AU2017101924A4 - Emulsifiable concentrate - Google Patents

Abstract

An emulsifiable concentrate formulation including as active agents prosulfocarb and trifluralin and also including at least one agriculturally acceptable surfactant, wherein the sum of concentrations of prosulfocarb and trifluralin in the emulsifiable concentrate formulation is greater than 600 g/L, preferably greater than 700g/L, even more preferably greater than 800 g/L. 79

Description

EMULSIFIABLE CONCENTRATE

Technical Field This invention relates to multi-active herbicides formulations in the form of an emulsifiable concentrate (EC). In particular this invention relates to emulsifiable concentrate formulations that contain prosulfocarb and that also contain trifluralin. More particularly the invention relates to emulsifiable concentrate formulations wherein the cumulative herbicide loading (prosulfocarb plus trifluralin) is at least 500 g/L, preferably at least 700 g/L.

Background Art Prosulfocarb (also known as S-Benzyl dipropylthiocarbamate, and as S (phenylmethyl)dipropylcarbamothioate) is in the thiocarbamate family of herbicides (Group J, see http/www.croplife.org.au/resistance-strategy/2015 herbicide-resistance-mangement-strategies/#mode of action/) and has a mode of action based on the inhibition of lipid synthesis. Prosulfocarb is root-absorbed (below the seed), and when the root system of the weed extends beyond the prosulfocarb zone, the weed can survive. Technical grade prosulfocarb material has a melting point of approximately -20°C and a solubility in water of 13 mg/L at °C Up-take of Prosulfocarb by a plant is assisted by soil moisture.

Trifluralin (also known as 2,6-Dinitro-N,N-dipropyl-4-(trifluoromethy)aniline is a pre-emergence herbicide in the dinitroaniline family of herbicides (Group D). It is applied to soil to control annual grass (such as annual ryegrass) and broadleaf weeds. It acts by inhibiting root development, and can kill weeds as they germinate. Technical trifluralin melts at 46-47 °C and is highly insoluble in water. It is a volatile herbicide and may be incorporated into top-soil to reduce volatile loss.

The use of prosulfocarb and trifluralin in combination can be advantageous in the following agronomic scenarios: (i) to manage the control of herbicide-resistant weeds such as herbicide-resistant annual ryegrass, (ii) to achieve a broader spectrum of weed control, for example to enable control of wire-grass which may be difficult to control with prosulfocarb alone, and (iii) to provide a less phytotoxic alternative to other herbicide combinations (e.g. prosulfocarb metolachlor combinations).

Tank mixes of prosulfocarb and trifluralin have been proposed. For example the tank mixing of BOXER GOLD (a combination product with prosulfocarb and metolachlor) with trifluralin has been proposed for (i) extending weed-control spectrum, (ii) on sandy soils where moisture is limiting, and (iii) where herbicide movement into the seeding zone poses a crop safety risk (see label for Boxer Gold by Syngenta).

WO 2013083372 teaches that emulsifiable concentrates with better cold-storage characteristics may be obtained by including DMSO and benzyl alcohol in the formulation. The ECs contain a pesticide selected from the group of the fungicides, insecticides, nematicides, herbicides, safeners and/or growth regulators. Among the many herbicides recited individually are prosulfocarb and trifluralin, but there is no teaching that trifluralin and prosulfocarb should be co formulated in a one-pack EC formulation.

US 6,413,908 describes compositions containing dispersed phase agrochemicals, particularly phytoactives, such as growth regulators and/or herbicides, or pesticides, such as insecticides, fungicides, or acaricides, characterised in that they include as adjuvant a branched primary alcohol alkoxylate. In an embodiment the dispersed phase agrochemical is one or more of acetochlor, alachlor, nicosulfuron, primisulfuron, prosulfocarb, trifluralin, fenitrothion, propargite, iprodione and propiconazole, however there is no teaching that prosulfocarb and trifluralin should be co-formulated in a one-pack EC formulation.

If a farmer wants to apply both prosulfocarb and trifluralin to a field through a multi-nozzle spray rig, that farmer may separately add a single-active emulsifiable concentrate of prosulfocarb and a single-active emulsifiable concentrate of trifluralin to the spray water tank of his spray rig (this is called tank mixing). Disadvantages of tank-mix methodology include:

The requirement to transport and handle twice as many containers

. The requirement to safely dispose of twice as many empty containers . The capacity to make a mistake in the mixing ratio (this is particularly problematic when farm labourers are not well-educated) . The need for label instructions to be more complex, and to be co-ordinated between 2 separate containers o The need to have more carrier solvents and emulsifiers than are required in a one-pack formulation . Lower emulsion quality where actives are introduced into the spray water tank via separate formulations as opposed to the jointly optimised emulsion of a combined actives formulation.

The use of a one-pack highly-loaded EC formulation containing both prosulfocarb and trifluralin would avoid the disadvantages itemised above.

SUMMARY OF THE INVENTION

In a first aspect, the invention provides an emulsifiable concentrate formulation including: prosulfocarb; trifluralin; and at least one agriculturally acceptable surfactant, wherein the sum of concentrations of prosulfocarb and trifluralin in the emulsifiable concentrate formulation is greater than 600 g/L. Suitably, prosulfocarb and trifluralin are present in a weight ratio in the range of about 5:1 to about 1:1. Preferably, prosulfocarb and trifluralin are present in a weight ratio in the range of about 3.5:1 to about 2:1. In one embodiment, prosulfocarb is present at a concentration of about 500 to about 900 g/L and trifluralin is present at a concentration of about 100 to about 400 g/L. Suitably, a weight ratio of a herbicidal component consisting of prosulfocarb and trifluralin to a non-herbicidal component comprising the surfactant is at least 4:1. Suitably, the formulation of the present aspect further comprises at least one agriculturally acceptable solvent. In particular embodiments, the weight ratio of the herbicidal component to the agriculturally acceptable solvent is at least 6:1. The agriculturally acceptable solvent is preferably selected from the group consisting of aliphatic paraffin oils, aromatic solvents, C6-C18 aromatic solvents, chlorinated hydrocarbons, alcohols, ketones, ethers, esters, vegetable oils, methylated vegetable oils, petroleum fractions, sugar esters of fatty acids, alkane compounds, aryl compounds, alkylaryl compounds, heterocyclic compounds, lactams, amides, xylene, toluene, pyrrolidones, substituted pyrrolidones, glycol ethers, end-capped glycol ethers and any combination thereof More preferably, the agriculturally acceptable solvent is selected from the group consisting of ketones, esters, petroleum fractions, optionally substituted pyrrolidones and any combination thereof Suitably, the at least one agriculturally acceptable surfactant is selected from the group consisting of a non-ionic surfactant, an anionic surfactant, a cationic surfactant, a zwitterionic surfactant, an anion-cation composite surfactant and any combination thereof In one embodiment, the at least one agriculturally acceptable surfactant is or comprises a non-ionic surfactant. Suitably, the non-ionic surfactant is selected from the group consisting of alkoxylated block polymers, alkoxylated alcohols, alkoxylated alkylphenols, alkoxylated monostyryl phenols, alkoxylated distyryl phenols, alkoxylated tristyryl phenols, alkoxylated amines, alkoxylated amides, alkoxylated fatty esters, alkoxylated fatty acids and any combination thereof Preferably, the non-ionic surfactant is selected from the group consisting of alkoxylated alcohols, alkoxylated alkylphenols, castor oil ethoxylates, ethoxylated tallow amines, polyoxyethylene sorbitan monolaurate, ethylene oxide-propylene oxide block copolymers, alkoxylated monostyryl phenols, alkoxylated distyryl phenols, alkoxylated tristyryl phenols and any combination thereof More preferably, the non-ionic surfactant is selected from the group consisting of alkoxylated alcohols, nonylphenol alkoxylates, castor oil ethoxylates, ethoxylated tallow amines, polyoxyethylene sorbitan monolaurate, ethylene oxide-propylene oxide block copolymers, ethoxylated tristyryl phenols and any combination thereof Suitably, the non-ionic surfactant is present in an amount of about 10 to about 80 g/L in the formulation.

In certain embodiments, the at least one agriculturally acceptable surfactant is or comprises an anionic surfactant selected from the group consisting of alkyl or aryl or alkylaryl or alkylether sulfates, alkyl or aryl or alkylaryl sulfonates, alkyl or aryl or alkylaryl ether phosphates, alkyl carbonates and sarcosinates, carboxylated alkylphenols, carboxylated alcohol derivatives, sulfates or sulfonates of alkoxylated moieties, sulfonates of naphthalene or alkylnaphthalene or petroleum, and any combination thereof In one preferred embodiment, the anionic surfactant is or comprises a calcium alkylbenzene sulfonate salt. Suitably, the anionic surfactant is present in a concentration of about 15 to about 70 g/L. In one embodiment, the at least one agriculturally acceptable surfactant is or comprises an anion-cation composite surfactant selected from the group consisting of alkylphenol ether sulfate/tallow amine ethoxylate salts, alcohol ether sulfate/tallow amine ethoxylate salts and dodecylbenzenesulfonic acid/ethoxylated alkylamine salts. The anion-cation composite surfactant suitably is or comprises an alkylphenol ethersulfate/tallow amine ethoxylate. In particular embodiments, the formulation comprises at least two agriculturally acceptable surfactants and wherein the at least two agriculturally acceptable surfactants include at least one anionic surfactant and at least one non ionic surfactant. In a second aspect, the invention provides a method of preparing an emulsifiable concentrate formulation of the first aspect, including the steps of: (a) adding prosulfocarb to a vessel; (b) adding trifluralin to the vessel; (c) adding at least one agriculturally acceptable surfactant to the vessel, and (d) mixing the prosulfocarb, trifluralin and the agriculturally acceptable surfactant to thereby prepare the emulsifiable concentrate formulation. Suitably, the method of the present aspect further includes the step of adding at least one agriculturally acceptable solvent to the vessel. In a third aspect, the invention provides a emulsifiable concentrate formulation prepared by the method of the second aspect. In a fourth aspect, the invention provides a stable emulsion produced by mixing an emulsifiable concentrate formulation of prosulfocarb and trifluralin according to the first or third aspects with water.

In a fifth aspect, the invention provides a method of controlling weeds in a target crop including the step of applying an effective amount of a dilute form of the emulsifiable concentrate formulation of the first and third aspects to the target crop to thereby control said weeds. In a sixth aspect, the invention provides a method of controlling weeds in a target crop including the step of applying an effective amount of the stable emulsion of the fourth aspect to the target crop to thereby control said weeds.

DETAILED DESCRIPTION OF THE INVENTION

In a first aspect the invention relates to an emulsifiable concentrate co-formulation of prosulfocarb and trifluralin which forms a stable emulsion when mixed with an excess of water. Further to this, the sum of concentrations of prosulfocarb and trifluralin in the emulsifiable concentrate formulation is preferably greater than 600 g/L. In particular embodiments, the emulsifiable concentrate has an herbicidal component consisting of prosulfocarb and trifluralin in a weight ratio in the range :1 to 1:1 and a non-herbicidal component comprising at least one agriculturally acceptable solid, liquid or liquid-containing surfactant, wherein the weight ratio of the herbicidal component to the non-herbicidal component is at least 3:1.

It will be well understood that the term "emulsifiable concentrate formulation" or "emulsifiable concentrate" (EC)refers to a liquid formulation or concentrate of an active agent, such as a pesticide, which, on dilution in water or a water-containing liquid, form an emulsion such as a spontaneous milky white emulsion comprising a dispersed water immiscible phase. The term "emulsion", as used herein, refers to a fine dispersion of minute droplets of one liquid in another in which it is not soluble or miscible and includes microemulsions and macroemulsions.

In an embodiment the weight ratio of the herbicidal component to the non herbicidal component is at least 4:1. In an embodiment the weight ratio of the herbicidal component to the non-herbicidal component is at least 5:1. In an embodiment the weight ratio of the herbicidal component to the non-herbicidal component is at least 6:1. In an embodiment the weight ratio of the herbicidal component to the non-herbicidal component is at least 8:1. In an embodiment the weight ratio of the herbicidal component to the non-herbicidal component is at least 10:1.

In an embodiment the emulsifiable concentrate comprises prosulfocarb and trifluralin in a weight ratio in the range 4:1 to 1:1. In an embodiment the emulsifiable concentrate comprises prosulfocarb and trifluralin in a weight ratio in the range 3.5:1 to 2:1.

Suitably, prosulfocarb is present in an amount of at least 500 g/L. Accordingly, prosulfocarb may be present in an amount of between about 500 g/L and about 900 g/L, about 600 g/L and about 800 g/L, about 650 g/L and about 750 g/L, or any range therein. In particular embodiments of the present invention, prosulfocarb is present in an amount of about 500, 510, 520, 530, 540, 550, 560, 570, 580, 590, 600, 610, 620, 630, 640, 650, 660, 670, 680, 690, 700, 710, 720, 730, 740, 750, 760, 770, 780, 790, 800, 810, 820, 830, 840, 850, 860, 870, 880, 890, 900 g/L or any range therein. In certain embodiments of the present invention, prosulfocarb is present in an amount of between about 600 g/L and about 800 g/L. In one preferred embodiment, prosulfocarb is present in an amount of between about 600 g/L and about 700 g/L.

