WO2022204753A1 - Highly loaded florasulam formulations - Google Patents
Highly loaded florasulam formulations Download PDFInfo
- Publication number
- WO2022204753A1 WO2022204753A1 PCT/AU2022/050284 AU2022050284W WO2022204753A1 WO 2022204753 A1 WO2022204753 A1 WO 2022204753A1 AU 2022050284 W AU2022050284 W AU 2022050284W WO 2022204753 A1 WO2022204753 A1 WO 2022204753A1
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- WO
- WIPO (PCT)
- Prior art keywords
- florasulam
- formulation
- liquid
- volunteer
- crop
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 112
- 238000009472 formulation Methods 0.000 title claims abstract description 97
- 239000005529 Florasulam Substances 0.000 title claims abstract description 74
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 241000196324 Embryophyta Species 0.000 claims abstract description 42
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- 238000009331 sowing Methods 0.000 claims abstract description 29
- 239000007788 liquid Substances 0.000 claims abstract description 26
- 239000004480 active ingredient Substances 0.000 claims abstract description 24
- 239000005574 MCPA Substances 0.000 claims description 23
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
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- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 claims description 4
- MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 claims description 4
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- GINFBXXYGUODAT-UHFFFAOYSA-N flucarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F GINFBXXYGUODAT-UHFFFAOYSA-N 0.000 claims description 3
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- MUKYLHIZBOASDM-UHFFFAOYSA-N 2-[carbamimidoyl(methyl)amino]acetic acid 2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound NC(=N)N(C)CC(O)=O.OCC(O)C(O)C(O)C(O)C(O)=O MUKYLHIZBOASDM-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
Abstract
A liquid florasulam formulation has a florasulam concentration of above 200 g ai/L. The formulation may be a suspension concentrate (SC). The formulation preferably has florasulam as the sole active ingredient. The liquid florasulam formulation may have florasulam as the sole active ingredient, to provide flexibility of use. If desired, the formulation may be tank mixed with one or more other active ingredients before being apple to a crip or plant to control weeds. Surprisingly, the liquid florasulam formulation has been found to be effective when applied pre-sowing, alone or in a tank mix with other active ingredients.
Description
Highly Loaded Florasulam Formulations
Technical Field
The invention relates to novel florasulam formulations. In particular, the invention is concerned with highly loaded liquid florasulam formulations containing >200 g ai/L as a solo formulation or in a tank mixture with one or more active ingredients and applications of the same to control weeds.
Background Art
Florasulam (N-(2,6-Difluorophenyl)-8-fluoro-5-methoxy-[l,2,4]triazolo[l,5-c] pyrimidine-2-sulfonamide) is an acetolactate synthase (ALS) inhibitor herbicide suitable for the control of a wide range of weeds. It has been found to be particularly useful for the control of broadleaved weeds and is often used in winter cereals (wheat, barley, oats, triticale), corn and in fallow between crops. Use rates typically range between 2.5 to 7.5 g of florasulam per hectare.
Florasulam has been marketed by several suppliers globally as solo formulations or in tank mixtures or co-formulations with a wide range of other active ingredients including, for example: 2,4-D ester, 4-chloro-2-methylpenoxyacetic acid (MCPA), clopyralid, fluroxypyr, bifenox, pinoxaden, flucarbazone, halauxifen-methyl, diflufenican. However, the solo formulations currently available are generally low concentration liquid formulations with <50 grams of florasulam per litre. The co formulations or tank mixtures include similar low concentrations of florasulam in addition to one or more active ingredients e.g., as listed above. For example, co formulations with fluroxypyr or 2,4-D contain florasulam 2.5 g/L + fluroxypyr 100 g/L suspo-emulsion (SE), require relatively high use rates i.e., >1 L/ha. Others include florasulam 6.25 g/L + 2,4-D ester 300 g/L with a use rate of >500 mL/ha; or 50 g/L suspension concentrate (SC) solo formulation with a use rate of 50-100 mL/ha, usually tank mixed with another herbicide.
High concentration formulations are generally desirable: a highly loaded formulation can deliver the required quantity of active ingredient to a user in a smaller volume and lower weight. For formulators, higher concentration formulations reduce the quantity of formulated product to be produced. There is a saving in packaging, freight costs, storage volume and energy costs and a reduction of waste.
The only existing higher concentrated formulations are co-formulations like Paradigm® (florasulam 200 g/kg + halauxifen-methyl 200 g/kg water-dispersible granules (WG)). While this formulation requires relatively low use rates per hectare of formulated product, it cannot be applied without halauxifen-methyl as the partner. Further tank mixing with other active ingredients is limited e.g., particular recommendations are LVE (low-volatile ester) MCPA or clopyralid. However, such co-formulations like Paradigm® are not suitable in situations where halauxifen-methyl is not required, and these products do not provide flexibility nor the opportunity to apply florasulam solo at a lower use rate, or in a range of alternative combinations of florasulam and other active ingredients to control the spectrum of weeds present.
As such, higher loaded solo florasulam formulations are not currently available nor provided commercially and there is a need for providing such formulations. It would be desirable and beneficial to provide highly loaded florasulam formulations which have acceptable storage stability for effective use and dosing and which can be used as a solo formulation or in a mixture with a wider range of alternative other active ingredients to control a larger spectrum of weeds, as desired. Accordingly, there remains a need to develop such higher loaded florasulam formulations that are also commercially more desirable.
Reference to any prior art in the specification is not an acknowledgment or suggestion that this prior art forms part of the common general knowledge in any jurisdiction or that this prior art could reasonably be understood, regarded as relevant, and/or combined with other pieces of prior art by a skilled person in the art.
