AU2020200088B2 - Gibberellic acid composition for enhancing plant growth - Google Patents

Abstract

A water-miscible composition for enhancing plant growth comprising gibberellic acid and one or more glycols, wherein the gibberellic acid is present in the composition at a concentration of at least 2% w/v of the total composition.

Description

1/1 1/1 06 Jan 2020 06 Jan 2020

Figure 11 Figure 2020200088

2020200088

BERATA GALA GALA VICTORIAN CONTENTS: 1L

1

2020200088 06 Jan 2020

Gibberellic acid Gibberellic acid composition compositionforfor enhancing enhancing plant plant growth growth

Field of Field of the the invention invention

[0001] The The

[0001] invention invention relates relates to to a composition a composition for for enhancing enhancing plant plant growth. growth. In particular, In particular, thethe

present invention present invention relates relates to to a water-miscible a water-miscible composition composition of gibberellic of gibberellic acid. acid.

Backgroundofofthe Background the invention invention

[0002] In this

[0002] In this specification,unless specification, unlessthe thecontrary contraryisis expressly expressly stated, stated, where where a a document, act or document, act or itemofofknowledge item knowledge is referred is referred to ortodiscussed, or discussed, this reference this reference or discussion or discussion is not anisadmission not an admission that the that the document, act or item document, act item of of knowledge orany knowledge or anycombination combinationthereof thereofwas was at at thepriority the priority date, date, publicly available, available, known to the known to the public, public, part partof ofcommon generalknowledge; common general knowledge;or or known known to be to be

relevant toananattempt relevant to attemptto to solve solve any any problem problem withthis with which which this specification specification is concerned. is concerned.

[0003]In theInfield

[0003] the field of agriculture, of agriculture, it is it is desirable desirable to rapidly to rapidly and efficiently and efficiently growPlant grow plants. plants. Plant growthregulators growth regulators (PGRs) (PGRs)and/or and/orchemical chemical fertilisers may fertilisers maybebeused usedtotoenhance enhanceplant plantgrowth. growth. PGRs,sometimes PGRs, sometimes referred referred totoasasplant planthormones, hormones,arearetypically typicallydefined definedasaseither either organic organic (naturallyderived) (naturally derived)oror synthetic synthetic compounds, compounds, other other than than nutrients, nutrients, that may that may be be applied applied directly to directly to a plant a plant and/or and/orits itssoil soil ininsmall smallamounts amounts to modify to modify the physiological the physiological processstructure process and/or and/or of structure of the the plant plant in insome some beneficial beneficial manner, such as manner, such as enhancing plant growth. enhancing plant growth.

[0004] There

[0004] There are are different different classes classes of of PGRs PGRs based based on their on their chemical chemical structure, structure, which which include: include:

abscisic acid, abscisic acid,auxin, auxin,cytokinin, cytokinin, ethylene ethylene and gibberellins. and gibberellins. Gibberellins Gibberellins areofa class are a class of diterpenoid diterpenoid

acids and acids include aa large and include large range range of of chemicals chemicals which are typically which are typically produced naturally, and produced naturally, and

obtained, from obtained, from aa variety of of organisms such as organisms such as plants plants and/or fungi. fungi. Gibberellic acid, acid, sometimes sometimes

referred to asasGA, referred to GAis3 , aistype a type of gibberellin of gibberellin whichwhich is frequently is frequently producedproduced andtheused for the and used for

agricultural purpose agricultural purpose of of enhancing plant growth. enhancing plant growth.

[0005] Gibberellic

[0005] Gibberellic acid acid stimulates stimulates seed seed germination, germination, triggers triggers transitionsfrom transitions frommeristem meristem to to shoot growth shoot growth(increasing (increasing inter-node inter-node extension, extension, leaf-growth leaf-growth and andapical apical dominance), dominance),vegetative vegetativetoto flowering, and flowering, and determines determinessex sexexpression expressionand andgrain graindevelopment. development.It It hashas long long been been obtained obtained forfor

these properties these properties by by chemical synthesis (for chemical synthesis (for example, by extraction example, by extraction from plants or microbial from plants microbial

fermentation)andand fermentation) used used in agricultural in the the agricultural industry industry for enhancing for enhancing plant plant growth. growth.

[0006]Generally,

[0006] Generally, gibberellic gibberellic acid is acid is available available as aorliquid as a liquid or solid formulation. solid formulation. It can It can then be then be appliedtotoplants applied plantsinina avariety variety of of ways, ways, which which include include spraying spraying a liquidaform liquid form of gibberellic of gibberellic acid acid

ME_166604682_2 onto the theplants, plants,growing growing plants in ain a media containing gibberellic acid, or acid, or plants dipping plants 2020200088 06 Jan 2020 onto plants media containing gibberellic dipping into a into a gibberellicacid gibberellic acidpaste. paste.Typically, Typically, gibberellic gibberellic acid acid is prepared is prepared in a liquid in a liquid form form and and is is spread, spread, sprayedand/or sprayed and/or dispersed dispersed onto onto plants plants and/orand/or soil insoil in a diluted a diluted tank formulation tank formulation using using spraying spraying equipment(for equipment (forexample, example,a asprayer). sprayer).