Suitably, trifluralin is present in an amount of at least 100 g/L. Accordingly, trifluralin may be present in an amount of between about 100 g/L and about 400 g/L, about 150 g/L and about 350 g/L, about 200 g/L and about 300 g/L, or any range therein. In particular embodiments of the present invention, trifluralin is present in an amount of about 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, 250, 260, 270, 280, 290, 300, 310, 320, 330, 340, 350, 360, 370, 380, 390, 400 g/L or any range therein. In certain embodiments of the present invention, trifluralin is present in an amount of between about 100 g/L and about 400 g/L. In one preferred embodiment, trifluralin is present in an amount of between about 200 g/L and about 300 g/L.

Suitably, the sum of concentrations of prosulfocarb and trifluralin in the emulsifiable concentrate formulation is greater than 600 g/L. Accordingly, prosulfocarb and trifluralin may be present in a combined amount or concentration of between about 600 g/L and about 950 g/L, about 700 g/L and about 925 g/L, about 800 g/L and about 900 g/L, or any range therein. In particular embodiments of the present invention, prosulfocarb and trifluralin are present in a combined amount or concentration of about 600, 610, 620, 630, 640, 650, 660, 670, 680, 690, 700, 710, 720, 730, 740, 750, 760, 770, 780, 790, 800, 810, 820, 830, 840, 850, 860, 870, 880, 890, 900, 910, 920, 930, 940, 950 g/L or any range therein. In certain embodiments of the present invention, prosulfocarb and trifluralin are present in a combined amount or concentration of between about 800 g/L and about 950 g/L. In one preferred embodiment, prosulfocarb and trifluralin are present in a combined amount or concentration of between about 825 g/L and about 925 g/L.

As used herein, the term "surfactant" or "surface-active agent" refers to an agent, usually an organic chemical compound that is at least partially amphiphilic (i.e., typically containing a hydrophobic tail group and hydrophilic polar head group). Given their structure, surfactants are generally capable of lowering the surface tension (or interfacial tension) between two liquids or between a liquid and a solid. Further to this, these properties typically allow solubility of the surfactant in organic solvents as well as in water, and allow the surfactant to promote solubilization or at least dispersal of fatty/waxy materials in water and water containing solutions. In this regard, a surfactant may act as a detergent, a wetting agent, an emulsifying agent, a foaming agent and/or a dispersing agent.

The surfactant, including one or a plurality of surfactants (e.g., 1, 2, 3, 4, 5 etc surfactants), are suitably present in a high enough concentration that allows for the production of a highly loaded emulsifiable concentrate formulation of prosulfocarb and trifluralin. In this regard, it will be apparent that an amount of the surfactant of the emulsifiable concentrate formulation can vary, for example, depending on the particular concentrations of prosulfocarb and trifluralin and/or the particular surfactant to be included therein.

Suitably, the surfactant is present in an amount of at least 5 g/L. Accordingly, the surfactant of the present invention may be present in an amount of between about g/L and about 200 g/L, about 25 g/L and about 120 g/L, about 40 g/L and about 100 g/L, or any range therein. In particular embodiments of the present invention, the surface active agent is present in an amount of about 5, 6, 7, 8, 9, 10, 11, 12, 13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34, ,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56, 57,58,59,60,61,62,63,64,65,66,67,68,69,70,71,72,73,74,75,76,77,78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 105, 110, 115, 120, 125, 130, 135, 140, 145, 150 g/L or any range therein. In certain embodiments of the present invention, the surfactant is present in an amount of between about 35 g/L and about 100 g/L. In one preferred embodiment, the surfactant is present in an amount of between about 40 g/L and about 80 g/L.

In an embodiment the at least one agriculturally acceptable solid, liquid or liquid containing surfactant is selected from the group consisting of non-ionic, anionic, cationic, zwitterionic and cation-anion composite surfactants.

In an embodiment the agriculturally acceptable solid, liquid or liquid-containing surfactant comprises a non-ionic surfactant selected from the group consisting of (i) alkoxylated moieties such as alkoxylated block polymers (such as ethylene oxide - propylene oxide (EO-PO) block copolymers), alkoxylated alcohols, alkoxylated alkylphenols, alkoxylated monostyryl phenols, alkoxylated distyryl phenols, alkoxylated tristyryl phenols, alkoxylated amines, alkoxylated amides, alkoxylated fatty esters, alkoxylated oils, alkoxylated fatty esters, alkoxylated fatty acids, and the like, (ii) derivatives of polyhydric alcohols such as alkyl derivatives, including alkyl polyglycosides and alkyl glucosides, and alkyl derivatives of glycerol, and (iii) fatty amine higher-mole ethoxylates which have non-ionic characteristics such as cloud point and compatibility with anionic surfactants. The term alkoxylated moiety includes moieties that have been reacted with ethylene oxide, propylene oxide or butylene oxide, and also includes moieties where more than one type of the aforesaid oxides have been reacted in sequence or in admixture.

In an embodiment the at least one agriculturally acceptable solid, liquid or liquid containing surfactant comprises a non-ionic surfactant selected from the group consisting of alkylphenol alkoxylates, alcohol alkoxylates, mono-, di- or tri-styryl phenol alkoxylates, propylene glycol alkoxylates, fatty ester alkoxylates, castor oil ethoxylates, EO-PO block copolymers, tallow amine alkoxylates and sorbitan-fatty acid ester alkoxylates.

In an embodiment the non-ionic surfactant is selected from the group consisting of propyleneglycol alkoxylate, alcohol alkoxylates, alcohol alkoxylates having a HLB within 2 HLB units of 17.5, polypropyleneglycol(with 30-40P0) polyethyleneglycol (with 2030EO)- polypropyleneglycol (with 25-35PO) triblock material, 35P0-25E0-30PO triblock material, C8-C12 alkylphenol alkoxylate, nonylphenol (9E0)-(10P0) (CAS#37251-69-7) , tristyryl alkoxylate CAS#99734 09-5 HLB 13), nonylphenol alkoxylate and castor oil ethoxylates. In an embodiment the material sold as Termul 203 (and described by Huntsman as an alcohol alkoxylate), the material sold as Termul 3150 (and described by Huntsman as ethoxylated tristyryl phenol), the material sold as Termul 200 (and described by Huntsman as nonylphenol alkoxylate), the material sold as Termul 1284 (and described by Huntsman as castor oil ethoxylate) or the materials sold as Teric N8 - N15 (and described by Huntsman as nonyl phenol ethoxylates) is used.

In an embodiment the non-ionic surfactant is present at 20-70g/L in the emulsifiable concentrate formulation. In an embodiment the non-ionic surfactant is present at 30-50g/L in the emulsifiable concentrate formulation. In an embodiment the non-ionic surfactant is present at 34-42g/L in the emulsifiable concentrate formulation.

In an embodiment the at least one agriculturally acceptable solid, liquid or liquid containing surfactant comprises an anionic surfactant selected from the group consisting of alkyl or aryl or alkylaryl or alkylether sulfates, alkyl or aryl or alkylaryl sulfonates, alkyl or aryl or alkylaryl phosphate esters, alkyl or aryl or alkylaryl ether phosphates, alkyl carboxylates and sarcosinates, carboxylated alkylphenols, carboxylated alcohol derivatives (including carboxylated glycol derivatives) sulfates and sulfonates of alkoxylated moieties, sulfonates of naphthalene or alkylnaphthalene or petroleum and the like. The alkyl moieties can be linear or branched, or saturated or unsaturated. The aryl moieties may be naphthalene or alkylnaphthalene moieties.

It will be apparent in light of the foregoing that one or more surfactants may be introduced into the formulation of the invention as a soluble concentration in a further solvent (e.g., calcium dodecylbenzene sulfonate in ethyl hexanol) and the latter may equate, for example, to amounts up to about 10 g/L to about 25 g/L or more of the formulation. Given the above, it will be appreciated that such amounts of the further solvent may make little or no contribution to the solvency of prosulfocarb and/or trifluralin within the formulation of the invention.

Accordingly, in an embodiment the anionic surfactant is selected from the group consisting of calcium alkylbenzene sulfonate salt in a liquid solvent carrier such as 2-ethyl-hexanol, wherein the alkyl moiety, which may be straight or branched is C8-C14 alkyl. In an embodiment the alkyl moiety is C1O-C12 alkyl. In an embodiment the anionic surfactant is present as a 40-70% solution in carrier solvent. In an embodiment the anionic surfactant is present as a 5 0 -6 0 % solution

in carrier solvent.

In an embodiment the anionic surfactant is present in the range of about 20 g/L to about 80 g/L in the formulation (weight based on solution weight when the anionic surfactant is dissolved in a solvent for said surfactant, for example dissolved at 60% in 2-ethyl hexanol). In an embodiment the anionic surfactant is present in the range of about 35 g/L to about 50 g/L in the formulation (weight based on solution weight when the anionic surfactant is dissolved in a solvent for said surfactant, for example dissolved at 60% in 2-ethyl hexanol).

In an embodiment the anionic surfactant is present in the range of about 12 g/L to about 48 g/L in the formulation (based on weight of surfactant net of the weight of carrier solution for the surfactant). In an embodiment the anionic surfactant is present in the range of about 21 g/L to about 30 g/L the formulation (based on weight of surfactant net of the weight of carrier solution for the surfactant).

In an embodiment the at least one agriculturally acceptable solid, liquid or liquid containing surfactant includes a cationic surfactant selected from the group consisting of moieties containing primary, secondary, tertiary or quaternary alkyl or aryl amines such as alkyltrimethylammonium moieties, dialkyldimethyl ammonium moieties, cetylpyridinium moieties, benzalkonium moieties, benzethonium moieties and the like, and fatty acid low-mole ethoxylates that are substantially protonated in aqueous solution. The alkyl moieties can be linear or branched, or saturated or unsaturated.

In an embodiment the at least one agriculturally acceptable solid, liquid or liquid containing surfactant includes a zwitterionic surfactant selected from the group consisting of betaines, phosphatidyl cholines and surfactants where the head group comprises both an acidic and a basic moiety such as alkyl aminopropionic acid moieties and N-carboxymethyl moieties.

In an embodiment the at least one agriculturally acceptable solid, liquid or liquid containing surfactant includes a cation-anion composite surfactant wherein an amine-functional surfactant has participated in a proton-exchange reaction with and alkyl or aryl or alkylaryl acid such as an alkyl or aryl or alkylaryl sulfate or sulfonate or ether sulfate. Examples of cation-anion composite surfactants include alkylphenol ether sulfate/tallow amine ethoxylate salts, alcohol ether sulfate/tallow amine ethoxylate salts and dodecylbenzenesulfonic acid/ethoxylated alkylamine salts. In an embodiment a cation-anion composite surfactant sold by Stepan Company as Toximul TANS 8 and described as alkylphenol ethersulfate/tallow amine ethoxylate is used.

In an embodiment, the non-herbicidal component comprises at least one agriculturally acceptable solvent. The term "solvent" refers to any liquid capable of maintaining another substance in solution. The term "agriculturally acceptable solvent" as used herein refers to a solvent is not unacceptably damaging to a plant and/or its environment, and/or not unsafe to the user or others that may be exposed to the solvent when used as described herein. Examples of solvents include, but are not limited to, organic solvents. It will be apparent to the skilled artisan that the agriculturally solvent may include any appropriate solvent as are known in the art. By way of example, the agriculturally acceptable solvent may comprise at least one of solvent naphtha (petroleum), heavy aromatic fraction, xylene, toluene, pyrrolidones including N-alkylated pryrrolidones such as n-methyl pyrrolidone, cyclohexanone, acetone, glycol ethers such as diethylene glycol monomethyl ether (including the material sold under the trade name Carbitol), ethylene glycol monobutyl ethers (including the material sold under the trade name Butyl

Glysolv), propylene glycol monomethyl ether (including the material sold under the trade name Glysolv PM), methanol, ethanol, isopropanol, decanol, paraffins, hexane, acetic acid C6-C8 branched alkyl ester (including the material sold under the trade name Exxate 700).

For the present invention, the agriculturally acceptable solvent may be present in an amount from about 5 g/L to about 200 g/L or any range therein such as, but not limited to, about 7.5 g/L to about 100 g/L, or about 10 g/L to about 80 g/L of the emulsifiable concentrate formulation. In particular embodiments of the present invention, the agriculturally acceptable solvent is present in an amount of about 5, 6, 7, 8, 9, 10, 12.5, 15, 17.5, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, , 95, 100, 105, 110, 115, 120, 125, 130, 135, 140, 145, 150, 155, 160, 165, 170, 175, 180, 185, 190, 195, 200 g/L, or any range therein, of the emulsifiable concentrate formulation. In certain embodiments of the present invention, the agriculturally acceptable solvent is present in an amount of at least about 40 g/L of the emulsifiable concentrate formulation. More preferably, the agriculturally acceptable solvent is present in an amount ranging between about 30 g/L to about g/L of the emulsifiable concentrate formulation.

