WO2011069202A1 - Nouvelle formulation de glyphosate - Google Patents
Nouvelle formulation de glyphosate Download PDFInfo
- Publication number
- WO2011069202A1 WO2011069202A1 PCT/AU2010/001663 AU2010001663W WO2011069202A1 WO 2011069202 A1 WO2011069202 A1 WO 2011069202A1 AU 2010001663 W AU2010001663 W AU 2010001663W WO 2011069202 A1 WO2011069202 A1 WO 2011069202A1
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- WO
- WIPO (PCT)
- Prior art keywords
- glyphosate
- formulation
- solid
- acid
- formulation according
- Prior art date
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- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 374
- 239000005562 Glyphosate Substances 0.000 title claims abstract description 323
- 229940097068 glyphosate Drugs 0.000 title claims abstract description 323
- 239000000203 mixture Substances 0.000 title claims abstract description 254
- 238000009472 formulation Methods 0.000 title claims abstract description 211
- 239000002253 acid Substances 0.000 claims abstract description 156
- 239000007787 solid Substances 0.000 claims abstract description 75
- 238000000034 method Methods 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 64
- 239000008187 granular material Substances 0.000 claims description 59
- 239000004094 surface-active agent Substances 0.000 claims description 46
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 44
- PDYXIVPKOMYDOK-UHFFFAOYSA-N Glyphosate-monoammonium Chemical group [NH4+].OC(=O)CNCP(O)([O-])=O PDYXIVPKOMYDOK-UHFFFAOYSA-N 0.000 claims description 32
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 claims description 32
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 27
- 239000002671 adjuvant Substances 0.000 claims description 21
- 238000002156 mixing Methods 0.000 claims description 21
- LIOPHZNMBKHGAV-UHFFFAOYSA-M potassium;2-(phosphonomethylamino)acetate Chemical compound [K+].OC(=O)CNCP(O)([O-])=O LIOPHZNMBKHGAV-UHFFFAOYSA-M 0.000 claims description 19
- -1 ammonium cations Chemical class 0.000 claims description 18
- 239000008233 hard water Substances 0.000 claims description 15
- 230000000717 retained effect Effects 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 239000011591 potassium Substances 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 239000012153 distilled water Substances 0.000 claims description 6
- YWICANUUQPYHOW-UHFFFAOYSA-M sodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].OP(O)(=O)CNCC([O-])=O YWICANUUQPYHOW-UHFFFAOYSA-M 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 230000014759 maintenance of location Effects 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 claims description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-O propan-1-aminium Chemical compound CCC[NH3+] WGYKZJWCGVVSQN-UHFFFAOYSA-O 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 81
- 239000007921 spray Substances 0.000 description 47
- 238000011282 treatment Methods 0.000 description 43
- OOKDYUQHMDBHMB-UHFFFAOYSA-N 3,6-dichloro-2-methoxybenzoic acid;2-(2,4-dichlorophenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CNC.COC1=C(Cl)C=CC(Cl)=C1C(O)=O.OC(=O)COC1=CC=C(Cl)C=C1Cl OOKDYUQHMDBHMB-UHFFFAOYSA-N 0.000 description 34
- 239000004009 herbicide Substances 0.000 description 29
- 230000002363 herbicidal effect Effects 0.000 description 28
- 244000100545 Lolium multiflorum Species 0.000 description 27
- 239000000463 material Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- 238000011068 loading method Methods 0.000 description 16
- 230000009467 reduction Effects 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 15
- 231100000674 Phytotoxicity Toxicity 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 241001330453 Paspalum Species 0.000 description 10
- 238000000540 analysis of variance Methods 0.000 description 10
- 239000003760 tallow Substances 0.000 description 10
- 244000088415 Raphanus sativus Species 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 235000000245 Raphanus raphanistrum subsp raphanistrum Nutrition 0.000 description 8
- 235000011380 Raphanus sativus Nutrition 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 235000013305 food Nutrition 0.000 description 7
- 241000595422 Hypochaeris radicata Species 0.000 description 6
- 241000209082 Lolium Species 0.000 description 6
- 241000522308 Oxalis pes-caprae Species 0.000 description 6
- 240000001949 Taraxacum officinale Species 0.000 description 6
- 241001148683 Zostera marina Species 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 235000019589 hardness Nutrition 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000008399 tap water Substances 0.000 description 6
- 235000020679 tap water Nutrition 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 5
- 238000005520 cutting process Methods 0.000 description 5
- 235000021073 macronutrients Nutrition 0.000 description 5
- 239000011785 micronutrient Substances 0.000 description 5
- 235000013369 micronutrients Nutrition 0.000 description 5
- 229910001414 potassium ion Inorganic materials 0.000 description 5
- 238000004382 potting Methods 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- 241000033016 Lolium rigidum Species 0.000 description 4
- 235000003805 Musa ABB Group Nutrition 0.000 description 4
- 241001127637 Plantago Species 0.000 description 4
- 235000015266 Plantago major Nutrition 0.000 description 4
- 235000005187 Taraxacum officinale ssp. officinale Nutrition 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- 208000037824 growth disorder Diseases 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000017074 necrotic cell death Effects 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 238000003359 percent control normalization Methods 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 241001435147 Arctotheca Species 0.000 description 3
