GB2614084A

GB2614084A - Pesticide emulsifiable concentrate and use thereof

Info

Publication number: GB2614084A
Application number: GB2118726.5A
Authority: GB
Inventors: Timothy Bristow James
Original assignee: Rotam Agrochem International Co Ltd
Current assignee: Rotam Agrochem International Co Ltd
Priority date: 2021-12-22
Filing date: 2021-12-22
Publication date: 2023-06-28

Abstract

A pesticidal emulsifiable concentrate (EC) composition comprising a water-insoluble pesticide, an amide of general formula (I) and a lactamide of general formula (II) wherein n is an integer from 3-15 and each of R1 and R2 is independently a C1-C4 alkyl group. The pesticide may be a microbiocide, herbicide or insecticide (e.g. prothioconazole). Preferably, the pesticide is present at 0.1 – 60 % by weight of the composition. The amide (I) may account for 5 – 70 wt.% of the composition. The lactamide (II) may be 0.3 – 50 % w/w of the EC. Most preferably, both R1 and R2 are methyl. Preferably, the EC comprises less than 1 weight% water. The EC may be mixed with water to form an emulsion wherein the weight ratio of water to EC is from 1:1 to 1000:1. Also claimed is a method of preparing the EC, and a method of preventing pathogenic fungal infection comprising use of the EC described herein.

Description

Intellectual Property Office Application No GI321187265 RTM Date:6 May 2022 The following terms are registered trade marks and should be read as such wherever they occur in this document: Solvesso Mastersizer Intellectual Property Office is an operating name of the Patent Office www.gov.uk /ipo

PESTICIDE EMULSIFIABLE CONCENTRATE AND USE THEREOF

The present invention relates to an emulsifiable concentrate (EC) formulation comprising a pesticide, in particular a water-insoluble pesticide. The present invention further relates to a method for preparing the formulation. The present invention further relates to a method for preventing and controlling pathogenic fungi of a plant and/or undesired plant growth and/or undesired insect or mite infestation and/or for regulating plant growth using the EC formulation Emulsifiable concentrates (also called 'EC') are formulations widely used in crop protection. In general EC formulations are used to formulate water-insoluble pesticidally active components and comprising a solution of the active component in an organic solvent that is immiscible with water. Upon dilution with water, for example to apply to plants to be treated or their locus, the EC formulation forms an oil-in-water emulsion.

It is known that emulsifiable concentrates have a number of technical problems associated with the formulation. First, emulsifiable concentrate formulations exhibit poor stability, with a significant tendency of the components to crystallize. The crystallization of the active components in the emulsifiable concentrate is particularly apparent under low temperature conditions, especially in extremely low temperature environments. In addition, it is known that emulsifiable concentrates can exhibit a poor emulsion effect, that is the ease of forming an emulsion, and an unfavourable dilution stability.

In order to allow the emulsifiable concentrate to achieve an adequate performance, agricultural formulators are usually forced to compromise on the properties of the formulation. For example, in order to overcome the problem of the stability of the emulsifiable concentrate under extremely low temperature conditions, agricultural formulators inevitably reduce the ease with which the formulation forms an emulsion when diluted with water and the ability of the emulsion to resist crystallisation of components when diluted with water There is therefore a need for an improved emulsifiable concentrate formulation for pesticidally active components. In particular, it would be advantageous if the formulation could provide both a high stability under low temperature conditions, while at the same time be easy to emulsify upon dilution with water and exhibit stability under dilute aqueous conditions.

It has now been found that an improved emulsifiable concentrate (EC) formulation for pesticidally active components can be achieved using an amide system comprising an amide of general formula (I) as defined hereinbelow and a lactamide of general formula (II) as defined hereinbelow.

Zo According to a first aspect of the present invention, there is provided a pesticidal emusifiable concentrate (EC) composition comprising: a) a water-insoluble pesticide; b) an amide of general formula (0: ( I) wherein n is an integer from 3 to 15; and c) a lactamide of general formula (II): CH3 -CH(OH) -C(0) -N -R1 R2 wherein each of R1 and R2 is independently selected from a Ci to Ca alkyl group.

The emulsifiable concentrate (EC) composition comprises a water-insoluble pesticide. The present invention is suitable for formulating one or a combination s of two or more water-insoluble pesticides.

The term 'pesticide' refers to at least one active substance selected from a fungicide, an insecticide, a nematicide, an herbicide, a safener, a biological pesticide and/or a growth regulator. Preferred pesticides are a fungicide, an insecticide, an herbicide and a growth regulator. More preferred pesticides are fungicides.

