HERBICIDAL COMPOSITIONS UNDERSTANDING ACID 4 AMINO-3- CHLORINE-5-FLUOR-6- (4-CHLORINE-2-FLUORO-3METO

专利摘要:
herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or a derivative thereof and a protoporphyrinogen oxidase inhibitor. the present invention relates to synergistic herbicidal compositions containing (a) a compound of formula (1): 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or an agriculturally acceptable salt or ester thereof and (b) a protoporphyrinogen oxidase inhibitor, for example, acifluorphene, azafenidene, bifenox, carfentrazone-ethyl-ethyl, flumioxazin, ipfencarbazone, oxadona, oxadone, oxadiazone, oxadiazone , pyraclonil, piraflufen-ethyl and saflufenacil, or a salt or ester thereof. the compositions and methods provided here provide control of undesirable vegetation, for example, in no-till rice, water-sown and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, maize (with) or maize (maize), sugar cane, sunflower, rapeseed, canola, sugar beet, soy, cotton, pineapple, grassland, lawns, natural grazing land, uncultivated land, grass, tree orchards and vines, aquatic, plantation crops, vegetables, industrial vegetation control (ivm) and easements (row).
公开号:BR102013018510B1
申请号:R102013018510-8
申请日:2013-07-19
公开日:2020-05-26
发明作者:Carla Yerkes；Richard Mann；Paul Schmitzer；Norbert Satchivi
申请人:Dow Agrosciences Llc；
IPC主号:

专利说明:

