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

专利摘要:
summary patent of the invention: "herbicide compositions comprising 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and herbicides synthetic auxin ". the present invention relates to herbicide compositions containing and methods for controlling undesirable vegetation using (a) a compound of formula (i): or an agriculturally acceptable salt or ester thereof and (b) a synthetic auxin herbicide, for example example, 2,4-d, aminocyclopyrachlor, aminopyralide, clomeprope-p, clopyralide, dicamba, dichlorprope-p, meptileptyl ester fluroxypyr (mhe), mcpa, mcpb, picloram, quincloraque, triclopir and halauxifene-methyl (4 Methyl 3-chloro-6- (4-chloro-2-fluoro-3-methoxyphenyl) picolinate) or an agriculturally acceptable salt or ester thereof. the compositions and methods provided here provide control of unwanted vegetation, for example, in no-till rice, sown in water and transplanted, cereals, wheat, barley, oats, rye, sorghum, corn, sugar cane, sunflower, rapeseed for seed oil, canola, sugar cane, soy, cotton, pineapple, pasture, grassland, pasture, fallowland, peat, tree and vine orchards, aquatic, plantation crops, vegetables, industrial vegetation treatment (ivm) or routes.
公开号:BR102013018684B1
申请号:R102013018684
申请日:2013-07-22
公开日:2020-02-04
发明作者:Yerkes Carla；Juras Len；Weimer Monte；Satchivi Norbert；Schmitzer Paul；Mann Richard；F Degenhardt Rory
申请人:Dow Agrosciences Llc；
IPC主号:

专利说明:

Invention Patent Descriptive Report for COMPOSITIONS OF HERBICIDES UNDERSTANDING ACID 4 AMINO-3-CHLORO-5-FLUOR-6- (4-CHLORINE-2-FLUORO-3METOXYPHENIL) PYRIDINE-2-CARBOXYLIC OR A DERIVATIVE FROM THE SAME AND HERBICIDES OF HERBINES , AND METHOD FOR CONTROL OF UNDESIRABLE VEGETATION.
Priority Claim [001] The present application claims the benefit of provisional patent application number US 61 / 675,070, filed on July 24, 2012, and patent application serial number US 13 / 833,923, filed on March 15, 2013 , whose report of each is incorporated here as a reference in its entirety.
Field [002] Herbicidal compositions comprising (a) 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or an ester or are provided herein agriculturally acceptable salt and (b) synthetic auxin herbicides.
[003] Unwanted vegetation control methods comprising application of (a) 4-amino-
3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic or an agriculturally acceptable ester or salt thereof and (b) a synthetic auxin herbicide or a salt or agriculturally acceptable ester thereof.
Background [004] The protection of crops against 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 a wide variety of chemical agents and chemical formulations effective in controlling such unwanted growth. Chemical herbicides
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2/202 of many types have been revealed in the literature and a large number are in commercial use. However, there remains a need for compositions and methods that are effective in controlling undesirable vegetation.
Summary [005] A first embodiment of the invention provided herein includes herbicidal compositions comprising a herbicidally effective amount of (a) a compound of Formula (I),
or an agriculturally acceptable salt or ester thereof, and (b) a synthetic auxin herbicide.
[006] A second embodiment includes mixing the first embodiment where 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, substituted benzyl, C1-4 alkyl and / or an n-butyl ester.
[007] A third modality includes the mixture according to the first or second modality where (b) at least one synthetic auxin herbicide is at least one compound selected from the group consisting of: 2,4-D, 2,4- D EHE, 2,4-DMA, 2,4-D choline, aminocyclopyrachlor, minopyralide, TIPA aminopyralide, clomeprope-P, clopyralide, MEA clopyralide, dicamba, DMA dicamba, dichlorprope-P, fluoxypyr, MHE fluoxipir, MCPA, EHE MCPA , MCPB, MCPB- ethyl ester, mecoprope-P, picloram, picloram K ⁺ salt, quinclorak, TEA
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3/202 ticlopyr, ticlopyr choline, ticlopir BEE, halauxifen-methyl, halauxifenomethyl (4-amino-3-chloro-6- (4-chloro-2-fluor-3-methoxyphenyl) picoline-to methyl) or its salt potassium carboxylate, or an agriculturally acceptable salt, ester or carboxylate salt thereof of at least one synthetic auxin herbicide mentioned above.
[008] A fourth modality includes mixtures according to any one of the first, second or third modality where the synthetic auxin herbicide in the mixture is 2,4-D, 2,4-D EHE, 2,4-DMA or 2 , 4-D choline where the weight ratio of the compound of Formula (I) to 2,4-D, 2,4-D EHE, 2,4-DMA or 2,4-D choline given in units of gae / ha for gai / ha or gae / ha for gae / ha is selected from the group of ratios of ratios and ratios consisting of 1: 128 to about 0.67: 1, 1:14 to about 14: 1, 1: 2, 1: 3.5, 1: 4, 1: 6, 1: 7, 1: 8, 1:11, 1:12, 1:14, 1:16, 1:17, 1:23, 1:24, 1: 28, 1:32, 1:45, 1:48, 1:55, 1:56, 1:64, 1:96, 1: 110, from 1:16 to 1:64, from 1: 3.5 to 1:28, from from 1: 8 to 1:64, from from 1: 2 to 1:16, from from 1:11 to 1:45, from from 1: 6 to 1:96, from from 1: 4 to 1:64, from from 1: 4 to 1:32, from from 1: 7 to 1:55, from from 1: 7 to 1:28, from 1:14 to 1: 110, from 1:28 to 1:56, from from 1: 2 to 1: 110, or within any r range defined between any pair of values above.
[009] A fifth modality includes mixtures according to any of the first, second or third modality where the synthetic auxin herbicide in the mixture is aminocyclopyrachlor where the weight ratio of the compound of Formula (I) to aminocyclopyrachlor given in gae units / ha to gai / ha or gae / ha to gae / ha is selected from the group of ratios of ratios and ratios consisting of: 1: 4 to about 2: 1, 1: 2 to about 1: 1, 1: 1 , 1: 2, 1: 4, from 1: 1 to 1: 4, or within the range defined between any pair of the above values.
[0010] A sixth modality includes mixtures according to either a first, second or third modality where the
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4/202 synthetic auxin herbicide in the mixture is aminopyralide or TIPA aminopyralide where the weight ratio of the compound of Formula (I) to aminopyralide or TYPE aminopyralide given in units of gae / ha to gai / ha or gae / ha to gae / ha is selected from the group of ratios and ratios consisting of: from about 1:23 to about 1: 4, from about 1:16 to about 1: 6, 1: 4, 1 : 5,7, 1: 8, 1:16, from 1: 4 to 1:16 or within any defined range between any pair of values above.
[0011] A seventh embodiment includes mixtures according to any one of the first, second or third modality where the synthetic auxin herbicide in the mixture is clomeprope-P having a weight ratio of the compound of Formula (I) or salt or ester of the even for clomeprope-P or salt or ester thereof within the range of from 1: 159 to about 1: 1 or about 1: 200 to about 6: 1.
[0012] An eighth modality includes mixtures according to any of the first, second or third modality where the synthetic auxin herbicide in the mixture is clopyralide or MEA clopyralide where the weight ratio of the compound of Formula (I) to clopyralide or MEA clopyralide 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 1:23 to about 1: 4, from from about 1:16 to about 1: 6, 1: 4, 1: 5,7, 1: 8, 1:16, from from 1: 4 to 1:16 or within any defined range between any pair of the above values.
[0013] A ninth modality includes mixtures according to any one of the first, second or third modality where the synthetic auxin herbicide in the mixture is dicamba or DMA dicamba where the weight ratio of the compound of Formula (I) to dicamba or DMA dicamba given in units of gae / ha to gai / ha or gae / ha to gae / ha is selected from the group of ranges of reasons and reasons
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5/202 consisting of: from about 1: 255 to about 1.2: 1, from about 1:31 to about 1: 7, 1: 3.3, 1: 4, 1: 6,6, 1: 8, 1:11, 1:16, 1:26, 1:45, 1:53, 1:64, from from 1:26 to 1:53, from from 1: 8 to 1:64, from from 1: 3.3 to 1:26, from from 1:11 to 1:45, from from 1: 3.3 to 1:64 or within any range defined between any pair of the above values.
[0014] A tenth modality includes mixtures according to any of the first, second or third modality where the synthetic auxin herbicide in the mixture is dicloprope-P where the weight ratio of the compound of Formula (I) to dicloprope-P 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: 1:16, from about 1: 4 to about 1:64 , 1:32.
[0015] An eleventh modality includes mixtures according to the first, second or third modality where the synthetic auxin herbicide in the mixture is fluroxypyr or MHE fluroxypyr where the weight ratio of the compound of Formula (I) to fluroxypyr or MHE fluroxypyr given in units of gae / ha to gai / ha or gae / ha to ga / ha is selected from the group of ratios of ratios and ratios consisting of: from about 1: 127 to about 2: 1, from a from 1:16 to about 1: 4,38, 1: 2, 1: 3,6, 1: 4, 1: 8, 1: 9, 1:14, 1:16, 1:18, 1: 32, 1:35, from from 1: 2 to 1:32, from from 1: 2 to 1:16, from from 1: 4 to 1:35, from from 1:36 to 1:64, from 1: 8 to 1:32, from 1: 4.4 to 1:64, from 1: 2 to 1:35 or within any defined range between any pair of the above values.
[0016] A twelfth modality includes mixtures according to any of the first, second or third modality where the synthetic auxin herbicide in the mixture is MCPA or MCPA EHE where the weight ratio of the compound of Formula (I) to MCPA or MCPA EHEDed in units of gae / ha for gai / ha or gae / ha for
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6/202 gae / ha is selected from the group of ratios and ratios consisting of: from about 1:64 to about 0.6: 1, from about 1:16 to about 1 : 7, 1: 2, 1: 2,2; 1: 4, 1: 4,4, 1: 6,6, 1: 8, 1: 8,8, 1:11, 1:16, 1: 17,5, 1:32, 1:35, from to from 1: 2 to 1:16, from from 1: 5.7 to 1:32, from from 1: 8 to 1:32, from from 1: 2.2 to 1:35, from 1: 2 to 1:35 or within any defined range between any pair of the above values.
[0017] A thirteenth modality includes mixtures according to any of the first, second or third modality where the synthetic auxin herbicide in the mixture is MCPB or salt or ester where the weight ratio of the compound of Formula (I) to MCPB given in units of gae / ha to gai / ha or gae / ha to gae / ha is selected from the group of ranges and ratios and ratios consisting of: from about 1: 250 to about 3: 1, from to from about 1: 150 to about 0.75: 1 or within any defined range between any pair of the above values.
[0018] A fourteenth includes mixtures according to any of the first, second or third modality where the synthetic auxin herbicide in the mixture and mecroprope-P where the weight ratio of the compound of Formula (I) to mecoprope-P 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 1:20 to about 1:20 to about 1 : 60, from about 1:40 to about 1: 100.
[0019] A fifteenth modality includes mixtures according to any of the first, second or third modality where the synthetic auxin herbicide in the mixture is picloram or picloram K + salt where the weight ratio of the compound of Formula (I) to picloram or picloram K + salt given in units of gae / ha to gai / ha or gae / ha to gae / ha is selected from the group of ranges of reasons and reasons
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7/202 consisting of: from about 1:16 to about 1.75: 1, from about 0.44: 1 to about 1: 4, 1: 1.1, 1: 2, 1: 4, 1: 8, 1:16, from 1: 2 to 1:16, from 1: 1.1 to 1:16 or within any defined range between any pair of values above.
[0020] A sixteenth modality includes mixtures according to any one of the first, second or third modality where the synthetic auxin herbicide in the mixture is quinclorak, where the weight ratio of the compound of Formula (I) to quincloraque given in units 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: 128 to about 1.2: 1, from from about 1:16 to about 1: 6.5, 1: 1.7, 1: 2, 1: 3, 1: 4, 1: 7, 1:13, 1:16, 1:18, 1 : 26, 1:32, 1:35, 1:64, 1:70, 1: 128, from 1: 9 to 1:70, from 1: 3 to 1: 128, from from 1:16 to 1:64, from from 1: 7 to 1:13, from from 1: 7 to 1:64, from from 1: 8 to 1:64, from from 1 : 4 to 1:16, from 1: 2 to 1: 128, from 1: 1.7 to 1:32, from 1: 1.7 to 1:16 or within any defined range between any pair of values above. [0021] A seventeenth modality includes mixtures according to any of the first, second or third modality where the synthetic auxin herbicide in the mixture is triclopyr, TEA triclopyr, triclopyr choline or BEE triclopyr, where the weight ratio of the compound of Formula (I) for triclopyr, TEA triclopyr, triclopyr choline or BEE triclopyr given in units of gae / ha to gai / ha or gae / ha to gae / ha is selected from the group of ranges of reasons and reasons consisting of: from to from about 1:64 to about 1.2: 1, from about 1: 8 to about 1: 6.6, 1: 1.7, 1: 2, 1: 3.3, 1 : 4, 1: 5, 1: 5,6, 1: 6,6, 1: 8, 1:11, 1:13, 1:14, 1:16, 1:22, 1: 17,5, 1 : 22, 1:26, 1:32, 1:45, from 1: 5 to 1:45, from from 1:11 to 1:45, from from 1: 2 to 1:16 from 1: 2 to 1:32, from 1: 4 to 1:32, from 1: 1.7 to 1:26, from 1: 1.7 to 1 : 13, from 1: 7 to 1:45 or within any range
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8/202 defined between any pair of values above.
[0022] An eighteenth modality includes mixtures according to any one of the first, second or third modality where the synthetic auxin herbicide in the mixture is halauxifene-methyl (4-amino-3 chloro-6- (4-chloro-2- fluorine-3-methoxyphenyl) methyl picolinate) or its potassium carboxylate salt where the weight ratio of the compound of Formula (I) to halauxifene-methyl (4-amino-3-chloro-6- (4-chloro-2- fluorine-3methoxyphenyl) methyl picolinate) or its potassium carboxylate salt is given in units of gae / ha for gai / ha or gae / ha for gae / ha is selected from the group of ranges of reasons and reasons consisting of: from to from about 1: 2 to about 20: 1, from about 2: 1 to about 5: 1, 1: 4, 1: 2, 1.2: 1, 1: 1.2: 1 , 2,4: 1,4: 1,5: 1,8: 1, 10: 1 from 1: 2 to 4: 1, from 1: 1 to 8: 1, from 1.2: 1 to 10: 1, from 1: 4 to 4: 1, from 1: 4 to 10: 1 or within any defined range between any pair of the above values.
[0023] A nineteenth modality includes any composition according to any of the first to seventh modalities where the mixture further comprises at least one of an agriculturally acceptable agent selected from the group consisting of an adjuvant, a vehicle or a protector.
[0024] A twentieth modality includes methods of controlling undesirable vegetation comprising the application step or otherwise contacting the vegetation and / or soil and / or water with a herbicidally effective amount of at least one mixture containing any of the first to tenth eighth modalities.
[0025] A twenty-first modality includes methods according to the twentieth modality where the method is practiced in at least one member of the group consisting of direct sown rice, sown in water and / or transplanted, cereals, wheat, barley, oats, rye , sorghum, corn, sugar cane, sunflower, oilseed rape seed,
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9/202 canola, sugar beet, soy, cotton, pineapple, grass for grass, grassland, pasture, fallowland, peat, tree and vine orchard, aquatic, plantation crops, vegetables, industrial vegetation care (IVM) (Industrial Vegetation Management) or rights of way (ROW - Rights-Of-Way).
[0026] A twenty-second modality includes methods according to any of the twelfth and twenty-first modalities where the herbicidally effective amount of the mixture is applied either pre- or post-emergently to at least one of the following: a crop, a field , a ROW or a rice paddy.
[0027] A twenty-third modality includes methods according to any of the twelfth through twenty-second modalities where the undesired vegetation can be controlled in: glyphosate-tolerant crops, 5-enolpyruvylchiquimate-3-phosphate (EPSP) synthase, glufosinate, glutamine synthetase inhibitor, dicamba, phenoxy auxin, pyridyloxy auxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl CoA carboxylase inhibitor (ACCase), imidazolinone, sulfonylone, sulfonylamine, trioxide, sulfonylamine, trioxide synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor, 4-hydroxyphenyl-pyruvate dioxigenase (HPPD) inhibitor, phytene desaturase inhibitor, carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase (PPO) inhibitor, cellulose biosynthesis inhibitor, cellulose biosynthesis inhibitor mitosis, microtubule inhibitor, inhibitor of very long chain fatty acid, inhibitor of biosynthesis of fatty acid and lipid, inhibitor of photosystem I, inhibitor of photosystem II, protoporphyrinogen oxidase (PPO) inhibitor, triazine or bromoxynil.
[0028] A twenty-fourth modality includes at least one method according to any of the twenty-twenty-third
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10/202 modalities where a plant that is resistant or tolerant to at least one herbicide is treated and where the resistant or tolerant culture has multiple or stacked characteristics that confer tolerance to multiple herbicides or inhibitors of multiple modes of action, in some modalities the plant treated that expresses resistance or tolerance to herbicide is undesirable vegetation in itself. [0029] A twenty-fifth modality includes methods according to the twenty-fourth modality, where the resistant or tolerant weed is a biotype with resistance or tolerance to multiple herbicides, multiple chemical classes, multiple herbicide mode-of-deation inhibitors or through multiple resistance mechanisms. [0030] A twenty-sixth modality includes at least one of the methods according to or with the twenty-fourth or twenty-fifth modality, where the resistant or tolerant undesirable plant is a resistant or tolerant biotype to at least one agent selected from the group consisting of: inhibitors acetolactate synthase (ALS) or acetohydroxy acid synthase (HAS), photosystem II inhibitors, acetyl CoA carboxylase inhibitors (ACCase), synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5enolpyruvylchiquite-3-phosphate inhibitors ( EPSP) synthase, microtubule assembly inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid inhibitors (VLCFA), phytene desaturase inhibitors ( PDS), glutamine synthetase inhibitors, 4-hydroxyphenylpyruvate-dioxigenase (HPPD) inhibitors, mitosis inhibitors, inhibitor s from cellulose biosynthesis, herbicides with multiple modes of action, quinclorak, arylaminopropionic acids, difenzoquate, endothal or organoarsenic acids.
[0031] A twenty-seventh modality includes methods of controlling undesirable vegetation comprising the stage of applying a
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11/202 herbicidally effective amount of at least one mixture according to the fourth modality where the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha, of 2,4-D, 2,4-D EHE, 2,4-DMA or 2,4-D hill selected from the group of bands and bands of classes consisting of about: 35, 50, 52.5, 70, 105, 140, 150, 210, 240, 280, 420, 480, from from 70 to 280, from from 105 to 420, from from 52.5 to 105, from from 240 to 480, from from 35 to 70, from from 35 to 480 or within any defined range between any pair of the above values.
[0032] A twenty-eighth modality includes methods according to any one fourth and twenty-sixth modalities where the controlled plant is at least one plant selected from the group consisting of: ECHCG, DIGSA, ECHCO, CYPES, CYPIR, BRAPP, LEFCH, ECHOR, CYPRO, SCPJU, SCPMA, PANDI, ELEIN, CENMA, PANMI, POLCO, SINAR, SONAR, SORHA, CASOB, yet other modalities include plant control of the genera consisting of: Echinochloa, Digitaria, Cyperus, Brachiaria, Urochloa, Leptochloa, Schoenop, Schoenop, Schoenoplactus, Panicum, Polygonum, Sinapis, Sonchus, Sorghum and Cassia.
[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 fifth modality where the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of aminocyclopyrachlor selected from the group of rates and class ranges consisting of, approximately: 8.75, 17.5, from 8.75 to 17.5 or within any defined range between any pair of above values.
[0034] A thirtieth modality includes methods according to any of the fifth and twenty-ninth modalities where the controlled plant is at least one plant selected from the group consisting of
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12/202 in: TRFRE, SINAR, CENMA, yet other modalities include plant controls of the genres consisting of: Trifolium, Sinapis and Centaurea.
[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 sixth modality where the amount of the mixture is applied at a rate expressed in gai / ha or gae / ha of aminopyralide or TYPE aminopyralide selected from the group of rates and rate ranges consisting of about: 3, 17.5, 35, from 17.5 to 35 or within any defined range between any pair of above values.
[0036] A thirty-second modality includes methods according to any of the sixth and thirty-first modalities where the controlled plant is at least one plant selected from the group consisting of: POLCO, CIRAR, BRSNN, TRFRE, SINAR, SOOSS, yet other modalities include control of plants of the genera consisting of: Polygonum, Cirsium, Brassica, Trifolium, Sinapis and Solidago.
[0037] A thirty-third modality includes methods of controlling unwanted vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the seventh modality where the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha, from PomepropeP selected from the group of rates or rate ranges consisting of about: 50 gae / ha to about 400 gae / ha or within any range defined between any pair of the above values.
[0038] A thirty-fourth 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 where the amount of the mixture is
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13/202 applied at a rate expressed in gai / ha or gae / ha of clopyralide or MEA clopyralide selected from the group of rates of rate ranges consisting of about 35, 50, from 35 to 50 or within any range defined between any pair of the above values.
[0039] A thirty-fifth modality includes methods according to any of the eighth and thirty-fourth modalities where the controlled plant is at least one plant selected from the group consisting of: AMARE, CIRAR, SOOS, yet other modalities include control of plants of the genera consisting of: Amaranthus, Cirsium and Solidago.
[0040] A thirty-sixth 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 where the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of dicamba or dicamba DMA selected from the group of rates and rate ranges consisting of about: 35, 50, 70, 140, 280, from 140 to 280, from 35 to 280 or within any defined range between any pair of the above values.
[0041] A thirty-seventh modality includes methods according to any of the ninth and thirty-sixth modalities where the controlled plant is at least one plant selected from the group consisting of: AMARE, POLCO, BRSNN, LEFCH, CYPIR, ECHCO, ECHCG, ECHOR , SCPMA, SIDSP, SINAR, CASOB, yet other modalities include control of plants of the genres consisting of: Amaranthus, Polygonum, Brassica, Leptochloa, Cyperus, Echinochloa, Schoenoplectus, Bolboschoenus, Sida, Sinapis and Cassia.
[0042] A thirty-eighth modality includes methods of controlling unwanted vegetation comprising the step of applying a herbicidally effective amount of at least a mixture of
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14/202 according to the tenth modality where the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha, of dichlorprope-P selected from the group of rates and rate ranges consisting of about 70, 140, 280 and 1,120 or within any defined range between any pair of the above values.
[0043] A thirty-ninth modality includes methods according to any of the tenth and thirty-eighth modalities where the controlled plant is at least one plant selected from the group consisting of: VIOTR, BRSNN, yet other modalities include control of plants of the genera consisting of : Viola and Brassica.
[0044] A fortieth modality includes methods of controlling unwanted vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the eleventh modality where the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha of fluroxypyr or MHE fluroxypir selected from the group of rates and rate ranges consisting of: 35, 70, 140, 149, 280, from 70 to 280, from 35 to 280 or within any range defined between any pair of the above values.
[0045] A forty-first modality includes methods according to any of the eleventh and fortieth modalities where the controlled plant is at least one plant selected from the group consisting of CENMA, SONAR, TRFRE, SOOSS, ECHCG, ECHCO, CYPDI, LEFCH, ECHOR, SCPJU, AMARE, SCPMA, VIOTR, POLCO, CIRAR and SASKR, yet other modalities include control of plants of the genres consisting of: Centaurea, Sonchus, Trifolium, Solidago, Echinochloa, Cyperus, Leptochloa, Schoenoplectus, Viola, Polygonum, Salola Cirsium.
[0046] A forty-second modality includes methods of controlling undesirable vegetation comprising the application stage
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15/202 of a herbicidally effective amount of at least one mixture according to the twelfth modality where the amount of the mixture is applied at a rate, expressed in gai / ha or gae / ha, of MCPA or MCPA EHEis selected from the group of rates and rate ranges consisting of about: 50, 70, 140, 280, from 50 to 140, from 70 to 140, from 50 to 280, from 70 to 280 or within any defined range between any pair of the above values. [0047] A forty-third modality includes methods according to any of the twelfth and forty-second modalities where the controlled plant is at least one plant selected from the group consisting of BRAPP, DIGSA, ECHCG, ECHOR, LEFCH, SCPJU, VIOTR, POLCO , BRSNN and in still other modalities includes control of plants of the genera consisting of: Brachiaria, Digitaria, Echinochloa, Viola, Polygonum, Brassica, Leptochloa and Schoenoplectus.
[0048] A forty-four modality includes methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the thirteenth modality where the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha, of mecroprope-P selected from the group of rates and rate ranges consisting of about: 50, 100, 200, 400 and 1,000 or within any range defined between any pair of the above values.
[0049] A forty-fifth modality includes methods according to any of the thirteenth and forty-fourth modalities where the controlled plant is at least one plant selected from the group consisting of: BRSNN, yet other modalities include control of plants of the genres consisting of: Brassica.
[0050] A forty-sixth modality includes methods of
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16/202 control of undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the fourteenth modality where the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha, picloram or picloram K + salt selected from the group of rates or rate ranges consisting of about: 10, 35, 70, from 35 to 70 or within any defined range between any pair of the above values. [0051] A forty-seventh modality includes methods according to any of the fourteenth and forty-sixth modalities where the controlled plant is at least one plant selected from the group consisting of: VIOTR, STEME, POLCO, CENMA, SINAR, yet other modalities include control of plants of the genera consisting of: Viola, Stellaria, Polygonum, Centaurea and Sinapis.
[0052] A forty-eighth modality includes methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the fifteenth modality where the amount of the mixture is applied in a rate, expressed in gai / ha or gae / ha, quincloraque selected from the group of rates and rate ranges consisting of about: 70, 140, 280, 560, from 70 to 560 or within any range defined between any pair of the above values . [0053] A forty-ninth modality includes methods according to any of the fifteenth and forty-eighth modalities where the controlled plant is at least one plant selected from the group consisting of: AMARE, VIOTR, ECHOR, SCPMA, POLCO, CYPES, DIGSA, CYPIR, ECHCG, ISCRU, yet other modalities include control of plants of the genera consisting of: Amaranthus, Viola, Echinochloa, Schoenoplectus, Bolboschoenus, Polygonum, Cyperus, Digitaria and Ischaemum.
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17/202 [0054] A fiftieth modality includes methods of controlling unwanted vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the sixteenth modality where the amount of the mixture is applied at a rate, expressed in gai / ha or gae / ha, of triclopyr, TEA triclopyr, triclopyr choline or triclopir BEE selected from the group of rates and rate ranges consisting of about: 35, 50, 70, 98.3, 140, 196.6, 280, from 35 to 140, from 98.3 to 280, from 70 to 280 from 70 to 140, from 35 to 280 or within any defined range between any together with the above values
[0055] A fifty-first modality includes methods according to any of the sixteenth and forty-ninth modalities where the controlled plant is at least one plant selected from the group consisting of BRAPP, SCPJU, DIGSA, ECHOR, ECHCG, SCPMA, ECHCO, LEFCH , CENMA, SONAR, CIRAR, CASOB, yet other modalities include control of plants of the genera consisting of: Brachiaria, Schoenoplectus, Digitaria, Echinochloa, Bolboschoenus, Leptochloa, Centaurea, Sonchus, Cirsium and Cassia.
[0056] A fifty-second modality includes methods of controlling undesirable vegetation comprising the step of applying a herbicidally effective amount of at least one mixture according to the seventeenth modality where the amount of the mixture is applied at a rate, expressed in gai / ha or gae / ha of halauxifene- (methyl 4-amino-3-chloro-6- (4-chloro-2-fluoro-3methoxyphenyl) methyl picolinate) or its carboxylate salt selected from the group of rates and rate ranges consisting of about: 2.19, 3.75, 4.38, 7.5, 8.75, 15, from 2.19 to 4.38, from 4.38 to 8.75 , from 3.75 to 15, from 2.19 to 15 or within any defined range between any pair of the above values.
[0057] A fifty-third modality includes methods of
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18/202 according to any of the seventeenth and fifty-second modalities where the controlled plant is at least one plant selected from the group consisting of LEFCH, IPOHE, CYPIR, ECHCG, ECHOR, CYPRO, SORHA, ELEIN and KCHSC, yet other modalities include control of plants of the genera consisting of: Leptochloa, Ipomoea, Cyperus, Echinochloa, Sorghum, Eleusine and Kochia.