[0007] While

[0007] While gibberellic gibberellic acidacid is sparingly is sparingly water-soluble water-soluble andand is is thustypically thus typicallyused usedatatlow low concentrationsso so concentrations it it cancan dissolve dissolve whenwhen diluted diluted in a solution in a solution to prepare to prepare a liquid aform, liquid that is, form, that is, about8 8grams about gramsperper 100 100 litres litres of water of water (which (which is thenistypically then typically applied applied to about to about aofhectare a hectare of plants). Thissolubility plants). This solubility is is typically typically sufficient sufficient to enable to enable an effective an effective amountamount of gibberellic of gibberellic acid to acid to

be appliedtotoplants. be applied plants.

[0008]The difficulty

[0008] The difficulty with formulating with formulating gibberellic gibberellic acid is dueacid is due to the fact to thegibberellic that fact that gibberellic acid acid is easily is degradedinto easily degraded into ineffective ineffective substances substances when diluted when diluted ineven in water, water, even at low at low concentrations. concentrations.

This degradation This degradation reduces reduces the effective the effective amountamount of gibberellic of gibberellic acid available acid available over over time to time exert itsto exert its effect on effect onplants. plants.AsAs a result, a result, it it isisnot notpossible possible to to prepare prepare aqueous aqueous formulations formulations of gibberellic of gibberellic

acid which acid haveaa commercially which have commerciallyacceptable acceptableshelf-life. shelf-life.

[0009] Prior

[0009] Prior art art gibberellicacid gibberellic acidcompositions compositions availableonon available themarket the market have have attempted attempted to to resolve theseissues resolve these issuesin in a variety a variety of of ways, ways, however however eachhasstill each still has disadvantages. disadvantages.

[0010] SomeSome

[0010] products, products, for example for example thosethose provided provided by Sumitomo by Sumitomo ChemicalChemical under theunder trade the trade name ProGibb name ProGibb SG SG and and ProGibb ProGibb SG Smartgrass, SG Smartgrass, are as are sold sold as solid solid products products whichwhich are dissolved are dissolved in in water immediatelybefore water immediately beforebeing beingapplied appliedtotoplants. plants. While Whilethese thesesolid solidproducts productshave havea a commercially commercially viable viable shelf-life, shelf-life, it difficult it is is difficult to to ensure ensure thatthat the the solid solid product product is fully is fully dissolved dissolved

(low water-solubility (low water-solubility leads leads to to slow slow dissolution) dissolution)and andthen thenevenly evenly mixed in the mixed in the large largevolume of volume of

the spray tank. tank. The incompletedissolution The incomplete dissolutionoror uneven unevenmixing mixingof of thespray the spraytank tankleads leadstoto insufficient or insufficient oruneven uneven application application of treatment of the the treatment to theto the plants. plants.

[0011] Other

[0011] Other products products overcome overcome the incomplete the incomplete dissolution dissolution difficulty difficulty by preparing by preparing a a concentrated non-aqueous concentrated non-aqueousliquid liquidformulation. formulation.ForFor example, example, a product a product by by Victorian Victorian Chemical Chemical

Company(VicChem) Company (VicChem) underthe under the trade trade name GALATM name GALA Growth Growth Regulator Regulator usesuses a 10% a 10% oil oil solution solution

becausethe because thegibberellic gibberellic acid acid is more is more soluble soluble and stable and stable in the in theHowever oil. oil. However the productthe product necessarily forms necessarily an emulsion forms an emulsionwhen whenit itis is added addedtoto water water for for administration administration to to plants plants because because the

oil is oil is not not miscible withwater. miscible with water. Application Application of an of an emulsion emulsion to plantstocan plants lead can lead to uneven to uneven applicationofofthe application thetreatment treatment to the to the plants. plants.

ME_166604682_2

3

[0012] Another Another liquidproduct, product, ProGibb ProGibb GA from Sumitomo SumitomoChemical, Chemical, contains contains over over 60% 2020200088 06 Jan 2020

[0012] liquid GA from 60%

ethanol or ethanol or methanol, whichresults methanol, which results in in the the product product being being toxic, toxic, hazardous hazardous and flammable,and and flammable, anditit maycause may causeheadaches headachesin inusers. users.While While thisproduct this productisiswater-miscible, water-miscible,the thegibberellic gibberellic acid acid has has poor stability in the alcohol at room temperature. poor stability in the alcohol at room temperature.

[0013] Accordingly,

[0013] Accordingly, there there remains remains the need the need for afor a liquid liquid product product containing containing gibberellic gibberellic acid acid

that isisstable that stableand andmore more easily easilymixed mixed into into aaspray spraytank tanktotoprovide providea asufficiently homogeneous sufficiently homogeneous

solution, which can be more evenly applied with coverage of all plants. Additionally, there is a solution, which can be more evenly applied with coverage of all plants. Additionally, there is a

need for need for such such aa water-miscible compositiontotoavoid water-miscible composition avoidusing usingtoxic toxicand/or and/orflammable flammablesubstances, substances, such as such as methanol/ethanol. methanol/ethanol.

Summary Summary of of theinvention the invention

[0014] Disclosed

[0014] Disclosed herein herein is aiswater-miscible a water-miscible composition composition of gibberellic of gibberellic acidacid forfor enhancing enhancing

plant growth. plant Thecomposition growth. The composition comprises comprises of gibberellicacid of gibberellic acidwith withoneoneorormore more glycols. glycols.