- 238000001057 Duncan's new multiple range test Methods 0.000 description 3
- 240000004296 Lolium perenne Species 0.000 description 3
- 239000006057 Non-nutritive feed additive Substances 0.000 description 3
- 244000026791 Pennisetum clandestinum Species 0.000 description 3
- 241000219793 Trifolium Species 0.000 description 3
- 241000990144 Veronica persica Species 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 241001435146 Arctotheca calendula Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000052363 Cynodon dactylon Species 0.000 description 2
- 241001268782 Paspalum dilatatum Species 0.000 description 2
- 244000239204 Plantago lanceolata Species 0.000 description 2
- 235000021501 Rumex crispus Nutrition 0.000 description 2
- 244000207667 Rumex vesicarius Species 0.000 description 2
- 241000219870 Trifolium subterraneum Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 235000005545 Veronica americana Nutrition 0.000 description 2
- 240000005592 Veronica officinalis Species 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000001166 ammonium sulphate Substances 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 101100468275 Caenorhabditis elegans rep-1 gene Proteins 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 241000207894 Convolvulus arvensis Species 0.000 description 1
- 241000508725 Elymus repens Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 101100238610 Mus musculus Msh3 gene Proteins 0.000 description 1
- 235000010503 Plantago lanceolata Nutrition 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 description 1
- 244000286177 Raphanus raphanistrum Species 0.000 description 1
- 235000000241 Raphanus raphanistrum Nutrition 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 229920000142 Sodium polycarboxylate Polymers 0.000 description 1
- 235000006754 Taraxacum officinale Nutrition 0.000 description 1
- 235000000506 Veronica plebeia Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 230000009526 moderate injury Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004557 technical material Substances 0.000 description 1
- RJSZFSOFYVMDIC-UHFFFAOYSA-N tert-butyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC(C)(C)C RJSZFSOFYVMDIC-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
Definitions
- compositions that comprise a high loading of glyphosate on an acid equivalent basis.
- Such compositions may be fully formulated compositions that include glyphosate-synergising adjuvants, and that have a herbicidal activity per unit glyphosate acid equivalent that is comparable with the herbicidal activity of standard liquid glyphosate formulations such as Round-up CT.
- Such compositions may also be tank-mix formulations that require the separate addition of the formulation and the glyphosate-synergising materials to a spray tank.
- glyphosate N-phosphonyl methyl glycine
- the acid form is precipitated from the reaction mixture and the resulting wet cake is reacted with an appropriate base to form a water soluble salt.
- the intermediate technical grade glyphosate free acid is poorly water soluble and is not used as a herbicide.
- the herbicidal composition of salts of glyphosate is then prepared from the salt as an aqueous solution concentrate and may contain adjuvants such as surfactants that reinforce the herbicidal effect of glyphosate.
- WO 92/12,637 describes a process wherein glyphosate acid is mixed in powder form and under anhydrous conditions with a solid base such as sodium acetate. In this case salt formation does not occur during the process, but rather when the granule is added to water in the spray tank before use.
- WO 2007/143788 (Pentland and Flynn, "Herbicidal Composition and Method for Removing Unwanted Foliage”) describes a 2-pack method of preparing a spray tank mix of glyphosate comprising (a) providing glyphosate acid solid concentrate (glyphosate 95% pure, concentrate comprises 950g/kg acid equivalent); (b) an alkaline composition and (c) adding the glyphosate acid concentrate to a diluted aqueous mixture of the alkaline composition.
- the second pack must comprise alkali and will generally comprise liquid alkali (probably in admixture with a glyphosate-synergising surfactant) - the requirement to transport acid and alkaline packs in close proximity is problematic; (ii) the requirement for the glyphosate-synergising surfactant to be compatible with the alkaline material can be problematic, and can limit the suitable glyphosate-synergising surfactants that can be used in the second pack; (iii) the order of addition of the 2 packs is critical for successful application of glyphosate; (iv) the rate of addition of the glyphosate concentrate is critical for successful application of glyphosate - in particular if the glyphosate concentrate is added too rapidly to the diluted alkaline spray water, some of the concentrate may accumulate on the bottom of the spray tank and may not be properly neutralised
- the present inventors have surprisingly found that glyphosate acid in relatively large amounts (ie in a molar ratio of 10% or greater) can be incorporated into solid compositions comprising glyphosate salts without adversely affecting the formulation or dissolution properties of the compositions.
- the present invention therefore provides formulations having a higher glyphosate acid equivalent loading than could be achieved by the methods of the prior art.
- the invention therefore provides a solid glyphosate formulation comprising glyphosate acid and further comprising at least one agriculturally acceptable salt of glyphosate, wherein the glyphosate acid and the at least one glyphosate salt are in admixture and wherein the mole ratio of glyphosate acid to total glyphosate moieties in the formulation is at least 10%.