[0058] A fifty-fourth modality includes compositions according to any of the first to third modalities, where (b) is aminocyclopyrachlor.
[0059] A fifty-fifth modality includes compositions according to any of the first to third modalities, where (b) is aminopyralide or TIPA aminopyralide.
[0060] A fifty-sixth modality includes compositions according to any of the first to third modalities, where (b) is clomeprope-P.
[0061] A fifty-seventh embodiment includes compositions according to any of the first to third embodiments, where (b) is clopyralide or MEA clopyralide.
[0062] A fifty-eighth modality includes compositions according to any of the first to third modalities, where (b) is dicamba or DMA dicamba.
[0063] A fifty-ninth modality includes compositions according to any of the first to third modalities, where (b) is dicloprope-P.
[0064] A sixtieth modality includes compositions according to any of the first to third modalities, where (b) is fluroxypyr or MHE fluroxypyr.
[0065] A sixty-first modality includes compositions according to any of the first to third modalities, where (b)
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19/202 is MCPA or EHE MCPA.
[0066] A sixty-second modality includes compositions according to any of the first to third modalities, where (b) is MCPB or MCPB ethyl ester.
[0067] A sixty-third modality includes compositions according to any of the first to third modalities, where (b) is mecoprope-P.
[0068] A sixty-fourth modality includes compositions according to any of the first to third modalities, where (b) is picloram or picloram salt K +.
[0069] A sixty-fifth modality includes compositions according to any of the first to third modalities, where (b) is quincloraque.
[0070] A sixty-sixth modality includes compositions according to any of the first to third modalities, where (b) is triclopyr, TEA triclopyr, triclopyr choline or BEE triclopir.
[0071] A sixty-seventh modality includes compositions according to any of the first to third modalities, where (b) is halauxifene-methyl (4-amino-3-chloro-6- (4-chloro-2-fluor-3-methoxyphenyl) methyl picolinate) or its potassium carboxylate salt.
[0072] A sixty-eighth modality includes methods according to any of the twenty-fifth to fifty-third modalities, where the unwanted vegetation is immature.
[0073] A sixty-ninth modality includes methods according to any of the twenty-fifth to fifty-third or sixty-eighth modalities where the composition is applied to water that is part of a flooded rice field.
[0074] Herbicidal compositions comprising a herbicidally effective amount (a) of a compound of Formula (I) are provided herein
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20/202
h ₃ c '° ® or an agriculturally acceptable salt or ester thereof and (b) a synthetic auxin herbicide. The compositions can also contain an agriculturally acceptable adjuvant or vehicle.
[0075] Unwanted vegetation control methods comprising application of (a) a compound of Formula (I) or an agriculturally acceptable ester or salt and (b) a synthetic auxin herbicide or an agriculturally salt or ester are also provided here acceptable value.
Detailed Description
DEFINITIONS [0076] As used herein, the compound of Formula (I) has the following structure:
[0077] The compound of Formula (I) can be identified by the name 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methoxyphenyl) -5-fluorpiridine-2-carboxylic acid and has been described in the Patent US 7,314,849 (B2), which is incorporated herein by reference in its entirety. Exemplary uses of the compound of Formula (I) include control of undesirable vegetation, including grass, broadleaf weeds and sedge, in non-crop and multiple crop situations.
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21/202 [0078] Without being limited by any theory, synthetic auxin herbicides are a class of herbicides that generally mimic auxin, a plant growth hormone. They are often called growth regulators because they upset the natural hormone balance in the plant. Exemplary synthetic auxin herbicides include, but are not limited to, 2,4-D, 4-DB, aminocyclopyrachlor, aminopyralide, clomeprope-P, clopyralide, dicamba, dichlorprope-P, meptileptyl ester fluroxypir (MHE), MCPA, MCPB , mecoprope-P, picloram, quincloraque, triclopir and halauxifeno-methyl (4 amino-3- chloro-6- (4-chloro-2-fluoro-3-methoxyphenyl) methyl picolinate) or an agriculturally acceptable salt or ester thereof.
[0079] As used herein, 2,4-D is 2- (2,4dichlorophenoxy) acetic acid and has the following structure:
OH
Cl
Cl [0080] Use of exemplary 2,4-D are described 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 2,4-D include its use for post-emergence control of annual and perennial broadleaf weeds, for example, in cereals, corn, sorghum, prairie, established peat, grass seed crops, orchards, cranberries , asparagus, sugar cane, rice forestry and non-culture field. Exemplary chemical forms of 2,4-D include salt or ester forms, for example, 2,4-D EHE, which is 2- (2,4-dichlorophenoxy) 2-ethylhexyl acetate and has the following structure:
C1
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22/202 [0081] 2,4-D DMA, which is 2- (2,4-dichlorophenoxy) acetic acid with Nmethylmethanamine and has the following structure:
[0082] 2,4-D DMA, which is 2- (2,4-dichlorophenoxy) acetic acid with Nmethylmethanamine and has the following structure:
, CH ₃ h ₂ n ³ ch ₃ [0083] 2,4-D choline, which is 2-, 2,4-dichlorophenoxy) 2-hydroxyN, N, N-trimethylethanamine acetate and has the following structure:
Cl
HO
Cl
CH, i, -Ch ₃
NÚ ^ch 3; and [0084] 2,4-DB, which is 2- (2,4-dichlorophenoxy) butyric acid and has the following structure:
O
Cl
Cl [0085] As used herein, aminocyclopyrachlor is 6-amino-5-chloro-2-cyclopropyl-4-pyrimidine carboxylic acid and has the following structure:
[0086] Exemplary uses of aminocyclopyrachlor are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of aminocyclopyrachlor include its use for weed control of
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23/202 broad leaf and trunk species, for example, on paths, industrial sites, pastures, permanent grass pastures and natural areas. [0087] As used herein, aminopyralide is 4-amino-3,6dichloro-2-pyridinecarboxylic acid and has the following structure:
ci .0
Cl OH [0088] Exemplary uses of aminopyralide are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of aminopyralide include its use for long-term control of annual and perennial broadleaf weeds, for example, in pastures and pasture. Exemplary chemical forms of aminopyralide include, for example, TIPA aminopyralide, which is composed of 4 'amino-3,6dichloropyridine-2-carboxylic acid with 1,1', 1-nitrilotris [2-propanol] and has the following structure:
ci ch
CH3 [0089] As used herein, clomeprope-P is 2- (2,4-dichloro-3methylphenoxy) -N-phenylpropanamide and has the following structure:
Cl [0090] Exemplary uses of clomeprope-P are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of clomeprope include its use for pre- and post-emergence control of broadleaf and cyperaceous weeds, for example, in rice field.
[0091] As used herein, clopyralide is 3,6-dichloro-2 acid
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24/202 pyridinocarboxylic and has the following structure:
O
Cl
OH
Cl [0092] Exemplary uses of clopyralide are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of clopyralide include its use for post-emergence control of many annual and perennial broadleaf weeds, for example, in beets. sugar, fodder beet, oilseed rape, corn, cereals, brassicas, onions, leeks, strawberries and hemp, and in prairie and non-crop fields. Exemplary chemical forms of clopyralide include, for example, clopyralide MEA, which is 3,6dichloro-2-pyridinecarboxylic acid with 2-aminoethanol and has the following structure:
O
Cl
° 'ha
OH ci [0093] As used here, dicamba is 3,6-dichloro-2methoxybenzoic acid and has the following structure:
C1
Cl
OH h ₃ C '[0094] Exemplary uses of dicamba are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of dicamba include its use for controlling annual and perennial broadleaf weeds and shrub species, for example , in cereals, corn, sorghum, sugar cane, asparagus, perennial seed grasses, peat, pastures, pastures and non-crop fields. Exemplary chemical forms of dicamba include, for example, dicamba DMA, which is
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25/202 3,6-dichloro-2-methoxybenzoic acid compound with N-methylmentanamine and has the following structure:
[0095] As used herein, dichlorprope-P is (2R) -2- (2,4dichlorophenoxy) propanoic acid and has the following structure:
O
[0096] Exemplary uses of dichlorprope-P are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of dichlorprope-P include its use for post-emergence control of broadleaf weeds, for example, in cereals.
[0097] As used herein, fluroxypyr is 2 - [(4-amino-3,5dichloro-6-fluor-2-pyridinyl) oxide] acetic acid and has the following structure:
F
Cl O [0098] Exemplary uses of fluroxypyr are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of fluroxypyr include its use for post-emergence foliar application to control broadleaf weeds, for example, in grain crops small, control of Rumex spp. and Urtilca dioica in pastures and control of Trifolium repens in grasses amenity. Other exemplary uses include its use to control herbaceous and stem broadleaf weeds, for example, in orchards and plantation crops, and broadleaf shrubs, for example, in coniferous forests. Shapes
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26/202 exemplary chemicals fluroxypyr include, for example, MHE fluroxypyr, which is 2 - [(4-amino-3,5-dichloro-6-fluor-2-pyridinyl) oxy] 1-methylptyl acetate and has the following structure:
F
Cl o ch ₃ [0099] As used herein, MCPA is 2- (4-chloro-2 methylphenoxy) acetic acid and has the following structure:
[00100] Exemplary uses of MCPA are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of MCPA include its use for post-emergence control of annual and perennial broadleaf weeds, for example, in seed crops grass, hemp, rice, vines, peas, potatoes, asparagus, grasslands, peat, low fruit trees and roadside boundaries and embankments. Other exemplary uses include its use to control broadleaf and trunk weeds, for example, in the forest, as well as aquatic broadleaf weeds. Exemplary chemical forms of MCPA include, for example, MCPA EHE is 2- (4-chloro-2methylphenoxy) 2-ethylhexyl acetate and has the following structure:
[00101] As used herein, MCPB is 4- (4-chloro-2 methylphenoxy) butanoic acid and has the following structure:
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27/202
[00102] Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. It can be used in field peas to control Canada's thistle and control or suppress certain annual broadleaf weeds including lambsquarter, fedegosa ( pigweed spp.), persicaria (smartweed spp). and morning primrose (morningglory spp).
[00103] As used here, MCPB-sodium is 4- (4-chloro-otolyloxy) butanoate and has the following structure:
[00104] Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of MCPB-sodium include post-emergence control of annual and perennial broadleaf weeds in cereals, clovers, sanfene, peas, and peanuts prairie, as well as broadleaf and trunk weed control in the forest.
[00105] As used herein, MPCB-ethyl ester is 4- (4-chloro-2methylphenoxy) butanoate and has the following structure:
[00106] Its herbicidal activity is exemplified in The Pesticide
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28/202
Manual, Fifteenth Edition, 2009. Exemplary uses of MCPB-ethyl ester include broadleaf weed control in paddy fields.
[00107] As used herein, mecoprope-P is (2R) -2- (4-chloro-
2-methylphenoxy) propanoic and has the following structure:
O
[00108] Exemplary uses of mecoprope-P are described in The Pesticide Manual, Fifteenth edition, 2009. Exemplary uses of Mecoprope-P include its use for post-emergence control of broadleaf weeds, for example, in wheat, barley , oats, grass seed and grassland crops.
[00109] As used herein, picloram is 4-amino-3,5,6trichloro-2-pyridinecarboxylic acid and has the following structure:
The [00110] Exemplary uses of picloram are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of picloram include its use for treating unwanted vegetation, for example, in pastures, grass pastures, forest, as well as grassland. non-culture and sites of passage. Exemplary chemical forms of picloram include, for example, picloram K ⁺ salt, which is 4-amino-3,5,6-trichloro-2-pyridinecarboxylic acid monopotassium salt and has the following structure:
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29/202
00 [00111] As used here, quincloraque is 3,7-dichloro-8quinolinocarboxylic acid and has the following structure:
[00112] Exemplary uses of quinclorak are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of quinclorak include its use for pre- and post-emergence control of specific grass and broadleaf weeds, for example, seeded rice direct and transplanted.
[00113] As used herein, triclopyr is 2 - [(3,5,6-trichloro-2pyridinyl) oxy] acetate and has the following structure:
[00114] Exemplary uses of triclopyr are described in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of triclopyr include its use to control weed species from trunk and broadleaf plants, for example, in prairie, untreated land cultivated, industrial areas, coniferous forests, rice crops and plantation. Exemplary chemical forms of triclopyr include, for example, TEA triclopyr, which is 2 - [(3,5,6-trichloro-2-pyridinyl) oxide] acetic acid composed of Μ, Μ-diethylethanamine and has the following structure:
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30/202
triclopyrine choline, which is 2 - ((3,5,6-trichloropyridin-2-yl) oxy) 2-hydroxyΜ, Μ, Μ-trimethylethanamine acetate and has the following structure
[00115] BEE triclopyr, which is 2 - [(3,5,6-trichloro-2-pyridinyl) oxy] 2-butoxyethyl acetate and has the following structure:
[00116] As used herein, methyl halauxifene (4-amino-3-chloro-6 (4-chloro-2-fluoro-3-methoxyphenyl) picolinate) has the following structure:
/ O h ₃ c [00117] It is described in US Patent No. 7,314,849 B2, which is incorporated herein by reference in its entirety. Exemplary uses of halauxifene-methyl include its use to control broadleaf weeds, for example, in cereal crops. Halauxifene-methyl can be used as other forms, for example, halauxifene K ⁺ (4-amino-
3-chloro-6- (4-chloro-2-fluoro-3-methoxyphenyl) potassium picolinate), which has the following structure:
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31/202
h ₃ c [00118] As used herein, herbicide means a compound, for example, and active, that kills, controls or otherwise adversely modifies the growth of plants.
[00119] As used herein, an herbicidally effective or vegetation control amount is an amount of active ingredient that causes an adverse vegetation modification effect, for example, causing deviations from natural development, killing, affecting regulation, causing dissection, causing delay and the like.
[00120] As used herein, control of undesirable vegetation means prevention, reduction, death or otherwise adversely modifying the development of plants and vegetation. Methods for controlling undesirable vegetation by applying certain herbicidal combinations or compositions are described here. Application methods include, but are not limited to, applications to vegetation or its location, for example, application to the area adjacent to vegetation, as well as pre-emergence, post-emergence, foliar applications (spread, direct, strip, point, mechanical, superior or rescue) and in applications in water (emerged and submerged vegetation, scattered, point, mechanics, injected in water, scattered granular, granular point, stirring bottle or direct flow spraying), through methods of application by hand , backpack, machine, tractor or aerial (plane and helicopter).
[00121] As used herein, plants and vegetation include, but are not limited to, germinating seeds, emerging seedlings, plants
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32/202 that emerge from vegetative propagules, immature vegetation and established vegetation.
[00122] As used herein, agriculturally acceptable salts and esters refers to salts and esters which exhibit herbicidal activity or which are or can be converted to plants, water or soil in the said 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, into the corresponding carboxylic acid which, depending on the pH, may be in dissociated form or not dissociated.
Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium and amine cations of the Formula:
R1R ² R ³ R ⁴ N + [00124] where R ¹ , R ² , R ³ and R ⁴ each independently represent hydrogen or C1-C12 alkyl, C3-C12 alkenyl or C3-C12 alkynyl, each it is optionally substituted by one or more hydroxy groups, C1-C4 alkoxy, C1-C4 alkylthio or phenyl, 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-butoxyethylamine, morpholine, cyclododecylamine or benzylamine or with a tetraalkylammonium hydroxide , such as tetramethylammonium hydroxide or choline hydroxide.
[00125] Exemplary esters include those derived from alcohols of
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33/202 alkyl substituted by C1-C2 alkyl, C3-C12 alkenyl, C3-C12 alkynyl or C7-C10 aryl, such as methyl alcohol, isopropyl alcohol, 1butane, 2-ethyl hexanol, butoxyethanol, methoxypropanol, allyl alcohol unsubstituted or substituted propargyl alcohol, cyclohexanol or benzyl alcohols. Benzyl alcohols can be substituted with from 1-3 substituents independently selected from halogen, C1-C4 alkyl or C1-C4 alkoxy. Esters can be prepared by coupling the acids with alcohol using any number of suitable activating agents such as those used for peptide couplings such as dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); by reacting the acids with alkylating agents such as alkyl halides and alkyl sulfonates in the presence of a base such as triethylamine or lithium carbonate; by reacting the corresponding acid chloride of an acid with an appropriate alcohol; through the reaction of the acid corresponding with an appropriate alcohol in the presence of an acid catalyst or through transesterification.
COMPOSITIONS AND METHODS [00126] Herbicidal compositions comprising a herbicidally effective amount of (a) a compound of Formula (I) are provided herein
NHo
Cl
OH (I)
H ₃ C [00127] or an agriculturally acceptable salt or ester thereof and (b) a synthetic auxin herbicide.
[00128] Methods for controlling unwanted vegetation including contact with vegetation or location are also provided here
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34/202 thereof, that is, an area adjacent to vegetation, with or application to soil or water to prevent the emergence or growth of vegetation of a herbicidally effective amount of the compound of Formula (I) or salt or ester of the same agriculturally acceptable and (b) a synthetic auxin herbicide. In certain embodiments, the method employs the compositions described here. In certain embodiments, the synthetic auxin is 2,4-D, 2,4-DB, aminocyclopyrachlor, aminopyralide, clomeprope-P, clopyralide, dicamba, dichlorprope-P, methyl ester fluroxypyr (MHE), MCPA, MCPB, picloram, quincloraque , triclopyr and halauxifene-methyl (4 amino-3- chloro-6- (4-chloro-2-fluoro-3-methoxyphenyl) -polyolinate) or an agriculturally acceptable salt or ester thereof.
[00129] Still, in some embodiments, the combination of compound (I) or salt or ester of the same agriculturally acceptable and synthetic auxin herbicides, or a salt or ester of the same agriculturally acceptable, exhibits synergism, for example, the herbicidal active ingredients they are more effective in combination than when applied individually. Synergism was defined as an interaction of two or more factors so 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 through Colby's equation. Colby, SR 1967, Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15: 20-22.
[00130] In certain embodiments of the compositions and methods described here, the compound of Formula (I), that is, carboxylic acid, is employed. In certain embodiments, a carboxylate salt of the compound of Formula (I) is employed. In certain embodiments, an aralkyl or alkyl ester is employed. In certain modalities, a benzyl,
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35/202 substituted benzyl or C1-4 alkyl, for example, n-butyl ester, is employed. In certain embodiments, the benzyl ester is used. [00131] In some embodiments, the compound of Formula (I) or salt or ester thereof and synthetic auxin are formulated into a composition, mixed in a tank, applied simultaneously or applied sequentially.
[00132] Herbicidal activity is exhibited by the compounds when they are applied directly to the plant or to the location of the plant at any stage of growth. The observed effect depends on the plant species to be controlled, the plant's growth stage, the application parameters of dilution and spray drop size, the particle size of the solid components, the environmental conditions at the time of use, the compound specific used, the specific adjuvants and vehicles used, the type of soil, and similar, as well as the amount of chemical agent 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 water application to flooded rice fields or bodies of water (for example, ponds, lakes and streams), to relatively undesirable immature vegetation to obtain maximum weed control.
[00133] In some embodiments, the compositions and methods provided here are used to control weeds in crops, including, but not limited to, direct sown rice, water-sown rice, transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn, sugar cane, sunflower, oilseed rape, canola, sugar beet, soy, cotton, pineapple, pasture, grassland, grassland, fallow, peat, tree and vine orchards, aquatic, plantation crops, vegetables, industrial vegetation management
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36/202 (IVM) and easements of passage (ROW).
[00134] In certain embodiments, the compositions and methods provided here are used to control weeds in rice. In certain modalities, rice is sown directly, sown in water or transplanted rice.
[00135] The compositions and methods described here can be used to control undesirable vegetation in glyphosate-tolerant crops, tolerant to 5-enolpyruvylshiquimate-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 auxin transport inhibitor, tolerant to aryloxyphenoxypropionate, tolerant to cyclohexanedione, tolerant to phenylpyrazoline, tolerant to acetyl CoA carboxylase inhibitor (ACCase) , tolerant to imidazolinone, tolerant to sulfonylurea, tolerant to pyrimidinylthiobenzoate, tolerant to triazolpyrimidine sulfonamide, tolerant to sulfonylaminocarbonyltriazolinone, tolerant to acetolactate synthase (ALS), tolerant to acid-hydroxide inhibitor-4-hydroxide inhibitor (AHAS), pyruvate dioxigenase (HPPD), tolerant to phytoe inhibitor ne desaturase, tolerant to carotenoid biosynthesis inhibitor, tolerant to protoporphyrinogen oxidase (PPO) inhibitor, tolerant to cellulose biosynthesis inhibitor, tolerant to mitosis inhibitor, tolerant to microtubule inhibitor, tolerant to much fatty acid inhibitor long, tolerant to fatty acid and lipid biosynthesis inhibitor, tolerant to photosystem I inhibitor, tolerant to photosystem II inhibitor, tolerant to triazine and tolerant to bromoxynil (such as, but not limited to, soy, cotton, canola / rapeseed for seed oil, rice, cereals, corn, sorghum, sunflower, sugar beet, sugar cane, peat, etc.), for example, together with glyphosate, EPSP synthase inhibitors,
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37/202 glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, ACCase inhibitors, imidazolinones, sulfonylsilines, trinylsilines, trifluinylsilines, pyridines of ALS or AHAS, HPPD inhibitors, phytene desaturase inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, long chain fatty acid inhibitors, acid biosynthesis inhibitors fat and lipid, photosystem I inhibitors, photosystem II inhibitors, triazines and bromoxynil. The compositions and methods can be used to control undesirable vegetation in crops presenting multiple or stacked characteristics 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 employed. In some embodiments, the compositions described here and other complementary herbicides are applied at the same time, either as a combination formulation, as a tank mixture or sequentially.
[00136] The compositions and methods can be used to control undesirable vegetation in crops showing tolerance to agronomic stress (including, but not limited to, drought, cold, heat, salt, water, nutrient, fertility, pH), tolerance to pestilence (including, but not limited to, insects, fungi, and pathogens) and breeding characteristics (including, but not limited to, yield; protein, carbohydrate or oil content; protein composition,
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38/202 carbohydrate or oil; plant stature and plant architecture). The compositions and methods provided herein 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 rape for seed oil, canola, sugar beet, soybeans, cotton, pineapple, pastures, grasslands, pastures, fallow, peat, tree and vine orchards, aquatic, plantation crops, vegetables, industrial vegetation management (IVM) and easements (ROW).
[00137] In some embodiments, the methods provided here are used to control undesirable vegetation in rice. In certain modalities, the undesired vegetation is Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass), BRAPP), Digitaria sanguinalis (L.) Scop. (large crabgrass), DIGSA), Echinochloa species (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (capimcapivara (barnyardgrass), ECHCG), Echinochloa crus-pavonis (Kunth) Schult. (spur-of-cock (gulf cockspur), ECHCV), Echinochloa colonum (L.) LINK (capim-jaú (junglerice), ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early ricegrass (early watergrass) , ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (capybara grass of rice (rice barnyardgrass, ECHPH), Echinochloa polystachya (Kunth) Hitchc. (beach grass (creeping river grass), ECHPO), Ischaemum rugosum Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L. ) Nees (Chinese grass (Chinese sprangletop), LEFCH), Leptochloa fascicularis (Lam.) Gray (bearded sprangletop, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazon grass (Amazon sprangletop), LEFPA), Oryza species (red rice and weed rice (red and weedy rice), ORYSS), Panicum dichotomiflorum (L.)
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Michx. (fall panicum, PANDI), Paspalum dilatatum Poir. (dallisgrass, PASDI), Rottboellia cochinchinensis (Lour.) W.D. Clayton (capimcamalote (itchgrass), ROOEX), Cyperus species (CYPSS), Cyperus difformis L. (small flower flatsedge), CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (yellow nutsedge), CYPES), Cyperus would L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge), CYPRO), Cyperus serotinus Rottb./CBClarke (CYPSE), Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (globe fringerush), FIMMI), Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb. (Japanese bulrush (Japanese bulrush), SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus L. Lye (sea clubrush, SCPMA), Schoenoplectus mucronatus L. (rice field bulge (ricefield bulrush), SCPMU), species Aeschynomene, (jointvetch, AESSS), Alternanthera philoxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alisma plantago-aquatica L. (common water plantain), ALSPA), Amaranthus species, (fedegosa and amarantos (pigweeds and amaranths), AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Commelina benghalensis L. (trapoeraba (Benghal dayflower), COMBE), Eclipta alba (L.) Hassk. (American false daisy, ECLAL), Heteranthera limosa (SW.) Willd./Vahl (deer tongue (ducksalad), HETLI), Heteranthera reniformis R. & P. (marsh mint) round leaf (roundleaf mudplantain), HETRE), Ipomoea species (morning primroses, IPOSS), Ipomoea hederacea (L.) Jacq. (ivy leaf primrose (ivyleaf morningglory), IPOHE), Lindernia dubia (L.) Pennell (basil (low false pimpernel), LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (southeastern primrose-willow), LUDLI), Ludwigia octovalvis (Jacq.) Raven (long fruit willow primrose
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40/202 (longfruited primrose-willow), LUDOC), Monochoria korsakowii Regel & Maack (monochromatic (monochoria), MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monochoria (monochoria), MOOVA), Murdannia nudiflora (L.) Brenan (dopeweed), MUDNU), Polygonum pensylvanicum L., (Pennsylvania smartweed), POLPY), Polygonum persicaria L. (ladysthumb), POLPE), Polygonum Michx hydropiperoides. (POLHP, mild smartweed), Rotala indica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species, (arrowhead), SAGSS), Sesbania exaltata (Raf.) Cory / Rydb. Ex Hill (hemp sesbania (hemp sesbania), SEBEX) or Sphenoclea zeylanica Gaertn. (gooseweed), SPDZE).
[00138] In some embodiments, the methods provided here are used to control undesirable vegetation on cereals. In certain embodiments, the unwanted vegetation is Alopecurus myosuroides Huds. ((blackgrass, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oat), AVEFA), Bromus tectorum L. (downy brome), BROTE), Lolium multiflorum Lam. (Italian ryegrass (Italian ryegrass), LOLMU), Phalaris minor Retz. (Small seed canary grass (littleseed canarygrass), PHAMI), Poa annua L. (annual bluegrass grass (annual bluegrass ), POANN), Setaria pumila (Poir.) Roemer & JA Schultes (yellow fox tail, SETLU), Setaria viridis (L.) Beauv. (Green fox tail, (green foxtail), SETVI), Amaranthus retroflexus L. (red-root fedegosa (redroot pigweed), AMARE), Brassica species (BRSSS), Chenopodium album L. (common lambsquarters), CHEAL), Cirsium arvense (L.) Scop. (Canadian thistle ( Canada thistle), CIRAR), Galium aparine L. (catchweed bedstraw), GALAP), Kochia scoparia (L.) Schrad. (Kochia, KCHSC), Lamium purpureum L. (purple lamina (purple
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41/202 deadnettle), LAMPU), Matricaria recutita L. (wild chamomile), MATCH), Matricaria matricarioides (Less.) Porter (pineapple weed (pineappleweed), MATMT), Papaver rhoeas L. (common poppy ( common poppy), PAPRH), Polygonum convolvulus L. (wild buckwheat), POLCO), Salsola tragus L. (Russian thistle), SASKR), Sinapis species (SINSS), Sinapis arvensis L. (mustard wild mustard, SINAR), Stellaria media (L.) Vill. (common chickweed, STEME), Veronica persica Poir. (Persian Veronica (Persian speedwell), VERPE), Viola arvensis Murr. (field violet), VIOAR) or Viola tricolor L. (wild violet, VIOTR).