Suitable pesticidally active compounds for use in the composition are known in the art and many are commercially available. Details of suitable pesticidally active compounds can be found, for example, in the Pesticide Manual, Edition 16 (2013), The BritishCrop Protection Council, London.

The one or more pesticides may be selected from a microbiocide. Suitable microbicides are, for example, methoxyacrylate microbicides, such as azoxystrobin, couoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, fenoxystrobin/flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, and trifloxystrobin; triazole microbicides, such as azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, mefentrifluconazole, and ipfentrifluconazole; carboxamide microbicides, such as benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, and penthiopyrad; phenylamide or acyl amino acid microbicides, such as benalaxyl, benalaxyl-M, metalaxyl, metalaxyl-M (mefenoxam), ofurace, and oxadixyl; benzimidazole microbicides, such as benomyl, carbendazim, fuberidazole, thiabendazole, and thiophanate-methyl; anilinopyrimidine microbicides, such as cyprodinil, mepanipyrim, and pyrimethanil; and thiocarbamate microbicides, such as ferbam, mancozeb, maneb, metam, metiram, propineb, thiram, zineb, and ziram.

The one or more pesticides may be selected from a herbicide. Suitable herbicides are, for example, acetamide herbicides, such as acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, and thenylchlor; amino acid derivative herbicides, such as bilanafos, glyphosate, glufosinate, and sulfosate; aryloxyphenoxypropionate herbicides, such as clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, and quizalofop-P-tefuryl; cyclohexanedione herbicides, such as butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, and tralkoxydim; dinitroaniline herbicides, such as benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, and trifluralin; diphenyl ether herbicides, such as acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, and oyfluorfen; triazine herbicides, such as ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, and triaziflam; pyridine herbicides, such as aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, and thiazopyr; sulfonylurea herbicides, such as amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metazosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, and tritosulfuron; urea herbicides, such as chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, and tebuthiuron; and other herbicides, such as amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, benzofenap, bentazone, benzobicyclon, bicyclopyrone, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethyl, chlorthal, cinmethylin, clomazone, cumyluron, cyprosulfam ide, dicamba, difenzoquat, diflufenzopyr, Drechsleramonoceras, endothal, ethofumesate, etobenzanid, fenoxasulfone, fentrazam ide, flumiclorac-pentyl, flumioxazin, flupoxam, flurochloridone, flurtamone, indanofan, isoxaben, isoxaflutole, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methylarsonicacid, naptalam, oxadiargyl, oxadiazon, oxaziclomefone, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazoxyfen, pyrazolynate, quinoclamine, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, and topramezone.

The one or more pesticides may be selected from an insecticide. Suitable insecticides are, for example, organic phosphorus insecticides, such as chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos-methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, and trichlorfon; carbamate insecticides, such as alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, and triazamate; synthetic pyrethrin insecticides, such as allethrin, bifenthrin, cyfluthrin, (RS)cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, betacypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and pyrethrin II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, and dimefluthrin; insect growth regulator insecticides, such as a) chitin synthetic inhibitors, for example chlorfluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, and triflumuron; and buprofezin, diofenolan, hexythiazox, etoxazole, and clofentazine; b) ecdysone antagonists, for example halofenozide, methoxyfenozide, tebufenozide, and azadirachtin; c) juvenile hormone analogues, for example pyriproxyfen, methoprene, and fenoxycarb; and d) lipoid biosynthesis inhibitors, for example spirodiclofen, spiromesifen, and spirotetramat; nicotinic receptor agonist/antagonist compounds, such as clothianidin, dinotefuran, flupyradifurone, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, and thiacloprid; macrolide insecticides, such as abamectin, emamectin, milbemectin, spinosad, and spinetoram; and other insecticides, such as chloranthraniliprole, cyantraniliprole, flubendiamide, fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim, bifenazate, cartap, flonicamid, pyridalyl, and pymetrozine.

In a particular embodiment, the one or more pesticides are preferably selected from triazole pesticides, for example azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, mefentrifluconazole, and ipfentrifluconazole; methoxyacrylate pesticides, for example azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, fenoxystrobin/flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, and trifloxystrobin; and carboxamide pesticides, for example boscalid, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, and penthiopyrad.

The one or more pesticides employed in the present invention are water-insoluble. Generally, the pesticide can be dissolved in water at 25°C at a concentration of not more than 1 g/L, preferably not more than 200 mg/L, and especially not more than 50 mg/L.

The pesticides employed in the present invention may have any suitable melting point. Preferably, the pesticide has a melting point of greater than 40°C, more preferably greater than 50°C, more preferably still greater than 60°C, still more preferably greater than 70°C, and especially greater than 80°C, more especially greater than 90°C.

