WO2011069202A1 - Nouvelle formulation de glyphosate - Google Patents

Nouvelle formulation de glyphosate Download PDF

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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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PCT/AU2010/001663
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English (en)
Inventor
Philip Pentland
Anthony Flynn
Abhinetiri Maharaj
Original Assignee
Eureka! Agresearch (Vic) Pty Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from AU2009905979A external-priority patent/AU2009905979A0/en
Application filed by Eureka! Agresearch (Vic) Pty Ltd filed Critical Eureka! Agresearch (Vic) Pty Ltd
Priority to BR112012015773-6A priority Critical patent/BR112012015773B1/pt
Priority to AU2010330690A priority patent/AU2010330690B2/en
Priority to BR122017002517-1A priority patent/BR122017002517B1/pt
Priority to EP10835302.0A priority patent/EP2509425A4/fr
Priority to US13/514,649 priority patent/US8852642B2/en
Priority to NZ602144A priority patent/NZ602144A/xx
Priority to CA2783484A priority patent/CA2783484C/fr
Publication of WO2011069202A1 publication Critical patent/WO2011069202A1/fr
Priority to ZA2012/04182A priority patent/ZA201204182B/en

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    • 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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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Toxicology (AREA)

Abstract

La présente invention concerne une formulation solide de glyphosate comprenant du glyphosate acide et comprenant en outre au moins un sel de glyphosate acceptable en agriculture, dans laquelle le glyphosate acide et l'au moins un sel de glyphosate sont en mélange et dans laquelle le rapport molaire du glyphosate acide aux fragments glyphosate totaux dans la formulation est d'au moins 10 %. La présente invention concerne en outre des procédés de préparation desdites formulations. La présente invention concerne en outre un procédé d'élimination des feuillages indésirables comprenant l'administration d'une forme diluée d'une formulation selon la présente invention.
PCT/AU2010/001663 2009-12-08 2010-12-08 Nouvelle formulation de glyphosate WO2011069202A1 (fr)

Priority Applications (8)

Application Number Priority Date Filing Date Title
BR112012015773-6A BR112012015773B1 (pt) 2009-12-08 2010-12-08 Formulação de glifosato, seu método de preparo e método de remoção de folhagem indesejada
AU2010330690A AU2010330690B2 (en) 2009-12-08 2010-12-08 Novel glyphosate formulation
BR122017002517-1A BR122017002517B1 (pt) 2009-12-08 2010-12-08 Formulação de glifosato, seu método de preparação, e método para remoção de folhagem indesejada
EP10835302.0A EP2509425A4 (fr) 2009-12-08 2010-12-08 Nouvelle formulation de glyphosate
US13/514,649 US8852642B2 (en) 2009-12-08 2010-12-08 Glyphosate formulation
NZ602144A NZ602144A (en) 2009-12-08 2010-12-08 Novel glyphosate formulation
CA2783484A CA2783484C (fr) 2009-12-08 2010-12-08 Nouvelle formulation de glyphosate
ZA2012/04182A ZA201204182B (en) 2009-12-08 2012-06-07 Novel glyphosate formulation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2009905979A AU2009905979A0 (en) 2009-12-08 Novel glyphosate formulation
AU2009905979 2009-12-08

Publications (1)

Publication Number Publication Date
WO2011069202A1 true WO2011069202A1 (fr) 2011-06-16

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Country Status (8)

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US (1) US8852642B2 (fr)
EP (2) EP3278668A1 (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)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021212171A1 (fr) * 2020-04-24 2021-10-28 4 Farmers Australia Pty Ltd Procédé de préparation d'une composition de glyphosate

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2013225065B2 (en) * 2012-03-02 2016-05-12 Basf Se Emulsifiable granule obtainable by mixing an pesticidal emulsion with solid dispersant and extruding the resulting paste
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
EP4054330A4 (fr) 2019-11-08 2023-12-27 Donaghys Limited Composition et procédés de fabrication et d'utilisation associés

