AU2018229453B2 - Pyrethroid formulation - Google Patents

Abstract

Provided is an emulsifiable and/or dispersible concentrate formulation that includes alpha-cypermethrin at a concentration of at least 5 about 125 g/L, a surfactant and two or more solvents and methods of making same. Methods of preventing and/or controlling pest infestations by applying a pesticidally effective amount of the emulsifiable and/or dispersible concentrate formulation of alpha-cypermethrin to a target area are also provided. 10 54

Description

PYRETHROID FORMULATION FIELD OF THE INVENTION

This invention relates to a pyrethroid formulation. In particular, the

present invention relates to an emulsifiable and/or dispersible concentrate

formulation of alpha-cypermethrin that contains a high level of alpha

cypermethrin as active agent and to methods of preparing and using said

formulation.

BACKGROUND TO THE INVENTION

Cypermethrin is a highly active synthetic pyrethroid insecticide,

effective against a wide range of pests in agriculture, public health and

animal husbandry. Alpha-cypermethrin is an isomeric subset of

cypermethrin and a well-established insecticidal agent in its own right.

Alpha-cypermethrin is a contact insecticide that controls a broad

range of insects through contact and stomach action following ingestion of

treated material. To this end, the insecticide function as a neuropoison

acting on axons in the peripheral and central nervous systems by

interacting with sodium channels in insects.

Alpha-cypermethrin can be applied in diverse settings, including

broad acre cropping (cereals, oilseeds, legumes, cotton, etc.), horticulture

(vegetables, stone-fruit, pome-fruit, etc.), viticulture and forestry uses. In

this respect, alpha-cypermethrin is typically applied to a target area in the form of a diluted concentrate.

Notwithstanding the commercial availability of a range of alpha-cypermethrin

formulations, there remains a need for an emulsifiable and/or dispersible concentrate

formulation thereof that overcomes one or more of the inherent limitations of

commercially available alpha-cypermethrin formulations.

SUMMARY OF THE INVENTION

In one aspect of the invention, there is provided an emulsifiable and/or

dispersible concentrate formulation comprising:

alpha-cypermethrin at a concentration of at least about 125 g/L;

a surfactant; and

two or more solvents selected from the group consisting of: a heavy aromatic

solvent naphtha (petroleum), a pyrrolidone, methyl benzoate, ethyl benzoate,

caprolactone and any combination thereof.

In another aspect of the invention, there is provided method of preparing an

emulsifiable and/or dispersible concentrate alpha-cypermethrin formulation including

the steps of:

(a) combining alpha-cypermethrin, a surfactant and two or more solvents

selected from the group consisting of: a heavy aromatic solvent naphtha (petroleum),

a pyrrolidone, methyl benzoate, ethyl benzoate, caprolactone and any combination

thereof, wherein alpha-cypermethrin is present at a concentration of at least about 125

g/L; and

(b) mixing the mixture of step (a) to thereby prepare the emulsifiable and/or

dispersible concentrate alpha-cypermethrin formulation.

In a first aspect, the invention provides an emulsifiable and/or dispersible concentrate

formulation comprising:

alpha-cypermethrin at a concentration of at least about 125 g/L;

a surfactant; and

two or more solvents.

In certain embodiments, alpha-cypermethrin is present at a concentration of at

least about 200 g/L of the total weight of the formulation.

Suitably, the two or more solvents are present in an amount of at least about

500 g/L. Preferably, the two or more solvents are present in an amount ranging

between about 500 g/L to about 800 g/L.

At least one of the two or more solvents is suitably selected from the group consisting

of an aromatic hydrocarbon, a lactam, an alkyl benzoate, a lactone and any

combination thereof. Preferably, at least one of the two or more solvents are selected

from the group consisting of a

2a heavy aromatic solvent naphtha (petroleum), a pyrrolidone, methyl benzoate, ethyl benzoate, caprolactone and any combination thereof. In particular preferred embodiments, the pyrrolidone is N-methyl pyrrolidone and/or octyl-pyrrolidone.

Suitably, the two or more solvents comprise first and second

solvents. Preferably, the first solvent is selected from the group consisting

of a lactam, a lactone, and any combination thereof and/or the second

solvent is selected from the group consisting of an aromatic hydrocarbon,

an alkyl benzoate and any combination thereof. In particular embodiments,

the ratio of the first solvent to the second solvent is in the range of about

3:1 to about 1:3.

The surfactant is suitably present in an amount of at least about 40

g/L. Preferably, the surfactant is present in an amount ranging between

about 50 g/L to about 150 g/L.

In one embodiment, the surfactant is selected from the group

consisting of an alkoxylated oil, an alkylphenol alkoxylate, an alkoxylated

alcohol, an alkoxylated polyaryl phenol, an alkoxylated block co-polymer,

an alkylbenzenesulphonate, such as calcium alkylbenzenesulphonate, an

alcohol ether sulphate, an alkylamine ethoxylate and any combination

thereof. More preferably, the surfactant is selected from the group

consisting of an ethoxylated castor oil, an ethoxylated nonylphenol, an

ethoxylated alcohol, an ethoxylated tristyrylphenol, an ethoxylate

propoxylate copolymer, a C10-16 alkylbenzenesulphonate (branched or linear in solvent), a branched alcohol ether sulphate, a tallow amine alkoxylated salt and any combination thereof.

In one embodiment, the surfactant comprises a non-ionic surfactant

and/or an anionic surfactant.

In a second aspect, the invention provides a method of preparing

an emulsifiable and/or dispersible concentrate alpha-cypermethrin

formulation including the steps of:

(a) combining alpha-cypermethrin, a surfactant and two or more

solvents, wherein alpha-cypermethrin is present at a concentration of at

least about 125 g/L; and

(b) mixing the mixture of step (a) to thereby prepare the emulsifiable

and/or dispersible concentrate alpha-cypermethrin formulation.

For the present aspect, the emulsifiable and/or dispersible

concentrate alpha-cypermethrin formulation is suitably that of the first

aspect.

In a third aspect, the invention provides an emulsifiable and/or

dispersible concentrate alpha-cypermethrin formulation prepared by the

method of the second aspect.

In a fourth aspect, the invention provides a method of preventing

and/or controlling a pest infestation in a target area, including the step of

applying a pesticidally effective amount of the emulsifiable and/or

dispersible concentrate formulation of the first or third aspects mixed with

water or a water-containing liquid to the target area to thereby prevent and/or control the pest infestation.

In one embodiment, the method of the present aspect further

includes the initial step of mixing the emulsifiable and/or dispersible

concentrate formulation with water or the water-containing liquid.

As used herein, except where the context requires otherwise, the

term "comprise" and variations of the term, such as "comprising",

"comprises" and "comprised", are not intended to exclude further

elements, components, integers or steps but may include one or more

unstated further elements, components, integers or steps.

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.