Summary of the Invention
The invention is broadly directed to highly loaded liquid florasulam formulations.
Accordingly, in one aspect of the present invention, there is provided a liquid florasulam formulation containing a florasulam concentration of above 200 g ai/L. In one example, the highly loaded liquid florasulam formulation according to the invention is a solo florasulam formulation comprising florasulam as the only active herbicide in the formulation.
It has been found that the ability to increase the maximum loading of florasulam in a liquid formulation above 200 g ai/L has the advantage over existing formulations prior to this invention by significantly reducing the volume of material to be formulated, transported and applied by the end user, respectively.
In preferred embodiments, the formulation according to the invention contains a florasulam concentration of more than 200 g ai/L, or at least B00 g ai/L, or at least 400 g ai/L, or at least 500 g ai/L, or about above 200 to about 500 g ai/L. In an example, the highly loaded liquid florasulam formulation according to the invention is tank mixed with one or more other active ingredients.
In another example, the highly loaded florasulam formulation according to the invention is applied to a crop or plant in a tank mixture optionally further comprising one or more other active ingredients. In yet another example, the highly loaded florasulam formulation according to the invention is applied pre-sowing, preferably being incorporated by sowing (IBS), alone or combined with one or more other active ingredients.
The one or more other active ingredients for use in a tank mix with the florasulam formulation according to the invention is preferably another herbicide. The herbicide will be readily selected by one skilled in the art according to the spectrum of weeds that it is desired to control. For example, the one or more other active ingredients is selected from the group consisting of: 2,4-D ester, 4-chloro-2-methylpenoxyacetic acid
(MCPA), clopyralid, fluroxypyr, bifenox, pinoxaden, flucarbazone, halauxifen-methyl,
diflufenican, picolinafen, bromoxynil, paraquat, glyphosate, and MEA glyphosate. Examples of commercially available herbicides containing one or more such active ingredients include Quadrant®, Spraytop® 250, WipeOut® Pro, Roundup Ultra®MAX, Weedmaster Argo, Weedmaster DST, Crucial 600 and Axial. It is contemplated that the florasulam formulation according to the invention may be any suitable liquid formulation. For example, the liquid formulation includes, but is not limited to, a suspension concentrate (SC), a suspo-emulsion (SE), an emulsion in oil or water, an emulsifiable concentrate (EC), a dispersible concentrate or an oil dispersion. Preferably, the florasulam formulation according to any aspect, embodiment or example of the invention is an SC.
The florasulam formulation of the invention is useful for controlling a large spectrum of weeds that are susceptible to florasulam and/or the one or more other active ingredients, if present.
Accordingly, in another aspect of the present invention there is provided a method for controlling weeds comprising applying the liquid florasulam formulation according to the invention to a crop or plant and/or in fallow between crops to control the weeds. One skilled in the art would readily be able to select a suitable crop or plant that would benefit from this application. For example, the suitable crop or plant includes, but is not limited to, wheat, barley, oats, cereal rye, triticale and corn. In this aspect, the use of a solo or tank application of the florasulam formulation of the invention may be readily selected by one skilled in the art according to the weeds it is desired to control.
In one example, the application of the florasulam formulation according to the invention is at a rate of less than 25 mL/ha, or about 5 to 10 mL/ha, or about 12.5 to 25 mL/ha. In one example, the florasulam formulation according to the invention is applied with an adjuvant suitable for greater leaf absorption and efficacy. For example, the adjuvant is an oil adjuvant such as commercially available adjuvants such as, Uptake® Spray or Adigor®. Other adjuvants may also be suitable.
As used herein, except where the context requires otherwise, the term "comprise" and variations of the term, such as "comprising", "comprises and "comprised", are not intended to exclude further additives, components, integers or steps.
Further aspects of the present invention and further embodiments of the aspects described in the preceding paragraphs will become apparent from the following description, given by way of embodiments and/or examples.
Detailed Description of Preferred Embodiments
Reference will now be made in detail to certain embodiments of the invention. While the invention will be described in conjunction with the embodiments and/or examples, it will be understood that the intention is not to limit the invention to those embodiments/examples. On the contrary, the invention is intended to cover all alternatives, modifications, and equivalents, which may be included within the scope of the present invention.
One skilled in the art will recognize many methods and materials similar or equivalent to those described herein, which could be used in the practice of the present invention. The present invention is in no way limited to the methods and materials described. It will be understood that the invention disclosed and defined in this specification extends to all alternative combinations of two or more of the features mentioned or evident from the text. All of these different combinations constitute various alternative aspects of the invention.
For the purposes of interpreting this specification, terms used in the singular will also include the plural and vice versa.
Example 1: Highly Loaded Florasulam Formulations.
By way of example, a highly loaded aqueous SC formulation containing a florasulam concentration of more than200g/L was prepared. The components are as set out in Table 1:
Table 1: Components
Details of the components are as set out in Table 2:
Table 2: Component Details
To prepare the formulation, by way of example, the following method and the sequence of operations were followed:
1. 60% of the water was charged into a suitable vessel equipped with high shear saw tooth dispersion blade mixer.
2. Mixing was commenced and 50% of the Gensil 2030 was added.
3. Mixing was maintained and Citric Acid was added.
4. Mixing was maintained and Tersperse 4894 was added.
5. Mixing was maintained and Tersperse 2500 was added.
6. Mixing was maintained and Attagel 50 was added.
7. Mixing was maintained and Florasulam Technical was gradually incorporated. The mixture was dispersed until homogenous and free from agglomerates.
