of untreated plants was visually determined and recorded on a scale of 0 to 100 percent where 0 corresponds to no damage or inhibition of growth and 100 corresponds to complete death .
[00120] Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations.
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Weeds 15: 20-22.).
[00121] 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) [00122] A = observed effectiveness of active ingredient A at the same concentration as used in the mixture.
[00123] B = observed effectiveness of active ingredient B at the same concentration as used in the mixture.
[00124] The tested compounds, the application rates used, plant species tested, and results are provided in tables 1 to 9.
TABLE 1. Synergistic Activity of Herbicidal Compositions of Compound A and Penoxsulam Applied to Leaves in Weed Control in a Rice Culture System.
Compound A Acid Penoxsulam Visual Weed Control (%) 27 DAA IPOHE gae / ha gai / ha Note Esp 4.38 0 10 - 8.75 0 10 - 17.5 0 10 - 0 8.75 15 - 0 17.5 20 - 4.38 8.75 95 24 8.75 8.75 60 24 17.5 8.75 20 24 4.38 17.5 95 28 8.75 17.5 20 28 17.5 17.5 40 28
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Compound A Acid Penoxsulam Visual Weed Control (%) 19 DAA LEFCH gae / ha gai / ha Note Esp 19.4 0 5 - 0 40 0 - 19.4 40 30 5
TABLE 2. Synergistic Activity of Herbicidal Compositions of Compound A and Penoxsulam N-Butyl Ester Applied to Leaves in Weed Control in a Rice Culture System.
Compound A n-butyl ester Penoxsulam Visual Weed Control (%) - 21 DAA BRAPP gae / ha gai / ha Note Esp 4.38 0 0 - 8.75 0 40 - 0 4.38 0 - 0 8.75 20 - 4.38 4.38 40 0 8.75 4.38 40 40 4.38 8.75 50 20 8.75 8.75 60 52
Compound A n-butyl ester Penoxsulam Visual Weed Control (%) - 27 DAA ECHCG gae / ha gai / ha Note Esp 4.38 0 0 - 8.75 0 0 - 17.5 0 90 - 0 4.38 0 - 0 8.75 30 - 4.38 4.38 60 0 8.75 4.38 70 0 17.5 4.38 95 90
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Compound A n-butyl ester Penoxsulam Visual Weed Control (%) - 27 DAA ECHCG gae / ha gai / ha Note Esp 4.38 8.75 95 30 8.75 8.75 80 30 17.5 8.75 90 93
Compound A n-butyl ester Penoxsulam Visual Weed Control (%) - 27 DAA IPOHE gae / ha gai / ha Note Esp 4.38 0 10 - 8.75 0 10 - 17.5 0 10 - 0 8.75 15 - 0 17.5 20 - 4.38 8.75 95 24 8.75 8.75 95 24 17.5 8.75 50 24 4.38 17.5 100 28 8.75 17.5 50 28 17.5 17.5 95 28
TABLE 3. Synergistic Activity of Herbicidal Compositions of Compound A and Penoxsulam Benzyl Esters Applied to Leaves in Weed Control in a Rice Culture System.
Benzyl ester of Compound A Penoxsulam Visual Weed Control (%) - 21 DAA BRAPP gae / ha gai / ha Note Esp 17.5 0 80 - 0 4.38 0 - 0 8.75 20 - 0 17.5 40 - 17.5 4.38 95 80
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Benzyl ester of Compound A Penoxsulam Visual Weed Control (%) - 21 DAA BRAPP gae / ha gai / ha Note Esp 17.5 8.75 95 84 17.5 17.5 95 88
Benzyl ester of Compound A Penoxsulam Visual Weed Control (%) - 27 DAA IPOHE gae / ha gai / ha Note Esp 4.38 0 10 - 8.75 0 10 - 17.5 0 10 - 0 4.38 10 - 0 8.75 15 - 0 17.5 20 - 4.38 4.38 50 19 8.75 4.38 40 19 17.5 4.38 95 19 4.38 8.75 50 24 8.75 8.75 95 24 17.5 8.75 40 24 4.38 17.5 100 28 8.75 17.5 60 28 17.5 17.5 70 28
Benzyl ester of Compound A Penoxsulam Visual Weed Control (%) - 21 DAA ISCRU gae / ha gai / ha Note Esp 8 0 20 - 16 0 0 - 0 10 0 - 0 20 0 - 8 10 100 20
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Benzyl ester of Compound A Penoxsulam Visual Weed Control (%) - 21 DAA ISCRU gae / ha gai / ha Note Esp 16 10 100 0 8 20 15 20 16 20 100 0
TABLE 4. Synergistic activity of Compound A and Diclosulam Herbicidal Compositions Applied to Leaves in the Control of Weeds Common to Rice Culture Systems.
Compound A Acid Diclosulam Visual Weed Control (%) - 20 DAA LEFCH gae / ha gai / ha Note Esp 4.38 0 15 - 8.75 0 30 - 17.5 0 50 - 0 6.62 0 - 4.38 6.62 55 15 8.75 6.62 50 30 17.5 6.62 55 50