In an embodiment the weight ratio of the herbicidal component to agriculturally acceptable solvent is at least 6:1. In an embodiment the weight ratio of the herbicidal component to agriculturally acceptable solvent is at least 8:1. In an embodiment the weight ratio of the herbicidal component to agriculturally acceptable solvent is at least 10:1. In an embodiment the weight ratio of the herbicidal component to agriculturally acceptable solvent is at least 15:1. In an embodiment the formulation of the invention may optionally comprise at least one agriculturally acceptable solvent being a solvent selected from the group consisting of aliphatic paraffinic oils, aromatic solvents, C6-C16 aromatic solvents, chlorinated hydrocarbons, alcohols, ketones, ethers, esters, vegetable oils, methylated vegetable oils, petroleum fractions, sugar esters of fatty acids, alkane compounds, aryl compounds, alkylaryl compounds, heterocyclic compounds, lactams, amides, xylene, toluene, pyrrolidones, substituted pyrrolidones, glycol ethers, end-capped glycol ethers.

In an embodiment the formulation of the invention may optionally comprise at least one agriculturally acceptable solvent being a solvent selected from the group consisting of ketones, esters, petroleum fractions and optionally substituted pyrrolidones.

In an embodiment the agriculturally acceptable solvent in the formulation of the invention is present at 0-100 g/L. In an embodiment the agriculturally acceptable solvent in the formulation of the invention is present at 0-80 g/L. In an embodiment the agriculturally acceptable solvent in the formulation of the invention is present at 20-80 g/L.

In an embodiment the formulation of the invention may comprise at least two agriculturally acceptable surfactants including at least one anionic surfactant and at least one non-ionic surfactant.

In an embodiment the at least one anionic surfactant and the at least one non-ionic surfactant are both present with the at least one anionic surfactant being present in the range 20-80 g/L in the formulation (weight based on solution weight when the anionic surfactant is dissolved in a solvent for said surfactant, for example, dissolved at 60% in 2-ethyl hexanol), and the at least one non-ionic surfactant being present at 20-70g/L in the formulation. In an embodiment the at least one non-ionic surfactant is present at 30-50g/L in the formulation. In an embodiment the at least one non-ionic surfactant is present at 34-42g/L in the formulation.

In an embodiment the at least one anionic surfactant and the at least one non-ionic surfactant are both present with the at least one anionic surfactant being present in the range 12-48 g/L in the formulation (weight based on anionic surfactant net of carrier solvent for the surfactant) and the at least one non-ionic surfactant being present at 20-70g/L in the formulation. In an embodiment the anionic surfactant is present at 21-30 g/L net of carrier solvent in the formulation. In an embodiment the non-ionic surfactant is present at 30-50g/L net of carrier solvent in the formulation. In an embodiment the non-ionic surfactant is present at 33-42 g/L net of carrier solvent in the formulation.

In an embodiment the emulsifiable concentrate comprises 550-800 g/L of prosulfocarb, 200-350g/L of trifluralin, 0 - 80 g/L of agriculturally acceptable solvent, 20-65g/L nonionic surfactant, 20-80 g/L of anionic surfactant (based on solution weight when the anionic surfactant is carried in a carrier solvent).

In an embodiment the emulsifiable concentrate comprises 650-710 g/L of prosulfocarb, 210-300g/L of trifluralin, 20 - 80 g/L of agriculturally acceptable solvent, 30-50g/L nonionic surfactant, 35-50 g/L of anionic surfactant (based on solution weight when the anionic surfactant is carried in a carrier solvent).

In an embodiment the emulsifiable concentrate comprises 550-800 g/L of prosulfocarb, 200-350g/L of trifluralin, 0-80g/L of agriculturally acceptable solvent, 20-65g/L non-ionic surfactant, 9-42 g/L of anionic surfactant (based on weight of anionic surfactant net of carrier solvent).

In an embodiment the emulsifiable concentrate comprises 650-710 g/L of prosulfocarb, 210-300g/L of trifluralin, 20-80g/L of agriculturally acceptable solvent, 30-50g/L nonionic surfactant, 21-30 g/L of anionic surfactant (based on weight of anionic surfactant net of carrier solvent).

One or more additional auxiliary agents, such as adjuvants, synergists, preservatives, colouring agents (e.g., dyes), odourants, embittering agents and other deterrents and the like, as are known in the art, can also be added where desired to modify the properties of the emulsifiable concentrate formulation as required.

It will be understood that it is desirable for the emulsifiable concentrate provided herein to be readily or easily pumped or poured from a storage vessel. Preferably, the emulsifiable concentrate formulation has a viscosity at room temperature (i.e., C) of no more than 2000 cPs (e.g., 1, 5, 10, 20, 30, 40, 50, 100, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000 cPs and any range therein), as viscosities above this typically make it difficult or impractical to pump or pour the formulation. Preferably, the emulsifiable concentrate formulation of the invention has a viscosity at room temperature of about or less than 400 cPs.

In a still further aspect of the invention there is provided a method of preparing an emulsifiable concentrate formulation of prosulfocarb and trifluralin. The method includes the steps of: adding prosulfocarb to a clean empty formulation vessel; adding trifluralin to the formulation vessel; adding at least one agriculturally acceptable surfactant and, optionally, at least one agriculturally acceptable organic solvent to the formulation vessel; and

agitating to uniformity.

In an embodiment an agriculturally acceptable organic solvent is added to the formulation vessel.

In an embodiment the method also includes the step of clearing residual surfactant from pumps or process lines with an agriculturally acceptable solvent. In an embodiment an agriculturally acceptable organic solvent is added to the formulation vessel and residual surfactant is cleared from pumps or process lines with the same agriculturally acceptable solvent.

In an embodiment preparation of the emulsifiable concentrate takes place at a temperature of > 30°C. In an embodiment the preparation takes place at a temperature between 30°C and 60 °C.

In an embodiment the vessel is agitated for at least 30 minutes after addition of the last ingredient.

With respect to present aspect of preparing an emulsifiable concentrate formulation, it will be appreciated that this method may be performed using commercially available equipment, such as formulation vessels and the like, known in the art.

In another aspect, the invention provides an emulsifiable concentrate formulation prepared by the method of the aforementioned aspect.

In a further aspect the invention relates to a stable emulsion produced by mixing an emulsifiable concentrate co-formulation of prosulfocarb and trifluralin according to the first aspect of the present invention with an excess of water.

Stability is established by adding 5mL of the emulsifiable concentrate to 95mL of water at room temperature in a measuring cylinder and inverting the cylinder 5 times. The emulsion is stable if no more 1 mL of oil and no more than 3 mL of cream form after standing for 30 minutes.

In an embodiment the contents of the measuring cylinder should re-emulsify after standing for 24 hrs when the measuring cylinder is inverted 5 times.

In an embodiment less than 60 mL of foam is observed after 1 minute when a 200 mL emulsion contained in a container is inverted is inverted 30 times.

In an embodiment the pH of the formulation is in the range of 4 to 10. In an embodiment the pH of the formulation is in the range of 6 to 9.

In an embodiment specific gravity for the formulation is in the range of 1.00 to 1.300. In an embodiment specific gravity for the formulation is in the range of 1.030 to 1.130. In an embodiment specific gravity for the formulation is in the range of 1.060 to 1.110

In an embodiment the viscosity of the formulation at 20 °C is 1 to 2000 cPs. In an embodiment the viscosity of the formulation at 20 °C is 10 to 500 cPs. In an embodiment the viscosity of the formulation at 20 °C is <200 cPs such as 50 to 200 cPs.

In an embodiment the viscosity of the formulation at 5 °C is 1 to 2000 cPs. In an embodiment the viscosity of the formulation at 5 °C is 10 to 1000 cPs. In an embodiment the viscosity of the formulation at 5°C is <1000 cPs, such as 20 to 1000 cPs. In an embodiment the viscosity of the formulation at 5 °C is <400 cPs, such as 50 to 400 cPs.

It is desirable for the emulsifiable concentrate to be easily pumped or poured. Viscosities of beyond 2000cPs represent a practical upper limit beyond which it is difficult to pump or pour the formulation. A more desirable viscosity is less than 400 cPs.

The present invention also relates to a method of controlling weeds in a target crop by application, prior to crop emergence, of a diluted emulsifiable concentrate co formulation of the herbicides prosulfocarb and trifluralin according to the first aspect of the present invention.

In an embodiment the application rate is (based on volume of the emulsifiable concentrate) is in the range 1-8 L/ha. In an embodiment the application rate is 2 L/ha. In an embodiment the application rate is about 3L/ha.

The ratios described above, such as the ratio of herbicide components (prosulfocarb plus trifluralin) to non-herbicidal components, the ratio of herbicide components (prosulfocarb plus trifluralin) to solvent, and the ratio of herbicide components (prosulfocarb plus trifluralin) to solubilising moiety, are important quality parameters for an EC formulation as the ratios affect:

1. The quantity of solvent released to the environment as a consequence of applying a given amount of herbicide to a cultivation zone; 2. The amount of high-quality packing material that is utilised in carrying a given amount of herbicide to a cultivation zone; 3. The amount of used packaging material that needs to be recycled or otherwise disposed of after applying a given amount of herbicide to a cultivation zone; 4. The contact toxicity of the EC formulation; 5. The flammability of the EC formulation.

Formulations according to the present invention are advantageous as the ratio of herbicidal components to non-herbicidal components is relatively high compared to a formulation that would result if a prosulfocarb EC and a trifluralin EC are individually added to a spray tank. Furthermore, the ratio of herbicidal components to organic solvent is relatively high.

The non-herbicidal component includes a solubilising moiety for the combination of prosulfocarb and trifluralin which comprises liquid systems that include agriculturally acceptable solvents, and also liquid systems that include agriculturally acceptable liquid, or liquid-containing surfactants, provided that both prosulfocarb and trifluralin (in combination) dissolve in that liquid system. A solubilising moiety for the combination of prosulfocarb and trifluralin may contain one, two or more liquid components, being components that are liquid at 20 °C, which constitute the solubilising moiety system for the combination of prosulfocarb and trifluralin. The weight of a solubilising moiety for the combination of prosulfocarb and trifluralin is taken to be the sum of the weights of liquid components, being the components that are liquid at 20 °C, which constitute the solubilising moiety system for the combination of prosulfocarb and trifluralin. For the avoidance of doubt, if a solubilising moiety for the combination of prosulfocarb and trifluralin happens to include one or more solubilised solids (e.g. a solid dissolved surfactant), the weight of the solubilising moiety for the combination of prosulfocarb and trifluralin is taken to be the sum of the weights of the liquid components of the solvent system for the combination of prosulfocarb and trifluralin, but does not include the weights of non-prosulfocarb, non trifluralin solid components that may be dissolved. For the avoidance of doubt, the solubilising system does not include herbicidal components, even if they are in liquid form.

In an embodiment the ratio of total herbicide to solubilising moiety is more than :1. In an embodiment the ratio of total herbicide to solubilising moiety is more than 8:1. In an embodiment the ratio of total herbicide to solubilising moiety is more than 10:1. In an embodiment the ratio of total herbicide to solubilising moiety is more than 12:1.

The term "agriculturally acceptable" means registered or otherwise approved for use in agriculture in at least one country.

In the claims which follow and in the preceding description of the invention, except where the context requires otherwise due to express language or necessary implication, the word "comprise" or variations such as "comprises" or "comprising" is used in an inclusive sense, i.e. to specify the presence of the stated features but not to preclude the presence or addition of further features in various embodiments of the invention.

It will be appreciated that the indefinite articles "a" and "an" are not to be read as singular indefinite articles or as otherwise excluding more than one or more than a single subject to which the indefinite article refers. For example, "a" surfactant includes one surfactant, one or more surfactants and a plurality of surfactants.

It is to be understood that, if any prior art publication is referred to herein, such reference does not constitute an admission that the publication forms a part of the common general knowledge in the art, in Australia or any other country.

EXAMPLES

The following examples are provided for illustrative purposes only and are not to be taken as placing any limitation on the nature of the invention or the scope of the claims.

