composition

Abstract

The present disclosure relates to a composition comprising a polyethyleneoxide alkyl ether according to the formula (I): R1-O-(CH2CH2O)n-H, wherein R1 represents an alkyl group comprising z or z+2 carbon atoms, wherein z is 12, 14, 16 or 18; wherein the weight ratio of compounds of formula (I) comprising a Cz alkyl moiety to compounds of formula (I) comprising a Cz+2 alkyl moiety is in the range of 95:5 to 100:0; and wherein n represents an average number of from 6 to 22.

Description

[0001] 1

[0002] Composition

[0003] Field of the Invention

[0004] The present invention relates generally to a polyethoxylated fatty alcohol ether as non-ionic Alcohol Ethoxylate compounds (AE) for use in compositions for agricultural applications, and to compositions comprising an active agrochemical ingredient and a polyethoxylated fatty alcohol ether composition.

[0005] Background of the Invention

[0006] Surfactants generally possess both hydrophilic, i.e. polar charged or uncharged head moieties and hydrophobic, i.e. non-polar hydrocarbon tail moieties, and therefore are generally considered as amphipathic molecules, which can reduce interfacial tension and stabilize foams and / or emulsions. Alcohol ethoxylates (AE) are a major class of non-ionic surfactants which are widely used in laundry detergents, household cleaners, institutional and industrial cleaners, cosmetics, in textile, paper, oil and other process industries, and typically combine impressive adsorptive capacity. AE are generally employed as industrial grade polydisperse mixtures of analogue compounds with different carbon chain lengths, typically owing to their origin from naturally occurring fatty acid alcohol products or from polydisperse petrochemical sources such as the Fischer-Tropsch process.

[0007] One of the applications of AE is in agricultural applications, in particular in agrochemical formulations comprising agrochemically active ingredients, which are commonly used to improve crop yield and to protect against pests and diseases. Herein, non-ionic alcohol ethoxylate (AE) surfactants are typically employed as co-formulants and adjuvants.

[0008] Formulation and adjuvant properties, biodegradability, irritancy and toxicity of AE strongly depend on their chemical structure, and have an impact on the efficacy of the agrochemical formulations as well.

[0009] To date, almost all published toxicity data is based on industrial grade polydisperse mixtures of surfactant analogues, making the specific structure-toxicity relationship difficult to elucidate. With increasingly stringent regulatory requirements on co-formulants it is therefore desirable to develop new surfactants with lower irritancy. However, in the absence of a thorough understanding of the structure-irritancy-performance relationship, this is difficult to predict, or even to determine rationally. 2

[0010] For instance, polyoxyethylene Lauryl Ether, also commonly known as polyethylenglycol(- 23)lauryl ether or Brij 35 under CAS-Number 9002-92-0, is an example of a polydisperse industrial grade AE surfactant commonly used in the agrochemical industry. This surfactant is typically prepared by an ethylene oxide addition to alkyl alcohol mixtures derived from naturally occurring fatty acids, and hence typically comprises a polydisperse alkyl ether moiety with different carbon chain lengths, ranging from 10 to 16 carbon atoms, with the majority of the compounds having 12 and 14 carbon atom alkyl ether moieties. A blend of alcohols is typically reacted with ethylene oxide under caustic conditions to obtain a product of the ethylene oxide addition to the alcohol, which is subsequently hydrolysed. Usually, due to the reaction scheme, the ethylene oxide addition product may therefore contain of from 0.01% by mass to 1% by mass of an alkali metal hydroxide relative to the total mass of the ethylene oxide addition product.

[0011] Polyoxyethylene Lauryl ethers are regularly used as surfactants for agrochemicals due to their ability to enhance the dispersion effectiveness, but also due to the increases seen in agrochemical performance. However, it was found that the industrial grade surfactants may trigger irritation on skin, eyes and respiratory apparatus of agricultural workers and consumers. Applicants found that in particular commercially available polydisperse polyoxyethylene lauryl ether, in particular Brij35, solicited eye irritancy, as confirmed by an in vitro human corneal cell irritancy assay.

[0012] Accordingly, there remains a need for surfactant compositions with improved safety and reduced eye irritancy while still providing efficacy in agricultural applications, in particular while maintaining adjuvancy performance for the agrochemical compositions. Furthermore there remains the requirement to provide for a platform surfactant blend with reduced eye irritation.

[0013] Summary of the Invention:

[0014] In a first aspect, the present disclosure relates to a composition comprising a polyethyleneoxide alkyl ether according to the formula (I):

[0015] R1-O-(CH2CH2O)n-H (I), wherein R1represents an alkyl group comprising z or z+2 carbon atoms, wherein z is 12, 14, 16 or 18; wherein the weight ratio of compounds of formula (I) comprising a Czalkyl moiety to compounds of formula (I) comprising a Cz+2 alkyl moiety is in the range of 95:5 to 100:0; and wherein n represents an average number of from 6 to 22. 3

[0016] Preferably n represents an average number of from 6 to 16 or an average number of from 15 to 22.