[0015] The The

[0015] glycols, glycols, preferably preferably propylene propylene glycol, glycol, havehave beenbeen found found to enable to enable the the production production of of a non-aqueous a water-miscibleformulation non-aqueous water-miscible formulationofofgibberellic gibberellicacid. acid. Further, Further, aa water-miscible water-miscible compositionofofgibberellic composition gibberellic acid acid and one or and one or more glycols has more glycols has been beenfound foundtotoform forma aclear clear solution solution whendiluted when diluted in in water, water, which whichisis stable stable and and homogenous. homogenous. TheThe water-miscible water-miscible composition composition of of gibberellic acid gibberellic acid and and one one or or more glycols can more glycols can thus thus be be diluted diluted with with water water and and then then evenly evenly applied applied

with coverage of all plants. with coverage of all plants.

Brief Description Brief DescriptionofofDrawings Drawings

[0016] Figure

[0016] Figure 1 shows 1 shows a perspective a perspective viewview of a of a water-miscible water-miscible composition composition according according to theto the invention (left) and a prior art gibberellic acid composition, GALATM Growth Regulator (right), invention (left) and a prior art gibberellic acid composition, GALA TM Growth Regulator (right),

both in water. both in water.

Detailed description Detailed description

[0017] As used

[0017] As used herein, herein, the the following following terms terms havehave the the meanings meanings ascribed ascribed to them. to them.

[0018] "Enhancing

[0018] "Enhancing plantplant growth" growth" refers refers to promoting, to promoting, increasing increasing and/or and/or improving improving the of the rate rate of growth of plants and/or its growth patterns, and/or promoting and/or increasing the size of growth of plants and/or its growth patterns, and/or promoting and/or increasing the size of

plants. plants.

ME_166604682_2

[0019] "Gibberellic "Gibberellic acidacid 90%" refers to gibberellic acid at at 90% purity.Gibberellic Gibberellic acid is is 06 Jan 2020

[0019] 90%" refers to gibberellic acid 90% purity. acid

typically used typically used in in product product compositions at 90% compositions at purity, and 90% purity, and therefore therefore requires requires about about 110-111g/L 110-111g/L

of gibberellic of gibberellicacid acidtotobebeused usedinin a composition a compositiontotogive givea a OOg/L 100g/Lcomposition. However,the composition. However, the personskilled person skilledininthe theartartwill willunderstand understand that that any form any form of gibberellic of gibberellic acid mayacid maywith be used be used the with the amountsvaried amounts variedtoto provide provide the the desired desired concentration. concentration.

2020200088 [0020] "Plants"

[0020] "Plants" refer refer to to a livingorganism a living organism thatgrows that grows in in earth,inin water, earth, water, and/or and/or from fromother other plants, typically plants, typicallyfrom from a permanent a permanent site, site, absorbs absorbs water water and/or inorganic and/or inorganic substancessubstances through its through its roots, and/or roots, and/orsynthesises synthesises nutrients nutrients by photosynthesis. by photosynthesis.

[0021] Disclosed

[0021] Disclosed herein herein is aiswater-miscible a water-miscible composition composition of gibberellic of gibberellic acidacid forfor enhancing enhancing

plant growth. plant It has growth. It has been found that been found that a composition comprisinggibberellic composition comprising gibberellic acid acid with withone oneor or more more glycols forms glycols forms aa water-miscible compositionwhich water-miscible composition which then then forms forms a clearsolution a clear solutionwhen when diluted diluted in in

water(as water (asitit would would be be in in a spray a spray tanktank solution). solution).

[0022] The The

[0022] glycols, glycols, preferably preferably propylene propylene glycol, glycol, havehave beenbeen found found to enable to enable the the production production of of a non-aqueous a water-miscibleformulation non-aqueous water-miscible formulation ofof gibberellicacid. gibberellic acid. Further, Further, aa water-miscible water-miscible compositionofofgibberellic composition gibberellic acid acid and one or and one or more glycols has more glycols has been beenfound foundtotoform forma aclear clear solution solution whendiluted when diluted in in water, water, which is stable which is stable and and homogenous. homogenous. TheThe water-miscible water-miscible composition composition of of gibberellic acid gibberellic acid and and one one or or more glycols can thus be more glycols be diluted diluted with with water water and and then evenly applied evenly applied

with coverage with coverage of ofall all plants. plants.The The water-miscible water-miscible composition cancomprise composition can comprisegibberellic gibberellicacid acid in in concentrations of concentrations of at at least least2 2%w/v %w/v of the the total totalcomposition, composition,with with concentrations concentrations of ofover over20 20 %w/v %w/v

possible, and possible, andstill stillform forma clear a clearsolution solution when when diluted diluted in water. in water.

[0023] Examples

[0023] Examples of suitable of suitable glycols glycols for for use use in the in the invention invention include:propylene include: propylene glycol, glycol,

diethylene glycol, diethylene glycol, dipropylene glycol and dipropylene glycol glycol ethers and glycol ethers (such (such as as diethylene diethylene glycol glycol mono butyl mono butyl

ether). Propylene ether). glycol is Propylene glycol is aa non-toxic non-toxic compound which compound which is is widely widely used used in in human human medicines. medicines.

Accordingly, propylene Accordingly, propyleneglycol glycolisis the the preferred preferred glycol glycol for the the water-miscible water-miscible composition composition

accordingtotothetheinvention. according invention.