Example 1

Formulation of a nominally 10000L batch of product is as follows:

1.1. Ensure formulation vessel is empty and clean

1.2. Charge solvent as follows to the formulation vessel with agitator off:

1. Aromatic solvent 150 (e.g. Recosol 150) 450kg 1.3. Charge active ingredients as follows to the formulation vessel with intermittent agitation following the addition of every 1000kg or so (N.B. Trifluralin technical material has a nominal melting point of the order of 50°C - heating will generally be required to establish a liquid form prior to processing

2. Prosulfocarb 95% Tech 7053kg 3. Trifluralin 95% Tech 2632kg 1.4. Charge the surfactants as follows, clearing residual surfactant from any pumps or process lines used with the remaining complement of solvent:

4. Alkylbenzenesulfonic acid, calcium salt in 2 433kg ethvlhexanol (e.2. Ninate 60E) 5. Ethoxylated tristyryl phenol (e.g. Termul 3150) 353kg 6. Aromatic solvent 150 (e.g. Recosol 150) 140kg 1.5. Continue agitating for a minimum of 30 minutes following the last ingredient's addition

The EC produced in this process has the following composition:

Component Purchased from (incl. trade name) Parts by weight (g/L) Prosulfocarb 98.5% technical Prosulfocarb (CAS# 52888-80- 9)

Manufactured by Ihara Chemical Industry, 1800, Nakanoka Fujikawa cho, Ihara-gun, Shizuoka, Japan Purchased from Shanghai MEG Imp. and Exp. Corp., Rom 4 101, No. 299, Bisheng Road, Zhangjiang Hi-tech Park, Shanghai, 201204 China

Trifluralin 95% technical Trifluraln (CAS# 1582-09-8) 263.2 Manufactured by Jiangsu Fengshan Group Co. Ltd., CaomiaoTown Dafeng City, Jiangsu Province 224134 PR China Purchased from Tinajin Textile Group Import and Export Inc., No. 3 Yunnan Road, Tianjin

Aromatic solvent 150 (e.g. Solvent naphtha (petroleum), heavy 59.1 Recosol 150) aromatic (CAS# 64742-94-5) Proprietary Name = Recosol 150

Manufactured by Recochem Purchased from Recochem

Nonionic surfactant e.g. Ethoxylated tristyryl phenol Ethoxylated tristyryl phenol (CAS# 99734-09-5) Proprietary (e.g. Termul 3150) Name = Termul 3150

Manufactured by Huntsman

Purchased from Recochem Anionic surfactant e.g. Alkylbenzenesulfonic acid, calcium 43.2 Alkylbenzenesulfonic acid, salt in 2-ethylhexanol (CAS# 68584 calcium salt in 2- 23-6 in 104-76-7) ethylhexanol (e.g. ninate Proprietary Name = Ninate 60E E wherein the calcium salt is present as a 60% Manufactured by Stepan Purchased wt/wt solution) from Orica Australia

The properties of the formulation are set out in the table below. The formulation generated a high-quality emulsion when added to excess water, and was stable at cold temperatures.

Test Test Method Observed Parameter Appearance Visual Orange liquid, homogeneous Assay Validated chromatographic 672g/L method (Accuracy: 98-102%) prosulfocarb (Linearity: R > 0.99) 250g/L (Precision: s/average < 2%) trifluralin

pH (1%) CIPAC MT 75.3 7.6 SG CIPAC MT 3.1 1.081 Emulsion CIPAC MT 36.1 Trace oil Characteristics (complies) Persistent CIPAC MT 47.2 20mL (1 Foaming minute)

Cold Visual Complies temperature stability

Viscosity Brookfield viscometer 40cPs at 20C Viscosity Brooktield 95cPs at 5C viscometer

Long Term Acceptable, as per Complies Performance above values

Example 2 The following composition was similar to example 1 except that acetone was used as the solvent.

FORMULATION Component CAS # Functio Amount Loading, (Chemical name) n , g g/L S-(phenylmethyl) 52888-80-9 Active 3400.55 666.5 dipropylcarbamothioate ingredie e.g. Prosulfocarb nt (98.4

2,6-dinitro-N,N-dipropyl-4- 1582-09-8 Active 1300.4 247.1 (trifluoromethyl)benzenamine ingredie e.g. Trifluralin (95.6% nt Acetone 67-64-1 Solvent 244.45 48.9 Calcium 26264-06-2 Surfactan 202.55 40.5 dodecylbenzene t sulfonate used: Ninate 60E (anionic -,iirfqctqnt Ethoxylated tristyryl 99734-09-5 Surfactan 200.6 40.1 phenol used: Termul 3150 t (non-ionic surfactant) Total, g 5348.6

Parameter Method Results Appearance Visual Red clear liquid

Assay Validated chromatographic 666.5 g/L method (Accuracy: 98-102 %)

(Linearity: R>0.99) (Precision: s/average <2%) Validated chromatographic Assay method (Accuracy: 98-102 %) 247.1 g/L (Linearity: R>0.99) (Precision: s/average <2%) pH at H MIT 75.3 8.06 1% aq. Solution Specific gravity 1.069 (temperature at CIPAC MT 3.1 20C) Emulsion characteristics CIPAC MT 36.1 Traces of oil

Persiste CIPAC MT 47.2 20 mL nt Cold temp. Red clear liquid, stability homogeneous, (Accelerat MT75.3 free from phase ed Ageing) separation in any format Viscosity (temperature at MT 192 65 cPs C) Viscosity (temperature at. MT 192 28 cPs 20C)

Performance Acceptable, as per above values

Example 3 The following composition was made (similar to example 1 except that acetophenone was used as the solvent).

Component CAS # Function Amount, g Loading,

(Chemical name) g/L S-(phenylmethyl) 52888- Active 3402.9 667.0 dipropylcarbamothioate 80-9 ingredient e.g. Prosulfocarb(98.4% purity) 2,6-dinitro-N,N-dipropyl-4- 1300.8 247.2 (trifluoromethyl)benzenami 1582-09- Active ne e.g. Trifluralin (95.6% 8 ingredient purity)

Acetophenone 98-86-2 Solvent 348.55 69.7

Calcium dodecylbenzene Surfactant 202.85 40.6 sulfonate 26264 used: Ninate 60E(anionic 06-2 surfactant)

Ethoxylated tristyryl phenol 99734- Surfactant 201.15 40.2 used: Termul 3150 (non- 09-5 ionic surfactant) Total, g 5456.3

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic method Assay (Accuracy: 98-102 %) 667.0 g/L (Linearity: R>0.99) (Precision: s/average <2%) Validated chromatographic Assay method 247.2 g/L (Accuracy: 98-102 %) (Linearity: R>0.99) (Precision: s/average <2%) pH at H MIT 75.3 7.87 1% aq. Solution Specific gravity CIPAC MT 3.1 1.091 (temperature at 20C) Emulsion chr stic CIPAC MT 36.1 Traces of oil characteristics Persistent Foaming CIPAC MT 47.2 22 mL

Red clear liquid, Cold temp. stability homogeneous, free (Accelerated Ageing) MT75.3 from phase separation in any format Viscosity MT 192 110 cPs (temperature at 5C) Viscosity MT 192 39 cPs (temperature at 20C) LongTerm Acceptable, as per above Performance values

Example 4 The following composition was similar to example 1 except ethyl benzoate was used as the solvent).

Component CAS # Function Amount Loading, (Chemical name) ,Fg g/L S-(phenylmethyl) dipropylcarbamothioate Active e.g. Prosulfocarb(98.4% 52888-80-9 ingredient purity) 2,6-dinitro-N,N dipropyl-4 (trifluoromethyl)benz Active ingren 1304.45 247.8 ena mine e.g. Trifluralin 1582-09-8 (95.6%

Ethyl Benzoate 93-89-0 Solvent 303.8 60.8

Calcium dodecylbenzene 26264-06-2 Surfactant 200.8 40.2 sulfonate used: Ninate 60E

Fthoxylated 99734-09-5 Surfactant 201 40.2 tristyryl phenol used: Termul 3150 (non-ionic Total, g 5410.7

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic Assay method (Accuracy: 98-102%) 666.5 g/L (Linearity: R>0.99) (Precision: s/average <2.%) Validated chromatographic Assay method (Accuracy: 98-102%) 247.8 g/L (Linearity: R>0.99) (Precision: s/average <2%) pH at H MIT 75.3 7.86 1% aq. Solution Specific gravity 1.082 (temperature at CIPAC MT 3.1 C) Emulsion chrc.sic CIPAC MT 36.1 Traces of oil characteristics Persistent CIPAC MT 47.2 26 mL Foaminl Cold Redclearliquid, temp. homogeneous, free stability MT75.3 from phase .(Accelerat separation in any 41 A I Viscosity (temperature MT 192 80 cPs at 5C) Viscosity (temperature MT 192 35 cPs at 20C)

Performance Acceptable, as per above values

Example 5

The following composition was similar to example 1 except Exxate 700 (C6-8 branched alcohol, acetate ester) was used as the solvent.

Component Loading, CAS # Function Amount, g/L (Chemical name) S-(phenylmethyl) dipropylcarbamothioate Active e.g. Prosulfocarb (98.4% 52888- ingredient 3400.8 666.6 purity) 80-9 2,6-dinitro-N,N-dipropyl-4 (trifluoromethyl)benzenaminee.g. Active Trifluralin (95.6% ingredient 1301.6 247.3 purity) 1582

Exxate 700 90438- Solvent 262.8 49.9 79-2 Calcium dodecylbenzene sulfonate 26264- Surfactant 200.15 40.0 used: Ninate 60E (anionic 06-2 surfactant)

Ethoxylated tristyryl phenol used: Termul 3150 (non-ionic surfactant) 99734- Surfactant 200.8 40.2 09-5 Total, g 5366.2

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic Assay method (Accuracy: 98-102 %) 666.6 g/L (Linearity: R>0.99) (Precision: s/average <2%) Validated chromatographic Assay method (Accuracy: 98-102 %) 247.3 g/L (Linearity: R>0.99) (Precision: average <2%) pH at H MIT 75.3 7.89 1% aq. Solution

Specific gravity (temperature at CIPAC MT 3.1 1.073 20C) Emulsion CIPAC MT 36.1 Traces of oil characteristics Persistent CIPAC MT 47.2 25 mL Foaming Cold temp. Red clear liquid, stability homogeneous, free (Accelerat MT75.3 from phase ed Ageing) separation in any format Viscosity (temperature MT 192 105 cPs at 5C) Viscosity (temperature MT 192 37.5 cPs at 20C) Long Term Performance Acceptable, as per above values

Example 6 The following composition was similar to example 1 except that isophorone was used as the solvent.

Component Loading, (Chemical name) CAS # Function Amount, g/L g S-(phenylmethyl) dipropylcarbamothioate Active 52888-.3400664 e.g. Prosulfocarb(98.4% 80-9 ingredient purity)

2,6-dinitro-N,N-dipropyl-4 (trifluoromethyl)benzena mine Active e.g. Trifluralin (95.6%i 1301.35 247.3 purity) 1582 09-8

Isophorone 78-59-1 Solvent 299.85 60.0

Calcium dodecylbenzene sulfonate used: Ninate 60E (anionic 26264- Surfactant 201.45 40.3 surfactant) 06-2

Ethoxylated tristyryl phenol Surfactant 202.1 40.4 used: Termul 3150 (non-ionic surfactant) 99734 09-5 Total, g 540478

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic method Assay (Accuracy: 98-102%) 666.4 g/L (Linearity: R>0.99) (Precision: s/average <2%) Validated chromatographic method Assay (Accuracy: 98-102 %) 247.3 g/L (Linearity: R>0.99) (Precision: s/average <2%) pH at 100aq MT 75.3 7.89 1% aq. Solution Specific gravity 1.080 (temperature at 20C) CIPAC MT 3.1

Emulsion characteristics CIPAC MT 36.1 Traces of oil

Persistent Foaming CIPAC MT 47.2 35 mL

Cold temp. Red clear liquid, stability homogeneous, free (Accelerated from phase separation Ageing) in any format

Viscosity (temperature at 5C) MT 192 90 cPs

Viscosity (temperature at 20C) MT 192 40 cPs

Long Term Performance Acceptable, as per above values

Example 7 The following composition was similar to example 1 except methyl benzoate was used as the solvent.

Component Loading, (Chmiclnae)CAS # Function Amount, gg/ g/ (Chemical name) S-(phenylmethyl) dipropylcarbamothioate 52888-80-9 Active e.g. Prosulfocarb (98.4% ingredient 3420.75 670.5 purity)

2,6-dinitro-N,N-dipropyl 4- 1582-09-8 Active (trifluoromethyl)benzenami ingredient 1302.1 247.4 ne e.g. Trifluralin (95.6% purity)

Methyl Benzoate 93-58-3 Solvent 310.6 62.1

Calcium dodecylbenzene sulfonate used: Ninate 60E (anionic 26264-06-2 Surfactant 203.15 40.6 surfactant)

Ethoxylated tristyryl phenol used: Termul 3150 (non- 99734-09-5 Surfactant 204.55 40.9 ionic surfactant)

Total, g 5441.2

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic Assay method (Accuracy: 98- 670.5 g/L 102%) (Linearity: R>0.99) (Precision: s/average <2%) Validated chromatographic Assay method (Accuracy: 98- 247.4 g/L 102%) (Linearity: R>0.99) (Precision: s/average <2%) pH at MIT 75.3 7..96 1% aq. Solution

Specific gravity CIPAC MT 3.1 1.088 (temperature at 20C)

Emulsion c Erlsic CIPAC MT 36.1 Traces of oil characteristics Persistent Foaming CIPAC MT 47.2 25 mL

Coldtemp. Red clear liquid, homogeneous, free stability MT75.3 from phase (Accelerated (Accelerd separation in any Ageing) format

Viscosity (temperature at 5C)

Viscosity NT123 ~ (temperatureat 20C) MT192 38cPs

Perfor ne Acceptable, as per above values

Example 8 The following composition was similar to example 1 except N-methyl pyrrolidone was used as the solvent.