[0017] Preferably, the composition comprises a polyethyleneoxide alkyl ether according to the formula (I):

[0018] R1-O-(CH2CH2O)n-H (I), wherein R1represents an alkyl group comprising 12 or 14 carbon atoms, n represents an average number of from 10 to 16, wherein the weight ratio of compounds wherein R1is a Ci2alkyl group to compounds wherein R1is a C14 alkyl group is in the range of 95:5 to 100:0.

[0019] In a further aspect, the present disclosure relates to a method for preparing an agricultural composition with reduced eye irritancy, comprising: i.) providing an active agrochemical ingredient; and ii.) contacting the active ingredient with a polyethyleneoxide alkyl ether according to the present disclosure.

[0020] In a further aspect, the present disclosure relates to a method for improving plant yield and / or improving plant health, comprising contacting foliage, or locus of a plant or plant propagation material with a biologically effective amount of a composition according to any of the present disclosures.

[0021] In a further aspect, the present disclosure relates to the use of a the polyethyleneoxide alkyl ether composition according to the present disclosure as a co-formulant in an agrochemical composition comprising at least one agrochemically active ingredient.

[0022] In a further aspect, the present disclosure relates to a process for the reducing the eye irritancy of a polydisperse polyethyleneoxide alkyl ether according to formula (I):

[0023] R1-O-(CH2CH2O)n-H (I), wherein R1represents an alkyl group comprising z or z+2 carbon atoms, wherein z is 12, 14, 16 or 18, wherein n represents an average number of from 6 to 22, by enriching the content of compounds of formula (I) comprising a Czalkyl moiety.

[0024] Preferably n represents an average number of from 6 to 16 or an average number of from 15 to 22.

[0025] Preferably, the polydisperse polyethyleneoxide alkyl ether is according to formula (I): 4

[0026] R1-O-(CH2CH2O)n-H (I), wherein R1represents an alkyl group comprising 12 or 14 carbon atoms, n represents an average number of from 10 to 16, and the process enriches the content of compounds wherein R1is a Ci2alkyl group.

[0027] Detailed Description of the Invention:

[0028] The present invention provides a polyethyleneoxide fatty alcohol ether composition with reduced eye irritancy and good dispersion and adjuvant properties, for use with agrochemically active ingredients.

[0029] Applicants surprisingly found that the eye irritancy could be strongly reduced when the content of compounds comprising Cz+2 alkyl moieties relative to Czalkyl moieties as defined above and herein was reduced. Accordingly, applicants found that by minimizing the Cz+2alkyl moiety content of the surfactant, a resultant composition exhibits reduced eye irritancy, while the thus changed composition allows to maintain efficacy in agricultural applications.

[0030] Accordingly, the compositions according to the present invention provide an acceptable comparative performance, while strongly reducing the potential for eye irritation during application.

[0031] The composition according to the present invention comprises an active agrochemical ingredient and polyethyleneoxide alkylether with reduced content of Cz+2-alkyl moiety derived ethers as compared to commercial polydisperse compositions.

[0032] The active agrochemical ingredient may include pesticides, herbicides, fungicides, or plant growth regulators, among others. The polyethyleneoxide alkyl ether serves as a surfactant to facilitate the dispersion and effectiveness of the active ingredient.

[0033] In one embodiment, the polyethyleneoxide alkyl ether used in the composition has reduced Cz+2alkyl moiety content compared to conventional surfactants. Reduction in Cz+2alkyl moiety content can be achieved through purification processes or selection of starting materials with lower Cz+2alkyl moiety content.

[0034] Advantageously, the weight ratio of compounds of formula (I) comprising a Czalkyl moiety to compounds of formula (I) comprising a Cz+2alkyl moiety is in the range of 98:2 to 99.9:0.1 ; in the range of 98.1 :1.9 to 99.8:0.2, or in the range of 98.2:1.8 to 99.7:0.3, in the range of 5

[0035] 98.3:1.7 to 99.6:0.4, in the range of 98.4:1.6 to 99.5:0.5; in the range of 98.5:1.5 to 99.4:0.6; in the range of 98.6:1.4 to 99.3:0.7; in the range of 98.7:1.3 to 99.2:0.8; in the range of 98:2. :1.2 to 99.1 :0.9; or in the range of 98.9:1.1 to 99.0:1.0.

[0036] Advantageously, the weight ratio of compounds wherein R1is a C12 alkyl group to compounds wherein R1is a C14 alkyl group is in the range of 98:2 to 99.9:0.1 ; in the range of 98.1 :1.9 to 99.8:0.2, or in the range of 98.2:1.8 to 99.7:0.3, in the range of 98.3:1.7 to 99.6:0.4, in the range of 98.4:1.6 to 99.5:0.5; in the range of 98.5:1.5 to 99.4:0.6; in the range of 98.6:1.4 to 99.3:0.7; in the range of 98.7:1.3 to 99.2:0.8; in the range of 98:2. :1.2 to 99.1 :0.9; or in the range of 98.9:1.1 to 99.0:1.0.