TABLE 5. Synergistic Activity of Herbicidal Compositions of Compound A and Diclosulam Benzyl Esters Applied to Leaves in Weed Control Common to Rice Culture Systems.
Benzyl ester of Compound A Diclosulam Visual Weed Control (%) - 20 DAA LEFCH gae / ha gai / ha Note Esp 17.5 0 60 - 0 6.62 0 - 0 13.25 20 - 17.5 6.62 75 60 17.5 13.25 70 68
TABLE 6. Synergistic Activity of Herbicidal Acid Compositions
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Compound A Acid Chloransulammethyl Visual Weed Control (%) -20 DAA DIGSA gae / ha gai / ha Note Esp 5.3 0 10 - 10.6 0 20 - 21.2 0 20 - 0 2.19 10 - 5.3 2.19 45 19 10.6 2.19 30 28 21.2 2.19 40 28
Compound A Acid Chloransulammethyl Visual Weed Control (%) - 20 DAA LEFCH gae / ha gai / ha Note Esp 5.3 0 0 - 10.6 0 10 - 21.2 0 15 - 0 4.38 0 - 0 8.75 0 - 5.3 4.38 15 0 10.6 4.38 15 10 21.2 4.38 90 15 5.3 8.75 50 0 10.6 8.75 10 10 21.2 8.75 75 15
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TABLE 7. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Chloransulam-Methyl Applied to Leaves in the Control of Weeds Common to Rice Culture Systems.
Benzyl ester of Compound A Chloransulammethyl Visual Weed Control (%) - 20 DAA LEFCH gae / ha gai / ha Note Esp 4.38 0 10 - 8.75 0 20 - 0 2.19 0 - 0 4.38 0 - 4.38 2.19 25 10 8.75 2.19 15 20 4.38 4.38 15 10 8.75 4.38 50 20
Benzyl ester of Compound A Chloransulammethyl Visual Weed Control (%) - 20 DAA CYPIR gae / ha gai / ha Note Esp 4.38 0 15 - 8.75 0 60 - 17.5 0 90 - 0 4.38 70 - 0 8.75 85 - 4.38 4.38 90 75 8.75 4.38 100 88 17.5 4.38 90 97 4.38 8.75 99 87 8.75 8.75 95 94 17.5 8.75 100 99
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TABLE 8. Synergistic Activity of Herbicidal Compositions of Compound A and Flumetsulam Benzyl Ester Applied to Leaves in the Control of Weeds Common to Rice Culture Systems.
Benzyl ester of Compound A Flumetsulam Visual Weed Control (%) - 22 DAA BRAPP gae / ha gai / ha Note Esp 8 0 60 - 16 0 60 - 32 0 90 - 0 6.25 30 - 8 6.25 85 72 16 6.25 80 72 32 6.25 95 93
Benzyl ester of Compound A Flumetsulam Visual Weed Control (%) - 22 DAA CYPIR gae / ha gai / ha Note Esp 8 0 20 - 16 0 85 - 0 6.25 20 - 0 12.5 55 - 0 25 30 - 8 6.25 100 36 16 6.25 100 88 8 12.5 60 64 16 12.5 100 93 8 25 70 44 16 25 100 90
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TABLE 9. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Metosulam Applied to Leaves in the Control of Weeds Common to Rice Culture Systems.
Benzyl ester of Compound A Metosulam Visual Weed Control (%) - 22 DAA LEFCH gae / ha gai / ha Note Esp 8 0 10 - 16 0 25 - 32 0 55 - 0 6.25 15 - 8 6.25 45 24 16 6.25 40 36 32 6.25 65 62
BRAPP Brachiaria platyphylla (Griseb.) Nash or
Urochloa platyphylla (Nash) R.D.Hoster Papua, broadleaf
CYPIR Cyperus would L.
cracked rice, rice
DIGSA Digitaria sanguinalis (L.) Scop.
in
ECHCG Echinochloa crusgalli (L.) Beauv. IPOHE Ipomoea hederacea Jacq. ISCRU Ischaemum rugosum Salisb.
LEFCH Leptochloa chinensis (L.) Nees mattress grass, grancapim-glory-morning rice, sprangletop male grass ivy, Chinese gae / ha = grams of acid equivalent per hectare gai / ha = grams of active ingredient per hectare
Obs = observed value
Esp = expected value as calculated by the Colby equation
DAA = days after application
Example II. Evaluation of Herbicide Mixtures Applied in Water for Weed Control in Greenhouse Transplanted Rice.
[00125] Small weed seeds or nuts of the desired test plant species were planted in muddy soil (la