Component Loading, (Chmicl nme ~ CAS.u Function Amount, ,.g/ (Chemical name) S-(phenylmethyl) dipropylcarbamothioate 52888-80- Active e.g. Prosulfocarb(98.4% 9 ingredient 3409.3 673 purity)

2,6-dinitro-N,N-dipropyl-4 (trifluoromethyl)benzena 1582-09-8 Active mine ingredient 1310.6 250 e.g. Trifluralin (95.6% purity)

N-methyl Pyrrolidone 872-50-4 Solvent 323.9 65

Calcium dodecylbenzene sulfonate usedNinae60E26264-06- used: Ninate 60E2 Surfactant 248.25 49 (anionic surfactant) 2 Ethoxylated tristyryl phenol used: Termul 3150(non-ionic 99734-09 surfactant) 5 Total, g 5457.5

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic method Assay (Accuracy: 98-102%) 667.6 g/L (Linearity: R>0.99) (Precision: s/average Validated chromatographic method Assay (Accuracy: 98-102%) 247.2g/L (Linearity: R>0.99)

(Precision: s/average<2%) pH at 100aq MT 75.3 7.86 1% aq. Solution Specific gravity 1.088 (temperature at 20C) CIPAC MT 3.1

Emulsion CIPAC MT 36.1 0 mL of oil/cream characteristics Persistent Foaming CIPAC MT 47.2 28 mL

Cold temp. stability Red clear liquid, (Accelerated MT75.3 homogeneous, free from Ageing) phase separation in any format Viscosity (temperature at 5C) MT 192 63 cPs

Viscosity (temperature at 20C) MT 192 35 cPs

Long Term Performance Acceptable, as per above values

Example 9 The following composition was similar to example 1 except that propiophenone was used as the solvent.

Component CAS unction Amount, Loading, (Chemical name) Ag g/L S-(phenylmethyl) dipropylcarbamothioate 52888-80- Active e.g. Prosulfocarb (98.4% 9 ingredient 3401.1 666.6 purity) 2,6-dinitro-N,N-dipropyl -4 (trifluoromethyl)benzenamine 1582-09-8 Active e.g. Trifluralin (95.6% ingredient 1304.3 247.8 purity) Propiophenone 93-55-0 Solvent 296.05 59.2

Calcium dodecylbenzene sulfonate used: Ninate 60E (anionic 26264-06-2 Surfactant 212.15 42.4 surfactant) Ethoxylated tristyryl phenol 99734-09-5 used: Termul 3150 (non- Surfactant 201.4 40.3 ionic surfactant) Total, g 54T5.0

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic method (Accuracy: 98-102%) (Linearity: 666.6 g/L Assay R>0.99) (Precision: s/average <2%) Propiconazole

Validated chromatographic method (Accuracy: 98-102%) (Linearity: Assay R>0.99) (Precision: s/average <2%) 247.8 g/L

pH at MT 75.3 7.95 1% ag. Solution Specific gravity (temperature at CIPAC MT 3.1 1.082 C) Emulsion CIPAC MT 36.1 Traces of oil characteristics Persistent Foaming CIPAC MT 47.2 25 mL Cold temp. Red clearliquid, stability homogeneous, free (Accelerated MT75.3 from phase Ageing) separation in any format Viscosity (temperature at MT 192 63 cPs C) Viscosity (temperature at MT 192 35 cPs C) Long Term Performance Acceptable, as per above values

Example 10 The following composition was similar to example 1 except Recosol 200 (equivalent to Solvesso 200) was used as the solvent.

Component CAS # Function Amount Loading, (Chemical name) ,Ag g/L S-(phenylmethyl) dipropylcarbamothioate 52888-80- Active e.g. Prosulfocarb(98.4% 9 ingredient 3410.6 673 purity) 2,6-dinitro-N,N-dipropyl-4 (trifluoromethyl)benzena mine 1582-09-8 Active e.g. Trifluralin (95.6% ingredient 1305.8 249 purity)

20064742 Recosol 200 (high flashpoint 94-5 Solvent aromatic hydrocarbon solvent) 305 61

Calcium dodecylbenzene sulfonate 26264-06- Surfactant 202.8 40 used: Ninate 60E 2 (anionic surfactant)

Ethoxylated tristyryl phenol used: Termul 3150 99734-09- Surfactant 202.8 40 (non-ionic surfactant) 5

Total, g 5427

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic Assay method (Accuracy: 98- 667 g/L 102%) (Linearity: R>0.99) (Precision: s/average <2%)

Validated chromatographic Assay method (Accuracy: 98-102 247.5 g/L %) (Linearity: R>0.99) (Precision: s/average <2%) pH at 100aq MT 75.3 8.05 1% aq. Solution Specific gravity 1.082 (temperature at 20C) CIPAC MT 3.1

Emulsion characteristics CIPACMT36.1 0.1mLofoil Persistent Foaming CIPAC MT 47.2 28 mL

Coldtemp. Red clear liquid, stability homogeneous, free (Accelerated MT75.3 from phase Ageing) separation in any format Viscosity (temperature at MT 192 120 cPs C) Viscosity (temperature at MT 192 34 cPs 20C)

Long Term Performance Acceptable, as per above values

Example 11 The following composition was similar to example 1 except that Termul 200 was used as the non-ionic surfactant.

Component (Chemical name) CAS # Function Amount g Loading g/L

S-(phenylmethyl) dipropylcarbamothioate Active 52888-80-9 ingredient 3401 666.6 e.g. Prosulfocarb (98.4% purity) 2,6-dinitro-N,N-dipropyl 4- Active (trifluoromethyl)benzenam1582-09-8 ingredient 1308.9 248.7 ine e.g. Trifluralin(95.6% Recosol 150 64742-94-5 Solvent 369.9 74.0 Calcium dodecylbenzene used: Ninate 60 (anionic 26264-06-2 Surfactant 200.2 40.0 surfactant) Alkoxylated alkyl phenol used: Termul 37251-69-7 Surfactant 201.7 40.3 200 (non- ionic Total, g 5481.7

Parameter Method Results

Appearance Visual Red clear liquid Validated chromatographic method (Accuracy: 98-102%) Assay (Linearity: R>0.99) (Precision: 666.6g/L s/average <2%) Validated chromatographic method (Accuracy: 98-102%) (Linearity: R>0.99) (Precision: s/average <2%) pH at 1% aq. MT75.3 7.67 Solution Specific gravity 1.071 (temperature at CIPAC MT 3.1 20C)

Emulsion 1 mL of cream CIPAC MT 36.1 characteristics Persistent Foaming CIPAC MT 47.2 15 mL

Cold temp. Red clearliquid, stability homogeneous, free (Accelerated MT75.3 from phase Ageing) separation in any format Viscosity 74 cPs (temperature at 5C) MT 192

Viscosity 35 cPs (temperature at 20C) MT 192 Long Term Performance Acceptable, as per above values

Example 12 The following composition was similar to example 1 except that Termul 1285 was used as the non-ionic surfactant.

Component CAS # Function Amoun Loading, (Chemical name) t, g g/L

S-(phenylmethyl) 52888-80-9 Active dipropylcarbamothio . t 3406.5 672 ate e.g. Prosulfocarb Igreien (98.4% purity)

2,6-dinitro-N,N dipropyl-4- 1582-09-8 Active (trifluoromethyl)benze ingredient 1307 249 n amine e.g. Trifluralin (95.6% purity)

Recosol150 64742-94-5 Solvent 272.25 54

Calcium dodecylbenzene used: 26264-06-2 Surfactant 203.9 41 Ninate 60 (anionic surfactant)

Castor oil Ethoxylates used: Termul 1285 61791-12-6 Surfactant 203.9 41 (non-ionic surfactant)

Total, g

Parameter Method Results Appearance Visual Red~clear liquid Validated chromatographic method 667.6g/L Assay (Accuracy: 98-102%) (Linearity: R>0.99) (Precision: s/average <2%)

Validated chromatographic method Assay (Accuracy: 98-102%) (Linearity: 247.1 g/L R>0.99) (Precision: s/average <2%)

at pH pH 79 . MT 75.3 1% aq. Solution 15 Specific gravity CIPAC MT 3.1 (temperature at 20C)

Emulsion lmL of characteristics CIPAC MT 36.1 cream

Persistent Foaming CIPAC MT 47.2 n.a.

Cold temp. stability MT75.3 (Accelerated Ageing)

Viscosity MT 19292.5 (temperature at 5C)

. . 42.5 Viscosity MT 192 (temperature at 20C)

Long Term Performance Acceptable, as per above values

Example 13

The following composition was similar to example 1 except that Teric PE64 was used as the non-ionic surfactant.

Component CAS # Function Amount, Loading, (Chemical name) g g/L

S-(phenylmethyl) 52888 dipropylcarbamothioate 80-9 Active 3401.45 667.6 e.g. Prosulfocarb(98.4% ingredient purity)

2,6-dinitro-N,N-dipropyl-4 (trifluoromethyl)benzena mine 1582 e.g. Trifluralin (95.6% 09-8 Active 1302.9 247.1 purity) purity)ingredient

64742- Solvent 273.89 53.1 Recosol 150 94-5

Calcium dodecylbenzene 26264- Surfactant 200.05 40.5 used: Ninate 60(anionic 06-2 surfactant)

Block Co-polymer used: Teric PE64 (non- 9003- Surfactant 201.55 40.3 ionic surfactant) 11-6 Total,-g 5379.8

Parameter Method Results Appearance Visual Red dear liquid

Validated chromatographic method (Accuracy: 98-102%) 667.6g/L Assay (Linearity: R>0.99) (Precision: s/average <2%)

Assay Validated chromatographic method 247.1 g/L (Accuracy: 98-102%)

(Linearity: R>0.99) (Precision: s/average <2%) pH at MT 75.3 6.95 10 / 0 ao Solution Specific gravity 1.151 (temperature at CIPAC MT 3.1 20C) Emulsion CIPAC MT 36.1 2 mL cream, characteristics Persistent CIPAC MT 47.2 20 mL

Cold temp. Red clear liquid, stability homogeneous, (Accelerated MT75.3 free from phase Ageing) separation in any format Viscosity 117.5 cPs (temperature MT 192 at 5C) Viscosity 40 cPs (temperature MT 192 at 20C) Long Term Performance Acceptable, as per above values

Example 14 The following composition was similar to example 1 except that Termul 203 was used as the non-ionic surfactant.

Component . Amount Loading, (Chemical name) ,Ag g/L

S-(phenylmethyl) 52888-80-9 Active dipropylcarbamothio dt 3404.35 667.3 ate e.g. Prosulfocarb (98.4% purity)

Active 2,6-dinitro-N,N- 1582-09-8 1301.35 247.3 dipropyl-4- ingredient

(trifluoromethyl)benze n amine e.g. Trifluralin (95.6% purity)

64742-94-5 Solvent 284.8 57.0 Recosol150

Calcium dodecylbenzene used: 26264-06-2 Surfactant 206.05 41.2 Ninate 60 (anionic surfactant)

Alcohol alkoxylate Surfactant used: Termul 203 Proprietary 204.9 41.0 (non- ionic surfactant) Total,g 541.5

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic method (Accuracy: 98-102%) (Linearity: 667.3g/L Assay R>0.99) (Precision: s/average <2%)

Validated chromatographic method Assay (Accuracy: 98-102%) (Linearity: 247.3 g/L R>0.99) (Precision: s/average <2%)

pH at 1% aq. 7.68 Solution MT75.3 Specific gravity 1.081 (temperature at CIPAC MT 3.1 C) Emulsion characteristics CIPAC MT 36.1 1 mL cream

Persistent Foaming CIPAC MT 47.2 20 mL

Cold temp. Red clear liquid, stability MT75.3 homogeneous, free from phase

(Accelerat separation in any ed Ageing) format Viscosity 82.5 cPs (temperature MT 192 at 5C) viscosity 4-TS 40cPs (temperature at MT 192 20C) Lon Term Per ormance Acceptable, as per above values

Example 15 The following composition was similar to example 1 except that Kemmat HF60 was used as the anionic surfactant.

Component CAS # Function Amount Loading, (Chemical name) ,g g/L

S-(phenylmethyl) 52888-80-9 Active dipropylcarbamothioate ingredient 3412.7 668.9 e.g. Prosulfocarb (98.4%

2,6-dinitro-N,N dipropyl-4- 1582-09-8 Active (trifluoromethyl)benzena ingredient 1302.4 247.5 m inc e.g. Trifluralin

64742-94-5 Solvent 250.35 50.1 Recosol150

Calcium dodecylbenzene 26264-6-2 Surfactant 201.6 40.3 sulfonate - linear used: Kemmat HF 60

Ethoxylated tristyryl 99734-09-5 Surfactant 205.95 41.2 phenol used: Termul

Total, g 5373.0

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic method (Accuracy: 98-102%) 668.9g/L Assay (Linearity: R>0.99) (Precision: s/average <2%) Validated chromatographic Assay method (Accuracy: 98-102%) 247.5 g/L (Linearity: R>0.99) (Precision: s/average <2%) pH at 1% aq. MT 75.3 8.00 Specific gravity 1.074 (temperature at CIPAC MT 3.1 C) Emulsion characteristics CIPAC MT 36.1 Traces of cream Persistent CIPAC MT47.2 38 mL Fnmino Cold temp. Redclearliquid, stability homogeneous, MT75.3 free from (Accelerat ed Ageing) phase separation in Viscosity 95 cPs (temperature MT 192 at 5C) Viscosity 40 cPs (temperature MT 192 at 20C) Long~r Per ormance Acceptable, as per above values

Example 16 The following composition was similar to example 1 except that Rhodacal 70 was used as the anionic surfactant.