The pesticide is preferably present in the concentrate in a dissolved form.

In addition to the water-insoluble pesticide, the concentrate may comprise one or more other pesticides. More preferably, the pesticides present in the composition are all water-insoluble, as hereinbefore defined.

The one or more pesticides may be present in the composition in any suitable amount. Based on the sum of all pesticides present in the concentrate composition, the composition may comprise from 0.1% by weight, preferably from 0.25%, more preferably from 0.5%, still more preferably from 0.6%, more preferably still from 0.7%, especially from 0.8%, more especially from 0.9%, still more especially from 1% by weight. Based on the sum of all pesticides present in the concentrate composition, the composition may comprise up to 60% by weight, preferably up to 55%, more preferably up to 50%, still more preferably up to 45%, more preferably still up to 40%, especially up to 35%, more especially up to 30% by weight. The composition may comprise from 0.1 to 60% by weight, preferably from 1% to 40% by weight, and especially from 5% to 30% by weight of the one or more pesticides.

The composition of the present invention further comprises an amide of general formula (I): ( I) wherein n is an integer from 3 to 15.

Preferably, the amides of formula (I) are those in which n is an integer from 3 to 14, more preferably from 3 to 12, still more preferably from 3 to 11. Preferably, the amides of formula (I) are those in which n is an integer from 4 to 13, more preferably from 4 to 12, still more preferably from 4 to 11. Preferred amides of formula (I) are those in which n is an integer from 5 to 12, more preferably from 5 to 11, still more preferably from 5 to 10, more preferably still from 5 to 9, that is 5, 6, 7, 8 or 9. In particular, the amides of formula (I) are preferably those in which n is 5, 7 or 9.

The composition may comprise a single amide of the general formula (I) or a mixture of two or more amines of formula (I). In one embodiment, the composition comprises a mixture of the amides of formula (I), preferably a mixture of two or more amides in which n is from 5 to 9, for example the mixture of the amides of formula (I) in which n is 5 and 7.

The amide of formula (I) may be present in any suitable amount. The concentrate may comprise up to 70% by weight, preferably not more than 60% by weight, and especially not more than 50% by weight of the amide of formula (I). The concentrate may comprise at least 5% by weight, preferably at least 10% by weight, and especially at least 15% by weight of the amide of formula (I). The composition may comprise from 5 to 70% by weight, especially from 10 to 60% by weight, and more particularly from 15 to 50% by weight of the amide of formula (I).

The composition of the present invention further comprises a lactamide of general formula (II): CH3 -CH(OH) -C(0) -N -R1 R2 wherein each of R1 and R2 is independently selected from a Ci to C4 alkyl group.

Each of R1 and R2 are preferably selected from Ci to Cs alkyl groups, more preferably from Ci or C2 alkyl groups.

R1 and R2 may be the same or different. In one preferred embodiment, R1 and R2 are the same.

In the case where R1 and/or R2 is propyl or butyl, these alkyl groups may be linear or branched, for example, isopropyl or tert-butyl.

Preferably, the lactamides of formula (II) are those in which both R1 and R2 are methyl.

The composition may comprise up to 50% by weight, preferably up to 30% by weight, and especially up to 20% by weight of the lactamide of formula (II). The composition may comprise at least 0.5% by weight, preferably at least 1% by weight, and especially at least 3% by weight of the lactamide of formula (II). The composition may comprise from 0.3 to 50% by weight, especially from 1 to 30% by weight, and more particularly from 3 to 20% by weight of the lactamide of formula (II).

The amide of general formula (I) and the lactamide of general formula (II) may be present in the same amounts by weight or in different amounts by weight. Preferably, the amide of general formula (I) is present in a greater amount by weight than the lactamide of general formula (II).

The weight ratio of the amide of formula (I) to the lactamide of formula (II) present in the composition may be from 1:1 to 20:1, preferably from 2:1 to 15: 1, more preferably 3:1 to 13:1, still more preferably from 4:1 to 12:1, and especially from 5:1 to 10:1.

Preferably, the composition comprises substantially no water or is free of water.

More preferably, the composition comprises not more than 1% by weight of water, still more preferably not more than 0.5% by weight of water, and especially not more than 0.3% by weight of water. The water-content of the composition may be no more than 0.2% by weight, more preferably no more than 0.1% by weight.