8. Recirculation milling was commenced using a Dyno-Mill KD or similar bead mill. The mill temperature was maintained below 35 °C.
9. The mill base was ground until a particle size D (v, 0.5) 3.0 - 5.0 microns and D (v, 0.9) < 15 micron was achieved as determined by CIPAC MT 187.
10. The mill base was transferred to another suitable vessel equipped with a propeller type stirrer. Agitation was maintained at all times. 11. The remaining Gensil 2030 and the remaining water were added.
12. The Glycerine, less the portion for premix (see 13) with Xanthum Gum TSFT, was added.
13. A premix was prepared by mixing a suitable portion of Glycerine with the Xanthum Gum TSFT and Proxel GXL in a separate vessel. This premix was then added to the mill base and agitation was continued until the xanthum gum was completely hydrated and dispersed.
14. The product was examined according to the specification and adjustments were made as required.
The resultant highly loaded SC formulation containing a florasulam concentration of more than 200 g/L, identified as AD-AU-1826 SC formulation, was analysed as described further below. The analysis is in Table 3:
Table 3: Analysis
Packaging Stability
A sample of the product in HDPE was weighed and then maintained at 54 °C for a period of 14 days. Table 4: Analysis of Packaging Stability in HDPE
The formulation was suitable for packaging in a HDPE container with a screw cap closure. The meaning of each of Tol and TASI in Table 4 (above) is explained below.
Analysis Methods
The relevant test parameters for suspension concentrate (SC) formulations may be found in Section S.2 Table 25 of the Australian Pesticides & Veterinary Medicines Authority (APVMA) Guidelines for the Generation of Storage Stability Data for Agricultural Chemical Products (Version 2, 22 July 2015). An outline summary of each method employed follows:
Appearance, Physical State & Colour
These tests were performed visually and are described in descriptive terms.
Odour This test was performed organoleptically and involves the use of descriptive terms. Density MT S. S.2
A portion of sample was accurately weight into a density bottle and diluted with water containing an anti-foam agent, using vacuum, if necessary, to remove occluded air. The volume of sample taken was then found by making up to capacity with the anti-foam solution and weighing. pH Collaborative International Pesticides Analytical Council (CIPAC) MT 75.3
The pH value of a 1% v/v dilution of the formulation was determined by means of a pH meter and electrode system
- Brookfield RV Viscosity CIPAC MT 192 The viscosity of the formulation was measured in a standard measuring system using a Brookfield RV Viscometer
Spontaneity of dispersion CIPAC MT 160
The method was broadly similar to that used to determine suspensibility (CIPAC MT 184), except that the preparation of the suspension of known concentration employs only one inversion and a 5 min standing time. The top 9/10ths were then drawn off and the remaining 1/lOth was then assayed chemically and the spontaneity of dispersion calculated.
Suspensibility CIPAC MT 184
A suspension of known concentration in CIPAC Standard Water was prepared, placed in a prescribed measuring cylinder at a constant temperature, and allowed to remain undisturbed for a specific time (30 minutes). The top 9/10ths were then drawn off and the remaining 1/lOth was then assayed chemically and the suspensibility calculated.
- Wet Sieve Test Cl PAC MT 185
A sample of the formulation was dispersed in water and the suspension formed was transferred to a sieve and washed. The amount of the material retained on the sieve was determined by drying and weighing. Persistent Foam CIPAC MT 47.2
The sample was diluted in a measuring cylinder of standard dimensions which was inverted 30 times and the amount of foam created and remaining after certain times was measured.
Cold Temperature Stability of Liquid Formulations CIPAC MT 39.3 A sample was maintained at 0 ± 2 °C for 7 days and the nature and quantity of any separated material retained following wet sieving through a 75 pm sieve was determined.
Active Constituent Content - QChem Laboratories Analytical Method QCM-
174.02 Florasulam content was determined by reversed phase high performance liquid chromatography using UV detection and external standardisation. The method was appropriately validated as per the APVMA Guidelines for the Validation of Analytical Methods for Active Constituents and Agricultural Products (Revision 1, July 1 2014).
Observation of Packaging Stability A sample of the product in a container of the same material and construction to that of the marketed product was weighed and then maintained at 54 °C for a period of 14
days. Any loss or gain in weight was recorded and the container examined, recording observations of any significant interaction with the formulation.
Storage Stability Methods
The APVMA Guidelines for the Generation of Storage Stability Data for Agricultural Chemical Products (Version 2, 22 July 2015) gives a comprehensive guide to the conduct of stability testing for agricultural chemical products. The procedures contained therein were followed to prepare ambient temperature, elevated temperature (accelerated stability) and cold temperature storage samples as follows:
5000 mL of highly loaded florasulam SC was formulated. Two 1000 mL specimens were packaged into HDPE containers with screw cap closure (commercial packaging material). The specimens remained in their containers and were stored in an air- conditioned facility at approximately 21 °C for the period prior to ambient temperature and elevated temperature storage.
On the day of initiation of the accelerated storage trial, each of the specimens in their unopened containers were weighed on a top pan balance (Mettler PJS600 Delta Range: SNR J29589) to determine a starting weight (for use as a comparison with weights at the conclusion of the storage period).
The specimen designated for elevated temperature storage (Accelerated Stability sample TASI) was placed into a thermostatically controlled oven (VWR Mini Incubator: SNR 0811V1169), heated to 54 ± 2 °C, for a period of 14 days. At the end of this period, the sample was removed from the oven and placed into a desiccation chamber to allow cooling to ambience.