DETAILED DESCRIPTION OF THE INVENTION

There is an advantage in providing pesticide products in a

condensed or highly loaded form having a high concentration of active

ingredient/s. By way of example, the treatment of a given volume of

produce or target area (e.g., crop, land, commercial or residential

premises etc) can be achieved with a reduced amount of pesticide product

being used. As such, these highly loaded pesticide products afford a

broadly better economic outcome together with reduced costs (e.g., non active ingredient, packaging, handling, storage, freight, labour, regulatory licensing and disposal costs) and less environmental impact (e.g., reduced non-active ingredients, such as solvents, surfactants, preservatives, anti oxidants, dyes and consumption deterrents, and packaging, such as containers, closures, labels/booklets, pallets and pallet liners/boxes/wrapping).

In addition to the above, providing an emulsifiable and/or

dispersible concentrate form of a pesticide product rather than as a

suspension concentrate form, further alleviates some or all of the

deficiencies of the latter. To this end, the active ingredient in emulsifiable

and/or dispersible concentrate formulations is not in the solid phase as it is

in suspension concentrates, and thereby is not subject to settling or

physical phase separation of solid from liquid. Furthermore, the

development of appropriate solvents and other excipients typically requires

careful consideration so as to achieve a passable emulsifiable and/or

dispersible concentrate formulation.

In view of the foregoing, the invention advantageously provides a

highly loaded emulsifiable and/or dispersible concentrate alpha

cypermethrin composition or formulation suitable for the prevention,

control or treatment of a range of pest infestations in an agricultural or

horticultural setting.

As generally used herein, the term "highly loaded" is to be taken to

refer to the concentration level of alpha-cypermethrin pesticide in an emulsifiable and/or dispersible concentrate formulation on a weight by volume basis (g/L) in the amount from at least about 125 g/L.

In one aspect, the invention provides an emulsifiable and/or

dispersible concentrate formulation comprising:

alpha-cypermethrin at a concentration of at least about 125 g/L;

a surfactant; and

two or more solvents.

In a related aspect, the invention provides a method of preparing an

emulsifiable and/or dispersible concentrate alpha-cypermethrin formulation

including the steps of:

(a) combining alpha-cypermethrin, a surfactant and two or more

solvents, wherein alpha-cypermethrin is present at a concentration of at

least about 125 g/L; and

(b) mixing the mixture of step (a) to thereby prepare the emulsifiable

and/or dispersible concentrate alpha-cypermethrin formulation.

The statements which follow apply equally to the aforementioned

aspects of the invention.

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. By way of example, a water insoluble active ingredient is typically dissolved in a largely water insoluble solvent that upon combination with water or the like and agitation forms an emulsion being a distribution of droplets of the water insoluble solvent and active ingredient amongst a water matrix stabilised by surfactants. 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.

Similarly, it will be appreciated that the term "dispersible

concentrate formulation" or "dispersible concentrate" (DC) 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 a dispersion therein.

By way of example, a water insoluble active ingredient is typically

dissolved in a largely water-soluble solvent that upon combination with

water forms a single mixed liquid phase with the water insoluble active

ingredient coming out of solution and the resulting combination being a

dispersion as stabilised by surfactants. The term "dispersion", as used

herein, refers to a liquid medium containing a suspension of minute solids,

such as minute colloid particles.

In particular embodiments, the present formulation is or comprises

an emulsion concentrate. In alternative embodiments, the present

formulation is or comprises a dispersible concentrate. It will be

appreciated, however, that in further embodiments, the formulation type

can have characteristics or features that are intermediate an emulsifiable concentrate and a dispersion concentrate. This may be achieved, for example, by the two or more solvents including a water-soluble (miscible) solvent (e.g., NMP) and a water-insoluble (immiscible) solvent (e.g., solvent naphtha). Accordingly, in particular embodiments, the two or more solvents of the present formulation comprise a water soluble solvent and/or a water insoluble solvent.

The term "cypermethrin" refers to the synthetic pyrethroid (R,S)-a

cyano-3-phenoxybenzyl-(1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2

dimethylcyclopropanecarboxylate. It is generally appreciated that

cypermethrin can comprise eight isomers (i.e., four cis isomers and four

trans isomers), with the cis isomers typically being the more biologically

active. Depending upon the manufacturing source of cypermethrin, the

cis:trans isomer ratio can vary from 40:60 to 80:20. Since the discovery

and commercialization of cypermethrin, products containing increased or

enriched amounts of certain isomers have been developed.

It will be appreciated that use of the term "cypermethrin" herein can

refer to one or more of these eight isomers, including specific mixtures

and/or ratios thereof as are known in the art, such as the enriched

cypermethrins of alpha-cypermethrin, beta-cypermethrin, theta

cypermethrin and zeta-cypermethrin.

With respect to alpha-cypermethrin, it will be understood that alpha

cypermethrin contains more than 90% of the insecticidally most active

enantiomer pair of the four cis isomers of cypermethrin as a racemic mixture (i.e., (S)-a-cyano-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)

2,2-dimethylcyclopropanecarboxylate and (R)-a-cyano-3-phenoxybenzyl

(1S)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate).

Cypermethrin demonstrates markedly higher solubility than alpha

cypermethrin when dissolved in a number benchmark solvents. For

example, in ethyl acetate at 200 C, cypermethrin has been shown to be in

of the order of 4 times more soluble than alpha-cypermethrin (200 v

58.4g/L). Furthermore, in methanol at 200 C, it has been previously

demonstrated cypermethrin is of the order of 20 times more soluble than

alpha-cypermethrin (450 v 21.3g/L) (International Union of Pure and

Applied Chemistry (IUPAC). 2017. Cypermethrin (Ref: OMS 2002).

University of Hertfordshire; International Union of Pure and Applied

Chemistry (IUPAC). 2017. Alpha-cypermethrin (Ref: OMS 3004).

University of Hertfordshire). Additionally, in hexane at 200 C, cypermethrin

has been shown to be in the order of 15 times more soluble than alpha

cypermethrin (103 v 7g/L) (British Crop Protection Council (BCPC). 2002.

The e-Pesticide Manual. edn. 2.2. Wise and Loveys Information Services

Ltd). Accordingly, there are significant differences between cypermethrin

and alpha-cypermethrin in terms of their ability to be formulated as an

emulsifiable and/or dispersible concentrate.

For the present invention, alpha-cypermethrin, is suitably present in

a highly loaded concentration (i.e., at least about 125 g/L) that provides an

emulsifiable and/or dispersible concentrate formulation suitable for use in the effective prevention, control and/or treatment of a pest infestation. To this end, alpha-cypermethrin, may be present in an amount from about

125 g/L to about 500 g/L or any range therein such as, but not limited to,

about 150 g/L to about 450 g/L, or about 200 g/L to about 300 g/L of the

emulsifiable and/or dispersible concentrate formulation. In particular

embodiments of the present invention, alpha-cypermethrin is present in an

amount of about 125, 130, 135, 140, 145, 150, 155, 160, 165, 170, 175,

180, 185, 190, 195, 200, 205, 210, 215, 220, 225, 230, 235, 240, 245,

250, 255, 260, 265, 270, 275, 280, 285, 290, 295, 300, 305, 310, 315,

320, 325, 330, 335, 340, 345, 350, 355, 360, 365, 370, 375, 380, 385,

390, 395, 400, 405, 410, 415, 420, 425, 430, 435, 440, 445, 450, 455,

460, 465, 470, 475, 480, 485, 490, 495, 500 g/L, or any range therein, of

the emulsifiable and/or dispersible concentrate formulation. In certain

embodiments of the present invention, alpha-cypermethrin is present in an

amount of about 150 g/L to about 450 g/L, more preferably about 200 g/L

to about 400 g/L and even more preferably about 250 g/L to about 350 g/L

of the emulsifiable and/or dispersible concentrate formulation.