[00139] In some modalities, the methods provided here are used to control unwanted vegetation in a pasture and pasture, fallow, IVM and ROW. In certain embodiments, the undesirable vegetation is Ambrosia artemisiifolia L. (common ragweed), AMBEL), Cassia obtusifolia (fedegoso (sickle pod), CASOB), Centaurea maculosa auct. non Lam. (spotted knapweed), CENMA), Cirsium arvense (L.) Scop. (Canadian thistle (Canada thistle), CIRAR), Convolvulus arvensis L. (field bindweed), CONAR), Daucus carota L. (wild carrot), DAUCA), Euphorbia esula L. (leafy euphorbia ( leafy spurge), EPHES), Lactuca serriola L./Torn. (prickly lettuce), LACSE), Plantago lanceolata L. (buckhorn plantain), PLALA), Rumex obtusifolius L. (broadleaf dock), RUMOB), Sida spinosa L. (malvinha (prickly sida), SIDSP), Sinapis arvensis L. (wild mustard), SINAR), Sonchus arvensis L. (perennial sowthistle), SONAR), Solidago species gold (goldenrod), SOOSS), Taraxacum officinale GH Weber ex Wiggers (dandelion
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42/202 (dandelion), TAROF), Trifolium repens L. (white clover), TRFRE) or Urtica dioica L. (common nettle), URTDI). [00140] In some embodiments, the methods provided here are used to control unwanted vegetation found in row crops, tree and vine crops and perennial crops. In certain embodiments, the unwanted vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wild oat), AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) R.D. Webster (Surinam grass (Surinam grass), BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) RD (beard grass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) RD Webster (broadleaf signalgrass), BRAPP), Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) R.D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (southern sandbur, CENEC), Digitaria horizontalis Willd. (Jamaica grass (Jamaican crabgrass), DIGHO), Digitaria insularis (L.) Mez ex Ekman (sourgrass), TRCIN), Digitaria sanguinalis (L.) Scop. (large crabgrass), DIGSA), Echinochloa crus-galli (L.) P. Beauv. (capybara grass (barnyardgrass), ECHCG), Echinochloa colonum (L.) Link (jaú grass (junglerice), ECHCO), Eleusine indica (L.) Gaertn. (goose grass (goosegrass), ELEIN), Lolium multiflorum Lam. (Italian ryegrass (Italian ryegrass), LOLMU), Panicum dichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild prose millet, PANMI), Setaria faberi Herrm. (giant foxtail), SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum halepense (L.) Pers. (Johnson grass (Johnsongrass), SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (wild sorghum (shattercane), SORVU), Cyperus
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43/202 esculentus L. (yellow nutsedge), CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilon theophrasti Medik. (velvet leaf (velvetleaf), ABUTH), Amaranthus species (fedegosas and amarantos (pigweeds and amaranths), AMASS), Ambrosia artemisiifolia L. (common ambrosia (common ragweed), AMBEL), Ambrosia psilostachya DC. (western ambrosia (western ragweed), AMBPS), Ambrosia trifida L. (giant ambrosia (giant ragweed), AMBTR), Anoda cristata (L.) Schlecht. (crested mallow (spurred anoda), ANVCR), Asclepias syriaca L. (common milkweed), ASCSY), Bidens pilosa L. (hairy beggarticks), BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (broadleaf buttonweed), BOILF), Spermacose latifolia (broadleaved button weed, BOILF), Chenopodium album L. (common lambsquarters), CHEAL), Cirsium arvense (L.) Scop. (Canadian thistle (Canada thistle), CIRAR), Commelina benghalensis L. (comelina (tropical spiderwort), COMBE), Datura stramonium L. (trumpet (jimsonweed), DATST), Daucus carota L. (wild carrot), DAUCA), Euphorbia heterophylla L. (wild poinsettia), EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden spurge, EPHHI), Euphorbia dentata Michx. (toothed spurge), EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy fleabane), ERIBO), Erigeron canadensis L. or Conyza canadensis (L.) Cronq. (Canadian fluff), Conyza sumatrensis (Retz.) EH Walker (tall fleabane), ERIFL), Helianthus annuus L. (common sunflower), HELAN), Jacquemontia tamnifolia (L. ) Griseb. (small flowermorningglory), IAQTA), Ipomoea hederacea (L.) Jacq. (ivy leaf morningglory, IPOHE), Ipomoea lacunosa L. (evening primrose
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44/202 white morning (white morningglory), IPOLA), Lactuca serriola L./Torn. (prickly lettuce), LACSE), Portulaca oleracea L. (common purslane), POROL), Richardia species (pusley, RCHSS), Sida species (sida, SIDSS), Sida spinosa L. (malvinha (prickly sida), SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), Tridax procumbens L. (bull's weed (coat buttons, TRQPR) or Xanthium strumarium L. (common cocklebur), XANST).
[00141] In some embodiments, the methods provided here are used to control unwanted vegetation in peat. In certain modalities, the undesired vegetation is Bellis perennis L. (English daisy), BELPE), Cyperus esculentus L. (yellow nutsedge), CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L.) Scop. (large crabgrass), DIGSA), Diodia virginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (euphorbia (spurge), EPHSS), Glechoma hederacea L. (ground ivy), GLEHE) , Hydrocotyle umbellata L. (acariçoba (dollarweed), HYDUM), Kyllinga species (junquinho (kyllinga), KYLSS), Lamium amplexicaule L. (wild mint (henbit), LAMAM), Murdannia nudiflora (L.) Brenan (trapoerabinha ( doveweed), MUDNU), Oxalis species (canary grass (woodsorrel), OXASS), Plantago major L. (broadleaf plantain), PLAMA), Plantago lanceolata L. (sheep-tongue / leaf plantain) (buckhorn / narrowleafplantain), PLALA), Phyllanthus urinaria L. (chamberbitter), PYLTE), Rumex obtusifolius L. (broadleaf dock), RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover),
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TRFRE) or Viola species (wild violet, VIOSS).
[00142] In some embodiments, the compositions and methods provided here are used to control undesirable vegetation consisting of grass, broadleaf weeds and sedge. In certain embodiments, the compositions and methods provided herein are used to control unwanted vegetation including, but not limited to, Amaranthus, Brachiaria, Brassica, Cassia, Centaurea, Cirsium, Cyperus, Digitaria, Echinochloa, Eleusina, Ischaemum, Kochia, Leptochloa, Panicum, Polygonum, Salsola, Sida, Sinapis, Solidago, Sonchus, Sorghum, Schoenoplectus, Stellaria, Trifolium and Viola.
[00143] In some embodiments, the combination of compound (I) or ester or salt of the same agriculturally acceptable and 2,4-D, aminocyclopyrachlor, aminopyralide, clomeprope-P, clopyralide, dicamba, dichlorprope-P, methyl heptyl ester ( MHE) fluroxypyr, MCPA, MCPB, picloram, quincloraque, triclopir and halauxifene-methyl (4-amino-3-chloro-6 (4-chloro-2-fluoro-3-methoxyphenyl) methyl picolinate) or its salt or ester agriculturally acceptable is used to control Amaranthus retroflexus (L.) (redroot pigweed), AMARE), Brachiaria platyphylla (Griseb.) Nash or Urochloa platyphylla (Nash) RD Webster (broadleaf signalgrass), BRAPP ), Brassica napus (L.) (volunteer canola), BRSNN), Cassia obtusifolia L. (fedegoso (sicklepod), CASOB), Cirsium arvense (L.) Scop. (Canadian thistle (Canada thistle), CIRAR), Centaurea maculosa LAM. (Greater cornflower, spotted (knapweed, spotted), CENMA), Cirsium arvense (L.) SCOP. (thistle, Canada (thistle, Canada), CIRAR), Cyperus difformis L. (small flower umbrella umbrella), CYPDI), Cyperus esculentus (L). (yellow nutsedge), CYPES), Cyperus would L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge), CYPRO), Digitaria sanguinalis (L.) Scop. (mattress grass
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46/202 grande (large crabgrass), DIGSA), Echinochloa crus-galli (L.) Beauv. (capybara grass (barnyardgrass), ECHCG), Echinochloa colona (L.) Link (jaime grass (junglerice), ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early ricegrass), ECHOR) , Eleusine indica (L.) Gaertn. (goose grass (goosegrass), ELEIN), Ischaemum rugosum Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees (Chinese grass (Chinese sprangletop), LEFCH), Panicum dichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild prose millet, PANMI), Polygonum convolvulus (L.), (wild buckwheat), POLCO), Schoenoplectus juncoides (Roxb. ) Palla (Japanese bulrush (Japanese bulrush), SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus (L.) Lye (sea clubrush, SCPMA), Sorghum halepense (L.) Pers. (Johnson grass (johnsongrass), Sida spinosa L. (malvinha (sida, prickly), SIDSP), Sinapis arvensis L. (mustard, wild (mustard, wild), SINAR), Solidago L. spec. (golden rod (goldenrod), SOOSS), Sonchus arvensis L. (thistle, field (sowthistle, field), SONAR), Sorghum halepense (L.) Pers. (Johnson grass (johnsongrass), SORHA), Stellaria media (L.) Vill (common chickweed), STEME), Trifolium repens L. (clover, Dutch, TRFRE) and Viola tricolor (L.) (wild violet (wild pansy), VIOTR).
[00144] The compounds of Formula I or agriculturally acceptable salt or ester thereof can be used to control herbicide resistant or tolerant weeds. The methods employing the combination of a Formula I compound or an agriculturally acceptable salt or ester thereof and the compositions described herein can also be employed to control herbicide resistant or herbicide tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes
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47/202 resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (for example, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolpyrimidines, sulfonylaminocarbonyltriazolinones), photosystemidine pyridine inhibitors (e.g. triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (eg, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines), synthetic auxins (eg, phenolic acids, pyridine acids, benzoic acids, carboxylic acids, quinoline carboxylic acids), auxin transport inhibitors (eg phthalates, semicarbazones), photosystem II inhibitors (eg bipyridyls), 5enolpyruvylshiquimato-3-phosphate (EPSP) inhibitors (eg glyphosate), inhibitors glutamine synthetase (eg glufosinate, bialaphos), assembly inhibitors microtubule (eg benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (eg carbamates), very long chain fatty acid inhibitors (VLCFA) (eg acetamides, chloroacetamides, oxyacetamides, tetrazolinones ), inhibitors of fatty acid and lipid biosynthesis (for example, phosphorodithioates, thiocarbamates, benzofurans, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibitors (for example, diphenylethers, N-phenylphthalimides, oxadiazoles, oxazolidinediones, pyridines, trisilines, trisilinase, ), carotenoid biosynthesis inhibitors (eg clomazone, amitrol, aclonifen), phytene desaturase inhibitors (PDS) (eg amides, anilidex, furanones, phenoxybutanamides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate inhibitors dioxigenase (HPPD) (eg, calistemones, isoxazoles, pyrazoles, tricetones), cellulose biosynthesis inhibitors (p for example, nitriles, benzamides, quinclorak, triazolcarboxamides),
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48/202 herbicides with multiple modes of action such as quinclorak and unclassified herbicides such as arylaminopropionic, difenzoquate, endotal and organoarsenic acids. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes and multiple modes of action of herbicide and biotypes with multiple resistance or tolerance mechanisms (for example, resistance to target site or metabolic resistance).
[00145] 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 2,4-D, or carboxylate salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to 2,4-D or carboxylate salt or ester thereof is within the range of from about 1: 1120 to about 4: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to 2,4-D or carboxylate salt or ester thereof is within the range of from 1: 128 to about 1 :1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to 2,4-D or carboxylate salt or ester thereof is within the range of from about 1: 200 to about of 1: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to 2,4-D or carboxylate salt or ester thereof is within the range of from about 1:96 to about of 1: 2. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl ester and 2,4-D DMA, 2,4-D choline or 2,4-D EHE. In one embodiment, the composition comprises the compound of Formula (I) and 2,4-D DMA, where the weight ratio of the compound of Formula (I) to 2,4-D DMA is about 1:56 to about
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1: 4. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and 2,4-D DMA, where the weight ratio of the benzyl ester of the compound of Formula (I) to 2,4-D DMA is about 1:56 to about 1: 2. In one embodiment, the composition comprises the compound of Formula (I) and 2,4-D choline, where the weight ratio of the compound of Formula (I) to 2.4 -D choline is about 1:84 to about 1: 6,9. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and 2,4-D choline, where the weight ratio of benzyl ester of the compound of Formula (I) for 2,4-D choline is about 1:96 to about 1: 6. In one embodiment, the composition comprises the compound of Formula (I) and 2,4-D EHE, where the weight ratio of the compound of Formula (I) to 2,4-D EHE is about 1:56 to about 1: 4. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and 2,4-D EHE, where the weight ratio of the benzyl ester of the compound of Formula (I) to 2,4-D EHE is about 1:56 to about 1: 4, regarding methods. In certain embodiments, the methods comprise contact of unwanted vegetation or its locus or application to soil or water to prevent the emergence or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of from about 37 grams of acid equivalent per hectare (gae / ha) to about 2540 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 39 grams of acid equivalent per hectare (gae / ha) to about 515 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or
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50/202 ester thereof and 2,4-D or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, the 2,4-D or carboxylate salt or ester thereof is applied at a rate of from about 35 gae / ha to about 480 gae / ha and the salt Formula (I) compound or ester thereof is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In some embodiments, the 2,4-D or carboxylate salt or ester thereof is 2,4-DB, 2,4-D choline, 2,4-D DMA or 2,4-D EHE. In some embodiments, 2,4-D or the carboxylate salt or ester thereof is applied at a rate of from about 17 gai / ha to about 1000 gai / ha and the salt Formula (I) compound or ester thereof is applied at a rate of from about 0.5 g of acid equivalent per hectare (gae / ha) to about 70 gae / ha. In some embodiments, the 2,4D or carboxylate salt or ester thereof is applied at a rate of from about 35 gai / ha to about 480 gai / ha and the compound of Formula (I) or salt or ester of it is applied at a rate of from about 1.1 g of acid equivalent per hectare (gae / ha) to about 35 gae / ha. In certain embodiments, the methods use the compound of Formula (I), or its benzyl ester and 2,4-D DMA, 2,4-D choline or 2,4-D EHE. In one embodiment, the methods use the compound of Formula (I) and 2,4-D DMA, where the compound of Formula (I) is applied at a rate of from about 3.75 g of acid equivalent per hectare (gae / ha) at about 35 gae / ha, and 2,4-D DMA is applied at a rate of about 70 gai / ha to about 280 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and 2,4-D DMA, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 3 , 75 g of acid equivalent per hectare (gae / ha) at about 35 gae / ha, and 2,4-D DMA is applied at a rate of about 35 gai / ha to about 280 gai / ha. In one embodiment, the methods use the compound of Formula (I) and 2,4-D choline, where the
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51/202 compound of Formula (I) is applied at a rate of from about 4.38 g of acid equivalent per hectare (gae / ha) to about 35 gae / ha, and 2,4-D choline is applied at a rate of about 105 gai / ha to about 480 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and 2,4-D choline, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 1 , 1 g of acid equivalent per hectare (gae / ha) at about 35 gae / ha, and 2,4-D choline is applied at a rate of about 50 gai / ha to about 480 gai / ha. In one embodiment, the methods use the compound of Formula (I) and 2,4-D EHE, where the compound of Formula (I) is applied at a rate of from about 4.38 g of acid equivalent per hectare (gae / ha) at about 35 gae / ha, and 2,4-D EHE is applied at a rate of about 70 gai / ha to about 280 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and 2,4-D EHE, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 4 , 38 g of acid equivalent per hectare (gae / ha) at about 17.5 gae / ha and 2,4-D EHE is applied at a rate of about 70 gai / ha to about 280 gai / ha. In certain embodiments, the methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with
2,4-D or carboxylate salt or ester thereof are used to control ECHCG, LEFCH, ECHOR, CYPRO, SCPJU, CENMA, SINAR, SONAR, POLCO, PANDI, ELEIN, PANMI, DIGSA, ECHCO, CYPES, CYPIR, SCPMA , CASOB, or BRAPP.
[00146] 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 aminocyclopyrachlor or carboxylate salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester of the same aminocyclopyrachlor or carboxylate salt or ester of
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52/202 is even within the range of from about 1: 140 to about 34: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to aminocyclopyrachlor or carboxylate salt or ester thereof is within the range from 1:91 to about 12: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to aminocyclopyrachlor or carboxylate salt or ester thereof is within the range of from 1: 4 to about 2: 1. In certain embodiments, the compositions comprise the compound of Formula (I) or its benzyl or n-butyl ester and aminocyclopyrachlor. Regarding methods. In certain embodiments, the methods comprise contact of unwanted vegetation or its locus or application to soil or water to prevent the emergence or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of from about 10 grams of acid equivalent per hectare (gae / ha) to about 580 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 11 grams of acid equivalent per hectare (gae / ha) to about 300 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and aminocyclopyrachlor or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, the aminocyclopyrachlor or carboxylate salt or ester thereof is applied at a rate of from about 8.8 gae / ha to about 280 gae / ha and the compound of Formula (I) of salt or ester of it is applied at a rate of from about 2 gae / ha to about
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53/202 of 300 gae / ha. In one embodiment, the aminocyclopyrachlor or carboxylate salt or ester thereof is applied at a rate of from about 8.75 gae / ha to about 17.5 gae / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of from about 4.4 gae / ha to about 17.5 gae / ha. In certain embodiments, the methods use the compound of Formula (I) or its benzyl or n-butyl ester and aminocyclopyrachlor. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with aminocyclopyrachlor or carboxylate salt or ester thereof are used to control TRFRE, SINAR or CENMA. [00147] 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 aminopyralide or carboxylate salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to aminopyralide or carboxylate salt or ester thereof is within the range of from about 1:60 to about 100: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to aminopyralide or carboxylate salt or ester thereof is within the range of from 1: 8 to about 6: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to aminopyralide or carboxylate salt or ester thereof is within the range of from about 1:16 to about 6: 1 . In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to aminopyralide or carboxylate salt or ester thereof is within the range of from about 1: 8 to about 3: 1 . In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl and aminopyralide or aminopyralide TIPA ester. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I)
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54/202 and aminopyralide, where the weight ratio of the benzyl ester of the compound of Formula (I) to aminopyralide is about 3: 1. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and aminopyralide TIPA, where the weight ratio of the benzyl ester of the compound of Formula (I) to aminopyralide TIPA is about 1: 8 to about 1: 1. Regarding methods. In certain embodiments, the methods comprise contact of unwanted vegetation or its locus or application to soil or water to prevent the emergence or growth of vegetation with a composition described here. In some embodiments, the composition is applied at an application rate of from about 5 grams of acid equivalent per hectare (gae / ha) to about 420 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 7 grams of acid equivalent per hectare (gae / ha) to about 53 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and aminopyralide or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, the aminopyralide or carboxylate salt or ester thereof is applied at a rate of from about 3 gae / ha to about 120 gae / ha and the compound of Formula (I) of the salt or ester thereof it is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In some embodiments, the aminopyralide or carboxylate salt or ester thereof is applied at a rate of from about 1 gai / ha to about 70 gai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of from about 2 g of acid equivalent
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55/202 per hectare (gae / ha) to about 45 gae / ha. In some embodiments, the aminopyralide or carboxylate salt or ester thereof is applied at a rate of from about 3 gai / ha to about 35 gai / ha and the compound of Formula (I) of salt or ester thereof it is applied at a rate of from about 4.4 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 aminopyralide or TIPA aminopyralide. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and aminopyralide, where 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 aminopyralide is applied at a rate of about 3 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and TIPA aminopyralide, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 4.4 g to acid equivalent per hectare (gae / ha) at about 17.5 gae / ha and TIPA aminopyralide is applied at a rate of about 3 gai / ha to about 35 gai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with aminopyralide or carboxylate salt or ester thereof are used to control POLCO, CIRAR, BRSNN, TRFRE, SINAR, SOOSS or CENMA.
[00148] 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 clomeprop-P or salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to clomeprope-P or salt or ester thereof is within the range of from about 1: 200 to about 6: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to
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56/202 clomeprope-P or salt or ester thereof is within the range of from 1: 159 to about 1: 1. In certain embodiments, the compositions comprise the compound of Formula (I) or its benzyl or butyl ester and clomeprope-P. With respect to the methods, in certain modalities, the methods comprise contact of the unwanted vegetation or its locus or application to the soil or water to prevent the emergence or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of from about 52 grams of acid equivalent per hectare (gae / ha) to about 700 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 53 grams of acid equivalent per hectare (gae / ha) to about 400 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and clomeprope-P or salt of the even, for example, sequentially or simultaneously. In some embodiments, clomeprope-P or its salt or ester is applied at a rate of from about 50 gae / ha to about 400 gae / ha and the compound of Formula (I) and salt or ester thereof it is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In certain embodiments, the methods use the compound of Formula (I) or its benzyl or n-butyl ester and clomeprope-P.
[00149] 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 clopyralide or carboxylate salt or ester thereof. Regarding the compositions, in some modalities, the
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57/202 weight ratio of the compound of Formula (I) or salt or ester thereof to clopyralide or carboxylate salt or ester thereof is within the range of from about 1: 280 to about 9: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to clopyralide or carboxylate salt or ester thereof is within the range of from 1:23 to about 1: 4. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to clopyralide or carboxylate salt or ester thereof is within the range of from about 1:32 to about 1: 2 . In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to clopyralide or carboxylate salt or ester thereof is within the range of from about 1:16 to about 1: 4 . In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl and clopyralide ester or MEA clopyralide. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and clopyralide, where the weight ratio of the benzyl ester of the compound of Formula (I) to clopyralide is about 1: 5.7. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and MEA clopyralide, where the weight ratio of the benzyl ester of the compound of Formula (I) to clopyralide MEA is about 1: 4 to about 1:16. Regarding methods. In certain embodiments, the methods comprise contact of unwanted vegetation or its locus or application to soil or water to prevent the emergence or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of from about 37 grams of acid equivalent per hectare (gae / ha) to about 860 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 38 grams
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58/202 of acid equivalent per hectare (gae / ha) to about 59 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and clopyralide or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, the clopyralide or carboxylate salt or ester thereof is applied at a rate of from about 35 gae / ha to about 560 gae / ha and the compound of Formula (I) of the salt or ester thereof it is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In some embodiments, the clopyralide or carboxylate salt or ester thereof is applied at a rate of from about 17 gai / ha to about 100 gai / ha and the compound of Formula (I) of the salt or ester thereof it is applied at a rate of from about 1 g of acid equivalent per hectare (gae / ha) to about 18 gae / ha. In some embodiments, the clopyralide or carboxylate salt or ester thereof is applied at a rate of from about 35 gai / ha to about 50 gai / ha and the compound of Formula (I) the salt or ester thereof it is applied at a rate of from about 2.2 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 and clopyralide ester or MEA clopyralide. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and clopyralide, where 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 clopyralide is applied at a rate of about 50 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and MEA clopyralide, where the benzyl ester of the compound of Formula (I) is applied at a rate of
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59/202 from about 2.2 g of acid equivalent per hectare (gae / ha) to about 8.8 gae / ha and MEA clopyralide is applied at a rate of about 35 gai / ha to 50 gai / there is. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with clopyralide or carboxylate salt or ester thereof are used to control AMARE, CIRAR or SOOSS.
[00150] 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 dicamba or carboxylate salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to dicamba or carboxylate salt or ester thereof is within the range of from about 1: 1100 to about 8: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to dicamba or carboxylate salt or ester thereof is within the range of from 1: 254 to about 1: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to dicamba or carboxylate salt or ester thereof is within the range of from about 1: 120 to about 1: 1 . In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to dicamba or carboxylate salt or ester thereof is within the range of from about 1:56 to about 1: 3 , 3. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl and dicamba ester or DMA dicamba. In one embodiment, the composition comprises the compound of Formula (I) and dicamba, where the weight ratio of the compound of Formula (I) to dicamba is about 1:56 to about 1: 3.3. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and dicamba, where the weight ratio of the benzyl ester of the compound of Formula (I) to dicamba is
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60/202 about 1:56 to about 1: 4. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and dicamba DMA, where the weight ratio of the benzyl ester of the compound of Formula (I) to dicamba DMA is about 1: 45.5 to about 1: 11.4. With respect to the methods, in certain modalities, the methods comprise contact of the unwanted vegetation or its locus or application to the soil or water to prevent the emergence or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of from about 36 grams of acid equivalent per hectare (gae / ha) to about 2500 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 37 grams of acid equivalent per hectare (gae / ha) to about 325 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and dicamba or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, the dicamba or carboxylate salt or ester thereof is applied at a rate of from about 35 gae / ha to about 2200 gae / ha and the compound of Formula (I) of salt or ester thereof it is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In some embodiments, the dicamba or carboxylate salt or ester thereof is applied at a rate of from about 17 gai / ha to about 600 gai / ha and the compound of Formula (I) or salt or ester thereof it is applied at a rate of from about 0.5 g of acid equivalent per hectare (gae / ha) to about 100 gae / ha. In some modalities, dicamba
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61/202 or carboxylate salt or ester thereof is applied at a rate of from about 35 gai / ha to about 280 gai / ha and the compound of Formula (I) or salt or ester thereof is applied in a rate from about 1.1 g of acid equivalent per hectare (gae / ha) to about
42.4 gae / ha. In certain embodiments, the methods use the compound of Formula (I), or its benzyl and dicamba ester or DMA dicamba. In one embodiment, the methods use the compound of Formula (I) and dicamba, where the compound of Formula (I) is applied at a rate of from about 5.3 g of acid equivalent per hectare (gae / ha) at about 42.4 gae / ha, and dicamba is applied at a rate of about 140 gai / ha to about 280 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and dicamba, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 2.2 g of equivalent acid per hectare (gae / ha) at about 35 gae / ha, and dicamba is applied at a rate of about 35 gai / ha to about 280 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and DMA dicamba, where the benzyl ester of the compound of Formula (I) is applied at a rate of about 1.1 g of acid equivalent per hectare (gae / ha) at about 4.4 gae / ha, and dicamba DMA is applied at a rate of around 50 gai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with dicamba or carboxylate salt or ester thereof are used to control LEFCH, CYPIR, ECHCO, ECHCG, ECHOR, SCPMA, AMARE, POLCO, BRSNN, SIDSP, SINAR or CASOB.
[00151] 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 dichlorprope-P or carboxylate salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester of the
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62/202 even for dichlorprope-P or carboxylate salt or ester thereof is within the range of from about 1: 5,700 to about 2: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to dichlorprope-P or salt of carboxylate or ester thereof is within the range of from 1: 1000 to about 1: 3 . In certain embodiments, the compositions comprise the compound of Formula (I) or its benzyl or n-butyl ester and dichlorprope-P. Regarding methods. In certain embodiments, the methods comprise contact of unwanted vegetation or its locus or application to soil or water to prevent the emergence or growth of vegetation with a composition described here. In some embodiments, the composition is applied at an application rate of from about 142 grams of acid equivalent per hectare (gae / ha) to about 11,700 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 144 grams of acid equivalent per hectare (gae / ha) to about 2290 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and dichlorprope-P or salt of the even, for example, sequentially or simultaneously. In some embodiments, dichlorprope-P or the carboxylate salt or ester thereof is applied at a rate of from about 140 gae / ha to about 11,400 gae / ha and the compound of Formula (I) or salt or ester of it is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In certain embodiments, the methods use the compound of Formula (I) or its benzyl or n-butyl ester and dichlorprope-P.
[00152] In certain modalities of the compositions and methods
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63/202 described herein, the compound of Formula (I) or salt or ester thereof is used in combination with fluroxypyr or carboxylate salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to fluroxypyr or carboxylate salt or ester thereof is within the range of from about 1: 1120 to about 4: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to fluroxypyr or carboxylate salt or ester thereof is within the range of from 1: 127 to about 2: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to fluroxypyr or carboxylate salt or ester thereof is within the range of from about 1:70 to about 1: 1 . In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to fluroxypyr or carboxylate salt or ester thereof is within the range of from about 1:35 to about 1: 2 . In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl or butyl ester and fluroxypyr or MHE floxoxypyr. In one embodiment, the composition comprises the compound of Formula (I) and MHE fluroxypyr, where the weight ratio of the compound of Formula (I) to MHE fluroxypyr is about 1:28 to about 1: 7. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and MHE fluroxypyr, where the weight ratio of the benzyl ester of the compound of Formula (I) to MHE fluroxypyr is about 1:35 to about 1: 2. In one embodiment, the composition comprises the n-butyl ester of the compound of Formula (I) and MHE fluroxypyr, where the weight ratio of the n-butyl ester of the compound of Formula (I) to MHE fluroxypyr is about 1:17 , 5 to about 1: 8.2. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and fluroxypyr, where the weight ratio of the benzyl ester of the compound of Formula
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64/202 (I) for fluroxypyr is about 1: 4. Regarding methods. In certain embodiments, the methods comprise contact of unwanted vegetation or its locus or application to soil or water to prevent the emergence or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of from about 37 grams of acid equivalent per hectare (gae / ha) to about 860 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 38 grams of acid equivalent per hectare (gae / ha) to about 315 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and fluroxypyr or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, the fluroxypyr or carboxylate salt or ester thereof is applied at a rate of from about 35 gae / ha to about 560 gae / ha and the compound of Formula (I) of the salt or ester thereof it is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In some embodiments, the fluroxypyr or carboxylate salt or ester thereof is applied at a rate of from about 17 gae / ha to about 600 gae / ha and the compound of Formula (I) of salt or ester thereof it is applied at a rate of from about 1 g of acid equivalent per hectare (gae / ha) to about 70 gae / ha. In some embodiments, the fluroxypyr or carboxylate salt or ester thereof is applied at a rate of from about 35 gae / ha to about 280 gae / ha and the compound of Formula (I) of salt or ester thereof it is applied at a rate of from about 2.2 g of acid equivalent per hectare (gae / ha) to about 35 gae / ha.