- a method of using the formulation, or a diluted form thereof, in removing unwanted foliage is also provided.
- Figure 1 illustrates whole plot weed phytotoxicity ratings for formulations according to the present invention when compared to the commercially available formulations PowerMAX and Weedmaster Duo.
- Figure 2 illustrates broadleaf plant counts in a plot after treatment with formulations according to the present invention when compared to the commercially available formulations PowerMAX and Weedmaster Duo.
- Figure 3 illustrates fresh weight of annual ryegrass treated with formulations according to the present invention (glyphosphate 800 SG containing a cocobetaine (CB) or a cocoamidopropyl betaine (CAPB)) and two commercially available formulations (Roundup Biactive (RUP Biactive) 360SL and Macphersons Bi Dri (700G/KG SG))
- Figure 4 illustrates fresh weight of wild radish treated with formulations according to the present invention (glyphosphate 800 SG containing a cocobetaine (CB) or a cocoamidopropyl betaine (CAPB)) and two commercially available formulations (Roundup Biactive (RUP Biactive) 360SL and Macphersons Bi Dri (700G/KG SG)).
- formulations according to the present invention glycophosphate 800 SG containing a cocobetaine (CB) or a cocoamidopropyl betaine (CAPB)
- Roundup Biactive (RUP Biactive) 360SL and Macphersons Bi Dri (700G/KG SG)
- Figure 5 illustrates a comparison of fresh weight of annual ryegrass treated with various ammonium glyphosphate formulations according to the present invention.
- Figure 6 illustrates fresh weight of annual ryegrass plants sprayed with formulations according to the present invention (900g glyphosate acid equivalent/kg granule mixed with a range of surfactants in water.
- TA ethoxylated tallow amine
- CB cocobetaine
- AO amine oxide
- ADA alkyl diamine alkoxylate).
- Dri Flo Macphersons 840 Dri Flo which contains 840g glyphosate acid equivalent as the ammonium salt.
- Figure 7 illustrates fresh weight of annual ryegrass plants sprayed with various potassium glyphosate/acid formulations according to the present invention. Detailed description of the invention
- glyphosate acid means glyphosate in the free acid form.
- glyphosate acid equivalent As used herein the term "glyphosate acid equivalent”, “glyphosate ae”, “acid equivalent” or “ae” refers to the weight of glyphosate present in a formulation calculated on the basis that all of the glyphosate is present in the acid form.
- the invention provides a solid glyphosate formulation comprising glyphosate acid and further comprising at least one agriculturally acceptable salt of glyphosate, wherein the glyphosate acid and the at least one glyphosate salt are in uniform admixture and wherein the mole ratio of glyphosate free acid to total glyphosate moieties in the formulation is at least 10%.
- the mole ratio of glyphosate acid to total glyphosate moieties is less than 50%, and is preferably less than 40%, and even more preferably less than 30%.
- the glyphosate salt is monoammonium glyphosate
- the weight ratio of glyphosate acid to total glyphosate (acid equivalent) is in the range of 9-50%, preferably 15 - 40%, more preferably 22 - 35%.
- the molecular weight of glyphosate acid is 169.1 and the molecular weight of glyphosate monoammonium salt is 186.1.
- the molecular weight of glyphosate monopotassium salt is 207.
- the following calculation may be used to establish the ratio of the weight of glyphosate acid to the total weight of glyphosate acid and the monoammonium glyphosate.
- glyphosate acid is available as a 95% strength material or a 98% strength material or similar, and it is necessary to adjust the weight of these materials by a purity factor to calculate the quantity of glyphosate present. Similar considerations apply to glyphosate monoammonium salts and other preformed salts.
- the presence of the glyphosate free acid in the formulation allows for a higher loading of glyphosate ae than the use of agriculturally acceptable salts of glyphosate alone.
- the present inventors have surprisingly found that the formulations of the present invention readily dissolve in aqueous solution, thus allowing for ease of mixing before use in spray tanks and the like. The ease of dissolution also avoids the need for using the alkali composition required in WO 2007/143788 with all its attendant disadvantages.
- the formulation preferably consists of granules, preferably in the range of from 0.5 mm to 3 mm in length.
- the formulation is in the form of granules suitable for use in a spray tank.
- Such granular formulations are sold for farm use.
- the granules are combined with water in the spray tank, and if the granules are fully formulated, there is no need for other additives. However, if the granules do not contain glyphosate synergising materials, these may be separately added to the spray tank to achieve optimal performance.
- the formulation consists of a powder, and said powder may further be presented in a water soluble bag.
- glyphosate formulations typically require the presence of one or more adjuvants, often surfactants, which enhance spray performance or the activity of the glyphosate.
- Other components may also be present, such as ammonium sulphate which acts as a processing aid and water conditioner.
- the formulation optionally comprises one or more adjuvants.
- the adjuvant may be of a type registered for use with glyphosate. Examples of suitable adjuvants are provided in WO 2007/143788, the disclosure of which is hereby incorporated by reference.
- the adjuvant comprises a glyphosate synergising surfactant. These have been discussed, for example, in US6881706, the disclosure of which is hereby included by reference.