[0037] In an embodiment, the composition further comprises a polyethyleneoxide alkyl ether according to the formula (I) as component (a) and an agrochemically active ingredient (b), wherein (b) is present in an agrochemically active amount.

[0038] The composition of the present invention may typically contain as little as about 0.01 % to as much as about 95% or more by weight of each active ingredient. Preferably, the composition contains from 1% to 10% of each active ingredient. In a particularly preferred embodiment, the active ingredient is present in the composition from 0.5 to 10% w / v, more preferably from 0.5 to 5% w / v, wherein the sum of the individual ingredients in the composition is 100%.

[0039] Advantageously, the weight / weight ratio of component (a) to component (b) is in the range of from 1 :3 to 1 :100.

[0040] Advantageously, the polyethyleneoxide alkyl ether is present in an amount ranging from 0.1% to 10% by weight of the composition.

[0041] Advantageously, the agrochemically active ingredient is selected from pesticides, herbicides, fungicides, and plant growth regulators, and mixtures thereof.

[0042] The composition may include additional adjuvants, stabilizers, or inert ingredients commonly used in agrochemical formulations. These additional components can be selected based on factors such as compatibility with the active ingredient and the desired application method.

[0043] In a preferred embodiment, the composition further comprises at least one of additional adjuvants, stabilizers, or inert ingredients commonly used in agrochemical formulations. 6

[0044] The composition can be formulated in various forms, including liquid concentrates, emulsifiable concentrates, suspensions, or granules. The formulation may be adapted for application by spraying, irrigation, seed treatment, or other suitable methods depending on the intended use and crop type.

[0045] Advantages of the present invention include reduced eye irritancy associated with the lower Cz+2 content of the surfactant, while maintaining or enhancing the efficacy of the active agrochemical ingredient. By providing a safer alternative to conventional compositions, the invention contributes to promoting the health and safety of agricultural workers and consumers.

[0046] The composition described herein offers a novel formulation for agricultural applications, comprising an active agrochemical ingredient and polyethyleneoxide alkyl ether with reduced Cz+2 content, reducing eye irritancy. The invention addresses the need for safer agrochemical formulations, thereby enhancing the health and safety of agricultural workers and consumers.

[0047] Using a commercially available industrial grade polyoxyethylene lauryl ether, also known as Brij 35, as an example of a typical polydisperse industrial grade AE surfactant, applicants found that it was possible to reduce the irritancy in an in vitro human corneal cell irritancy assay while maintaining adjuvancy performance in a bioassay, by removing or reducing the presence of a particular component from the polydisperse mixture.

[0048] More specifically composition analysis showed that a polyoxyethylene lauryl ether surfactant contains Ci2Enand Ci4En, wherein n represents 15 to 22, and that by removing the Ci4Encomponents, and thus bringing the material closer to the nominal structure of polyoxyethylene lauryl ether, were able to achieve a significantly lower irritancy but equally efficacious material with nominal structure.

[0049] Preferably, the alkyl moiety may be linear and / or saturated or unsaturated.

[0050] Surprisingly, it has also been determined that a composition with a lower Cz+2 alkyl moiety content provides identical performance in terms of applicability and active biological performance, while having an inherently improved eye compatibility and reduced irritation of formulation.

[0051] The composition of the present invention can be a "solid" formulation, for example, a water dispersible granule (WG) but is preferably a liquid composition. In a preferred embodiment the 7 median particle size diameter of the active ingredient in the liquid composition is about two microns or less, as compositions comprising particles of this size have been shown to exhibit improved physical stability.

[0052] The composition of the present invention may further comprise one or more additional components, for example surfactants, including anionic and non-ionic surfactants. Examples of such surfactants include, alkyl sulfonates, alkylbenzene sulfonate salts, alkylnaphthalenesulfonate salts, lignin sulfonates, polyarylphenols polyoxyethylene glycol alkyl ethers, polyarylphenyl ether phosphates and sulphates, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyetylene fatty acid esters, polyoxypropylene fatty acid esters, polyoxyethylene sorbitan fatty acid esters; polyoxyethylene styryl phenyl ethers, polycarboxylates; dialkyl-sulfosuccinates, alkyl diglycol ether sulfates, polyoxyethylene alkylaryl ether sulfates, phosphoric acid esters, polyoxyethylene hydrogenated castor oils, benzoates, fatty acid polyglycerides, glycerine fatty acid esters, sorbitan monooleates, polyoxyethylene sorbitan monolaurates, fatty acid alcohol polyglycol ethers, salts of alkyl sulfates, soaps, dialkyl esters of sulfosuccinate salts, alkyl polyglycoside, quaternary amines, block copolymers of ethylene oxide and propylene oxide, salts of mono and dialkyl phosphate esters, alkylene glycol alkyl ethers etc. Other additional formulation components such as an antifoam, a structuring agent (e.g a thickener), a solid carrier or a filler may also be included in the formulation of the present invention. Examples of such components include carboxymethylcellulose, xanthan gum, pyrogenic silica, precipitated silica, diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, starch, sodium carbonate, sodium bicarbonate, zeolite etc.. The quantity of these additional formulation components in the herbicidal composition is typically from 0.5% to 30% w / v.