The remaining formulation specimen (Time Zero sample Tol) was stored at air- conditioned ambient temperatures (~21 °C) in a locked cabinet for the duration of the elevated temperature storage period.
A sample of the formulation was prepared for low temperature stability testing by placing 100 mL of the post accelerated storage stability formulation specimen (TASI) into 100 mL ASTM D96 graduated centrifuge tubes and storing it in a refrigerated
cabinet (Esatto Model EBF93W: SNR 5G386) at a temperature of 0 ± 2° C for a total of 7 days.
The storage stability samples of AD-AU-1826 SC formulation were analysed as described above and the results are as follows: Analyses obtained for Time Zero (Ambient) sample Tol of AD-AU-1826 SC are as provided in Table 5 below.
Table 5: Analysis of Time Zero (Ambient) Sample Tol of AD-AU-1826 SC
Analyses obtained for Accelerated Stability sample TASI of AD-AU-1826 SC are as provided in Table 6 below.
Table 6: Analysis of Accelerated Stability Sample TASI of AD-AU-1826 SC
The AD-AU-1826 SC formulation was determined to be stable to heat for 2 weeks at 54°C for all parameters according to the standard CIPAC accelerated testing regime and therefore is expected to be shelf stable for at least 2 years.
Cold Temperature Stability of Liquid Formulations CIPAC MT 39.3 The AD-AU-1826 SC formulation was subjected to cold storage condition at 0 ± 2 °C for 7 days and the volume and nature of any separated material was recorded. Analyses obtained for Cold Stability sample TCDI of AD-AU-1826 SC are as provided in Table 7 below.
Table 7: Analysis of Cold Stability sample TCDI of AD-AU-1826 SC
The absence of any separation or crystal growth indicates the formulation to be cold storage stable.
In conclusion, the new AD-AU-1826 SC formulation containing a florasulam concentration of above 200 g/L performs excellently in all requisite tests.
A highly loaded aqueous SC formulation containing a florasulam concentration of about 500g/L, identified as AD-AU-1818-SC, was also prepared and analysed using similar methods to those described above.
Analyses obtained for Time Zero (Ambient) sample Tol and for Accelerated Stability sample TASI of AD-AU-1818-SC are as provided in Table 8 and Table 9 below.
Table 8: Analysis of Time Zero (Ambient) Sample Tol of AD-AU-1818-SC
Table 9: Analysis of Accelerated Stability Sample TASI of AD-AU-1818-SC
The AD-AU-1818 SC formulation was determined to be stable to heat for 2 weeks at
54°C for all parameters according to the standard CIPAC accelerated testing regime.
In conclusion, the inventors have created a novel higher loaded liquid florasulam formulation containing a florasulam concentration above that of currently available formulations. In this example, the ability to increase the maximum loading in a liquid formulation from 50 g ai/L to more than 200 to about 500 g/L represents a 75 to 90%
reduction in the volume of material to be formulated, transported and applied by the end user, respectively. The solo liquid florasulam SC formulations are more versatile than existing co-formulated products such as Paradigm®, as they can be applied on susceptible weeds or pre-sowing without additional herbicides that are co-formulated or without an additional tank mix partner or adjuvant.
Example 2: Compatibility Profile of Highly Loaded Florasulam SC Formulations
Compatibility tests were conducted to evaluate the suitability of using the highly loaded liquid florasulam formulation of Example 1, identified as AD-AU-1826 SC, with additional herbicides containing one or more other active ingredients along with adjuvants as tank mix partners. The compatibility profile of AD-AU-1826 are provided in Table 10 below.
Table 10: Compatibility Profile of AD-AU-1826
Adjuvants
Uptake® : paraffinic oil and alkoxylated alcohol non-ionic surfactants. Adigor®: methyl esters of canola oil fatty acids.
Other Herbicides (active ingredients) Spraytop® 250: paraquat.
Spraytop® 330: paraquat.
Quadrant®: picolinafen, diflufenican, bromoxynil, MCPA.
WipeOut® Pro: glyphosate present as MEA salt.
Roundup Ultra®MAX: high-load glyphosate. Weedmaster Argo: glyphosate present as the potassium and isopropylamine salts.
Weedmaster DST: glyphosate present as the potassium and mono ammonium salts.
Crucial 600: glyphosate.
Axial: pinoxaden + cloquintocet-mexyl.
Example 3: Field Tests
Field Trials analyses were conducted to evaluate the efficacy of the highly loaded florasulam SC formulations of Example 1, identified as AD-AU-1826 SC (>200 g ai/L).
Field Test 1: Roseworthy, South Australia
At Roseworthy, SA, a trial was conducted to evaluate the crop safety and efficacy of AD-AU-1826 SC (200 g ai/L) for the pre-emergent control of volunteer lentils (Lens culinaris), volunteer field pea ( Pisum sativum arvense ) and volunteer chickpea ( Cicer arietnum) in wheat cv. Other products were also tested. The product details are in Table 11:
Table 11: Products
Treatments are set out in Table 12:
Table 12: Treatments
IBS = Treatments incorporated by sowing
PSPE = Treatments applied post sowing, pre-emergent
Mean crop emergence of wheat is shown in Table IB:
Table 13. Crop emergence of wheat cv.