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69/84 ma) prepared by mixing a fragmented, non-sterile mineral soil (50.5 percent slime, 25.5 percent clay, and 24 percent sand, with a pH of about 7.6 and an organic matter content of about 2.9 percent) and water in a volumetric ratio of 1: 1. The prepared sludge was dispensed in 365 mL aliquots in 0.48 liter 16 oz (oz.) Unperforated plastic pots with a surface area of 86.59 square centimeters (cm ² ) leaving a top space of 3 centimeters in each pot. The sludge was allowed to dry overnight before planting or transplanting. Rice seeds were planted in a Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic-covered trays. The seedlings in the second or third stage of leaf growth were transplanted in 840 mL of mud contained in 0.95 liter (32 oz.) Unperforated plastic pots with a surface area of 86.59 cm ² 4 days before herbicide application. The rice paddy was created by filling the top space of the pots with 2.5 to 3 cm of water. When necessary to ensure good germination and healthy plants, a fungicide treatment and / or other chemical or physical treatment was applied. The plants were grown for 4 to 22 days in a greenhouse with an approximate 14 h photoperiod that was maintained at around 29 ° C during the day and around 26 ° C at night. Nutrients were added as Osmocote® (19: 6: 12, N: P: K + minor nutrients) in 2 g per 0.48 liter (16 oz.) Pot and 4 g per 0.95 liter (32 oz. Pot) .). Water was added on a regular basis to keep the paddy from flooding, and supplementary lighting was provided with 1000 Watt metal halide lamps suspended as needed. The plants were used for testing when they reached the first to the fourth true leaf stage.
[00126] The treatments consisted of acid or acid esters
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70/84 of 4-amino-3-chloro-5-fluor-6- (4-chloro-2-fluor-3-methoxy-phenyl) pyridine-2-carboxylic (compound A) each formulated as a SC and several herbicidal components alone and in combination. Compound A forms were applied on an acid equivalent basis.
[00127] include: The forms of compound A (compound of Formula I) tested
OH
Compound A Acid
O
Compound A n-butyl ester
Compound A benzyl ester [00128] Other herbicidal components were applied on an active ingredient basis and included acetolactate synthase (ALS) inhibiting herbicides (chemical class of sulfonamide) penoxsulam formulated as Grasp ^® SC (GF-443), diclosulam formulated like Stron
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71/84 garm®, and chloransulam-methyl formulated as FirstRate®.
[00129] The treatment requirements for each compound or herbicidal component were calculated based on the rates being tested, the concentration of the active ingredient or acid equivalent in the formulation, an application volume of 2 mL per component per pot, and an application area of 86.59 cm ² per pot.
[00130] For formulated compounds, a measured amount was placed in an individual glass bottle of 100 or 200 mL and was dissolved in a volume of 1.25% (v / v) of Agri-Dex ^® culture oil concentrate to obtain each application solution. If the test compound did not dissolve easily, the mixture was heated and / or sonicated.
[00131] For technical grade compounds, a weighted amount can be placed in an individual 100 to 200 mL individual glass bottle and dissolved in a volume of acetone to obtain a concentrated stock solution. If the test compound does not dissolve easily, the mixture can be heated and / or sonicated. The concentrated stock solutions obtained can be diluted with an equivalent volume of an aqueous mixture containing 2.5% (v / v) of culture oil concentrate so that the final application solutions contain 1.25% (v / v) of culture oil concentrate.
[00132] The applications were made by injecting with a pipette appropriate amounts of the application solutions, individually and sequentially, in the aqueous layer of the rice field. Control plants were treated in the same way with the solvent blank. The applications were made so that all the material of the treated plant received the same concentrations of acetone and culture oil concentrate.