[0024] The The

[0024] water-miscible water-miscible composition composition can becan be prepared prepared by mixing by mixing gibberellic gibberellic acid acid and and propyleneglycol propylene glycol (or (or another another glycol glycol such such as as diethylene diethylene glycol glycol or or dipropylene dipropylene glycol) glycol) together at together at a temperature a in the range temperature in range from 30°Ctoto 60°C from 30°C 60°Cand andthen thenallowing allowing themixture the mixture totostand standfor foraa perioduntil period untila aclear clearsolution solutionof of gibberellic gibberellic acidacid is formed. is formed. This composition This composition is physically is physically and and chemically chemically stable. stable.

ME_166604682_2

5

[0025] The The water-miscible composition according to thetoinvention the invention is able to form a stable 2020200088 06 Jan 2020

[0025] water-miscible composition according is able to form a stable

and homogeneous and homogeneous solution solution when when diluted diluted with with water, water, andand thus thus capable capable of being of being sufficiently sufficiently

and/or evenly and/or evenly applied applied to to plants plants to toenhance enhance their theirgrowth. In certain growth. In certain embodiments, the water- embodiments, the water miscible composition miscible compositioncomprises comprisesgibberellic gibberellicacid acidatat aa concentration concentration of of between between22toto 50 50 %w/v %w/vofof

the total the totalcomposition, composition, more preferably 22 to more preferably to 30 30 %w/v. %w/v. InInsome some embodiments, embodiments, the the water-miscible water-miscible

compositioncomprises composition comprisesgibberellic gibberellicacid acidat at aa concentration concentration of of between between 55 to 25 %w/v to 25 %w/vofof thetotal the total composition. InInone composition. oneembodiment, embodiment,thethe water-miscible water-miscible composition composition comprises comprises gibberellic gibberellic acid acid at at a concentration a concentration of about 20 %w/v %w/v ofofthe thetotal total composition. composition. InInanother anotherembodiment, embodiment,thethe water water-

miscible composition miscible compositioncomprises comprisesgibberellic gibberellicacid acidatat aa concentration concentration of of about about 10 10 %w/v %w/v ofof thetotal the total composition. composition.

[0026] In certain

[0026] In certain embodiments, embodiments, the water-miscible the water-miscible composition composition comprises comprises the onethe orone or more more glycols at glycols at aa concentration concentration of of between 50 to between 50 to 98 98 %w/v %w/v ofofthe the total total composition. Inone composition. In one embodiment,the embodiment, thewater-miscible water-misciblecomposition composition comprises comprises the the one one or more or more glycols glycols at aat a concentration of concentration of between 70toto 98 between 70 98%w/v %w/vof of thetotal the totalcomposition. composition.InInanother anotherembodiment, embodiment, the the

water-miscible compositioncomprises water-miscible composition comprises thethe one one or or more more glycols glycols at at a a concentrationofof concentration about7575toto about

90 %w/v 90 thetotal %w/vofofthe total composition. composition. InInone oneembodiment, embodiment,thethe water-miscible water-miscible composition composition

comprises the comprises the one one or or more moreglycols glycolsatat aa concentration concentration of of 90 90 %w/v. %w/v.InInanother anotherembodiment, embodiment, the the water-miscible compositioncomprises water-miscible composition comprises thethe one one or or more more glycols glycols at at a a concentrationofof concentration 8080 %w/v. %w/v.

[0027] The The

[0027] water-miscible water-miscible composition composition according according to thetoinvention the invention may may be be diluted diluted in water in water

andsprayed and sprayed onto onto plants. plants. For example, For example, it may it may be be to applied applied to particularly grasses, grasses, particularly during during winter to winter to increasegrowth increase growth where where it might it might lie dormant. lie dormant. It may It may also alsowith be used be used fruit with fruit crops, suchcrops, as grapes, such as grapes, citrus fruits citrus fruits and cherries, totoenhance and cherries, enhance growth growth during during their growing their growing seasons. seasons.

[0028] Figure

[0028] Figure 1 shows 1 shows a comparison a comparison of a water-miscible of a water-miscible composition composition according according to the to the invention and invention and aa commercially commerciallyavailable availablecomposition compositionofof gibberellicacid, gibberellic acid, GALA GALATM GrowthGrowth

Regulatorby by Regulator VicChem, VicChem, both both in inatwater water at a concentration a concentration suitable suitable for for administration administration to plants. to plants. Both compositions Both compositionscontain contain1010%w/v %w/v of gibberellicacid of gibberellic acidandand were were added added to water to water at at a rateofof8080 a rate

mLper mL per100 100litres litres of of water. The water-miscible water. The water-misciblecomposition composition according according to to theinvention the inventionininwater water is aaclear is clearsolution solutionwhereas whereas GALATM Growth GALA Growth Regulator Regulator in water in water was anwas an uneven uneven emulsion emulsion with with globules at globules at the the surface surfaceof ofthe thesolution. solution.This Thisdemonstrates demonstrates that thatthe thewater-miscible water-misciblecomposition composition

according to according to the invention invention produces produces aa more morestable stable and and homogenous homogenous spray spray tank tank solution, solution,

compared to compared to GALATM Growth GALA Growth Regulator. Regulator.