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65/202
In some embodiments, the fluroxypyr or carboxylate salt or ester thereof is applied at a rate of from about 35 gae / ha to about 280 gae / ha and the compound of Formula (I) of salt or ester thereof it is applied at a rate of from about 2.2 g of acid equivalent per hectare (gae / ha) to about 64 gae / ha. In certain embodiments, the methods use the compound of Formula (I), or its benzyl or n-butyl ester and fluroxypyr or MHE fluroxypyr. In one embodiment, the methods use the compound of Formula (I) and MHE fluroxypyr, where the compound of Formula (I) is applied at a rate of from about 4.38 g of acid equivalent per hectare (gae / ha ) at about 64 gae / ha, and fluroxypyr MHE is applied at a rate of about 70 gae / ha to about 280 gae / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and fluroxypyr MHE, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 2.2 g of acid equivalent per hectare (gae / ha) at about 64 gae / ha, and MHE fluroxypyr is applied at a rate of about 35 gae / ha to about 280 gae / ha. In one embodiment, the methods use the n-butyl ester of the compound of Formula (I) and fluroxypyr MHE, where the n-butyl ester of the compound of Formula (I) is applied at a rate of about 16 g of equivalent acid per hectare (gae / ha) at about 35 gae / ha, and MHE fluroxypyr is applied at a rate of about 70 gae / ha to about 280 gae / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and fluroxypyr, where 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) at about 64 gae / ha, and fluroxypyr is applied at a rate of about 35 gae / ha to about 280 gae / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with fluroxypyr or carboxylate salt or ester thereof are used to control SOOSS, CIRAR, CENMA,
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SONAR, TRFRE, ECHCG, ECHCO, CYPDI, LEFCH, ECHOR, SCPJU, SCPMA, AMARE, VIOTR or POLCO.
[00153] 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 MCPA or carboxylate salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to MCPA or carboxylate salt or ester thereof is within the range of from about 1: 850 to about 10: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to MCPA or carboxylate salt or ester thereof is within the range of from 1: 509 to about 2: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to MCPA or carboxylate salt or ester thereof is within the range of from about 1:60 to about 1: 1 . In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to MCPA or carboxylate salt or ester thereof is within the range of from about 1:28 to about 1: 2 . In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl or n-butyl ester and MCPA, MCPA K ⁺ , Na ⁺ , DMA or EHE MCPA. In one embodiment, the composition comprises the compound of Formula (I) and MCPA K +, Na +, DMA, where the weight ratio of the compound of Formula (I) to MCPA K +, Na +, DMA is about 1:28 to about 1: 2. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and MCPA K ⁺ , Na ⁺ , DMA, where the weight ratio of the benzyl ester of the compound of Formula (I) to MCPA K ⁺ , Na ⁺ , DMA is about 1:28 to about 1: 4. In one embodiment, the composition comprises the compound of Formula (I) and EHE MCPA, where the weight ratio of the compound of Formula (I) to MCPA EHE is about 1: 6.6.
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In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and EHE MCPA, where the weight ratio of the benzyl ester of the compound of Formula (I) to MCPA EHE is about 1: 8. In one embodiment, the composition comprises the n-butyl ester of the compound of Formula (I) and EHE MCPA, where the weight ratio of the n-butyl ester of the compound of Formula (I) to MCPA EHE is about 1:17, 5 to about 1: 8. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and MCPA, where the weight ratio of the benzyl ester of the compound of Formula (I) to MCPA is about 1:16. With respect to the methods, in certain modalities, the methods comprise contact of unwanted vegetation or its locus or application to soil or water to prevent the emergence or growth of vegetation with a composition described here. In some modalities, the composition is applied at a rate of application from about 32 grams of acid equivalent per hectare (gae / ha) to about 2000 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 33 grams of acid equivalent per hectare (gae / ha) to about 1170 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and MCPA or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, the MCPA or carboxylate salt or ester thereof is applied at a rate of from about 30 gae / ha to about 1700 gae / ha and the compound of Formula (I) of the salt or ester thereof it is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In some
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68/202 modalities, the MCPA or carboxylate salt or ester thereof is applied at a rate of from about 35 gai / ha to about 600 gai / ha and the compound of Formula (I) of salt or ester of the it is applied at a rate of from about 2 g of acid equivalent per hectare (gae / ha) to about 90 gae / ha. In some embodiments, the MCPA or carboxylate salt or ester thereof is applied at a rate of from about 70 gai / ha to about 280 gai / ha and the compound of Formula (I) of salt or ester thereof it is applied at a rate of from about 4.38 g of acid equivalent per hectare (gae / ha) to about 42.4 gae / ha. In certain embodiments, the methods use the compound of Formula (I), or its benzyl or n-butyl ester and MCPA, MCPA K +, Na +, DMA, or EHE MCPA. In one embodiment, the methods use the compound of Formula (I) and MCPA K +, Na +, DMA, where the compound of Formula (I) is applied at a rate of from about 4.38 g of acid equivalent per hectare (gae / ha) at about 35 gae / ha, and MCPA K +, Na +, DMA is applied at a rate of about 70 gai / ha to about 140 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and MCPA K +, Na +, DMA, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 4 , 38 g of acid equivalent per hectare (gae / ha) at about
17.5 gae / ha, and MCPA K +, Na +, DMA is applied at a rate of about 70 gai / ha to about 140 gai / ha. In one embodiment, the methods use the compound of Formula (I) and EHE MCPA, where the compound of Formula (I) is applied at a rate of about 42.4 g of acid equivalent per hectare (gae / ha) and MCPA EHE is applied at a rate of about 280 gae / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and EHE MCPA, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 35 g of acid equivalent per hectare (gae / ha) and MCPA EHE is applied at a rate of around 280 gae / ha. In a
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69/202 modality, the methods use the n-butyl ester of the compound of Formula (I) and EHE MCPA, where the n-butyl ester of the compound of Formula (I) is applied at a rate of about 16 g of acid equivalent per hectare (gae / ha) at about 35 gae / ha, and MCPA EHE is applied at a rate of around 280 gae / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and MCPA, where 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) at about 42 gae / ha, and MCPA is applied at a rate of about 70 gae / ha to about 280 gae / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and MCPA, where 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 MCPA is applied at a rate of around 140 gae / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with MCPA or carboxylate salt or ester thereof are used to control DIGSA, ECHCG, LEFCH, BRAPP, ECHOR, SCPJU, VIOTR, POLCO or BRSNN.
[00154] 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 MCPB or salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to MCPB or salt or ester thereof is within the range of from about 1: 250 to about 3: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to MCPB or salt or ester thereof is within the range of from 1: 150 to about 0.75: 1. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl ester or n
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70/202 butyl and MCPB. With respect to the methods, in certain modalities, the methods comprise contact of the unwanted vegetation or its locus or application to the soil or water to prevent the emergence or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of from about 102 grams of acid equivalent per hectare (gae / ha) to about 2000 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 110 grams of acid equivalent per hectare (gae / ha) to about 650 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and MCPB or salt or ester of even, for example, sequentially or simultaneously. In some embodiments, the MCPB or salt or ester thereof is applied at a rate of from about 100 gae / ha to about 1700 gae / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate from about 2 gae / ha to about 300 gae / ha. In some embodiments, the MCPB or salt or ester thereof is applied at a rate of from about 35 gai / ha to about 500 gai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of from about 2 g of acid equivalent per hectare (gae / ha) to about 150 gae / ha. In certain embodiments, the methods use the compound of Formula (I), or its benzyl or n-butyl ester and MCPB or MCPB ethyl ester. In the modality, the methods use the n-butyl ester of the compound of Formula (I) and ethyl ester MCPB, where the n-butyl ester of the compound of Formula (I) is applied at a rate of about 3 g of acid equivalent per hectare (gae / ha)
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71/202 at about 150 gae / ha and MCPB ethyl ester is applied at a rate of about 100 to about 500 gae / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with MCPB or salt or ester thereof are used to control ECHCG, ECHOR and SCPJU.
[00155] 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 mecoprope-P or carboxylate salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to mecoprope-P or carboxylate salt or ester thereof is within the range of from about 1: 1680 to about 1.5: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to mecoprope-P or carboxylate salt or ester thereof is within the range of from 1: 600 to about 1: 4 . In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to mecoprope-P or carboxylate salt or ester thereof is within the range of from about 1:60 to about 1 : 7. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to mecoprope-P or carboxylate salt or ester thereof is within the range of from about 1:30 to about 1 : 15. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to mecoprope-P or carboxylate salt or ester thereof is about 1: 22.9. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl ester and mecoprop-P. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and mecoprope-P, where the weight ratio of the benzyl ester of the compound of Formula (I) to mecoprope-P is about 1:22, 9. With regard to methods, in certain
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72/202 modalities, the methods comprise contact of unwanted vegetation or its locus or application to soil or water to prevent the emergence or growth of vegetation with a composition described here. In some embodiments, the composition is applied at an application rate of from about 202 grams of acid equivalent per hectare (gae / ha) to about 3600 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 204 grams of acid equivalent per hectare (gae / ha) to about 1270 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and mecoprope-P or salt of carboxylate or ester thereof, for example, sequentially or simultaneously. In some embodiments, mecoprope-P or the carboxylate salt or ester thereof is applied at a rate of from about 200 gae / ha to about 3360 gae / ha and the compound of Formula (I) of salt or ester of it is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In some embodiments, mecoprope-P or the carboxylate salt or ester thereof is applied at a rate of from about 90 gai / ha to about 500 gai / ha and the compound of Formula (I) of salt or ester it is applied at a rate of from about 3 g of acid equivalent per hectare (gae / ha) to about 24 gae / ha. In some embodiments, mecoprope-P or the carboxylate salt or ester thereof is applied at a rate of from about 180 gai / ha to about 220 gai / ha and the compound of Formula (I) of salt or ester of it is applied at a rate of from about 6 g of acid equivalent per hectare (gae / ha) to about 12 gae / ha. In
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73/202 some modalities, mecoprope-P or carboxylate salt or ester thereof is applied at a rate of about 200 gai / ha and the compound of Formula (I) or salt or ester thereof is applied at a rate of a from about 8.75 g of acid equivalent per hectare (gae / ha). In certain embodiments, the methods use the compound of Formula (I) or its benzyl ester and mecoprop-P. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and mecoprope-P, where 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 mecoprope-P is applied at a rate of about 200 gai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with mecopropeP or carboxylate salt or ester thereof are used to control BRSNN.
[00156] 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 pichloram or carboxylate salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to picloram or carboxylate salt or ester thereof is within the range of from about 1: 560 to about 30: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to picloram or carboxylate salt or ester thereof is within the range of from 1:16 to about 1: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to picloram or carboxylate salt or ester thereof is within the range of from about 1:32 to about 2: 1 . In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to picloram or carboxylate salt or ester thereof is within the range of from about 1:16 to about
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1: 1.1. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl ester and picloram or picloram K ⁺ . In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and picloram, where the weight ratio of the benzyl ester of the compound of Formula (I) to picloram is about 1:16 to about 1: 2. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and picloram K ⁺ , where the weight ratio of the benzyl ester of the compound of Formula (I) to picloram K + is about 1 : 1,: 1. With respect to the methods, in certain modalities, the methods comprise contact of the unwanted vegetation or its locus or application to the soil or water to prevent the emergence or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of from about 12 grams of acid equivalent per hectare (gae / ha) to about 1420 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 13 grams of acid equivalent per hectare (gae / ha) to about 88 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and picloram or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, the picloram or carboxylate salt or ester thereof is applied at a rate of from about 10 gae / ha to about 1120 gae / ha and the compound of Formula (I) or salt or ester thereof it is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In some embodiments, picloram or the carboxylate salt or ester of
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75/202 same is applied at a rate of from about 4 gai / ha to about 140 gai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of from about from 2 g of acid equivalent per hectare (gae / ha) to about 45 gae / ha. In some embodiments, picloram or the carboxylate salt or ester thereof is applied at a rate of from about 10 gai / ha to about 70 gai / ha and the compound of Formula (I) or salt or ester thereof it is applied at a rate of from about 4.4 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 or n-butyl ester and picloram or picloram K ⁺ . In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and picloram, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 4.4 g of equivalent acid per hectare (gae / ha) at about 17.5 gae / ha, and picloram is applied at a rate of about 10 gai / ha to about 70 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and picloram K +, where 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 picloram K + is applied at a rate of about 10 gai / ha. In certain embodiments, the methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with picloram or carboxylate salt or ester thereof are used to control CENMA, SINAR, VIOTR, STEME or POLCO.
[00157] 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 quinclorac or carboxylate salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to quinclorac or carboxylate salt or ester thereof is
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76/202 within the range of from about 1: 280 to about 4: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to quinclorak or carboxylate salt or ester thereof is within the range of from 1: 127 to about 1: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to quinclorak or carboxylate salt or ester thereof is within the range of from about 1: 130 to about 1: 3 . In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to quinclorak or carboxylate salt or ester thereof is within the range of from about 1:64 to about 1: 6 , 6. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl or n-butyl ester and quinclorac. In one embodiment, the composition comprises the compound of Formula (I) and quinclorak, where the weight ratio of the compound of Formula (I) to quinclorak is about 1:64 to about 1: 6.6. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and quinclorak, where the weight ratio of the benzyl ester of the compound of Formula (I) to quinclorak is about 1:56 to about 1: 8. In one embodiment, the composition comprises the n-butyl ester of the compound of Formula (I) and quinclorak, where the weight ratio of the n-butyl ester of the compound of Formula (I) to quinclorak is about 1:16 to about 1: 8. With respect to the methods, in certain modalities, the methods comprise contact of the unwanted vegetation or its locus or application to the soil or water to prevent the emergence or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of from about 72 grams of acid equivalent per hectare (gae / ha) to about 860 gae / ha based on the total amount of active ingredients in the composition. In certain modalities, the
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77/202 composition is applied at an application rate of from about 74 grams of acid equivalent per hectare (gae / ha) to about 645 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and quinclorak or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, the quinclorak or carboxylate salt or ester thereof is applied at a rate of from about 70 gae / ha to about 560 gae / ha and the compound of Formula (I) of the salt or ester thereof it is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In some embodiments, the quinclorak or carboxylate salt or ester thereof is applied at a rate of from about 35 gai / ha to about 1100 gai / ha and the compound of Formula (I) of salt or ester thereof it is applied at a rate of from about 2 g of acid equivalent per hectare (gae / ha) to about 170 gae / ha. In some embodiments, the quinclorak or carboxylate salt or ester thereof is applied at a rate of from about 70 gai / ha to about 560 gai / ha and the compound of Formula (I) of the salt or ester thereof it is applied at a rate of from about 4.38 g of acid equivalent per hectare (gae / ha) to about 84.8 gae / ha. In certain embodiments, the methods use the compound of Formula (I) or its benzyl or n-butyl ester and quinclorac. In one embodiment, the methods use the compound of Formula (I) and quinclorak, where the compound of Formula (I) is applied at a rate of from about 4.38 g of acid equivalent per hectare (gae / ha) at about 84.8 gae / ha, and quincloraque is applied at a rate of about 70 gai / ha to about 560 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of
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Formula (I) and quincloraque, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 4.38 g of acid equivalent per hectare (gae / ha) to about 35 gae / ha and quincloraque is applied at a rate of about 70 gai / ha to about 560 gai / ha. In one embodiment, the methods use the n-butyl ester of the compound of Formula (I) and quinclorak, where the n-butyl ester of the compound of Formula (I) is applied at a rate of about 35 g of acid equivalent per hectare (gae / ha) at about 70 gae / ha and quincloraque is applied at a rate of about 560 gai / ha. In certain embodiments, the methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with quinclorac or carboxylate salt or ester thereof are used to control CYPES, DIGSA, ECHCG, CYPIR ISCRU, ECHOR, SCPMA , AMARE, VIOTR or POLCO.
[00158] 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 triclopyr or carboxylate salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to triclopyr or carboxylate salt or ester thereof is within the range of from about 1: 1120 to about 4: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to triclopyr or carboxylate salt or ester thereof is within the range of from 1:64 to about 1: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to triclopyr or carboxylate salt or ester thereof is within the range of from about 1: 100 to about 1: 1 . In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to triclopyr or carboxylate salt or ester thereof is within the range of from about 1:44 to about
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1: 1.7. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl or butyl ester and TEA triclopi, choline triclopi or BEE triclopi. In one embodiment, the composition comprises the compound of Formula (I) and TEA triclopyr, where the weight ratio of the compound of Formula (I) to TEA triclopyr is about 1:44 to about 1: 2. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and TEA triclopyr, where the weight ratio of the benzyl ester of the compound of Formula (I) to TEA triclopyr is about 1:44 to about 1: 4. In one embodiment, the composition comprises the n-butyl ester of the compound of Formula (I) and TEA triclopyr, where the weight ratio of the n-butyl ester of the compound of Formula (I) to TEA triclopyr is about 1: 17.5. In one embodiment, the composition comprises the compound of Formula (I) and choline triclopyr, where the weight ratio of the compound of Formula (I) to choline triclopyr is about 1:28 to about 1: 1.7. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and choline triclopyr, where the weight ratio of the benzyl ester of the compound of Formula (I) to choline triclopyr is about 1:28 to about 1: 4. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and BEE triclopyr, where the weight ratio of the benzyl ester of the compound of Formula (I) to BEE triclopyr is about 1:16 to about 1: 2. Regarding methods. In certain embodiments, the methods comprise contact of unwanted vegetation or its locus or application to soil or water to prevent the emergence or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of from about 37 grams of acid equivalent per hectare (gae / ha) to about 2540 gae / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate
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80/202 from about 40 grams of acid equivalent per hectare (gae / ha) to about 325 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and triclopyr or carboxylate salt or ester thereof, for example, sequentially or simultaneously. In some embodiments, the triclopyr or carboxylate salt or ester thereof is applied at a rate of from about 35 gae / ha to about 2240 gae / ha and the compound of Formula (I) of the salt or ester thereof it is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In some embodiments, the triclopyr salt or ester thereof is TEA triclopyr, DMA triclopyr or choline salt triclopyr. In some embodiments, the triclopyr or carboxylate salt or ester thereof is applied at a rate of from about 17 gai / ha to about 600 gai / ha and the compound of Formula (I) or salt or ester thereof it is applied at a rate of from about 2 g of acid equivalent per hectare (gae / ha) to about 100 gae / ha. In some embodiments, the triclopyr or carboxylate salt or ester thereof is applied at a rate of from about 35 gai / ha to about 280 gai / ha and the compound of Formula (I) or salt or ester thereof it is applied at a rate of from about 4.38 g of acid equivalent per hectare (gae / ha) to about 42.4 gae / ha. In certain embodiments, the methods use the compound of Formula (I), or its benzyl or n-butyl ester and TEA triclopyr, choline triclopyr or BEE triclopyr. In one embodiment, the methods use the compound of Formula (I) and TEA triclopyr, where the compound of Formula (I) is applied at a rate of from about 4.38 g of acid equivalent per hectare (gae / ha ) at about 42.4 gae / ha and TEA triclopyr is applied at a rate of about 70 gai / ha to about 280 gai / ha. In
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In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and TEA triclopyr, where the benzyl ester of the compound of Formula (I) is applied at a rate from about 4.38 g of acid equivalent per hectare (gae / ha) at about 17.5 gae / ha and TEA triclopyr is applied at a rate of about 70 gai / ha to about 280 gai / ha. In one embodiment, the methods use the n-butyl ester of the compound of Formula (I) and TEA triclopyr, where the n-butyl ester of the compound of Formula (I) is applied at a rate of about 16 g of equivalent acid per hectare (gae / ha), and TEA triclopyr is applied at a rate of about 280 gai / ha. In one embodiment, the methods use the compound of Formula (I) and choline triclopir, where the compound of Formula (I) is applied at a rate of from about 4.38 g of acid equivalent per hectare (gae / ha ) at about 42.4 gae / ha and triclopyr choline is applied at a rate of about 35 gai / ha to about 140 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and choline triclopyr, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 4.38 g to acid equivalent per hectare (gae / ha) at about 17.5 gae / ha choline and triclopyr is applied at a rate of about 35 gai / ha to about 140 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and BEE triclopyr, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 4.4 g of acid equivalent per hectare (gae / ha) to about
17.5 gae / ha and BEE triclopyr is applied at a rate of about 35 gai / ha to about 70 gai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with triclopyr or carboxylate salt or ester thereof are used to control BRAPP, DIGSA, ECHCG, ECHCO, LEFCH, SCPJU, SCPMA, ECHOR, CYPRO, FIMMI, CENMA, SONAR, CIRAR or CASOB.
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82/202 [00159] 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 halauxifene-methyl (4-amino-3-chloro-6- (4chlorine -2-fluorine-3-methoxyphenyl) methyl picolinate) or carboxylic acid or carboxylate salt of the same or another ester. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to halauxifenomethyl or carboxylic acid or carboxylate salt of the same or another ester is within the range of from about 1 : 17.5 to about 600: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to halauxifene-methyl or carboxylic acid or carboxylate salt of the same or other ester is within the range of from 1: 4 to about 20: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to halauxifene-methyl or carboxylic acid or carboxylate salt of the same or other ester is within the range of about 1: 4 about 20: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to halauxifene-methyl or carboxylic acid or carboxylate salt of the same or other ester is within the range of about 1: 2 to about 9.6: 1. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl ester and halauxifene-methyl or halauxifene K ⁺ . In one embodiment, the composition comprises the compound of Formula (I) and halauxifene-methyl, where the weight ratio of the compound of Formula (I) to halauxifene-methyl is about 1: 1 to about 9.6: 1. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and halauxifene-methyl, where the weight ratio of the benzyl ester of the compound of Formula (I) to halauxifene-methyl is about 1: 2 to about 8: 1. In one embodiment, the composition comprises the benzyl ester of the compound
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83/202 of Formula (I) and halauxifene K ⁺ , where the weight ratio of the benzyl ester of the compound of Formula (I) to halauxifene K ⁺ is about 1: 2 to about 2: 1. Regarding methods. In certain embodiments, the methods comprise contact of unwanted vegetation or its locus or application to soil or water to prevent the emergence or growth of vegetation of a composition described here. In some embodiments, the composition is applied at an application rate of from about 2.5 grams of acid equivalent per hectare (gae / ha) to about 335 gae / ha based on the total amount of active ingredients in the composition . In certain embodiments, the composition is applied at an application rate of from about 6 grams of acid equivalent per hectare (gae / ha) to about 57 gae / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contact of unwanted vegetation or locus thereof or application to soil or water to prevent the emergence or growth of vegetation with a compound of Formula (I) or salt or ester thereof and halauxifene-methyl or carboxylic acid or carboxylate salt of the same or another ester, for example, sequentially or simultaneously. In some embodiments, halauxifene-methyl or carboxylic acid or carboxylate salt of the same or another ester is applied at a rate from about 0.5 gae / ha to about 35 gae / ha and the compound of Formula (I ) of salt or ester thereof is applied at a rate of from about 2 gae / ha to about 300 gae / ha. In some embodiments, halauxifene-methyl or carboxylic acid or carboxylate salt of the same or another ester is applied at a rate from about 1 gai / ha to about 30 gai / ha and the compound of Formula (I) of salt or ester of the same is applied at a rate of from about 1 g of acid equivalent per hectare (gae / ha) to about 100 gae / ha. In some embodiments, halauxifene-methyl or carboxylic acid or salt
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84/202 of carboxylate of the same or another ester is applied at a rate of from about 2.19 gai / ha to about 15 gai / ha and the compound of Formula (I) of salt or ester of the same is applied at a rate of from about 3.75 g of acid equivalent per hectare (gae / ha) to about
42.4 gae / ha. In certain embodiments, the methods use the compound of Formula (I), or its benzyl ester and halauxifene-methyl or halauxifene K ⁺ . In one embodiment, the methods use the compound of Formula (I) and halauxifene-methyl, where the compound of Formula (I) is applied at a rate of from about 4.38 g of acid equivalent per hectare (gae / ha) at about 42.4 gae / ha and halauxifene-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 halauxifene-methyl, where the benzyl ester of the compound of Formula (I) is applied at a rate of from about 3.75 g of acid equivalent per hectare (gae / ha) to about 17.5 gae / ha and halauxifene-methyl is applied at a rate of about 2.19 gai / ha to about 15 gai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and halauxifene K +, where the benzyl ester of the compound of Formula (I) is applied at a rate of about 3.75 g of acid equivalent per hectare (gae / ha) at about 42 gae / ha and K + halauxifene is applied at a rate of about 3.75 gai / ha to about 15 gai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with halauxifene-methyl or carboxylic acid or carboxylate salt of the same or another ester are used to control LEFCH, IPOHE, CYPIR, ECHCG, ECHOR, CYPRO, ELEIN or SORHA. [00160] The components of the mixtures described here can be applied either separately or as part of a multipart herbicide system.