The term "solvent" refers to any liquid capable of maintaining

another substance in solution. Examples of solvents include, but are not

limited to, organic solvents. It will be apparent to the skilled artisan that the

two or more solvents may include any appropriate solvent as are known in

the art. By way of example, the two or more solvents 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).

In one preferred embodiment, at least one of the two or more

solvents is suitably selected from the group consisting of an aromatic

hydrocarbon, a lactam, an alkyl benzoate, a lactone and any combination

thereof. More preferably, at least one of the two or more solvents are

selected from the group consisting of a heavy aromatic solvent naphtha

(petroleum), a pyrrolidone, methyl benzoate, ethyl benzoate, caprolactone

and any combination thereof.

Such solvents may be used in combination as a mixture of two,

three, four, five or more solvents. In one particular embodiment, the two or

more solvents comprise first and second solvents. It will be appreciated

that the first and second solvents may be or comprise any solvent known

in the art. Preferably, the first solvent is selected from the group consisting

of a lactam, a lactone, and any combination thereof and/or the second

solvent is selected from the group consisting of an aromatic hydrocarbon, an alkyl benzoate and any combination thereof.

For the present aspect, the ratio of the first solvent to the second

solvent is suitably about 3:1, 2.9:1, 2.8:1, 2.7:1, 2.6:1, 2.5:1, 2.4:1, 2.3:1,

2.2:1, 2.1:1, 2:1, 1.9:1, 1.8:1, 1.7:1, 1.6:1, 1.5:1, 1.4:1, 1.3:1, 1.2:1, 1.1:1,

1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4:, 1:1.5, 1:1.6, 1:1.7, 1:1.8, 1:1.9, 1:2, 1:2.1,

1:2.2, 1:2.3, 1:2.4, 1:2.5, 1:2.6, 1:2.7, 1:2.8, 1:2.9, 1:3 and any range

therein. In one preferred embodiment, the ratio of the first solvent to the

second solvent is in the range of about 3:1 to about 1:3.

For the above aspects, the two or more solvents may be present in

an amount from about 500 g/L to about 800 g/L or any range therein such

as, but not limited to, about 600 g/L to about 700 g/L, or about 650 g/L to

about 750 g/L of the emulsifiable and/or dispersible concentrate

formulation. In particular embodiments of the present invention, the two or

more solvents are 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 g/L, or any

range therein, of the emulsifiable and/or dispersible concentrate

formulation. In certain embodiments of the present invention, the two or

more solvents are present in an amount of at least about 500 g/L of the

emulsifiable and/or dispersible concentrate formulation. More preferably,

the two or more solvents are present in an amount ranging between about

500 g/L to about 800 g/L of the emulsifiable and/or dispersible concentrate

formulation.

Further to the above, the solvents provided herein are preferably

two or more agriculturally acceptable solvents. 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.

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.

Accordingly, in particular embodiments, the surfactant is or

comprises an emulsifying agent. As generally used herein, the term

"emulsifying agent" or "emulsifier" refers to a chemical agent, compound,

or substance capable of producing an emulsion by reducing the interfacial

tension between the two insoluble liquids.

Similar to that for the solvents provided above, the surfactant

provided herein is preferably an agriculturally acceptable surfactant. The

term "agriculturally acceptable surfactant" as used herein refers to a

surfactant 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

surfactant when used as described herein.

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

and/or dispersible concentrate alpha-cypermethrin formulation. In this

regard, it will be apparent that an amount of the surfactant of the

emulsifiable and/or dispersible concentrate formulation can vary, for

example, depending on the particular alpha-cypermethrin concentration

and the particular surfactant to be included therein.

To this end, the surfactant may be present in an amount from about

20 g/L to about 300 g/L or any range therein such as, but not limited to,

about 30 g/L to about 200 g/L, or about 50 g/L to about 100 g/L of the

emulsifiable and/or dispersible concentrate formulation. In particular

embodiments of the present invention, the surfactant is present in an

amount of about 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90,

95, 100, 105, 110, 115, 120, 125, 130, 135, 140, 145, 150, 155, 160, 165,

170, 175, 180, 185, 190, 195, 200, 205, 210, 215, 220, 225, 230, 235,

240, 245, 250, 255, 260, 265, 270, 275, 280, 285, 290, 295, 300 g/L, or any range therein, of the emulsifiable and/or dispersible concentrate formulation. In certain embodiments of the present invention, the surfactant is present in an amount of at least about 40 g/L of the emulsifiable and/or dispersible concentrate formulation. More preferably, the surfactant is present in an amount ranging between about 50 g/L to about 150 g/L of the emulsifiable and/or dispersible concentrate formulation.

For the present invention, the surfactant is suitably selected from

the group consisting of non-ionic surfactants, anionic surfactants, cationic

surfactants, zwitterionic surfactants, cation-anion composite surfactants

and any combination thereof. Suitable non-ionic surfactants are may

include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers,

polyoxyethylene polyoxypropylene ethers, polyoxyethylene alkyl esters,

polyoxyethylene sorbitan alkyl esters, polyoxyethylene polyoxypropylene

block copolymers, sorbitan alkyl esters, higher fatty acid alkanolamides

and any combination thereof. Suitable cationic surfactants may include

alkylamine salts, quaternary ammonium salts and combinations thereof.

Further, suitable anionic surfactants may include naphthalenesulfonic acid

polycondensate, alkenylsulfonate, naphthalenesulfonate, formalin

condensate of a naphthalenesulfonate, formadehyde condensate of an

alkylnaphthalenesulfonate, lignin sulfonate, alkylarylsulfonate, alkylaryl

sulfonate sulfate, polystyrene sulfonate, polycarboxylate,

polyoxyethylenealkyl ether sulfate, polyoxyethylenealkylaryl ether sulfate, alkylsulfosuccinate, alkyl sulfate, alkyl ether sulfonate, a higher fatty acid alkali salt and any combination thereof.

In certain preferred embodiments, the one or more surfactants to be

included in the emulsifiable and/or dispersible concentrate formulation are

or comprise an anionic surfactant. As generally used herein, the term

"anionic surfactant" refers to a surfactant comprising, as ionic or ionizable

groups, only anionic groups. Such anionic groups may include, for

example, -CO2H, -C2-, -SO3H, -S03-, -OSO3H, -OS03-, -H2PO3, -HP03-,

-P03 2 -, -H2PO2, =HPO2, -HP02-, =P02-, =POH, and =PO- groups.

Suitable anionic surfactants may include those hereinbefore described.

Such anionic surfactants may be used alone or in combination as a

mixture of two, three, four, five or more anionic surfactants.