ME_166604682_2

6

[0029] The The Applicant also also found that that the the water-miscible composition according to theto the 2020200088 06 Jan 2020

[0029] Applicant found water-miscible composition according

invention has strong absorption properties, that is, good penetration into the leaves and uniform invention has strong absorption properties, that is, good penetration into the leaves and uniform

coverage, which coverage, whichaids aids the the composition compositiontotohave havea ahigh highefficacy efficacyin in enhancing enhancingplant plantgrowth. growth. Further, due to the fact that the active component is in its acidic form with a pH of about 3.0, the Further, due to the fact that the active component is in its acidic form with a pH of about 3.0, the

water-miscible compositionaccording water-miscible composition accordingtotothe theinvention inventiondoes doesnot notrequire requirepHpHadjustment adjustment when when in in

a spray water tank irrespective of the spray water's pH. In contrast, some prior art gibberellic a spray water tank irrespective of the spray water's pH. In contrast, some prior art gibberellic

acid formulations acid recommend formulations recommend that that acidifyingagents acidifying agentsareareused usedtotoadjust adjustthe the spray spraywater watertank tankto to an an optimumpHpH optimum of of between between 4.04.0 to to 4.54.5 (even (even when when the the spray spray water water tanktank hashas a pHa pH of about of about 6.0 6.0 to to neutral). neutral).

[0030] In some

[0030] In some embodiments, embodiments, the water-miscible the water-miscible composition composition according according to the invention to the invention

may be used with a wetting agent in the spray tank solution, however this is not essential to the may be used with a wetting agent in the spray tank solution, however this is not essential to the

efficacy of the composition according to the invention. This is in contrast to prior art efficacy of the composition according to the invention. This is in contrast to prior art

formulations which require the addition of a wetting agent to the spray tank solution. formulations which require the addition of a wetting agent to the spray tank solution.

Examples Examples

[0031] The The

[0031] following following examples examples are given are given to illustrate to illustrate thethe present present invention.It It invention. should should be be

understood, however, understood, however, that that the invention the invention is not is tonot to be limited be limited to the specific to the specific conditions conditions or detailsor details

described in described in these these examples, someofofwhich examples, some whichare arepreferred preferredembodiments embodiments of the of the invention. invention.

Example1 1 Example

[0032] The The

[0032] purpose purpose of this of this example example wasprepare was to to prepare a water-miscible a water-miscible composition composition comprising comprising

approximately1010%w/v approximately %w/vof of gibberellicacid gibberellic acidaccording theinvention accordingtotothe inventionfor forenhancing enhancingplant plant growth. The growth. Thematerials materialsand andtheir theirconcentrations concentrations used usedfor forthis this composition wereasasfollow: composition were follow:

TM 160 g/L Gibberellic Acid Gibberellic 90%pure Acid 90% pure 110 gg 110

Propylene Glycol Propylene Glycol 955 gg 955

Total Total IL 1L

[0033] ThisThis

[0033] water-miscible water-miscible composition composition according according toinvention to the the invention was prepared was prepared using using the the following method: following method:

(a) Gibberellic (a) Gibberellic acid acid andand propylene propylene glycol glycol are are added added to ato1La 1 L glass glass beaker. beaker.

(b) Gibberellic (b) Gibberellic acid acid andand propylene propylene glycol glycol are are mixed mixed and and heated heated to 50°C. to 50°C.

ME_166604682_2

7

(c) TheThe above beaker (b)cooled is cooled to 30°C and and allowed to stand untiluntil a clear 2020200088 06 Jan 2020

(c) above beaker (b) is to 30°C allowed to stand a clear

solutionisis formed. solution formed.

Example 2 Example 2

[0034] The The

[0034] purpose purpose of this of this example example wasprepare was to to prepare a water-miscible a water-miscible composition composition comprising comprising

approximately2020%w/v approximately %w/vof of gibberellicacid gibberellic accordingtotothe acidaccording theinvention inventionfor forenhancing enhancingplant plant growth. The growth. Thematerials materialsand andtheir theirconcentrations concentrations used usedfor for this this composition wereasasfollow: composition were follow:

TM 160A g/L Gibberellic Gibberellic Acid 90%pure Acid 90% pure 220 gg 220 DipropyleneGlycol Dipropylene Glycol 845 gg 845

Total Total 1L 1L

[0035] ThisThis

[0035] water-miscible water-miscible composition composition according according toinvention to the the invention was prepared was prepared using using the the following method: following method:

(a) Gibberellic (a) Gibberellic acid acid andand dipropylene dipropylene glycol glycol are are added added to ato1La 1L glass glass beaker. beaker.

(b) Gibberellic (b) Gibberellic acid acid andand dipropylene dipropylene glycol glycol are are mixed mixed and heated and heated to 50°C. to 50°C.

(c) TheThe (c) above above beaker beaker (b)cooled (b) is is cooled to 30°C to 30°C and allowed and allowed to stand to stand until until a clear a clear

solutionisis formed. solution formed.

Example33 Example

[0036] The The

[0036] following following example example reports reports on a on a trial trial carried carried outout to to investigatethe investigate theeffect effectof of treating plants, treating plants, namely namely phalaris phalaris grass, grass, in the in the Adelaide Adelaide Hills, Hills, South Australia South Australia in Augustin August 2018, 2018, with the water-miscible with the compositionaccording water-miscible composition accordingtotoExample Example 1 above 1 above compared compared to a to a prior prior art art

gibberellic acid gibberellic acid plant plantgrowth growth product, product, ProGibb SG,and ProGibb SG, anda acontrol control of of water. water. All All treatments treatments included aa wetting included agent. wetting agent.