Invention Patent Descriptive Report for HERBICIDAL COMPOSITIONS UNDERSTANDING ACID 4 AMINO-3-CHLORO-5-FLUOR-6- (4-CHLORINE-2-FLUORO-3METOXYPHENIL) PYRIDINE-2-CARBOXYLIC OR A DERIVATIVE OF THE SAME AND AN INHIBITORIDE OF PROTO , AND METHOD FOR CONTROL OF UNDESIRABLE VEGETATION. PRIORITY CLAIM
[0001] This application claims the benefit of the Patent Application
Provisional US 61 / 675,067, filed on July 24, 2012, and US Patent Application 13 / 840,346, filed on March 15, 2013, a description of each of which is incorporated herein by reference in its entirety.
FIELD
[0002] Herbicidal compositions are provided here comprising (a) 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3methoxyphenyl) pyridine-2-carboxylic acid or an agriculturally acceptable ester or salt and (b) a protoporphyrinogen oxidase inhibitor. Also provided here are methods of controlling undesirable vegetation comprising applying (a) 4-amino-3-chloro-5-fluoro-6 (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-carboxylic acid or an agriculturally acceptable ester or salt thereof and (b) a protoporphyrinogen oxidase inhibitor.
BACKGROUND
[0003] Protecting crops from weeds and other vegetation that inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in controlling undesirable crops. Chemical herbicides of many types have been described in the literature and a large number are in
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2/112 commercial use. However, there remains a need for compositions and methods that are effective in controlling undesirable vegetation.
SUMMARY
[0004] Herbicidal compositions are provided herein comprising a herbicidally effective amount of (a) a compound of Formula (I)
_Hi c- ° ®
[0005] or an agriculturally acceptable ester or salt thereof, and (b) a protoporphyrinogen oxidase inhibitor. The compositions can also contain an agriculturally acceptable adjuvant or vehicle. Also provided here are methods of controlling undesirable vegetation comprising applying (a) a compound of Formula (I) or an agriculturally acceptable ester or salt thereof and (b) a protoporphyrinogen oxidase inhibitor, for example, acifluorfen, azafenidene, bifenox, carfentrazone-ethyl, flumioxazin, ipfencarbazone, oxadiargyl, oxadiazone, oxyfluene, pentoxazone, pyraclonil, piraflufen and saflufenacil, or an agriculturally acceptable salt or ester thereof.
[0006] Several modalities are listed below. In the embodiments, the ratio of compound (a) to compound (b) can be expressed in weight to weight units (g to g), gae / ha to gae / ha or gae / ha to gai / ha.
[0007] 1. A synergistic herbicidal composition comprising a herbicidally effective amount of (a) a compound of Formula (I)
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h ₃ c '° ®
[0008] or an agriculturally acceptable ester or salt thereof and (b) a protoporphyrinogen oxidase inhibitor.
[0009] 2. The mode 1 composition, wherein (a) is a C1-4 alkyl or benzyl ester of compound (I).
[00010] 3. The mode 2 composition, wherein (a) is a benzyl ester of compound (I).
[00011] 4. The mode 1 composition, where (a) is the compound of Formula (I), which is carboxylic acid.
[00012] 5. The composition of any one of modalities 1 to 4, in which (b) is acifluorfen, azafenidene, bifenox, carfentrazone-ethyl, flumioxazin, ipfencarbazone, oxadiargyl, oxadiazone, oxyfluorfen, pentoxazone, pyraclonil, piraflufen-piraflufen-eira saflufenacil, or agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof.
[00013] 6. The composition of modality 1, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is acifluorphene sodium.
[00014] 7. The composition of modality 1, in which (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is azafenidene.
[00015] 8. The composition of modality 1, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is biphenox. [00016] 9. The mode 1 composition, in which (a) is the compound of Formula (I) or an agrically acceptable benzyl ester and (b) is carfentrazone-ethyl.
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[00017] 10. The composition of modality 1, in which (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is ipfencarbazone.
[00018] 11. The composition of modality 1, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is flumioxazin.
[00019] 12. The composition of modality 1, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is oxadiargyl.
[00020] 13. The mode 1 composition, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is oxadiazone.
[00021] 14. The composition of modality 1, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is oxyfluorfen.
[00022] 15. The mode 1 composition, in which (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is pentoxazone.
[00023] 16. The composition of modality 1, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is pyraclonyl.
[00024] 17. The composition of modality 1, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is piraflufen-ethyl.
[00025] 18. The composition of modality 1, in which (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is saflufenacil.
[00026] 19. The composition of any one of modalities 1 to 18, also comprising a herbicidal protector.
[00027] 20. The composition of modality 5, in which the ratio of
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5/112 weight of the compound of Formula (I) or ester or agriculturally acceptable salt thereof for acifluorphene or agriculturally acceptable salt thereof is about 1: 210 to about 9: 1.
[00028] 21. The composition of mode 5, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to azafenidene or agriculturally acceptable salt thereof is from about 1: 220 to about 10: 1.
[00029] 22. The composition of modality 5, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to bifenox or carboxylic acid, carboxylate salt, or agriculturally acceptable ester thereof is about 1: 500 to about 3: 1.
[00030] 23. The composition of modality 5, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to carfentrazone-ethyl or ester or agriculturally acceptable salt thereof is about 1: 60 to about 86: 1.
[00031] 24. The composition of modality 5, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to ipfencarbazone or agriculturally acceptable salt thereof is about 1: 250 to about 5: 1.
[00032] 25. The composition of modality 5, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to flumioxazin or agriculturally acceptable salt thereof is from about 1: 300 to about 17: 1.
[00033] 26. The composition of modality 5, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to oxadiargyl of agriculturally acceptable salt thereof is from about 1: 1100 to about 6: 1.
[00034] 27. The composition of modality 5, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to oxadiazone or agriculturally acceptable salt thereof is
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6/112 from about 1: 2240 to about 10: 1.
[00035] 28. The composition of modality 5, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to oxyfluorfen is from about 1: 1120 to about 3: 1.
[00036] 29. The composition of modality 5, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to pentoxazone or agriculturally acceptable salt thereof is about 1: 225 to about 6: 1.
[00037] 30. The composition of modality 5, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to pyraclonil or agriculturally acceptable salt thereof is about 1: 180 to about 9: 1.
[00038] 31. The composition of modality 5 wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to piraflufen-ethyl or carboxylic acid, carboxylate salt, or agriculturally acceptable ester thereof is from about 1: 6 to about 150: 1.
[00039] 32. The composition of any of the modalities 5 in which the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to saflufenacil or agriculturally acceptable salt thereof is about 1: 100 to about 60: 1. [00040] 33. The composition of any one of embodiments 1 to 32, also comprising an agriculturally acceptable adjuvant or vehicle.
[00041] 34. The composition of any of modalities 1 to 32 that is synergistic as determined by the Colby equation.
[00042] 35. A method of controlling undesirable vegetation which comprises contacting the vegetation or its location with or applying to the soil or water, to prevent the appearance or growth of vegetation, the composition of any one of modalities 1 to 34.
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[00043] 36. An undesirable vegetation control method which comprises contacting the vegetation or location with or applying to the soil or water, to prevent the appearance or growth of vegetation, a herbicidally effective amount of (a) a compound of the Formula (I)
h ₃ c '° ®
[00044] or an agriculturally acceptable ester or salt thereof and (b) a protoporphyrinogen oxidase inhibitor.
[00045] 37. The method of modality 35 or 36, in which the method is practiced in at least one member of the group consisting of no-till rice, water-sown and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn (maize), maize (maize), sugar cane, sunflower, rapeseed, canola, sugar beet, soy, cotton, pineapple, pastures, lawns, natural pasture land, uncultivated land, grass, orchards of tree and vines, aquatic, plantation crops, vegetables, industrial vegetation control (IVM) or easements (ROW).
[00046] 38. The method of modality 35 or 36, in which the unwanted vegetation is immature.
[00047] 39. Method 35 or 36, in which (a) and (b) are applied to water.
[00048] 40. Method 39, in which the water is part of a flooded rice flood.
[00049] 41. Method 35 or 36, in which (a) and (b) are applied pre-emergently to weed or harvest.
[00050] 42. The method of modality 35 or 36, in which (a) and (b)
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8/112 are applied post-emergently to weed or harvest. [00051] 43. Method 35 or 36, in which undesired vegetation is controlled in crops tolerant to glyphosate-, 5-enolpyruvylchiquimate-3-phosphate (EPSP) synthase-, glufosinate-, glutamine synthase-inhibitor , dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanediona-, phenylpyrazoline-, acetyl CoA carboxylase inhibitor (ACCase) -, imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) inhibitor or acetohydroxy acid synthase (AHAS) inhibitor -, 4-hydroxyphenylpyruvate dioxigenase (HPPD) inhibitor, phytenoinase inhibitor, phytene inhibitor -, protoporphyrinogen oxidase (PPO) inhibitor -, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor dio-, photosystem inhibitor I-, photosystem inhibitor II-, triazine-, or bromoxynil-.
[00052] 44. Modality method 43, in which the tolerant harvest has multiple or stacked traits that confer tolerance to multiple herbicides or multiple modes of action.
[00053] 45. Method 35 or 36, in which undesirable vegetation comprises a herbicide-resistant or tolerant weed.
[00054] 46. The method of modality 45, in which the resistant or tolerant weed is a biotype with resistance or tolerance to multiple herbicides, multiple chemical classes, multiple modes of action of the herbicide or through multiple resistance mechanisms. [00055] 47. Method 45, wherein the resistant or tolerant weed is a biotype resistant or tolerant to acetolactate synthase (ALS) inhibitors or acetohydroxy synthase acid (AHAS),
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9/112 photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylchiquime-3 phosphate (EPSP) synthase (EPSP) synthase inhibitors, microtubule assembly inhibitors, inhibitors of fatty acid and lipid synthesis, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid inhibitors (VLCFA), phytene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4 inhibitors -hydroxyphenyl-pyruvate-dioxigenase (HPPD), mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes of action, quinclorac, arylaminopropionic acids, difenzoquat, endotall, or organoarsenical.
[00056] 48. The composition of any one of modalities 1 to 5, wherein (b) is acifluorfen, azafenidene, bifenox, carfentrazone-ethyl, flumioxazin, ipfencarbazone, oxadiargyl, oxadiazone, oxifluorfen, pentoxazone, pyraclonil, piraflen-eira piraflen saflufenacil, or agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof.
[00057] 49. The mode 1 composition, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is acifluorphene sodium.
[00058] 50. The mode 1 composition, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is azafenidene.
[00059] 51. The mode 1 composition, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is biphenox. [00060] 52. The mode 1 composition, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is carfentrazone-ethyl.
[00061] 53. The composition of modality 1, where (a) is the compound
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10/112 of Formula (I) or an agriculturally acceptable benzyl ester and (b) is ipfencarbazone.
[00062] 54. The mode 1 composition, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is flumioxazin.
[00063] 55. The mode 1 composition, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is oxadiargyl.
[00064] 56. The mode 1 composition, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is oxadiazone.
[00065] 57. The mode 1 composition, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is oxyfluorfen.
[00066] 58. The mode 1 composition, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is pentoxazone.
[00067] 59. The mode 1 composition, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is pyraclonyl.
[00068] 60. The mode 1 composition, wherein (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is piraflufen-ethyl.
[00069] 61. The mode 1 composition, in which (a) is the compound of Formula (I) or an agriculturally acceptable benzyl ester and (b) is saflufenacil.
[00070] 62. The composition of modality 48, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to acifluorphene, acifluorphene sodium, or agriculturally acceptable salt thereof is about 1 : 210 to about 9: 1.
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[00071] 63. The mode 48 composition, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to azafenidene is from about 1: 220 to about 10: 1.
[00072] 64. The composition of modality 48, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to bifenox or carboxylic acid, carboxylate salt, or agriculturally acceptable ester thereof is about 1: 500 to about 3: 1.
[00073] 65. The composition of modality 48, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to carfentrazone-ethyl or ester or agriculturally acceptable salt thereof is about 1: 60 to about 86: 1.
[00074] 66. The composition of modality 48, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to ipfencarbazone or agriculturally acceptable salt thereof is about 1: 250 to about 5: 1.
[00075] 67. The mode 48 composition, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to flumioxazin or agriculturally acceptable salt thereof is about 1: 300 to about 17: 1.
[00076] 68. The composition of modality 48, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to oxadiargyl of agriculturally acceptable salt thereof is from about 1: 1100 to about 6: 1.
[00077] 69. The composition of modality 48, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to oxadiazone or agriculturally acceptable salt thereof is from about 1: 2240 to about 10: 1.
[00078] 70. The mode 48 composition, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to oxyfluorfen is from about 1: 1120 to about 3: 1.
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[00079] 71. The composition of modality 48, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to pentoxazone or agriculturally acceptable salt thereof is about 1: 225 to about 6: 1.
[00080] 72. The composition of modality 48, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to pyraclonyl or agriculturally acceptable salt thereof is about 1: 180 to about 9: 1.
[00081] 73. Modality composition 48, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to piraflufen-ethyl or carboxylic acid, carboxylate salt, or agriculturally acceptable ester thereof is about 1: 6 to about 150: 1.
[00082] 74. Modality composition 48, wherein the weight ratio of the compound of Formula (I) or ester or agriculturally acceptable salt thereof to saflufenacil or agriculturally acceptable salt thereof is about 1: 100 to about 60: 1.
[00083] 75. The composition of any one of modalities 1 to 34 or 48 to 74, also comprising an adjuvant or agriculturally acceptable vehicle.
[00084] 76. The composition of any of modalities 1 to 34 or 48 to 74, also comprising a herbicidal protector.
[00085] 77. The composition of any of modalities 1 to 34 or 48 to 74, in which the ratio of compound (a) and compound (b) are present in proportions that result in synergistic herbicidal activity as determined by the Colby equation .
[00086] 78. A method of controlling undesirable vegetation which comprises contacting the vegetation or its location with or applying to the soil or water, to prevent the appearance or growth of vegetation, the composition of any of modalities 1 to 34 or 48 to 74.
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[00087] 79. A method according to any of modalities 35 to 47, in which the unwanted vegetation is immature. DETAILED DESCRIPTION
DEFINITIONS
[00088] As used here, the compound of Formula (I) has the following structure:
h ₃ w ^{/ 0 (i)}
[00089] The compound of Formula (I) can be identified by the name 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methoxyphenyl) -5-fluoro-pyridine-2-carboxylic acid and has been described in the Patent United States 7,314,849 (B2), which is incorporated herein by reference in its entirety. Exemplary uses of the compound of Formula (I) include controlling undesirable vegetation, including grass, peppermint weeds and broadleaf, in multiple non-harvest and harvest situations.
[00090] Without being limited to any theory, protoporphyrinogen oxidase inhibitors are believed to interfere with the production of chlorophyll, lipid and protein, causing plant cells to dry and disintegrate. Exemplary protoporfinogen oxidase inhibitors include, but are not limited to, acifluorfen, azafenidene, bifenox, carfentrazone-ethyl, flumioxazin, ipfencarbazone, oxadiargyl, oxadiazone, oxyfluene, pentoxazone, pyraclonil, and pyraclophen-ethanol derivatives.
[00091] As used here, acifluorfen is 5- [2-chloro-4 (trifluoromethyl) phenoxy] -2-nitrobenzoic acid. Acifluorfen has the following structure:
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[00092] The herbicidal activity of acifluorfen is exemplified in Tomlin, C., ed. A World Compendium The Pesticide Manual. 15 Alton edition: BCPC Publications, 2009 (hereinafter The Pesticide Manual, Fifteenth Edition, 2009). An exemplary form of acifluorfen includes its sodium salt. Exemplary uses of acifluorfen include its use for post-emergence control of broadleaf weeds in soybeans and rice.
[00093] As used here, azafenidin is 2- [2,4-dichloro-5- (2propynyloxy) phenyl] -5,6,7,8-tetrahydro-1,2,4-triazole [4,3- a] pyridin-3 (2H) one and has the following structure:
[00094] Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth edition, 2009. Exemplary uses of azafenidin include as a pre-emergence herbicide, and, in a mixture, post-emergence, on citrus plants, grapevines, olives, cane sugar and other perennial crops.
[00095] As used here, bifenox is methyl 5- (2,4-dichlorophenoxy) -2 nitrobenzoate. Bifenox has the following structure:
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[00096] The herbicidal activity of bifenox is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of bifenox include its use for the control of backyard grass and peppermint, for example, in transplanted rice.
[00097] As used here, carfentrazone-ethyl is a, 2-dichloro-5- [4 (difluoromethyl) -4,5-dihydro-3-methyl-5-oxo-1 H-1,2,4- ethyl triazol-1-yl] -4fluorbenzenepropanoate. Carfentrazone-ethyl has the following structure:
[00098] The herbicidal activity of carfentrazone-ethyl is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of carfentrazone-ethyl include its use for post-emergence control of a wide range of broadleaf weeds, for example example, in cereals.
[00099] As used here, flumioxazin is 2- [7-fluoro-3,4-dihydro-3 oxo-4- (2-propynyl) -2H-1,4-benzoxazin-6-yl] -4, 5,6,7-tetrahydro-1H isoindole-1,3 (2H) -dione. Flumioxazin has the following structure:
[000100] The herbicidal activity of flumioxazin is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of flumioxazin include its use for the pre-emergence control of broadleaf weeds and grasses, for example, in soybean crops and trees and grapevine.
[000101] As used here, oxadiargyl is 3- [2,4-dichloro-5- (2Petition 870200027098, of 28/02/2020, p. 18/125
16/112 propynyloxy) phenyl] -5- (1,1-dimethylethyl) -1,3,4-oxadiazole-2 (3H) -one.
Oxadiargila has the following structure:
[000102] Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of oxadiargyl include its use for the pre-emergence and early post-emergence control of broadleaf weeds, grasses and annual peppermint, for example, in rice, sunflowers, potatoes, vegetables, sugar cane, fruit trees, and citrus plants.
[000103] As used here, oxadiazone is 3- [2,4-dichloro-5- (1methylethoxy) phenyl] -5- (1,1-dimethylethyl) -1,3,4-oxadiazole-2 (3H) -one . Oxadiazone has the following structure:
[000104] Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of oxadiazone include its use for the control of mono- and dicotyledonous weeds, for example, in rice, and pre-emergence control of creeper, annual broadleaf weeds and grass; and post-emergence control of annual broad-leaved vines and weeds, for example, in carnations, gladiolus, roses, fruit trees and shrubs, vines, ornamental trees and shrubs, hops, cotton, rice, soybeans, sunflower, onions and grass.
[000105] As used herein, oxyfluorfen is 2-chloro-1- (3-ethoxy-4-nitrophenoxy) -4- (trifluoromethyl) benzene. It has the following structure:
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F
F
THE
The CH
[000106] Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth edition, 2009. Exemplary uses of oxyfluorfen include its use for pre- and post-emergence control of grass and broadleaf weeds, for example, in crops tropical and subtropical.
[000107] As used here, pentoxazone is 3- [4-chloro-5 (cyclopentyloxy) -2-fluorophenyl] -5- (1-methylethylidene) -2,4-oxazolidinedione and has the following structure:
[000108] Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth edition, 2009. Exemplary uses of pentoxazone include its use for the pre- and post-emergence control of Echinocloa spp. and Monchoria vaginalis, for example, in flooded rice, before, during or after transplantation.
[000109] As used here, pyraclonyl is 1- (3-chloro-4,5,6,7-tetrahydropyrazolo [1,5-a] pyridin-2-yl) -5- (methyl-2-propynylamino) -1H -pyrazol-4carbonitrile and has the following structure:
HC
[000110] Exemplary uses of piraclonil include its use for weed control in rice.
[000111] As used here, piraflufen-ethyl is 2-chloro-5- (4-chloro-5Petition 870200027098, of 02/28/2020, page 20/125
18/112 diflúormetóxi-1-methylpyrazol-3-yl) -4-fluorophenoxy] ethyl acetate.
Piraflufen-ethyl presents the following structure:
[000112] The herbicidal activity of piraflufen-ethyl is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of piraflufen-ethyl include its use for post-emergence control of broadleaf weeds, for example, in cereals .
[000113] As used here, saflufenacil is 2-chloro-5- [3,6-dihydro-3methyl-2,6-dioxo-4- (trifluoromethyl) -1 (2H) -pyrimidinyl] -4-fluorine-M- [[methyl (1methylethyl) amino] sulfonyl] benzamide and saflufenacil has the following structure:
[000114] Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of saflufenacil include its use for leaf and residual control of broadleaf weeds.
[000115] As used here, herbicide means a compound, for example, an active ingredient that kills, controls or otherwise adversely modifies the growth of plants.
[000116] As used here, an amount of vegetation control or herbicidally effective is an amount of active ingredient that adversely causes a modification effect to vegetation, for example, by deviating from normal development, killing, performing regulation, causing desiccation , causing the delay, and
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Similar 19/112.
[000117] As used here, control of undesirable vegetation means prevention, reduction, extermination, 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 the vegetation or location thereof, for example, application to the area adjacent to the vegetation, as well as pre-emergence, post-emergence, leaf applications (disseminated, direct, associated, localized, mechanical , over the top, or salvation), and in water (emerged and submerged, scattered, localized, mechanical vegetation, injected with water, scattered granular, localized granular, agitated flask, or chain spray) using manual application methods, backpack, machine, tractor, or aerial (airplane and helicopter).
[000118] As used here, plants and vegetation include, but are not limited to, germinating seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and established vegetation.
[000119] As used herein, agriculturally acceptable esters and salts refer to salts and esters that exhibit herbicidal activity, or that are or can be converted into plants, water, or soil for the referenced herbicide. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, for example, into plants, water, or soil, to the corresponding carboxylic acid which, depending on the pH, can be in dissociated form or not dissociated.
[000120] Exemplary salts include those derived from alkali and alkaline earth metals and those derived from ammonia and amines. Exemplary cations include cations of sodium, potassium, magnesium, and
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Formula 20/112:
R1R ² R ³ R ⁴ N ⁺
[000121] wherein R ¹ , R ² , R ³ and R ⁴ each independently represent hydrogen or C1-C12 alkyl, C3-C12 alkenyl or C3-C12 alkynyl, each of which is optionally substituted by one or more groups hydroxy, 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 dysfunctional function containing one to twelve carbon atoms and up to two oxygen and 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 benzylamine. tetraalkylammonium hydroxide, such as tetraalkylammonium hydroxide, such as tetramethylammonium hydroxide or choline hydroxide.
Exemplary esters include those derived from C1-C12 alkyl, C3-C12 alkenyl, C3-C12 alkynyl or C7-C10 aryl substituted alkyl alcohols, such as methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethyl-hexanol , butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or benzyl alcohols not substituted or substituted. Benzyl alcohols can be substituted with 1 to 3 substituents independently selected from halogen, C1-C4 alkyl or C1-C4 alkoxy. Ethers can be prepared by coupling 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); the acids being reacted as alkylating agents such as alkylates or alkyl sulfonates in the presence of a base such as triethylamine or