The amide of formula (I) and the lactamide of formula (II) function as solvents for the active pesticide components. In addition to the amide of formula (I) and the lactamide of formula (II), the composition may comprise one or more other solvents, such as hydrocarbon solvents and plant-derived solvents.

s Suitable hydrocarbon solvents are known in the art and include aliphatic hydrocarbons and aromatic hydrocarbons. The hydrocarbon solvents preferably have a water solubility of not more than 5% by weight, preferably not more than 1% by weight, and especially not more than 0.1% by weight at 20°C.

In many embodiments, the hydrocarbon solvents have a boiling point of at least 100°C, preferably at least 150°C, and especially at least 180°C under normal atmospheric conditions.

The hydrocarbon solvents may comprise only carbon and hydrogen atoms.

The hydrocarbon solvents are preferably hydrocarbons having at least 6 carbon atoms, more preferably at least 7 carbon atoms, still more preferably at least 8 carbon atoms. The hydrocarbon solvents may be hydrocarbons having up to 20 carbon atoms, more preferably up to 18 carbon atoms, still more preferably up to 16 carbon atoms. Preferred hydrocarbon solvents are Co to C20 hydrocarbons, more especially Ca to Cm hydrocarbons.

Preferred hydrocarbon solvents are aromatic hydrocarbon solvents. In addition to at least one aromatic hydrocarbon unit, the aromatic hydrocarbon may comprise an aliphatic hydrocarbon substituent.

Suitable aromatic hydrocarbons include unsubstituted aromatic hydrocarbons and alkyl-substituted aromatic compounds, for example, toluene, xylene, ethylbenzene and benzenes with a long chain alkyl group, such as C9 to C10 dialkyl and trialkyl benzenes, for example the commercial products Solvesso 100 from Exxon Mobil Europe or Aromatic 100 from Exxon Mobil USA, Cm to Cu alkylbenzenes, for example the commercial products Solvesso 150 from Exxon Mobil Europe or Aromatic 150 from Exxon Mobil USA, and alkyl naphthalenes, for example the commercial products Solvesso 200 from Exxon Mobil Europe or Aromatic 200 from Exxon Mobil USA. A mixture of two or more of the above-mentioned aromatic compounds may also be used.

Preferably, the aromatic hydrocarbon comprises not more than 5% by weight, s more preferably not more than 2% by weight, and especially not more than 1% by weight of naphthalene based on the total weight of the aromatic solvent. Such solvents having a naphthalene content of not more than 1% by weight are commercially available, for example, the solvents marketed under the name ND (Naphthalene Depleted) from Exxon Mobil Europe, such as 150ND and 200ND.

Such solvents having a naphthalene content of not more than 0.1% by weight or even lower are present in the products Aromatic 15OULN and Aromatic 200ULN available from Exxon Mobil USA.

Suitable plant-derived solvents include vegetable oils and substituted derivatives thereof, such as methyl oleate, epoxy soybean oil, methylated soybean oil, rosin-based vegetable oil, castor oil, coconut fatty acid methyl ester, methyl laurate, and methyl caprate.

The composition may comprise the further solvent in an amount of up to 50% by weight, preferably up to 45%, more preferably up to 40% by weight, still more preferably up to 35%, more especially still up to 30%, especially up to 25%, more especially up to 20% by weight. If one or more further solvents are employed, the composition may comprise the further solvents in an amount of at least 0.1% by weight, preferably at least 0.5%, more preferably at least 1% by weight, still more preferably at least 2%, more preferably still at least 3% by weight, especially at least 4%, more especially at least 5% by weight.

The total amount of solvent present in the composition may be up to 90% by weight, preferably up to 85% by weight, more preferably up to 80%, still more preferably up to 75%, more preferably still up to 70% by weight. The total amount of solvent present in the composition may be from 5% by weight, preferably from 10% by weight, more preferably from 15%, still more preferably from 20%, more preferably still from 25%, especially from 30% by weight.

In one embodiment, the composition may comprise from 10 to 60% by weight of an amide of formula (I), for example an amide in which n is 7, from 1 to 30% by s weight of a lactamide of formula (I), for example a lactamide in which both R1 and R2 are both methyl, and optionally from 1 to 20% by weight of hydrocarbon solvent, wherein the total amounts of these components add up to from 12 to 90% by weight of the composition, preferably from 20 to 80% by weight, and more preferably from 30 to 70% by weight.

Zo In addition, the composition may comprise one or more auxiliary agents commonly used in crop protection products. Suitable auxiliary agents include liquid carriers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetrants, protective colloids, adhesives, thickening agents, microbicides, antifreezing agents, antifoaming agents, colorants, tackifiers and binders.

Suitable liquid carriers are organic solvents, such as oils of plant or animal origin; alcohols, such as ethanol, propanol, butanol, and cyclohexanol; diols; ketones; esters; and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetrants, protective colloids or adjuvants. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International or North American version).