In particular embodiments, the surfactant is selected from the group

consisting of an alkoxylated oil (e.g., -54 x ethoxylated (e.g., T1285)), an

alkylphenol alkoxylate (e.g., -10 x ethoxylated (e.g., TericNl10)), an

alkoxylated alcohol (Alcohol C12 - C15, -23 x ethoxylated (e.g. Teric

12A23); Alcohol C12, -3 x ethoxylated (e.g. Surfactant 12A3)), an

alkoxylated polyaryl phenol (e.g., Tristyryl Phenol, -16 x ethoxylated (e.g.

TSP15)), an alkoxylated block co-polymer (Ethoxylate-Propoxylate

copolymer (e.g. Teric PE64)), an alkylbenzenesulphonate (e.g., Calcium

C10-16 alkylbenzyl sulphonate, branched or linear chain in solvent (e.g.

Ninate 60E, NANSA EVM70/2E, Kemmat HF60)), an alcohol ether

sulphate (e.g. Toximul TANS-5), an alkylamine ethoxylate (e.g. Toximul

TAABS-5) and any combination thereof. More preferably, the surfactant is

selected from the group consisting of an ethoxylated castor oil, an

ethoxylated nonylphenol, an ethoxylated alcohol, an ethoxylated

tristyrylphenol, an ethoxylate-propoxylate copolymer, a C10-16

alkylbenzenesulphonate (branched or linear in solvent), a branched

alcohol ether sulphate, a tallowamine alkoxylated salt and any

combination thereof.

Preferably, the castor oil alkoxylate has a degree of alkoxylation of

about 36 or greater. Preferably, the alkylphenol alkoxylate has a degree of

alkoxylation greater than 2, more preferably greater than 6 and even more

preferably greater than 8. Preferably, the alkoxylated alcohol has a degree

of alkoxylation greater than 2. Preferably, the alkoxylated polyaryl phenol

has a degree of alkoxylation greater than 8.

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 alpha

cypermethrin within the formulation of the invention.

Accordingly, in particular embodiments, at least two of the two or

more solvents are each present in an amount of at least about 30 g/L

(e.g., 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170,

180, 190, 200, 210, 220, 230, 240, 250 g/L and any range therein). More

preferably, at least two of the two or more solvents are each present in an

amount of at least about 100 g/L and even more preferably at least about

200 g/L.

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 and/or dispersible concentrate formulation as required.

It will be understood that it is desirable for the emulsifiable and/or

dispersible concentrate provided herein to be readily or easily pumped or

poured from a storage vessel. Preferably, the emulsifiable and/or

dispersible concentrate formulation has a viscosity at room temperature

(i.e., 20 0C) 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 and/or dispersible

concentrate formulation of the invention has a viscosity at room

temperature of about or less than 400 cPs.

With respect to the aforementioned aspect of preparing an

emulsifiable and/or dispersible concentrate formulation of alpha cypermethrin, 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 and/or

dispersible concentrate formulation prepared by the method of the

aforementioned aspect.

In a further aspect, the invention resides in a method of preventing

and/or controlling a pest infestation in a target area, including the step of

applying a pesticidally effective amount of the emulsifiable and/or

dispersible concentrate formulation of first or third mentioned aspects

mixed with water or a water-containing liquid to the target area to thereby

prevent and/or control the pest infestation.

Suitably, the method of this aspect further includes the initial step of

mixing the emulsifiable and/or dispersible concentrate alpha-cypermethrin

formulation with water or the water-containing liquid.

The terms "treat", "treat" and "treatment" are broadly intended to

include preventing or controlling a pest infestation. Treating the pest

infestation preferably results in at least maintaining, more preferably

maintaining or reducing, and even more preferably reducing the degree or

severity of the pest infestation in a target area. In one embodiment,

treatment with the emulsifiable and/or dispersible concentrate formulation

provided herein is able to substantially eradicate an existing pest

infestation.

As used herein, "preventing" (or "prevent" or "prevention") refers to

a course of action (such as administering an effective amount of the

emulsifiable and/or dispersible concentrate formulation described herein)

initiated prior to the onset of a symptom, aspect, or characteristic of the

pest infestation (e.g., plant or crop damage) so as to prevent, reduce or

delay the symptom, aspect, or characteristic thereof. It is to be understood

that such preventing need not be absolute to be beneficial to a plant, crop

or the like.

As generally used herein, "control" (or "controlled" or "controlling")

refers to an intervention with the emulsifiable and/or dispersible

concentrate formulation that reduces or ameliorates a symptom, aspect, or

characteristic of the pest infestation after it has begun to develop. The

term "ameliorating", with reference to a pest infestation, refers to any

observable beneficial effect thereto as a result of the administration of the

emulsifiable and/or dispersible concentrate formulation. The beneficial

effect can be determined using any methods or standards known to the

ordinarily skilled artisan. Accordingly, these terms are meant to include

any lethal (i.e., pesticidal) or inhibitory (i.e., pestistatic) activities of the

emulsifiable and/or dispersible concentrate formulation against a given

pest, including those hereinafter described.

Herein, the terms "target area", "locus" or "space" refer to any area,

location or habitat where the prevention, control and/or eradication of a

pest infestation is needed or expected to be needed.

As used herein, the terms "effective amount" or "pesticidally

effective amount" refer to an amount of the emulsifiable and/or dispersible

concentrate formulation that is effective to cause such prevention, control,

and/or eradication of the pest infestation. By way of example, an effective

amount means an amount necessary to produce an observable pesticidal

and/or pestistatic effect on unwanted pests (e.g., insects), including the

effects of death, growth inhibition, reproduction inhibition, inhibition of

proliferation, and removal, destruction, or otherwise diminishing the

occurrence and activity of these unwanted pests. An effective amount of

the emulsifiable and/or dispersible concentrate formulation of the invention

may vary according to the prevailing conditions such as desired pesticidal

and/or pestistatic effect and duration, weather, target species, habitat,

mode of application, and the like.

In particular embodiments, an effective amount is the amount of the

emulsifiable and/or dispersible concentrate formulation of the invention

that has an adverse effect (e.g., reproduction inhibition, knockdown and/or

death) on at least 25% (e.g., 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%,

65%, 70%, 75%, 80%, 85%, 90%, 95%, 100% or any range therein) of the

pests treated or contacted therewith, more preferably at least 50% of the

pests treated or contacted therewith, and even more preferably at least

70% or greater of the pests treated or contacted therewith.

The efficacy of the emulsifiable and/or dispersible concentrate

formulation of the present invention may be monitored by determining the mortality of or adverse effect upon treated pests (e.g., insects). This includes inhibition or modulation of pest growth, inhibition of pest reproduction by slowing or arresting its proliferation, or complete destruction/death of the pest. The actual value of an effective amount for the emulsifiable and/or dispersible concentrate formulation is preferably determined by routine screening procedures employed to evaluate pesticidal activity and efficacy, such as those methods well known in the art.

With respect to the above, an effective amount of the emulsifiable

and/or dispersible concentrate formulation described herein is preferably

administered to the target area or locus of the pest infestation. By way of

example, to prevent or control pest-related damage to a plant or crop, an

effective amount of an emulsifiable and/or dispersible concentrate

formulation comprising alpha-cypermethrin is administered to an area

adjacent and/or including the plant or crop. As such, a pest, and in

particular insects, can be readily contacted with an effective amount of the

emulsifiable and/or dispersible concentrate formulation of the invention.