[00133] The treated plants and the control plants were placed in a greenhouse as described above and water was added with
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72/84 necessary to maintain a flood of the rice field. After approximately 3 weeks the condition of the test plants when compared to that of untreated plants was determined visually and recorded on a scale of 0 to 100 percent where 0 corresponds to no damage or inhibition of growth and 100 corresponds to complete death.
[00134] Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15: 20-22.).
[00135] 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) [00136] A = observed effectiveness of active ingredient A in the same concentration as used in the mixture.
[00137] B = observed effectiveness of active ingredient B at the same concentration as used in the mixture.
[00138] Some of the tested compounds, application rates used, plant species tested, and results are provided in tables 10 to 15.
TABLE 10. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A and Penoxsulam in Weed Control in a Rice Culture System.
Compound A Acid Penoxsulam Visual Weed Control (%) - 25 DAA LEFCH gae / ha gai / ha Note Esp 8.75 0 50 - 17.5 0 50 - 35 0 85 - 0 35 40 - 8.75 35 100 70
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Compound A Acid Penoxsulam Visual Weed Control (%) - 25 DAA LEFCH gae / ha gai / ha Note Esp 17.5 35 100 70 35 35 100 91
TABLE 11. Synergistic Activity of Water Applications of Compound A and Penoxsulam Benzyl Ester Herbicidal Compositions in Weed Control in a Rice Culture System.
Benzyl ester of Compound A Penoxsulam Visual Weed Control (%) - 25 DAA LEFCH gae / ha gai / ha Note Esp 8.75 0 50 - 17.5 0 90 - 0 17.5 0 - 0 35 40 - 8.75 17.5 90 50 17.5 17.5 99 90 8.75 35 100 70 17.5 35 100 94
Benzyl ester of Compound A Penoxsulam Visual Weed Control (%) - 21 DAA SCPMA gae / ha gai / ha Note Esp 48 0 0 - 96 0 0 - 0 10 70 - 0 20 88 - 0 40 95 - 48 10 75 70 96 10 90 70 48 20 85 88 96 20 100 88
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Benzyl ester of Compound A Penoxsulam Visual Weed Control (%) - 21 DAA SCPMA gae / ha gai / ha Note Esp 48 40 100 95 96 40 99 95
TABLE 12. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A and Diclosulam in the Control of Weeds Common to Rice Culture Systems.
Compound A Acid Diclosulam Visual Weed Control (%) - 21 DAA CYPRO gae / ha gai / ha Note Esp 8.75 0 0 - 0 6.62 80 - 0 13.25 80 - 8.75 6.62 100 80 8.75 13.25 95 80
TABLE 13. Synergistic Activity of Water Applications of Herbicidal Compositions of Benzyl Ester of Compound A and Diclosulam in the Control of Weeds Common to Rice Culture Systems.
Benzyl ester of Compound A Diclosulam Visual Weed Control (%) - 21 DAA ECHCG gae / ha gai / ha Note Esp 4.38 0 20 - 8.75 0 85 - 0 6.62 70 - 4.38 6.62 100 76 8.75 6.62 100 96
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TABLE 14. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A and Chloransulam-methyl in the Control of Weeds Common to Rice Culture Systems.
Compound A Acid Chloransulammethyl Visual Weed Control (%) - 22 DAA ECHCG gae / ha gai / ha Note Esp 16 0 20 - 32 0 25 - 0 17.5 50 - 16 17.5 75 60 32 17.5 75 63
Compound A Acid Chloransulammethyl Visual Weed Control (%) - 21 DAA CYPDI gae / ha gai / ha Note Esp 16 0 30 - 0 17.5 40 - 0 35 80 - 16 17.5 99 58 16 35 100 86
Compound A Acid Chloransulammethyl Visual Weed Control (%) - 21 DAA FIMMI gae / ha gai / ha Note Esp 16 0 20 - 32 0 20 - 0 17.5 40 - 0 35 60 - 16 17.5 100 52 32 17.5 100 52 16 35 75 68 32 35 90 68