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21/112 lithium carbonate; reacting the corresponding acid chloride of an acid with an appropriate alcohol; reacting the corresponding acid with an appropriate alcohol in the presence of an acid catalyst or by transesterification.
COMPOSITIONS AND METHODS
[000123] Herbicidal compositions are provided herein comprising a herbicidally effective amount of (a) a compound of Formula (I)
h ₃ c ^ ° ®
[000124] or an agriculturally acceptable ester or salt thereof, and (b) a protoporphyrinogen oxidase inhibitor. In some embodiments, the protoporphyrinogen oxidase inhibitor is acifluorphene, azafenidene, bifenox, carfentrazone-ethyl, flumioxazin, ipfencarbazone, oxadiargyl, oxadiazone, oxyfluene, pentoxazone, pyraclonyl, piraflufen-ethylic, and is even orally.
[000125] Methods of controlling undesirable vegetation are also provided here comprising contacting the vegetation or the location thereof, that is, area adjacent to the plant, with or applying to the soil or water, to prevent the appearance or growth of vegetation, an amount herbicidally effective (a) compound of Formula (I) and (b) a protoporphyrinogen oxidase inhibitor. In certain embodiments, the methods employ the compositions described here.
[000126] In addition, in some embodiments, the combination of compound (I) or ester or agriculturally acceptable salt thereof and a protoporphyrinogen oxidase inhibitor, or an agriculturally acceptable salt or ester thereof exhibits synergism, for example,
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22/112 herbicidal active ingredients are more effective in combination than when applied individually. Synergism was defined as an interaction of two or more factors so that what is done when combined is greater than the predicted effect, based on the response of each factor applied separately. Senseman, S., ed. Herbicide Handbook. 9th Edition. Lawrence: Weed Science Society of America, 2007. In certain embodiments, the compositions exhibit synergy as determined by Colby's equation. Colby, SR 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15: 20-22.
[000127] 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 embodiments, a benzyl, substituted benzyl, or C1-4 alkyl, for example, n-butyl ester is employed. In certain embodiments, the benzyl ester is used.
[000128] In some embodiments, the compound of Formula (I) or the salt or ester thereof and acifluorphene, azafenidene, bifenox, carfentrazonaethyl, flumioxazin, ipfencarbazone, oxadiargyl, oxadiazone, oxyfluene, pentoxazone, pyraclone, pyraclone, pyraclene, pyraclene, pyraclene, pyracenyl, pyracenyl, pyraclene, pyracenyl, pyracenyl, pyracenyl, pyracenyl, pyracenyl, pyracenyl, pyracenyl, pyracenyl, pyracenyl, pyracenyl, pyracenyl, pyracenyl, pyracenyl, pyracenyl, pyracenyl and piraflen. an agriculturally acceptable salt or ester thereof are formulated into a composition, mixed in a tank, applied simultaneously, or sequentially applied.
[000129] The herbicidal activity is exhibited by the compounds when they are applied directly to the plant or to the plant site at any stage of development. The observed effect depends on the species of plant to be controlled, the stage of development of the plant, the parameters of application of dilution and spray droplet size, particle size of solid components, conditions
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23/112 environmental conditions at the time of use, the specific compound used, the specific adjuvants and vehicles used, the type of soil, and the like, as well as the amount of chemical 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, preemergence application, or application in water to flooded flooded rice or water bodies (for example, swimming pools, lakes and streams), to relatively immature undesirable vegetation for maximum weed control.
[000130] In some embodiments, the compositions and methods provided here are used to control weeds in crops, including, however, not limited to no-till rice, water-sown and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, maize (corn) / maize (maize), sugar cane, sunflower, rapeseed, canola, sugar beet, soy, cotton, pineapple, pastures, lawns, natural grazing land, uncultivated land, grass, tree orchards and vines, aquatic, plantation crops, vegetables, industrial vegetation control (IVM) and easements (ROW).
[000131] In certain embodiments, the compositions and methods provided here are used to control weeds in rice. In certain modalities, rice is no-till rice, water seeding, or transplanted rice.
[000132] The compositions and methods described here can be used to control undesirable vegetation in glyphosate-tolerant crops, tolerant to 5-enolpyruvylchiquimate-3-phosphate (EPSP) synthase, tolerant to glufosinate, tolerant to glutamine synthase inhibitor, tolerant to dicamba, phenoxy auxin tolerant, pyridyloxy auxin tolerant, auxin tolerant, tolerant
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24/112 to the auxin transport inhibitor, tolerant to aryloxyphenoxypropionate, tolerant to acetyl CoA carboxylase (ACCase) inhibitor, tolerant to sulfonylurea, tolerant to pyrimidinylthiobenzoate, tolerant to triazolopyrimidine, tolerant to sulfonylaminocarbonate, tolerant to imidazolone, tolinylone and tolinylone. synthase (ALS) or acetohydroxy acid synthase (AHAS), tolerant to the 4-hydroxyphenylpyruvate dioxigenase (HPPD) inhibitor, tolerant to the phytene desaturase inhibitor, tolerant to the carotenoid biosynthesis inhibitor, tolerant to the protoporphyrinogen oxidase inhibitor ( 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 II inhibitor, tolerant to triazine, and tolerant to bromoxynil (such as, but not limited to soy, cotton, canola / rapeseed, rice, cereals, corn, sorghum, sunflower, sugar beet, sugar cane, grass, etc.), for example, in conjunction with glyphosate, EPSP synthase inhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, ACC inhibitors, sulfinone inhibitors, ACCase inhibitors pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD inhibitors, phyteno desaturases inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors, mitocyte inhibitors, mitocyte inhibitors, mitosis inhibitors very long chain, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem inhibitors II, triazines, and bromoxynil. Compositions and methods can be
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25/112 used to control undesirable vegetation in crops that have multiple or stacked traits that confer tolerance to multiple chemicals / 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.
[000133] The compositions and methods can be used to control undesirable vegetation in crops that have tolerance to agronomic stress (including, but not limited to drought, cold, heat, salt, water, nutrient, fertilizer, pH), tolerance to plague (including but not limited to insects, fungus and pathogens) and traces of improved harvest (including but not limited to field; protein, carbohydrate, or oil content; plant stature and plant architecture).
[000134] The compositions and methods provided here are used to control undesirable vegetation. Undesirable vegetation includes, but is not limited to, the undesirable vegetation that occurs in crops of rice, cereals, wheat, barley, oats, rye, sorghum, maize (maize), sugar cane, sunflower, seed rapeseed, canola, sugar beet, soy, cotton, pineapple, pastures, lawns, natural grazing land, uncultivated land, grass, tree orchards and vines, aquatic, plantation crops, vegetables, industrial vegetation control (IVM) and easements (ROW). [000135] In some embodiments, the methods provided here are used to control undesirable vegetation in rice. In certain
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26/112 modalities, the undesired vegetation is Brachiaria platyphylla (Groseb.) Nash or Urocloa platyphylla (Nash) R.D. Webster (broadleaf brachiaria, BRAPP), Digitaria sanguinalis (L.) Scop. (large mattress grass, DIGSA), species Echinocloa (ECHSS), Echinocloa crus-galli (L.) P. Beauv. (backyard grass, ECHCG), Echinocloa crus-pavonis (Kunth) Schult. (gulf cockspur, ECHCV), Echinocloa colonum (L.) LINK (junglerice, ECHCO), Echinocloa oryzoides (Ard.) Fritsch (early corngrass, ECHOR), Echinocloa oryzicola (Vasinger) Vasinger (late capimilhã, ECHoa), Echinocloa phyllopogon (Stapf) Koso-Pol. (backyard grass, ECHPH), Echinocloa polistachya (Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum Salisb. (saramollagrass, ISCRU), Leptocloa chinensis (L.) Nees (Chinese sprangletop, LEFCH), Leptocloa fascicularis (Lam.) Gray (bearded sprangletop, LEFFA), Leptocloa panicoides (Presl.) Hitchc. (sprangletop from the Amazon, LEFPA), Oryza species (red and harmful rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (fall panicum, PANDI), Paspalum dilatatum Poir. (dallisgrass, PASDI), Rottboellia cochinchinensis (Lour.) W.D. Clayton (camelote grass, ROOEX), Cyperus species (CYPSS), Cyperus difformis L. (smallflower flatsedge, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (yellow sedge, CYPES), Cyperus would L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple tiririca, CYPRO), Cyperus serotinus Rottb./CBClarke (tidalmarsh flatsedge, CYPSE ), Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI), Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb. (Japanese reed, SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus L. Lye (marine clubrush, SCPMA), Schoenoplectus mucronatus L. (rice field reed, SCPMU), Aeschynomene species, (jointvetch, AESSS) , Alternanthera philoxeroides (Mart.) Griseb. (alligator aquatic weed, ALRPH),
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27/112
Alisma plantago-aquatica L. (common plantago, ALSPA), Amaranthus species, (fedegosas and amarantos, AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Commelina benghalensis L. (Benghal dayflower, COMBE), Eclipta alba (L.) Hassk. (America's fake daisy, ECLAL), Heteranthera limosa (SW.) Willd./Vahl (ducksalad, HETLI), Heteranthera reniformis R. & P. (roundleaf mudplantain, HETRE), Ipomoea species (ipomias, IPOSS), Ipomoea hederacea (L.) Jacq. (ivy ipomea, IPOHE), Lindernia dubia (L.) Pennell (false low anagalide, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (southeastern primrose-willow, LUDLI), Ludwigia octovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC), Monochoria korsakowii Regel & Maack (monorail, MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monorail, MOOVA), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Poligonum pensylvanicum L., (Pennsylvania strong herb, POLPY), Poligonum persicaria L. (ladysthumb, POLPE), Poligonum hydropiperoides Michx. (POLHP, soft strong herb), Rotala indica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species, (arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory / Rydb. Ex Hill (hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).
[000136] In some embodiments, the methods provided here are used to control undesirable vegetation in cereals. In certain embodiments, the unwanted vegetation is Alopecurus myosuroides Huds. (black grass, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oats, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Azévem italiano, LOLMU), Phalaris minor Retz. (littleseed birdseed, PHAMI), Poa annua L. (annual grass, POANN), Setaria pumila (Poir.) Roemer & JA Schultes (yellow foxtail, SETLU), Setaria viridis (L.) Beauv . (green foxtail, SETVI), Amaranthus retroflexus L. (fedegosa de
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28/112 red root, AMARE), Brassica species (BRSSS), Chenopodium album L. (common anserine, CHEAL), Cirsium arvense (L.) Scop. (Canadian thistle, CIRAR /, Galium aparine L. (catchweed bedstraw, GALAP), Kochia scoparia (L.) Schrad. (Kochia, KCHSC), Lamium purpureum L. (purple deadnettle, LAMPU), Matricaria recutita L. (chamomile Silvestre, MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed, MATMT), Papaver rhoeas L. (common poppy, PAPRH), Poligonum convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), species of Sinapis (SINSS), Sinapis arvensis L. (wild mustard, SINAR), Stellaria media (L.) Vill. (Common finch, STEME), Veronica persica Poir. (Veronica of Persia, VERPE ), Viola arvensis Murr. (Field violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR).
[000137] In some modalities, the methods provided here are used to control undesirable vegetation in the range and pasture, land without cultivation, IVM and ROW. In certain modalities, the undesired vegetation is Ambrosia artemisiifolia L. (common tasna, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct. non Lam. (spotted cornflower, CENMA), Cirsium arvense (L.) Scop. (Canadian thistle, CIRAR), Convolvulus arvensis L. (field climbing, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L. (leafy euphobia, EPHES), Lactuca serriola L./Torn. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhorn plantain, PLALA), Rumex obtusifolius L. (broad leaf dock, RUMOB), Sida spinosa L. (prickly aids, SIDSP), Sinapis arvensis L. (wild mustard, SINAR ), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidago species (goldenrod, SOOSS), Taraxacum officinale GH Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).
[000138] In some embodiments, the methods provided here are
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29/112 used to control undesirable vegetation found in row, tree and vine crops, and perennial crops. In certain embodiments, the unwanted vegetation is Alopecurus myosuroides Huds. (black grass, ALOMY), Avena fatua L. (wild oats, AVEFA), Brachiaria decumbens Stapf. or Urocloa decumbens (Stapf) R.D. Webster (Suriname grass, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Urocloa brizantha (Hochst. ex A. Rich.) RD (grass beard, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urocloa platyphylla (Nash) RD Webster (broadleaf brachiaria, BRAPP), Brachiaria plantaginea (Link) Hitchc . or Urocloa plantaginea (Link) R.D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (southern sandbur, CENEC), Digitaria horizontalis Willd. (Mattress grass from Jamaica, DIGHO), Digitaria insularis (L.) Mez ex Ekman (bitter grass, TRCIN), Digitaria sanguinalis (L.) Scop. (large mattress grass, DIGSA), Echinocloa crus-galli (L.) P. Beauv. (backyard grass, ECHCG), Echinocloa colonum (L.) Link (junglerice, ECHCO), Eleusine indica (L.) Gaertn. (goosegrass, ELEIN), Lolium multiflorum Lam. (Italian Azévem, LOLMU), Panicum dichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L. (prose wild corn, PANMI), Setaria faberi Herrm. (giant foxtail, SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum halepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellow sedge, CYPES), Cyperus rotundus L. (purple sedge, CYPRO), Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus species (fedegosa and amaranth, AMASS), Ambrosia artemisiifolia L. (common tasna, AMBEL), Ambrosia psilostachya DC. (western Santiago grass, AMBPS), Ambrosia trifida L. (giant Santiago grass, AMBTR), Anoda cristata (L.) Schlecht. (stimulated anoda, ANVCR), Asclepias syriaca L. (common milkweed, ASCSY), Bidens pilosa L. (picão
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30/112 black hairy, BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (broadleaf weed bud, BOILF), Spermacose latifolia (broadleaf weed bud, BOILF), Chenopodium album L. (common anserine, CHEAL), Cirsium arvense (L.) Scop. (Canadian thistle, CIRAR), Commelina benghalensis L. (tropical traperaba, COMBE), Datura stramonium L. (datura, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (calla lily) wildflower, EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden euphorbia, EPHHI), Euphorbia dentata Michx. (toothed euphorbia, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy pulicaria, ERIBO), Erigeron canadensis L. or Conyza canadensis (L.) Cronq. (Canadian pulicaria, ERICA), Conyza sumatrensis (Retz.) E. H. Walker (high pulicaria, ERIFL), Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (small flowered morning glory, IAQTA), Ipomoea hederacea (L.) Jacq. (ipomeia ivy, IPOHE), Ipomoea lacunosa L. (white ipomea, 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. (prickly sida, SIDSP), Sinapis arvensis L (wild mustard, SINAR), Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), Tridax procumbens L. (coat buttons, TRQPR), or Xanthium strumarium L. (common thistle, XANST).
[000139] In some embodiments, the methods provided here are used to control unwanted grass vegetation. In certain modalities, the undesired vegetation is Bellis perennis L. (English daisy, BELPE), Cyperus esculentus L. (yellow tiririca, CYPES), species of Cyperus (CYPSS), Digitaria sanguinalis (L.) Scop. (big grass, DIGSA), Diodia virginiana L. (Vírginia weed bud, DIQVI), Euphorbia species (euphorbia, EPHSS), Glechoma
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31/112 hederacea L. (ground ivy, GLEHE), Hidrocotyle umbellata L. (weed dollar, HIDUM), Kyllinga species (kyllinga, KYLSS), Lamium amplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L. ) Brenan (doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L. (broad leaf plantain, PLAMA), Plantago lanceolata L. (buckhorn / narrow leaf plantain, PLALA), Phyllanthus urinaria L. (chamberbitter , PYLTE), Rumex obtusifolius L. (broad leaf dock, RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Viola species (Wild violet, VIOSS).
[000140] In some embodiments, the compositions and methods provided here are used to control undesirable vegetation consisting of grass, peppermint weeds and broadleaf. In certain embodiments, the compositions and methods provided here are used to control grass, ciperacea and undesirable broadleaf including, but not limited to Brassica, Brachiaria or Urocloa, Bolboschoenus, Cyperus, Digitaria, Echinocloa, Fimbristylis, Ipomoea, Ischaemum, Leptocloa , Papaver, Setaria or Xanthium.
[000141] In some embodiments, the combination of compound (I) or ester or agriculturally acceptable salt thereof and a protoporphyrinogen oxidase inhibitor are used to control, including, but not limited to, rape seed (Brassica napus L.), grass - large mattress (Digitaria sanguinalis), backyard grass (Echinocloa crus-galli), jungle rice (Echinocloa colona), early milan grass (Echinocloa oryzoides), morning glory ivy (Ipomoea hederacea), Chinese sprangletop (Leptocloa chinensis), smallflower umbrella sedge (Cyperus difformis), yellow sedge (Cyperus esculentus), rice flatsedge (Cyperus vai), purple sedge (Cyperus rotundus), globe fringerush (Fimbristylis
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32/112 miliacea), Japanese bulrush (Schoenoplectus juncoides), sea clubrush (Bolboschoenus maritimus or Schoenoplectus maritimus), broadleaf brachiaria (Brachiaria platyphylla or Urocloa platyphylla), saramollagrass (Ischaemum rugosum-raposa-rapisum-salis-rapisum-salisum-rapisum-salisum-rapisum-salisum-rapisum-salisum-rapisum). Setaria viridis), common poppy (Papaver rhoeas), or common thistle (Xanthium strumarium).
[000142] The compounds of Formula I or ester or agriculturally acceptable salt thereof can be used to control herbicide resistant or tolerant weeds. The methods employing the combination of a Formula I compound or ester or agriculturally acceptable salt thereof and the compositions described here can also be employed to control herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, biotype resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (eg, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulphonylaminylaminones) photosystem II inhibitors (eg, phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) s inhibitors (eg, aryloxyphenyloxypropionates, hexylphenyloxypropionates) , synthetic auxins (for example, benzoic acids, phenoxycarboxylic acids, pyridine carboxylic acids, quinoline carboxylic acids), auxin transport inhibitors (eg phthalates, semicarbazones), photosystem inhibitor (eg bipyridyl), inhibitors 5-enolpyruvylchiquimate-3-phosphate (EPSP) synthase (eg glyph sato), glutamine synthetase inhibitors (eg, glufosinate, bialafos), microtubule assembly inhibitors (eg, benzamides, benzoic acids, dinitroanilines,
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33/112 phosphoramidates, pyridines), mitosis inhibitors (eg carbamates), very long chain fatty acid inhibitors (VLCFA) (eg acetamides, chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipid synthesis inhibitors (for example, phosphorodithioates, thiocarbamates, benzofurans, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibitors (for example, diphenylethers, N-phenylphthalimides, oxadiazoles, oxazolidinadiones, phenylpyrazoles, pyrimidindiones, thiadiazides, thiadiazides, thiadiazides, eg clomazone, amitrole, aclonifen), phytene desaturase (PDS) inhibitors (eg, amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxigenase (HPPD) (by callistemones, isoxazoles, pyrazoles, tricetones), cellulosic biosynthesis inhibitors (eg nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple multiple modes of action such as quinclorac, and herbicides not classified as arylaminopropionic, difenzoquat, endotall, and organoarsenic acids. Exemplary resistant or tolerant weeds include, but are not limited to biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes, biotypes with resistance or tolerance to multiple modes of action of the herbicide, and biotypes with multiple mechanisms resistance or tolerance (for example, resistance to the target site or metabolic resistance).
[000143] 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 acifluorphene. With respect to compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to acifluorphene or an agriculturally acceptable salt thereof is in the range of about 1: 210 to about 9: 1 . In
Petition 870200027098, of 02/28/2020, p. 12/36
In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to acifluorphene is in the range of about 1: 191 to about 2: 1. In certain embodiments, the compositions comprise the compound of Formula (I) or its benzyl or n-butyl ester and sodium acifluorphene. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and acifluorphene, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to acifluorphene is from about 1: 17.5 to about 1 : 35. With respect to the methods, in certain modalities, the methods comprise contacting the unwanted or local vegetation of the same or applying to the soil or water, to prevent the appearance or growth of vegetation, a composition described here. In some embodiments, the composition is applied at an application rate of about 37 grams of active ingredient per hectare (g ai / ha) to about 720 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 38 g ai / ha to about 470 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods comprise contacting the unwanted or local vegetation of the same or applying to the soil or water, to prevent the appearance or growth of vegetation, with a compound of Formula (I) or salt or ester thereof and acifluorfen, for example , sequentially or simultaneously. In some embodiments, acifluorphene is applied at a rate of about 35 g ai / ha to about 420 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about from 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In certain embodiments, the methods use the compound of Formula (I) or its benzyl or n-butyl ester and sodium acifluorphene. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and acifluorphene, where the benzyl ester of the
Petition 870200027098, of 02/28/2020, p. 37/125
35/112 compound of Formula (I) is applied at a rate of about 8 g of acid equivalents per hectare (g of ae / ha), and acifluorphene is applied at a rate of about 140 g of ai / ha a about 280 g ai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with acifluorphene are used to control ECHCO.
[000144] 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 azafenidene. In some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to azafeniden is in the range of about 1: 220 to about 10: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to azafeniden is in the range of about 1: 109 to about 2: 1. In certain embodiments, the compositions comprise the compound of Formula (I) or its benzyl or n-butyl ester and azafenidene. With respect to the methods, in certain modalities, the methods comprise contacting the unwanted or local vegetation of the same or applying to the soil or water, to prevent the appearance or growth of vegetation, a composition described here. In some embodiments, the composition is applied at an application rate of about 32 grams of active ingredient per hectare (g ai / ha) to about 540 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 33 g ai / ha to about 290 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods comprise contacting the unwanted or local vegetation of the same or applying to the soil or water, to prevent the appearance or growth of vegetation, with a compound of Formula (I) or salt or ester thereof and azafenidene, for example , sequentially or simultaneously. In some modalities, the
Petition 870200027098, of 02/28/2020, p. 38/125
36/112 azafenidene is applied at a rate of about 30 g ai / ha to about 240 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In certain embodiments, the methods use the compound of Formula (I) or its benzyl or n-butyl ester and azafeniden.
[000145] 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 bifenox. With respect to compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to bifenox is in the range of about 1: 500 to about 3: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to bifenox is in the range of about 1: 455 to about 1: 2.5. In certain embodiments, the compositions comprise the compound of Formula (I) or its benzyl or n-butyl ester and biphenox. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and biphenox, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to bifenox is from about 1: 5 to about 1 : 90. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and biphenox, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to biphenox is from about 1: 9 to about 1 : 90. With respect to the methods, in certain modalities, the methods comprise contacting the unwanted or local vegetation of the same or applying to the soil or water, to prevent the appearance or growth of vegetation, a composition described here. In some embodiments, the composition is applied at an application rate of about 127 grams of active ingredient per hectare (g ai / ha) to about 1300 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate
Petition 870200027098, of 02/28/2020, p. 39/125
37/112 from about 128 g ai / ha to about 1050 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods comprise contacting the unwanted or local vegetation of the same or applying to the soil or water, to prevent the appearance or growth of vegetation, with a compound of Formula (I) or salt or ester thereof and bifenox, for example , sequentially or simultaneously. In some embodiments, bifenox is applied at a rate of about 125 g ai / ha to about 1000 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about from 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In certain embodiments, the methods use the compound of Formula (I) or its benzyl or n-butyl ester and biphenox. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and biphenox, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 8 g of acid equivalents per hectare (g ae / ha) to about 32 g ae / ha, and bifenox is applied at a rate of about 180 g ai / ha to about 720 g ai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and bifenox, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 96 g of acid equivalents per hectare (g of ae / ha), and bifenox is applied at a rate of about 180 g ai / ha to about 720 g ai / ha. In certain embodiments, the methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with bifenox are used to control BRSNW, CYPIR, ECHOR, IPOHE, PAPRH, or SCPMA.
[000146] 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 carfentrazone-ethyl or salt or ester thereof. With respect to the compositions, in some modalities, the
Petition 870200027098, of 02/28/2020, p. 40/125
38/112 weight ratio of the compound of Formula (I) or salt or ester thereof to carfentrazone-ethyl or carboxylic acid or carboxylate salt of the same or another ester is in the range of about 1:60 to about 86: 1 . In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to carfentrazone-ethyl or carboxylic acid or carboxylate salt of the same or another ester is in the range of about 1:49 to about 49 :1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to carfentrazonaethyl or carboxylic acid or carboxylate salt of the same or other ester is in the range of about 1: 0.2 to about 1 : 10. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to carfentrazone-ethyl or carboxylic acid or carboxylate salt of the same or other ester is in the range of about 1: 0.4 to about of 1: 5. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl or n-butyl ester and carfentrazonaethyl. In one embodiment, the composition comprises the compound of Formula (I) and carfentrazone-ethyl, wherein the weight ratio of the compound of Formula (I) to carfentrazone-ethyl is from about 1: 0.4 to about 1: 5. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and carfentrazone-ethyl, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to carfentrazone-ethyl is about 1: 0 , 4 to about 1: 3.2. In one embodiment, the composition comprises the n-butyl ester of the compound of Formula (I) and carfentrazone-ethyl, wherein the weight ratio of the n-butyl ester of the compound of Formula (I) to carfentrazone-ethyl is about 1: 1.75. With respect to the methods, in certain modalities, the methods comprise contacting the unwanted or local vegetation of the same or applying to the soil or water, to prevent the appearance or growth of vegetation, a composition described here. The application rate will depend on the particular type of weed to be controlled, the degree of
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39/112 control required, and the timing and method of application. In some embodiments, the composition is applied at an application rate of about 5.5 grams of active ingredient per hectare (g ai / ha) to about 420 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 8 g ai / ha to about 257 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods comprise contacting the unwanted vegetation or local of the same or applying to the soil or water, to prevent the appearance or growth of vegetation, with a compound of Formula (I) or salt or ester thereof and carfentrazonaethyl or carboxylic acid or carboxylate salt of the same or another ester, for example, sequentially or simultaneously. In some embodiments, the carfentrazone-ethyl or carboxylic acid or carboxylate salt of the same or another ester is applied at a rate of about 3.5 g ai / ha to about 120 g ai / ha and the compound of Formula (I) salt or ester thereof is applied at a rate of about 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In some embodiments, carfentrazone-ethyl or carboxylic acid or carboxylate salt of the same or another ester is applied at a rate of about 3 g ai / ha to about 430 g ai / ha and the compound of Formula (I ) of salt or ester thereof is applied at a rate of about 2 g of acid equivalents per hectare (g of ae / ha) to about 84 g of ae / ha. In some embodiments, the carfentrazonaethyl or carboxylic acid or carboxylate salt of the same or another ester is applied at a rate of about 7 g ai / ha to about 215 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about 4.38 g of acid equivalents per hectare (g of ae / ha) to about 42.4 g of ae / ha. In certain embodiments, the methods use the compound of Formula (I), or its benzyl or n-butyl
Petition 870200027098, of 02/28/2020, p. 42/125
40/112 ester and carfentrazone-ethyl. In one embodiment, the methods use the compound of Formula (I) and carfentrazone-ethyl, in which the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalents per hectare (g of ae / ha) at about 42.4 g ae / ha, and carfentrazone-ethyl is applied at a rate of about 7 g ai / ha to about 215 g ai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and carfentrazone-ethyl, where the benzyl ester of the compound of Formula (I) is applied at a rate of about 8.75 g of acid equivalents per hectare (g of ae / ha) to about 35 g of ae / ha, and carfentrazone-ethyl is applied at a rate of about 3.5 g ai / ha to about 28 g ai / ha. In one embodiment, the methods use the n-butyl ester of the compound of Formula (I) and carfentrazone-ethyl, in which the n-butyl ester of the compound of Formula (I) is applied at a rate of about 16 g of equivalents acid per hectare (g of ae / ha), and carfentrazone-ethyl is applied at a rate of about 28 g ai / ha. In certain embodiments, the methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with carfentrazone-ethyl or carboxylic acid or carboxylate salt of the same or another ester are used to control CYPES, CYPIR, DIGSA, ECHCG, ECHOR or LEFCH.
[000147] 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 flumioxazin. With respect to compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to flumioxazin is in the range of about 1: 300 to about 17: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to flumioxazin is in the range of about 1: 272 to about 3: 1. In certain embodiments, the compositions comprise the compound of Formula (I) or its benzyl or n-butyl ester and flumioxazin. In a
Petition 870200027098, of 02/28/2020, p. 43/125
In this embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and flumioxazin, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to flumioxazin is from about 1: 9 to about 1 : 35. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and flumioxazin, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to flumioxazin is from about 1: 3 to about 1: 27. With respect to the methods, in certain modalities, the methods comprise contacting the unwanted or local vegetation of the same or applying to the soil or water, to prevent the appearance or growth of vegetation, a composition described here. In some embodiments, the composition is applied at an application rate of about 19 grams of active ingredient per hectare (g ai / ha) to about 900 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 20 g ai / ha to about 650 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods comprise contacting the unwanted or local vegetation of the same or applying to the soil or water, to prevent the appearance or growth of vegetation, with a compound of Formula (I) or salt or ester thereof and flumioxazin, for example , sequentially or simultaneously. In some embodiments, flumioxazin is applied at a rate of about 17.5 g ai / ha to about 600 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate from about 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In certain embodiments, the methods use the compound of Formula (I) or its benzyl or n-butyl ester and flumioxazine. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and flumioxazin, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 8 g of acid equivalents per
Petition 870200027098, of 02/28/2020, p. 44/125
42/112 hectare (g of ae / ha) at about 16 g of ai / ha, and flumioxazin is applied at a rate of about 140 g of ai / ha to about 280 g of ai / ha. In one embodiment, the methods use the benzyl ester of the compound of Formula (I) and flumioxazin, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 16 g of acid equivalents per hectare (g ae / ha) to about 32 g ae / ha, and bifenox is applied at a rate of about 105 g ai / ha to about 420 g ai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with flumioxazin are used to control ECHCO, IPOHE, SETVI, or XANST.
[000148] 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 ipfencarbazone. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to ipfencarbazone is in the range of about 1: 250 to about 5: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to ipfencarbazone is in the range of about 1: 227 to about 1: 1. In certain embodiments, the compositions comprise the compound of Formula (I) or its benzyl or n-butyl ester and ipfencarbazone. With respect to the methods, in certain modalities, the methods comprise contacting the unwanted or local vegetation of the same or applying to the soil or water, to prevent the appearance or growth of vegetation, a composition described here. In some embodiments, the composition is applied at an application rate of about 65 grams of active ingredient per hectare (g ai / ha) to about 800 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 66 g ai / ha to about 550 g ai / ha
Petition 870200027098, of 02/28/2020, p. 45/125
43/112 based on the total amount of active ingredients in the composition. In some modalities, the methods comprise contacting the unwanted or local vegetation of the same or applying to the soil or water, to prevent the appearance or growth of vegetation, with a compound of Formula (I) or salt or ester thereof and ipfencarbazone, for example , sequentially or simultaneously. In some embodiments, ipfencarbazone is applied at a rate of about 62.5 g ai / ha to about 500 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate from about 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In certain embodiments, the methods use the compound of Formula (I) or its benzyl or n-butyl ester and ipfencarbazone.
[000149] 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 oxadiargyl. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to oxadiargyl is in the range of about 1: 1100 to about 6: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to oxadiargyl is in the range of about 1: 509 to about 4: 1. In certain embodiments, the compositions comprise the compound of Formula (I) or its benzyl or n-butyl ester and oxadiargyl. In one embodiment, the composition comprises the compound of Formula (I) and oxadiargyl, wherein the weight ratio of the compound of Formula (I) to oxadiargyl is from about 1: 3 to about 1:11. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and oxadiargyl, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to oxadiargyl is from about 1: 5 to about 1 : 11. With respect to the methods, in certain modalities, the methods include contacting the unwanted vegetation or the location of it or applying to the soil or water
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44/112 to prevent the appearance or growth of vegetation a composition described here. In some embodiments, the composition is applied at an application rate of about 15 grams of active ingredient per hectare (g ai / ha) to about 2500 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 16 g ai / ha to about 1170 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods comprise contacting the unwanted vegetation or the location of the same or applying to the soil or water to prevent the appearance or growth of vegetation with a compound of Formula (I) or salt or ester thereof and oxadiargila, for example, sequentially or simultaneously. In some embodiments, oxadiargyl is applied at a rate of about 50 g ai / ha to about 2200 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about from 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In certain embodiments, the embodiments use the compound of Formula (I) or its benzyl or n-butyl ester and oxadiargyl. In one embodiment, the modalities use the compound of Formula (I) and oxadiargyl, in which the compound of Formula (I) is applied at a rate of about 4.38 g of equivalent acid per hectare (g of ae / ha ) at about 17.5 g ae / ha, and oxadiargyl is applied at a rate of about 50 g ae / ha. In one embodiment, the modalities use the benzyl ester of the compound of Formula (I) and oxadiargyl, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare (g of ae / ha) to about 8.75 g of ae / ha, and oxadiargyl is applied at a rate of about 50 g of ai / ha. In certain embodiments, the methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with
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45/112 oxadiargyl are used to control IPOHE.
[000150] 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 oxadiazone. With respect to compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to oxadiazone is in the range of about 1: 2240 to about 10: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to oxadiazone is in the range of about 1:57 to about 2: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to oxadiazone is in the range of about 1: 0.9 to about 1:57. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to oxadiazone is in the range of about 1: 1.8 to about 1: 28.5. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl or n-butyl ester and oxadiazone. In one embodiment, the composition comprises the compound of Formula (I) and oxadiazone, wherein the weight ratio of the compound of Formula (I) to oxadiazone is from about 1: 1.8 to about 1:14, 3. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and oxadiazone, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to oxadiazone is about 1: 1.8 to about 1:70. In one embodiment, the composition comprises the n-butyl ester of the compound of Formula (I) and oxadiazone, wherein the weight ratio of the n-butyl ester of the compound of Formula (I) to oxadiazone is about 1: 3.6 to about 1: 14.3. With respect to the methods, in certain modalities, the methods comprise contacting the unwanted vegetation or the location thereof or applying to the soil or water to prevent the appearance or growth of vegetation a composition described here. In some embodiments, the composition is applied at an application rate of around 33
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46/112 grams of active ingredient per hectare (g ai / ha) to about 4780 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 35 g ai / ha to about 320 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the unwanted vegetation or the location thereof or applying to soil or water to prevent the appearance or growth of vegetation with a compound of Formula (I) or salt or ester thereof and oxadiazone, for example, sequentially or simultaneously. In some embodiments, oxadiazone is applied at a rate of about 31 g ai / ha to about 4480 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about from 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In some embodiments, oxadiazone is applied at a rate of about 15 g ai / ha to about 500 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about from 2 g of acid equivalent per hectare (g of ae / ha) to about 140 g of ae / ha. In some embodiments, oxadiazone is applied at a rate of about 31 g ai / ha to about 250 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about from 4.38 g of acid equivalent per hectare (g of ae / ha) to about 70 g of ae / ha. In certain embodiments, the embodiments use the compound of Formula (I), or its benzyl or n-butyl ester and oxadiazone. In one embodiment, the modalities use the compound of Formula (I) and oxadiazone, in which the compound of Formula (I) is applied at a rate of about 8.75 g of acid equivalents per hectare (g of ae / ha ) at about 35 g ae / ha, and oxadiazone is applied at a rate of about 31 g ai / ha to about 250 g ai / ha. In one embodiment, the modalities use the benzyl ester of the compound of
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47/112
Formula (I) and oxadiazone, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalents per hectare (g of ae / ha) to about 17.5 g of ae / ha, and oxadiazone is applied at a rate of about 31 g ai / ha to about 250 g ai / ha. In one embodiment, the embodiments use the nbutyl ester of the compound of Formula (I) and oxadiazone, in which the n-butyl ester of the compound of Formula (I) is applied at a rate of about 17.5 g of acid equivalents per hectare (g of ae / ha) to about 70 g of ae / ha, and oxadiazone is applied at a rate of about 250 g of ai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with oxadiazone are used to control ECHOR or IPOHE.
[000151] 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 oxyfluorfen. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to oxyfluorfen is in the range of about 1: 1120 to about 3: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to oxyfluorfen is within the range of 1:82 to about 1: 2. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to oxyfluorfen is in the range of about 1: 2 to about 1: 164. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to oxyfluorfen is in the range of about 1: 4.2 to about 1:82. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl or n-butyl ester and oxyfluorfen. In one embodiment, the composition comprises the compound of Formula (I) and oxyfluorfen, wherein the weight ratio of the compound of Formula (I) to oxyfluorfen is from about 1: 4.2 to about 1:68. In one embodiment, the composition comprises the benzyl ester of
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48/112 compound of Formula (I) and oxyfluorfen, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to oxyfluorfen is from about 1: 5 to about 1:82. With respect to the methods, in certain modalities, the methods comprise contacting the unwanted vegetation or the location thereof or applying to the soil or water to prevent the appearance or growth of vegetation a composition described here. In some embodiments, the composition is applied at an application rate of about 92 grams of active ingredient per hectare (g ai / ha) to about 2540 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 94 g ai / ha to about 402 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the unwanted vegetation or the location thereof or applying to soil or water to prevent the appearance or growth of vegetation with a compound of Formula (I) or salt or ester thereof and oxyfluorfen, for example, sequentially or simultaneously. In some embodiments, oxyfluorfen is applied at a rate of about 100 g ai / ha to about 2240 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about from 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In some embodiments, oxyfluorfen is applied at a rate of about 45 g ai / ha to about 720 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about from 2 g of acid equivalent per hectare (g of ae / ha) to about 85 g of ae / ha. In some embodiments, oxyfluorfen is applied at a rate of about 90 g ai / ha to about 360 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about from 4.38 g of acid equivalent per hectare (g of ae / ha) to about 42.4 g of ae / ha. In certain modalities, the modalities use the
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49/112 compound of Formula (I), or its benzyl or n-butyl ester and oxyfluorfen. In one embodiment, the modalities use the compound of Formula (I) and oxyfluorfen, where the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare (g of ae / ha) at about 64 g ae / ha, and oxyfluorfen is applied at a rate of about 90 g ai / ha to about 360 g ai / ha. In one embodiment, the modalities use the benzyl ester of the compound of Formula (I) and oxyfluorfen, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare ( g of ae / ha) to about 32 g of ae / ha, and oxyfluorfen is applied at a rate of about 90 g ai / ha to about 360 g ai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with oxyfluorfen are used to control CYPIR, CYPRO, DIGSA, ECHCG, ECHCO, IPOHE, or SCPJU.
[000152] 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 pentoxazone or salt thereof. With respect to compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to pentoxazone is in the range of about 1: 225 to about 6: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to pentoxazone is within the range of 1:26 to about 1: 2. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to pentoxazone is in the range of about 1: 0.8 to about 1:52. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to pentoxazone is in the range of about 1: 1.6 to about 1:26. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl ester and pentoxazone. In one modality, the
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The 50/112 composition comprises the compound of Formula (I) and pentoxazone, wherein the weight ratio of the compound of Formula (I) to pentoxazone is from about 1: 1.6 to about 1:13. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and pentoxazone, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to pentoxazone is from about 1: 6 to about 1: 26. With respect to the methods, in certain modalities, the methods comprise contacting the unwanted vegetation or the location thereof or applying to the soil or water to prevent the appearance or growth of vegetation a composition described here. In some embodiments, the composition is applied at an application rate of about 58 grams of active ingredient per hectare (g ai / ha) to about 750 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 61 g ai / ha) to about 148 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the unwanted vegetation or the location thereof or applying to soil or water to prevent the appearance or growth of vegetation with a compound of Formula (I) or salt or ester thereof and pentoxazone, for example, sequentially or simultaneously. In some embodiments, pentoxazone is applied at a rate of about 56 g ai / ha to about 450 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about from 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In some embodiments, pentoxazone is applied at a rate of about 25 g ai / ha to about 230 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about from 2 g of acid equivalent per hectare (g of ae / ha) to about 70 g of ae / ha. In some embodiments, pentoxazone is applied at a rate of about
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51/112 from 56 g ai / ha to about 112 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about 4.38 g of acid equivalent per hectare (g of ae / ha) to about 35 g of ae / ha. In certain embodiments, the modalities use the compound of Formula (I), or its benzyl ester and pentoxazone. In one embodiment, the modalities use the compound of Formula (I) and pentoxazone, where the compound of Formula (I) is applied at a rate of about 8.75 g of acid equivalent per hectare (g of ae / ha) at about 35 g ae / ha, and pentoxazone is applied at a rate of about 56 g ai / ha to about 113 g ai / ha. In one embodiment, the modalities use the benzyl ester of the compound of Formula (I) and pentoxazone, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare ( g of ae / ha) to about 8.75 g of ae / ha, and pentoxazone is applied at a rate of about 56 g ai / ha to about 113 g ai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with pentoxazone are used to control CYPRO, ECHCG, FIMMI or SCPJU.
[000153] 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 pyraclonil or salt thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to pyraclonil or salt thereof is in the range of about 1: 180 to about 9: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to pyraclonil or salt thereof is in the range of about 1:62 to about 1: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to pyraclonil or salt thereof is in the range of about 1: 4.4 to about 2: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or
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52/112 ester thereof for pyraclonil or salt thereof is in the range of about 1:34 to about 2: 1. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl or n-butyl ester and pyraclonyl. In one embodiment, the composition comprises the compound of Formula (I) and pyraclonyl, wherein the weight ratio of the compound of Formula (I) to pyraclonil is about 1:31 to about 1: 3. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and pyraclonyl, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to pyraclonil is from about 1: 2 to about 1:34. With respect to the methods, in certain modalities, the methods comprise contacting the unwanted vegetation or the location thereof or applying to the soil or water to prevent the appearance or growth of vegetation a composition described here. In some embodiments, the composition is applied at an application rate of about 36 grams of active ingredient per hectare (g ai / ha) to about 660 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 41 g ai / ha to about 305 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods include contacting the unwanted vegetation or the location of the same or applying to the soil or water to prevent the appearance or growth of vegetation with a compound of Formula (I) or salt or ester thereof and pyraclonil or salt thereof , for example, sequentially or simultaneously. In some embodiments, piraclonil is applied at a rate of about 34 g ai / ha to about 360 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about from 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In some embodiments, pyraclonil or its salt is applied at a rate of