The pest infestation to be prevented and/or controlled by the

method of the present aspect may be in respect of any pest, and more

particularly any insect or insects, as are well known in the art. Nonlimiting

examples of pests, and in particular insects, that may be treated by

application of the emulsifiable and/or dispersible concentrate formulation

of the invention include grasshoppers, locusts, earwigs, crickets, millipedes, slaters, ants, aphids, flies, mites, beetles, bugs, moths, springtails, caterpillars, loopers, bruchids, fleas, mealybugs, midges, thrips, weevils, butterflies and cockroaches, which can cause significant damage to, for example, a wide range of agricultural and horticultural crops and plants.

The emulsifiable and/or dispersible concentrate formulation of the

invention may be applied to the target crop or plant of interest, to a part

thereof (such as the leaf or seed), or to surroundings thereof. Methods and

techniques for applying the emulsifiable and/or dispersible concentrate

formulation are known in the art and may include, for example, ground or

aerial spraying.

In a preferred embodiment, the emulsifiable and/or dispersible

concentrate formulation is applied at a rate of about 5 to 500mL per

hectare (e.g., about 5mL, 10mL, 15mL, 20mL, 25mL, 30mL, 35mL, 40mL,

45mL, 50mL, 55mL, 60mL, 65mL, 70mL, 75mL, 80mL, 85mL, 90mL,

95mL, 100mL, 105mL, 110mL, 115mL, 120mL, 125mL, 130mL, 135mL,

140mL, 145mL, 150mL, 155mL, 160mL, 165mL, 170mL, 175mL, 180mL,

185mL, 190mL, 195mL, 200mL, 205mL, 210mL, 215mL, 220mL, 225mL,

230mL, 235mL, 240mL, 245mL, 250mL, 255mL, 260mL, 265mL, 270mL,

275mL, 280mL, 285mL, 290mL, 295mL, 300mL, 305mL, 310mL, 315mL,

320mL, 325mL, 330mL, 335mL, 340mL, 345mL, 350mL, 355mL, 360mL,

365mL, 370mL, 375mL, 380mL, 385mL, 390mL, 395mL, 400mL, 405mL,

410mL, 415mL, 420mL, 425mL, 430mL, 435mL, 440mL, 445mL, 450mL,

455mL, 460mL, 465mL, 470mL, 475mL, 480mL, 485mL, 490mL, 495mL,

500mL per hectare and any range therein) and more preferably at a rate of

about 15mL to about 300mL per hectare subsequent to dilution thereof in

a suitable spray liquid. Obviously, the amount of the emulsifiable and/or

dispersible concentrate to be applied per hectare will depend, at least in

part, upon the concentration of alpha-cypermethrin therein, the particular

pest infestation to be targeted and the type of target crop to which the

formulation is to be applied.

Throughout the specification the aim has been to describe the

preferred embodiments of the invention without limiting the invention to

any one embodiment or specific collection of features. It will therefore be

appreciated by those of skill in the art that, in light of the instant disclosure,

various modifications and changes can be made in the particular

embodiments exemplified without departing from the scope of the present

invention.

All computer programs, algorithms, patent and scientific literature

referred to herein is incorporated herein by reference.

Any reference to publications cited in this specification is not an

admission that the disclosures constitute common general knowledge in

Australia.

In order that the invention may be more readily understood and put

into practice, one or more preferred embodiments thereof will now be

described, by way of example only.

Example 1: Embodiments of a Highly Loaded Alpha-Cypermethrin

Emulsifiable Concentrate Formulation

There are currently a number of existing 100g/L alpha-cypermethrin

emulsifiable concentrate products that are commercially available in

Australia, such as Imtrade's Dictate Duo 100 Insecticide, Relyon's

Alphanex 100Ec Insecticide (APVMA Product No. 81781), NovaGuard's

Alpha-Cypermethrin Duo 100 Insecticide (APVMA Product No. 80899),

Chieftain Duo 100EC Insecticide (APVMA Product No. 69532), Mascot

Duo Insecticide (APVMA Product No. 67541) and Farmalinx's AlphaCyper

Insecticide (APVMA Product No. 64298). A typical 100g/L emulsifiable

concentrate of alpha-cypermethrin combines ingredients as provided in

Tables 1 and 2 below.

Table 1: Standard formulation of an emulsifiable concentrate of 100

g/L alpha-cypermethrin

Ingredient Role Concentration

Alpha-cypermethrin (CAS# Active insecticidal 103g/L (to yield

67375-30-8) technical ingredient 100g/L on 100%

material, typically 97% basis)

Surfactants (various) Emulsification -5 to 15% w/w

(predominantly);

Other surfactant

properties such as

wetting, spreading,

sticking

Ancillaries(various) Various: dyes, variable

odourants, synergists,

deterrents, emetics, etc.

Solvent (various) Solvent Balance to 100%

w/w

Table 2: An embodiment of a formulation of an emulsifiable

concentrate of 100 g/L alpha-cypermethrin

Ingredient Role Concentration

Alpha-cypermethrin (CAS# Active insecticidal 103g/L (to yield

67375-30-8) technical ingredient 100g/L on 100%

material, 97% basis)

Vegetable oil alkoxylate Emulsifying agent 28g/L

(CAS# 61791-12-6)

Alkylbenzenesulfonic acid, Emulsifying agent 32g/L

calcium salt in 2-ethylhexanol

(CAS# 26264-06-2 / 104-76

7)

Solvent naphtha (petroleum), Solvent -755g/L

heavy aromatic (CAS# (Balance to

64742-94-5) 100% w/w)

To achieve a pesticide formulation with markedly higher

concentration of alpha-cypermethrin than the usual 100g/L therein, and to

retain a liquid form, one may pursue a suspension concentrate

formulation. This effectively presents the active ingredient as finely divided

particles physically suspended in a viscous carrier (water + thickener) with

included surfactants assisting in maintaining the product as a uniform

formulation. Nevertheless, suspension concentrates are not

thermodynamically stable and typically inevitably suffer from some settling

of active ingredient and in severe cases resolve into fully settled layers of

active ingredient and other solid components beneath an overlying layer of

the liquid carrier and other solubilised components, making this type of

formulation practically useless.

In the present example, alternatives to suspension concentrates

and single solvent emulsifiable concentrates were tested in terms of

emulsion and cold temperature stability (i.e., CIPAC MT39.3 testing

protocol). In particular, the present Example provides embodiments of

emulsifiable concentrates in which the solubility of the alpha-cypermethrin

active ingredient is increased by using two or more solvents. Without being

bound by any theory, it is believed that the solubility of the alpha

cypermethrin active ingredient is increased by providing a liquid matrix that

is more amenable to dissolving the solid active ingredient in terms of the

packing of particles through molecule sizing and the enduring prevailing forces of attraction and repulsion specific to the combination of solvents used.