- the glyphosate synergising surfactant is selected from the group consisting of cocobetaine cocoamidopropylbetaine, tallowamine-15-ethoxylate (eg the material sold as TERWET 3780, CAS 61791-26-2), alkylpolyglycosides, and alkyldiaminealkoxylates such as the material sold as TERWET 1221.
- Cocobetaine is the reaction product of dimethylcoconut amine with chloroacetic acid. Coconut amine primarily consists of C12 and C14 primary amines.
- Cocobetaine is a registered agrochemical surfactant. However, cocoamidopropylbetaine is considerably cheaper and may therefore be a preferred adjuvant in solid glyphosate formulations of the present invention.
- the weight ratio of glyphosate synergising surfactant (dry weight basis) to glyphosate acid equivalent is at least 50:700, preferably is at least 80:700 and more preferably 100:700.
- the formulation also optionally comprises other components which act as fillers, processing aids, or the like. Such additional components are well known to those skilled in the art.
- the formulation is fully formulated, which means that the formulation can be mixed with water and used directly as a herbicide, without the need to add additional components.
- the at least one glyphosate salt is an agriculturally acceptable salt arising from the neutralisation of one or more labile glyphosate hydrogens.
- the salt may comprise cations chosen from the group consisting of ammonium, sodium, potassium, ethanolammonium, diethanolammonium, triethanolammonium, propylammonium, isopropylammonium, and trimesium cations.
- Ammonium ions have a low molecular mass and therefore monoammonium glyphosate provides comparatively high loadings of glyphosate acid equivalent when mixed with glyphosate acid.
- the salt comprises ammonium cations.
- the at least one glyphosate salt is monoammonium glyphosate, and the percent weight ratio of glyphosate acid to total glyphosate moieties is in the range 9- 50%, 15 - 40%, more preferably 22 - 35%.
- the amount of glyphosate in the formulation calculated on an acid equivalent basis is at least 730 g/kg, more preferably at least 750 g/kg, more preferably at least 780 g/kg, and even more preferably at least 800 g/kg
- the formulation comprising ammonium ions is suitable for use in a two-pack formulation.
- glyphosate moieties and optionally one or more other components are provided in one pack and complementary components such as glyphosate synergising surfactants are provided in the other.
- the contents of the two packs are individually added to water in the spray tank.
- the resulting liquid formulation is then suitable for use as a herbicide.
- the amount of glyphosate in the formulation calculated on an acid equivalent basis is at least 800g/kg, preferably at least 850 g/kg, more preferably at least 880 g/kg, and even more preferably at least 900 g/kg.
- the order of addition of the two packs to the spray water is not critical, and the rate of addition of pack contents to spray water is also not critical.
- the formulation is a granule.
- ammonium glyphosate provides for comparatively high loadings of glyphosate acid equivalent
- other ions may be selected to provide desirable properties to the formulation.
- the potassium ion provides granules with relatively high mechanical strength and hardness. This allows the formulation to be stored in bags rather than in bag-in-box packaging. Potassium ions are particularly useful in cases where betaine surfactants are used as adjuvants because the use of betaine surfactants in a glyphosate formulation tends to result in softer granules. The use of potassium glyphosate compensates for this softening.
- the at least one glyphosate salt comprises potassium cations.
- the amount of glyphosate in the formulation calculated on an acid equivalent basis is at least 600g/kg, preferably at least 650 g/kg, more preferably at least 680 g/kg, even more preferably at least 700 g/kg, and most preferably at least 720 g/kg.
- the potassium ions may be mixed with sodium ions. Such a mixture can retain the hardness associated with the use of potassium ions while also allowing for higher glyphosate acid equivalent loadings because the sodium ion has a lower molecular mass than potassium.
- the at least one glyphosate salt comprises potassium and sodium cations.
- the potassium ions may also be mixed with ammonium ions.
- the solid glyphosate formulation of the invention meets a first criterion in which lg of solid glyphosate formulation is mixed with lOOg of 1WHO hard water and passed through a 75 micron sieve with retention of less than 0.02g residue on the sieve, and also meets a second criterion in which 3.5g of solid glyphosate formulation is mixed with lOOg of 2 WHO hard water and passed through a 75 micron sieve to leave more than 0.03g of residue on the sieve.
- the addition to distilled water of 1% glyphosate acid equivalent of fully formulated glyphosate granules according to the invention provides a final pH in the range 1.5 - 3.5, and more preferably in the range 2 -3.
- the addition to distilled water of 1% glyphosate acid equivalent of the glyphosate pack in a 2-pack system provides a final pH in the range 1.5 - 3.5, and more preferably in the range 2 - 3.
- the present invention further provides a method of removing unwanted foliage comprising administering a diluted form of a solid glyphosate formulation according to the present invention to said foliage.
- a method of preparing a solid glyphosate formulation comprising glyphosate acid and ammonium glyphosate wherein the mole ratio of glyphosate acid to total glyphosate moities in the formulation is at least 10%, said method comprising the step of mixing ammonium glyphosate with glyphosate acid.