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53/112 about 4 g ai / ha to about 140 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about 2 g of acid equivalent per hectare ( g of ae / ha) to about 45 g of ae / ha. In some embodiments, pyraclonil or salt thereof is applied at a rate of about 33.75 g ai / ha to about 270 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about 4.38 g of acid equivalents per hectare (g of ae / ha) to about 35 g of ae / ha. In certain embodiments, the embodiments use the compound of Formula (I), or its benzyl or n-butyl ester and pyraclonyl. In one embodiment, the modalities use the compound of Formula (I) and pyraclonyl, where the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare (g of ae / ha ) at about 35 g ae / ha, and pyraclonil is applied at a rate of about 33.75 g ai / ha to about 270 g ai / ha. In one embodiment, the modalities use the benzyl ester of the compound of Formula (I) and pyraclonyl, in which the benzyl ester of the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare (g of ae / ha) to about 35 g of ae / ha, and pyraclonil is applied at a rate of about 33.75 g ai / ha to about 270 g ai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with pyraclonil are used to control BRAPP, CYPRO, ECHCG, ECHCO, ECHOR IPOHE or ISCRU.
[000154] 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 piraflufen-ethyl 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 piraflufen-ethyl or carboxylic acid or carboxylate salt of the same or another ester is in the range of about
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54/112
1: 6 to about 150: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to piraflufen-ethyl or carboxylic acid or carboxylate salt of the same or other ester is in the range of about 1: 5.5 to about 25: 1. In certain embodiments, the compositions comprise the compound of Formula (I) or its benzyl or n-butyl ester and piraflufen-ethyl. In one embodiment, the composition comprises the benzyl ester of the compound of Formula (I) and piraflufen-ethyl, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to piraflufen-ethyl is about 1: 3 to about 1.5: 1. With respect to the methods, in certain modalities, the methods comprise contacting the unwanted vegetation or the location thereof or applying to the soil or water to prevent the appearance or growth of vegetation a composition described here. In some embodiments, the composition is applied at an application rate of about 4 grams of active ingredient per hectare (g ai / ha) to about 312 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 5 g ai / ha to about 62 g ai / ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the unwanted vegetation or the location of the same or applying to the soil or water to prevent the appearance or growth of vegetation with a compound of Formula (I) or salt or ester thereof and piraflufen-ethyl or acid carboxylic or carboxylate salt of the same or another ester, for example, sequentially or simultaneously. In some embodiments, piraflufen-ethyl or carboxylic acid or carboxylate salt of the same or another ester is applied at a rate of about 2 g ai / ha to about 12 g ai / ha and the compound of Formula (I ) of salt or ester thereof is applied at a rate of about 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In certain modalities, the modalities
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55/112 use the compound of Formula (I) or its benzyl or n-butyl ester and piraflufen-ethyl. In one embodiment, the modalities use the benzyl ester of the compound of Formula (I) and piraflufen-ethyl, where the benzyl ester of the compound of Formula (I) is applied at a rate of about 8 g of acid equivalent per hectare ( g of ae / ha) to about 16 g of ae / ha, and piraflufen-ethyl is applied at a rate of about 2.6 g ai / ha to about 10.6 g ai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with piraflufen-ethyl are used to control CYPIR or ECHCG.
[000155] 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 saflufenacil or salt thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to saflufenacil or salt or ester thereof is in the range of about 1: 100 to about 60: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to saflufenacil or salt or ester thereof is in the range of about 1: 9 to about 12: 1. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to saflufenacil or salt thereof is in the range of about 1: 0.1 to about 1:10. In certain embodiments, the weight ratio of the compound of Formula (I) or salt or ester thereof to saflufenacil or salt thereof is in the range of about 1: 0.3 to about 1: 5. In certain embodiments, the compositions provided herein comprise the compound of Formula (I) or its benzyl or n-butyl ester and saflufenacil. In one embodiment, the composition comprises the compound of Formula (I) and saflufenacil, wherein the weight ratio of the compound of Formula (I) to saflufenacil is from about 1: 0.3 to about 1: 5. In one embodiment, the composition comprises the benzyl ester of the compound of
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56/112
Formula (I) and saflufenacil, wherein the weight ratio of the benzyl ester of the compound of Formula (I) to saflufenacil is from about 1: 0.3 to about 1: 5. In one embodiment, the composition comprises the n-butyl ester of the compound of Formula (I) and saflufenacil, wherein the weight ratio of the n-butyl ester of the compound of Formula (I) to saflufenacil is about 1: 1.1. With respect to the methods, in certain modalities, the methods comprise contacting the unwanted vegetation or the location thereof or applying to the soil or water to prevent the appearance or growth of vegetation a composition described here. In some embodiments, the composition is applied at an application rate of about 7 grams of active ingredient per hectare (g ai / ha) to about 500 g ai / ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of about 9 g ai / ha to about 110 g ai / ha based on the total amount of active ingredients in the composition. In some modalities, the methods include contacting the unwanted vegetation or the location of the same or applying to the soil or water to prevent the appearance or growth of vegetation with a compound of Formula (I) or salt or ester thereof and saflufenacil or salt thereof , for example, sequentially or simultaneously.In some embodiments, saflufenacil or salt or ester thereof is applied at a rate of about 5 g ai / ha to about 200 g ai / ha and the compound of Formula (I ) of salt or ester thereof is applied at a rate of about 2 grams of acid equivalent per hectare (g of ae / ha) to about 300 g of ae / ha. In some embodiments, saflufenacil or salt thereof is applied at a rate of about 2 g ai / ha to about 80 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied in a rate of about 2 g of acid equivalents per hectare (g of ae / ha) to about 140 g of ae / ha. In some modalities, saflufenacil or its salt is applied in
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57/112 a rate of about 5 g ai / ha to about 40 g ai / ha and the compound of Formula (I) of salt or ester thereof is applied at a rate of about 4.38 g of acid equivalents per hectare (g of ae / ha) to about 70 g of ae / ha. In certain embodiments, the modalities use the compound of Formula (I), or its benzyl or n-butyl ester and saflufenacil. In one embodiment, the modalities use the compound of Formula (I) and saflufenacil, in which the compound of Formula (I) is applied at a rate of about 4.38 g of acid equivalent per hectare (g of ae / ha ) at about 70 g ae / ha, and saflufenacil is applied at a rate of about 5 g ai / ha to about 40 g ai / ha. In one embodiment, the modalities use the benzyl ester of the Formula (I) compound and saflufenacil, in which the benzyl ester of the Formula (I) compound is applied at a rate of about 4.38 g of acid equivalent per hectare (g of ae / ha) to about 17.5 g of ae / ha, and saflufenacil is applied at a rate of about 5 g ai / ha to about 20 g ai / ha. In one embodiment, the modalities use the n-butyl ester of the compound of Formula (I) and saflufenacil, in which the n-butyl ester of the compound of Formula (I) is applied at a rate of about 35 g of acid equivalents per hectare (g of ae / ha), and saflufenacil is applied at a rate of about 40 g ai / ha. In certain embodiments, methods and compositions using the compound of Formula (I) or salt or ester thereof in combination with saflufenacil or salt thereof are used to control CYPIR, CYPRO, ECHCG, ECHCO, ECHOR, ISCRU or LEFCH.
[000156] The components of the mixtures described here can be applied separately or as part of a multi-part herbicide system.
[000157] The mixtures described here can be applied with one or more other herbicides to control a wide variety of undesirable vegetation. When used in accordance with other herbicides,
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58/112 the composition can be formulated with another herbicide or herbicides, tank mixed 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; 2,4-D; 2,4-D choline salt, 2,4-D esters and amines, 2,4-DB; 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, aclonifene, acrolein, alachlor, alidochlor, aloxidim, allyl alcohol, alorac, ametridione, ametrine, amibuzine, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralide, amiprofos-methyl, amitrol, ammonium sulfamide, anilone, amylamine, anilone , azimsulfurone, aziprotrin, barban, BCPC, beflubutamide, benazoline, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentiocarb, bentazonsodium, benzadox, benzfendizone, benzipram, benzobicyclone, benzofen, benzofen, benzofen, benzofen , bispiribac-sodium, borax, bromacil, bromobonil, bromobutide, bromophenoxy, bromoxynil, bromopyrazon, butachlor, butafenacil, butamiphos, butenachlor, butidazole, butiuron, butralin, butoxidim, buturonate, butyric acid, chloride, butylate calcium, cambendichlor, carbasulam, carbetamide, carboxazole chlorprocarb, CDEA, CEPC, clomethoxyfen, chlorambene, chloranocril, chlorazifop , chlorazine, chlorobromuron, chlorinamide, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazone, chlorimuron, chlornitrofen, chloropon, chlorotolurone, chloroxuron, chloroxynil, chlorprofam, clorsulfuron, cinternal, chloride, chloride, chloride, chloride , cliodinate, clodinafop-propargyl, clofop, clomazone, clomeprop, cloprop, cloproxidim, clopyralid, chloransulam-methyl, CMA, copper sulphate, CPMF, CPPC, credazine, cresol, cumiluron, cyanatrine, cyanazine, cyclohexate, cyclopyridate, cyclohexyl ,
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59/112 cyclurone, cyhalofop-butyl, cyperquat, cyperazine, cyprazole, cypromide, daimurone, dalapon, dazomet, delaclor, demedifam, desmethrin, dialate, dicamba, diclobenil, dichloralurea, dichlormate, dichloro-dichloro-dichloropropyl, dichloropropyl, dichloropropyl , dietamquat, dietathyl, diphenopentene, diphenoxurone, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimetachlor, dimetamethrin, dimethenamid, dimethenamid-P, dimexane, dimidazon, dinitramine, dinofenate, dinino, dinino, dinoprop , disul, dithiopir, diurone, DMPA, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, sprocarb, etalfluralin, etbenzamide, etametsulfurone, etidimuron, etiolate, etobenzamide, etobenzamide, ethoxide, ethoxy, ethoxy, ethoxy , etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop, fenoxaprop-Petila, fenoxaprop-P-ethyl + isoxadifen-ethyl, phenoxasulfone, fenteracol, fentiaprop, fentrazamide, fenuron, ferrous sulfate, f lamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, flucloralin, flumipropin, fluometuron, fluvordifene, fluorglicofen, flúormid, fluoro fluoro, fluoro fluoro, fluoro fluoro flurochloridone, fluroxypyr, fluroxypyr-meptila, flurtamone, flutiacet, fomesafen, foramsulfuron, phosamine, fumiclorac, furyloxifene, glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosate, halogenated, halogenated, halogenated haloxifop-methyl, haloxifop-P-methyl, hexachloroacetone, hexaflurate, hexazinone, imazametabenz, imazamox, imazapic, imazapyr, imazaquine, imazosulfuron, imazetapyr, indanofan, indaziflamine, iodobonyl, iodobonyl, iodobonyl, iodine ipazine, iprimidam, isocarbamid, isocyl, isomethiozine, isonorurone, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxaclortol, isoxaflutol, isoxapyrifop, carbutylate,
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60/112 cetospiradox, lactofen, lenacil, linuron, MAA, MAMA, MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfurone, mesotrione, metametone, metametone, metamethone, metamethone, metamethone, methamphon, , metazachlor, metazosulfurone, metflurazone, metabenztiazurone, metallol, metazol, methiobencarb, methiozoline, methurone, methometone, methoprotrin, methyl bromide, methyl isothiocyanate, methyldinone, metobenzuron, methromururon, methromururon, methromururon, methromururon, methromuron , molinate, monalide, monisourone, monochloroacetic acid, monolinurone, monurone, morfamquat, MSMA, naproanilide, napropamide, naptalam, neburone, nicosulfurone, nipyraclofen, nitralin, nitrophen, nitrofluorfen, norflurazone, orurone, norurone, norurone, norurone oryzaline, oxaprazone, oxasulfurone, oxaziclomefone, paraflufen-ethyl, paraflurone, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, entachlorophenol, pentanochlor, perfluidone, petoxamide, fenisofam, fenmedifam, fenmedifam-ethyl, phenobenzurone, phenylmercury acetate, picloram, picolinafen, pinoxadene, piperophos, potassium arsenite, potassium azide, priamine potassium, prionyl chloride, potassium chloride prodiamine, profluazole, profluralin, profoxidim, proglinazine, proexadione-calcium, promethazine, promethrin, pronamide, propachlor, propanil, propaquizafop, propazine, profam, propisochlor, propoxycarbazone, propyrisulfurone, propamide, prosulfalin, prosulfan, prosulfocarbon, prosulfocarin, prosulfocarin, pirassulfotol, pyrazogyl, pyrazolinate, pyrazosulfuron-ethyl, pyrazoxifene, piribenzoxim, piributicarb, piriclor, pyridafol, pyridate, pyriftalide, piriminobac, pyrimisulfan, piritiobac-sodium, pyroxsulfone, pyroxsulam quinoxin, quinoquam, quincalac, quincalac, quincalac, quincal, quincal ethyl, rodetanil, rinsulfurone, S-metolachlor, sebutilazine, secbumetone, setoxidim, siduroan, simazine, simethona, symmetry, SMA,
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61/112 sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfalate, sulfentrazone, sulfometurone, sulfosulfuron, sulfuric acid, sulfuric acid, sulglicapine, swep, SYN-523, TCA, tebutam, tebutiuron, tefuriltrione, tembotrim, tebotrim, tebotrim, tebotrim, tebotrim, tebotrim, tebotrim, tebotrim, tebotrion terbacil, terbucarb, terbuclor, terbumeton, terbuthylazine, terbutrin, tetrafluron, tenilchlor, thiazafluron, tiazopir, tidiazimine, tidiazuron, tiencarbazone-methyl, tifensulfuron, tifensulfurn, tifensulfin, trifon, trilone triaziflam, tribenurone, tribenuronmethyl, tricamba, triclopir choline salt, triclopyr esters and salts, tridifan, trietazine, trifloxysulfuron, trifluralin, triflussulfurone, trifop, triphylt, tridroxitriazine, tractron, tracetone, trihydrone optionally active isomers and mixtures thereof.
[000158] The compositions and methods described here, can also be used in conjunction with glyphosate, 5enolpyruvylchiquimate-3-phosphate (EPSP) synthase, glufosinate inhibitors, glutamine synthetase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins , auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonylhydrates and acylsulfone hydrolyses ), 4-hydroxyphenyl-pyruvate dioxigenase (HPPD) inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, fatty acid inhibitors very long chain, fatty acid and lipid biosynthesis inhibitors, i photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil in glyphosate tolerant crops, tolerant
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62/112 to the EPSP synthase inhibitor, tolerant to glufosinate, tolerant to glutamine synthetase inhibitor, tolerant to dicamba, tolerant to phenoxy auxin, tolerant to pyridyloxy auxin, tolerant to auxin, tolerant to auxin transport inhibitor, tolerant to auxin aryloxyphenoxypropionate, tolerant to cyclohexanedione, tolerant to phenylpyrazoline, tolerant to ACCase, tolerant to imidazolinone, tolerant to sulfonylurea, tolerant to pyrimidinylthiobenzoate, tolerant to triazolopyrimidine, tolerant to sulfonylaminocarbonyl-tolerants, ALH-tolerants, ALH-tolerants phytoene desaturase, tolerant to carotenoid biosynthesis inhibitor, tolerant to PPO, tolerant to cellulose biosynthesis inhibitor, mitosis inhibitor, tolerant to microtubule inhibitor, tolerant to very long chain fatty acid inhibitor, tolerant to biosynthesis inhibitor of fatty acid and lipid, tolerant to photo inhibitor system I, tolerant to photosystem inhibitor II, tolerant to triazine, and tolerant to bromoxynil, and crops that have multiple or stacked traits that provide 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 to be treated and that complement the controlled weed spectrum 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 mix, or as a sequential application.
[000159] In some embodiments, the compositions described here are used in combination with one or more herbicidal protectors, such as AD-67 (MON 4660), benoxacor, bentiocarb,
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63/112 brassinolid, cloquintocet (mexil), ciometrinil, daimuron, diclormid, dicyclone, dimepiperate, disulfotone, fenclorazole-ethyl, fenclorim, flurazol, fluxofenim, furilazol, harpine proteins, isoxadifen-ethyl, jieca, jieca mefenate, naphthalic anhydride (NA), oxabetrinyl, R29148 and M-phenylsulfonylbenzoic acid amides, to enhance their selectivity. In some modalities, protectors are used in rice, cereal, corn (corn), or maize (maize) settlements. In some embodiments, the protector is cloquintocet or an ester or salt thereof. In certain embodiments, cloquintocet is used to antagonize the harmful effects of the compositions on rice and cereals. In some embodiments, the protector is cloquintocet (mexil).
[000160] In some embodiments, the compositions described here are used in combination with one or more plant development regulators, such as 2,3,5-triiodiodobenzoic acid, IAA, IBA, naphthalene acetamide, α-naphthalene acetic acids, benzyladenine , 4-hydroxyphenethyl alcohol, kinetin, zeatin, endotal, etefone, pentachlorophenol, thidiazurone, tribufos, aviglycine, gibberellins, gibberellic acid, abscisic acid, ancimidol, phosamine, glyphosine, isopyrimol, jasonic acid, mezateine , 5-triiodobenzoic, morphactins, dichlorflurenol, flurprimidol, mefluidide, paclobutrazol, tetciclacis, uniconazole, brassinolide, brassinolide-ethyl, cycloheximide, ethylene, methasulfocarb, prohexadione, triapentenol and trinexentaphenol and trinexentaphenol
[000161] In some embodiments, plant development regulators are employed in one or more crops or settlements such as rice, cereal crops, maize crops, maize, broadleaf, rapeseed / canola , grass, pineapple, sugar cane, sunflower, grassland, lawns, natural grazing land, uncultivated land, grass, vine trees and orchids, plantation crops, vegetables, and non-settlement
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64/112 harvest (ornamental). In some embodiments, the plant development regulator is mixed with the compound of Formula (I), or mixed with the compound of Formula (I) and a protoporphyrinogen oxidase to cause a preferentially beneficial effect on plants.
[000162] In some embodiments, the compositions provided here also 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 the application of compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients. Such mixtures can be designed for direct application to weeds or local I or can be concentrated or formulations that are normally silenced with vehicle and additional adjuvants before application. They can be solids, such as, for example, powders, granules, granules dispersed in water, or wetting powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be supplied as a premix or tank mix.
[000163] Agriculturally suitable adjuvants and vehicles include, but are not limited to, harvest oil concentrate; nonylphenol ethoxylate; quartzyl ammonium salt of benzylcocoalkylimethyl; mixture of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9-C11 alkyl polyglycoside; phosphate alcohol ethoxylate; (C12-C16) natural primary alcohol ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG (400) dioleate-99.
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[000164] Liquid vehicles that can be used include water and organic solvents. Organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, flax seed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 containing hydroxy), such as 2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; ester of mono-, di- and polycarboxylic acids and the like. Specific organic solvents include, but are not limited to, toluene, xylene, petroleum naphtha, harvest oil, acetone, methyl ethyl ketone, cyclohexanone, trichlorethylene, perchlorethylene, ethyl acetate, amyl acetate, butyl acetate, monomethyl ether propylene glycol and monomethyl ether, diethylene glycol, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerin, M-methyl-2-pyrrolidinone, M, M-dimethyl alkylamides, dimethyl sulfoxide, fertilizers liquids and the like. In certain embodiments, water is the vehicle for diluting concentrates.
[000165] Suitable solid vehicles include, but are not limited to, talc, pyrophyllite clay, silica, atapulgo clay, kaolin clay, diatomite, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller earth, cotton seed husks, wheat flour, soy flour, pumice stone, flour and wood, nutshell flour, lignin, cellulose, and the like.
[000166] In some embodiments, the compositions described here also comprise one or more surfactants. In some
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66/112 modalities, such surfactants are used in both solid and liquid compositions, and in certain modalities those designed to be diluted with the vehicle before application. Surfactants can be anionic, cationic or non-ionic in character and can be used as emulsifying agents, wetting agents, surfactants, or for other purposes. Surfactants that can also be used in the present formulations are described, among other things, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New Jersey, 1998 and in Enciclopedia of Surfactants, Volume I-III, Chemical Publishing Co., New York, 1980-81. Surfactants include, but are not limited to, alkyl sulfate salts, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzonesulfonate; alkylphenolalkylene oxide addition products, such as nonylphenol-Cw ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-Cw ethoxylate; soaps, such as sodium stearate; alkylnaphthalene sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di (2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; blocking copolymers of ethylene oxide and propylene oxide; salts of mono- and dialkyl phosphate esters; seed or vegetable oils such as soybean oil, rapeseed oil / canola oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, oil flax seed, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters from the above vegetable oils, and in certain embodiments, methyl esters.
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[000167] In some embodiments, these materials, such as vegetable or seed oils and their esters, can be used interchangeably interchangeably as an agricultural adjuvant, as a liquid carrier or as a surfactant.
[000168] Other exemplary additives for use in the compositions provided here include, but are not limited to, compatibilizing agents, antifoaming agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, dispersing agents, penetration aids, adhesion agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like. The compositions can also contain other compatible components, for example, other herbicides, plant growth regulators, fungicides, insecticides, and the like and can be formulated with liquid or solid fertilizers, particulate fertilizer vehicles such as ammonium nitrate, urea and the like .
[000169] In some embodiments, the concentration of the active ingredients in the compositions described here is about 0.0005 to 98 weight percent. In some embodiments, the concentration is about 0.0006 to 90 weight percent. In compositions designed to be employed as concentrates, the active ingredients, in certain embodiments, are present in a concentration of about 0.1 to 98 weight percent, and in certain embodiments 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 location of weeds 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.
[000170] The present compositions can be applied to herbs
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68/112 weeds or to their location by the use of aerial sprayers or conventional soil, vaporizers, and granule applicators, by addition to irrigation or flood water, and by other conventional methods known to those skilled in the art.
[000171] The modalities described and the following examples are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses, or combinations with respect to the compositions described here will be evident to a person versed in the technique without departing from the spirit and scope of the claimed object matter.
EXAMPLES
[000172] The results in Examples I, II, III and IV are greenhouse test results.
EXAMPLE I. EVALUATION OF HERBICIDAL MIXTURES FOR POST-EMERGENCY FOLIAR APPLICATION FOR CONTROLLING VANILLA IN DIRECT-SEED RICE
[000173] Seeds or seedlings of the desired test plant species were planted in a prepared soil matrix by mixing a clay soil 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 limestone gravel in a ratio of 80 to 20. The soil matrix was contained in pots plastics with a volume of 1 quarter and a surface area of 83.6 square centimeters (cm ² ). When required to ensure good germination and healthy plants, a fungicide treatment and / or other chemical or physical treatment was applied. The plants were grown for 8 to 22 days in a greenhouse with a photoperiod of approximately 14 hours that was maintained at about 29 ° C during the day and 26 ° C at night. Nutrients (Peters Excel® 15-5-15 5-Ca 2Mg and iron chelate) were applied to the irrigation solution when
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69/112 required and water was added on a regular basis. Supplementary lighting was provided with 1000 Watt metal halide suspended lamps when needed. The plants were used for testing when they reached the first to the fourth stage of real leaf. [000174] The treatments consisted of the amino acid 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 with a SC (suspension concentrate), and various herbicidal components alone and in combination. Compound A forms were applied on an equivalent acid base.
[000175] The forms of compound A (compound of Formula I) tested include:

n-Butyl ester of compound A
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Benzyl ester of compound A
[000176] Other herbicidal components were applied on an active ingredient basis and included protoporphyrinogen oxidase (PPO) inhibiting herbicides, carfentrazone-ethyl formulated as Aim ^® EC, oxyfluorfen formulated as GoalTender ^® SC or technical material, pyraclonil formulated as Piraclon ^® , oxadiazone formulated as Ronstar® 50W, and saflufenacil formulated as Sharpen®, sodium salt of acifluorfen formulated as Blazer, bifenox formulated as Fox or technical grade material, flumioxazin formulated as Payload, and piraflufen-ethyl (technical grade material).
[000177] Treatment requirements were calculated based on the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, and an application volume of 12 mL at a rate of 187 L / ha.
[000178] For treatments comprised of formulated compounds, measured amounts of compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.25% (volume / volume) of concentrated Agri-Dex® harvest oil to obtain 12X of raw material solutions. If a test compound does not dissolve easily, the mixture will be heated and / or sonicated. The application solutions were prepared by adding an appropriate amount of each raw material solution (for example, 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of a 1.25% aqueous mixture (volume / volume) of oil concentrate
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71/112 harvest so that the final spray solutions contained 1.25 + / 0.05% (volume / volume) of harvest oil concentrate.
[000179] For treatments comprising technical compounds, heavy amounts can be placed individually in 25 ml glass vials and dissolved in a volume of 97: 3 per volume / volume of acetone / DMSO to obtain 12X of raw material solutions. If a test compound does not dissolve easily, the mixture can be heated and / or sonicated. Application solutions can be prepared by adding an appropriate amount of each raw material solution (for example, 1 ml) and diluted to the appropriate final concentrations with the addition of 10 ml of a 1.5% aqueous mixture ( volume / volume) of harvest oil concentrate so that the spray solutions contain 1.25% (volume / volume) of harvest oil concentrate. When technical materials are used, concentrated raw material 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.
[000180] For treatments comprised of technical and formulated compounds, heavy amounts of the technical materials were placed individually in 25 mL glass vials and dissolved in a 97: 3 volume / volume of acetone / DMSO to obtain 12X of matter solutions raw materials, and measured quantities of the formulated compounds were placed individually in 25 ml glass vials and diluted in a volume of 1.5% (volume / volume) of harvest oil concentrate or water to obtain 12X of raw material solutions cousin. If a test compound does not dissolve easily, the mixture will be heated and / or sonicated. The application solutions were prepared by adding an appropriate amount of each raw material solution (for example, 1 mL) and diluted to
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72/112 the appropriate final concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (volume / volume) of crop oil concentrate so that the final spray solutions contained 1.25% (volume / volume) of harvest oil concentrate. When required, additional water and / or 97: 3 volume / volume of acetone / DMSO were added to the individual application solutions so that the final concentrations of acetone and DMSO of the application solutions being compared were 8.1% and 0, 25%, respectively.
[000181] All raw material solutions and application solutions were visually inspected for the compatibility of the compound before application. The spray solutions were applied to the plant material with an aerial Mandel trail sprayer equipped with 8002E nozzles calibrated to release 187 L / ha over an application area of 0.503 m ² at a spray height of 46 to 50 cm (18 to 20 inches) above the average plant cover height. The control plants were sprayed in the same way with the virgin solvent.
[000182] The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent the elimination of 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 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete death.
[000183] 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.).
[000184] The following equation was used to calculate the activity
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73/112 expected of mixtures containing two active ingredients, A and B: Expected = A + B - (A x B / 100)
[000185] A = observed effectiveness of active ingredient A in the same concentration as used in the mixture.
[000186] B = observed effectiveness of active ingredient B at the same concentration as used in the mixture.
[000187] The tested compounds, application rates used, plant species tested, and are provided in tables 1 to 21.
TABLE 1. Synergistic activity of Herbicidal Compositions of Carfentrazone-ethyl and Compound A Acid of Foliar Application on the
Weed Control in a Rice Growing System.
Compound A Acid Carfentrazonaetila Visual weed control (%) - 21 DAA DIGSA ECHCG g of ae / ha ai ai / ha Observed Expected Observed Expected 4.38 0 33 - 33 - 8.75 0 40 - 55 - 17.5 0 43 - 93 - 0 14 0 - 10 - 4.38 14 50 33 50 39 8.75 14 35 40 70 60 17.5 14 60 43 95 93 Compound acidTHE Carfentrazone-ethyl Visual weed control (%) -21 DAA CYPES g of ae / ha ai ai / ha Observed Expected 4.38 0 18 - 8.75 0 80 - 0 7 0 - 0 14 0 - 4.38 7 40 18 8.75 7 95 80 4.38 14 50 18 8.75 14 90 80
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Compound A acid Carfentrazone-ethyl Visual weed control (%) -19 DAA LEFCH g of ae / ha ai ai / ha Observed Expected 19.4 0 5 - 0 28 10 - 19.4 28 38 15
TABLE 2. Synergistic activity of Herbicidal Compositions of Carfentrazone-Ethyl and Benzyl Ester of Compound A of Foliar Application on Weed Control in a Rice Cultivation System.
Benzyl ester of compound A Carfentra zona-ethyl Visual weed control (%) - 21 DAA ECHCG CYPIR g of ae / ha ai ai / ha Observed Expected Observed Expected 8.75 0 55 - 85 - 0 3.5 0 - 0 - 0 7 0 - 0 - 0 14 10 - 0 - 8.75 3.5 75 55 100 85 8.75 7 90 55 100 85 8.75 14 80 60 85 85
TABLE 3. Synergistic activity of herbicidal compositions of carfentrazone-ethyl and n-butyl ester of compound A of foliar application on Weed Control in a Rice Cultivation System.
n-Butyl ester ofCompound A Carfentrazonaetil Visual weed control (%) - 19 DAA LEFCH g of ae / ha ai ai / ha Observed Expected 16 0 10 - 0 28 10 - 16 28 35 19 TABLE 4. Synergistic Activity c and Compositions Herbicides
Oxifluorphene (technical) and Foliar A Compound A Acid on Weed Control in a Rice Growing System.
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Compound A acid Oxyfluorfen Visual weed control (%) - 21DAA DIGSA g of ae / ha ai ai / ha Observed Expected 5.3 0 20 - 10.6 0 30 - 21.2 0 35 - 0 90 70 - 0 180 50 - 0 360 85 - 5.3 90 60 76 10.6 90 99 79 21.2 90 99 81 5.3 180 100 60 10.6 180 95 65 21.2 180 100 68 5.3 360 100 88 10.6 360 100 90 21.2 360 100 90
TABLE 5. Synergistic activity of Herbicidal Compositions
Oxifluorphene (technical) and Benzyl Ester of Compound A of Foliar Application on Weed Control in a Rice Cultivation System.
Benzyl ester of compound A Oxyfluorfen Visual weed control (%) -21 DAA DIGSA g of ae / ha ai ai / ha Observed Expected 4.38 0 10 - 8.75 0 45 - 17.5 0 70 - 0 180 50 - 4.38 180 100 55 8.75 180 99 73 17.5 180 95 85
Benzyl ester of compound A Oxyfluorfen Visual weed control (%) -21 DAA CYPIR g of ae / ha ai ai / ha Observed Expected
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4.38 0 30 - 0 90 0 - 0 180 30 - 0 360 40 - 4.38 90 95 30 4.38 180 100 51 4.38 360 100 58
TABLE 6. Synergistic Activity of Herbicidal Compositions
Oxifluorphene (SC) and Foliar Application Compound A Acid on the
Weed Control in a Rice Growing System.
Compound A acid Oxyfluorfen Visual weed control (%) - 23 DAA ECHCG g of ae / ha ai ai / ha Observed Expected 4.38 0 45 - 8.75 0 55 - 17.5 0 80 - 0 180 30 - 4.38 180 80 62 8.75 180 85 69 17.5 180 80 86
Compound A acid Oxyfluorfen Visual weed control (%) - 23 DAA ECHCO g of ae / ha ai ai / ha Observed Expected 4.38 0 15 - 8.75 0 60 - 0 90 50 - 4.38 90 95 58 8.75 90 100 80
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TABLE 7. Synergistic Activity of Herbicidal Compositions of Oxifluorfen (SC) and Benzyl Ester of Compound A of Foliar Application on Weed Control in a Rice Cultivation System.
Benzyl ester of compound A Oxyfluorfen Visual weed control (%) -23 DAA DIGSA g of ae / ha ai ai / ha Observed Expected 4.38 0 0 - 8.75 0 0 - 17.5 0 15 - 0 180 60 - 4.38 180 65 60 8.75 180 100 60 17.5 180 100 66
Benzyl ester of compound A Oxyfluorfen Visual weed control (%) -23 DAA ECHCG g of ae / ha ai ai / ha Observed Expected 4.38 0 40 - 0 90 30 - 0 180 30 - 0 360 95 - 4.38 90 80 58 4.38 180 100 58 4.38 360 100 97
Benzyl ester of compound A Oxyfluorfen Visual weed control (%) -23 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 4.38 0 10 - 8.75 0 10 - 17.5 0 40 - 0 90 85 - 0 180 85 - 4.38 90 100 87 8.75 90 100 87
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17.5 90 100 91 4.38 180 99 87 8.75 180 100 87 17.5 180 100 91
TABLE 8. Synergistic Activity of Herbicidal Compositions
Pyraclonil and Foliar A Compound A Acid on Weed Control in a Rice Cultivation System.
Compound A acid Pyraclonil Visual weed control (%) - 20 DAA BRAPP g of ae / ha ai ai / ha Observed Expected 4.38 0 10 - 0 33.75 0 - 0 67.5 0 - 0 135 0 - 4.38 33.75 45 10 4.38 67.5 50 10 4.38 135 55 10
Compound A acid Pyraclonil Visual weed control (%) - 20 DAA ECHCG ECHCO g of ae / ha ai ai / ha Observed Expected Observed Expected 4.38 0 25 - 50 - 8.75 0 80 - 75 - 0 33.75 0 - 0 - 0 67.5 0 - 15 - 0 135 0 - 20 - 4.38 33.75 65 25 75 50 8.75 33.75 90 80 95 75 4.38 67.5 85 25 70 58 8.75 67.5 95 80 80 79 4.38 135 90 25 70 60 8.75 135 95 80 90 80
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Compound A acid Pyraclonil Visual weed control (%) - 21DAA ECHCG g of ae / ha ai ai / ha Observed Expected 17.5 0 88 - 35 0 85 - 0 270 0 - 17.5 270 90 88 35 270 100 85
Compound A acid Pyraclonil Visual weed control (%) - 21DAA IPOHE g of ae / ha ai ai / ha Observed Expected 35 0 45 - 0 270 45 - 35 270 88 70 TABLE 9. Assets synergistic effect of Herbicidal Compositions
Piraclonila and Benzyl ester of compound A of Foliar Application on Weed Control in a Rice Cultivation System.
Benzyl ester of compound A Pyraclonil Visual weed control (%) -20 DAA ECHCO g of ae / ha ai ai / ha Observed Expected 4.38 0 40 - 0 33.75 0 - 0 67.5 15 - 0 135 20 - 4.38 33.75 50 40 4.38 67.5 60 49 4.38 135 75 52
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Benzyl ester of compound A Pyraclonil Visual weed control (%) -21 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 17.5 0 10 - 35 0 50 - 0 270 45 - 17.5 270 70 51 35 270 93 73
Benzyl ester of compound A Pyraclonil Visual weed control (%) -21 DAA ISCRU g of ae / ha ai ai / ha Observed Expected 8 0 20 - 16 0 0 - 0 67.5 0 - 0 135 0 - 0 270 0 - 8 67.5 50 20 16 67.5 30 0 8 135 70 20 16 135 100 0 8 270 95 20 16 270 60 0
TABLE 10. Synergistic Activity of Herbicidal Compositions
Oxadiazone and Foliar A Compound A Acid on the
Weed Control in a Rice Growing System.
Compound A acid Oxadiazone Visual weed control (%) - 20 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 8.75 0 10 - 0 31.25 15 - 0 62.5 20 - 0 125 30 - 8.75 31.25 20 24 8.75 62.5 50 28
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Compound A acid Oxadiazone Visual weed control (%) - 20 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 8.75 125 50 37
Compound A acid Oxadiazone Visual weed control (%) - 20 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 17.5 0 30 - 35 0 45 - 0 250 5 - 17.5 250 63 34 35 250 75 48
TABLE 11. Synergistic Activity of Herbicidal Compositions of
Oxadiazone and Benzyl Ester of Compound A of Foliar Application on the
Weed Control in a Rice Growing System.
Benzyl ester of compound A Oxadiazone Visual weed control (%) -20 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 4.38 0 10 - 8.75 0 10 - 17.5 0 15 - 0 31.25 15 - 0 62.5 20 - 0 125 30 - 4.38 31.25 40 24 8.75 31.25 40 24 17.5 31.25 60 28 4.38 62.5 60 28 8.75 62.5 30 28 17.5 62.5 30 32 4.38 125 50 37 8.75 125 55 37 17.5 125 50 41
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Benzyl ester of compound A Oxadiazone Visual weed control (%) -20 DAA IPOHE g of ae / ha ai ai / ha Observed Expected Benzyl ester of compound A Oxadiazone Visual weed control (%) -21 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 17.5 0 10 - 0 250 5 - 17.5 250 45 15
TABLE 12. Synergistic Activity of Herbicidal Compositions of Oxadiazone and N-Butyl Ester of Compound A of Foliar Application on the
Weed Control in a Rice Growing System.
N-Butyl Ester Compound Oxadiazone Visual weed control (%) -21 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 17.5 0 40 - 0 250 5 - 17.5 250 60 43
TABLE 13. Synergistic Activity of Herbicidal Compositions of
Saflufenacil and Foliar A Compound A Acid on the
Weed Control in a Rice Growing System.
Compound A acid Saflufenacil Visual weed control (%) - 20 DAA LEFCH g of ae / ha ai ai / ha Observed Expected 4.38 0 0 - 8.75 0 30 - 17.5 0 30 - 0 5 0 - 4.38 5 30 0 8.75 5 30 30 17.5 5 45 30
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Compound A acid Saflufenacil Visual weed control (%) - 20 DAA ECHCO CYPIR g of ae / ha ai ai / ha Observed Expected Observed Expected 4.38 0 40 - 30 - 0 5 0 - 0 - 0 10 40 - 0 - 0 20 40 - 100 - 4.38 5 45 40 100 30 4.38 10 70 64 70 30 4.38 20 80 64 100 100
TABLE 14. Synergistic Activity of Herbicidal Compositions
Saflufenacil and Benzyl ester A of Foliar Application on the
Weed Control in a Rice Growing System.
Benzyl ester of compound A Saflufenacil Visual weed control (%) -20 DAA ECHCO g of ae / ha ai ai / ha Observed Expected 4.38 0 60 - 8.75 0 80 - 0 10 40 - 0 20 40 - 4.38 10 40 76 8.75 10 99 88 4.38 20 90 76 8.75 20 90 88
Benzyl ester of compoundTHE Saflufenacil Visual weed control (%) - 20 DAA LEFCH g of ae / ha ai ai / ha Observed Expected 8.75 0 30 - 1.5 0 50 - 0 5 0 - 0 10 0 - 8.75 5 80 30 17.5 5 40 50 8.75 10 20 30 17.5 10 70 50
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Benzyl ester of compound A Saflufenacil Visual weed control (%) -20 DAA CYPIR g of ae / ha ai ai / ha Observed Expected 4.38 0 70 - 0 5 0 - 0 10 0 - 0 20 100 - 4.38 5 100 70 4.38 10 100 70 4.38 20 100 100
Benzyl ester of compound A Saflufenacil Visual weed control (%) -21 DAA ISCRU g of ae / ha ai ai / ha Observed Expected 8 0 20 - 16 0 0 - 0 10 0 - 0 20 0 - 8 10 100 20 16 10 70 0 8 20 70 20 16 20 70 0
TABLE 15. Synergistic Activity of Herbicidal Compositions
Oxadiargyl and Compound A Acid Foliar Application on Weed Control in a Rice Cultivation System.
Compound A acid Oxadiargyl Visual weed control (%) - 22 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 4.38 0 15 - 8.75 0 35 - 17.5 0 50 - 0 50 25 - 4.38 50 85 36 8.75 50 70 51
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Compound A acid Oxadiargyl Visual weed control (%) - 22 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 17.5 50 70 63
TABLE 16. Synergistic Activity of Herbicidal Compositions
Oxadiargyl and Benzyl Ester of Compound A of Foliar Application on the
Weed Control in a Rice Growing System.
Benzyl ester of compound A Oxadiargyl Visual weed control (%) -22 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 4.38 0 10 - 8.75 0 35 - 0 50 25 - 4.38 50 85 33 8.75 50 75 51
TABLE 17. Synergistic Activity of Sodium Compositions of
Acifluorfen and Benzyl Ester of Compound A of Foliar Application on the
Weed Control in a Rice Growing System.
Benzyl ester of Sodium of Visual weed control (%) compound A acifluorfen - 21 DAA ECHCO g of ae / ha ai ai / ha Observed Expected 8 0 40 - 0 140 0 - 0 280 25 - 8 140 60 40 8 280 65 55 TABLE 18. Assets Synergistic ade d and Compositions Herbicides
Bifenox (technical) and Benzyl Ester of Compound A of Foliar Application on Weed Control in a Rice Cultivation System.
Benzyl ester of compound A Bifenox Visual weed control (%) -22 DAA IPOHE g of ae / ha ai ai / ha Observed Expected
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8 0 10 - 16 0 40 - 32 0 45 - 0 360 40 - 0 720 65 - 8 360 70 46 16 360 80 64 32 360 70 67 8 720 95 69 16 720 80 79 32 720 100 81
Benzyl ester of compound A Bifenox Visual weed control (%) -22 DAA CYPIR g of ae / ha ai ai / ha Observed Expected 8 0 10 - 16 0 60 - 0 180 0 - 0 720 0 - 8 180 30 10 16 180 100 60 8 720 30 10 16 720 70 60
TABLE 19. Synergistic activity of Herbicidal Compositions of Bifenox (Fox®) and Benzyl Ester of Compound A of Foliar Application on Weed Control in a Rice Cultivation System.
Benzyl ester of compound A Bifenox Visual weed control (%) -21 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 16 0 10 - 32 0 45 - 0 180 55 - 16 180 95 60 32 180 100 75
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Benzyl ester of compound A Bifenox Visual weed control (%) -21 DAA CYPIR g of ae / ha ai ai / ha Observed Expected 8 0 30 - 0 180 0 - 0 360 0 - 0 720 08 180 30 30 8 360 85 30 8 720 50 30
TABLE 20. Synergistic Activity of Herbicidal Compositions
Flumioxazin and Benzyl ester of Compound A with Foliar Application on Weed Control in a Rice Cultivation System.
Benzyl ester of compound A Flumioxazin Visual weed control (%) -20 DAA ECHCO g of ae / ha ai ai / ha Observed Expected 8 0 40 - 16 0 60 - 0 140 60 - 0 280 70 - 8 140 90 76 16 140 90 84 8 280 90 82 16 280 100 88
TABLE 21. Synergistic Activity of Herbicidal Compositions of
Piraflufen-ethyl and Benzyl Ester of Compound A of Foliar Application on Weed Control in a Rice Cultivation System.
Benzyl ester of compound A Piraflufen-ethyl Visual weed control (%) -21 DAA ECHCG g of ae / ha ai ai / ha Observed Expected 8 0 45 - 0 5.3 15 -
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0 10.6 15 - 8 5.3 65 53 8 10.6 80 53
Benzyl ester of compound A Piraflufenetila Visual weed control (%) -21 DAA CYPIR g of ae / ha ai ai / ha Observed Expected 8 0 35 - 0 2.65 0 - 0 5.3 0 - 0 10.6 20 - 8 2.65 50 35 8 5.3 70 35 8 10.6 60 48
BRAPP Brachiaria platyphylla (Griseb.) Nash brachiaria, broad leaf
CYPDI Cyperus difformis L. ivy, smallflower umbrella
CYPES Cyperus esculentus L. tiririca, yellow
Cyperus cyperus would L. flatsedge, rice
DIGSA Digitaria sanguinalis (L.) Scop. crabgrass, wide
ECHCG Echinocloa crusgalli (L.) Beauv. backyard grass
ECHCO Echinocloa colona (L.) Link
IPOHE Ipomoea hederacea Jacq.
ISCRU Ischaemum rugosum Salisb.
morning glory junglerice, saramollagrass ivy
LEFCH Leptocloa chinensis (L.) Nees sprangletop, Chinese
SCPJU Schoenoplectus juncoides (Roxb.) Palla bulrush,
Japanese g of ae / ha = grams of acid equivalent per hectare g of ai / ha = gram of active ingredient per hectare
Obs = observed value
Exp = expected value when calculated using the Colby equation
DAA = days after application
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EXAMPLE II. EVALUATION OF HERBICIDAL MIXTURES APPLIED IN WATER TO CONTROL WEED IN TRANSPLANTED ALAGADO RICE
[000188] Weed seeds or seedlings of the desired test plant species were planted in powdered soil (mud) prepared by mixing a crumbled, non-sterile mineral soil (50.5 percent mud, 25.5 percent clay, and 24 percent sand, with a pH of about 7.6 and an organic matter content of about 2.9 percent) and water in a volumetric ratio of 1: 1. The prepared sludge was applied in 365 mL of aliquots in 473.18 cm ³ (16 oz (oz.)) Unperforated plastic pots with a surface area of 86.59 square centimeters (cm ² ) leaving a free top of 3 centimeters (cm) in each pot. The sludge was allowed to dry overnight before planting or transplanting. The 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 lid trays. Seedlings in the second and third growth leaf stages were transplanted in 840 mL of mud contained in 946.35 cm ³ (32 oz) unperforated plastic pots with a surface area of 86.59 cm ² 4 days before application of the herbicide. The swamp was created by loading the free top of the pots with 2.5 to 3 cm of water. When required to ensure good germination and healthy plants, a fungicide treatment and / or other chemical or physical treatment was applied. The plants were grown for 4 to 22 days in a greenhouse with a photoperiod of approximately 14 hours 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 + minor nutrients) in 2 g per 473.18 cm ³ pot (16 ounces) and 4 g per 946.35 cm ³ pot ( 32 ounces). Water was added on a regular basis to keep the
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[000189] The treatments consisted of the amino acid 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 with a SC and several herbicidal components alone and in combination. Compound A forms were applied on an equivalent acid base.
[000190] The forms of compound A (compound of Formula I) tested include:
Compound A acid
oh ₃ w ^/ n-Butyl Ester of Compound A
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Benzyl ester of compound A
[000191] Other herbicidal components were applied on an active ingredient basis and included protoporphyrinogen oxidase (PPO) inhibiting herbicides carfentrazone-ethyl formulated as Aim ^® EC, oxyfluorfen formulated as an SC or technical material, pyraclonil formulated as Piraclon ^® , oxadiazon formulated as Ronstar® 50W, saflufenacil formulated as Sharpen®, pentoxazone (technical grade material), bifenox formulated as Fox® or technical grade material and oxadiargil (technical grade material).
[000192] The treatment requirements for each herbicide compound or 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 area of application of 86.59 cm ² per pot.