[0053] The composition of the present invention may further comprise a vegetable oil and / or a mineral oil and / or an alkyl ester. Examples of vegetable oils include, for example, olive oil, kapok oil, castor oil, papaya oil, camellia oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, rapeseed oil, cottonseed oil, soybean oil, linseed oil, sunflower and safflower oil and fatty acids originated therefrom and alkylesters of the fatty acids. Rape seed oil methyl ester (MRSO) is particularly preferred. Mineral oils include, for example, paraffin such as liquid paraffin and paraffin petroleum. Alkyl esters include, for example, alkylacetates.

[0054] The composition of the present invention may further comprise a quantity of water. Advantageously, the water content is in the range of from 0.5 to 75% v / v, more preferably from 0.5 to 73% v / v and even more preferably from 0.5 to 70% v / v. The water may be introduced 8 into the agrochemical composition by addition at a suitable stage in the manufacture, or by using either of the active ingredients as a "wet paste" in the preparation of the composition.

[0055] The composition of the present disclosure may comprise at least a first pesticidal ingredient, for example a herbicide, fungicide or insecticide.

[0056] In a preferred embodiment, the composition comprises a herbicidal compound. More preferably, the composition comprises Pinoxaden as herbicidally active compound. Pinoxaden is also known as 8-(2,6-Diethyl-p-tolyl)-1 ,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1 ,2- d][1 ,4,5]oxadiazepin-9-yl-2,2-dimethylpropionate.

[0057] Preferably, the composition comprises nicosulfuron as herbicidally active compound. Nicosulfuron is also known as

[0058] 2-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-N,N-dimethylnicotinamide.

[0059] The method of the invention may often be practiced by preparing a concentrated composition comprising a pesticide and the AE. Various additives, including detergents, emulsifiers and dispersing agents may be added along with an agriculturally acceptable carrier to provide the desired concentration of active agent for application to plants.

[0060] In a preferred embodiment, the method of preparation of the composition for application comprises the steps of 1) adding the surfactant to the agrochemically active composition and 2) adding to the composition prepared in step 1 to an agriculturally acceptable carrier, to provide a composition comprising the agrochemically active composition and the adjuvant, in a agrochemically active amount for application.

[0061] The content of the additional pesticidal ingredient in the composition is typically 0.2 - 40%, preferably 0.5 - 20% by weight.

[0062] The composition of the present invention can also be used as a mixture together with or in combination with other agricultural chemicals, tank-mix adjuvants, crop oil concentrates, fertilizers and / or safeners.

[0063] The composition of the present invention is preferably a liquid "pre-mix" formulation - that will be diluted prior to use. 9

[0064] The present invention further provides a method for the preparation of an herbicidal composition of the present invention comprising mixing together, simultaneously or sequentially in any order the components.

[0065] The present invention still further provides a method of controlling undesirable vegetation at a locus which comprises diluting a herbicidal composition according to the present invention with water and applying a weed controlling amount of the diluted composition to the locus. The application of the composition may vary within wide limits and depends on the nature of the soil, the method of application (pre- or post-emergence; seed dressing; application to the seed furrow etc), the crop plant, the undesirable vegetation to be controlled, the prevailing climatic conditions and other factors.

[0066] The locus may include both "desirable" and "undesirable" vegetation. Desirable vegetation is for example a crop which is substantially unaffected by the herbicide application. Examples of crops include for example perennial crops such as citrus fruit, grapevines, nuts, oil palm, olives, pome fruit, stone fruit and rubber, and annual arable crops, such as cereals, for example barley and wheat, cotton, oilseed rape, maize, rice, soybeans, sugar beet, sugar cane, sunflowers, ornamentals and vegetables. The compositions of the present invention are particularly suited for controlling undesirable vegetation in maize. The undesirable vegetation my include weeds including monocotyledonous species, for example Agrostis, Alopecurus, Avena, Bromus, Cyperus, Digitaria, Echinochloa, Lolium, Monochoria, Rottboellia, example Abutilon, Amaranthus, Chenopodium, Chrysanthemum, Galium, Ipomoea, Nasturtium, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium.

[0067] The term "crop" is to be understood as also including a crop which has been genetically modified and in particular one which has been rendered tolerant to herbicides or classes of herbicides.