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US5047079A (en) 1986-08-18 1991-09-10 Ici Americas Inc. Method of preparation and use of solid, phytoactive compositions
US5070197A (en) 1986-03-20 1991-12-03 Uniroyal Chemical Company, Inc. Dry reactive processing
WO1992012637A1 (fr) 1991-01-24 1992-08-06 Monsanto Company Formulations ameliorees a base de glyphosate
US5266553A (en) 1991-10-21 1993-11-30 Riverdale Chemical Company Method of manufacturing a dry water-soluble herbicidal salt composition
US5569639A (en) * 1992-02-07 1996-10-29 E. I. Du Pont De Nemours And Company Dry flowable agricultural compositions of glyphosate and sulfonylurea herbicides made without drying of the final product
US5633397A (en) 1995-06-07 1997-05-27 Monsanto Company Preparation of ammonium glyphosate via a gas-solid reaction system
US6475954B2 (en) * 2000-10-23 2002-11-05 Schirm Ag Solid glyphosphate-formulation and manufacturing process
WO2003013241A1 (fr) * 2001-08-03 2003-02-20 Nufarm Australia Limited Composition de glyphosate
US6881706B1 (en) 1999-02-24 2005-04-19 Akzo Nobel N.V. Use of a quaternary ammonium glycoside surfactant as an adjuvant for fertilizers or pesticides
WO2007143788A1 (fr) 2006-06-14 2007-12-21 Eureka Agresearch Pty Ltd Composition herbicide et procédé d'élimination de feuillage indésirable
US20080194409A1 (en) 2005-06-17 2008-08-14 Marco Bernardini Process for Preparing Ammonic Glyphosate Granules

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MXPA05002368A (es) 2002-08-31 2005-05-23 Monsanto Technology Llc Composiciones de pesticidas que contienen acidos dicarboxilicos.
US8133848B2 (en) * 2007-09-04 2012-03-13 Nufarm Americas Inc. Glyphosate composition and method of controlling weeds

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US5070197A (en) 1986-03-20 1991-12-03 Uniroyal Chemical Company, Inc. Dry reactive processing
US5047079A (en) 1986-08-18 1991-09-10 Ici Americas Inc. Method of preparation and use of solid, phytoactive compositions
WO1992012637A1 (fr) 1991-01-24 1992-08-06 Monsanto Company Formulations ameliorees a base de glyphosate
US5266553A (en) 1991-10-21 1993-11-30 Riverdale Chemical Company Method of manufacturing a dry water-soluble herbicidal salt composition
US5569639A (en) * 1992-02-07 1996-10-29 E. I. Du Pont De Nemours And Company Dry flowable agricultural compositions of glyphosate and sulfonylurea herbicides made without drying of the final product
US5633397A (en) 1995-06-07 1997-05-27 Monsanto Company Preparation of ammonium glyphosate via a gas-solid reaction system
US6881706B1 (en) 1999-02-24 2005-04-19 Akzo Nobel N.V. Use of a quaternary ammonium glycoside surfactant as an adjuvant for fertilizers or pesticides
US6475954B2 (en) * 2000-10-23 2002-11-05 Schirm Ag Solid glyphosphate-formulation and manufacturing process
WO2003013241A1 (fr) * 2001-08-03 2003-02-20 Nufarm Australia Limited Composition de glyphosate
US20080194409A1 (en) 2005-06-17 2008-08-14 Marco Bernardini Process for Preparing Ammonic Glyphosate Granules
WO2007143788A1 (fr) 2006-06-14 2007-12-21 Eureka Agresearch Pty Ltd Composition herbicide et procédé d'élimination de feuillage indésirable

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MICK CANAVAN: "Western Fann Express", 1 September 2007, UCCE FARM ADVISER SAN JOAQUIM COUNTY CALIF, article "Know your water quality in treating field bindweed"
See also references of EP2509425A4

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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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BR112012015773B1 (pt) 2023-12-12
CA2783484A1 (fr) 2011-06-16
EP2509425A1 (fr) 2012-10-17
CA2783484C (fr) 2018-03-06
US8852642B2 (en) 2014-10-07
AU2010330690A1 (en) 2011-09-15
AU2010330690B2 (en) 2011-10-06
EP2509425A4 (fr) 2014-01-15
ZA201204182B (en) 2013-08-28
BR122017002517B1 (pt) 2024-01-23
US20120302443A1 (en) 2012-11-29
NZ602144A (en) 2013-11-29
EP3278668A1 (fr) 2018-02-07
BR112012015773A2 (pt) 2015-09-15

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