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TABLE 15. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A Benzyl Ester and Chloransulammethyl in the Control of Weeds Common to Rice Culture Systems.
Benzyl ester of Compound A Chloransulammethyl Visual Weed Control (%) - 21 DAA FIMMI gae / ha gai / ha Note Esp 8 0 30 - 0 17.5 40 - 0 35 60 - 8 17.5 90 58 8 35 100 72
CYPDI Cyperus difformis L. ciperácea, junquinho
CYPRO Cyperus rotundus L. tiririca, purple
ECHCG Echinochloa crusgalli (L.) Beauv. rice grass
FIMMI Fimbristylis miliacea (L.) Vahl cuminho, globe
LEFCH Leptochloa chinensis (L.) Nees sprangletop, Chinese gae / ha = grams of acid equivalent per hectare gai / ha = grams of active ingredient per hectare
Obs = observed value
Esp = expected value as calculated by the Colby equation
DAA = days after application
Example III. Evaluation of Herbicidal Mixtures Applied Post Foliar Emergence for Weed Control in Cereal Cultures in the Greenhouse.
[00139] Seeds of the desired test plant species were planted in a Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm ² ). When necessary to ensure good germination and healthy plants, treatment with fungicide and / or
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77/84 another chemical or physical treatment was applied. The plants were grown for 7 to 36 days in a greenhouse with an approximate 14 hour photoperiod that was maintained at around 18 ° C during the day and around 17 ° C at night. Nutrients and water were added on a regular basis and supplementary lighting was provided with 1000 Watt metal halide lamps suspended as needed. The plants were used for the test when they reached the second or third stage of true leaf.
[00140] The treatments consisted of the benzyl ester of 4 amino-3- chloro-5- fluorine-6- (4-chloro-2-fluoro-3-methoxy-phenyl) pyridine-2-carboxylic acid (Compound A), formulated as a SC , a second cereal herbicide alone and then both in combination.
[00141] The forms of compound A (compound of Formula I) tested include:
Compound A benzyl ester [00142] Other herbicidal components were applied on an active ingredient basis and included acetolactate synthase (ALS) inhibiting herbicides (chemical class of sulfonamide) florasulam formulated as Derby ^® and piroxsulam formulated as PowerFlex ^® . A measured aliquot of 4-amino-3-chloro-5-fluor-6- (4-chloro-2-fluoro-3-methoxy-phenyl) pyridine-2-carboxylic acid benzyl ester (Compound A) was placed in glass vials 25 milliliter (mL) and diluted in a volume of 1.25% (v / v) of Agri-Dex ^® culture oil concentrate to obtain a stock solution. Compound requirements are substantiated
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78/84 at an application volume of 12 mL at a rate of 187 liters per hectare (L / ha). Spray solutions of the second cereal herbicide and experimental compound mixtures were prepared by adding the stock solutions to the appropriate amount of dilution solution to form 12 ml of spray solution with active ingredients in two- and three-way combinations. The formulated compounds were applied to the plant material with a suspended Mandel trail sprayer equipped with an 8002E nozzle calibrated to release 187 L / ha over an application area of 0.503 square meter (m ² ) at a spray height of 18 inches (46 cm) above the cover of the average plant. Control plants were sprayed in the same way with the blank solvent test.
[00143] 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 20 to 22 days, the condition of the test plants when compared to that of the control plants was determined visually and recorded on a scale of 0 to 100 percent where 0 corresponds to no damage and 100 corresponds to complete death.
[00144] Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15: 20-22.).