Suitable anionic surfactants include alkali metals, alkaline earth metals or ammonium salts of sulfonic acid, sulfuric acid, phosphoric acid, and carboxylic acid, and mixtures thereof. Examples of sulfonates are alkyl aryl sulphonates, diphenyl sulfonates, a-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed napthalenes, sulfonates of dodecyl-and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulphosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, sulfates of ethoxylated alkylphenols, sulfates of alcohols, sulfates of ethoxylated alcohols or sulfates of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates. Preferred anionic surfactants are sulfates and sulfonates.

Suitable nonionic surfactants include alkoxylates, N-substituted fatty acid amides, amine oxides, esters, glycosyl surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucam ides or fatty acid alkanolam ides. Examples of esters are fatty acid esters, glycerides or monoglycerides. Examples of glycosyl surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol or vinyl acetate. Preferred nonionic surfactants are alkoxylates. Nonionic surfactants such as alkoxylates can also be used as adjuvants.

Suitable cationic surfactants include quaternary-type surfactants, such as quaternary ammonium compounds having 1 or 2 hydrophobic groups, or salts of long-chain primary amines.

Suitable amphoteric surfactants include alkyl betaines and imidazolines.

The composition preferably comprises at least one anionic surfactant. The composition may comprise not less than 0.03% by weight, preferably not less than 0.1% by weight, and especially not less than 0.5% by weight of anionic surfactants.

The composition may comprise up to 25% by weight, preferably up to 20%, more preferably up to 15%, still more preferably up to 10% by weight, and especially up to 5% by weight of anionic surfactants.

The composition preferably comprises at least one nonionic surfactant, for s example one or more alkoxylates. The composition may comprise from 1% by weight, preferably from 3%, more preferably from 5% by weight, and especially from 10% by weight of nonionic surfactants. The composition may comprise up 65% by weight, preferably up to 60%, more preferably up to 55%, still more preferably up to 50%, more preferably still up to 45% by weight, and especially up to 35% by weight of nonionic surfactants.

In a preferred embodiment, the composition preferably comprises at least one alkoxylate, especially an alkoxylated C6 to C22 alcohol. The composition may comprise at least 2% by weight, preferably at least 5%, more preferably at least 7% by weight, and especially at least 10% by weight of alkoxylates, especially an alkoxylated C6 to C22 alcohol.

Preferably, the composition comprises one or more nonionic surfactants, such as one or more alkoxylates, and one or more anionic surfactants, such as one or more sulfates or sulfonates.

Suitable block polymers include A-B or A-B-A type block polymers comprising blocks of polyoxyethylene and polyoxypropylene, or A-B-C type block polymers comprising alkanol, polyoxyethylene and polyoxypropylene.

Suitable polyelectrolytes include polyacids or polybases, preferably polyacids. Examples of polybases are polyvinylamines or polyethylene amines. Examples of polyacids are acrylic copolymers or AMPS (2-acrylamido-2-methylpropanesulfonic acid) copolymers. Preferably, the polyelectrolytes are copolymers comprising, in the polymerized form, amides containing at least one monomer selected from Nvinyllactam, N-Ci to C6 alkyl acrylamide and N,N-di Ci to C6 alkyl acrylamide; poly(C2 to 6 alkylene glycol) (meth)acrylate and/or mono Ci to 22 alkyl-terminated poly(C2 to 6 alkylene glycol) (meth)acrylate; Ci to Cs alkyl (meth)acrylate; and (meth)acrylic acid. More preferably, the polyelectrolytes are copolymers comprising, in the polymerized form, amides containing at least one monomer selected from N-vinyllactam; mono Ci to 22 alkyl-terminated poly(C2 to 6 alkylene glycol) (meth)acrylate; Ci to Ca alkyl (meth)acrylate; and (meth)acrylic acid. In another preferred form, the polyelectrolytes are copolymers comprising, in the polymerized form, from 25 to 85 wt% of amides containing at least one monomer selected from N-vinyllactam; from 1 to 40 wt% of mono Ci to 22 alkyl-terminated poly(C2 to 6 alkylene glycol) (meth)acrylate; from 5 to 50 wt% of Ci to Ca alkyl (meth)acrylate; and up to 15 wt% of (meth)acrylic acid, wherein the sum of the monomers equals 100%. In another preferred form, the polyelectrolytes are copolymers comprising, in the polymerized form, from 30 to 85 wt% of amides containing at least one monomer selected from N-vinyllactam; from 5 to 20 wt% of mono Ci to 22 alkyl-terminated poly(C2 to 6 alkylene glycol) (meth)acrylate; from 8 to 35 wt% of Ci to Ca alkyl (meth)acrylate; and from 0.5 to 10 wt% of (meth)acrylic acid, wherein the sum of the monomers equals 100%. In another preferred form, the polyelectrolytes are copolymers comprising in the polymerized form at least one ethylenically unsaturated monomer containing a sulfonic acid group, at least one monomer selected from Ci to C4 alkyl (meth)acrylate and at least one monomer selected from C6 to C22 alkyl (meth)acrylate. In another preferred form, the polyelectrolytes are copolymers comprising in the polymerized form from 5 to 50% by weight of at least one ethylenically unsaturated monomer containing a sulfonic acid group, from 20 to 70% by weight of at least one monomer selected from Ci to Ca alkyl (meth)acrylate and from 5 to 30% by weight of at least one monomer selected from C6 to C22 alkyl (meth)acrylate, based on the total weight of the monomer. The composition may comprise from 0.5 to 40% by weight, preferably from 2 to 30% by weight, and especially from 5 to 25% by weight of polyelectrolytes, for example polyacids such as acrylic copolymers or AMPS copolymers.