[000193] For formulated compounds, a measured quantity was placed in an individual glass vial of 100 or 200 mL and was dissolved in a volume of 1.25% (volume / volume) of Agri-Dex ^® harvest oil concentrate for obtain application solutions. If the test compound does not dissolve easily, the mixture will be heated and / or sonicated.
[000194] For technical grade compounds, a heavy amount was placed in an individual glass vial of 100 to 200 mL and was dissolved in a volume of acetone to obtain concentrated raw material solutions. If the test compound does not dissolve easily,
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[000195] Applications were made by injecting with a pipette, appropriate amounts of the application solutions, individually and sequentially, in the water layer of the swamp. Control plants were treated in the same way with the virgin solvent. The applications were made so that all the treated plant material received the same concentrations of acetone and harvest oil concentrate.
[000196] The treated plants and control plants were placed in a greenhouse as described above and water was added when necessary to keep the swamp flooded. 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.
[000197] 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.).
[000198] 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)
[000199] A = observed effectiveness of active ingredient A in the same concentration as used in the mixture.
[000200] B = observed effectiveness of active ingredient B in the same
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[000201] Some of the tested compounds, application rates used, plant species tested, and are provided in tables 22 to 38.
TABLE 22. Synergistic Activity of Herbicidal Compositions of Compound A and Carfentrazone-ethyl from Water Applications on
Weed Control in a Rice Growing System.
Compound A acid Carfentrazonaetila Visual weed control (%) -21 DAA ECHCG g of ae / ha ai ai / ha Observed Expected 8.75 0 0 - 17.5 0 0 - 35 0 40 - 0 14 0 - 0 28 20 - 8.75 14 0 0 17.5 14 20 0 35 14 95 40 8.75 28 30 20 17.5 28 50 20 35 28 95 52
Compound A acid Carfentrazonaetila Visual weed control (%) -19 DAA ECHOR g of ae / ha ai ai / ha Observed Expected 42.4 0 15 - 0 215 65 - 42.4 215 100 70
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TABLE 23. Synergistic Activity of Herbicidal Compositions of Benzyl Ester of Compound A and Carfentrazone-ethyl from Water Applications on Weed Control in a Rice Growing System.
Benzyl ester of compound A Carfentrazonaetil Visual weed control (%)- 21 DAA LEFCH g of ae / ha ai ai / ha Observed Expected 8.75 0 20 - 17.5 0 30 - 35 0 55 - 0 28 10 - 8.75 28 40 28 17.5 28 40 37 35 28 65 60
TABLE 24. Synergistic Activity of Herbicidal Compositions of Compound A and Oxifluorphene (technical) from Water Applications on Weed Control in a Rice Cultivation System.
Compound A acid Oxyfluorfen Visual weed control (%) - 22 DAA CYPRO g of ae / ha ai ai / ha Observed Expected 10.6 0 0 - 21.2 0 25 - 42.4 0 95 - 0 180 50 - 10.6 180 90 50 21.2 180 90 63 42.4 180 100 98
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Compound A acid Oxyfluorfen Visual weed control (%) - 22 DAA SCPJU g of ae / ha ai ai / ha Observed Expected 8.75 0 60 - 17.5 0 70 - 35 0 95 - 0 180 0 - 0 360 0 - 8.75 180 55 60 17.5 180 90 70 35 180 100 95 8.75 360 75 60 17.5 360 80 70 35 360 100 95
TABLE 25. Synergistic Activity of Herbicidal Compositions of Compound A and Oxifluorphene (SC) from Water Applications on
Weed Control in a Rice Growing System.
Compound A acid Oxyfluorfen Visual weed control (%) - 22 DAA CYPRO g of ae / ha ai ai / ha Observed Expected 8.75 0 0 - 17.5 0 20 - 35 0 50 - 0 180 30 - 0 360 20 - 8.75 180 50 30 17.5 180 100 44 35 180 95 65 8.75 360 85 20 17.5 360 85 36 35 360 50 60
Compound A acid Oxyfluorfen Visual weed control (%) - 21DAA CYPRO g of ae / ha ai ai / ha Observed Expected 16 0 0 -
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32 0 20 - 64 0 85 - 0 135 0 - 0 270 0 - 16 135 20 0 32 135 20 20 64 135 95 85 16 270 40 0 32 270 60 20 64 270 100 85
TABLE 26. Synergistic Activity of Water Applications of Herbicidal Compositions of Oxifluorfen (SC) and Benzyl Ester of
Compound A on Weed Control in a Rice Growing System.
Benzyl ester of compound A Oxyfluorfen Visual weed control (%) -21 DAA CYPRO g of ae / ha ai ai / ha Observed Expected 32 0 90 - 0 135 0 - 0 270 0 - 32 135 95 90 32 270 100 90
TABLE 27. Synergistic Activity of Herbicidal Compositions of Compound A and Piraclonil from Water Applications on Weed Control in a Rice Cultivation System.
Compound A acid Pyraclonil Visual weed control (%) - 20 DAA ECHCG g of ae / ha ai ai / ha Observed Expected 8.75 0 40 - 17.5 0 30 - 0 45 0 - 8.75 45 100 40 17.5 45 100 30 TABLE 28. Synergistic Activity of Compositions H benzyl herbicides
ester of compound A and Pyraclonil from Water Applications on the
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Weed Control in a Rice Growing System.
Benzyl ester of compound A Pyraclonil Visual weed control (%) -20 DAA ECHOR g of ae / ha ai ai / ha Observed Expected 4.38 0 10 - 8.75 0 20 - 17.5 0 30 - 0 45 40 - 4.38 45 45 46 8.75 45 80 52 17.5 45 100 58
Benzyl ester of compound A Piraclonil Visual weed control (%) -20 DAA CYPRO g of ae / ha ai ai / ha Observed Expected 4.38 0 20 - 8.75 0 20 - 0 45 0 - 0 90 0 - 4.38 45 20 20 8.75 45 90 20 4.38 90 85 20 8.75 90 85 20
TABLE 29. Synergistic Activity of Herbicidal Compositions of Compound A Acid and Oxadiazone from Water Applications on Weed Control in a Rice Growing System.
Compound A acid Oxadiazon Visual weed control (%) - 21DAA ECHOR g of ae / ha ai ai / ha Observed Expected 8.75 0 10 - 17.5 0 20 - 35 0 35 - 0 62.5 15 - 0 125 20 - 8.75 62.5 40 24
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17.5 62.5 40 32 35 62.5 75 45 8.75 125 40 28 17.5 125 50 36 35 125 60 48
Compound A acid Oxadiazon Visual weed control (%) - 21DAA ECHOR g of ae / ha ai ai / ha Observed Expected 35 0 10 - 70 0 28 - 0 250 18 - 35 250 40 26 70 250 85 40
TABLE 30. Synergistic activity of Benzi Herbicidal Compositions
Compound A and Oxadiazone Ester from Water Applications on
Weed Control in a Rice Growing System.
Benzyl ester of compound A Oxadiazone Visual weed control (%) -21 DAA ECHOR g of ae / ha ai ai / ha Observed Expected 8.75 0 25 - 17.5 0 60 - 0 62.5 15 - 8.75 62.5 70 36 17.5 62.5 75 66
TABLE 31. Synergistic activity of n-Buti Herbicidal Compositions
Compound A and Oxadiazone Ester from Water Applications on
Weed Control in a Rice Growing System.
Compound A n-Butyl Ester Oxadiazone Visual weed control (%) -21 DAA ECHOR g of ae / ha ai ai / ha Observed Expected 35 0 25 - 70 0 38 - 0 250 18 -
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35 250 43 38 70 250 70 48
TABLE 32. Synergistic activity of Herbicidal Compositions of Compound A and Saflufenacil from Water Applications on Weed Control in a Rice Growing System.
Compound A acid Saflufenacil Visual weed control (%) - 20 DAA ECHCG LEFCH g of ae / ha ai ai / ha Observed Expected Observed Expected 17.5 0 50 - 0 - 35 0 95 - 30 - 0 10 0 - 0 - 0 20 10 - 0 - 17.5 10 85 50 30 0 35 10 100 95 30 30 17.5 20 70 55 30 0 35 20 100 96 70 30
Compound A acid Saflufenacil Visual weed control (%) - 20 DAA CYPRO g of ae / ha ai ai / ha Observed Expected 8.75 0 0 - 17.5 0 20 - 35 0 80 - 0 10 0 - 8.75 10 20 0 17.5 10 30 20 35 10 95 80
Compound A acid Saflufenacil Visual weed control (%) - 21DAA LEFCH g of ae / ha ai ai / ha Observed Expected 35 0 5 - 70 0 23 - 0 40 5 -
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35 40 58 33 70 40 55 38
TABLE 33. Synergistic activity of Herbicidal Compositions of Benzyl ester of Compound A and Saflufenacil from Water Applications on
Weed Control in a Rice Growing System.
Benzyl ester of compound A Saflufenacil Visual weed control (%) -20 DAA ECHOR g of ae / ha ai ai / ha Observed Expected 4.38 0 10 - 8.75 0 15 - 0 10 0 - 0 20 0 - 4.38 10 0 10 8.75 10 30 15 4.38 20 40 10 8.75 20 45 15
Benzyl ester of compound A Saflufenacil Visual weed control (%) -20 DAA LEFCH g of ae / ha ai ai / ha Observed Expected 4.38 0 08.75 0 20 - 17.5 0 30 - 0 10 0 - 0 20 0 - 4.38 10 50 0 8.75 10 40 20 17.5 10 100 30 4.38 20 100 0 8.75 20 60 20 17.5 20 100 30 TABLE 34. Activity and synergistic of Her Compositions n-Buti bicycles
Compound A Ester and Saflufenacil from Water Applications on
Weed Control in a Rice Growing System.
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Compound A n-Butyl Ester Saflufenacil Visual weed control (%) - 21 DAA LEFCH g of ae / ha ai ai / ha Observed Expected 35 0 8 - 0 40 5 - 35 40 28 12
TABLE 35. Synergistic activity of Herbicidal Compositions of Compound A and Pentoxazone from Water Applications on Weed Control in a Rice Growing System.
Compound A acid Pentoxazone Visual weed control (%) -21 DAA ECHCG g of ae / ha ai ai / ha Observed Expected 8.75 0 15 - 17.5 0 20 - 35 0 95 - 0 56.25 0 - 8.75 56.25 30 15 17.5 56.25 40 20 35 56.25 99 95
Compound A acid Pentoxazone Visual weed control (%) - 21 DAA CYPRO g of ae / ha ai ai / ha Observed Expected 35 0 70 - 0 56.25 0 - 0 112.5 0 - 35 56.25 85 70 35 112.5 100 70
Compound A acid Pentoxazone Visual weed control (%) -21 DAA FIMMI g of ae / ha ai ai / ha Observed Expected 8.75 0 0 - 0 56.25 25 -
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0 112.5 20 - 8.75 56.25 50 25 8.75 112.5 99 20 Compound A acid Pentoxazone Visual weed control (%) -21 DAA SCPJU g of ae / ha ai ai / ha Observed Expected 8.75 0 40 - 17.5 0 60 - 35 0 95 - 0 56.25 0 - 0 112.5 0 - 8.75 56.25 40 40 17.5 56.25 95 60 35 56.25 100 95 8.75 112.5 60 40 17.5 112.5 90 60 35 112.5 100 95 TABLE 36. Assets synergistic effect of benzi Herbicidal Compositions
ester of compound A and Pentoxazone from Water Applications on the
Weed Control in a Rice Growing System.
Benzyl ester of compound A Pentoxazone Visual weed control (%) -21 DAA CYPRO g of ae / ha ai ai / ha Observed Expected 4.38 0 30 - 8.75 0 60 - 0 56.25 0 - 0 112.5 0 - 4.38 56.25 80 30 8.75 56.25 75 60 4.38 112.5 50 30 8.75 112.5 80 60 TABLE 37. Activity and synergistic of Benzi Herbicidal Compositions
ester of compound A and Bifenox (technical) from Water Applications on Weed Control in a Rice Growing System.
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Benzyl ester of compound A Bifenox Visual weed control (%) -21 DAA ECHOR g of ae / ha ai ai / ha Observed Expected 8 0 20 - 16 0 45 - 32 0 60 - 0 720 40 - 8 720 85 52 16 720 100 67 32 720 100 76
TABLE 38. Synergistic activity of Herbicidal Compositions of Benzyl Ester of Compound A and Bifenox (Fox®) from Water Applications on Weed Control in a Rice Cultivation System.
Benzyl ester of compound A Bifenox Visual weed control (%) -21 DAA SCPMA g of ae / ha ai ai / ha Observed Expected 48 0 0 - 96 0 0 - 0 180 40 - 48 180 0 40 96 180 60 40
CYPRO Cyperus rotundus L. tiririca, purple
ECHCG Echinocloa crusgalli (L.) Beauv. backyard grass
ECHOR Echinocloa oryzoides (Ard.) Fritsch milim grass, early
FIMMI Fimbristylis miliacea (L.) Vahl fringerush, globe
LEFCH Leptocloa chinensis (L.) Nees sprangletop, Chinese
SCPJU Schoenoplectus juncoides (Roxb.) Palla bulrush, Japanese
SCPMA Schoenoplectus maritimus (L.) Lye clubrush, sea g of ae / ha = grams of acid equivalent per hectare g of ai / ha = gram of active ingredient per hectare
Obs = observed value
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Exp = expected value when calculated by the Colby equation DAA = days after application
EXAMPLE III. EVALUATION OF POST-EMERGENCY ACTIVITY OF MIXTURES IN CEREALS HARVESTS IN THE GREENHOUSE.
[000202] Seeds of the desired test plant species were planted in a Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm ² ). When required, to ensure good germination and healthy plants, a fungicide treatment and / or other chemical or physical treatment was applied. The plants were grown for 7 to 36 days in a greenhouse with a photoperiod of approximately 14 hours that was maintained at about 18 ° C during the day and about 17 ° C at night. Nutrients and water were added on a regular basis and supplementary lighting was provided with 1000 Watt metal halide hanging lamps when needed. The plants were used for testing when they reached the second or third stage of real leaf.
[000203] The treatments consisted of the benzyl ester of 4-amino3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) pyridine-2-carboxylic acid (Compound A), formulated as a SC, a second cereal herbicide alone, and then both in combination.
[000204] The forms of compound A (compound of Formula I) tested include:
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Benzyl ester of compound A
[000205] Other herbicidal components were applied on an active ingredient basis and included protoporphyrinogen oxidase inhibiting herbicides.
[000206] Measured aliquots of benzyl ester of 4-amino-3-chloro5-fluoro-6- (4-chloro-2-fluoro-3-methoxy-phenyl) pyridine-2-carboxylic acid (Compound A) were placed in vials glass of 25 milliliters (mL) and diluted in a volume of 1.25% (volume / volume) of Agri-Dex ^® harvest oil concentrate to obtain raw material solutions. The compost requirements are based on an application volume of 12 mL at a rate of 187 liters per hectare (L / ha). The spray solutions of the second cereal herbicide and experimental mixtures were prepared by adding the raw material solutions to the appropriate amount of dilution solution to form 12 ml of spray solution with active ingredients in combinations in two or three ways. The formulated compounds were applied to the plant material with an aerial Mandel trail sprayer equipped with an 8002E nozzle calibrated to release 187 L / ha over an application area of 0.503 square meters (m ² ) at a spray height of 46 cm ( 18 inches) above the average plant cover height. The control plants were sprayed in the same way with the virgin solvent.
[000207] The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent the elimination of test compounds. After 20 to 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 corresponds to complete death.
[000208] Colby's equation was used to determine the expected herbicidal effects of the mixtures (Colby, S.R. 1967. Calculation of the
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[000209] 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)
[000210] A = observed effectiveness of active ingredient A in the same concentration as used in the mixture.
[000211] B = observed effectiveness of active ingredient B at the same concentration as used in the mixture.
[000212] The compounds tested, application rates employed, plant species tested, and are provided in Table 39.
TABLE 39. Synergistic activity of Herbicidal Compositions of Benzyl ester of compound A and Bifenox of Foliar Application on the control of weed in a Cereal Growing System.
Benzyl ester of compound A Bifenox Visual weed control (%) -21 DAA PAPRH BRSNW ai ai / ha ai ai / ha Note Exp Note Exp 5 0 28 - 13 - 10 0 35 - 13 - 0 180 5 - 13 - 0 360 8 - 18 - 0 780 8 - 37 - 5 180 33 32 25 24 5 360 35 33 33 28 5 780 70 34 67 45 10 780 68 40 72 45
BRSNW Brassica napus L. rapeseed, oilseed (winter) PAPRH Papaver rhoeas L. poppy, common g of ae / ha = grams of acid equivalent per hectare g of ai / ha = gram of active ingredient per hectare
Obs = observed value
Exp = expected value when calculated using the Colby equation
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DAA = days after application
EXAMPLE IV. EVALUATION OF PRE-EMERGENCY HERBICID MIXTURES FOR PRE-EMERGENCY SOIL CONTROL FOR WEEDS
[000213] Seeds or seedlings of the desired test plant species were planted in a prepared soil matrix by mixing a mud earth (32 percent mud, 23 percent clay, and 45 percent sand, with a pH of about 6.5 and an organic matter content of about 1.9 percent) and limestone gravel in a ratio of 80 to 20. 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 ). [000214] The treatments consisted of the benzyl ester of 4-amino3-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. Compound A forms were applied on an equivalent acid base.
[000215] The forms of compound A (compound of Formula I) tested include:
Benzyl ester of compound A
[000216] Other herbicidal components were applied on an acid equivalent or active ingredient basis and included protoporphyrinogen oxidase (PPO) inhibiting herbicides, flumioxazin formulated as Payload ^® and oxadiazone formulated as Ronstar® 50W.
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[000217] Treatment requirements were calculated based on the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, and an application volume of 12 mL at a rate of 187 L / ha.
[000218] For treatments comprised of formulated compounds, measured amounts of compounds were placed individually in 25 ml glass vials and diluted in a volume of 1.25% (volume / volume) of Agri-Dex® harvest oil concentrate (COC) to obtain 12X of raw material solutions. If a test compound does not dissolve easily, the mixture will be heated and / or sonicated. The application solutions were prepared by adding an appropriate amount of each raw material solution (for example, 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of a 1.25% aqueous mixture (volume / volume) COC so that the final spray solutions contained 1.25% (volume / volume) COC.
[000219] For treatments comprised of technical compounds, heavy amounts can be placed individually in 25 ml glass vials and dissolved in a 97: 3 volume (volume / volume) acetone / DMSO to obtain 12X of raw material solutions. If a test compound does not dissolve easily, the mixture can be heated and / or sonicated. Application solutions can be prepared by adding an appropriate amount of each raw material solution (for example, 1 ml) and diluted to the appropriate final concentrations with the addition of 10 ml of a 1.5% aqueous mixture ( volume / volume) COC so that the spray solutions contain 1.25% (volume / volume) COC. When technical materials are used, concentrated raw material solutions can be added to spray solutions so that the final concentrations of acetone and DMSO in the
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[000220] For treatments comprised of formulated and technical compounds, heavy amounts of technical materials can be placed individually in 25 mL glass vials and dissolved in a 97: 3 volume (volume / volume) of acetone / DMSO to obtain 12X of solutions of raw material, and measured quantities of the formulated compounds can be placed individually in 25 ml glass vials and diluted in a volume of 1.5% (volume / volume) of COC or water to obtain 12X of solutions of raw material cousin. If a test compound does not dissolve easily, the mixture can be heated and / or sonicated. Application solutions can be prepared by adding an appropriate amount of each raw material 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 (volume / volume) of COC so that the spray solutions contain 1.25% (volume / volume) of COC. When required, additional water and / or 97: 3 (volume / volume) of acetone / DMSO can be added to the individual application solutions so that final concentrations of acetone and DMSO of the application solutions being compared are 8.1% and 0.25%, respectively.
[000221] All raw material solutions and application solutions were visually inspected for the compatibility of the compound before application. Spray solutions were applied to the soil with an aerial Mandel trail sprayer equipped with 8002E nozzles calibrated to release 187 L / ha over an application area of 0.503 m ² at a spray height of 46 cm (18 inches) above the height of the medium pot. The control pots were sprayed in the same way with the virgin solvent.
[000222] The treated and control pots were placed in a
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[000223] 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.).
[000224] 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)
[000225] A = observed effectiveness of active ingredient A in the same concentration as used in the mixture.
[000226] B = observed effectiveness of active ingredient B at the same concentration as used in the mixture.
[000227] Some of the tested compounds, application rates employed, tested plant species, and are provided in tables 40 to 41.
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TABLE 40. Synergistic activity of pre-emergence applications, applied to the benzyl ester compound A soil and Flumioxazin herbicidal compositions on weed control.
Benzyl ester of compound A Fumioxazin Visual weed control (%)- 28 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 16 0 13 - 32 0 23 - 0 105 70 - 0 210 70 - 0 420 90 - 16 105 100 74 32 105 80 77 16 210 85 74 32 210 100 77 16 420 100 91 32 420 100 92 Benzyl ester of compound A Fumioxazin Visual weed control (%)- 29 DAA XANST g of ae / ha ai ai / ha Observed Expected 16 0 0 - 32 0 5 - 0 105 18 - 0 210 48 - 16 105 38 18 32 105 30 22 16 210 40 48 32 210 65 50
Benzyl ester of compound A Fumioxazin Visual weed control (%) -28 DAA SETVI g of ae / ha ai ai / ha Observed Expected 16 0 10 - 32 0 10 -
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0 105 73 - 16 105 100 75 32 105 80 75
TABLE 41. Synergistic activity of pre-emergence applications, applied to soil Herbicidal compositions of benzyl ester of compound A and oxadiazone on weed control.
Benzyl ester of compound A Oxadiazone Visual weed control(%) - 32 DAA IPOHE g of ae / ha ai ai / ha Observed Expected 8 0 65 - 16 0 83 - 0 560 50 - 0 1120 100 - 8 560 100 83 16 560 100 91 32 560 100 100 IPOHE Ipomoea hederacea (L.) Jacq. morning glory, ivy
SETVI Setaria viridis (L.) Beauv. foxtail, green
XANST Xanthium strumarium L. thistle, common g of ae / ha = grams of acid equivalent per hectare g of ai / ha = gram of active ingredient per hectare
Obs = observed value
Exp = expected value when calculated by the Colby equation DAA = days after application