IBS = Treatments incorporated by sowing
PSPE = Treatments applied post sowing, pre-emergent
DAS = Days after sowing
NSD = No significant difference due to a P-value > 0.05
Percent volunteer lentil control is shown in Table 14:
Table 14: Volunteer lentil ( Lens culinaris) control in wheat cv
IBS = Treatments incorporated by sowing PSPE = Treatments applied post sowing, pre-emergent DAS = Days after sowing
* = Data failed Bartlett's test and cannot be transformed for homogeneity Means followed by the same letter are not significantly different (P = 0.05, Duncan's) tA = Data transformed using x = Arcsine square root percent (y), original means presented
Mean percent field pea control is shown in Table 15:
Table 15: Volunteer field pea ( Pisum sativum arvense) control in wheat cv
IBS = Treatments incorporated by sowing
PSPE = Treatments applied post sowing, pre-emergent
DAS = Days after sowing
Means followed by the same letter are not significantly different (P = 0.05, Duncan's) tA = Data transformed using x = Arcsine square root percent (y), original means presented
Mean field pea density is shown in Table 16: Table 16: Volunteer field pea ( Pisum sativum arvense) density in wheat cv
IBS = Treatments incorporated by sowing
PSPE = Treatments applied post sowing, pre-emergent
DAS = Days after sowing
Means followed by the same letter are not significantly different (P = 0.05, Duncan's) tL = Data transformed using x = Log (y + 1), original means presented
Mean percent chickpea control is shown in Table 17:
Table 17: Volunteer chickpea ( Cicer arietinum) control in wheat cv
IBS = Treatments incorporated by sowing
PSPE = Treatments applied post sowing, pre-emergent DAS = Days after sowing
* = Data failed Bartlett's test and cannot be transformed for homogeneity Means followed by the same letter are not significantly different (P = 0.05, Duncan's) tA = Data transformed using x = Arcsine square root percent (y), original means presented
Chickpea density in wheat is shown in Table 18:
Table 18: Volunteer chickpea ( Cicer arietinum) density in wheat cv
IBS = Treatments incorporated by sowing
PSPE = Treatments applied post sowing, pre-emergent DAS = Days after sowing
Means followed by the same letter are not significantly different (P = 0.05, Duncan's)
NSD = No significant difference due to a P-value > 0.05 tL = Data transformed using x = Log (y + 1), original means presented Moderate crop vigour reductions were recorded for AD-AU-1826 applied at 5 g ai/ha standalone IBS and PSPE.
AD-AU-1826 treatments applied standalone IBS recorded equivalence in control of volunteer lentil (Lens culinaris), volunteer field pea (Pisum sativum arvense) and volunteer chickpea (Cicer arietinum). Callisto and Victory recorded significantly lower volunteer lentil densities compared to the untreated control. However, these were not always lower than other treatments.
Treatments containing AD-AU-1826 applied standalone IBS recorded equivalent and significant reductions in volunteer field pea densities compared to the untreated control. Accordingly, standalone AD-AU-1826 performed well.
Applying AD-AU-1826 IBS at 3 g ai/ha and 5 g ai/ha significantly reduced volunteer field pea densities compared to the same active ingredient rate applied PSPE.
AD-AU-1826 treatments applied standalone IBS and PSPE were equivalent for volunteer chickpea (Cicer arietinum) density. Field Test 2: Elmore, Victoria
At Elmore, Victoria, a trial was conducted in wheat Triticum aestivum cv. to: compare the equivalence on volunteer pulses of AD-AU-1826 + fluroxypyr ± Victory with Outshine ± Victory; compare the bioequivalence of Vortex and AD-AU-1826 + 2,4-D ester 680; - evaluate AD-AU-1826 when applied with other tank mix partners including LVE
MCPA 570, Zulu XT or Triathlon; compare with another registered standard product, Paradigm + LVE MCPA 570; determine the crop safety of all treatments on cereals.
Herbicide treatments were applied by gas powered hand boom at Zadocks (Z) 13/22- 14/23 crop growth stage (GS). Herbicide treatments were applied across the direction of sowing with a three metre width handheld propane powered spray boom.
A mixed volunteer pulse weed complex was targeted comprising: faba bean Viciafaba at 2-3 nodes/leaf pairs GS (UTC mean 12 plants/m2); tame vetch Vicia sativa at 3-5 nodes/leaflets GS (UTC mean 27 plants/m2); - field pea Pisum sativum at 3-5 nodes GS (UTC mean 14 plants/m2); spineless burr medic Medicago polymorpha cv. Cavalier at 3-5 trifoliate leaves GS (UTC mean 11 plants/m2).
Volunteer pulse seeds were spread evenly along trial replicates prior to crop sowing.
Treatments are set out in Table 19:
Table 19: Treatments
Crop safety and volunteer pulse efficacy of trial treatments were assessed at 15 DAA, 43 DAA and grain yield was assessed at 126 DAA.
AD-AU-1826 tank-mixes with fluroxypyr ± Victory compared to Outshine ± Victory gave equivalent final efficacy comprising commercially acceptable control of volunteer pulses.
AD-AU-1826 tank-mix with fluroxypyr + Victory gave significantly higher efficacy of faba bean, vetch and field-pea at second assessment compared to Outshine + Victory tank-mix. Vortex & AD-AU-1826 tank-mixes with 2,4-D ester 680, LVE MCPA 570, Zulu XT & Triathlon all gave equivalent efficacy comprising commercially acceptable control of volunteer pulses at final assessment.
Commercial standard treatment of Paradigm + LVE MCPA 570 gave commercially acceptable control of all volunteer pulses at final assessment. Triathlon applied alone gave control of faba bean and burr medic, borderline commercially acceptable control of tame vetch and weak suppression of field peas.
All treatments gave excellent wheat crop safety.