[00161] The mixtures described here can be applied together
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85/202 with one or more other herbicides to control a greater variety of undesirable vegetation. When used in conjunction with other herbicides, 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 conjunction with the compositions and methods described here include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 3,4-DA; 3,4-DB; 2,4-DEB; 2,4-DEP;
3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifene, acrolein, alachlor, alidochlor, aloxidim, allyl alcohol, alorak, ametridione, amethrine, amibuzim, amicarbazone, amidosulfuron, amiprofos-methyl, amitrol, ammonium sulfamate, azimsulfuride, aziproxide, aziprotoxin benazoline, bencarbazone, benfluralin, benfuresate, benssulfurom-methyl, bensulide, bentiocarb, bentazom-sodium, benzadox, benzfendizone, benzipram, benzobicyclone, benzofenape, benzofluor, benzoilprope, benztiazuron, biphenyl, biphenyl, biphenyl, biphazone bromacila, bromobonyl, bromobutide, bromophenoxin, bromoxynil, brompyrazone, butachlor, butafenacil, butamiphos, butenachlor, butidazole, butiurom, butralin, butroxidim, buturom, butylate, cacodyl acid, calcium, carbamide, chloride, carbamide, chloride, chloride, chloride , chlorprocarb carboxazole, carfentrazone-ethyl, CDEA, CEPC, clomethoxyfen, chloramben, chloranocril, chlorazifop, chlorazine, chlorobromuron , chlorinate, chloreturon, chlorfenac, chlorfenprope, chlorflurazole, chlorflurenol, chloridazone, chlorimuron, chlorornitrophen, chloropom, chlorotoluron, chloroxuron, chloroxynil, chlorprofam, chlorhlorurom, chloride, chlorhedamine, cinodilope, cinidonethin, cinidone -propargyl, clofope, clomazone, cloprope, cloproxidim, chloransulam-methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumiluron, cyanatrine,
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86/202 cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxidim, cycluron, cyhalofop-butyl, cyperquate, cyprazine, cyprazole, cypromide, daimurom, dalapom, dazomete, delachlor, demedifiline, dicloforine, dichlorohydrate, diclofenate, diclofenate, diclofenate, diclofenate, diclofenate , diclosulam, dietamquate, diethyl, diphenopentene, diphenoxuron, difenzoquate, diflufenicam, diflufenzopyr, dimefuron, dimepiperate, dimetachlor, dimetamethrin, dimethenamide, P-dimexane, dimidazonine, dinopyrine, dinide, dinide, dinopyrine, dinide, dinopyrine, dinopamine ; , etnipromide, etobenzanide, EXD, fenasulam, fenoprope, phenoxaprope, phenoxaprop-P-ethyl, phenoxaprope-P-ethyl + isoxadifen-ethyl, phenoxasulfone, phenteracol, fentiaprope, fentrazamide, phenuron, ferrous sulfate, flamprope, flamprope-M, flazasulfurom, florasulam, fluazifope, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfurom, flufenacet, flufenicam, flufen-flum, flufen, flufen, , flumipropyn, fluometuron, fluordifene, fluorglicofene, fluormidine, fluornitrofen, fluotiurom, flupoxam, flupropacil, flupropanate, flupirsulfuron, fluridone, flurochloridone, flurtamone, flutiacetum, fomesafene, foramsulfuroxide, glumphonate, glumumine, glomerulone -ammonium, glyphosate, halosafen, halosulfurom-methyl, haloxidine, haloxifop-methyl, haloxifop-P-methyl, hexachloroacetone, hexaflurate, hexazinone, imazametabenz, imazamox, imazapique, imazapir, imazamametam, imazapam, imazanamim, imazanam, , iodosulfuron, iodosulfurom-ethyl-sodium, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprimidam, isocarbamide, isocyl, isomethiozine, isonoruron, isopolinate, isopropalin, isoproturon,
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87/202 isourom, isoxabem, isoxaclortol, isoxaflutol, isoxapyrifope, carbutilate, cetospiradox, lactofen, lenacil, linurom, MAA, MAMA, MCPB, medinoterb, mefenacete, mefluidide, mesoprazine, metosulfuram, metosulfurom, metosulfurom, metosulfurom, metosulfurom, metosulfurom, metotrifamom, , metflurazon, metabenztiazuron, metallopralin, metazol, methiobencarb, methiozoline, methuron, metometom, methoprotrin, methyl bromide, methyl isothiocyanate, methyldrom, metobenzurom, metobromuron, metolachur, metolachur, metolachin, metholomide, metholone, metholone, , monisourom, monochloroacetic acid, monolinuron, monurom, morfamquate, MSMA, naproanilide, napropamide, naptalam, neburom, nicosulfurom, nipyraclofen, nitralin, nitrophen, nitrofluorfen, norflurazon, noruromine, oruror, orbencar, orbencar, orbencar oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl, paraflurom, paraquat, pebulate, pelaric acid gonic, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, petoxamide, fenisofam, fenmedifam, fenmedifam-ethyl, fenobenzurom, phenylmercury acetate, picolinafen, pinoxadem, piperofos, potassium arsenite, potassium arsenite, potassium arsenite, potassium arsenite -methyl, prociazine, prodiamine, profluazole, profluralin, profoxidim, proglinazine, prhexadione-calcium, prometom, promethrin, pronamide, propachlor, propanyl, propaquizafope, propazine, profam, propisochlor, propoxycarbazone, propirisulfuron, propiramx, pros prosxide , prinaclor, pidanon, piraclonil, piraflufen-ethyl, pirasulfotol, pyrazogil, pyrazolinate, pyrazosulfuron-ethyl, pyrazoxifene, pyribenzoxim, pyributicarb, pyrichloride, pyrimoxane, pyrimoxane, pyrimisulfan, pyrimisulfan, pyrimoxyramine, pyrimoxane, pyrimoxyramine, pyrimoxane , quinonamide, quizalofope, quizalofope-P-ethyl, rhodetanil, rimsulfurom, saflufe nacil, S
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88/202 metolachlor, sebutilazine, secbumetom, setoxidim, sidurom, simazine, simeton, symmetry, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfalate, sulfentrazone, sulfometurom, sulfosate, sulfosulfuron, sulfuric acid, sulglicaphos swep, SIN-523, TCA, tebutam, tebutiurom, tefuriltrione, tembotrione, tepraloxidim, terbacil, terbucarb, terbuclor, terbumetom, terbutilazine, terbutrin, tetraflurom, tenilclor, thiazaflurom, tzurimidia, tzurimia, tzurimia, tzurzone thiobencarb, thiocarbazil, thioclorin, topramezone, tralcoxidim, triafamone, tri-alate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricamba, tridifana, trietazine, trifloxysulfuron, trifloxytrim, triflopine, triflopine, triflopine , vernolate, xylachlor and salts, ester, optically active isomers and mixtures thereof.
[00162] The compositions and methods described here can also be used in conjunction with glyphosate, 5enolpyruvylshiquime-3-phosphate (EPSP) synthase, glufosinate, glutamine synthetase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, inhibitors transport of auxin, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolpyrimidines, sulfonylaminocarbonyltriazolinides, (4) -hydroxyphenylpyruvate dioxigenase (HPPD), phytoene desaturase inhibitor, carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase (PPO) inhibitor, cellulose biosynthesis inhibitors, mitosis inhibitor, microtubule inhibitors, very long chain fatty acid inhibitors of biosynthesis of fatty acid and lipid, inhibitors of photosystem I, photosystem II inhibitors, triazines, and bromoxynil
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89/202 glyphosate tolerant, tolerant to EPSP synthase inhibitor, tolerant to glufosinate, tolerant to glutamine synthase inhibitor, tolerant to dicamba, tolerant to phenoxy-auxin, tolerant to pyridyloxy auxin, tolerant to auxin, tolerant to transport inhibitor auxin, tolerant to aryloxyphenoxypropionate, tolerant to cyclohexanedione, tolerant to phenylpyrazoline, tolerant to ACCase, tolerant to imidaizolinone, tolerant to sulphonylurea, tolerant to pyrimidinylthiobenzoate, tolerant to triazolpyrimidine, tolerant to ALS, tolerant to ALH , tolerant to phytene 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 inhibitor I, tolerant to photosystem inhibitor II, tolerant to triazine, tolerant to bromoxynil and cultures presenting multiple or stacked characteristics conferring tolerance to multiple chemicals and / or multiple modes of action through simple and / or multiple resistance mechanisms. 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 employed. In some embodiments, the compositions described here and other complementary herbicides are applied at the same time, either as a combination formulation or as a tank mixture.
[00163] 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,
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90/202 brassinolid, cloquintocete (mexila), ciometrinila, daimurom, diclormide, dicyclonone, dimepiperate, disulfoton, fenclorazol-ethyl, fenclorim, flurazol, fluxofenim, furilazol, hairpin proteins, isoxadiphenyethyl, ji, ji, ji, ji, ji , mefenate, naphthalic anhydride (NA), oxabetrinyl, R29148 and amides of M-phenylsulfonylbenzoic acid to increase their selectivity. In some modalities, protectors are used in rice, cereal or corn locations. In some modalidaides, the protector is cloquintocete or an ester or salt of the same. In certain embodiments, cloquintocet is used to antagonize harmful effects of the compositions on rice and cereals. In some modalities, the protector is cloquintocete (mexila).
[00164] In some embodiments, the compositions described here are used in combination with one or more plant growth regulators, such as 2,3,5-triiodiodobenzoic acid, IAA, IBA, naphthalene acetamide, α-naphthalene acetic acids, benzyladenine alcohol
4-hydroxyphenethyl, quinetin, zeatin, endothal, ethephon, pentachlorophenol, thiadiazuron, tribufos, aviglycine, ethephon, maleic hydrazide, gibberellins, gibberellic acid, abscisic acid, ancimidol, phosamine, glyphosine, isopyrimole, jasmine, acid, jasmine; 2,3,5triiodobenzoic, morphactins, dichlorflurenol, flurprimidol, mefluidide, paclobutrazol, tetciclacis, uniconazole, brassinolide, brassinolide-ethyl, cyclohexide, ethylene, metasulfocarb, proexadione, triaxentaphenol and triaxentenol and triaxentenol.
[00165] In some embodiments, plant growth regulators are used in one or more crops or environments, such as rice, cereal crops, corn, broadleaf crops, oil / canola seed rape, peat, pineapple, sugar cane, sunflower, steps, grassland, pasture, fallow, peat, tree and vine orchards, plantation crops, plant environments and non-culture (ornamental). In some modalities, the growth regulator
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91/202 of plant is mixed with the compound of Formula (I) or mixed with the compound of Formula (I) and synthetic auxins to cause a preferentially beneficial effect on plants.
[00166] In some modalidaides, 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 selective weed control compositions 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 locus or they can be concentrated or formulations that are normally diluted with additional vehicles or adjuvants before application. They can be solids such as, for example, fine powders, granules, water-dispersible granules or wetting powders, or liquids such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be provided as a premix or mixed in a tank.
[00167] Suitable agricultural adjuvants and vehicles include, but are not limited to, culture oil concentrate; nonylphenol ethoxylate; benzylcocoalkylldimethyl quaternary ammonium salt; mixture of petroleum hydrocarbon, alkyl esters, organic acid and anionic surfactant: C9-C11 alkylpolyglycoside; phosphate alcohol ethoxylate; natural primary alcohol ethoxylate (C12-C16); EPPO block copolymer of di-sec-butylphenol; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol ethoxylate (synthetic) (8EO); tallow amine ethoxylate (15 EO); dioleate-99 PEG (400).
[00168] Liquid vehicles that can be used include water
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92/202 and organic solvents. Organic solvents include, but are not limited to, petroleum or hydrocarbon fractions such as mineral oil, aromatic solvents, paraffinic oils and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, flaxseed oil, palm, 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 4-6 hydroxy), such as 2-ethyl hexyl stearate, nbutyl oleate, isopropyl myristate, propylene glycol dioleate, dioctyl succinate, dioctyl adipate -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 propylene glycol ether and monomethyl diethylene glycol ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerin, V-methyl-2-pyrrolidionone, M, M-dimethyl alkylamides, sulfoxide dimethyl, liquid fertilizers and the like. In certain embodiments, water is the vehicle for diluting concentrates.
[00169] Suitable solid vehicles include, but are not limited to, pyrophyllite clay, silica, atapulgus clay, kaolin clay, diatomaceous earth, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, fuller earth, seed husks cotton, wheat flour, soy flour, porcine flour, wood flour, nutshell flour, lignin, cellulose and the like.
[00170] In some embodiments, the compositions described here further comprise one or more surfactants. In some
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93/202 modalities, surfactants are used in both solid and liquid compositions and in certain modalities in those designed to be diluted with a vehicle before application. Surfactants 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. Surfactants include, but are not limited to, alkyl sulfate salts, such as diethylammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-Cw ethoxylate; soaps, such as sodium stearate; alkyl naphthalene sulfonate salts, such as sodium dibutyl naphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di (2-ethylexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as trimethylammonium lauryl chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; such 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, flaxseed, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils, and in certain embodiments, methyl esters.
[00171] In some modalities, these materials, such as oils
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94/202 vegetable or seed and their esters, can be used interchangeably as an agricultural adjuvant, as a liquid vehicle or as a surfactant.
[00172] Other exemplary additives for use in the compositions provided herein include, but are not limited to, compatibilizing agents, defoaming agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, tackifiers, 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 or solid fertilizers, particulate fertilizer vehicles such as ammonium nitrate, urea and the like.
[00173] In some embodiments, the concentration of active ingredients in the compositions described here is from about 0.0005 to 98 weight percent. In some embodiments, the concentration is from about 0.0006 to 90% by weight. In compositions designed to be used as concentrates, the active ingredients, in certain modalities, are present in a concentration of from about 0.1 to 98 weight percent and in certain modalities 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 generally applied to weeds or the weed site contain, in certain embodiments, about 0.0006 to 3.0 weight percent of active ingredient and in certain embodiments contain about 0.01 to 1.0 percent in weight.
[00174] The present compositions can be applied to herbs
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95/202 weeds or to their location through the use of conventional atomizers, sprayers and ground or aerial granule applicators, through the addition to irrigation or rice water and through other conventional means known to those skilled in the art.
[00175] The modalities described and the examples that follow 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 apparent to a common person skilled in the art without departing from the spirit and scope of the claimed object matter.
Examples [00176] The results in Examples I, II, III, IV and V are greenhouse test results.
Example I. Evaluation of Herbicidal Mixtures Applied to Post-emergence Foliage for Weed Control in Direct Seeded Rice [00177] Seeds or small nuts of the desired test plant species were planted in a soil matrix prepared by mixing a clay or sandy clay (for example, 28.6 percent mud, 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 powder limestone in an 80 to 20 ratio. The soil matrix was contained in plastic pots with a volume of 1 quarter and a surface area of
83.6 square centimeters (cm ² ). When necessary to ensure good germination and healthy plants, a treatment with fungicide and / or other chemical agent or physical treatment was applied. The plants were grown for 8-22 days in a greenhouse with an approximate photoperiod of 14 h that was maintained at about 29 ° C during the day and 26 ° C at night. Nutrients (Peters Excel® 15-5-15 5-Ca- 2 Mg and iron chelate)
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96/202 were applied to the irrigation solution as needed and water was added on a regular basis. Supplementary light 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.
[00178] The treatments consisted of 4 amino-3-chloro-5-fluor-6- (4-chloro-2-fluor-3-methoxy-phenyl) pyridine-2-carboxylic acid or esters (Compound A), each formulated as a SC (Suspension Concentrate) and various herbicidal components alone or in combination. Compound A forms were applied on an acid equivalent basis.
[00179] The forms of Compound A (compound of Formula I) tested include:
nh ₂ cr
OH
Compound A Acid
N
Cl
O
O
Compound A n-Butyl ester
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Compound A Benzyl Ester [00180] Other herbicidal components were applied on an acid equivalent base or active ingredient base and included 2,4-D dimethylammonium (DMA) salt formulated as Weedar® 64, Choline salt 2.4 -D formulated as a soluble liquid (SL) (Soluble Liquid),
2,4-D 2-ethyl hexyl ester (EHE) formulated as an SL, MCPA K + / Na + / DMA salt formulated as Agritox® 50, MCPA ethyl hexyl ester formulated as MCPA2®, methyl heptyl ester (MHE) fluroxypyr formulated as Starane ^® or Starane ^® Ultra, triethylamine triclopyr (TEA) salt formulated as Grandstand® R, triclopyr choline salt formulated as an SL, tricloprir butotyl ester formulated as an EC, formulated dimethylammonium salt (DMA) formulated like Banvel® 4S, quincloraque formulated as Facet ^® 75DF and halauxifene-methyl formulated as a SC (suspension concentrate).
[00181] Treatment needs were calculated based on the rates being tested, the concentration of active ingredient or acid equivalent in the formulation and an application volume of 12 mL at a rate of 187 L / ha.
[00182] For treatments comprised of formulated compounds, the measured amounts of compounds were individually placed in 25 ml glass bottles and diluted in a volume of 1.25% (v / v) of Agri-Dex® culture oil concentrated to get 12X stock solutions. If a test compound did not immediately dissolve, the mixture was heated and / or sonicated. Application solutions have been prepared
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98/202 by adding an appropriate amount of each stock solution (eg 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of 1.25% (v / v) aqueous mixture of concentrate of culture oil so that the final spray solutions contained 1.25 +/- 0.05% (v / v) of culture oil concentrate.
[00183] For treatments comprised of technical compounds, weighted amounts can be placed individually in 25 ml glass bottles and dissolved in a 97: 3 v / v acetone / DMSO volume to obtain 12X stock solutions. If a test compound does not readily dissolve, the mixture can be heated and / or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (for example, 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of a 1.5% (v / v) culture oil concentrate so that the final spray solutions contain 1.25% (v / v) culture oil 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.
[00184] For treatments comprised of formulated and technical compounds, weighted amounts of technical materials can be placed individually in 25 mL glass bottles and dissolved in a 97: 3 v / v volume of acetone / DMSO to obtain 12X stock solutions and the measured quantities of the formulated compounds can be placed individually in 25 ml glass bottles and diluted in a volume of 1.5% (v / v) of culture oil or water concentrate to obtain 12X stock solutions. If a test compound does not readily dissolve, the mixture can be heated and / or sonicated.
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Application solutions can be prepared by adding an appropriate amount of each stock solution (for example, 1 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of a 1.5% aqueous mixture (v / v) culture oil concentrate so that the final spray solution contains 1.25% (v / v) culture oil concentrate. As needed, additional water and / or 97: 3 v / v acetone / DMSO can be added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared are 8.1% and 0, 25%, respectively.
[00185] All stock solutions and application solutions were visually inspected for compound compatibility prior to application. Spray solutions were applied to the plant material with a suspended Mandel strip sprayer equipped with 8002E nozzles calibrated to apply 187 L / ha in an application area of 0.503 m ² at a spray height of 46 to 50 cm (18 to 20 in) above the canopy height of the average plant. Control plants were sprayed in the same way with the solvent without activity.
[00186] The treated plants and the control plants were placed in a greenhouse as described above and irrigated by sub-irrigation to prevent runoff of the test compounds. After approximately 3 weeks, the condition of the test plants compared to that of the untreated plants was determined visually and rated on a scale of 0 to 10 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete death.
[00187] Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R., 1967,
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Calculation of the synergistic and antagonistic response of herbicide combinations, Weeds 15: 20-22).
[00188] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B / 100)
A = observed effectiveness of active ingredient A in the same concentration as used in the mixture.
B = observed effectiveness of active ingredient B at the same concentration as that used in the mixture.
[00189] The tested compounds, application rates employed, species of plant tested and results are given in Tables 1-26.
Table 1. Synergistic Activity of Herbicidal Compositions of Compound A Acid and 2,4-D Dimethylammonium Salt (DMA) on Weed Control in a Rice Culture System.
AcidCompound A DMA salt2,4-D Visual Weed Control (%) -19 DAA ECHCG gae / ha gae / ha Note Exp 4.38 0 60 - 0 70 0 - 0 140 10 - 0 280 25 - 4.38 70 75 60 4.38 140 75 64 4.38 280 75 70
Table 2. Synergistic activity of Compound A Benzyl Ester Herbicidal Compositions and Dimethylammonium Salt (DMA) 2,4-D Applied to Leaf on Weed Control in a Culture System
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Benzyl Ester of Compound A DMA salt2,4-D Visual Weed Control(%) - 19 DAA ECHCG gae / ha gae / ha Note Exp 4.38 0 55 - 0 70 0 - 0 140 10 - 0 280 25 - 4.38 70 70 55 4.38 140 80 60 4.38 280 70 66
Table 3. Synergistic Activity of Herbicidal Compositions of Compound A and Choline Salt 2,4-D Applied to Leaf on Weed Control in Rice Culture System.
AcidCompound A Choline salt 2,4-D Visual Weed Control (%) -20 DAA DIGSA gae / ha gae / ha Note Exp 4.38 0 30 - 17.5 0 40 - 0 105 0 - 0 210 0 - 0 420 10 - 4.38 105 40 30 17.5 105 70 40 4.38 210 50 30
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AcidCompound A Choline salt 2,4-D Visual Weed Control (%) -20 DAA DIGSA gae / ha gae / ha Note Exp 17.5 210 75 40 4.38 420 50 37 17.5 420 65 46
AcidCompound A Choline salt 2,4-D Visual Weed Control (%) -20 DAA ECHCO gae / ha gae / ha Note Exp 4.38 0 65 - 8.75 0 85 - 0 105 10 - 0 210 30 - 4.38 105 90 69 8.75 105 90 87 4.38 210 90 76 8.75 210 95 90
AcidCompound A Choline salt 2,4-D Visual Weed Control (%) -20 DAA CIPES gae / ha gae / ha Note Exp 4.38 0 80 - 8.75 0 95 -
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AcidCompound A Choline salt 2,4-D Visual Weed Control (%) -20 DAA CIPES gae / ha gae / ha Note Exp 0 105 0 - 0 210 0 - 0 420 0 - 4.38 105 95 80 8.75 105 100 95 4.38 210 90 80 8.75 210 100 95 4.38 420 100 80 8.75 420 100 95
AcidCompound A Choline salt 2,4-D Visual Weed Control (%) -20 DAA CIPIR gae / ha gae / ha Note Exp 4.38 0 40 - 0 105 50 - 0 210 100 - 0 420 70 - 4.38 105 100 70 4.38 210 100 100 4.38 420 100 82
Table 4. Synergistic effect of Herbicidal Compositions of Benzyl Ester of Compound A and Choline Salt 2,4-D applied to the leaf on
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Weed Control in a Rice Culture System.
Benzyl Ester of Compound A Choline salt 2,4-D Visual Weed Control(%) - 20 DAA DIGSA gae / ha gae / ha Note Exp 4.38 0 50 - 8.75 0 60 - 17.5 0 70 - 0 420 10 - 4.38 420 65 55 8.75 420 70 64 17.5 420 99 73
Benzyl Ester of Compound A Choline salt 2,4-D Visual Weed Control(%) - 20 DAA ECHCG gae / ha gae / ha Note Exp 4.38 0 70 - 8.75 0 70 - 17.5 0 95 - 0 105 10 - 4.38 105 95 73 8.75 105 99 73 17.5 105 99 96
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Benzyl Ester of Compound A Choline salt 2,4-D Visual Weed Control(%) - 20 DAA ECHCO gae / ha gae / ha Note Exp 4.38 0 60 - 8.75 0 85 - 0 105 10 - 0 210 30 - 4.38 105 85 64 8.75 105 90 87 4.38 210 85 72 8.75 210 95 90
Table 5. Synergistic activity of Compound A Acid Herbicidal Compositions and Ethyl Hexyl Ester (EHE) 2,4-D Applied to Foliage under Weed Control in a Rice Culture System.
AcidCompound A 2,4-D EHE Visual Weed Control (%) -23 DAA BRAPP gae / ha gae / ha Note Exp 4.38 0 40 - 8.75 0 55 - 0 70 0 - 0 140 0 - 0 280 0 - 4.38 70 55 40 8.75 70 65 55 4.38 140 55 40
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AcidCompound A 2,4-D EHE Visual Weed Control (%) -23 DAA BRAPP gae / ha gae / ha Note Exp 8.75 140 65 55 4.38 280 60 40 8.75 280 70 55
AcidCompound A 2,4-D EHE Visual Weed Control (%) -23 DAA ECHCO gae / ha gae / ha Note Exp 4.38 0 15 - 0 70 0 - 0 140 0 - 0 280 40 - 4.38 70 50 15 4.38 140 65 15 4.38 280 85 49
AcidCompound A 2,4-D EHE Visual Weed Control (%) -23 DAA DIGSA LEFCH gae / ha gae / ha Note Exp Note Exp 4.38 0 0 - 0 - 8.75 0 0 - 0 - 17.5 0 10 - 15 -
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AcidCompound A 2,4-D EHE Visual Weed Control (%) -23 DAA DIGSA LEFCH gae / ha gae / ha Note Exp Note Exp 0 70 0 - 20 - 0 140 0 - 25 - 0 280 0 - 30 - 4.38 70 30 0 55 20 8.75 70 35 0 50 20 17.5 70 25 10 65 32 4.38 140 40 0 65 25 8.75 140 30 0 60 25 17.5 140 60 10 80 36 4.38 280 15 0 55 30 8.75 280 15 0 45 30 17.5 280 25 10 85 41
Table 6. Synergistic activity of Herbicidal Compositions of Benzyl Ester of Compound A and Ethyl Hexyl Ester (EHE) 2,4-D Applied to Foliage under Weed Control in a Rice Culture System.
Benzyl Ester of Compound A 2,4-DEHE Visual Weed Control (%)- 23 DAA DIGSA ECHCO gae / ha gae / ha Note Exp Note Exp 4.38 0 0 - 40 - 8.75 0 0 - 40 -
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Benzyl Ester of Compound A 2,4-DEHE Visual Weed Control (%)- 23 DAA DIGSA ECHCO gae / ha gae / ha Note Exp Note Exp 17.5 0 15 - 75 - 0 70 0 - 0 - 0 140 0 - 0 - 0 280 0 - 40 - 4.38 70 20 0 50 40 8.75 70 25 0 65 40 17.5 70 35 15 70 75 4.38 140 25 0 55 40 8.75 140 25 0 75 40 17.5 140 35 15 85 75 4.38 280 60 0 60 64 8.75 280 40 0 80 64 17.5 280 60 15 100 85
Benzyl ester ofCompound A 2,4-D EHE Weed ControlVisual (%) - 23 DAA LEFCH gae / ha gae / ha Note Exp 4.38 0 20 - 8.75 0 20 - 17.5 0 45 - 0 70 20 - 0 280 30 - 4.38 70 75 36
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Benzyl ester ofCompound A 2,4-D EHE Weed ControlVisual (%) - 23 DAA LEFCH gae / ha gae / ha Note Exp 8.75 70 80 36 17.5 70 55 56 4.38 280 70 44 8.75 280 80 44 17.5 280 80 62
Benzyl ester ofCompound A 2,4-D EHE Weed ControlVisual (%) - 23 DAA CIPES gae / ha gae / ha Note Exp 4.38 0 85 - 0 70 0 - 0 140 0 - 0 280 0 - 4.38 70 100 85 4.38 140 100 85 4.38 280 95 85
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Table 7. Synergistic activity of Compound A Acid and MCPA Herbicidal Compositions (K + / NA + / DMA Salt) Applied to Foliage on Weed Control in Rice Culture System.
AcidCompound A Salt ofMCPA Visual Weed Control (%) - 21 DAA DIGSA gae / ha gai / ha Note Exp 4.38 0 35 - 8.75 0 50 - 17.5 0 40 - 0 70 0 - 0 140 0 - 4.38 70 50 35 8.75 70 60 50 17.5 70 50 40 4.38 140 60 35 8.75 140 50 50 17.5 140 60 40
AcidCompound A Salt ofMCPA Visual Weed Control (%) - 21DAA ECHCG gae / ha gai / ha Note Exp 4.38 0 15 - 8.75 0 50 - 0 70 0 - 0 140 0 - 4.38 70 75 15
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Acid Salt of Visual Weed Control (%) - 21 Compound A MCPA DAA ECHCG gae / ha gai / ha Note Exp 8.75 70 70 50 4.38 140 65 15 8.75 140 70 50
AcidCompound A Salt ofMCPA Visual Weed Control (%) - 21 DAA LEFCH gae / ha gai / ha Note Exp 17.5 0 0 - 0 70 0 - 0 140 0 - 17.5 70 40 0 17.5 140 50 0
Table 8. Synergistic activity of Compound A Benzyl Ester Herbicidal Compositions and MCPA (K + / Na + / DMA Salt) Applied to Foliage on Weed Control in a Rice Culture System.
Benzyl Ester of Compound A Salt ofMCPA Visual Weed Control (%) - 21 DAA BRAPP gae / ha gai / ha Note Exp 4.38 50 50 - 0 70 0 -
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Benzyl Ester of Compound A Salt ofMCPA Visual Weed Control (%) - 21 DAA BRAPP gae / ha gai / ha Note Exp 0 140 0 - 4.38 70 65 50 4.38 140 65 50
Benzyl Ester of Compound A Salt ofMCPA Visual Weed Control (%) -21 DAA DIGSA ECHCG gae / ha gai / ha Note Exp Note Exp 4.38 0 50 - 10 - 8.75 0 35 - 85 - 0 70 0 - 0 - 0 140 0 - 0 - 4.38 70 60 50 80 10 8.75 70 50 35 90 85 4.38 140 50 50 70 10 8.75 140 60 35 85 85
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Table 9. Synergistic activity of Compound A Benzyl Ester Herbicidal Compositions and MCPA Ethyl Hexyl Ester Applied to Foliage under Weed Control in a Rice Culture System.
Ester ofBenzila doCompound A MCPAEHE Visual Weed Control (%) - 22 DAA DIGSA ECHCG LEFCH gae / ha gai / ha Note Exp Note Exp Note Exp 8 0 10 - 35 - 15 - 16 0 15 - 65 - 50 - 32 0 30 - 80 - 60 - 0 70 0 - 0 - 0 - 0 140 0 - 0 - 0 - 0 280 0 - 0 - 0 - 8 70 10 10 60 35 30 15 16 70 30 15 85 65 70 50 32 70 50 30 95 80 75 60 8 140 15 10 80 35 30 15 16 140 25 15 90 65 55 50 32 140 40 30 95 80 65 60 8 280 40 10 65 35 40 15 16 280 50 15 90 65 70 50 32 280 55 30 95 80 75 60
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Table 10. Synergistic activity of Herbicidal Compositions of Compound A n-Butyl Ester and Hexyl Ethyl Ester (EHE) MCPA Applied to Foliage on Weed Control in a Rice Culture System.