[0037] The The

[0037] treatment treatment using using the the water-miscible water-miscible composition composition according according to Example to Example 1 1 contained gibberellic contained gibberellic acid acid at ataaconcentration concentrationof ofabout about10 10%w/v. Thiswas %w/v. This wasadded addedtotospray spraywater water at the at the rate rateofof8080mL mL per per 100 100 litres litresofof water. water.The Thewetting wetting agent, agent,Supa-wet Supa-wet 1000 fromAustralian 1000 from Australian Adjuvants,waswas Adjuvants, then then added added to thetospray the spray water water to to acreate create a total total of of 100oflitres 100 litres spray of spray water. water.

[0038] The The

[0038] treatment treatment using using ProGibb ProGibb SG contained SG contained gibberellic gibberellic acid acid at theatsame the same concentration concentration

of 10 %w/v, of wasadded %w/v, was added totospray wateratatthe spraywater thesame samerate, rate, and andused usedthe thesame samewetting agent,asasthe wettingagent, the water-miscible composition water-miscible compositionaccording accordingtotoExample Example 1. 1.

[0039] For For

[0039] the the control control treatment, treatment, only only thethe wetting wetting agent agent waswas added added to the to the water. water.

ME_166604682_2

8

[0040] For For eacheach treatment, the the compositions werewere administered to plants at aatrate a rate of of 8mL/ha 2020200088 06 Jan 2020

[0040] treatment, compositions administered to plants 80mL/ha

(or equivalent) (or equivalent) and and were sprayed out were sprayed out using using aa hand hand held held 33 mmSpray SprayBoom Boom once once at the at the startofofeach start each trial trial at at aa water rate of water rate of1OL/ha. 110L/ha.

[0041] The The

[0041] amount amount ofphalaris of the the phalaris grass grass growth growth was then was then measured measured by theby theofuse use an of an electronic plate meter at day 0 prior to its treatment, day 12 and day 23 after treatment electronic plate meter at day 0 prior to its treatment, day 12 and day 23 after treatment

commenced commenced with with thethe compositions compositions to determine to determine the the amount amount of grass of grass growth. growth. The results The results are are expressed as expressed as kilograms kilograms ofofdry dry matter matter per per hectare hectare (kg (kg DM/ha). DM/ha).TheThe amount amount of phalaris of phalaris grass grass

growth from growth fromthe thetreatment treatmentcontaining containingthe thewater-miscible water-misciblecomposition composition according according to to Example Example 1 1

was compared was comparedtotothat thatofofthe the treatment treatment containing containing Progibb ProgibbSGSGandand a control a control of of water,allallwith water, with Supa-wet1000. Supa-wet 1000.

[0042] The The

[0042] results, results, as as seen seen in in Table Table 1 1 below, below, demonstrate demonstrate thatthat thethe grasstreated grass treatedwith withthe the water-miscible composition water-miscible compositionaccording accordingtotoExample Example 1 yielded 1 yielded thethe greatestamount greatest amount of plant of plant growth growth

after 23 after 23 days days of of treatment treatment compared to grass compared to grass treated treated with with Progibb SGand Progibb SG andthe thecontrol. control. Accordingly, the Accordingly, the water-miscible water-miscible composition compositionaccording according to to theinvention the inventionhas hasa agreater greaterefficacy efficacy in in enhancing plant enhancing plant growth. growth.

Table 11 Table

Average growth over 23 Days Time (days) Control (kg Progibb SG Water-miscible DM/ha) (kg DM/ha) composition of gibberellic acid and propylene glycol (kg DM/ha) 00 1363 1363 1368 1368 1380 1380

12 12 1566 1566 2168 2168 2304 2304

23 23 1828 1828 2668 2668 2847 2847

Amount Amount ofof growth growth inin 465 465 1300 1300 1467 1467 23 days__________ 23 days Avg. amount Avg. of amount of 20.2 20.2 56.5 56.5 63.7 63.7 growth per day growth per day (kg/day) (kg/day) Cotok_____G_______

Example 44 Example

[0043] The The

[0043] following following example example reports reports on atrial on a trial carried outout carried to to investigate effectof theeffect investigatethe of treating plants, namely mixed grass, in Trafalgar, Victoria in July 2018, with the water-miscible treating plants, namely mixed grass, in Trafalgar, Victoria in July 2018, with the water-miscible

compositionaccordingtoExample1comparedtoapriorart composition g acidibberellic according to Example 1 compared to a prior art gibberellic plant acid plantgrowth growth

ME_166604682_2

9

product, GALA GALATM Growth Regulator by VicChem, and a and a control of water, all with no wetting 2020200088 06 Jan 2020

product, TM Growth Regulator by VicChem, control of water, all with no wetting

agent. agent.

[0044] The The

[0044] treatment treatment using using the the water-miscible water-miscible composition composition according according to Example to Example 1 1 contained gibberellic contained gibberellic acid acid at at aaconcentration concentrationof ofabout about 10 10%w/v. Thiswas %w/v. This wasadded addedtotospray spraywater water at the rate of 80 mL per1OL of water. at the rate of 80 mL per 100L of water.