- said formulation further comprises sodium glyphosate
- said method comprises the additional step of partially neutralising the glyphosate acid with sodium hydroxide.
- the glyphosate acid may be in the form of an 85% wetcake. Moisture in the wetcake may be at least partially removed in the granule drying stage..
- Example 1 800 g/kg glyphosate ae granules (denoted Gly 800)
- cocoamidopropylamidopropane was purchased as 35% aqueous solution and evaporated to achieve 56% aqueous solution.
- the above ingredients were blended together in a food processor.
- the mixture was able to be deformed under pressure, without the occurrence of crumbling.
- the mixture was extruded through a small basket extruder (1 mm mesh) to form granules and some longer strands.
- the granules and strands were dried overnight in an oven at 40 deg C. and sieved to recover granules (1.0 - 2.0 mm length). In commercial use, the drying process may be carried out in a fluid bed dryer.
- the properties of the granules are given in the following table:
- Protocols MT 171, 176, and 179 are CIPAC international standard protocols.
- Example 2 Preparation of 1 WHO standard hard water
- Example 3 Preparation of 2-pack system with 900 g/kg glyphosate acid equivalent granules in the glyphosate pack.
- the 2-pack system comprises a solid glyphosate pack and a second adjuvant pack which may be solid or liquid.
- Example 3a Glyphosate pack with partial potassium hydroxide neutralisation:
- a first step fine crystals of glyphosate were mixed with KOH pellets. Water was added and a thick slurry was produced, with evolution of heat. The slurry was dried at 60 deg C until the resultant paste was dry enough to extrude (moisture content less than 5%, preferably between 4 and 5%). The extrudable paste was extruded into granules using a small basket extruder (Benchtop Granulator, Tsutsui Scientific Instruments Co Ltd, No 5752, Date 1995.3, made in Japan), and the granules were dried at 60 deg C for 8 hrs.
- a small basket extruder Benchtop Granulator, Tsutsui Scientific Instruments Co Ltd, No 5752, Date 1995.3, made in Japan
- Example 3b Glyphosate pack with mixture of acid and ammonium salt:
- a first step fine glyphosate crystals were mixed with glyphosate mono-ammonium salt. Water was added to form an extrudable paste. The paste was extruded into granules using a small basket extruder as in example 3a, and the granules were dried at 60 deg C for 8 hrs. After drying, the granules were sieved and granules in the size range 1.0 - 2.0 mm were collected as product. In this example, 75% by weight of glyphosate present was in salt form.
- Terwet 1221 (alkyl diamine alkoxylate, sold by Huntsman Australia) was molten at 60 deg C in an oven. Urea pellets were passed through a hammer mill (BECY AG serial no 5080030021, supplied by TECO Australia Pty ltd) using a coarse mesh (2.5 mm) to obtain a fluffy powder. The molten Terwet 1221 was sprayed onto the milled urea and mixed to uniformity. During mixing, the temperature of the molten material decreased and fell below the melting point of the Terwet 1221 to form a wax. The mixture was allowed to harden at room temperature and was then passed through a 1.0 mm sieve. Lumps were broken up and passed through the sieve.
- Geropon T/36 sodium polycarboxylate, CAS no 37199-81-8, sold by Rhodia in Australia
- milled ammonium sulfate were added to the Terwet-urea mixture.
- the Geropon T/36 acts as a drop size regulator and functions as a spray drift control agent. Then a small amount of water was added to the mixture and the resultant paste was extruded into granules with a basket extruder (as in previous examples). The granules were dried overnight at room temperature and sieved to collect granules in the size range 1.0 - 2.0 mm.
- Terwet 3780 consisted of tallowamine-15-ethoxylate (liquid). Note that other glyphosate tank-mix adjuvants may also be used in the adjuvant pack.
- Example 4 Formulation Stability in tap water (CIPAC MT 179 test).
- a 100 ml measuring cylinder was taken and 50 ml tap water added at 25 deg C.
- Sufficient glyphosate pack material was added to the measuring cylinder to provide a 2.5% level of glyphosate in 100 ml, and (optionally) sufficient adjuvant pack material was added to the measuring cylinder to provide a 0.6% level of adjuvant in 100 ml.
- Additional water was added to make the liquor level in the measuring cylinder up to 100 ml at 25 deg C.
- the measuring cylinder was inverted 15 times by hand through an angle of 180 deg, and back to the original position. After 15 minutes standing, the liquor in the cylinder was poured through a 75 micron sieve.
- the filtrate was collected in a beaker and the residues were retained on the sieve were transferred to a weighed Petri dish. The transferred residues were dried in an oven and the amount after 15 minutes were measured. After 18 hrs the collected filtrate was passed through a 75 micron sieve and retained solids were transferred into a weighed Petri dish. The percentage of starting solids retained on a 75 micron sieve after 18 hrs standing was calculated by adding 15 minute and 18hr results. Using materials prepared in example 3, the results were as follows:
- Fl was an unsatisfactory formulation with a high sieve test residue.