In choosing solvent options, there are many considerations,

including but not limited to the candidates nature/classification with respect

to:

- Chemical and physical character - compatibility, stability, solubility

of target active, molecule size, viscosity

- Economics - price and availability

- Environment - acidity/alkalinity, persistence, degradation character,

partitioning coefficients

- Safety - toxicity, flammability, corrosiveness

- Regulation - status amongst classifications of hazardous

substances and/or dangerous goods

Such considerations are complex in themselves, though the level

of complexity increases quite significantly when two or more solvents are

considered in combination, given that both solvent selection and the

relative proportion of the solvent combination must be considered. Further

intricacy is added in that one or more surfactants must also be added to

impart the ability on the emulsifiable concentrate formulation to adequately

disperse the solvent containing dissolved active ingredient when added

into a diluent, such as water.

SINGLE SOLVENT EMBODIMENTS

In the present Example, the active ingredient content was initially

increased by displacing the solvent naphtha (petroleum), heavy aromatic

(e.g., Recosol 150) (and adjusting surfactants and other components to

suit) so as to achieve a higher concentration variant of the benchmark

product. This was attempted for emulsifiable concentrate formulations

having 150 g/L, 200 g/L and 300 g/L alpha-cypermethrin in each case

delivering an acceptable emulsion character. Unfortunately, as shown in

Table 3, at the same time in each case it failed to achieve a marked

increase in active ingredient concentration in a stable manner.

It will be appreciated that the solvent of choice for most large

volume, well-established, generic-type presentations of the alpha

cypermethrin active ingredient, including those listed above, is solvent

naphtha (petroleum), heavy aromatic. This is particularly owing to this

solvent's wide availability, low relative cost and broadly favourable

solubilisation of many non-water soluble pesticide agents. As alluded to

earlier, however, simple displacement of some of this solvent with

substantially more active ingredient is not a viable option to increase the

loading of alpha-cypermethrin in the emulsifiable concentrate formulations,

as this results in a final product that is not heterogeneous. That is, the

additional active ingredient is not stably solubilised, such that when

subject to standard cold temperature stability testing the alpha

cypermethrin active ingredient will crystallise out of solution, which is

unacceptable for commercially passable formulations.

Given the above, the present Example then focussed on

uncovering a suitable alternative single solvent capable of producing an

emulsifiable concentrate having a relatively high concentration of alpha

cypermethrin therein, the solvent having a flash-point beyond the

flammable liquid classification (dangerous goods qualification as a class 3

flammable liquid requires the flash point of the subject liquid to be 600 C

for closed cup testing or 65.60 C for open cup testing). This was first

tested by the way of NMP (N-methyl-2-pyrrolidone). However while this

embodiment delivered a stable heterogeneous formulation comprising the

alpha-cypermethrin active ingredient and included surfactants, NMP's high

water solubility prohibited the formation of an enduring, high quality

emulsion upon product dilution in water (Table 3). To this end, NMP is

highly water soluble and upon combination with water the active ingredient

seemingly fell out of emulsion as the solvent dissolved in water rather than

establishing a stable emulsion of insoluble active ingredient-containing

liquid particles dispersed in water as facilitated by the surfactant

components.

As shown in Table 3, additional single solvents were tested and

found to not be suitable or passable in this respect. Using xylenes (mixed

isomers CAS# 1330-20-7) as a single solvent option, both 300g/L and

400g/L emulsifiable concentrate embodiments were tested, but both

displayed insufficient cold temp stability, yielding crystals of active

ingredient upon cold temperature storage of 7 days at 2C. Using cyclohexanones (CAS# 108-94-1) as a single solvent option, 400g/L,

500g/L and 600g/L emulsifiable concentrate variations were constructed.

A stable heterogeneous formulation was not achieved for any of these

attempts with cold temperature stability the deficiency. In any event,

cyclohexanone is undesirably flammable (with a flash point of 600 C for

closed cup testing or 65.60 C for open cup testing).

Emulsifiable concentrate formulations based individually on

isophorone (CAS# 78-59-1), methyl benzoate (CAS# 93-58-3) and

acetophenone (CAS# 98-86-2) were also evaluated. All of these

formulations failed to achieve adequate cold temperature stability with

crystallisation of alph-cypermethrin content (see Table 3).

Table 3 - Embodiments of higher-loading emulsifiable or dispersible

concentrate formulations using a single solvent system

Trial Sample Solvent Loading Emulsion CTS Remarks

number

Single Solvent

1.1 IAS16213 Solvent naphtha 150g/L Pass Fail Fail

1.2 IAS16212 (petroleum), heavy 200g/L Pass Fail Fail

aromatic (Recosol 300 g/L Pass Fail Fail 1.3 IAS16211 150)

2.1 IAS16228 150g/L Failed Pass Fail N-methyl 2.2 IAS16229 200 g/L Failed Pass Fail Pyrrolidone 2.3 IAS16219 300 g/L Failed Pass Fail

3.1 IAS17009 300 g/L Pass Fail Fail Xylene 3.2 IAS17010 400 g/L n/a Fail Fail

4.1 IAS17014 300 g/L Pass Fail Fail Isophorone 4.2 IAS17015 400 g/L Failed Fail Fail

5.1 IAS17029 400 g/L Pass Fail Fail

5.2 IAS17028 Cyclohexanone 500 g/L n/a n/a Fail

5.3 IAS17016 600 g/L n/a n/a Fail

6.1 IAS17030 Methyl 300 g/L Pass Fail Fail

6.2 IAS17031 Benzoate 400 g/L n/a n/a Fail

7.1 IAS17044 300 g/L Pass Fail Fail Acetophenone 7.2 IAS17043 400 g/L Pass Fail Fail

DUAL SOLVENT EMBODIMENTS

Given the above results in respect of single solvent embodiments,

embodiments including two solvents were then tested in terms of emulsion

and cold temperature stability. The results of this testing is outlined in

Table 4 below, which demonstrates that the dual solvent systems tested

were effective in producing passable highly loaded alpha-cypermethrin

emulsifiable concentrate formulations.

Table 4 - Embodiments of higher-loading emulsifiable and/or

dispersible concentrate formulations using a dual solvent system

Trial Sample Solvent Loading Emulsion CTS Remarks

number

Recosol 150 +

A IAS16075 300g/L Pass Pass Pass NMP

8.1 1AS16164 Methyl 300 g/L Pass Pass Pass

Benzoate/

NMP

Ethyl 300 g/L Pass Pass Pass

Benzoate/NMP

12.1 1AS17132 R150/ Octyl 300 g/L Pass Pass Pass

pyrrolidone

12.2 1AS17133 R150/ 300 g/L Pass Pass Pass

Caprolactone

In one embodiment, it was found that by combining solvent naphtha

(petroleum), heavy aromatic and N-methyl-pyrrolidone together, the best

of both worlds is achieved - i.e. concurrently acceptable cold temperature

stability and emulsion quality. A preferred embodiment of such a

formulation that attains a 300g/L alpha-cypermethrin emulsifiable

concentrate is provided in Table 5 below.