[0045] The The

[0045] treatment treatment using using GALAGALATM Growth contained Growth Regulator Regulator gibberellic contained gibberellic acid at theacid at the sameconcentration same concentrationofof1010%w/v, %w/v,andand waswas added added to spray to spray water water at the at the same same rate,as asthe rate, thewater- water miscible composition miscible compositionaccording accordingtotoExample Example1. 1.

[0046] For For

[0046] the the control control treatment, treatment, only only water water waswas used. used.

[0047] For For

[0047] eacheach of the of the treatments, treatments, thethe compositions compositions werewere administered administered to plants to plants at aatrate a rateofof 8OmL/ha(or 80mL/ha (orequivalent) equivalent)and andwere weresprayed sprayed outusing out usinga 10 a 10m m Spray Spray Boom Boom once once at start at the the start of of each trial. each trial.

[0048] The The

[0048] amount amount ofmixed of the the mixed grass grass growth growth was measured was measured by the by the use useelectronic of an of an electronic plate plate meter at meter at week two, three, week two, three, four four and five after and five aftertreatment treatmentcommenced withthe commenced with thecompositions compositionsto to determine the determine the amount amountofofgrass grassgrowth. growth.TheThe resultsare results areexpressed expressedasaskilograms kilogramsofof drymatter dry matterper per hectare (kg DM/ha). hectare (kg The DM/ha). The amount amount of mixed of mixed grass grass growth growth from from the treatment the treatment containing containing the the

water-miscible compositionaccording water-miscible composition accordingtotoExample Example 1 was 1 was compared compared to that to that of the of the treatment treatment

containing GALA containing GALATM GrowthGrowth Regulator Regulator and a control and a control of only, of water water all only, all no with with no wetting wetting agent.agent.

[0049] The The

[0049] results, results, as as seen seen in in Table Table 2 below, 2 below, demonstrate demonstrate thatthat thethe grasstreated grass treatedwith withthe the water-miscible composition water-miscible compositionaccording accordingtotoExample Example 1 yielded 1 yielded thethe greatestamount greatest amount of plant of plant growth growth

after five after fiveweeks weeks of of treatment treatment compared to the compared to the grass grass treated treated with with GALATM Growth GALA TM Growth Regulator Regulator and and

the control. the control. Accordingly, the water-miscible Accordingly, the water-miscible composition compositionaccording accordingtotothe theinvention inventionhas hasa a greater efficacy in enhancing plant growth. greater efficacy in enhancing plant growth.

ME_166604682_2

10

2020200088 06 Jan 2020

Table 22 Table

Growth AveragesOver Growth Averages Over2323Days Days Time (weeks) Control (kg GALA Growth Water-miscible DM/ha) Regulator composition of (kg DM/ha) gibberellic acid and propylene glycol (kg DM/ha) 2 2 1153 1153 1140 1140 1226 1226

3 3 1171 1171 1271 1271 1398 1398

4 4 1222 1222 1253 1253 1459 1459

5 5 1363 1363 1368 1368 1652 1652

Amountofof Amount growth growth in in 5 5 210 210 228 228 426 426 weeks from weeks week 22 from week Avg. amountofofgrowth Avg. amount growth 10 10 10.8 10.8 20.3 20.3 per day per (kg/day) day (kg/day)

5 Example 5 Example

[0050] The The

[0050] following following example example on a on reports reports a trial trial carried outout carried to to investigate theeffect investigatethe effect of of Table Grapes treating Table treating in well-established vineyards Grapes in in Mildura, vineyards in Victoria in Mildura, Victoria in October 2018 with October 2018 with the water the water miscible compositionaccording miscible composition accordingtotoExample Example 1 above 1 above compared compared to a to a prior prior art art

gibberellic acid gibberellic acid plant plantgrowth growth product, product, ProGibb Liquid, and ProGibb Liquid, and aa control control of of water. All treatments water. All treatments

includeda awetting included wetting agent. agent.

[0051] The The

[0051] treatment treatment using using the the water-miscible water-miscible composition composition according according to Example to Example 1 1 contained gibberellic contained gibberellic acid acid at ata aconcentration concentrationof ofabout about10 10%w/v. This was %w/v. This wasadded addedtotospray spraywater water at the at the rate rateofof8080mL mL per per 100 100 litres litresofof water. water.The Thewetting wettingagent, agent,Agral Agralfrom from Syngenta, Syngenta, was then was then

addedtotothe added thespray spray water water at 1OmL at 10mL perof1OOL per 100L water of to water create to createofa 100 a total total of 100 litres litreswater. of spray of spray water. This was This was sprayed sprayedinin rows rowseach eachofof500 500vines. vines.

[0052] The The

[0052] treatment treatment using using ProGibb ProGibb Liquid Liquid SG containing SG containing gibberellic gibberellic acid acid at theatsame the same concentration was concentration wasadded addedtotospray spraywater wateratat the the same samerate, rate, and used the and used the same same wetting wettingagent, agent, as as the the water-miscible composition water-miscible compositionaccording accordingtotoExample Example 1. 1.

[0053] For For

[0053] the the control control treatment, treatment, only only thethe wetting wetting agent agent waswas added added to the to the water. water.