Compound n-Butyl ester MCPAEHE Visual Weed Control (%) - 20 DAA DIGSA ECHCG gae / ha gai / ha Note Exp Note Exp 16 0 15 - 65 - 0 280 20 - 40 - 16 280 45 32 97 79
Table 11. Synergistic activity of Herbicidal Compositions of Compound A Acid and Triethylamine Salt (TEA) triclopir Applied to Foliage on Weed Control in a Rice Culture System.
AcidCompound A TEA Triclopir salt Visual Weed Control (%) - 21DAA BRAPP gae / ha gae / ha Note Exp 4.38 0 50 - 0 98.3 0 - 0 196.6 0 - 4.38 98.3 80 50 4.38 196.6 65 50
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AcidCompound A TEA Triclopir salt Visual Weed Control (%) - 21 DAA DIGSA gae / ha gae / ha Note Exp 4.38 0 35 - 8.75 0 50 - 17.5 0 40 - 0 98.3 0 - 4.38 98.3 60 35 8.75 98.3 65 50 17.5 98.3 65 40
AcidCompound A TEA Triclopir salt Visual Weed Control (%)- 21 DAA ECHCG ECHCO gae / ha gae / ha Note Exp Note Exp 4.38 0 15 - 70 - 8.75 0 50 - 75 - 0 98.3 30 - 0 - 0 196.6 20 - 0 - 4.38 98.3 65 41 70 70 8.75 98.3 95 65 85 75 4.38 196.6 90 32 90 70 8.75 196.6 95 60 90 75
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AcidCompound A TEA Triclopir salt Visual Weed Control (%) -21 DAA LEFCH gae / ha gae / ha Note Exp 8.75 0 0 - 17.5 0 0 - 0 196.6 0 - 8.75 196.6 20 0 17.5 196.6 35 0
AcidCompound A TEA Triclopir salt Visual Weed Control (%) - 19 DAA LEFCH gae / ha gae / ha Note Exp 19.4 0 5 - 0 280 20 - 19.4 280 60 24
Table 12. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Triethylamine Salt (TEA) Triclopir Applied to Foliage under Weed Control in a Rice Culture System.
Ester ofBenzila doCompound A TEA Triclopir salt Visual Weed Control (%) -21 DAA ECHCG ECHCO gae / ha gae / ha Note Exp Note Exp 4.38 0 10 - 70 -
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Ester ofBenzila doCompound A TEA Triclopir salt Visual Weed Control (%) -21 DAA ECHCG ECHCO gae / ha gae / ha Note Exp Note Exp 8.75 0 85 - 75 - 0 98.3 30 - 0 - 0 196.6 20 - 0 - 4.38 98.3 65 37 85 70 8.75 98.3 95 90 90 75 4.38 196.6 70 28 85 70 8.75 196.6 90 88 85 75
Benzyl Ester of Compound A TEA riclopir salt Visual Weed Control(%) - 19 DAA DIGSA gae / ha gae / ha Note Exp 16 0 18 - 0 280 55 - 16 280 78 63
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Table 13. Synergistic Activity of Herbicidal Compositions of Compound A n-Butyl Ester and Triethylamine Salt (TEA) Triclopyr Applied to Foliage under Weed Control in a Rice Culture System.
N-Butyl ester TEA salt Visual Weed Control of Compound A Triclopir (%) - 19 DAA LEFCH gae / ha gae / ha Note Exp 16 0 10 - 0 280 20 - 16 280 68 28
Table 14. Synergistic Activity of Herbicidal Compositions of Compound A and Triclopir Choline Salt Applied to Foliage under Weed Control in a Rice Culture System.
AcidCompound A Hill SaltTriclopir Visual Weed Control (%) -21 DAA ECHCG gae / ha gae / ha Note Exp 5.3 0 65 - 10.6 0 55 - 0 35 0 - 0 70 0 - 0 140 0 - 5.3 35 55 65 10.6 35 70 55 5.3 70 70 65 10.6 70 55 55 5.3 140 80 65
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AcidCompound A Hill SaltTriclopir Visual Weed Control (%) -21 DAA ECHCG gae / ha gae / ha Note Exp 10.6 140 60 55
AcidCompound A Hill SaltTriclopir Visual Weed Control (%) - 21 DAA DIGSA LEFCH gae / ha gae / ha Note Exp Note Exp 5.3 0 10 - 0 - 10.6 0 10 - 10 - 21.2 0 15 - 10 - 0 35 0 - 0 - 0 70 10 - 20 - 0 140 20 - 0 - 5.3 35 20 10 15 0 10.6 35 30 10 30 10 21.2 35 40 15 80 10 5.3 70 10 19 20 20 10.6 70 60 19 25 28 21.2 70 75 24 60 28 5.3 140 55 28 20 0 10.6 140 50 28 20 10 21.2 140 60 32 60 10
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AcidCompound A Hill SaltTriclopir Visual Weed Control (%) - 21 DAA SCPJU gae / ha gae / ha Note Exp 5.3 0 60 - 10.6 0 75 - 0 35 0 - 0 70 50 - 5.3 35 99 60 10.6 35 100 75 5.3 70 99 80 10.6 70 99 88
Table 15. Synergistic Activity of Compound A Benzyl Ester Herbicidal Compositions and Triclopir Choline Salt Applied to Foliage under Weed Control in a Rice Culture System.
Ester ofBenzila doCompound A Hill SaltTriclopir Visual Weed Control (%) - 21 DAA ECHCG ECHCO gae / ha gae / ha Note Exp Note Exp 4.38 0 40 - 30 - 8.75 0 60 - 55 - 0 35 0 - 0 - 0 70 0 - 0 - 0 140 0 - 0 - 4.38 35 60 40 50 30 8.75 35 60 60 60 55 4.38 70 45 40 75 30
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Ester ofBenzila doCompound A Hill SaltTriclopir Visual Weed Control (%) - 21 DAA ECHCG ECHCO gae / ha gae / ha Note Exp Note Exp 8.75 70 85 60 70 55 4.38 140 40 40 60 30 8.75 140 75 60 80 55
Benzyl Ester of Compound A Salt ofHillTriclopir Visual Weed Control (%) -21 DAA DIGSA gae / ha gae / ha Note Exp 4.38 0 10 - 0 35 0 - 0 70 10 - 0 140 20 - 4.38 35 10 10 4.38 70 30 19 4.38 140 45 28
Benzyl Ester of Compound A Hill SaltTriclopir Visual Weed Control(%) - 21 DAA SCPJU gae / ha gae / ha Note Exp 4.38 0 40 - 0 35 0 - 0 70 50 -
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4.38 35 95 40 4.38 70 95 70
Table 16. Synergistic Activity of Herbicidal Compositions of Compound A Acid and Butotyl Triclopir Ester Applied to Foliage on Weed Control in a Rice Culture System.
Compound AcidTHE Ester ofButotylTriclopir Weed ControlVisual (%) - 23 DAA BRAPP gae / ha gae / ha Note Exp 4.38 0 40 - 8.75 0 55 - 17.5 0 80 - 0 35 0 - 0 70 0 - 4.38 35 50 40 8.75 35 70 55 17.5 35 85 80 4.38 70 65 40 8.75 70 80 55 17.5 70 100 80
AcidCompound A Ester ofButotylTriclopir Visual Weed Control (%) - 23DAA DIGSA ECHCO gae / ha gae / ha Note Exp Note Exp 4.38 0 0 - 15 -
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AcidCompound A Ester ofButotylTriclopir Visual Weed Control (%) - 23DAA DIGSA ECHCO gae / ha gae / ha Note Exp Note Exp 8.75 0 0 - 60 - 17.5 0 10 - 80 - 0 35 0 - 0 - 0 70 0 - 0 - 0 140 0 - 0 - 4.38 35 40 0 40 15 8.75 35 40 0 65 60 17.5 35 40 10 85 80 4.38 70 40 0 40 15 8.75 70 50 0 75 60 17.5 70 45 10 90 80 4.38 140 60 0 45 15 8.75 140 60 0 65 60 17.5 140 50 10 95 80
AcidCompound A Ester ofButotylTriclopir Visual Weed Control (%)- 23 DAA ECHCG gae / ha gae / ha Note Exp 4.38 0 45 - 8.75 0 55 - 0 35 0 - 0 70 0 -
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AcidCompound A Ester ofButotylTriclopir Visual Weed Control (%)- 23 DAA ECHCG gae / ha gae / ha Note Exp 0 140 15 - 4.38 35 45 45 8.75 35 70 55 4.38 70 55 45 8.75 70 65 55 4.38 140 65 53 8.75 140 65 62
Table 17. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Butotyl Triclopir Ester Applied to Foliage on Weed Control in Rice Culture System.
Ester ofBenzila doCompound A Ester ofButotylTriclopir Visual Weed Control (%) -23 DAA DIGSA gae / ha gae / ha Note Exp 4.38 0 0 - 8.75 0 0 - 17.5 0 15 - 0 35 0 - 0 70 0 - 0 140 0 - 4.38 35 40 0 8.75 35 40 0
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Ester ofBenzila doCompound A Ester ofButotylTriclopir Visual Weed Control (%) -23 DAA DIGSA gae / ha gae / ha Note Exp 17.5 35 25 15 4.38 70 25 0 8.75 70 50 0 17.5 70 25 15 4.38 140 20 0 8.75 140 60 0 17.5 140 30 15
Ester ofBenzila doCompound A Ester ofButotylTriclopir Visual Weed Control (%) -23 DAA ECHCG gae / ha gae / ha Note Exp 4.38 0 40 - 8.75 0 55 - 0 35 0 - 0 70 0 - 0 140 15 - 4.38 35 45 40 8.75 35 70 55 4.38 70 40 40 8.75 70 60 55 4.38 140 65 49 8.75 140 65 62
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Ester ofBenzila doCompound A Ester ofButotylTriclopir Visual Weed Control (%) -23 DAA ECHCO gae / ha gae / ha Note Exp 4.38 0 40 - 8.75 0 40 - 17.5 0 75 - 0 70 0 - 0 140 0 - 4.38 70 45 40 8.75 70 80 40 17.5 70 90 75 4.38 140 60 40 8.75 140 70 40 17.5 140 70 75
Table 18. Synergistic Activity of Herbicidal Compositions of Compound A and Methyl Heptyl Ester (MHE) fluroxypir Applied to Foliage on Weed Control in Rice Culture System.
AcidCompound A MHEFluroxipir Visual Weed Control (%) - 21DAA ECHCG ECHCO CIPDI gae / ha gae / ha Note Exp Note Exp Note Exp 4.38 0 15 - 70 - 50 - 8.75 0 50 - 75 - 85 - 0 70 0 - 0 - 15 - 0 140 0 - 0 - 80 -
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4.38 70 70 15 60 70 100 58 8.75 70 95 50 90 75 100 87 4.38 140 90 15 85 70 100 90 8.75 140 95 50 95 75 100 97
AcidCompound A MHEFluroxypyr Visual Weed Control (%) - 19 DAA ECHCG LEFCH gae / ha gae / ha Note Exp Note Exp 19.4 0 80 - 5 - 0 280 25 - 28 - 19.4 280 97 85 75 31
Table 19. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Methyl Heptyl Ester (MHE) fluroxypir Applied to Foliage on Weed Control in a Rice Crop System
Ester ofBenzila doCompound A MHEFluroxypyr Visual Weed Control (%) - 21DAA ECHCG ECHCO gae / ha gae / ha Note Exp Note Exp - 0 10 - 70 - - 0 85 - 75 - - 70 0 - 0 - - 140 0 - 0 - 4.38 70 60 10 85 70 8.75 70 95 85 95 75 4.38 140 85 10 90 70
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Ester ofBenzila doCompound A MHEFluroxypyr Visual Weed Control (%) - 21 DAA ECHCG ECHCO gae / ha gae / ha Note Exp Note Exp 8.75 140 95 85 90 75
Benzyl Ester of Compound A MHEFluroxypyr Visual Weed Control (%)- 19 DAA LEFCH gae / ha gae / ha Note Exp 16 0 58 - 0 280 28 - 16 280 83 69
Table 20. Synergistic Activity of Herbicidal Compositions of Compound A n-Butyl Ester and Methyl heptyl ester (MHE) fluroxypir Applied to Foliage under Weed Control in a Rice Culture System.
Compound A n-Butyl ester MHEFluroxypyr Visual Weed Control (%) -19 DAA ECHCG gae / ha gae / ha Note Exp 16 0 65 - 0 280 25 - 16 280 95 74
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Table 21. Synergistic Activity of Herbicidal Compositions of Compound A Acid and Dimethylammonium Salt (DMA) Dicamba Applied to Foliage on Weed Control Common to Rice Culture Systems.
AcidCompound A DMA saltDicamba Visual Weed Control (%) -20 DAA LEFCH CIPIR gae / ha gae / ha Note Exp Note Exp 5.3 0 10 - 65 - 0 140 0 - 0 - 0 280 0 - 35 - 5.3 140 25 10 90 65 5.3 280 25 10 100 77
Table 22. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Dimethylammonium Salt (DMA) Dicamba Applied to Foliage on Weed Control Common to Rice Culture Systems.
Benzyl Ester of Compound A DMA saltDicamba Visual Weed Control(%) - 20 DAA ECHCO CIPIR gae / ha gae / ha Note Exp Note Exp 4.38 0 50 - 35 - 8.75 0 75 - 35 - 0 70 0 - 0 - 0 140 0 - 0 - 0 280 0 - 35 -
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Benzyl Ester of Compound A DMA saltDicamba Visual Weed Control(%) - 20 DAA ECHCO CIPIR gae / ha gae / ha Note Exp Note Exp 4.38 70 70 50 80 35 8.75 70 75 75 100 35 4.38 140 55 50 65 35 8.75 140 75 75 100 35 4.38 280 70 50 50 58 8.75 280 95 75 95 58
Table 23. Synergistic Activity of Herbicidal Compositions of Compound A and Halauxifene-Methyl Ester Applied to Foliage under Weed Control in a Rice Culture System.
AcidCompound A Halauxifene-Methyl ester Visual Weed Control (%)- 20 DAA LEFCH IPOHE gae / ha gae / ha Note Exp Note Exp 4.38 0 0 - 10 - 8.75 0 0 - 15 - 17.5 0 10 - 30 - 0 2.19 0 - 0 - 0 4.38 10 - 0 - 4.38 2.19 30 0 45 10 8.75 2.19 20 0 50 15
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AcidCompound A Halauxifene-Methyl ester Visual Weed Control (%)- 20 DAA LEFCH IPOHE gae / ha gae / ha Note Exp Note Exp 17.5 2.19 50 10 55 30 4.38 4.38 30 10 30 10 8.75 4.38 35 10 40 15 17.5 4.38 40 19 25 30
Table 24. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Halauxifene-Methyl Ester Applied to Foliage on Weed Control in a Rice Culture System.
Benzyl Ester of Compound A Halauxifene-methyl ester Weed ControlVisual (%) - 20 DAA LEFCH gae / ha gae / ha Note Exp 4.38 0 0 - 8.75 0 20 - 0 2.19 0 - 0 4.38 10 - 4.38 2.19 30 0 8.75 2.19 30 20 4.38 4.38 45 10 8.75 4.38 45 28
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Benzyl Ester of Compound A Halauxifene-methyl ester Weed ControlVisual (%) - 20 DAA CIPIR gae / ha gae / ha Note Exp 4.38 0 15 - 0 2.19 25 - 0 4.38 70 - 4.38 2.19 85 36 4.38 4.38 90 75
Benzyl Ester of Compound A Halauxifene-methyl ester Weed ControlVisual (%) - 20 DAA IPOHE gae / ha gae / ha Note Exp 4.38 0 0 - 8.75 0 10 - 17.5 0 25 - 0 2.19 0 - 0 4.38 04.38 2.19 20 0 8.75 2.19 25 10 17.5 2.19 45 25 4.38 4.38 NT 0 8.75 4.38 30 10 17.5 4.38 35 25
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Table 25. Synergistic Activity of Herbicidal Compositions of Compound A and Quinclorak Applied to Foliage on Weed Control in a Rice Culture System.
AcidCompound A Quincloraque Weed ControlVisual (%) - 21 DAA CIPES gae / ha gai / ha Note Exp 4.38 0 18 - 0 70 0 - 0 140 0 - 0 280 0 - 4.38 70 70 18 4.38 140 20 18 4.38 280 50 18
AcidCompound A Quincloraque Weed ControlVisual (%) - 21 DAA DIGSA gae / ha gaiha Note Exp 21.2 0 10 - 0 560 8 - 21.2 560 40 17
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Table 26. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Quinclorak Applied to Foliage on Weed Control in a Rice Culture System.
Benzyl Ester of Compound A Quincloraque Visual Weed Control(%) - 21 DAA ECHCG CIPIR gae / ha gai / ha Note Exp Note Exp 4.38 0 48 - 75 - 8.75 0 55 - 85 - 0 70 15 - 0 - 0 140 30 - 0 - 0 280 30 - 0 - 4.38 70 50 55 95 75 8.75 70 80 62 100 85 4.38 140 70 63 30 75 8.75 140 80 69 100 85 4.38 280 99 63 95 75 8.75 280 70 69 100 85
Benzyl Ester of Compound A Quincloraque Weed ControlVisual (%) - 20 DAA DIGSA gae / ha gaiha Note Exp 35 0 38 - 0 560 8 -
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Benzyl Ester of Compound A Quincloraque Weed ControlVisual (%) - 20 DAA DIGSA gae / ha gaiha Note Exp 35 560 70 42
Benzyl Ester of Compound A Quincloraque Weed ControlVisual (%) - 21 DAA ISCRU gae / ha gai / ha Note Exp 8 0 20 - 16 0 0 - 0 140 0 - 0 280 0 - 0 560 0 - 8 140 50 20 16 140 100 0 8 280 100 20 16 280 50 0 8 560 20 20 16 560 70 0
BRAPP Brachiaria platifilla (Griseb.) Nash or
Urocloa platifilla (Nash) R.D. Webster brachiaria, broad leaf
CIPDI Ciperus difformis L.
CIPES Ciperus esculentus L.
CIPIR Ciperus would L.
juça, with small tiririca flower, yellow junquinho, rice
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DIGSA
ECHCG
ECHCO
IPOHE
Digitaria sanguinalis (L.) Scop. Echinocloa crusgalli (L.) Beauv.
Echinocloa colona (L.) Link Ipomoea hederacea Jacq.
Large mattress grass
Capybara capim-jaú grass
Morning primrose, ivy leaf
ISCRU Ischaemum rugosum Salisb. saramollagrass
LEFCH Leptocloa chinensis (L.) Nees grass- Chinese
SCPJU Schoenoplectus juncoides (Roxb.) Palla junco, Japanese gae / ha = grams of acid equivalent per hectare gai / ha = grams of active ingredient per hectare Obs = observed value
Exp = expected value as calculated by the Colby equation DAA = days after application
NT = not tested
Example II: Evaluation of Herbicidal Mixtures Applied in Water for Weed Control in Transplanted Rice Fields [00190] Seeds or small weed nuts of the test plant species were planted in muddy soil (mud) prepared by mixing a non-sterilized mineral soil, chopped (mud 50.5, clay
25.5 percent 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 1: 1 volumetric ratio. The prepared sludge was applied in 365 ml aliquots in unperforated (16 oz) (oz.) Plastic pots with a surface area of 86.59 square centimeters (cm ² ) leaving a 3 cm (cm) headspace 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 planting trays. The seedlings in the second or third stage of leaf growth were
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137/202 transplanted to 840 mL of mud contained in unperforated (32 oz.) Plastic pots with a surface area of 86.59 cm ² 4 days before herbicide application. The rice paddy was created by filling the headspace of the pots with 2.5 to 3 cm of water. When necessary to ensure good germination and healthy plants, a treatment with fungicide and / or other chemical agent or physical treatment was applied. The plants were grown for 4-22 days in a greenhouse with a photoperiod of approximately 14 h that was maintained at about 29 ° C during the day and 26 ° C at night. Nutrients were added as Osmocote® (19: 6: 12, N: P: K + nutrients in smaller quantities) to 2 g per pot of (16 oz.) And 4 g per pot of (32 oz.). Water was added on a regular basis to keep the rice paddy flooded and supplemented light 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 stage of true leaf.
[00191] The treatments consisted of the amino acids or esters of 4 amino-3- chloro-5-fluor-6- (4-chloro-2-fluoro-3-methoxy-phenyl) pyridine-2-carboxylic acid (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. [00192] The forms of Compound A (compound of Formula I) tested include:
oh ₃ <t
Compound A Acid
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N
O
Compound A n-Butyl ester
Compound A Benzyl Ester [00193] Other herbicidal components were applied in an acid equivalent base or active ingredient base and included 2,4-D dimethylammonium salt (DMA) formulated as Weedar® 64, Choline salt 2,4 -D formulated as a soluble liquid (SL) (Soluble Liquid), 2,4-D 2-ethyl hexyl ester (EHE) formulated as an SL, MCPA K + / Na + / DMA salt formulated as Agritox 50, ethyl ester hexyl MCPA formulated as MCPA2, methyl heptyl ester fluroxypyr (MHE) formulated as Starane ^® or Starane ^® Ultra, choline salt triclopyr formulated as an SL, trichopyr butothyl ester formulated as an EC, triethylamine salt (TEA) triclopyr as Grandstand ^® R, dimethylammonium salt (DMA) dicamba formulated as Banvel ^® 4S, quincloraque formulated as Facet® 75DF and halauxifene-methyl formulated as a SC.
[00194] Treatment requirements for each compound or herbicidal component were calculated based on the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, an application volume of 2 mL per component per pot and an application area of 86 , 59 cm ² per pot.
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139/202 [00195] For formulated compounds, a measured amount was placed in an individual 100 or 200 mL glass vial and dissolved in a volume of 1.25% (v / v) of AgriDex ^® culture oil concentrate for application solutions. If the tested compound did not readily dissolve, the mixture was heated and / or sonicated.
[00196] For thermal grade compounds, a weighted amount can be placed in a 100 to 200 mL individual glass bottle and dissolved in a volume of acetone to obtain concentrated stock solutions. If the test compound does not readily dissolve, the mixture can be heated and / or sonicated. The concentrated stock solutions obtained can be diluted with an equivalent volume of an aqueous mixture containing 2.5% (v / v) of culture oil concentrate so that the final application solutions contain 1.25% (v / v) ) of culture oil concentrate.
[00197] The applications were made by injecting with a pipette appropriate amounts of the application solutions, individually and sequentially, into the aqueous layer of the rice field. The control plants were treated in the same way with the solvent without activity. The applications were made in such a way that the treated plant material received the same concentrations of acetone and culture oil concentrate.
[00198] The treated plants and the control plants were placed in a greenhouse as described above and water was added as needed to maintain a flooded rice field. After approximately 3 weeks the condition of the test plants compared to that of the untreated plants was determined visually and rated on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete death.
[00199] Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, S.R., 1967. Calculation of
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140/202 the synergistic and antagonistic response of herbicide combinations. Weeds 15: 20-22).
[00200] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B / 100)
A = observed effectiveness of active ingredient A at the same concentration as used in the mixture.
B = observed effectiveness of active ingredient B at the same concentrations as used in the mixture.
[00201] Some of the tested compounds, application rates employed, plant species tested and results are given in Tables 27-53.
Table 27. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A and Dimethylammonium Salt (DMA) 2,4D on Weed Control in a Rice Culture System.
AcidCompound A DMA salt2,4-D Visual Weed Control (%) -21 DAA ECHCG LEFCH gae / ha gae / ha Note Exp Note Exp 8.75 0 0 - 0 - 17.5 0 0 - 0 - 35 0 20 - 30 - 0 140 0 - 0 - 0 280 0 - 60 - 8.75 140 25 0 30 0 17.5 140 20 0 10 0 35 140 50 20 90 30
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AcidCompound A DMA salt2,4-D Visual Weed Control (%) -21 DAA ECHCG LEFCH gae / ha gae / ha Note Exp Note Exp 8.75 280 40 0 95 60 17.5 280 65 0 55 60 35 280 80 20 90 72
AcidCompound A DMA salt2,4-D Visual Weed Control (%) -21 DAA ECHOR CIPRO gae / ha gae / ha Note Exp Note Exp 8.75 0 10 - 0 - 17.5 0 15 - 30 - 35 0 20 - 85 - 0 280 15 - 0 - 8.75 280 40 24 30 0 17.5 280 40 28 85 30 35 280 40 32 95 85
AcidCompound A DMA salt 2,4-D Visual Weed Control(%) - 21 DAA SCPJU gae / ha gae / ha Note Exp 8.75 0 15 -
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AcidCompound A DMA salt 2,4-D Visual Weed Control(%) - 21 DAA SCPJU gae / ha gae / ha Note Exp 17.5 0 80 - 0 140 0 - 0 280 0 - 8.75 140 100 15 17.5 140 95 80 8.75 280 80 15 17.5 280 90 80
Table 28. Synergistic Activity of Compound A Benzyl Ester Water and Dimethylammonium Salt (DMA) 2,4-D Applications on Weed Control in a Rice Culture System.
Ester ofBenzila doCompound A DMA salt2,4-D Visual Weed Control (%) -21 DAA ECHCG LEFCH gae / ha gae / ha Note Exp Note Exp 4.38 0 0 - 0 - 8.75 0 0 - 0 - 17.5 0 25 - 0 - 0 140 0 - 0 - 0 280 0 - 60 -
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4.38 140 40 0 30 0 8.75 140 35 0 30 0 17.5 140 75 25 55 0 4.38 280 20 0 80 60 8.75 280 20 0 65 60 17.5 280 70 25 85 60
Benzyl Ester of Compound A 2,4-D DMA salt Weed Control Visual (%) - 21 DAA CIPRO gae / ha gae / ha Note Exp 4.38 0 0 - 8.75 0 0 - 0 280 0 - 4.38 280 70 0 8.75 280 90 0
Table 29. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A and Choline Salt 2,4-D on Weed Control in Rice Culture System.
AcidCompound A Choline salt 2,4-D Weed ControlVisual (%) - 20 DAA ECHOR gae / ha gae / ha Note Exp 8.75 0 10 - 17.5 0 25 -
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AcidCompound A Choline salt 2,4-D Weed ControlVisual (%) - 20 DAA ECHOR gae / ha gae / ha Note Exp 35 0 25 - 0 240 0 - 0 480 20 - 8.75 240 35 10 17.5 240 45 25 35 240 95 25 8.75 480 55 28 17.5 480 50 40 35 480 65 40
AcidCompound A Choline salt 2,4-D Weed ControlVisual (%) - 20 DAA CIPRO gae / ha gae / ha Note Exp 8.75 0 0 - 17.5 0 70 - 0 240 30 - 0 480 30 - 8.75 240 95 30 17.5 240 90 79 8.75 480 100 30 17.5 480 100 79
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AcidCompound A Choline salt 2,4-D Weed ControlVisual (%) - 20 DAA SCPMA gae / ha gae / ha Note Exp 8.75 0 0 - 17.5 0 0 - 35 0 0 - 0 240 0 - 8.75 240 100 0 17.5 240 100 0 35 240 100 0
Table 30. Synergistic Activity of Water Applications of Herbicidal Compositions of Benzyl Ester of Compound A and Choline Salt 2,4-D on Weed Control in Rice Culture System.
Benzyl Ester of Compound A Choline salt 2,4-D Weed ControlVisual (%) - 20 DAA ECHOR gae / ha gae / ha Note Exp 4.38 0 10 - 8.75 0 20 - 17.5 0 50 - 0 240 0 - 0 480 20 - 4.38 240 40 10
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Benzyl Ester of Compound A Choline salt 2,4-D Weed ControlVisual (%) - 20 DAA ECHOR gae / ha gae / ha Note Exp 8.75 240 50 20 17.5 240 100 50 4.38 480 40 28 8.75 480 70 36 17.5 480 90 60
Table 31. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A and Ethyl Hexyl Ester (EHE) 2,4-D on Weed Control in a Rice Culture System.
AcidCompoundTHE 2,4-DEHE Visual Weed Control (%) - 22 DAA ECHCG ECHOR CIPRO gae / ha gae / ha Note Exp Note Exp Note Exp 8.75 0 0 - 0 - 0 - 17.5 0 20 - 0 - 20 - 35 0 25 - 20 - 50 - 0 140 0 - 0 - 0 - 0 280 0 - 0 - 0 - 8.75 140 15 0 10 0 80 0 17.5 140 20 20 20 0 100 20 35 140 45 25 25 20 100 50
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AcidCompoundTHE 2,4-DEHE Visual Weed Control (%) - 22 DAA ECHCG ECHOR CIPRO gae / ha gae / ha Note Exp Note Exp Note Exp 8.75 280 35 0 20 0 100 0 17.5 280 60 20 25 0 100 20 35 280 75 25 65 20 95 50
Table 32. Synergistic Activity of Compound A Benzyl Ester Water and Ethyl Hexyl Ester (EHE) 2,4-D Applications on Weed Control in Rice Culture System.