Field Test 3: Bridgewater, Victoria
At Bridgewater Victoria, a trial was conducted in wheat in oats Avena sativa cv. to: - compare the equivalence on fumitory and hedge mustard of AD-AU-1826 + fluroxypyr + LVE MCPA with Outshine + LVE MCPA;
evaluate AD-AU-1826 when applied with other tank mix partners including Affinity + MCPA 750, Quadrant or Triathlon; compare with another registered standard product, Paradigm & Precept; and determine the crop safety of all treatments on oats. Herbicide treatments were applied by gas powered hand boom at the Zadocks (Z) 23- 25 crop growth stage.
There was a moderate density weed complex at application comprising:
Indian hedge mustard Sisymbrium orientale at 2-5 leaf G.S. (UTC mean 27 plants/m2); - denseflower fumitory Fumaria densiflora at 6-20 leaf G.S. (UTC mean 28 plants/m2); volunteer sub-clover Trifolium subterraneum, at 2-7 trifoliate leaf G.S. (UTC mean 61 plants/m2); and wireweed Polygonum aviculare at 2-6 leaf G.S. (UTC mean 12 plants/m2). Prior barley crop stubble groundcover was minimal (=5%) due to very poor crop germination and subsequent maintenance as chemical fallow over the 2018 season. Sub-clover was established uniformly across the site by seeding with a separate shallow sowing pass to the oat crop.
Treatments are set out in Table 20. Table 20: Treatments
Crop safety and weed efficacy of trial treatments were assessed at 12 DAA, 18 DAA, 31 DAA and 87 DAA and plant counts were done.
Trial data was analysed using a 95% confidence level. Means were compared using Duncan's New Multiple Range Test. AD-AU-1826 + fluroxypyr + LVE MCPA 570 gave commercially acceptable control of
Indian hedge mustard, denseflower fumitory and sub-clover, equivalent to matched rates of Outshine + LVE MCPA 570.
AD-AU-1826 + Affinity Force + MCPA 750 gave equivalent, commercially acceptable control of Indian hedge mustard and denseflower fumitory, compared to Affinity Force + MCPA 750.
AD-AU-1826 + Affinity Force + MCPA 750 gave significantly higher, commercially acceptable control of sub-clover compared to Affinity Force + MCPA 750 which gave strong suppression.
AD-AU-1826 tank-mixes with Triathlon and Quadrant gave improved mean efficacy against denseflower fumitory compared to Triathlon and Quadrant applied alone, lifting efficacy from good to very strong suppression.
AD-AU-1826 tank-mixes with Triathlon and Quadrant gave significantly improved efficacy against sub-clover, lifting efficacy from good suppression to commercially acceptable control. Paradigm gave excellent control of Indian hedge mustard, denseflower fumitory and sub-clover.
Precept gave excellent control of Indian hedge mustard and denseflower fumitory and suppression of sub-clover.
All treatments were safe to the crop. AD-AU-1826 applied alone always gave greater crop biomass reduction with some differences statistically separated, compared to when applied in tank-mixes.
Paradigm and AD-AU-1826 applied alone gave similar biomass reduction.
Field Test 4: Greymare, Queensland
Post-emergence control of Mexican poppy in winter cereals has relied upon 2,4-D and more recently upon Paradigm + MCPA.
A field trial was conducted at Jandowae, QLD to compare a 25 mL/ha AD-AU-1826 in combination with LVE MCPA, LVE MCPA + Flagship, LVE 2,4-E ester 680, Zulu XT,
Triathlon, Bronco MA-X, Flagship 400 + LVE 2,4-D ester 680 and Bronco MA-X + Flagship. Finally, the experiment had the objective of determining the crop safety of the various treatments in oats cv. Warrego.
Treatments were applied using a hand-held spray boom equipped with 4 x HMD green low-pressure air-induction nozzles and operated at a pressure of 250 kPa to deliver a spray volume of 100 L/ha in dryland oats at GS 23 to 27 under conditions of good soil moisture. Treatments were arranged in a Randomized Complete Block Design with a plot size of 2 x 10 metres and 4 replicates.
Soil type was a pebbly sandy clay loam. The weed spectrum was dominated by Mexican poppy and wireweed with lower numbers of small-flowered mallow, sowthistle and pimpernel.
Weed and crop details at application are summarised in Table 21:
Table 21: Weed Details
Treatments are summarised in Table 22:
Table 22: Treatments
L applied with 0.5% v/v Uptake Spraying Oi LL applied with 0.2% v/v Wetspray
Weed control was assessed on 4 occasions using a subjective 0-100 percentage scale where 0=no effect and 100=complete control. Assessments were undertaken August 4
(7 DAA), August 11 (14 DAA), August 25 (29 DAA) and September 21 (55 DAA). Crop Safety was assessed on August 4 and 11 with a subjective % estimate of injury where 0=no effect and 100=complete crop destruction.
Data was analysed at a Randomized Complete Block separately for each crop using ARM 9 statistical software. AOV tables were prepared with treatment values identified by different letters being significant according to the Duncan's New Multiple Range test at the 5% level of probability.
Percent control of Mexican Poppy is shown in Table 23.
Table 23: Percent Control of Mexican Poppy
Treatments separated by different letters are significantly different at the 5% level of probability
L plus 0.5% v/v Uptake LL plus 0.2% v/v Wetspray Percent control of wireweed is shown in Table 24:
Table 24: Percent Control of Wireweed
Treatments separated by different letters are significantly different at the 5% level of probability
A plus 0.5% v/v Uptake AA plus 0.2% v/v Wetspray Commercially acceptable control of Mexican poppy was achieved with Bronco MA-X alone and in combination with AD-AU-1826 and AD-AU-1826 + LVE MCPA.