[0054] For For

[0054] eacheach treatment, treatment, the the compositions compositions werewere administered administered to plants to plants at aatrate a rate of of 8mL/ha 80mL/ha

(or equivalent) (or equivalent) and and were out using sprayed out were sprayed using aa Silvan Silvan TGS TGSTwin Twin onceonce Rowe Rowe at the at the start start of of each each

trial atat aa water trial water rate of 1200L/ha. rate of 1200L/ha.

ME_166604682_2

11

[0055] The The average size size of the grapes was was measured (ruler,), appearance (visual) and and the 2020200088 06 Jan 2020

[0055] average of the grapes measured (ruler,), appearance (visual) the

numberofofboxes number boxesper pervine vinecounted. counted.TheThe amounts amounts fromfrom the treatment the treatment containing containing the the water water-

miscible composition miscible compositionaccording accordingtotoExample Example 1 was 1 was compared compared to that to that of the of the treatment treatment containing containing

ProgibbLiquid Progibb Liquid and and a control a control of water, of water, all Agral. all with with Agral.

[0056] The The

[0056] results, results, as as seen seen in in Table Table 3 below, 3 below, demonstrate demonstrate thatthat thethe grapes grapes treatedwith treated with the the

water-miscible composition water-miscible compositionaccording accordingtotoExample Example 1 was 1 was bioequivalent bioequivalent withwith ProGibb ProGibb Liquid Liquid and and muchbetter much better than than the the control. control. Accordingly, Accordingly, the the water-miscible water-miscible composition compositionaccording according to to the the

invention has invention has a good efficacy in good efficacy in enhancing plant growth enhancing plant growthafter after 15 15 weeks weekswith withnone noneofofthe the stability and stability andphysical physicalproblems problems of the the ProGibb Liquid. ProGibb ProGibb Liquid. ProGibbLiquid, Liquid,contains containsover over 60% 60%

ethanol or methanol, ethanol whichresults methanol, which results in in the the product product being being toxic, toxic, hazardous hazardous and flammable,and and flammable, anditit maycause may causeheadaches headachesin inusers. users.Further, Further,while whileProGibb ProGibb Liquid Liquid is is water-miscible,thethegibberellic water-miscible, gibberellic acid has acid has poor stability ininthe poor stability alcohol the at at alcohol room roomtemperature. temperature.The The composition accordingtoto the composition according the inventionavoids invention avoidsthethe need need for use for the the of useethanol of ethanol or methanol. or methanol.

[0057] No adverse

[0057] No adverse effects effects on the on the grapes grapes werewere seen. seen.

Table 33 Table

Average growth Average growthover over2323Days Days Time (days) Control (kg DM/ha) ProGibb Liquid Water-miscible composition of gibberellic acid and propylene glycol

Appearance Appearance markingororyellowing No marking No yellowing No marking No markingororyellowing yellowing Nomarking No markingororyellowing yellowing Averagegrape Average grape sizeml ml size 16-18 16-18 18-22 18-22 18-22 18-22

No. boxes No. boxesper pervine vine 1.25 1.25 >> 1.5 1.5 >1.5 >1.5

[0058] The The

[0058] wordword 'comprising' 'comprising' and forms and forms of theof the 'comprising' word word 'comprising' as usedasin used thisindescription this description andinin the and theclaims claimsdoes does notnot limit limit the the invention invention claimed claimed to exclude to exclude any or any variants variants or additions. additions.

[0059] Modifications

[0059] Modifications and and improvements improvements to thetoinvention the invention will will be be readily readily apparent apparent to those to those

skilled in skilled inthe theart. Such art. Suchmodifications modificationsand andimprovements are intended improvements are intended to to be be within within the the scope of scope of

this invention. this invention.

ME_166604682_2

Claims (6)

1. The claims defining the invention are as follows: 09 Sep 2025

   1 A water-miscible composition for enhancing plant growth consisting of:

   (a) gibberellic acid GA3; and

   (b) one or more glycols selected from the group consisting of propylene glycol, diethylene glycol, dipropylene glycol and mixtures thereof, 2020200088

   wherein the gibberellic acid GA3 is present in the composition at a concentration between 2% to 30 % w/v of the total composition;

   wherein the one or more glycols is present at a concentration of between 70 to 98 %w/v of the total composition; and

   wherein the gibberellic acid GA3 is dissolved in the one or more glycols to form a clear solution.
2. 2 The water-miscible composition according to claim 1, wherein the gibberellic acid A3 is present at a concentration of between 5 to 25 %w/v of the total composition, and the one or more glycols is present at a concentration of between 75 to 95 %w/v of the total composition.
3. 3 The water-miscible composition according to claim 2, wherein the gibberellic acid GA3 is present at a concentration of about 20 %w/v of the total composition, and the one or more glycols is present at a concentration of about 80 %w/v of the total composition.
4. 4 The water-miscible composition according to claim 2, wherein the gibberellic acid GA3 is present at a concentration of about 10 %w/v of the total composition, and the one or more glycols is present at a concentration of about 90 %w/v of the total composition.
5. 5 A method for formulating a water-miscible gibberellic acid composition for enhancing plant growth according to any one of claims 1 to 4 comprising combining gibberellic acid GA3 with one or more glycols, and then standing the mixture until a clear solution is formed.
6. 6 A method for enhancing plant growth comprising adding a water-miscible gibberellic acid composition for enhancing plant growth according to any one of claims 1 to 4 to a spray solution and applying the spray solution to one or more plants.