Benzyl Ester of Compound A 2,4-D EHE Weed ControlVisual (%) - 22 DAA ECHOR gae / ha gae / ha Note Exp 8.75 0 25 - 17.5 0 45 - 0 140 0 - 0 280 0 - 8.75 140 55 25 17.5 140 50 45 8.75 280 75 25 17.5 280 85 45
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Ester ofBenzila doCompound A 2,4-D EHE Visual Weed Control (%) -22 DAA ECHCG CIPRO gae / ha gae / ha Note Exp Note Exp 4.38 0 30 - 90 - 8.75 0 45 - 70 - 0 140 0 - 0 - 0 280 0 - 0 - 4.38 140 15 30 100 90 8.75 140 60 45 100 70 4.38 280 45 30 100 90 8.75 280 45 45 100 70
Table 33. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A and MCPA (K + / Na + / DMA Salt) on Weed Control in Rice Culture System.
AcidCompound A MCPA salt Weed ControlVisual (%) - 25 DAA ECHOR gae / ha gai / ha Note Exp 8.75 0 0 - 17.5 0 0 - 35 0 40 - 0 140 0 - 8.75 140 10 0
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AcidCompound A MCPA salt Weed ControlVisual (%) - 25 DAA ECHOR gae / ha gai / ha Note Exp 17.5 140 20 0 35 140 60 40
AcidCompound A MCPA salt Visual Weed Control (%) - 25 DAA LEFCH gae / ha gai / ha Note Exp 8.75 0 50 - 17.5 0 50 - 35 0 85 - 0 70 0 - 0 140 0 - 8.75 70 50 50 17.5 70 30 50 35 70 100 85 8.75 140 100 50 17.5 140 100 50 35 140 100 85
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AcidCompound A MCPA salt Visual Weed Control (%) - 25 DAA SCPJU gae / ha gai / ha Note Exp 8.75 0 65 - 17.5 0 80 - 35 0 95 - 0 70 0 - 8.75 70 85 65 17.5 70 90 80 35 70 100 95
Table 34. Synergistic Activity of Water Applications of Herbicidal Compositions of Benzyl Ester of Compound A and MCPA (K + / Na + / DMA Salt) on Weed Control in a Rice Culture System.
Benzyl Ester of Compound A MCPA Salt Weed ControlVisual (%) - 25 DAA LEFCH gae / ha gai / ha Note Exp 8.75 0 50 - 17.5 0 90 - 0 70 0 - 0 140 0 - 8.75 70 100 50 17.5 70 100 90
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Benzyl Ester of Compound A Salt MCPA Weed ControlVisual (%) - 25 DAA LEFCH gae / ha gai / ha Note Exp 8.75 140 100 50 17.5 140 100 90
Table 35. Synergistic Activity of Water Applications of Compound A Acid Herbicidal Compositions and Ethyl Hexyl Ester (EHE) from MCPA on Weed Control in a Rice Culture System.
AcidCompound A MCPA EHE Visual Weed Control (%) -19 DAA ECHOR LEFCH gae / ha gai / ha Note Exp Note Exp 42.4 0 15 - 10 - 0 280 30 - 0 - 42.4 280 97 40 70 10
Table 36. Synergistic Activity of Water Applications of Compound A Benzyl Ester Herbicidal Compositions and MCPA Ethyl Hexyl Ester (EHE) on Weed Control in a Rice Culture System.
Benzyl Ester of Compound A MCPA EHE Weed ControlVisual (%) - 19 DAA LEFCH gae / ha gai / ha Note Exp 35 0 80 -
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Benzyl Ester of Compound A MCPA EHE Weed ControlVisual (%) - 19 DAA LEFCH gae / ha gai / ha Note Exp 0 280 0 - 35 280 97 80
Table 37. Synergistic Activity of Water Applications of Compound A n-Butyl Ester Herbicidal Composites and MCPA Ethyl Hexyl Ester (EHE) on Weed Control in a Rice Culture System.
Compound A n-Butyl ester EHE MCPA Weed ControlVisual (%) - 19 DAA LEFCH gae / ha gai / ha Note Exp 35 0 43 - 0 280 0 - 35 280 85 43
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Table 38. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A and Triethylamine Salt (TEA) triclopyr On Weed Control in a Rice Culture System.
AcidCompound A TEA Triclopir salt Visual Weed Control (%) -25 DAA ECHCG SCPJU gae / ha gae / ha Note Exp Note Exp 8.75 0 0 - 65 - 17.5 0 0 - 80 - 0 70 0 - 20 - 0 140 0 - 30 - 8.75 70 40 0 90 72 17.5 70 15 0 95 84 8.75 140 30 0 95 76 17.5 140 40 0 95 86
AcidCompound A TEA Triclopir salt Visual Weed Control (%) -25 DAA ECHOR LEFCH gae / ha gae / ha Note Exp Note Exp 8.75 0 0 - 50 - 17.5 0 0 - 50 - 35 0 40 - 85 - 0 70 0 - 0 - 0 140 0 - 0 -
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AcidCompound A TEA Triclopir salt Visual Weed Control (%) -25 DAA ECHOR LEFCH gae / ha gae / ha Note Exp Note Exp 8.75 70 0 0 40 50 17.5 70 20 0 100 50 35 70 75 40 100 85 8.75 140 20 0 100 50 17.5 140 75 0 100 50 35 140 65 40 100 85
AcidCompound A TEA Triclopir salt Weed ControlVisual (%) - 19 DAA ECHOR gae / ha gae / ha Note Exp 42.4 0 15 - 0 280 35 - 42.4 280 97 45
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Table 39. Synergistic Activity of Water Applications of Compound A Benzyl Ester Herbicidal Compositions and Triethylamine Salt (TEA) triclopyr On Weed Control in a Rice Culture System.
Ester ofBenzila doCompound A TEA Triclopir salt Visual Weed Control (%) -25 DAA ECHOR LEFCH gae / ha gae / ha Note Exp Note Exp 8.75 0 85 - 50 - 17.5 0 90 - 90 - 0 70 0 - 0 - 0 140 0 - 0 - 8.75 70 99 85 100 50 17.5 70 100 90 100 90 8.75 140 99 85 100 50 17.5 140 100 90 100 90
Table 40. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A and Choline Salt Triclopir on Weed Control in a Rice Culture System.
Compound AcidTHE Hill SaltTriclopir Weed ControlVisual (%) - 22 DAA ECHCG gae / ha gae / ha Note Exp 21.2 0 25 -
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Compound AcidTHE Hill SaltTriclopir Weed ControlVisual (%) - 22 DAA ECHCG gae / ha gae / ha Note Exp 42.4 0 30 - 0 140 2021.2 140 55 40 42.4 140 95 44
Compound AcidTHE Hill SaltTriclopir Weed ControlVisual (%) - 22 DAA LEFCH gae / ha gae / ha Note Exp 10.6 0 20 - 21.2 0 40 - 42.4 0 60 - 0 70 0 - 0 140 0 - 10.6 70 100 20 21.2 70 70 40 42.4 70 100 60 10.6 140 100 20 21.2 140 100 40 42.4 140 100 60
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Compound AcidTHE Hill SaltTriclopir Weed ControlVisual (%) - 22 DAA CIPRO gae / ha gae / ha Note Exp 10.6 0 0 - 21.2 0 40 - 0 70 0 - 0 140 0 - 10.6 70 0 0 21.2 70 90 40 10.6 140 30 0 21.2 140 100 40
AcidCompound A Hill SaltTriclopir Visual Weed Control (%) -22 DAA FIMMI SCPJU gae / ha gae / ha Note Exp Note Exp 10.6 0 40 - 60 - 0 70 15 - 15 - 0 140 80 - 50 - 10.6 70 100 49 90 66 10.6 140 100 88 99 80
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Table 41. Synergistic Activity of Water Applications of Compound A Benzyl Ester Herbicidal Compositions and Triclopir Choline Salt on Weed Control in a Rice Culture System.
Benzyl ester ofCompound A Hill SaltTriclopir Weed ControlVisual (%) - 22 DAA ECHCG gae / ha gae / ha Note Exp 4.38 0 30 - 8.75 0 45 - 17.5 0 90 - 0 70 15 - 0 140 20 - 4.38 70 70 41 8.75 70 80 53 17.5 70 99 92 4.38 140 80 44 8.75 140 30 56 17.5 140 95 92
Benzyl ester ofCompound A Hill SaltTriclopir Weed ControlVisual (%) - 22 DAA ECHOR gae / ha gae / ha Note Exp 8.75 0 35 - 17.5 0 30 - 0 70 10 - 0 140 15 -
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Benzyl ester ofCompound A Hill SaltTriclopir Weed ControlVisual (%) - 22 DAA ECHOR gae / ha gae / ha Note Exp 8.75 70 90 42 17.5 70 95 37 8.75 140 85 45 17.5 140 85 41
Table 42. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A and Butotyl Triclopir Ester on Weed Control in a Rice Culture System.
AcidCompound A Ester ofButotylTriclopir Visual Weed Control (%) -22 DAA ECHCG ECHOR gae / ha gae / ha Note Exp Note Exp 8.75 0 0 - 0 - 17.5 0 20 - 0 - 35 0 25 - 20 - 0 70 0 - 0 - 0 140 0 - 0 - 8.75 70 20 0 20 0 17.5 70 30 20 40 0 35 70 50 25 20 20 8.75 140 30 0 20 0 17.5 140 25 20 40 0
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AcidCompound A Ester ofButotylTriclopir Visual Weed Control (%) -22 DAA ECHCG ECHOR gae / ha gae / ha Note Exp Note Exp 35 140 40 25 40 20
AcidCompound A Butotyl esterTriclopir Visual Weed Control(%) - 22 DAA CIPRO SCPMA gae / ha gae / ha Note Exp Note Exp 8.75 0 0 - 0 - 17.5 0 20 - 0 - 35 0 50 - 0 - 0 70 0 - 50 - 0 140 40 - 60 - 8.75 70 30 0 20 50 17.5 70 100 20 60 50 35 70 100 50 100 50 8.75 140 50 40 100 60 17.5 140 100 52 100 60 35 140 95 70 100 60
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Table 43. Synergistic Activity of Water Applications of Compound A Benzyl Ester Herbicidal Compositions and Triclopyr Butotyl Ester on Weed Control in a Rice Culture System.
Benzyl Ester of Compound A Butotyl esterTriclopir Weed ControlVisual (%) - 22 DAA SCPMA gae / ha gae / ha Note Exp 4.38 0 0 - 8.75 0 0 - 17.5 0 0 - 0 70 50 - 0 140 60 - 4.38 70 100 50 8.75 70 100 50 17.5 70 90 50 4.38 140 100 60 8.75 140 100 60 17.5 140 100 60
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Table 44. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A and Methyl Heptyla Ester (MHE) fluroxypir on Weed Control in a Rice Culture System.
Compound A Acid MHE Fluroxipir Visual Weed Control (%) - 25 DAA ECHCG gae / ha gae / ha Note Exp 8.75 0 0 - 17.5 0 0 - 35 0 70 - 0 140 0 - 8.75 140 40 0 17.5 140 50 0 35 140 90 70
Compound A Acid MHE Fluroxipir Visual Weed Control (%) - 25 DAA LEFCH gae / ha gae / ha Note Exp 8.75 0 50 - 17.5 0 50 - 35 0 85 - 0 70 20 - 8.75 70 100 60 17.5 70 100 60 35 70 100 88
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Compound A Acid MHE Fluroxipir Visual Weed Control (%) -25 DAA ECHOR SCPJU gae / ha gae / ha Note Exp Note Exp 8.75 0 0 - 65 - 17.5 0 0 - 80 - 35 0 40 - 95 - 0 70 0 - 20 - 0 140 0 - 30 - 8.75 70 50 0 90 65 17.5 70 50 0 90 80 35 70 100 40 99 95 8.75 140 15 0 95 76 17.5 140 70 0 95 86 35 140 95 40 100 97
Compound A Acid MHE Fluroxipir Visual Weed Control (%) - 22 DAA SCP BAD gae / ha gae / ha Note Exp 16 0 0 - 32 0 0 - 64 0 30 - 0 149 30 - 16 149 100 30 32 149 100 30 64 149 100 51
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AcidCompound A MHE Fluroxipir Weed ControlVisual (%) - 19 DAA ECHOR gae / ha gae / ha Note Exp 42.4 0 15 - 0 280 15 - 42.4 280 98 28
Table 45. Synergistic Activity of Water Applications of Compound A Benzyl Ester Herbicidal Compositions and Methyl Hepatyl Fluroxypyr (MHE) Ester on Weed Control in a Rice Culture System.
Benzyl Ester of Compound A MHE Fluroxipir Weed ControlVisual (%) - 25 DAA ECHOR gae / ha gae / ha Note Exp 8.75 0 85 - 0 70 0 - 0 140 0 - 8.75 70 99 85 8.75 140 99 85
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Benzyl Ester of Compound A MHE Fluroxipir Visual injury (%) - 25DAA LEFCH gae / ha gae / ha Note Exp 8.75 0 50 - 17.5 0 90 - 0 70 20 - 8.75 70 100 60 17.5 70 100 92
Benzyl Ester of Compound A MHE Fluroxipir Weed ControlVisual (%) - 19 DAA ECHCG gae / ha gae / ha Note Exp 8 0 35 - 16 0 85 - 0 70 0 - 0 140 0 - 0 280 0 - 8 70 60 35 16 70 90 85 8 140 65 35 16 140 95 85 8 280 80 35 16 280 100 85
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Benzyl Ester of Compound A MHE Fluroxipir Weed ControlVisual (%) - 19 DAA ECHOR gae / ha gae / ha Note Exp 8 0 10 - 16 0 25 - 32 0 35 - 0 70 0 - 0 140 0 - 0 280 0 - 8 70 20 10 16 70 40 25 32 70 75 35 8 140 25 10 16 140 75 25 32 140 70 35 8 280 50 10 16 280 70 25 32 280 60 35
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Table 46. Synergistic Activity of Water Applications of Compound A n-Butyl Ester Herbicidal Compositions and Methyl heptyl ester (MHE) fluroxypir on Weed Control in a Rice Culture System.
Compound A n-Butyl ester MHE Fluroxipir Weed ControlVisual (%) - 19 DAA ECHOR gae / ha gae / ha Note Exp 35 0 80 - 0 280 15 - 35 280 100 83
Table 47. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound a and Dicamba Dimethylammonium Salt (DMA) [00202] On Weed Control Common to Rice Culture Systems.
Acid DMA salt Weed Control Compound A Dicamba Visual (%) - 21 DAA ECHCG gae / ha gae / ha Note Exp 10.6 0 0 - 0 140 0 - 0 280 10 - 10.6 140 25 0 10.6 280 30 10
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AcidCompound A DMA saltDicamba Visual Weed Control (%) -21 DAA ECHOR SCPMA gae / ha gae / ha Note Exp Note Exp 42.415 - 0 - 0 140 10 - 0 - 0 280 15 - 0 - 42.4 140 35 24 60 0 42.4 280 50 28 100 0
Table 48. Synergistic Activity of Water Applications of Herbicidal Compositions of Benzyl Ester of Compound A and Dimethylammonium Salt (DMA) Dicamba on Weed Control Common to Rice Culture Systems.
Benzyl ester ofCompound A DMA saltDicamba Weed ControlVisual (%) - 21 DAA ECHOR gae / ha gai / ha Note Exp 4.38 0 15 - 8.75 0 15 - 17.5 0 20 - 0 140 10 - 0 280 15 - 4.38 140 30 24 8.75 140 30 24 17.5 140 40 28
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Benzyl ester ofCompound A DMA saltDicamba Weed Control Visual (%) - 21 DAA ECHOR gae / ha gai / ha Note Exp 4.38 280 40 28 8.75 280 45 28 17.5 280 50 32
Benzyl ester ofCompound A DMA saltDicamba Weed ControlVisual (%) - 21 DAA SCPMA gae / ha gai / ha Note Exp 4.38 0 0 - 8.75 0 0 - 17.5 0 0 - 0 140 0 - 4.38 140 95 0 8.75 140 70 0 17.5 140 100 0
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Table 49. Synergistic Activity of Water Applications of Compound A Acid Herbicidal Compositions and Halauxifene-Methyl Ester on Weed Control in a Rice Culture System.
AcidCompound A Halauxifene-methyl ester Weed ControlVisual (%) - 20 DAA ECHCG gae / ha gae / ha Note Exp 10.6 0 20 - 21.2 0 20 - 42.4 0 50 - 0 4.38 50 - 0 8.75 60 - 10.6 4.38 80 60 21.2 4.38 90 60 42.4 4.38 100 75 10.6 8.75 100 68 21.2 8.75 95 68 42.4 8.75 99 80
AcidCompound A Halauxifene-methyl ester Visual Weed Control (%) - 20 DAA ECHOR gae / ha gae / ha Note Exp 21.2 0 30 - 42.4 0 45 -
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AcidCompound A Halauxifene-methyl ester Visual Weed Control (%) - 20 DAA ECHOR gae / ha gae / ha Note Exp 0 4.38 25 - 0 8.75 35 - 21.2 4.38 95 48 42.4 4.38 40 59 21.2 8.75 95 55 42.4 8.75 95 64
AcidCompound A Halauxifene-methyl ester Visual Weed Control (%) - 20 DAA CIPRO gae / ha gae / ha Note Exp 10.6 0 10 - 21.2 0 20 - 0 4.38 70 - 0 8.75 50 - 10.6 4.38 20 73 21.2 4.38 100 76 10.6 8.75 100 55 21.2 8.75 100 60
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Table 50. Synergistic Activity of Water Applications of Compound A Benzyl Ester Herbicidal Compositions and Methyl Halauxifene-Ester on Weed Control in a Rice Culture System.
Ester ofBenzila doCompound A Halauxifene-Methyl ester Visual Weed Control (%)- 20 DAA ECHCG ECHOR gae / ha gae / ha Note Exp Note Exp 4.38 0 15 - 25 - 8.75 0 20 - 20 - 17.5 0 40 - 30 - 0 4.38 50 - 25 - 0 8.75 60 - 35 - 4.38 4.38 99 58 85 44 8.75 4.38 95 60 85 40 17.5 4.38 80 70 99 48 4.38 8.75 95 66 50 51 8.75 8.75 90 68 90 48 17.5 8.75 99 76 100 55
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Benzyl Ester of Compound A Halauxifene-methyl ester Visual Weed Control (%) - 20 DAA CIPRO gae / ha gae / ha Note Exp 4.38 0 50 - 8.75 0 0 - 0 4.38 70 - 0 8.75 50 - 4.38 4.38 70 85 8.75 4.38 100 70 4.38 8.75 95 75 8.75 8.75 90 50
Table 51. Synergistic Activity of Water Applications of Herbicidal Compositions of Compound A and Quinclorak on Weed Control in a Rice Culture System.
AcidCompound A Quincloraque Visual Weed Control (%) - 21 DAA ECHOR CIPIR gae / ha gai / ha Note Exp Note Exp 8.75 0 0 - 0 - 17.5 0 0 - 0 - 35 0 20 - 95 - 0 560 0 - 0 - 8.75 560 20 0 50 0
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AcidCompound A Quincloraque Visual Weed Control (%) - 21 DAA ECHOR CIPIR gae / ha gai / ha Note Exp Note Exp 17.5 560 30 0 85 0 35 560 30 20 95 95
AcidCompound A Quincloraque Visual Weed Control (%)- 20 DAA ECHOR SCPMA gae / ha gai / ha Note Exp Note Exp 42.4 0 18 - 0 - 84.8 0 33 - 0 - 0 560 20 - 0 - 42.4 560 50 34 0 0 84.8 560 68 46 100 0
Table 52. Synergistic Activity of Water Applications of Compound A and Quinclorak N-Butyl Ester Herbicidal Compositions on Weed Control in a Rice Culture System.
Compound A n-Butyl ester Quincloraque Weed ControlVisual (%) - 20 DAA SCPMA gae / ha gai / ha Note Exp 35 0 0 - 70 0 0 -
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Compound A n-Butyl ester Quincloraque Weed ControlVisual (%) - 20 DAA SCPMA gae / ha gai / ha Note Exp 0 560 0 - 35 560 65 0 70 560 100 0
Table 53. Synergistic Activity of Water Applications of Herbicidal Compositions of Benzyl Ester of Compound A and Quinclorak on Weed Control in a Rice Culture System.
Benzyl Ester of Compound A Quincloraque Weed ControlVisual (%) - 20 DAA ECHOR gae / ha gai / ha Note Exp 35 0 73 - 0 560 20 - 35 560 97 78
Benzyl Ester of Compound A Quincloraque Weed ControlVisual (%) - 20 DAA SCPMA gae / ha gai / ha Note Exp 35 0 0 - 70 0 0 - 0 560 0 -
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35 560 100 0 70 560 100 0
CIPIR Ciperus would L. Junquinho rice CIPRO Ciperus rotundus L. purple, purple ECHCG Echinocloa crusgalli (L.) Beauv. Capybara grass ECHOR Echinocloa orizoides (Ard.) Fritsch cornfield, initial FIMMI Fimbristilis miliacea (L.) Vahl cuminho LEFCH Leptocloa chinensis (L.) Nees Chinese grass SCPJU Schoenoplectus juncoides (Roxb.) Palla junco, Japanese SCPMA Schoenoplectus maritimus (L.) Lie clubrush, sea
gae / ha = grams of acid equivalent per hectare gai / ha = grams of active ingredient per hectare Obs = observed value
Exp = expected value as calculated using the Colby equation DAA = days after application
NT = not tested
Example III. Evaluation of Herbicidal Mixtures Applied to Post-emergence Foliage for Weed Control Common to Row Cultures such as Corn and Soybeans [00203] Seeds or small nuts of test plant species were planted in a soil matrix prepared by mixing a clay or sandy clay (for example, mud 28.6 percent, clay 18.8 percent and 52.6 percent sand, with a pH of about 5.8 and an organic matter content of about 1.8 percent) and powder of limestone in an 80 to 20 ratio. The soil matrix was contained in plastic pots with a surface area of 84.6 square centimeters (cm ² ) and a volume of 560 cubic centimeters (cm ³ ). When necessary to ensure good germination and healthy plants, a fungicidal treatment and / or other chemical or physical treatment was
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177/202 applied. The plants were grown for 7-31 days (d) in a greenhouse with a photoperiod of approximately 15 hours (h) that was maintained at about 23-29 ° C during the day and 22-28 ° C at night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg) and water were added on a regular basis and supplemental light was provided with 1000 Watt metal halide lamps suspended as needed. The plants were used for testing when they reached the first, second or third stage of true leaf.
[00204] Treatment needs were calculated based on the rates being tested, the concentration of active ingredient or acid equivalent in the formulation and an application volume of 12 mL at a rate of 187 L / ha.
[00205] The treatments consist of the acid or esters of 4 amino-3- chloro-5- fluoro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) pyridine-2-carboxylic acid (Compound A), each formulated as a SC, and various herbicidal components alone and in combination. Compound A forms were applied on an acid equivalent basis.
[00206] Forms of Compound A (compound of Formula I) tested include:
Compound A Acid
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Compound A Benzyl Ester [00207] Other herbicidal components were applied on an acid equivalent base and included synthetic auxin herbicides 2,4-D dimethylamine salt formulated as Weedar® 64 and K + Halauxifene salt formulated as a soluble liquid (SL). For treatments comprised of formulated compounds, measured amounts of compounds were individually placed in 25 mL glass flasks and diluted in a volume of 1.5% (v / v) concentration of Agri-Dex ^® culture oil to obtain solutions of stock 6X. If the tested compound did not readily dissolve, the mixture was heated and / or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (typically 2 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of an equivalent 1.5% (v / v) mixture of culture oil concentrate and water so that the final spray solutions contained 1.25 +/- 0.05% (v / v) of culture oil concentrate.
[00208] 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 6X stock solutions. If a test compound does not readily dissolve, the mixture can be heated and / or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (for example,
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179/202 example, 2 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (v / v) concentration of culture oil and water so that the solutions of Final sprays contain 1.25% (v / v) of culture oil concentration. 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. [00209] 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 6X stock solutions and measured amounts of formulated compounds can be placed individually in 25 ml glass vials and diluted in a volume of 1.5% (v / v) concentration of culture oil or water to obtain 6X stock solutions. If a test compound does not readily dissolve, the mixture was heated and / or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (for example, 2 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of a 1.5% aqueous mixture (v / v) culture oil concentrate and water so that the final spray solutions contain 1.25% (v / v) culture oil concentrate. When necessary, additional water and / or 97: 3 v / v acetone / DMSO can be added to individual application solutions so that the final concentrations of acetone and DMSO of the application solutions being compared are 16.2% and 0, 5%, respectively.
[00210] All stock solutions and application solutions have been visually inspected for compatibility
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180/202 compound before application. The compost requirements are based on an application volume of 12 mL at a rate of 187 liters per hectare (L / ha). The formulated compounds were applied to the plant material with a suspended Mandel strip sprayer equipped with 8002E nozzles calibrated to apply 187 L / ha over an application area of 0.503 square meters (m ² ) at a spray height of 46 to 50 cm (18 to 20 inches) above the canopy height of the average plant. Control plants were sprayed in the same way with the solvent without activity.
[00211] The treated plants and the control plants were placed in a greenhouse as described above and irrigated by sub-irrigation to prevent run-off of the test compounds. After approximately 2 weeks, the condition of the test plants compared to that of the untreated plants was determined visually and rated on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete death.
[00212] 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).
[00213] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected: A + B - (A x B / 100)
A = observed effectiveness of active ingredient A at the same concentration as used in the mixture.
B = observed effectiveness of active ingredient B at the same concentration as used in the mixture.
[00214] Some of the tested compounds, application rates employed, tested plant species and results are given in the
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Tables 54-56.
Table 54. Synergistic Activity of Herbicidal Compositions of Compound A Acid and DMA 2,4-D Salt Applied to Foliage on Weed Control Common to Row, Corn and Soy Crops.
AcidCompound A 2,4-D DMA salt Weed ControlVisual (%) - 16 DAA PANDI gae / ha gae / ha Note Exp 3.75 0 60 - 0 105 0 - 0 210 0 - 3.75 105 75 60 3.75 210 80 60
Table 55. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and DMA 2,4-D Salt on Control of Common Weeds to Corn and Soybeans.
Benzyl Ester of Compound A 2,4-D DMA salt Weed ControlVisual (%) - 14 DAA ELEIN gae / ha gae / ha Note Exp 3.75 0 0 - 0 52.5 0 - 0 105 0 - 3.75 52.5 15 0 3.75 105 15 0
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Benzyl Ester of Compound A 2,4-D DMA salt Weed ControlVisual (%) - 16 DAA PANMI gae / ha gae / ha Note Exp 3.75 0 15 - 7.5 0 50 - 15 0 75 - 0 52.5 0 - 0 105 10 - 3.75 52.5 50 15 7.5 52.5 45 50 15 52.5 90 75 3.75 105 60 24 7.5 105 75 55 15 105 75 78
Table 56. Synergistic Activity of Compound A Benzyl Ester Herbicidal Compositions and K + Haulaxifene Salt Applied to Foliage under Common Weed Control in Corn and Soy.