权利要求:
Claims (20)
[1]
1. Synergistic herbicidal composition, characterized by the fact that it comprises a herbicidally effective amount of:
(a) a compound of Formula (I)

[2]
2/4 (b) is piraflufen-ethyl, the weight ratio of (a) to (b) is 1.5: 1 to 1: 3; or (b) is saflufenacil, the weight ratio of (a) to (b) is 1: 0.3 to 1: 5.
2. Composition according to claim 1, characterized by the fact that it also comprises an adjuvant or agriculturally acceptable vehicle.
[3]
3. Composition according to claim 1 or 2, characterized by the fact that it also comprises a herbicidal protector.
[4]
Composition according to any one of claims 1 to 3, characterized in that (b) is acifluorphene.
[5]
Composition according to any one of claims 1 to 3, characterized by the fact that (b) is bifenox.
[6]
6. Composition according to any one of claims 1 to 3, characterized by the fact that (b) is carfentrazonaethyl.
[7]
Composition according to any one of claims 1 to 3, characterized in that (b) is flumioxazin.
[8]
8. Composition according to any one of claims 1 to 3, characterized by the fact that (b) is oxadiargyl.
[9]
9. Composition according to any one of claims 1 to 3, characterized by the fact that (b) is oxadiazone.
[10]
10. Composition according to any one of claims 1 to 3, characterized by the fact that (b) is oxyfluorfen.
[11]
11. Composition according to any one of claims 1 to 3, characterized by the fact that (b) is pentoxazone.
[12]
12. Composition according to any one of claims 1 to 3, characterized by the fact that (b) is pyraclonyl.
[13]
13. Composition according to any one of claims 1 to 3, characterized by the fact that (b) is piraflufen-ethyl.
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3/4
[14]
14. Composition according to any one of claims 1 to 3, characterized by the fact that (b) is saflufenacil.
[15]
15. Method for controlling undesirable vegetation, characterized by the fact that it comprises the steps of: contacting a plant, vegetation or its location, soil or water, with the soil or water allowing the growth of vegetation, with a quantity herbicidally effective composition as defined in any one of claims 1 to 14.
[16]
16. Method, according to claim 15, characterized by the fact that the undesired vegetation is controlled in no-till rice, water sowing and transplanted, cereals, wheat, barley, oats, rye, sorghum, corn (corn) / maize (maize), sugar cane, sunflower, rapeseed, canola, sugar beet, soy, cotton, pineapple, pastures, lawns, natural grazing land, uncultivated land, grass, tree orchards and vines, aquatic, control of industrial vegetation (IVM) or easements of passage (ROW).
[17]
17. Method according to claim 15 or 16, characterized by the fact that (a) and (b) are applied preemergentially to the plant or crop.
[18]
18. Method according to any one of claims 15 to 17, characterized in that the undesired vegetation is controlled in glyphosate- tolerant cultures, 5enolpyruvylchiquimate-3-phosphate (EPSP) synthase-, glufosinate- inhibitor, glutamine synthetase-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanediona-, phenylpyrazoline-, acetyl CoA carboxylase inhibitor (ACCase) -, imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) inhibitors or acetohydroxy acid synthase (AHAS) -,
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4/4 4-hydroxyphenyl-pyruvate dioxigenase (HPPD) inhibitor -, phytene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase inhibitor (PPO )-, cellulose biosynthesis inhibitor, mitosis inhibitor, inhibitor microtubule-, very long-chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I- inhibitor, photosystem II- inhibitor, triazine-, or bromoxynil.
[19]
19. Method, according to claim 18, characterized by the fact that the tolerant crop has multiple or stacked traits that confer tolerance to multiple herbicides or multiple modes of action.
[20]
20. Method according to any one of claims 15 to 19, characterized in that the undesirable vegetation comprises a herbicide resistant or tolerant plant.

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

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2015-05-05| B03H| Publication of an application: rectification [chapter 3.8 patent gazette]|Free format text: REFERENTE A RPI 2304 DE 03/03/2015, QUANTO AO ITEM (57). |

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2016-09-06| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]|

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

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

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2019-12-10| B06A| Patent application procedure suspended [chapter 6.1 patent gazette]|

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2020-03-24| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|

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2020-05-26| B16A| Patent or certificate of addition of invention granted [chapter 16.1 patent gazette]|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 19/07/2013, OBSERVADAS AS CONDICOES LEGAIS. |

优先权:

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申请号 | 申请日 | 专利标题

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US201261675067P| true| 2012-07-24|2012-07-24|

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US61/675,067|2012-07-24|

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US13/840,346|2013-03-15|

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US13/840,346|US8916499B2|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 a protoporphyrinogen oxidase inhibitor|

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