Component Amount, Loading, (Chemical name) CAS#Function g n g/L

S-(phenylmethyl) 52888 dipropylcarbamothioate e.g. 80-9 - Active 3403.7 667.1 Prosulfocarb (98.4% purity) ingredient

2,6-dinitro-N,N-dipropyl-4 (trifluoromethyl)benzen 1582 amine 09-8 Active 1305.2 248.0 e.g. Trifluralin (95.6% ingredient purity)

64742- Solvent 278.55 55.7 Recosol 150 94-5

Calcium dodecylbenzene sulfonate - branched used: 78-83- Surfactant 200.5 40.1 Rhodacal 70 (anionic 1 surfactant)

Ethoxylated tristyryl phenol used: Termul 99734- Surfactant 205.9 41.2 3150 (non-ionic 09-5 surfactant) Total, g 5393.9

Parameter Method Results Appearance Visual Red clear liquid

Validated chromatographic method (Accuracy: 98-102%) 667.1g/L Assay (Linearity: R>0.99) (Precision: s/average <2%)

Assay Validated chromatographic 248 g/L method (Accuracy: 98-102%)

(Linearity: R>0.99) (Precision: s/average <2%) pH at 8.04 1% aq. Solution Specific gravity 1.079 (temperature at CIPAC MT 3.1 C) Emulsion CIPAC MT 36.1 Traces of oil characteristics Persistent CIPAC MT 47.2 30mE Foaming Coldtemp. Red clearliquid, stability homogeneous, (Accelerated MT75.3 free from phase Ageing) separation in any format Viscosity 85 cPs (temperature MT 192 at 5C) Viscosity 35 cPs (temperature at MT 192 20C Long Term Performance Acceptable, as per above values

Example 17 The following composition was similar to example 1 except that Toximul Tans 8 was used as the anionic surfactant.

Component Function .CAS# Amoun Loading, (Chemical name) t, g g/L

S-(phenylmethyl) 52888-80 -9 Active dipropylcarbamothio .

ate e.g. Prosulfocarb ingredient 3406.6 665 (98.4% purity)

2,6-dinitro-N,N- Active ingredient dipropyl-4- 1582-09-8 1321.5 249

(trifluoromethyl)benzen amine e.g. Trifluralin(95.6% purity)

Recosol150 64742-94- Solvent 5 293 58

Alkyphenol ether sulfate/ tallowamine ethoxylated salts used: roprietar S05.7 1 Toximul TANS 8 y Surfactant (anionic surfactant)

Ethoxylated tristyryl phenol used: Termul 3150 (non- 99734-09 S 5 Surfactant205.7 41 ionic surfactant) Total, g 5432.45

Parameter Method Results Appearance Visual Redclear hqcuid Validated chromatographic method (Accuracy: 98-102%) (Linearity: 666.9g/L Assay R>0.99) (Precision: s/average <2%)

Validated chromatographic method Assay (Accuracy: 98-102%) (Linearity: 248.1 g/L R>0.99) (Precision: s/average <2%)

pH at 7.54 1% aq. Solution Specific gravity 71 (temperature at CIPAC MT 3.1 C) Emulsion . CIPAC MT 36.1 1 mL characteristics cream Persistent Foaming CIPAC MT 47.2 n.a

Cold temp. Red clear liquid, stability homogeneous, (Accelerat MT75.3 free from phase ed Ageing) separation in any format Viscosity 87.5 cPs (temperature MT 192 at 5C) Viscosity 38.8 cPs (temperature at MT 192 20C) Long Term Performance Acceptable, as per above values

Example 18 The following composition was similar to example 1 except that Termul 1284 was used as the non-ionic surfactant.

Component Function Amoun Loading, (Chemical name) t, g g/L S-(phenylmethyl) dipropylcarbamothioate 52888-80-9 Active 3402.1 673.6

e.g. Prosulfocarb(99% ingredient purity)

2,6-dinitro-N,N- Active dipropyl-4- 1582-09-8 1303.6 247.7 (trifluoromethyl)benzena ingredient mine e.g. Trifluralin (95% purity)

Solvent naphtha (netroleuml. heavy 64742-94-5 Solvent 91.1 58.2 aromatic e.g. Recosol 150 Calcium dodecylbenzene in 2-ethylhexanol e.g. 26264-06-2 Surfactant201.8 40.4 Ninate 60E (anionic in 104-76-7 surfactant)

Castor oil ethoxylate/ 61791-12-6 Surfactant 06.8 41.4 vegetable oil ethoxylate

e.g. Termul 1284 (non ionic surfactant 54U5-.T Total, g

Parameter Method Results

Appearance Visual

Validated chromatographic 673.6 g/L Assay method (Accuracy: 98-102 %) Prosulfoca (Linearity: R>0.99) (Precision: rb 247.7 s/average <2%) g/L pH at 10qoui CIPAC MT 75.3 7.43 1% aq. Solution Specific gravity (temperature at CIPAC MT 3.1 1.081 20C) Emulsion . CIPAC MT 36.1 1 mL of cream characteristics with traces of oil Persistent CIPAC MT 47.2 15 mL Foamin2 Orange clear Cold liquid, temp. CIPAC MT 39.3 homogeneous, stability free from phase (Accelerat separation in any ed format Viscosity (temperature CIPAC MT 192 104 cPs at 5C) Viscosity (temperature CIPAC MT 192 33 cPs at 20C) Long Term Per ormance Acceptable, as per above values

Example 19 The following composition was similar to example 1 except that Teric N8 was used as the non-ionic surfactant.

Component CAS # Function Amoun Loading, (Chemical name) t, g g/L S-(phenylmethyl) dipropylcarbamothioat Active 52888-80-9 . 3401.1 673.4 e ingredient e.g. Prosulfocarb(99%

2,6-dinitro-N,N dipropyl-4 (trifluoromethyl)benze Active namne1582-09-8 n ammne .gein ingredient 1301.9 247.4 e.g. Trifluralin (95% Solvent naphtha (petroleum), heavy 64742-94-5 Solvent 296.6 59.3 aromatic e.g. Recosol 150 Calcium dodecylbenzene in 2- 26264-06-2 ethylhexanol e.g. in 104-76-7Surfactant 201.4 40.3 Ninate 60E (anionic Nonyl Phenol Ethoxylate used: 9016-45-10 Surfactant 201.7 40.3 Teric N8 (non- ionic Total,'g " 54027T

Parameter Method Results

Appearance Visual Orange clear Validated chromatographic 673.4 g/L method (Accuracy: 98-102 %) Prosulfoca Assay (Linearity: R>0.99) (Precision: rb 247.4 s/average <2%) g/L pH at CIPAC MT 75.3 7.70 100aq.Solution

Specific gravity (temperature at CIPAC MT 3.1 1.080 C)

Emulsion . CIPAC MT 36.1 1 mL of cream characteristics with traces of oil Persistent CIPAC MT 47.2 20 mL Foamin2 Orange clear Cold liquid, temp. CIPAC MT 39.3 homogeneous, stability free from phase (Accelerat separation in any ed format Viscosity. (temperature CIPAC MT 192 128 cPs at 5C) Viscosity (temperature at CIPAC MT 192 35 cPs 20C) Lon erm Per rmance Acceptable, as per above values

Example 20 The following composition was similar to example 1 except that Teric N9 was used as the non-ionic surfactant.

Component Amount, Loading, (Chemical name) C gIL S-(phenylmethyl) 3401.2 673.4 dipropylcarbamothioate 52888- Active e.g. Prosulfocarb(99% 80-9 ingredient wiritvl~ 2,6-dinitro-N,N-dipropyl-4- 1582- Active 1300.6 247.1 (trifluoromethyl)benzenamine e.g. 09-8 ingredient Trifluralin (95% purity) Solvent naphtha (petroleum), heavy aromatic e.g. Recosol 150 64742- Solvent 291.2 58.2 94-5 Surfactant 201.8 40.4 Calcium dodecylbenzene in 2- 26264 ethylhexanol 06-2 e.g. Ninate 60E(anionic in 104 surfactant) 76-7

Nonyl Phenol Ethoxylate used: Teric N9 (non-ionic 9016-45-10 Surfactant 208.2 41.6 surfactant) Total, g 5403.0

Parameter Method Results Appearance Visual Orange clear liquid Validated 673.4 g/L chromatographic method Prosulfocarb Assay (Accuracy: 98-102 %) 247.1 g/L (Linearity: R>0.99) Trifluralin pH at CIPAC MT 75.3 7.10 1% an Solution Specific gravity (temperature at 20C) CIPAC MT 3.1 1.081

Emulsion 2 mL of cream with characteristics traces of oil Persistent Foaming CIPAC MT 47.2 20 mL Orange clear liquid, Cold temp. homogeneous, free from stability phase separation in any (Accelerated CIPAC MT 39.3 format Ageing)

Viscosity (temperature at CIPAC MT 192 100 cPs C) Viscosity (temperature at CIPAC MT 192 40 cPs C) Long Term Performance Acceptable, as per above values

Example 21 The following composition was similar to example 1 except that Teric N13 was used as the non-ionic surfactant. ComponentLodn (Chemicalname) CAS # (Chemicg Function Amount Loading, nae)g/L S-(phenylmethyl) dipropylcarbamothioate Active e.g. Prosulfocarb(99% 80-9 ingredient 3406.2 671 Purity) 2,6-dinitro-N dipropyl-4 (trifluoromethyl)benzen amine Active e.g. Trifluralin (95% 8 ingredient 1322.2 260 purity)

Solvent naphtha (petroleum), heavy aromatic 64742- Solvent 307.25 61 e.g. Recosol 150 94-5

Calcium dodecylbenzene in 2 ethylhexanol e.g. Ninate 60E 26264-06 (anionic surfactant) 2 in 104- Surfactant 283.39 56 76-7 Nonyl Phenol Ethoxylate used: Teric N13 (non- ionic surfactant) 9016-45- Surfactant 121.45 24 10 Total, g 5440.5

Parameter Method Results

Appearance Visual Orange clear liquid Validated chromatographic 673.5 g/L method (Accuracy: 98-102 %) Prosulfocarb Assay (Linearity: R>0.99) 247.8 g/L (Precision: s/average <2%) Trifluralin pH at H MIT 75.3 7.89 1% aq. Solution Specific gravity (temperature at CIPAC MT 3.1 1.082 C)

Emulsion characteristics CIPAC MT 36.1 0.2 mL of cream

Persistent CIPAC MT 47.2 35 mL Foamin2 Orange clear Cold temp. liquid, stability CIPAC MT 39.3 homogeneous, (Accelerat free from phase ed Ageing) separation in any format Viscosity (temperature CIPAC MT 192 102.5 cPs at 5C) Viscosity (temperature at CIPAC MT 192 35 cPs 20C) Long Term Performance Acceptable, as per above values

Example 22 The following composition was similar to example 1 except that Teric N15 was used as the non-ionic surfactant.

Component CAS # Function Amount, Loading, (Chemical name) 9 g/L S-(phenylmethyl) dipropylcarbamothioate Active 52888- .30. 7. e.g. Prosulfocarb(99% 80-9 ingredient purity) 2,6-dinitro-N,N-dipropyl-4 (trifluoromethyl)benzen amine e.g. Trifluralin (95% 1582- Active 1301.9 247.4 purity) 09-8 ingredient

Solvent naphtha (petroleum), heavy aromatic 64742- Solvent 300.5 60.1 e.g. Recosol 150 94-5

26264- Surfactant 201.0 40.2 Calcium dodecylbenzene 06-2

in 2-ethylhexanol e.g. Ninate 60E in 104

(anionic surfactant) 76-7

Nonyl Phenol Ethoxylate used: Teric N15 (non- ionic surfactant) 9016-45- Surfactant 201.1 40.2 10 Total, g 5406.2

Parameter Method Results

Appearance Visual Orange clear liquid Validated 673.5 g/L Assay chromatographic method Prosulfocarb (Accuracy: 98-102 %) 247.4 g/L (Linearity: R>0.99) Trifluralin pH at qoui CIPAC MT 75.3 7.10 1% aq. Solution Specific gravity (temperature at 20C) CIPAC MT 3.1 1.081

Emulsion CIPAC MT 36.1 2 mL of cream with traces characteristics of oil Persistent Foaming CIPAC MT 47.2 35 mL

Orange clear liquid, Coldtemp. homogeneous, free from stability CIPAC MT 39.3 phase separation in any (Accelerated format Ageing) Viscosity (temperature at CIPAC MT 192 82.5 cPs C) Viscosity (temperature at 20C) CIPAC MT 192 35 cPs Long Term Per ormance Acceptable, as per above values

Example 23 The following composition was similar to example 1 except that Ecoteric T20 was used as the non-ionic surfactant.