[00145] 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) [00146] A = observed effectiveness of active ingredient A in the same concentration as used in the mixture.
[00147] B = observed effectiveness of active ingredient B in the same
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[00148] The tested compounds, application rates used, tested plant species, and results are provided in tables 16 to 18.
TABLE 16. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Florasulam Applied to Leaves in Weed Control in a Cereal Culture System.
Application rate (gai / ha) SASKR VERPE VIOTR MATCH CIRAR Benzyl ester of Compound A Florasulam Note Esp Note Esp Note Esp Note Esp Note Esp 5 0 57 - 37 - 13 - 13 - 40 - 0 3.75 30 - 10 - 65 - 65 - 40 - 5 3.75 93 71 50 43 75 70 90 70 97 64
TABLE 17. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Florasulam Applied to Leaves in Weed Control in a Cereal Culture System.
Application rate (gai / ha) LAMP VERPE CIRAR Benzyl ester of Compound A Florasulam Note Esp Note Esp Note Esp 8.75 0.00 83 - 50 - 40 - 0 1.25 10 - 10 - 55 - 8.75 1.25 92 84 63 55 96 73
TABLE 18. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Piroxsulam Applied to Leaves in Weed Control in a Cereal Culture System.
Application rate (gai / ha) CIRAR Benzyl ester of Compound A Piroxsulam Note Esp 8.75 0.00 40 - 0 3.75 60 - 8.75 3.75 85 76
MATCH Chamomilla chamomilla (L.) Rydb. smelly chamomile, flavored
VERPE Veronica persica Poir. veronica,
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VIOTR Viola tricolor (L.) wild
CIRAR Cirsium arvense (L.) Scop.
SASKR Salsola iberica (L.)
LAMPU Lamium purpureum (L.) g / ha = grams per hectare
Obs = observed value pansy, thistle, Canada thistle, Russia lamio, purple
Esp = expected value as calculated by Colby equation
Example IV. Evaluation of Post-emergence and Injected Herbicidal Activity by Mixing Field Water.
[00149] Multiple post-emergence field experiments were conducted under field conditions in Tolima, Colombia; Thessaloniki, Greece; Ottobiano and Copiano, Italy; Greenville, MS and Eagle Lake, TX, USA; and water injected treatments were tested in Ryugasaki, Japan. Experiment sites were located in commercially cultivated cultivated rice (Oryza sativa) fields using the standard small herbicide batch survey methodology, except in Japan where the transplanted rice was used for the field experiment. The batch size of the post-emergence experiment ranged from 2 to 3 meters (m) x 5 to 8 m (width x length) with 4 replicates per treatment. The batch size of the water injection experiment was 2 x 2 m with 3 replicates per treatment. The rice crop was grown using normal cropping practices for fertilization, sowing, irrigation, flooding and maintenance to ensure the proper growth of the crop and weeds.
[00150] All treatments in the post-emergence field experiments were applied using a compressed air / gas backpack sprayer with nozzles with a flat propeller blade (80 ° or 110 °) calibrated to apply 187 to 300 L / ha of spray volume at nozzle pressure of approximately 200 to 400 kPa. In Japan,
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81/84 treatments were injected with water applied where the specific amount of commercial product was mixed in 100 mL of water per replica and applied directly in 3 cm of water depth containing the crop and weeds. The treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluorine-6- (4-chloro-2-fluorine-3-methoxyphenyl) pyridine-2-carboxylic acid (Compound A), formulated as a SC ( suspension concentrate), and various herbicidal components alone and in combination.
[00151] Forms of compound A (compound of Formula I) tested include:
Compound A benzyl ester [00152] The commercially available products of penoxsulam (Viper 20OD® (Europe), Grasp 240SC® (USA), and Wideattack 37.5SC® (Japan)) were mixed in water at formulated product rates appropriate for obtain the desired rates based on a unit area of application (hectare) to obtain the desired rates as shown. Treatments were classified 15 to 56 days after application (DAA) when compared to untreated control plants. Visual weed control was recorded on a scale from 0 to 100 percent where 0 corresponds to no damage and 100 corresponds to complete death.
[00153] All treatment results, both for the single product and for mixtures, are an average of 3 to 4 replicates. Experiment sites had populations of weeds occurring
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82/84 natural. The spectrum of weed included, but was not limited to, broadleaf papua (Brachiaria platyphylla (Griseb.) Nash or Urochloa platyphylla (Nash) RD Webster, BRAPP), junquinho (Cyperus difformis L., CYPDI), nuthatch (Cyperus esculentus L., CYPES), multiple Echinochloa species in the same field (ECHSS) in Italy (mixed ECHSS biotypes), Amazon sprangletop (Leptochloa panicoides (J. Presl) AS Hitchc., LEFPA), and Junquilho (Schoenoplectus juncoides (Roxb .) Palla, SCPJU).
[00154] The tested compounds, the application rates used, the plant species tested, and the results of field experiments in the culture are provided in tables 19 to 21.
TABLE 19. Synergistic Activity of Herbicidal Compositions of Compound A and Penoxsulam Benzyl Esters Applied to Leaves in Weed Control in a Rice Culture System when assessed 15 to 19 DAA (Days After Application) in the United States.
Benzyl ester of Compound A Penoxsulam Visual Weed Control (%) - 15 - 1 ' 9 DAA BRAPP LEFPA gae / ha gai / ha Note Esp Note Esp 24 0 - - 53 - 0 40 - - 16 - 24 40 - - 88 60 32 0 62 - - - 0 40 35 - - - 32 40 89 76 - -
TABLE 20. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Penoxsulam Applied to Leaves in Weed Control in a Rice Culture System when assessed 54 to 56 DAA (Days After Application) in Greece and Italy.
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Benzyl ester of Compound A Penoxsulam Visual Weed Control (%) - 54 - 56 DAA CYPDI CYPES ECHSS gae / ha gai / ha Note Esp Note Esp Note Esp 24 0 81 - 15 - 40 - 0 40 0 - 55 - 50 - 24 40 97 81 76 62 84 70
TABLE 21. Synergistic Activity of Water Applications of Herbicidal Compositions of Benzyl Compound A and Penoxsulam in Weed Control in a Rice Culture System when evaluated 28 DAA (Days After Application) in Japan.
Benzyl ester of Compound A Penoxsulam Visual Weed Control (%) - 28 DAA SCPJU gae / ha gai / ha Note Esp 150 0 22 - 0 50 20 - 150 50 60 38 200 0 25 - 0 50 20 - 200 50 68 42
BRAPP Brachiaria platyphylla (Griseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster Papua, broadleaf
LEFPA Leptochloa panicoides (Presl.) Hitchc. Amazon sprangletop ”
CYPDI Cyperus difformis L. junquinho, cipe- raca CYPES Cyperus esculentus L. yellow nuthatch ECHSS Echinochloa spp.SCPJU Schoenoplectus juncoides Roxb. Jonquil
gae / ha = grams of acid equivalent per hectare gai / ha = grams of active ingredient per hectare
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Obs = observed value
Esp = 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 of Formula (I) or a benzyl ester thereof, and (b) a triazolopyrimidine sulfonamide selected from chloransulam-methyl, diclosulam, flumetsulam or metosulam, where when (b) is chloransulam-methyl, the proportion in weight from (a) to (b) is 1: 2 to 10: 1, when (b) is diclosulam, the weight ratio from (a) to (b) from 1: 1.5 to 3: 1, when (a) is the benzyl ester of the compound of Formula (I) and (b) is flumetsulam, the weight ratio of (a) to (b) is from 1: 3 to 5: 1, when (a) is the ester benzyl of the compound of Formula (I) and (b) is metosulam, the weight ratio of (a) to (b) from 1.28: 1 to 5.1: 1.