- Example 5 Solution pH at various mole ratios of glyphosate acid and glyphosate monoammonium salt, and in the presence of various glyphosate-synergising surfactants.
- Example 5.1 Solution pH at various mole ratios of glyphosate acid and glyphosate monoammonium salt, and in the presence of various glyphosate-synergising surfactants.
- Example 6 Composition and sediment values (75 micron screen) for a range of fully formulated 800 g/kg glyphosate formulations at various mole ratios of glyphosate acid to glyphosate mono-ammonium salt.
- the mixed acid-salt formulations of this invention will enable higher levels of glyphosate (on an acid-equivalent basis) to be included in a granular formulation.
- Example 7 Composition and sediment values (75 micron screen) for a range of glyphosate pack 900 g/kg formulations (part of a 2-pack system) at various mole ratios of glyphosate acid to glyphosate mono-ammonium salt. Data is for addition of the glyphosate pack only to water of different hardnesses.
- Example 8a 800 g/kg glyphosate ae granules (denoted Gly 800) using 98% glyphosate acid in place of 95% glyphosate acid
- Example 8b 800 g/kg glyphosate ae granules (denoted Gly 800) using 85% glyphosate acid wet cake in place of 95% glyphosate acid ingredient parts
- Cocoamido-propyl betaine (56% aq soln) 205
- Glyphosate-potassium salt a. Dissolve KOH in water to produce a 50% w/w solution
- the CIPAC Method MT 178 Attrition and Friability may be used to assess granule hardness.
- Attrition resistance a/w x 100%
- the trial site was densely covered, including:
- Capeweed (Arctotheca calendula), Dandelion (Taraxacum officinale), Dock Curled (Rumex crispus), Flatweed (Hypochaeris radicata), Plantain (Plantago lanceolata), Soursob (Oxalis pes-caprae), Sub Clover (Trifolium subterranean), Creeping Speedwell (Veronica persica).
- Gly 800 provided effective control of a range of grass and broadleaf weeds present in this trial. Gly 800 achieved equivalent levels of weed control to the industry standards, Roundup PowerMAX and Weedmaster Duo, when applied at the same rate of glyphosate.
- Figure 1 illustrates whole plot weed phytotoxicity ratings for formulations according to the present invention when compared to the control PowerMAX and Weedmaster Duo.
- Figure 2 illustrates broadleaf plant counts in a plot after treatment with formulations according to the present invention when compared to the control PowerMAX and Weedmaster Duo.
- Herbicide solution present as the isopropylamine and Duo
- the mean rating, across all treatments at each assessment time increased from 5.2 to 7.2, then to 9.1, at the last assessment time, showing increased phytotoxicity over time.
- each broadleaf weed present were low to medium, with Clover and Soursob being the most numerous with average numbers of 4.1 & 3.8 plants per 0.1m 2 , with the other 6 weeds present ranging from 1.8 to 2.6 plants per 0. lm 2 .
- Gly 800 provided effective control of a range of grass and broadleaf weeds present in this trial.
- Gly 800 achieved equivalent levels of weed control to the industry standards, Roundup PowerMAX and Weedmaster Duo, when applied at the same rate of glyphosate
- Glyphosate acid (98%w/w) 223 is example 11
- Glyphosate acid (98%w/w) 223 is example 11
- Mono-NH4 glyphosate 653 is example 12
- Trial A-ARG relates to formulations according to the present invention comprising (i) cocoamidopropylbetaine (CAPB) and (ii) cocobetaine (CB) surfactants tested with annual ryegrass.
- CAPB cocoamidopropylbetaine
- CB cocobetaine
- Roundup Biactive® SL and Macphersons Bi Dri 700SG were the commercial standards.
- Trial A-WR relates to formulations according to the present invention comprising (i) cocoamidopropylbetaine (CAPB) and (ii) cocobetaine (CB) surfactants tested with wild radish.
- CAPB cocoamidopropylbetaine
- CB cocobetaine
- Roundup Biactive® SL and Macphersons Bi Dri 700SG were the commercial standards.
- Trial B relates to formulations according to the present invention comprising (i) cocoamidopropylbetaine (CAPB), (ii) cocobetaine (CB), (iii) cocoamineoxide (AO), (iv) ethoxylated tallowamine (15EOs) (TA), and (v) alkyldiamine alkoxylate (ADA) tested with annual rye grass.
- CAPB cocoamidopropylbetaine
- CB cocobetaine
- AO cocoamineoxide
- TA ethoxylated tallowamine
- ADA alkyldiamine alkoxylate
- formulations according to the present invention comprising (i) cocoamidopropylbetaine (CAPB), (ii) cocobetaine (CB), (iii) cocoamineoxide (AO), (iv) ethoxylated tallowamine (15EOs) (TA), and (v) alkyldiamine alkoxylate (ADA) tested with annual rye grass.
- CAPB cocoamidopropylbetaine
- CB cocobetaine
- AO cocoamineoxide
- TA ethoxylated tallowamine
- ADA alkyldiamine alkoxylate
- CB cocobetaine
- CAPB cocoamidopropyl betaine
- the annual ryegrass was at the early tillering stage (2 tillers) when sprayed with the herbicide treatments.