Table 5 - Formulation of Recosol 150 + NMP embodiment

Ingredient Role Concentration

Alpha-cypermethrin (CAS# Active insecticidal 316g/L (to yield

67375-30-8) technical ingredient 300g/L on 100%

material, 97% basis)

Vegetable oil alkoxylate Surfactant 33g/L

(CAS# 61791-12-6)

Alkylbenzenesulfonic acid, Surfactant 33g/L

calcium salt in 2-ethylhexanol

(CAS# 26264-06-2 / 104-76

7)

N-methyl pyrrolidone (CAS# Solvent -425g/L

872-50-4)

Solvent naphtha (petroleum), Solvent -244g/L

heavy aromatic (CAS# (Balance to

64742-94-5) 100% w/w)

The combination of alpha-cypermethrin with solvent naphtha

(petroleum), heavy aromatic and N-methyl-pyrrolidone as an emulsifiable

and/or dispersible concentrate was further exemplified with a range of

alternative surfactants, as shown in Tables 6 and 7 below. This reinforces

that the success of these dual solvent formulations resides largely with the

solvent combinations rather than the included surfactant(s).

Table 6 - Variation of surfactant trials at 300g/L

Sample Solvent Surfactant Emulsion/ CTS Remarks

number used Dispersion

Variation of non-ionics with anionic surfactant set as N60E

IAS17053 Teric N10 Pass Pass Pass

IAS17054 Recosol Teric 12A3 Pass Pass Pass

150/ N- Surfactant Pass Pass IAS17055 Pass methyl 12A3

IAS17056 Pyrrolidone TSP16 Pass Pass Pass

IAS17057 Teric PE64 Pass Pass Pass

Variation of Anionics with non-ionic surfactant set as T1285

Nansa EVM Pass Pass IAS17058 Pass Recosol 70/B

150/ N- Kemmat Pass Pass IAS17060 Pass methyl HF60

IAS17061 Pyrrolidone TANS 5 Pass Pass Pass

IAS17062 TAABS 5 Pass Pass Pass

Solvent used is R150/NMP, surfactant loading at 50:50 ratio

Table 7 - Formulations of surfactant trials

Trial Trial Trial Trial Trial Trial Trial Trial Trial

9.1 9.2 9.3 9.4 9.5 9.6 9.7 9.8 9.9

Component

Loading, g/L 300 300 300 300 300 300 300 300 300

Alpha cypermethrin tech 316 316 316 316 316 316 316 316 316

Solvent naphtha 244 244 244 244 244 244 244 244 244

(petroleum), heavy

aromatic (eg. Recosol

150)

N-Methyl Pyrrolidone 425 425 425 425 425 425 425 425 425

Castor oil ethoxylate (eg. - - - - - 33 33 33 33

T1285)

Nonyl phenol ethoxylate 33 - - - - - - -

(eg. TericN10)

Ethoxylated alcohol C12 - 33 - - - - - -

- C15 (E023)

(eg. Teric 12A23)

Polyoxyethylene Lauryl - - 33 - - - - -

Ether

(eg. Surfactant 12A3)

Tristyryl Phenol - - - 33 - - - -

ethoxylate (eg. TSP16)

Block co-polymer (eg. - - - - 33 - - -

Teric PE64)

Calcium dodecyl benzyl 33 33 33 33 33 - - -

sulphonate in 2-EH

(eg. Ninate 60E)

Calcium dodecyl benzyl - - - - - 33

sulphonate in butanol

branched (eg.

NANSAEVM 70/B)

Calcium dodecyl benzyl - - - - - - 33

sulphonate in - linear

(eg. Kemmat HF60)

Alkyl phenol ether - - - - - - - 33

sulphate/ tallowamine

ethoxylated salt (eg.

TANS 5)

Branched alcohol ether - - - - - - - - 33

sulphate/ tallow amine

ethoxylated salt (eg.

TAABS5)

A number of higher-loading alpha-cypermethrin emulsifiable and/or

dispersible concentrate formulations using one or more alternative

solvents to the previously described solvent naphtha (petroleum), heavy

aromatic and N-methyl-pyrrolidone pairing were also developed as

provided in Tables 8 to 11 below.

Table 8 - Formulation of methyl benzoate + NMP embodiment

Ingredient Role Concentration

Alpha-cypermethrin (CAS# Active insecticidal 316g/L (to yield

67375-30-8) technical ingredient 300g/L on 100%

material, 97% basis)

Vegetable oil alkoxylate Surfactant 33g/L

(CAS# 61791-12-6)

Alkylbenzenesulfonic acid, Surfactant 33g/L

calcium salt in 2-ethylhexanol

(CAS# 26264-06-2 / 104-76

7)

N-methyl pyrrolidone (CAS# Solvent -425g/L

872-50-4)

Methyl benzoate (CAS# 93- Solvent -330g/L

58-3) (Balance to

100% w/w)

Table 9 - Formulation of Recosol 150 + octyl-pyrrolidone

embodiment

Ingredient Role Concentration

Alpha-cypermethrin (CAS# Active insecticidal 316g/L (to yield

67375-30-8) technical ingredient 300g/L on 100%

material, 97% basis)

Vegetable oil alkoxylate Surfactant 33g/L

(CAS# 61791-12-6)

Alkylbenzenesulfonic acid, Surfactant 33g/L

calcium salt in 2-ethylhexanol

(CAS# 26264-06-2 / 104-76

7)

N-octyl-pyrrolidone (CAS# Solvent -293g/L

2687-94-7)

Solvent naphtha (petroleum), Solvent -324g/L

heavy aromatic (CAS# (Balance to

64742-94-5) 100% w/w)

Table 10 - Formulation of Recosol 150 + caprolactone embodiment

Ingredient Role Concentration

Alpha-cypermethrin (CAS# Active insecticidal 316g/L (to yield

67375-30-8) technical ingredient 300g/L on 100%

material, 97% basis)

Vegetable oil alkoxylate Surfactant 33g/L

(CAS# 61791-12-6)

Alkylbenzenesulfonic acid, Surfactant 33g/L

calcium salt in 2-ethylhexanol

(CAS# 26264-06-2 / 104-76

7)

Caprolactone (CAS# 502-44- Solvent -327g/L

3)

Solvent naphtha (petroleum), Solvent -338g/L

heavy aromatic (CAS# (Balance to

64742-94-5) 100% w/w)

Table 11 - Formulation of N-methyl pyrrolidone + ethyl benzoate

embodiment

Ingredient Role Concentration

Alpha-cypermethrin (CAS# Active insecticidal 316g/L (to yield

67375-30-8) technical ingredient 300g/L on 100%

material, 97% basis)

Vegetable oil alkoxylate Surfactant 35g/L

(CAS# 61791-12-6)

Alkylbenzenesulfonic acid, Surfactant 33g/L

calcium salt in 2-ethylhexanol

(CAS# 26264-06-2 / 104-76

7)

N-methyl pyrrolidone (CAS# Solvent -504g/L

872-50-4)

Ethyl benzoate (CAS# 93-89- Solvent -216g/L

) (Balance to

100% w/w)

A further stable embodiment of higher-loading emulsifiable and/or

dispersible concentrate formulation using a different solvent naphtha

(petroleum), heavy aromatic to N-methyl-pyrrolidone ratio to that provided

in Table 5 is provided in Table 12 below.