[0068] Preferably, the process for preparation may comprise separating the components of the polydisperse polyethyleneoxide alkyl ether according to the formula (I) by the chain length of the alkyl moiety, and removing compounds wherein R1represents an alkyl group comprising z+2 carbon atoms, n represents an average number of from 6 to 22, preferably n represents an average number of from 6 to 16 or an average number of from 15 to 22, to obtain a composition enriched in compounds with a Czalkyl moiety, and reduced in compounds with a Cz+2 alkyl moiety; and a fraction enriched in compounds with a Cz+2 alkyl moiety. 10

[0069] Advantageously, the process for the preparation may comprise separating the components of the polydisperse polyethyleneoxide alkyl ether according to the formula (I) by the chain length of the alkyl moiety, and removing compounds wherein R1represents an alkyl group comprising 14 carbon atoms, n represents an average number of from 10 to 16, to obtain a composition enriched in compounds with a C12 alkyl moiety, and reduced in compounds with a C14 alkyl moiety; and a fraction enriched in compounds with a C14 alkyl moiety.

[0070] Preferably, the process comprises: a) providing a polydisperse mixture of fatty alcohols according to the formula (II):

[0071] R1-OH (II), wherein R1represents an alkyl group comprising z or z+2 carbon atoms, wherein z is 12, 14, 16 or 18; and b) separating the fatty alcohols into a first fraction enriched in compounds with a Czalkyl moiety, and a second fraction enriched in a Cz+2 alkyl moiety; and c) reacting the first fraction with ethylene oxide under suitable conditions, to obtain a composition according to the disclosure. Alternatively, the process may begin with a Czalcohol only comprising traces of other alcohols, which is then converted to the subject composition.

[0072] More preferably, the process comprises: a) providing a polydisperse mixture of fatty alcohols according to the formula (II):

[0073] R1-OH (II), wherein R1represents an alkyl group comprising 12 or 14 carbon atoms, and b) separating the fatty alcohols into a first fraction enriched in compounds with a C12 alkyl moiety, and a second fraction enriched in a C14 alkyl moiety; and c) reacting the first fraction with ethylene oxide under suitable conditions, to obtain a composition according to the disclosure. Alternatively, the process may begin with a C12 alcohol only comprising traces of other alcohols, which is then converted to the subject composition.

[0074] Advantageously, the process for the preparation of a composition comprises separation by z carbon atoms of the polyethyleneoxide alkyl ethers according to the formula (I).

[0075] The compounds as defined in any one of embodiments according to the invention are preferably used for pest control at rates of 1 to 500 g / ha, preferably 50 to 300 g / ha.

[0076] The compounds as defined in any one of embodiments according to the invention are suitable for use on any plant, including those that have been genetically modified to be resistant to 11 active ingredients such as herbicides, or to produce biologically active compounds that control infestation by plant pests.

[0077] Generally, a compound as defined in any one of embodiments according to the invention is used in the form of a composition (e.g., formulation) containing a carrier. A compound as defined in any one of embodiments according to the invention and compositions thereof can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ulv) liquid, ultra low volume (ulv) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder.

[0078] Compositions of this invention, including all of the above disclosed embodiments and preferred examples thereof, can be mixed with one or more further pesticides including further fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.

[0079] A formulation typically comprises a liquid or solid carrier and optionally one or more customary formulation auxiliaries, which may be solid or liquid auxiliaries, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactant, binders and / or tackifiers. The composition may also further comprise a fertilizer, a micronutrient donor or other preparations which influence the growth of plants as well as comprising a combination containing the compound of the invention with one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides.

[0080] The compositions are prepared in a manner known per se, in the absence of auxiliaries for example by grinding, screening and / or compressing a solid compound of the present invention 12 and in the presence of at least one auxiliary for example by intimately mixing and / or grinding the compound of the present invention with the auxiliary (auxiliaries). In the case of solid compounds of the invention, the grinding / milling of the compounds is to ensure specific particle size.

[0081] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric substances, which comprise - at least - a compound of formula (I) as defined herein and the type of composition is to be selected to suit the intended aims and the prevailing circumstances.

[0082] The compositions may comprise 0.1 to 99 %, especially 0.1 to 95 %, of a compound (b), and 1 to 99.9 %, especially 5 to 99.9 %, of at least one solid or liquid carrier, it being possible as a rule for 0 to 25 %, especially 0.1 to 20%, of the composition to be surfactants (% in each case meaning percent by weight). Whereas concentrated compositions tend to be preferred for commercial goods, the end consumer as a rule uses dilute compositions which have substantially lower concentrations of active ingredient.

[0083] Besides a synergistic action with respect to eye irritation, the compositions according to the invention can also have further surprising advantageous properties. Examples of such advantageous properties that may be mentioned are: more advantageous degradability; improved toxicological and / or ecotoxicological behaviour; or improved characteristics of the useful plants including: emergence, crop yields, more developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf colour, less fertilizers needed, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigour, and early germination.

[0084] Some compositions according to the invention have a systemic action and can be used as foliar, soil and seed treatment pesticides.

[0085] The amount of a composition according to the invention to be applied, will depend on various factors, such as the compounds employed; the subject of the treatment, such as, for example plants, soil or seeds; the type of treatment, such as, for example spraying, dusting or seed 13 dressing; the purpose of the treatment, such as, for example prophylactic or therapeutic; the type of pest to be controlled or the application time.