Commercially acceptable control of Mexican poppy was achieved with AD-AU-1826 in combination with LVE MCPA 570 +- Flagship 400, 2,4-D LVE ester 680 +/- Flagship 400, Triathlon and AD-AU-1826 + Flagship + 500 mL/ha Bronco MA-X. Excellent control of wireweed was obtained with AD-AU-1826 + Triathlon.
Treatments including Triathlon caused unacceptable injury to oats.
It is apparent from the Field Tests that the formulation of the invention may be used to control one or more weeds chosen from: volunteer lentils (Lens culinaris), volunteer field pea ( Pisum sativum arvense), volunteer chickpea ( Cicer arietnum), faba bean (Vicia faba), tame vetch (Vicia sativa), spineless burr medic (Medicago polymorpha cv. Cavalier), Indian hedge mustard (Sisymbrium orientale), denseflower fumitory ( Fumaria densiflora), volunteer sub-clover (Trifolium subterraneum), wireweed
(Polygonum aviculare), Mexican poppy (Argemone Mexicana) and small-flowered mallow (Malva pa rvi flora).
Other weeds which may also be controlled by the formulation of the invention include: Bedstraw ( Galium tricornutum), Turnip weed (Rapistrum rugosum), Bittercress (Coronopus didymus), Wild radish (Raphanus raphanistrum), Wild turnip (Brassica tournefortii), Shepherd's purse (Bidens Pilosa), Stonecrop (Crassula sieberiana, C. helsii), Annual Ground Cherry, Wild Gooseberry (Physalis spp.), Thornapples (Datura spp.), Apple of Peru (Nicandra physalodes), Bathurst Burr (Xanthium spinosum), Noogoora Burr (Xanthium strumarium), Doublegee/Spiny emex (Emex australis), Caltrop/ Yellow Vine including (T. maximus and T. micrococcus), Cleavers (Galium aparine), Dwarf amaranth (Amaranthus macrocarpus), Prickly lettuce (Latuca serriola), Polymeria (Polymeria pusillia), Capeweed (Arctotheca calendula), Rynchosia (Rynchosia minima), Volunteer sunflowers, Pigweed (Portulaca olraceae), Sowthistle (Sonchus oleraceus), Variegated thistle (Silybum marianum), Vetch Tares (Vicia villosa), volunteer lupins, Climbing buckwheat/ Black bindweed (Fallopia convolvulus), Saffron thistle (Carthamus lanatus), New Zealand spinach (Tetragonia tetragonioides), Skeleton weed (Chondrilla juncea), Rough poppy (Papaver hybridum), Erodium/ Common Storks Bill (Erodium cicutarium), Volunteer conventional/ triazine tolerant canola (Brassica napus), Silverleaf Nightshade (Solanum elaeagnifolium), Bellvine (Ipomea plebeia), Bladder Ketmia and Cowvine.
Industrial Applicability
It will be appreciated from the data in the above tables that the efficacy of the formulations of the invention is at least comparable to that of prior art formulations. However, the formulations of the invention, being more concentrated, are more efficient. As a solo formulation, the formulations of the invention are more flexible.
Claims
Claims
1. A liquid florasulam formulation containing a florasulam concentration of above 200 g ai/L
2. The liquid florasulam formulation of claim 1, wherein florasulam is the sole active ingredient in the formulation.
3. The liquid florasulam formulation of claim 1 or 2, wherein the florasulam concentration is chosen from: about 205 g ai/L, about 300 g ai/L, about 400 g ai/L and about 500 g ai/L.
4. The liquid florasulam formulation of any one of claims 1 to 3, wherein the formulation is chosen from: a suspension concentrate (SC), a suspo-emulsion
(SE), an emulsion in oil or water, an emulsifiable concentrate (EC), a dispersible concentrate and an oil dispersion.
5. The liquid florasulam formulation of claim 4 which is a suspension concentrate (SC). 6. The liquid florasulam formulation of any one of claims 1 to 5 in a tank mix with one or more other active ingredients.
7. The liquid florasulam formulation of claim 6 wherein the one or more other active ingredients is selected from the group consisting of: 2,4-D ester, 4- chloro-2-methylpenoxyacetic acid (MCPA), clopyralid, fluroxypyr, bifenox, pinoxaden, flucarbazone, halauxifen-methyl, diflufenican, picolinafen, bromoxynil, paraquat, glyphosate, and MEA glyphosate.
8. A method for controlling weeds comprising applying the liquid florasulam formulation according to any one of claims 1 to 7 to a crop or plant and/or in fallow between crops to control the weeds. 9. The method of claim 8, wherein the liquid florasulam formulation is applied to a crop area by being incorporated by sowing of the crop.
10. The method of claim 8, wherein the liquid florasulam formulation is applied to the plant or crop post sowing but pre-emergently.