Suitable adjuvants are compounds that have negligible pesticide activity or no pesticide activity and improve the biological performance of the pesticide on a target object. Examples are surfactants, mineral oils or vegetable oils and other auxiliary agents. Other examples are listed by Knowles, 'Adjuvants and Additives', Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

Suitable m icrobiocides include isothiazolinone derivatives, such as alkylisothiazolinones and benzoisothiazolinones.

Suitable antifreezing agents include ethylene glycol, propylene glycol, urea and glycerol.

Suitable antifoaming agents include polysiloxanes, long-chain alcohols and fatty acid salts.

Suitable colorants, for example to colour the composition red, blue or green, include low water-soluble pigments and water-soluble dyes. Examples are inorganic colorants, such as iron oxide, titanium oxide, and iron hexacyanoferrate, and organic colorants, such as alizarin colorants, azo colorants, and phthalocyanine colorants.

In a further aspect, the present invention provides a method for preparing the emulsifiable concentrate composition of the present invention, the method comprising mixing: a water-insoluble pesticide; an amide of formula (I) as hereinbefore described; a lactamide of formula (II) as hereinbefore described; and optionally one or more auxiliary agents.

Furthermore, the present invention provides an emulsion composition that may be obtained by mixing the emulsifiable concentrate composition of the present invention with water The emulsion usually forms spontaneously during mixing. In most cases, the emulsion is an oil-in-water emulsion. The weight ratio of water to the emulsifiable concentrate composition may be varied, for example according to the required concentration of the pesticide component in the emulsion composition and may range from 1:1 to 1000:1, preferably from 3:1 to 200:1, for example 99:1.

As noted above, the emulsion usually forms spontaneously when the emulsifiable concentrate composition is combined with water. The resulting emulsion may have an average droplet size of the dispersed phase of greater than 0.1 pm, preferably greater than 0.5 pm, especially greater than 0.8 pm, and most preferably greater than 1 pm. The average droplet size can be determined by a laser diffractometer as known in the art, for example using a Malern Mastersizer 3000.

In a further aspect, the present invention provides a method for preventing and/or controlling pathogenic fungal infestation of a plant and/or undesired plant growth and/or undesired insect or mite infestation and/or regulating plant growth, the method comprising applying the emulsifiable concentrate composition of the present invention or the emulsion composition of the present invention to the plants, plant propagation materials or plant parts to be protected, their locus, or the environment of the pest infestation.

When the pesticide is used in crop protection, the application rate of the active pesticidal component may be from 0.001 to 2 kg/ha, preferably from 0.005 to 2 kg/ha, more preferably from 0.05 to 0.9 kg/ha, especially from 0.1 to 0.75 kg/ha. The application rate will depend upon such factors as the nature of the desired effect.

In the treatment of plant propagation materials such as seeds, for example by means of dusting, coating or soaking seeds, the amount of the active pesticidal component employed may be from 0.1 to 1000 g/100 kg, preferably 1 to 1000 g/100 kg, more preferably from 1 to 100 g/100 kg, and still more preferably from 5 to 100 g/100 kg of plant propagation materials, preferably seeds.

When the active pesticidal component is used to protect materials or store products, the application rate thereof depends on such factors as the type of the application area and the desired effect. The application rate may be, for example, from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg of the active substance per cubic meter of the materials processed.

Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, and other pesticides (such as herbicides, pesticides, fungicides, growth regulators, and safeners) can be added in the form of a premix to the emulsion composition or, optionally, added, for example in the form of a tank mix, thereto immediately before use. These reagents may be mixed with the composition of the present invention in a weight ratio of from 1:100 to 100:1, preferably from 1:10 to 10:1.

Generally, the user applies the composition of the present invention by means of a predosage device, a knapsack sprayer, a spray tank, a spray plane or an irrigation system. Such devices and their uses are known in the art.

Zs The present invention provides a number of technical advantages, in particular as follows: The emulsifiable concentrate composition exhibits a high stability, in particular at low temperatures, for example below -5°C. The pesticide does not precipitate, layer or crystallize in the concentrate composition at these low temperatures.

Similarly, the pesticide does not precipitate, layer or crystallize in the emulsion composition obtained from the concentrate composition at low temperatures, for example below -5°C. As a consequence, high pesticide concentrations can be used in the concentrate composition.

Further, when the concentrate composition is diluted with water, a stable emulsion forms spontaneously, with little or no mixing required.

The concentrate composition can be stored for an extended period of time without deterioration or loss of efficacy The concentrate composition does not require the presence of water and most preferably is substantially or wholly free of water. This reduces the opportunity for bacterial growth in the composition during prolonged storage.

Adjuvants, such as alcohol alkoxylates, can be introduced into the concentrate s composition at high concentrations without adverse effects on the stability or activity of the composition.

As a result of the high stability of the composition, in particular the active pesticide component in solution, the composition does not causes blockages of spray filters or nozzles used during application of the composition or the emulsion to composition.

The concentrate composition may be diluted with hard water, without adverse effects, such as precipitation of components.

In a further aspect, the present invention provides the use of an amide of formula (I) as hereinbefore described and a lactamide of formula (II) as hereinbefore described to increase the stability of an emulsifiable concentrate formulation of a water-insoluble pesticide.

Embodiments of the present invention will be described, for illustration only, by way of the following working examples.

All percentages are % weight, unless otherwise indicated.

Example 1

Emulsifiable concentrate (EC) formulations A to E containing the active substance prothioconazole were prepared by mixing the components indicated in Table 1 below and making up to a total volume of 1 L with N,N-dimethyl decenamide.

Table 1

FORMULATION A B C D E

Prothioconazole (gIL) 100 150 200 250 300 N,N-dimethyl decenamide Make up Make up Make up Make up Make up to 1 L to 1 L to 1 L to 1 L to 1 L N, N-dimethyl lactamide 200 180 250 150 50 (g/L) Calcium dodecyl benzenesulfonate 50 50 80 75 50 (gIL) Castor oil ethoxylate (g/L) 50 75 50 75 100 Aromatic hydrocarbon solvent - - - 100 50 (gIL) Each formulation A to E was a clear solution.

Each of formulations A to E was tested to determine its stability at ambient and low temperature (-5°C), emulsion effect and dilution stability. The test procedures were as follows: Stability at Ambient Temperatures 500 ml of each of the EC formulations A to E was stored at room temperature and each formulation was observed after 6 months.

Samples that did not show any crystals are indicated as "+". Samples showing any crystal or precipitate formation are indicated as "-".

Low Temperature Stability 500 ml of each of the EC formulations A to E was stored at -5°C and each formulation was observed after 1 month.

Samples that did not show any crystal formation are indicated as "+" Samples showing any crystal formation are indicated as "-".

Emulsification Effect ml of each of the EC formulations A to E was diluted with water by 200 times to observe the spontaneous emulsification ability of the composition and the dispersibility of the emulsion.

Samples with a fast, spontaneous emulsification ability and uniform emulsion distribution are indicated as "Good". Samples with moderate spontaneous emulsification ability or poor emulsion effect are indicated as "Average". Samples with slow spontaneous emulsification ability or poor emulsion effect are indicated as "Poor".

Dilution Stability 10 ml of each of the EC formulations A to E was diluted with water by 200 times, and then placed in a 25°C constant temperature water bath and observed after 24 hours.

Samples that did not show any crystal formation were marked as "+". Samples showing any crystal formation are indicated as "-".

The results of these tests are summarised in Table 2 below.

Table 2

FORMULATION A B C D E

Stability at Ambient + + + + + Low Temperature Stability + + + + + Emulsification effect Good Good Good Good Good Dilution stability + + + + + As can be seen from the results in Table 2, all of the formulations A to E exhibited a high stability of the active component at both ambient and low temperatures, excellent emulsification and a high stability when diluted with water.

Example 2

Prothioconazole-containing emulsifiable concentrate (EC) formulations were prepared by mixing the components shown in Table 3.