[0086] In agricultural practice the application rates of the compositions according to the invention depend on the type of effect desired, and typically range from 20 to 4000 g of total composition per hectare.

[0087] When the compositions according to the invention are used for treating seed, rates of 0.001 to 50 g of a compound of component (b) per kg of seed, preferably from 0.01 to 10g per kg of seed.

[0088] Examples of foliar formulation types for pre-mix compositions are:

[0089] GR: Granules

[0090] WP: wettable powders

[0091] WG: water dispersible granules

[0092] SG: water soluble granules

[0093] SL: soluble concentrates

[0094] EC: emulsifiable concentrate

[0095] EW: emulsions, oil in water

[0096] ME: micro-emulsion

[0097] SC: aqueous suspension concentrate

[0098] CS: aqueous capsule suspension

[0099] OD: oil-based suspension concentrate, and

[0100] SE: aqueous suspo-emulsion.

[0101] Examples of seed treatment formulation types for pre-mix compositions are:

[0102] WS: wettable powders for seed treatment slurry

[0103] LS: solution for seed treatment

[0104] ES: emulsions for seed treatment

[0105] FS: suspension concentrate for seed treatment

[0106] WG: water dispersible granules, and

[0107] CS: aqueous capsule suspension.

[0108] Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts. As with the nature of the formulations, the methods of application, such as foliar, drench, spraying, atomizing, dusting, scattering, 14 coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.

[0109] The tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries.

[0110] Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily employed in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

[0111] Generally, a tank-mix formulation for foliar or soil application comprises 0.1 to 20%, especially 0.1 to 15 %, of the desired ingredients, and 99.9 to 80 %, especially 99.9 to 85 %, of a solid or liquid auxiliaries (including, for example, a diluent or solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 20 %, especially 0.1 to 15 %, based on the tank-mix formulation.

[0112] Typically, a pre-mix formulation for foliar application comprises 0.1 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.9 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.

[0113] Normally, a tank-mix formulation for seed treatment application comprises 0.25 to 80%, especially 1 to 75 %, of the desired ingredients, and 99.75 to 20 %, especially 99 to 25 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40 %, especially 0.5 to 30 %, based on the tank-mix formulation.

[0114] Typically, a pre-mix formulation for seed treatment application comprises 0.5 to 99.9 %, especially 1 to 95 %, of the desired ingredients, and 99.5 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation. 15

[0115] Whereas commercial products will preferably be formulated as concentrates (e.g., pre-mix composition (formulation)), the end user will normally employ dilute formulations (e.g., tank mix composition).

[0116] Preferred seed treatment pre-mix formulations are aqueous suspension concentrates. The formulation can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful. The seeds may be presized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art. The compounds of the present invention are particularly suited for use in soil and seed treatment applications. In general, the pre-mix compositions of the invention contain 0.5 to 99.9 especially 1 to 95, advantageously 1 to 50 % by mass of the desired ingredients, and 99.5 to 0.1 , especially 99 to 5 % by mass of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries (or adjuvant) can be a surfactant in an amount of 0 to 50, especially 0.5 to 40 % by mass based on the mass of the pre-mix formulation.

[0117] In addition, further, other biocidally active ingredients or compositions may be combined with the compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compositions of the invention. When applied simultaneously, these further active ingredients may be formulated together with the compositions of the invention or mixed in, for example, the spray tank. These further biocidally active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0118] In addition, the compositions of the invention may also be applied with one or more systemically acquired resistance inducers (“SAR” inducer). SAR inducers are known and described in, for example, United States Patent No. US6, 919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.

[0119] The compositions as defined in any one of embodiments according to the invention are normally used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g. fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of 16 these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.

[0120] The plants and I or target crops in accordance with the invention include conventional as well as genetically enhanced or engineered varieties such as, for example, insect resistant (e.g. Bt. and VIP varieties) as well as disease resistant, herbicide tolerant (e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®) and nematode tolerant varieties. By way of example, suitable genetically enhanced or engineered crop varieties include the Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.

[0121] The term "plants" and / or “target crops” is to be understood as including also plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola). Examples of crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.

[0122] The term "plants" and / or “target crops” is to be understood as including those which naturally are or have been rendered resistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesizing one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include 5-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonizing nematodes, and toxins produced by scorpions, arachnids, wasps, and fungi. An example of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut® (Syngenta Seeds). An example of a crop comprising more than one gene that codes for insecticidal resistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds). Crops or seed material thereof can also be resistant to multiple types of pests (so-called stacked transgenic events when created by genetic modification). For example, a plant can have the ability to express 17 an insecticidal protein while at the same time being herbicide tolerant, for example Herculex I ® (Dow AgroSciences, Pioneer Hi-Bred International).