- Herbicide formulations were applied using an enclosed laboratory track-sprayer fitted with three 110° flat fan nozzles ("Teejet” ® XR11001-VS) spaced at 50cm intervals across the boom.
- the boom moved along a fixed track at 6 km h-1, sprayed at a water volume of 64 L/ha with a pressure of 200 kPa.
- Seedlings were harvested 14 days after spray application by cutting foliage off at the base immediately prior to weighing on an "AND FX" 300 electronic balance (range 0- 300 g).
- Example 12 Efficacy of two variants of Glyphosate 800SG (cocobetaine or cocoamidobetaine) and Two Commercial Standards on Wild Radish (Trial No. A - WR) INTRODUCTION
- Wild radish (Raphanus raphanistrum) seeds (3/pot) were sown to a depth of 3mm in 10cm diameter pots filled with potting mix (Australian Standard 3743) that had been amended with macro and micronutrients for optimal growth.
- the wild radish plants were in the rosette stage with 5-7 leaves when sprayed with the herbicide.
- Herbicide formulations were applied using an enclosed laboratory track-sprayer fitted with three 110° flat fan nozzles ("Teejet” ® XR11001-VS) spaced at 50cm intervals across the boom.
- the boom moved along a fixed track at 6 km h-1, sprayed at a water volume of 64 L/ha with a pressure of 200 kPa.
- Seedlings were harvested 14 d after spray application by cutting foliage off at the base immediately prior to weighing on an "AND FX" 300 electronic balance (range 0-300 g).
- Glyphosate Glyphosate 800SG Glyphosate Bi RUP Rate rate CB 800SG Dri. Biactive Mean g acid/ha CAPB
- the present inventors evaluated the efficacy of partially neutralized glyphosate formulations in a pot trial.
- the project was carried out at Agricultural and Food Precinct in Werribee, Victoria.
- the annual ryegrass was at the early tillering stage (2 tillers) when sprayed with the herbicide treatments.
- Herbicide formulations were applied using an enclosed laboratory track-sprayer fitted with three 110° flat fan nozzles ("Teejet” ® XR11001-VS) spaced at 50cm intervals across the boom.
- the boom moved along a fixed track at 6 km h-1, sprayed at a water volume of 64 L/ha with a pressure of 200 kPa.
- Seedlings were harvested 14 days after spray application by cutting foliage off at the base immediately prior to weighing on an "AND FX" 300 electronic balance (range 0- 300 g).
- LSD least significant differences
- the surfactants were; (i) an ethoxylated tallow amine plus a cocobetaine (TA +CB), (ii) a cocobetaine (CB), (iii) an amine oxide (AO) and (iv) an alkyl diamine alkoxylate (ADA) (Table 14.1).
- the efficacy of these formulations was compared with that of a commercial granule formulation Macphersons 840 Dri Flo (Dri Flo) which was used in conjunction with Zest.
- Zest contains a 530g/L ethoxylated tallow amine plus 410g/L ethoxylated alcohol.
- Surfactant TA+CB was made by mixing equal parts of TA (a neat liquid) with CB (35% aqueous liquid as provided by the vendor)
- Surfactant CB was a 35% aqueous liquid as provided by the vendor.
- Surfactant AO was a 32-35% aqueous liquid as provided by the vendor.
- Surfactant ADA was a wax formulated as described in example 3c (adjuvant pack, non- alkaline, solid). Table 14.1. Surfactant formulations used in trial.
- the granules and surfactant were added at the required rates directly to the water spray canister to give a total spray weight of l,300g (Table 14.2, Table 14.3).
- the annual ryegrass was at the tillering stage (3 tillers) when sprayed with the herbicide treatments.
- Herbicide formulations were applied using an enclosed laboratory track-sprayer fitted with three 110° flat fan nozzles ("Teejet” ® XR11001-VS) spaced at 50cm intervals across the boom. The boom moved along a fixed track at 6 km h-1, sprayed at a water volume of 64 L/ha with a pressure of 200 kPa. There were eight replicates for each treatment. Assessment
- Seedlings were harvested 14 days after spray application by cutting foliage off at the base immediately prior to weighing on an "AND FX" 300 electronic balance (range 0- 300 g).
- LSD least significant differences
- the present inventors evaluated the efficacy of partially neutralized glyphosate formulations in a pot trial.
- the project was carried out at Agricultural and Food Precinct in Werribee, Victoria. • MATERIALS AND METHODS
- Bi Dri 700 as NH 4 + salt Cocobetaine Herbicide and Spray Mix
- the annual ryegrass was at the early tillering stage (2 tillers) when sprayed with the herbicide treatments.
- Herbicide formulations were applied using an enclosed laboratory track-sprayer fitted with three 110° flat fan nozzles ("Teejet” ® XR11001-VS) spaced at 50cm intervals across the boom.
- the boom moved along a fixed track at 6 km h-1, sprayed at a water volume of 64 L/ha with a pressure of 200 kPa.