11. The method of claim 8, wherein the liquid florasulam formulation is applied to the plant or crop post-emergently. 12. The method of any one of claims 8 to 11, wherein the weeds are chosen from: volunteer lentils (Lens culinaris), volunteer field pea ( Pisum sativum arvense), volunteer chickpea ( Cicer arietnum), faba bean (Vicia faba), tame vetch ( Vida sativa), spineless burr medic (Medicago polymorpha cv. Cavalier), Indian hedge mustard (Sisymbrium orientale), denseflower fumitory ( Fumaria densiflora), volunteer sub-clover (Trifolium subterraneum), wireweed (Polygonum aviculare), Mexican poppy (Argemone Mexicana) and small-flowered mallow (Malva parviflora), Bedstraw (Galium tricornutum), Turnip weed (Rapistrum rugosum), Bittercress (Coronopus didymus), Wild radish (Raphanus raphanistrum), Wild turnip (Brassica tournefortii), Shepherd's purse (Bidens Pilosa), Stonecrop (Crassula sieberiana, C. helsii), Annual Ground Cherry, Wild Gooseberry (Physalis spp.), Thornapples (Datura spp.), Apple of Peru (Nicandra physalodes), Bathurst Burr (Xanthium spinosum), Noogoora Burr (Xanthium strumarium), Doublegee/Spiny emex (Emex australis), Caltrop/ Yellow Vine including (T. maximus and T. micrococcus), Cleavers (Galium aparine), Dwarf amaranth (Amaranthus macrocarpus), Prickly lettuce (Latuca serriola), Polymeria (Polymeria pusillia), Capeweed (Arctotheca calendula), Rynchosia (Rynchosia minima), Volunteer sunflowers, Pigweed (Portulaca olraceae), Sowthistle (Sonchus oleraceus), Variegated thistle (Silybum marianum), Vetch Tares (Vicia villosa), volunteer lupins, Climbing buckwheat/ Black bindweed (Fallopia convolvulus), Saffron thistle (Carthamus lanatus), New Zealand spinach (Tetragonia tetragonioides), Skeleton weed (Chondrilla juncea), Rough poppy (Papaver hybridum), Erodium/ Common Storks Bill (Erodium cicutarium), Volunteer conventional/ triazine tolerant canola (Brassica napus), Silverleaf Nightshade (Solanum elaeagnifolium), Bellvine (Ipomea plebeia), Bladder Ketmia and Cowvine.
IB. The method of any one of claims 8 to 12, wherein the liquid florasulam formulation is applied at a rate of about 25 mL/ha or less.
14. The method of claim 13, wherein the liquid florasulam formulation is applied at a rate of about 5 to 10 mL/ha. 15. The method of claim 13, wherein the liquid florasulam formulation is applied at a rate of about 12.5 to 25 mL/ha.
16. The method of any one of claims 8 to 15, wherein the crop or plant is chosen from: wheat, barley, oats, cereal rye, triticale and corn.
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| AU2022252064A AU2022252064A1 (en) | 2021-03-29 | 2022-03-29 | Highly loaded florasulam formulations |
| CA3214009A CA3214009A1 (en) | 2021-03-29 | 2022-03-29 | Highly loaded florasulam formulations |
| IL307389A IL307389A (en) | 2021-03-29 | 2022-03-29 | Highly loaded florasulam formulations |
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| WO2023031810A1 (en) * | 2021-09-03 | 2023-03-09 | Rotam Agrochem International Company Limited | Crystalline form of florasulam, preparation and use of the same |
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|---|---|---|---|---|
| WO1999048359A1 (en) * | 1998-03-20 | 1999-09-30 | Dow Agrosciences Llc | Pesticidal adjuvants |
| WO2013082016A1 (en) * | 2011-11-30 | 2013-06-06 | Dow Agrosciences Llc | Stable suspoemulsions comprising a plurality of agriculturally active ingredients |
| CN106472529A (en) * | 2016-08-31 | 2017-03-08 | 四川利尔作物科学有限公司 | Herbicidal combinations and its application |
| CN107361069A (en) * | 2016-05-11 | 2017-11-21 | 海利尔药业集团股份有限公司 | A kind of Synergistic herbicide compositions |
| CN108849870A (en) * | 2018-06-22 | 2018-11-23 | 河北威远生物化工有限公司 | Bentazone and florasulam Synergistic herbicide compositions and its dispersible oil-suspending agent |
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| CN102972418B (en) * | 2012-12-25 | 2014-10-15 | 联保作物科技有限公司 | Florasulam water dispersible granules and preparation method thereof |
| CN105557717B (en) * | 2016-03-03 | 2018-08-03 | 江苏丰山集团股份有限公司 | A kind of florasulam suspending agent and preparation method thereof |
| CN111194167A (en) * | 2017-10-10 | 2020-05-22 | 美国陶氏益农公司 | Preparation method of florasulam |
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- 2022-03-29 WO PCT/AU2022/050284 patent/WO2022204753A1/en active Application Filing
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999048359A1 (en) * | 1998-03-20 | 1999-09-30 | Dow Agrosciences Llc | Pesticidal adjuvants |
| WO2013082016A1 (en) * | 2011-11-30 | 2013-06-06 | Dow Agrosciences Llc | Stable suspoemulsions comprising a plurality of agriculturally active ingredients |
| CN107361069A (en) * | 2016-05-11 | 2017-11-21 | 海利尔药业集团股份有限公司 | A kind of Synergistic herbicide compositions |
| CN106472529A (en) * | 2016-08-31 | 2017-03-08 | 四川利尔作物科学有限公司 | Herbicidal combinations and its application |
| CN108849870A (en) * | 2018-06-22 | 2018-11-23 | 河北威远生物化工有限公司 | Bentazone and florasulam Synergistic herbicide compositions and its dispersible oil-suspending agent |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023031810A1 (en) * | 2021-09-03 | 2023-03-09 | Rotam Agrochem International Company Limited | Crystalline form of florasulam, preparation and use of the same |
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| AU2021106990A4 (en) | 2021-12-02 |
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