[0123] The term "plants" and / or “target crops” is to be understood as also including plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0392225). Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95 / 33818, and EP-A-0 353 191. The methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

[0124] Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as 5-endotoxins, e.g. CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1 , Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosomeinactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl- transferase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

[0125] Further, in the context of the present invention there are to be understood by 5-endotoxins, for example CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02 / 15701). Truncated toxins, for example a truncated CrylAb, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted 18 into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3A toxin (see W003 / 018810).

[0126] More examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0374 753, WO93 / 07278, WO95 / 34656, EP-A-0427 529, EP- A-451 878 and W003 / 052073.

[0127] The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cryl- type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90 / 13651.

[0128] The toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).

[0129] Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylAb toxin); YieldGard Rootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus® (maize variety that expresses a CrylAb and a Cry3Bb1 toxin); Starlink® (maize variety that expresses a Cry9C toxin); Herculex I® (maize variety that expresses a Cry1 Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylAc toxin); Bollgard I® (cotton variety that expresses a CrylAc toxin); Bollgard II® (cotton variety that expresses a CrylAc and a Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and a CrylAb toxin); NewLeaf® (potato variety that expresses a Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

[0130] Further examples of such transgenic crops are:

[0131] 1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylAb toxin. Bt11 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium. 19

[0132] 2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonag rioides) by transgenic expression of a CrylAb toxin. Bt176 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

[0133] 3. MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03 / 018810.

[0134] 4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.

[0135] 5. 1 PC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0136] 6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize for the expression of the protein Cry1 F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.

[0137] 7. NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.

[0138] The term “locus” as used herein means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.

[0139] The term “plants” refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.

[0140] The term “plant propagation material” is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, 20 such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion. Preferably “plant propagation material” is understood to denote seeds.

[0141] Pesticidal agents referred to herein using their common name are known, for example, from "The Pesticide Manual", 15thEd., British Crop Protection Council 2009.

[0142] The compounds as defined in any one of embodiments according to the invention for use in the inventive methods may be the sole active ingredient of a composition or it may be admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate. An additional active ingredient may, in some cases, result in unexpected synergistic activities.

[0143] The compositions according to the invention can also comprise further solid or liquid auxiliaries, such as stabilizers, for example unepoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and / or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0144] Another aspect of the invention is related to the use of a compound as defined in any one of embodiments according to the invention, of a composition comprising at least one compound as defined in, or of a fungicidal or insecticidal mixture comprising at least one compound as defined in any one of embodiments according to the invention, in admixture with other fungicides or insecticides as described above, for controlling or preventing infestation of plants, e.g. plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living material by insects or by phytopathogenic microorganisms.

[0145] A further aspect of invention is related to a method of controlling or preventing an infestation of plants, e.g. plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g. harvested food crops, or of non-living materials by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, which comprises the application of a compound as defined in any one of embodiments according to 21 the invention as active ingredient to the plants, to parts of the plants or to the locus thereof, to the propagation material thereof, or to any part of the non-living materials.

[0146] Controlling or preventing means reducing infestation by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated.

[0147] When a composition according to the disclosure is used, the application rates for the active ingredient(s) in the method according to the invention are as described above, e.g., typical are rates of 5 to 2000 g a.i. / ha, particularly 10 to 1000 g a.i. / ha, e.g. 50, 75, 100 or 200 g a.i. / ha. The compositions can be applied to the plants once or more than once during a growing season.

[0148] For use in the method according to the invention, the composition can be converted into the customary formulations described above, e.g., solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form will depend on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compound of formula (I).

[0149] The term "plant" as used herein includes seedlings, bushes and crops of fruits and vegetables.

[0150] Examples

[0151] The following, non-limiting examples illustrate examples for compositions according to the present disclosure.

[0152] Example 1 : A composition of a commercially available polyoxyethylene lauryl ether surfactant was analysed and found to contain two main fractions with alkyl chain lengths of C = 12 and of C = 14, further referred to as Ci2Enand Ci4En.

[0153] Applicants separated the composition into two fractions as Ci2Enand Ci4En, wherein n is from 15-22, respectively, equalling of from 15 to 22 ethylene oxide units on average per molecule.

[0154] The cytotoxicity of Ci2Enand Ci4Ento human corneal epithelium cells was determined, by testing cell viability against concentration for commercial Polyoxyethylene lauryl ether, Ci2Enand Ci4En(Table 1). The lethal dose (LD50) values for the polydisperse Polyoxyethylene lauryl ether mixture and of the isolated Ci4Enwere found to be in the same range of 0.02 to 0.04 22 mM, respectively, whereas Ci2Enrequired double the amount to achieve the same LD50 value, with a range of from 0.04 to 0.08 mM.

[0155] This demonstrates that Ci2Enhas a reduced cytotoxicity in the model on human corneal epithelium cells as compared to the commercial polydisperse polyoxyethylene lauryl ether, comprising mixture of C12 and C14 components.

[0156] Table 1 : cell viability against concentration was measured for unpurified commercial Polydisperse Polyoxyethylene lauryl ethylene oxide ether, Ci2Enand Ci4En.