- Seedlings were harvested 14 days after spray application by cutting foliage off at the base immediately prior to weighing on an "AND FX" 300 electronic balance (range 0- 300 g).
- LSD least significant differences
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Abstract
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
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BR112012015773-6A BR112012015773B1 (pt) | 2009-12-08 | 2010-12-08 | Formulação de glifosato, seu método de preparo e método de remoção de folhagem indesejada |
EP10835302.0A EP2509425A4 (fr) | 2009-12-08 | 2010-12-08 | Nouvelle formulation de glyphosate |
AU2010330690A AU2010330690B2 (en) | 2009-12-08 | 2010-12-08 | Novel glyphosate formulation |
US13/514,649 US8852642B2 (en) | 2009-12-08 | 2010-12-08 | Glyphosate formulation |
CA2783484A CA2783484C (fr) | 2009-12-08 | 2010-12-08 | Nouvelle formulation de glyphosate |
BR122017002517-1A BR122017002517B1 (pt) | 2009-12-08 | 2010-12-08 | Formulação de glifosato, seu método de preparação, e método para remoção de folhagem indesejada |
NZ602144A NZ602144A (en) | 2009-12-08 | 2010-12-08 | Novel glyphosate formulation |
ZA2012/04182A ZA201204182B (en) | 2009-12-08 | 2012-06-07 | Novel glyphosate formulation |
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AU2009905979A AU2009905979A0 (en) | 2009-12-08 | Novel glyphosate formulation | |
AU2009905979 | 2009-12-08 |
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WO2011069202A1 true WO2011069202A1 (fr) | 2011-06-16 |
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PCT/AU2010/001663 WO2011069202A1 (fr) | 2009-12-08 | 2010-12-08 | Nouvelle formulation de glyphosate |
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US (1) | US8852642B2 (fr) |
EP (2) | EP2509425A4 (fr) |
AU (1) | AU2010330690B2 (fr) |
BR (2) | BR122017002517B1 (fr) |
CA (1) | CA2783484C (fr) |
NZ (1) | NZ602144A (fr) |
WO (1) | WO2011069202A1 (fr) |
ZA (1) | ZA201204182B (fr) |
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WO2021212171A1 (fr) * | 2020-04-24 | 2021-10-28 | 4 Farmers Australia Pty Ltd | Procédé de préparation d'une composition de glyphosate |
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BR112014021524B1 (pt) * | 2012-03-02 | 2022-11-29 | Basf Se | Método de preparação de grânulos emulsionáveis |
BR102018004761B1 (pt) * | 2018-03-09 | 2023-03-07 | Ouro Fino Química S.A. | Composição herbicia de glifosato de alta carga, formulação pronta para uso obtida a partir da composição e método para controlar várias espécies de plantas daninhas em culturas agrícolas |
WO2021091400A1 (fr) * | 2019-11-08 | 2021-05-14 | Donaghys Limited | Composition et procédés de fabrication et d'utilisation associés |
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BR0313970A (pt) * | 2002-08-31 | 2005-09-06 | Monsanto Technology Llc | Composições pesticidas contendo ácidos dicarboxìlicos |
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2010
- 2010-12-08 EP EP10835302.0A patent/EP2509425A4/fr not_active Withdrawn
- 2010-12-08 US US13/514,649 patent/US8852642B2/en active Active
- 2010-12-08 NZ NZ602144A patent/NZ602144A/xx active Application Filing
- 2010-12-08 AU AU2010330690A patent/AU2010330690B2/en active Active
- 2010-12-08 BR BR122017002517-1A patent/BR122017002517B1/pt active IP Right Grant
- 2010-12-08 EP EP17186191.7A patent/EP3278668A1/fr not_active Withdrawn
- 2010-12-08 WO PCT/AU2010/001663 patent/WO2011069202A1/fr active Application Filing
- 2010-12-08 CA CA2783484A patent/CA2783484C/fr active Active
- 2010-12-08 BR BR112012015773-6A patent/BR112012015773B1/pt active IP Right Grant
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WO2021212171A1 (fr) * | 2020-04-24 | 2021-10-28 | 4 Farmers Australia Pty Ltd | Procédé de préparation d'une composition de glyphosate |
Also Published As
Publication number | Publication date |
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US8852642B2 (en) | 2014-10-07 |
BR112012015773B1 (pt) | 2023-12-12 |
AU2010330690A1 (en) | 2011-09-15 |
NZ602144A (en) | 2013-11-29 |
CA2783484A1 (fr) | 2011-06-16 |
US20120302443A1 (en) | 2012-11-29 |
EP3278668A1 (fr) | 2018-02-07 |
ZA201204182B (en) | 2013-08-28 |
AU2010330690B2 (en) | 2011-10-06 |
EP2509425A4 (fr) | 2014-01-15 |
BR112012015773A2 (pt) | 2015-09-15 |
EP2509425A1 (fr) | 2012-10-17 |
CA2783484C (fr) | 2018-03-06 |
BR122017002517B1 (pt) | 2024-01-23 |
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