Benzyl Ester of Compound A K + saltHalauxifene Weed ControlVisual (%) - 17 DAA ELEIN gae / ha gae / ha Note Exp 7.5 0 20 - 0 3.75 30 -
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Benzyl Ester of Compound A K + saltHalauxifene Weed ControlVisual (%) - 17 DAA ELEIN gae / ha gae / ha Note Exp 0 7.5 40 - 0 15 50 - 7.5 3.75 45 44 7.5 7.5 60 52 7.5 15 75 60
Benzyl Ester of Compound A K + saltHalauxifene Weed ControlVisual (%) - 13 DAA SORHA gae / ha gae / ha Note Exp 3.75 0 0 - 7.5 0 0 - 15 0 10 - 0 7.5 0 - 3.75 7.5 20 0 7.5 7.5 15 0 15 7.5 10 10
ELEIN Eleusine indica (L.) Gaertn. Goose grass (goosegrass)
PANDI Panicum dichotomiflorum Michx. panicum, fall
PANMI Panicum miliaceum L. millet, prose-wild (millet, wild-prose)
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SORHA Sorghum halepense (L.) Pers. Johnson gram (johnsongrass) gae / ha = grams of acid equivalent per hectare gai / ha = grams of active ingredient per hectare Obs = observed value
Exp = expected value as calculated using the Colby equation DAA = days after application
Example IV. Evaluation of Herbicidal Mixtures Applied to Post-emergence Foliage for Weed Control in Cereal Cultures in the Greenhouse.
[00215] 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 pots plastics with a surface area of 103.2 square centimeters (cm ² ). When necessary to ensure good germination and healthy plants, a fungicidal treatment and / or other chemical or physical treatment was applied. The plants were grown for 7-36 days in a greenhouse with a photoperiod of approximately 14 hours that was maintained at about 18 ° C during the day and 17 ° C at night. Nutrients and water were added on a regular basis and supplemental light was provided with 1000 Watt metal halide lamps suspended as needed. The plants were used for testing when they reached the second or third stage of true leaf.
[00216] The treatments consisted of benzyl ester of 4-amino-3-chloro-5-fluorine-6- (4-chloro-2-fluor-3-methoxy-phenyl) pyridine-2-carboxylic acid (Compound A), formulated as a SC and a second cereal herbicide alone and in combination.
[00217] The forms of compound A (compound of Formula I) tested include:
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Compound A Benzyl Ester [00218] Measured aliquots of 4-amino-3-chloro-5-fluor-6- (4-chloro-2-fluor-3-methoxy-phenyl) pyridine-2-carboxylic acid benzyl ester ( Compound A) were placed in 25 milliliter (mL) glass bottles and diluted in a 1.25% (v / v) volume of concentrated Agri-Dex® culture oil to obtain stock solutions. The compost needs are based on an application volume of 12 mL at a rate of 187 liters per hectare (L / ha). Spray solutions of the second cereal herbicide and mixtures of experimental compound 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 combinations of two and three modes. The formulated compounds were applied to the plant material with a suspended Mandel strip sprayer equipped with 8002E nozzles calibrated to apply 187 g / ha over an application area of 0.503 square meters (m ² ) at a spray height of 46 cm (18 cm) inches) above the top of the plant. Control plants were sprayed in the same way with the solvent without activity.
[00219] The treated plants and the control plants were placed in a greenhouse as described above and irrigated by sub-irrigation to prevent run-off of the test compounds. After 20-22 days, the condition of the test plants compared to that of the control plants was determined visually and rated on a scale of 0 to 100 percent where 0 corresponds to no injury and 100
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[00220] 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,).
[00221] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B / 100)
A = observed effectiveness of active ingredient A in the same concentration as that used in the mixture.
B = observed effectiveness of active ingredient B at the same concentration as that used in the mixture.
[00222] The tested compounds, application rates employed, tested plant species and results are given in Tables 57-66. Table 57. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and 2,4-DB Applied to Foliage under Weed Control in a Cereal Culture System.
Application Rate (gai / ha) POLCO Benzyl Ester of Compound A 2,4-DB Ob Ex 8.75 0 50 - 0 150 17 - 8.75 150 67 58
Table 58. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Dichlorprope-P Applied to Fohagem Over Weed Control in a Cereal Culture System.
Application Rate (gai / ha) VIOTR BRSNN Benzyl ester ofCompound A Dichlorprope-P Ob Ex Ob Ex 8.75 0 30 - 23 -
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Application Rate (gai / ha) VIOTR BRSNN Benzyl ester ofCompound A Dichlorprope-P Ob Ex Ob Ex 0 140 27 - 57 - 8.75 140 57 49 77 67
Table 59. Synergistic Activity of Compound A Benzyl Ester Herbicidal Compositions and MCPA Applied to Foliage Over Weed Control in a Cereal Culture System.
Application Rate (gai / ha) VIOTR POLCO BRSNN Benzyl ester ofCompound A MCPA Ob Ex Ob Ex Ob Ex 8.75 0 30 - 50 - 23 - 0 140 40 - 0 - 70 - 8.75 140 78 58 62 50 87 77
Table 60. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Mecoprope Applied to Foliage Over Weed Control in a Cereal Culture System.
Application Rate (gai / ha) BRSNN Benzyl Ester of Compound A Mecoprope-P Ob Ex 8.75 0 23 - 0 200 70 - 8.75 200 83 77
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Table 61. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Dicamba Applied to Foliage Over Weed Control in a Cereal Culture System.
Application Rate (gai / ha) AMARE POLCO BRSNN Benzyl Ester of Compound A Dicamba Ob Ex Ob Ex Ob Ex 8.75 0 60 - 50 - 23 - 0 35 53 - 13 - 8 - 8.75 35 97 81 77 57 43 30
Table 62. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Aminopyralide Applied to Foliage Over Weed Control in a Cereal Culture System.
Application Rate (gai / ha) POLCO CIRAR BRSNN Benzyl Ester of Compound A Aminopyralide Ob Ex Ob Ex Ob Ex 8.75 0 50 - 70 - 23 - 0 3 3 - 13 - 0 - 8.75 3 67 52 82 74 40 23
Table 63. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Clopyralide Applied to Foliage Over Weed Control in a Cereal Culture System.
Application Rate (gai / ha) AMARE Benzyl Ester of Compound A Clopyralide Ob Ex 8.75 0 60 - 0 50 17 - 8.75 50 73 67
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Table 64. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Picloram Applied to Foliage Over Weed Control in a Cereal Culture System.
Application Rate (gai / ha) VIOTR STEME POLCO Benzyl ester ofCompound A Picloram Ob Ex Ob Ex Ob Ex 8.75 0 30 - 70 - 50 - 0 10 3 - 0 - 40 - 8.75 10 43 32 80 70 78 70
Table 65. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Fluoxipir Applied to Foliage Over Weed Control in a Cereal Culture System.
Application Rate (gai / ha) AMARE VIOTR POLCO CIRAR Benzyl Ester of Compound A Fluroxypyr Ob Ex Ob Ex Ob Ex Ob Ex 8.75 0 60 - 30 - 50 - 70 - 0 35 33 - 10 - 23 - 3 - 8.75 35 83 73 60 37 78 62 78 71
Table 66. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Quinclorak Applied to Foliage Over Weed Control in a Cereal Culture System.
Application Rate (gai / ha) AMARE VIOTR POLCO Benzyl ester ofCompound A Quincloraque Ob Ex Ob Ex Ob Ex 8.75 0 60 - 30 - 50 -
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0 140 27 - 0 - 3 - 8.75 140 83 71 50 30 58 52
AMARE Amarantus retroflexus (L.) fedegosa, red root
VIOTR Viola tricolor (L.) violet, wild
CIRAR Cirsium arvense (L.) Scop. Thistle, Canada
POLCO Poligonum convolvulus
BRSNN Brassica napus (L.)
STEME Stellaria media (L.) Vill.
saracen, wild canola, volunteer Common Passionbird gae / ha = grams of acid equivalent per hectare gai / ha = grams of active ingredient per hectare Ob = observed value
Ex = expected value as calculated using the Colby equation DAA = days after application
Example V. Post-emergence Herbicidal Activity Assessment of Mixtures in Fodder Crops [00223] Seeds or root pieces of the desired test plant species were planted in a Sun Gro MetroMix ^® 306 planting mix, which typically has a pH of 6 , 0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 126.6 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 14-60 days in a greenhouse with a photoperiod of approximately 14 hours that was maintained at approximately 28 ° C during the day and 24 ° C at night. Nutrients and water were added on a regular basis and supplemental light was provided with 1000 Watt metal halide lamps suspended as needed. The plants were used for testing when they reached the leaf stage BBCH13 to BBCH23.
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191/202 [00224] The treatments consisted of benzyl ester of 4 amino-3- chloro-5- fluoro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) pyridine-2-carboxylic acid (Compound A), formulated as a SC, and a second herbicide alone and in combination.
[00225] The forms of compound A (compound of Formula I) tested included:
Compound A Benzyl Ester [00226] A measured aliquot of Compound A was placed in a 25 milliliter (mL) glass vial and diluted in a 1.25% (v / v) volume of Agri-Dex® culture oil concentrated to obtain stock solutions. The compost needs are based on an application volume of 12 mL at a rate of 187 liters per hectare (L / ha). Spray solutions of the second herbicide or mixtures of experimental compound 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 combinations in two ways. The formulated compounds were applied to the plant material with a suspended Mandel strip sprayer equipped with 8002E nozzles calibrated to apply 187 L / ha over an application area of 0.503 square meters (m ² ) in a 46 cm (18 cm) spray boom. inches) above the top of the average plant. The control plants were sprayed in the same way with the solvent without activity.
[00227] The treated plants and the control plants were put into
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192/202 a greenhouse as described above and irrigated by sub-irrigation to prevent run-off of test compounds. After approximately 21 days, the condition of the test plants, compared to that of the control plants, was determined visually and rated on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete death.
[00228] 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).
[00229] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: Expected = A + B - (A x B / 100)
A = observed effectiveness of active ingredient A in the same concentration as that used in the mixture.
B = observed effectiveness of active ingredient B at the same concentration as that used in the mixture.
[00230] The tested compounds, application rates employed, species of plant tested and results are given in Tables 67-75.
Table 67. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Butoxyethyl Triclopir Ester Applied to Foliage (BEE; Garlon 4) on Weed Control in a Forage System.
Application Rate (gae / ha) CENMA SONAR CIRAR CASOB Benzyl Ester of Compound A BEE triclopyr Note Exp Note Exp Note Exp Note Exp 4.4 0 70 - 65 - 30 - 38 - 8.8 0 85 - 100 - 30 - - - 17.5 0 95 - 95 - - - - -
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Application Rate (gae / ha) CENMA SONAR CIRAR CASOB Benzyl Ester of Compound A BEE triclopyr Note Exp Note Exp Note Exp Note Exp 0 35 30 - 60 - - - - - 0 50 - - - - - - 18 - 0 70 45 - 60 - 40 - - - 4.4 35 100 79 100 86 - - - - 8.8 35 100 90 100 100 - - - - 17.5 35 100 97 100 98 - - - - 4.4 50 - - - - - - 70 50 4.4 70 100 84 100 86 70 58 - - 8.8 70 100 92 100 100 85 58 - - 17.5 70 100 97 100 98 - - - -
Table 68. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Fluroxypyr Methyl Ester (ME; Starane) Applied to Leaf on Weed Control in Forage System.
Application Rate (gae / ha) CENMA SONAR TRFRE CIRAR SOOSS Benzyl Ester of Compound A MEFluroxypyr Note Exp Note Exp Note Exp Note Exp Note Exp 2.2 0 - - - - - - 25 - 15 - 4.4 0 70 - 65 - 0 - 30 - 45 - 8.8 0 85 - 100 - 10 - 30 - 100 -
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Application Rate (gae / ha) CENMA SONAR TRFRE CIRAR SOOSS Benzyl Ester of Compound A MEFluroxypyr Note Exp Note Exp Note Exp Note Exp Note Exp 17.5 0 95 - 95 - 30 - - - - - 0 35 0 - 0 - 15 - - - - - 0 70 0 - 15 - 20 - 10 - 504.4 35 100 70 100 65 30 15 - - - - 8.8 35 100 85 100 100 40 24 - - - - 17.5 35 100 95 100 95 50 41 - - - - 2.2 70 - - - - - - 35 32 100 57 4.4 70 100 70 100 70 70 20 45 37 98 72 8.8 70 100 85 100 100 90 28 60 37 98 100 17.5 70 100 95 100 96 90 44 - - - -
Table 69. Synergistic Activity of Herbicidal Ester Compositions
Benzyl Compound A and 2,4-D Dimethylamine Salt Applied to Sheet
About Weed Control in Forage System.
Application Rate (gae / ha) CENMA SINAR SONAR Benzyl Ester of Compound A DMA salt2,4-D Note Exp Note Exp Note Exp 4.4 0 70 - 80 - 65 - 8.8 0 85 - 100 - 100 - 17.5 0 95 - 100 - 95 - 0 35 30 - 35 - 20 - 0 70 50 - 80 - 85 -
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Application Rate (gae / ha) CENMA SINAR SONAR Benzyl Ester of Compound A DMA salt2,4-D Note Exp Note Exp Note Exp 4.4 35 100 79 100 87 95 72 8.8 35 100 90 100 100 100 100 17.5 35 100 97 100 100 100 96 4.4 70 100 85 100 96 95 95 8.8 70 100 93 100 100 100 100 17.5 70 100 98 100 100 100 99
Table 70. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Choline Salt 2,4-D Applied to Leaf on Weed Control in Forage System.
Application Rate (gae / ha) CASOB Benzyl ester ofCompound A Choline salt 2,4-D Note Exp 1.1 0 28 - 2.2 0 33 - 4.4 0 38 - 0 50 3 - 1.1 50 27 31 2.2 50 45 36 4.4 50 55 40
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Table 71. Synergistic Activity of Compound A Benzyl Ester Herbicidal Compositions and Picloram Potassium Salt (K + Salt; Tordon 22K) Applied to Leaf on Weed Control in Forage System.
Application Rate (gae / ha) CENMA SINAR Benzyl ester ofCompound A K ⁺ Picloram salt Note Exp Note Exp 4.4 0 70 - 80 - 8.8 0 85 - 100 - 17.5 0 95 - 100 - 0 35 20 - 30 - 0 70 50 - 70 - 4.4 35 100 76 100 86 8.8 35 100 88 100 100 17.5 35 100 96 100 100 4.4 70 100 85 98 94 8.8 70 100 93 100 100 17.5 70 100 98 100 100
Table 72. Synergistic Activity of Compound A Benzyl Ester Herbicidal Compositions and Clopyralid Monoethanolamine Salt (MEA Salt; Lontrel) Applied to Leaf on Weed Control in Forage System.
Application Rate (gae / ha) CIRAR SOOSS Benzyl Ester of Compound A MEA salt Clopyralid Note Exp Note Exp 2.2 0 25 - 15 - 4.4 0 30 - 45 -
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8.8 0 30 - 100 - 0 35 75 - 25 - 2.2 35 90 81 75 36 4.4 35 90 82 95 59 8.8 35 95 82 95 100
Table 73. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Triisopropanolammonium Aminopiralide Salt (TIPA salt, Milestone) Applied to Leaf on Weed Control in Forage System.
Application Rate (gae / ha) TRFRE SINAR SOOSS CIRAR Ester ofBenzila doCompound A Salt TIPAAminopyralide Note Exp Note Exp Note Exp Note Exp 4.4 0 0 - 80 - 15 - 25 - 8.8 0 10 - 100 - 45 - 30 - 17.5 0 30 - 100 - 100 - 30 - 0 17.5 35 - 25 - 45 - 45 - 0 35 - - 45 - - - - - 4.4 17.5 45 35 95 85 90 53 90 89 8.8 17.5 45 42 98 100 90 70 98 90 17.5 17.5 65 55 100 100 95 100 98 90 4.4 35 - - 100 89 - - - - 8.8 35 - - 100 100 - - - - 17.5 35 - - 100 100 - - - -
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Table 74. Synergistic Activity of Herbicidal Compositions of Compound A Benzyl Ester and Dimethylamine Dicamba Salt (DMA Salt; Banvel) Applied to Leaf on Weed Control in Forage System.
Application Rate (gae / ha) SIDSP SINAR CASOB Ester ofBenzila doCompound A Salt DMA Dicamba Note Exp Note Exp Note Exp 1.1 0 72 - 72 - 28 - 2.2 0 77 - 98 - 33 - 4.4 0 85 - 100 - 38 - 0 50 25 - 65 - 20 - 1.1 50 87 79 100 90 32 43 2.2 50 93 83 100 100 52 47 4.4 50 97 89 100 100 67 51
Table 75. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Aminocyclopyrachlor Applied to Leaf on Weed Control in Forage System.
Application Rate (gae / ha) TRFRE SINAR CENMA Ester ofBenzila doCompound A Aminocyclopyrachlor Note Exp Note Exp Note Exp 4.4 0 0 - 80 - 70 - 8.8 0 10 - 100 - 85 - 17.5 0 30 - 100 - 95 - 0 8.75 45 - 25 - 55 - 0 17.5 55 - 45 - 60 - 4.4 8.75 55 45 95 85 100 87
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Application Rate (gae / ha) TRFRE SINAR CENMA Ester ofBenzila doCompound A Aminocyclopyrachlor Note Exp Note Exp Note Exp 8.8 8.75 60 51 98 100 100 93 17.5 8.75 65 62 100 100 100 98 4.4 17.5 65 55 100 89 100 88 8.8 17.5 70 60 100 100 100 94 17.5 17.5 75 69 100 100 100 98
CASOB Cassia obtusifolia L. fedegoso
CENMA Centaurea maculosa LAM. Cornflower, painted
CIRAR Cirsium arvense (L.) SCOP. Thistle, Canada
SIDSP Sida spinosa L. SINAR Sinapis arvensis L. SONAR Sonchus arvensis L SOOSS Solidago L. spec. TRFRE Trifolium repens L.
malvinha mustard, wild milkweed, golden clover field, Dutch gae / ha = grams of acid equivalent per hectare gai / ha = grams of active ingredient per hectare
Obs = observed value
Exp = expected value as calculated using the Colby equation DAA = days after application
Example VI. Evaluation of Post-emergence Mixture Herbicidal Activity in Cereal Field Tests in Canada.
[00231] A post-emergency field test was conducted under commercial field conditions in Warner, Alberta, Canada. The test site was located in a commercially cultivated field of durum wheat (Triticum durum) using standard small herbicide batch research methodology. The size of the test lot ranged from 2 meters (m) x 8 m (width x length) with 4 replicates per treatment.
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The cereal crop was grown using normal cropping practices for fertilization, sowing and maintenance to ensure good crop and weed growth.
[00232] All treatments in the post-emergence field tests were applied using a backpack compressed CO2 sprayer with horizontal fan air induction nozzles (110 °) calibrated to apply 100 L / ha of spray volume at approximately 276 kPa nozzle pressure. The treatments consisted of benzyl ester of 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) pyridine-2-carboxylic acid (Compound A), formulated as a SC (suspension concentrate) and various herbicidal components alone and in combination.
[00233] Forms of Compound A (compound of Formula I) tested include:
Compound A Benzyl Ester [00234] A commercially available product of fluroxypyr-MHE (STARANE II, emulsifiable concentrate formulation, 333 gae / L) and a Halauxifene-ME formulation (GF-2645, wetting granule formulation, 200 gae / kg) were mixed in water at rates of formulated product appropriate to obtain the desired rates based on a unit area of application (hectare) to obtain the desired rates as shown. The treatments were classified as 28 to 54 days after application (DAA) compared to untreated control plants. Visual weed control was rated on a scale of 0 to
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100 percent where 0 corresponds to no injury and 100 corresponds to complete death.
[00235] All treatment results, both for the simple product and mixtures, are an average of 4 replicates. The test sites had naturally occurring weed populations. The weed spectrum included, but was not limited to, kochia and Russian thistle. 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).
[00236] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B / 100)
A = observed effectiveness of active ingredient A at the same concentration as used in the mixture.
B = observed effectiveness of active ingredient B in the same concentration as used in the mixture.
[00237] The tested compounds, application rates used, species of plant tested and results of field tests in culture are given in Tables 76 and 77.
Table 76. Synergistic Activity of Compound A Benzyl Ester and Fluroxypyr-MHE Herbicidal Compositions Applied to Weed Control Foliage in a Cereal Field Culture System when Evaluated 54 DAA (Days After Application) in Canada.
Benzyl Ester of Compound A MHE Fluroxipir Weed ControlVisual (%) - 54 DAA SASKR gae / ha gai / ha Note Exp 5 0 33 - 0 50 15 -
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Benzyl Ester of Compound A MHE Fluroxipir Weed ControlVisual (%) - 54 DAA SASKR gae / ha gai / ha Note Exp 5 50 58 43
Table 77. Synergistic Activity of Compound A Benzyl Ester Herbicidal Compositions and Halauxifene-ME Applied to Foliage under Weed Control in a Cereal Field Culture System when Evaluated 28 DAA (Days After Application) in Canada.
Benzyl Ester of Compound A ME Halauxifene Weed ControlVisual (%) - 28 DAA KCHSC gae / ha gai / ha Note Exp 5 0 65 - 0 5 63 - 5 5 93 87 KCHSC Kochia scoparia (L.) Schrad., kochia
SASKR Salsola tragus L. Russian thistle gae / ha = grams of acid equivalent per hectare gai / ha = grams of active ingredient per hectare Obs = observed value
Exp = expected value as calculated using the Colby equation DAA = days after application

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),
Fx nh ₂JL / OH N [Γ_x O cr F / 0 h ₃ c (I) or a benzyl ester thereof, and
(b) a synthetic auxin herbicide selected from: 2- (2,4-dichlorophenoxy) acetic acid with Nmethylmethanamine,
[2]
2- (2,4-dichlorophenoxy) 2-hydroxy-N, N, Ntrimethylethanamine,
2- (2,4-dichlorophenoxy) 2-ethylhexyl acetate, 2- (4-chloro-2-methylphenoxy) acetic acid, 2- (4-chloro-2-methylphenoxy) 2-ethylhexyl acetate 2 - [( 3,5,6-trichloro-2-pyridinyl) oxy] acetic compound with N, N-diethylethanamine,
2 - ((3,5,6-trichloropyridin-2-yl) oxy) 2-hydroxy acetateN, N, N-trimethylethanamine,
2 - [(3,5,6-trichloro-2-pyridinyl) oxy] 2-butoxyethyl acetate,
Methyl heptyl fluroxypyr ester,
Dimethylammonium Dicamba Salt,
Halauxifen-methyl,
Quinclorac,
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Halauxifene Potassium Salt, 2- (2,4-dichlorophenoxy) butyric acid, Dichlorprop-P, Mecoprop-P, Dicamba, Aminopyralide, Picloram, Fluroxypyr, Fluroxypyr methyl ester, Picloram potassium salt, 3,6- dichloro-2-pyridinecarboxylic with 2aminoethanol, or
4 'amino-3,6-dichloropyridine-2-carboxylic acid with 1,1', 1-nitrilotris [2-propanol], when (b) it is 2- (2,4-dichlorophenoxy) acetic acid with Nmethylmethanamine, the weight ratio of (a) to (b) is 1: 2 to 1:64, when (b) is 2- (2,4-dichlorophenoxy) 2-hydroxy-N, N, N-trimethylmethanamine acetate, the by weight from (a) to (b) is 1: 2 to 1: 110, when (b) is 2- (2,4-dichlorophenoxy) 2-ethylhexyl acetate, the weight ratio from (a) to ( b) is 1: 4 to 1:64, when (b) is 2- (4-chloro-2-methylphenoxy) acetic acid, the weight ratio from (a) to (b) is 1: 2 to 1 : 32, when (b) is 2- (4-chloro-2-methylphenoxy) 2-ethylhexyl acetate, the weight ratio from (a) to (b) is 1: 2.2 to 1:35, when (b) is 2 - [(3,5,6-trichloro-2-pyridinyl) oxide] acetic acid composed of N, N-diethylethanamine, the weight ratio from (a) to (b) is 1: 2 to 1:45, when (b) is 2 - ((3,5,6-trichloropyridin-2-yl) oxy) 2-hydroxy-N, N, N-trimethylethanamine acetate, the weight ratio of (a) for (b) is
Petition 870190038494, of 04/24/2019, p. 5/12
[3]
3/5 of 1: 1.7 to 1:32, when (b) is 2 - [(3,5,6-trichloro-2-pyridinyl) oxy] 2-butoxyethyl acetate, the ratio of (a) to (b ) is 1: 2 to 1:32, when (b) is methyl heptyl ester fluroxypyr, the weight ratio of (a) to (b) is 1: 2 to 1:35, when (b) is salt Dimethylammonium Dicamba, the weight ratio from (a) to (b) is 1: 3.3 to 1:64, when (b) is Halauxifen-methyl, the weight ratio from (a) to (b) is 10: 1 to 1: 2, when (b) is Quinclorac, the weight ratio from (a) to (b) is 1: 6.6 to 1:64, when (b) is Halauxifene potassium salt , the weight ratio from (a) to (b) is 1: 1 to 1: 2, when (b) is 2- (2,4-dichlorophenoxy) butyric acid, the weight ratio from (a) to ( b) is 1: 17.1, when (b) is Dichlorprop-P, the weight ratio from (a) to (b) is 1:16, when (b) is Mecoprop-P, the weight ratio from (a) to (b) is 1: 22.9, when (b) is Dicamba, the weight ratio from (a) to (b) is 1: 4, when (b) is Aminopyralide, the proportion in weight from (a) to (b) is 2.9: 1, when (b) is Picloram, the ratio of (a) to (b) is 1: 1.1, when (b) is Fluroxypyr, a weight ratio of (a) to (b) is 1: 4, when (b) methyl ester fluroxypyr, the ratio in (a) to (b) is 1: 2 to 1:16, when ( b) is the potassium salt of Picloram, the weight ratio from (a) to (b) is from 1: 2 to 1:16,
Petition 870190038494, of 04/24/2019, p. 6/12
[4]
4/5 when (b) is 3,6-dichloro-2-pyridinecarboxylic acid with 2aminoethanol, the weight ratio of (a) to (b) is 1: 4 to 1:16, when (b) is composed of acid 4-amino-3,6-dichloropyridine2-carboxylic acid with 1,1 ', 1-nitrilotris [2-propanol], the weight ratio from (a) to (b) is from 1: 1 to 1: 8, and when (b) is aminocyclopyrachlor, the weight ratio from (a) to (b) is 2: 1 to 1: 4.
2. Composition according to claim 1, characterized by the fact that it also comprises an agriculturally acceptable adjuvant or vehicle.
3. Composition according to claim 1 or 2, characterized by the fact that it also comprises a herbicide protector.
4. Method for controlling undesirable vegetation, characterized by the fact that it comprises the step of contacting a plant, the plant being an undesirable vegetation, or its location, soil or water, with soil or water allowing the growth of vegetation undesirable, 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, cereals, wheat, barley, oats, rye, sorghum, corn, sugar cane, sunflower, rapeseed for oil seed, sugar cane, soybeans, cotton, pineapple, pastures, grasslands, pastures, fallow, peat, tree and vine orchards, aquatic, industrial vegetation management (IVM) or straight sowed, ROW in water and transplanted.
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[6]
6. Method according to claim 4 or 5, characterized by the fact that (a) and (b) are applied preemergently 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, 5enolpyruvylshiquimate-3-phosphate (EPSP) synthase, glufosinate, glutamine synthase inhibitor, dicamba, phenoxy auxin, pyridyloxy auxin, synthetic auxin, auxin transport inhibitor, aryloxyphenoxypropionate, cyclohexanedione, phenylpyrazoline, acetyl CoA carboxylase (ACCase) inhibitor, imidazolinone, sulfonylurea, pyrimidinylthiopyronylone, sulfinylamine, triazine, triazine, triazine acetohydroxy acid synthase (AHAS), 4-hydroxyphenyl-pyruvate dioxigenase (HPPD) inhibitor, phytene desaturase inhibitor, carotenoid biosynthesis inhibitor, protoporphyrinogen oxidase (PPO) inhibitor, cellulose biosynthesis inhibitor, mitosis inhibitor, mitosis inhibitor very long chain fatty acid inhibitor, biosynthesis inhibitor and fatty acid and lipid, inhibitor of photosystem I, inhibitor of photosystem II,) triazine or bromoxynil.
[8]
8. Method, according to claim 7, characterized by the fact that the tolerant culture has multiple or stacked characteristics conferring tolerance to multiple herbicides or multiple modes of action.
[9]
Method according to any one of claims 4 to 8, characterized in that the undesirable vegetation comprises a herbicide-resistant or tolerant weed.

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

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

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2018-09-11| B07A| Application suspended after technical examination (opinion) [chapter 7.1 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| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

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

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2020-02-04| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 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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US201261675070P| true| 2012-07-24|2012-07-24|

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US13/833,923|US8912120B2|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 synthetic auxin herbicides|

---