Component Loading (Chemical name) CAS# Function Amount g/L S-(phenylmethyl) dipropylcarbamothioate Active (99% 9 ingredient 3404.7 674 e.g. Prosulfocarb purity) 2,6-dinitro-N,N-dipropyl-4 (trifluoromethyl)benzena mine e.g. Trifluralin (95% 1582-09-8Active purity) ingredient 1301.05 249

Solvent naphtha (petroleum), heavy aromatic 64742-94- Solvent 296.7 59 e.g. Recosol 150 5

Calcium dodecylbenzene in 2 ethylhexanol 26264-06-Surfactant 244.3 49 e.g. Ninate 60E(anionic 2 in 104 surfactant) 76-7 Alkoxylated Sorbitan Monolaureate used: Ecoteric T20 (nonionic 9005-64-5 Surfactant 162.9 32 surfactant) Total, g 5409.7

Parameter Method Results

Appearance Visual Orange clear liquid Validated chromatographic method 674.2 g/L Assay (Accuracy: 98-102 %) (Linearity: Prosulfocarb 247.0 R>0.99) Precision: s/average <2%) g/L Trifluralin pH at .H aCIPAC MT 75.3 7.60 1% aq. Solution Specific gravity (temperature at CIPAC MT 3.1 1.081 20C) Emulsion CIPAC MT 36.1 2 mL of cream characteristics Persistent CIPAC MT 47.2 18 mL Foamin2 Orange clear Cold temp. liquid, stability CIPAC MT 39.3 homogeneous, (Accelerated free from phase Ageing) separation in any format Viscosity (temperature CIPAC MT 192 85 cPs at 5C Viscosity (temperature CIPAC MT 192 33 cPs at 20C) Lon Ierm Per ormance Acceptable, as per above values

Example 24 The following composition was similar to example 1 except that Terwet 3780 was used as the non-ionic surfactant.

Component CAS # Function Amount, Loading, (Chemical name) g g/L S-(phenylmethyl) dipropylcarbamothioate Active e.g. Prosulfocarb (99% 80-9 ingredient 3401.1 671 purity) 2,6-dinitro-N,N-dipropyl-4- Active (trifluoromethyl)benzenamine 1582- 1313.45 250 09-8 ingredients e.g. Trifluralin (95% purity) ~ Solvent naphtha (petroleum), 64742- Solvent 298.3 59 heavy aromatic 94-5 e.g. Recosol 150 Calcium dodecylbenzene in 2-ethylhexanol 26264-06-2 e.g. Ninate 60E (anionic in 104-76- Surfactant 241.68 48 surfactant) 7 Alkoxylated tallowamine used: Terwet 3780 (non- 9005-64-5 Surfactant 163.1 33 ionic surfactant) Total, g 5417.7

Parameter Method Results

Appearance Visual Orange clear liquid Validated 673.6 g/L Assay chromatographic method Prosulfocarb (Accuracy: 98-102 %) 247.7 g/L (Linearity: R>0.99) Trifluralin pH at qoui CIPAC MT 75.3 7.50 1% aq. Solution Specific gravity (temperature at 20C) CIPAC MT 3.1 1.080

Emulsion CIPAC MT 36.1 2 mL of cream characteristics Persistent Foaming CIPAC MT 47.2 10 mL

Orange clear liquid, Coldtemp. homogeneous, free from stability CIPAC MT 39.3 phase separation in any (Accelerated format Ageing)

Viscosity (temperature at CIPAC MT 192 130 cPs C) Viscosity (temperature at CIPAC MT 192 35 cPs C) Long Term Performance Acceptable, as per above values

Example 25 The following composition was similar to example 1 except that the ratio of prosulfocarb to trifluralin was 700:251.

Component CAS # Function Amount, Loading (Chemical name) g g/L S-(phenylmethyl) dipropylcarbamothioate Active 52888- .37 0. e.g. Prosulfocarb (98.4% 80-9 ingredient purity) 2,6-dinitro-N,N-dipropyl-4 (trifluoromethyl)benzenamine Active e.g. Trifluralin (95.6% 09-8 ingredient 1325 251.8 purity)

Solvent Naphtha (e.g. 64742- Solvent 160 32.0 Recosol 150) 945

Calcium dodecylbenzene sulfonate e.g. Ninate 60 (anionic 26264- Surfactant 216 43.2 surfactant) 06 2/104 Ethoxylated tristyryl phenol e.g. Termul 3150 (non-ionic 99734- Surfactant 175 35.0 surfactant) 09-5 Total,g 5451.0

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic Assay method (Accuracy: 98-102 %) 712.0 g/L (Linearity: R>0.99) (Precision: s/average <2%)

Assay Validated chromatographic 257.0 g/L method (Accuracy: 98-102%)

(Linearity: R>0.99) (Precision: s/average <2%) pHat H MIT 75.3 6.94 1% aq. Solution Specific gravity 1.069 (temperature at CIPAC MT 3.1 C) Emulsion characteristics CIPAC MT 36.1 Traces of oil

Persistent CIPAC MT 47.2 Foaming

Cold temp. Red clear liquid, stability homogeneous, (Accelerated MT75.3 free from phase Ageing) separation in any format Viscosity (temperature at MT 192 110 cPs C) Viscosity (temperature at MT 192 48 cPs C) Long Term Performance Acceptable, as per above values

Example 26

The following composition was similar to example 1 except that the ratio of prosulfocarb to trifluralin was about 720:251.

Component CAS # Function Amount, Loading, (Chemical name) g g/L S-(phenylmethyl) dipropylcarbamothioate Active 52888- .38. 2. e.g. Prosulfocarb (98.4% 80-9 ingredient purity) 2,6-dinitro-N,N-dipropyl-4 (trifluoromethyl)benzenamine Active 1582- .12. 5. e.g. Trifluralin (95.6% 09-8 ingredient purity)

64742-94-5 Solvent 53.05 10.6 Solvent Naphtha (e.g. Recosol150)

Calcium dodecylbenzene 43.1 sulfonate e.g. Ninate 60(anionic 26264-06- Surfactant 215.35 2/104-76-7 surfactant)

Ethoxylated tristyryl phenol e.g. Termul 3150 99734-09-5 Surfactant 180.15 36.0

Total, g 5453.1

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic Assay method (Accuracy: 98-102 %) 734.0 g/L (Linearity: R>0.99) (Precision: s/average<2%) Validated chromatographic Assay method (Accuracy: 98-102 %) 254.0 g/L (Linearity: R>0.99) (Precision: s/average <2%) pH at .t MT 75.3 6.95 1% aq. Solution Specific gravity 1.090 (temperature at CIPAC MT 3.1 C) Emulsion chrc.sic CIPAC MT 36.1 Traces of oil characteristics

Persistent CIPAC MT 47.2 Foaming Cold Red clear liquid, homogeneous, free stability MT75.3 from phase (Accelerat separation in any format ed

Viscosity (temperature MT 192 53 cPs at 5C) Viscosity (temperature at MT 192 118 cPs 20C) Long Term Performance Acceptable, as per above values

Example 27 The following composition was similar to example 1 except that the ratio of prosulfocarb to trifluralin was about 670:275.

Component . Amoun Loading, (Chemical name) AS# Function t, g g/L S-(phenylmethyl) dipropylcarbamothioate Active e.g. Prosulfocarb (98.4% 52888-80-9 ingredient purity) 2,6-dinitro-N,N-dipropyl 4- Active (trifluoromethyl)benzenami 1582-09-8 ingredient 1451.2 275.7 ne _ _ Triflnr-lin

Solvent Naphtha (e.g. Recosol 150) 64742-94-5Solvent 205.2 41.0

Calcium dodecylbenzene sulfonate 26264-06 e.g. Ninate 60 2/104-76-7 Surfactant221.3 44.3 (anionic Ethoxylated tristyryl phenol e.g. Termul 3150 99734-09-5 Surfactant 175.45 35.1 (non-ionic surfactant) Total, g 5462.4

Parameter Method Results Appearanc Visual Red clear liquid

Validated chromatographic Assay method (Accuracy: 98-102 %) 681.0 g/L (Linearity: R>0.99) (Precision: s/average <2%) Validated chromatographic Assay method (Accuracy: 98-102 %) 283.0 g/L (Linearity: R>0.99) (Precision: s/average <2%) pH at H MIT 75.3 6.85 1% aq. Solution Specific gravity 1.022 (temperature at CIPAC MT 3.1 20C) Emulsion characteristics CIPAC MT 36.1 Traces of oil

Persistent CIPAC MT 47.2 Foamin2 Coldtemp. Red clear liquid, Cobltemp. homogeneous, free sAbilt. MT75.3 from phase (Aceleratd separation in any Ageing) format Viscosity (temperature MT 192 83 cPs at 5C) Viscosity (temperature at MT 192 43 cPs 20C) Long Term Performance Acceptable, as per above values

Example 28 The following composition was similar to example 1 except that the ratio of prosulfocarb to trifluralin was about 670:300.

Component tAN I runcuon Amount, Loading, (Chemical name) g g/L

S-(phenylmethyl) dipropylcarbamothioate Active e.g. Prosulfocarb (98.4% 52888-80-9 ingredient3401.0 666.6 purity) 2,6-dinitro-N,N-dipropyl 4- 15208 Acie 17. (trifluoromethyl)benzenami 1582-09-8 Active 1576.4 299.5 ne e.g. Trifluralin (95.6% ingredient purity)

Solvent Naphtha (e.g. Recosol 150) 64742-94-5 Solvent 127.6 24.2

Calcium dodecylbenzene sulfonate 26264-06 e.g. Ninate 60 (anionic 2/104-76-7 Surfactant217.7 43.5 surfactant) Ethoxylated tristyryl phenol e.g. Termul 3150 99734-09-5 Surfactant 177.9 35.6 (non-ionic surfactant) Total,g 5500.6

Parameter Method Results Appearance Visual Red clear liquid Validated chromatograp hic method (Accuracy: Assay 98-102o%) 680.0 g/L (Linearity: R>0.99) (Precision: s/average <2%) Validated chromatograp Assay hic method 308.0 g/L (Accuracy: 98 102O%)

(Linearity: R>0.99) (Precision: average pH at H aMT 75.3 6.85 1% aq. Solution Specific gravity 1.099 (temperature at CIPAC MT 3.1 20C) Emulsion characteristics CIPAC MT 36.1 Traces of oil

Persistent CIPAC MT 47.2 Foamin2 Red clear liquid, homogeneous, stability . Coablt (Accelerat MT75.3 free from phase separation in any ed Ageing) format Viscosity (temperature MT 192 58 cPs at 5C) Viscosity (temperature MT 192 139 cPs at 20C)

Long Term Acceptable, as Performance per above values

Example 29 The following composition was similar to example 1 except that the ratio of prosulfocarb to trifluralin was about 670:350.

Component . Amount Loading, (Chemical name) CAS# Function ,mg t g/L S-(phenylmethyl) dipropylcarbamothioate Active 52888-80-9.3480 699 e.g. Prosulfocarb ingredient (98.4%Purity)

2,6-dinitro-N,N-dipropyl- Active 4- 1795.00 341.1 (trifluoromethyl)benzenami 1582-09-8 ingredient ne e.g. Trifluralin

Solvent Naphtha (e.g. Recosol 150) 64742-94-5 Solvent 38.95 7.8

Calcium dodecylbenzene sulfonate 26264-06 e.g. Ninate 60 (anionic 2/104-76-7 Surfactant 151.55 30.3 surfactant) Ethoxylated tristyryl phenol e.g. Termul 3150 99734-09-5 Surfactant 152.851 30.6 (non-ionic surfactant) Total, g 5556.4

Parameter Method Results Appearance Visual Red clear liquid Validated chromatographic Assay method (Accuracy: 98-102 %) 680.0 g/L (Linearity: R>0.99) (Precision: s/average <2%) Validated chromatographic Assay method (Accuracy: 98-102 %) 356.0 g/L (Linearity: R>0.99) (Precision: s/average <2%) pH at .t MT 75.3 7.07 1% aq. Solution Specific gravity (temperature at CIPAC MT 3.1 C) Emulsion chrc.sic CIPAC MT 36.1 1mL of oil characteristics Persistent CIPAC MT 47.2 Foaming

Red dear liquid, Coablt . homogeneous, sabilt MT75.3 free from phase (dAeierat separation in any ed Ageing) format Viscosity (temperature MT 192 153 cPs at 5C) Viscosity (temperature at MT 192 55 cPs 20C) Lon germ Per ormance Acceptable, as per above values

Example 30 One small plot replicated field trial was conducted between May and September 2016 to investigate the formulation of Example 1(hereinafter referred to as Formulation A) as an IBS treatment in a commercial wheat crop targeting annual ryegrass. The trial was conducted near East Wubin, Western Australia.

Site Details

Location East Wubin, Western Australia Crop variety Wheat, var. Zen Soil type Grey sandy loam Site history Lupin 2015 Sowing date 4 May 2016 Sowing rate 50 kg/ha Crop 2 L/ha of Glyphosate 450 prior to seeding. management

The following treatments were evaluated:

Tmt Treatment description /ha)

1 Untreated Control 2 Formulation A 1.0 3 Formulation A 15T

4 Formulation A 2.25 Formulation A 3 6 Formulation A 6

Jetti Duo* (commercial 1.8 7 standard) IMTRADE JETTI DUO (APVMA No. 68009) - An emulsifiable concentrate formulation containing 550 g/L tri-allate and 350 g/L trifluralin as marketed by Imtrade Australia Pty. Ltd.