Table 12 - Formulation of Recosol 150 + NMP embodiment with

varied solvent proportions

Ingredient Role Concentration

Alpha-cypermethrin (CAS# Active insecticidal 316g/L (to yield

67375-30-8) technical ingredient 300g/L on 100%

material, 97% basis)

Vegetable oil alkoxylate Surfactant 33g/L

(CAS# 61791-12-6)

Alkylbenzenesulfonic acid, Surfactant 33g/L

calcium salt in 2-ethylhexanol

(CAS# 26264-06-2 / 104-76

7)

N-methyl pyrrolidone (CAS# Solvent -325g/L

872-50-4)

Solvent naphtha (petroleum), Solvent -332g/L

heavy aromatic (CAS# (Balance to

64742-94-5) 100% w/w)

Further embodiments having higher loadings than the previously

exemplified 300g/L alpha-cypermethrin content were developed as

outlined in Tables 13 to 15 below. Each embodiment was determined as

having adequate emulsion quality and cold temperature stability.

Table 13: 350 g/L alpha-cypermethrin EC formulation

Ingredient Role Concentration

Alpha-cypermethrin (CAS# Active insecticidal 368g/L (to yield

67375-30-8) technical ingredient 350g/L on 100%

material, 97% basis)

Vegetable oil alkoxylate Surfactant 34g/L

(CAS# 61791-12-6)

Alkylbenzenesulfonic acid, Surfactant 34g/L

calcium salt in 2-ethylhexanol

(CAS# 26264-06-2 / 104-76

7)

N-methyl pyrrolidone (CAS# Solvent -398g/L

872-50-4)

Solvent naphtha (petroleum), Solvent -229g/L

heavy aromatic (CAS# (Balance to

64742-94-5) 100% w/w)

Table 14: 400 g/L alpha-cypermethrin EC and/or DC formulation

Ingredient Role Concentration

Alpha-cypermethrin (CAS# Active insecticidal 421g/L (to yield

67375-30-8) technical ingredient 400g/L on 100%

material, 97% basis)

Vegetable oil alkoxylate Surfactant 34g/L

(CAS# 61791-12-6)

Alkylbenzenesulfonic acid, Surfactant 34g/L

calcium salt in 2-ethylhexanol

(CAS# 26264-06-2 / 104-76

7)

N-methyl pyrrolidone (CAS# Solvent -373g/L

872-50-4)

Solvent naphtha (petroleum), Solvent -215g/L

heavy aromatic (CAS# (Balance to

64742-94-5) 100% w/w)

Table 15: 450 g/L alpha-cypermethrin EC and/or DC formulation

Ingredient Role Concentration

Alpha-cypermethrin (CAS# Active insecticidal 474g/L (to yield

67375-30-8) technical ingredient 450g/L on 100%

material, 97% basis)

Vegetable oil alkoxylate Surfactant 34g/L

(CAS# 61791-12-6)

Alkylbenzenesulfonic acid, Surfactant 34g/L

calcium salt in 2-ethylhexanol

(CAS# 26264-06-2 / 104-76

7)

N-methyl pyrrolidone (CAS# Solvent -348g/L

872-50-4)

Solvent naphtha (petroleum), Solvent -200g/L

heavy aromatic (CAS# (Balance to

64742-94-5) 100% w/w)

Claims (18)

1. An emulsifiable and/or dispersible concentrate formulation comprising:

alpha-cypermethrin at a concentration of at least about 125 g/L;

a surfactant; and

two or more solvents selected from the group consisting of: a heavy aromatic

solvent naphtha (petroleum), a pyrrolidone, methyl benzoate, ethyl benzoate,

caprolactone and any combination thereof.

2. The emulsifiable and/or dispersible concentrate formulation of Claim 1, wherein

alpha-cypermethrin is present at a concentration of at least about 200 g/L of the total

weight of the formulation.

3. The emulsifiable and/or dispersible concentrate formulation of any one of the

preceding claims, wherein the two or more solvents are present in an amount of at

least about 500 g/L.

4. The emulsifiable and/or dispersible concentrate formulation of Claim 3, wherein

the two or more solvents are present in an amount ranging between about 500 g/L to

about 800 g/L.

5. The emulsifiable and/or dispersible concentrate formulation of any one of the

preceding claims, comprising first and second solvents.

6. The emulsifiable and/or dispersible concentrate formulation of Claim 5, wherein the ratio of the first solvent to the second solvent is in the range of about 3:1 to about

1:3.

7. The emulsifiable and/or dispersible concentrate formulation of Claim 5 or Claim

8, wherein the first solvent is selected from the group consisting of a lactam, a lactone,

and any combination thereof

8. The emulsifiable and/or dispersible concentrate formulation of any one of

Claims 5 to 7, wherein the second solvent is selected from the group consisting of an

aromatic hydrocarbon, an alkyl benzoate and any combination thereof.

9. The emulsifiable and/or dispersible concentrate formulation of any one of the

preceding claims, wherein the surfactant is present in an amount of at least about 40

g/L.

10. The emulsifiable and/or dispersible concentrate formulation of Claim 9, wherein

the surfactant is present in an amount ranging between about 50 g/L to about 150 g/L.

11. The emulsifiable and/or dispersible concentrate formulation of any one of the

preceding claims, wherein the surfactant is selected from the group consisting of an

alkoxylated oil, an alkylphenol alkoxylate, an alkoxylated alcohol, an alkoxylated

polyaryl phenol, an alkoxylated block co-polymer, an alkylbenzenesulphonate, an

alcohol ether sulphate, an alkylamine ethoxylate and any combination thereof.

12. The emulsifiable and/or dispersible concentrate formulation of Claim 11, wherein the surfactant is selected from the group consisting of an ethoxylated castor oil, an ethoxylated nonylphenol, an ethoxylated alcohol, an ethoxylated tristyrylphenol, an ethoxylate-propoxylate copolymer, a C10-16 alkylbenzenesulphonate, a branched alcohol ether sulphate, a tallowamine alkoxylated salt and any combination thereof.

13. The emulsifiable and/or dispersible concentrate formulation of any one of the

preceding claims, wherein the surfactant comprises a non-ionic surfactant and/or an

anionic surfactant.

14. A method of preparing an emulsifiable and/or dispersible concentrate alpha

cypermethrin formulation including the steps of:

(a) combining alpha-cypermethrin, a surfactant and two or more solvents

selected from the group consisting of: a heavy aromatic solvent naphtha (petroleum),

a pyrrolidone, methyl benzoate, ethyl benzoate, caprolactone and any combination

thereof, wherein alpha-cypermethrin is present at a concentration of at least about 125

g/L; and

(b) mixing the mixture of step (a) to thereby prepare the emulsifiable and/or

dispersible concentrate alpha-cypermethrin formulation.

15. The method of Claim 14, wherein the emulsifiable and/or dispersible

concentrate alpha-cypermethrin formulation is that of any one of Claims 1 to 16.

16. An emulsifiable and/or dispersible concentrate alpha-cypermethrin formulation

prepared by the method of Claim 14 or Claim 15.

17. A method of preventing and/or controlling a pest infestation in a target area,

including the step of applying a pesticidally effective amount of the emulsifiable and/or

dispersible concentrate formulation of any one of Claims 1 to 13 and 16 mixed with

water or a water-containing liquid to the target area to thereby prevent and/or control

the pest infestation.

18. The method of Claim 17, further including the initial step of mixing the

emulsifiable and/or dispersible concentrate formulation with water or the water

containing liquid.