[0157] Example 2: The adjuvancy performance of compositions comprising Nicosulfuron in two different concentrations was determined by visual observation of phytotoxicity on three different weed species in a greenhouse at different active ingredient rates (Table 2). The compositions tested were a composition without adjuvant; a composition comprising the unpurified industrial grade polydisperse Polyoxyethylene lauryl ethylene oxide ether, a composition comprising isolated and C12En, and a composition comprising isolated and C14Enas adjuvants.

[0158] All materials tested increased the phytotoxicity in comparison to the composition that contained no adjuvant, indicating that all three provide an adjuvancy effect. Furthermore, there was no observable difference in visual injury between the treatments.

[0159] Table 2: Mean visual injury of weeds against unpurified Brij-35, C12Enand C14Enat different active ingredient rates. 23

[0160] In other words, the inclusion of the C14Enfraction in the unpurified commercial polydisperse polyoxyethylene lauryl ethylene oxide ether gave no or no statistically significant biological performance benefit, but surprisingly increased ocular irritancy. Removing this fraction allowed the applicants to reduce the irritancy while maintaining its primary technical feature as an adjuvant.

[0161] While the invention has been described in connection with certain embodiments, it will be understood that modifications and variations are possible without departing from the scope of the appended claims.

[0162] The invention is defined by the claims.

Claims

24Claims1 . A composition comprising a polyethyleneoxide alkyl ether according to the formula (I):R1-O-(CH2CH2O)n-H (I), wherein R1represents an alkyl group comprising z or z+2 carbon atoms, wherein z is 12, 14, 16 or 18; wherein the weight ratio of compounds of formula (I) comprising a Czalkyl moiety to compounds of formula (I) comprising a Cz+2 alkyl moiety is in the range of 95:5 to 100:0; and wherein n represents an average number of from 6 to 22.

2. The composition according to claim 1 , wherein the weight ratio of compounds of formula (I) comprising a Czalkyl moiety to compounds of formula (I) comprising a Cz+2alkyl moiety is in the range of 98:2 to 99.9:0.1 .

3. The composition according to claim 1 or claim 2, further comprising the polyethyleneoxide alkyl ether according to the formula (I) as component (a): agrochemically active ingredient (b), wherein (b) is present in an agrochemically active amount.

4. The composition according to claim 3, wherein the agrochemically active ingredient is selected from pesticides, herbicides, fungicides, and plant growth regulators, and mixtures thereof.

5. The composition according to claim 3 or claim 4, wherein the weight / weight ratio of component (a) to component (b) is in the range of from 1 :3 to 1 :100.

6. The composition according to any one of claims 3 to 5, wherein the composition comprises a herbicide; more preferably wherein the composition comprises nicosulfuron.

7. The composition according to any preceding claim, wherein the polyethyleneoxide alkyl ether is present in an amount ranging from 0.1% to 10% by weight of the composition.

8. The composition according to any preceding claim, further comprising additional adjuvants, stabilizers, or inert ingredients commonly used in agrochemical formulations.

9. A method for preparing an agricultural composition with reduced eye irritancy, comprising:25 i.) providing an agrochemically active ingredient (b); and ii.) contacting the active ingredient with a polyethyleneoxide alkyl ether according to claim 1 or claim 2.

10. Use of a polyethyleneoxide alkyl ether composition according to claim 1 or claim 2, as a co-formulant in an agrochemical composition comprising at least one agrochemically active ingredient.11 . A process for the reducing the eye irritancy of a polydisperse polyethyleneoxide alkyl ether according to the formula (I):R1-O-(CH2CH2O)n-H (I), wherein R1represents an alkyl group comprising z or z+2 carbon atoms, wherein z is 12, 14, 16 or 18, wherein n represents an average number of from 6 to 22, by enriching the content of compounds of formula (I) comprising a Czalkyl moiety.

12. The process according to claim 11 , comprising separating the components of the polydisperse polyethyleneoxide alkyl ether according to the formula (I) by the chain length of the alkyl moiety, and removing compounds wherein R1represents an alkyl group comprising z+2 carbon atoms, n represents an average number of from 6 to 22, to obtain a composition enriched in compounds with a Czalkyl moiety, and reduced in compounds with a Cz+2alkyl moiety; and a fraction enriched in compounds with a Cz+2alkyl moiety.

13. A process for the preparation of a composition according to any one of claims 1 to 8, comprising: a) providing a polydisperse mixture of fatty alcohols according to the formula (II):R1-OH (II), wherein R1represents an alkyl group comprising z or z+2 carbon atoms; wherein z is 12, 14, 16 or 18; and b) separating the fatty alcohols into a first fraction enriched in compounds with a Czalkyl moiety, and a second fraction enriched in a Cz+2alkyl moiety; and c) reacting the first fraction with ethylene oxide under suitable conditions, to obtain a composition according to any one of claims 1 to 8.

14. A process for the preparation of a composition according to any one of claims 1 to 8, comprising the separation by z carbon atoms of the polyethyleneoxide alkyl ethers according to the formula (I).

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