Treatments were applied using a motorised hand operated boom spray incorporating Hardi Flat Fan 110015 nozzles. At an application speed of 2 metres per second and a pressure of 150 kPa, treatments were applied in a total volume of 94 L/ha. The treatments were applied by broadcast application.

Treatment Method

Equipment Motorised hand operated boom spray Method Broadcast Nozzles Hardi 110015 flat fan Nozzle spacing 50cm Pressure 150kpa Water volume 94 L/ha. Speed 2 m/s Boom height 50cm Application Timing IBS The trial site was sown with a farmer operated commercial Ausplow DBS 300 air seeder fitted with knife points and trailing press wheels. Sowing rate was 50 kg/ha wheat var. Zen.

Application Details No. of Applications One Date and time 4 May 2016, 12:00-13:30 Crop growth stage Z 00 Temperature 22°C Relative humidity 44% Cloud cover 0% Wind SE at 11-13 km/hr Soil moisture Dry surface, full profile

Trial rainfall Month Mm Month Mm May 46.2 August 39.2 June 41.2 September 14.0 July 42.2

The trial was established as a randomised complete block design with 7 treatments and 3 replicates. Plot size was 10 metres by 2 metres.

The pest species present at the trial site was annual ryegrass (Lolium rigidum). The trial commenced in a bare fallow paddock with 20% standing lupin stubble load.

Detailed assessments were conducted at 27, 47, 60 and 136 days after treatment (DAT). These included crop emergence counts, weed counts and weed panicle counts.

Weed counts - Count the number of annual ryegrass plants per plot from 3 randomly thrown 1xim quadrats. Present as the number of weeds per m 2

Crop emergence counts - count the number of emerged wheat plants of 3 randomly selected meters of row. Present as emerged seedlings per meter of row.

Weed panicle counts - count the number of annual ryegrass panicles (seed heads) per plot from 3 randomly thrown 1xm quadrats. Present as the number of panicles per m.

Statistical analyses were conducted using Microsoft Excel 2010, utilising the DSAASTAT ver. 1.101 plugin.

The model includes all treatment effects. Analysis of variance (ANOVA) was used for the analysis of treatment effects on non-transformed data with least significant difference (LSD) procedures used for means comparisons.

RESULTS AND DISCUSSION

Results are summarised in Tables 1-3.

Table 1

Analysis of treatment means; Mean number of wheat var. Zen seedlings per meter of row.

Applicati No. Treatment on rate 27 DAT (L/ha) 1/06/2016 1 Untreated 0 29.1 2 Formulation A 1 27.6 3 Formulation A 1.5 25.2 4 Formulation A 2.25 26.0 5 Formulation A 3 26.9 6 Formulation A 6 25.4 7 IMTRADE JETTI DUO 1.8 23.9 P value 0.825 LSD NS NS - no statistical significance at p <0.05

The emergence of wheat var. Zen was not affected by the application of Formulation A or IMTRADE JETTI DUO at any application rate. No significant difference in germination was noted between any rate of Formulation A when compared to either the untreated control or the commercial standard IMTRADE JETTI DUO.

Table 2 Analysis of treatment means; Mean number of annual ryegrass plants per m2

. Application No. Treatment rate 27 DAT 47 DAT 60 DAT (L/ha) 1/06/2016 21/06/2016 6/07/2016 1 Untreated 0 248.7 d 509.2 e 419.3 e 2 Formulation A 1 61.2 bc 138.1 d 196.6 c 3 Formulation A 1.5 71.8 c 153.0 d 256.3 d 4 Formulation A 2.25 44.6 b 63.3 bc 109.7 b Formulation A 3 25.7 a 54.0 ab 77.1 a 6 Formulation A 6 15.1 a 41.1 a 68.1 a IMTRADE 7 JETTI DUO 1.8 45.7 b 80.7 c 116.2 b

P value <0.001 <0.001 <0.001

LSD 48.686 4.231 75.224

Means within the same cell with a letter in common are not significantly different (P>0.05)

Formulation A at all rates and IMTRADE JETTI DUO provided statistically significant control of annual ryegrass plants in comparison to the untreated control. Formulation A at rates of 3 and 6 L/ha provided statistically significant control of annual ryegrass plants compared to IMTRADE JETTI DUO at all timings. Formulation A at a rate of 2.25 L/ha at all timings and at 1 L/ha at 27 DAT provided equivalent control of annual ryegrass plants compared to 1.8 L/ha of IMTRADE JETTI DUO. Formulation A demonstrated a clear rate response to annual ryegrass control at all timings, achieving maximum control at rates of 3 and 6 L/ha.

Table 3 Analysis of treatment means; mean number of annual ryegrass panicles per n.

Applicati No. Treatment on rate 136 DAT (L/ha) 20/09/2016 1 Untreated 0 173.7 d 2 Formulation A 1 78.8 c 3 Formulation A 1.5 75.2 c 4 Formulation A 2.25 64.7 bc 5 Formulation A 3 45.0 a 6 Formulation A 6 47.3 ab 7 IMTRADE JETTI DUO 1.8 49.7 ab P value <0.001 LSD 28.380 Means within the same cell with a letter in common are not significantly different (P>0.05)

Formulation A provided a statistically significant reduction in the number of annual ryegrass panicles present at 136 DAT at all application rates compared to the untreated control. Formulation A at application rates of 2.25, 3 and 6 L/ha provided an equivalent reduction in the number of annual ryegrass panicles present at 136 DAT compared to 1.8 L/ha of IMTRADE JETTI DUO. Formulation A exhibited a clear rate response as assessed by the number of annual ryegrass panicles present at 136 DAT. The largest reduction in panicle numbers was observed in the 3 and 6 L/ha treatments.

Formulation A clearly demonstrates efficacy on annual ryegrass at all rates applied compared to the untreated control. Formulation A provides equivalent or statistically significant control of annual ryegrass at application rates of 2.25, 3 and 6 L/ha compared to the control achieved by 1.8 L/ha of IMTRADE JETTI DUO. Formulation A exhibits a clear rate response when used for annual ryegrass control.

Formulation A did not adversely affect the germination of wheat var. Zen as demonstrated by crop emergence counts.

CONCLUSION

Formulation A clearly demonstrates efficacy on annual ryegrass at all rates applied compared to the untreated control. Formulation A provides equivalent or statistically significant control of annual ryegrass at application rates of 2.25, 3 and 6 L/ha compared to the control achieved by 1.8 L/ha of IMTRADE JETTI DUO. Formulation A exhibits a clear rate response when used for annual ryegrass control.

Formulation A did not adversely affect the germination of wheat var. Zen as demonstrated by crop emergence counts.

Claims (26)

Claims

1. An emulsifiable concentrate formulation including: prosulfocarb; trifluralin; and at least one agriculturally acceptable surfactant, wherein the sum of concentrations of prosulfocarb and trifluralin in the emulsifiable concentrate formulation is greater than 600 g/L.

2. The emulsifiable concentrate formulation of claim 1, wherein prosulfocarb and trifluralin are present in a weight ratio in the range of about 5:1 to about 1:1.

3. The emulsifiable concentrate formulation of claim 2, prosulfocarb and trifluralin are present in a weight ratio in the range of about 3.5:1 to about 2:1.

4. The emulsifiable concentrate according to any one of the preceding claims, wherein prosulfocarb is present at a concentration of about 500 to about 900 g/L and trifluralin is present at a concentration of about 100 to about 400 g/L.

5. The emulsifiable concentrate formulation according to any one of the preceding claims, wherein a weight ratio of a herbicidal component consisting of prosulfocarb and trifluralin to a non-herbicidal component comprising the surfactant is at least 4:1.

6. The emulsifiable concentrate formulation according to any one of the preceding claims, further comprising at least one agriculturally acceptable solvent.

7. The emulsifiable concentrate formulation of claim 6, wherein the weight ratio of the herbicidal component to the agriculturally acceptable solvent is at least 6:1.

8. The emulsifiable concentrate formulation of claim 6 or claim 7, wherein the agriculturally acceptable solvent is selected from the group consisting of aliphatic paraffin oils, aromatic solvents, C6-C18 aromatic solvents, chlorinated hydrocarbons, alcohols, ketones, ethers, esters, vegetable oils, methylated vegetable oils, petroleum fractions, sugar esters of fatty acids, alkane compounds, aryl compounds, alkylaryl compounds, heterocyclic compounds, lactams, amides, xylene, toluene, pyrrolidones, substituted pyrrolidones, glycol ethers, end-capped glycol ethers and any combination thereof

9. The emulsifiable concentrate formulation of claim 8, wherein the agriculturally acceptable solvent is selected from the group consisting of ketones, esters, petroleum fractions, optionally substituted pyrrolidones and any combination thereof

10. The emulsifiable concentrate formulation according to any one of the preceding claims, wherein the at least one agriculturally acceptable surfactant is selected from the group consisting of a non-ionic surfactant, an anionic surfactant, a cationic surfactant, a zwitterionic surfactant, an anion-cation composite surfactant and any combination thereof

11. The emulsifiable concentrate formulation of claim 10, wherein the at least one agriculturally acceptable surfactant is or comprises an non-ionic surfactant selected from the group consisting of alkoxylated block polymers, alkoxylated alcohols, alkoxylated alkylphenols, alkoxylated monostyryl phenols, alkoxylated distyryl phenols, alkoxylated tristyryl phenols, alkoxylated amines, alkoxylated amides, alkoxylated fatty esters, alkoxylated fatty acids and any combination thereof

12. The emulsifiable concentrate formulation of claim 10, wherein the non ionic surfactant is selected from the group consisting of alkoxylated alcohols, alkoxylated alkylphenols, castor oil ethoxylates, ethoxylated tallow amines, polyoxyethylene sorbitan monolaurate, ethylene oxide-propylene oxide block copolymers, alkoxylated monostyryl phenols, alkoxylated distyryl phenols, alkoxylated tristyryl phenols and any combination thereof

13. The emulsifiable concentrate formulation of claim 11, wherein the non ionic surfactant is selected from the group consisting of alkoxylated alcohols, nonylphenol alkoxylates, castor oil ethoxylates, ethoxylated tallow amines, polyoxyethylene sorbitan monolaurate, ethylene oxide-propylene oxide block copolymers, ethoxylated tristyryl phenols and any combination thereof

14. The emulsifiable concentrate formulation of any one of claims 10 to 14, wherein the non-ionic surfactant is present in an amount of about 10 to about 80 g/L in the formulation.

15. The emulsifiable concentrate formulation of claim 10 wherein the at least one agriculturally acceptable surfactant is or comprises an anionic surfactant selected from the group consisting of alkyl or aryl or alkylaryl or alkylether sulfates, alkyl or aryl or alkylaryl sulfonates, alkyl or aryl or alkylaryl ether phosphates, alkyl carbonates and sarcosinates, carboxylated alkylphenols, carboxylated alcohol derivatives, sulfates or sulfonates of alkoxylated moieties, sulfonates of naphthalene or alkylnaphthalene or petroleum, and any combination thereof

16. The emulsifiable concentrate formulation of claim 15, wherein the anionic surfactant is or comprises a calcium alkylbenzene sulfonate salt.

17. The emulsifiable concentrate formulation of claim 15 or 16, wherein the anionic surfactant is present in a concentration of about 15 to about 70 g/L.

18. The emulsifiable concentrate formulation of claim 10, wherein the at least one agriculturally acceptable surfactant is or comprises an anion-cation composite surfactant selected from the group consisting of alkylphenol ether sulfate/tallow amine ethoxylate salts, alcohol ether sulfate/tallow amine ethoxylate salts and dodecylbenzenesulfonic acid/ethoxylated alkylamine salts.

19. The emulsifiable concentrate formulation of claim 18, wherein the anion cation composite surfactant is or comprises an alkylphenol ethersulfate/tallow amine ethoxylate.

20. The emulsifiable concentrate formulation according to any one of the preceding claims, wherein the formulation comprises at least two agriculturally acceptable surfactants and wherein the at least two agriculturally acceptable surfactants include at least one anionic surfactant and at least one non-ionic surfactant.

21. A method of preparing a emulsifiable concentrate formulation as claimed in any one of claims 1 to 20, including the steps of: (a) adding prosulfocarb to a vessel; (b) adding trifluralin to the vessel; (c) adding at least one agriculturally acceptable surfactant to the vessel, and (d) mixing the prosulfocarb, trifluralin and the agriculturally acceptable surfactant to thereby prepare the emulsifiable concentrate formulation.

22. The method of claim 21, further including the step of adding at least one agriculturally acceptable solvent to the vessel.

23. An emulsifiable concentrate formulation prepared by the method of Claim 21 or Claim 22.

24. A stable emulsion produced by mixing an emulsifiable concentrate formulation of prosulfocarb and trifluralin according to any one of claims 1 to 20 and 23 with water.

25. A method of controlling weeds in a target crop including the step of applying an effective amount of a dilute form of the emulsifiable concentrate formulation of any one of claims 1 to 20 and 23 to the target crop to thereby control said weeds.

26. A method of controlling weeds in a target crop including the step of applying an effective amount of the stable emulsion of claim 24 to the target crop to thereby control said weeds.