[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.
[4]
4. Method to control undesirable vegetation, characterized by the fact that it comprises the stage of contacting a plant, the plant being the undesirable vegetation or the location of it, soil or
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2/3 water, the soil or water allowing the growth of undesirable vegetation, with a herbicidally effective amount of a composition, as defined in any one of claims 1 to 3.
[5]
5. Method, according to claim 4, characterized by the fact that undesirable vegetation is controlled in rice grown directly, irrigated and transplanted, cereals, wheat, barley, oats, rye, sorghum, maize / grain, cane -sugar, sunflower, rapeseed, canola, beet, soy, cotton, pineapple, pastures, lawns, pastures, fallow, peat, orchards and vineyards, aquatic plants, 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 pre-emergently to the plant or crop.
[7]
Method according to any one of claims 4 to 6, characterized in that the undesirable vegetation is controlled in glyphosate-tolerant cultures, 5-enolpyruvylxiquimate-3-phosphate (EPSP) synthase inhibitor, glufosinate, glutamine inhibitor synthetase, dicamba, phenoxy auxin, pyridyloxy auxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl CoA carboxylase inhibitor (ACCase), imidazolinone, sulfonyluria, pyrimidinyl thiozolinate, pyrimidinyl trioxide (ALS) or acetohydroxy synthase (AHAS), 4-hydroxyphenyl-pyruvate dioxigenase (HPPD) inhibitor, phyteno desaturase inhibitor, carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase (PPO) inhibitor, cellulose biosynthesis inhibitor, mitosis inhibitor, microtubule inhibitor, very long chain fatty acid inhibitor, bi inhibitor ossynthesis of fatty acid and lipid, photosystem I inhibitor, photosystem II inhibitor, triazine, or bromoxynil.
[8]
8. Method according to claim 7, characterized
Petition 870190006762, of 01/22/2019, p. 5/10
3/3 due to the fact that the tolerant crop has multiple or overlapping traits giving tolerance to multiple herbicides or multiple modes of action.
[9]
9. Method according to claims 4 to 8, characterized by the fact that the vegetation comprises a herbicide resistant or tolerant plant.

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IN2015DN01387A|2015-07-03|

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PE20191302A1|2019-09-23|

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ZA201501135B|2016-10-26|

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EP2877007A4|2016-03-09|

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法律状态:
2015-03-31| B03A| Publication of a patent application or of a certificate of addition of invention [chapter 3.1 patent gazette]|

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

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

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

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2019-04-09| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2019-06-18| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 22/07/2013, OBSERVADAS AS CONDICOES LEGAIS. (CO) 20 (VINTE) ANOS CONTADOS A PARTIR DE 22/07/2013, OBSERVADAS AS CONDICOES LEGAIS |

优先权:

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申请号 | 申请日 | 专利标题

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US201261675037P| true| 2012-07-24|2012-07-24|

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US61/675.037|2012-07-24|

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US13/832,978|US8906825B2|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 triazolopyrimidine sulfonamides|

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US13/832.978|2013-03-15|

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