Formulations COMP 1 to COMP 5 are for comparative purposes only and are not embodiments of the present invention.

Table 3

FORMULATION D F COMP 1 COMP 2 COMP 3 COMP 4 COMP 5 Prothioconazole (g/L) 250 250 250 250 250 250 250 N,N-dimethyl decenamide (g/L) Make up to Make up - Make up to - 150 - 1 L to 1 L 1 L N,N-dimethyl lactamide (g/L) 150 150 Make up to 1 L - - - 150 Calcium dodecyl benzenesulfonate (g/L) 75 75 75 75 75 75 75 Castor oil ethoxylate (g/L) 75 75 75 75 75 75 75 Aromatic Make up Make up Make up hydrocarbon solvent (g/L) 100 - 100 100 to 1 L to 1 L to 1 L The formulations were subjected to the test described in Example 1 above. The results are summarised in Table 4 below.

Table 4

FORMULATION D F COMP 1 COMP 2 COMP 3 COMP 4 COMP 5 Stability at Ambient + + + + + + + Low Temperature Stability + + _ + _ + -Emulsification effect Good Good Good Good Average Average Average Dilution stability + + + - - - + As can be seen, formulations D and F exhibited a high stability of the active component at both ambient and low temperatures, excellent emulsification and a high stability when diluted with water. The comparative formulations, COMP 1 to COMP 5, failed at least one of the tests, indicating a poor quality EC formulation.

Example 3

Emulsifiable concentrate (EC) formulations were prepared by mixing the components shown in Table 5.

Table 5

FORMULATION G H I J K

Tebuconazole (g/L) 250 - - 100 -Difenoconazole (g/L) - 200 - - 150 Mefentrifluconazole (g/L) 200 Prothioconazole (g/L) - - - 150 100 N,N-dimethyl octenamide (g/L) Make up Make up to 1 L to 1 L Mixture of N,Ndimethyloctenamide / decenamide - Make up Make up - Make up to 1 L to 1 L to 1 L N,N-diethyl lactamide (g/L) 300 150 50 N,N-dipropyl lactamide (g/L) - 200 - - 80 Vegetable oil ethoxylate (g/L) 60 - 80 - 75 Fatty alcohol ethoxylate (g/L) 80 60 100 50 EO-PO block copolymer (g/L) 60 30 50 Solvesso 200ND (g/L) - - - 50 50 The formulations were subjected to the tests described in Example 1.

The results are summarised in Table 6 below.

Table 6

FORMULATION G H I J K

Stability at Ambient + + + + + Low Temperature Stability + + + + + Emulsification effect Good Good Good Good Good Dilution stability + + + + + As can be seen, formulations G to K exhibited a high stability of the active component at both ambient and low temperatures, excellent emulsification and a high stability when diluted with water.

Example 4

Emulsifiable concentrate (EC) formulations were prepared by mixing the components shown in Table 7.

Table 7

FORMULATION L M N 0 Pyraclostrobin (g/L) 250 - 150 100 Picoxystrobin (g/L) 200 50 Prothioconazole (g/L) 150 100 N,N-dimethyl Make up to Make up to Make up to Make up to decenamide 1 L 1 L 1 L 1 L N, N-dimethyl lactamide (g/L) 120 160 300 200 Castor oil 50 60 50 75 ethoxylate (g/L) Calcium dodecyl benzenesulfonate (g/L) 50 50 80 50 Solvesso 200ND (g/L) - 50 - 50 The formulations L to 0 were subjected to the tests described in Example 1 above. The results are summarised in Table 8.

Table 8

FORMULATION L M N 0 Stability at Ambient + + + + Low Temperature Stability + + + + Emulsification effect Good Good Good Good Dilution stability + + + + As can be seen, formulations L to 0 exhibited a high stability of the active component at both ambient and low temperatures, excellent emulsification and a high stability when diluted with water.

Example 5

Emulsifiable concentrate (EC) formulations were prepared by mixing the components shown in Table 9.

Table 9

FORMULATION P Q R S T U

Pinoxaden (g/L) 50 - - - - - Cyhalofop-butyl (g/L) - 100 - - - - Pendimethalin (g/L) - - 330 - - -Pyriproxyfen (g/L) 100 Clocythrin (g/L) 50 Imidacloprid (g/L) - - - - - 240 Mixture of N,Ndimethyl octenamide / decenamide Make up Make up Make up Make up Make up Make up to 1 L to 1 L to 1 L to 1 L to 1 L to 1 L N,N-dimethyl lactamide (g/L) 80 60 100 50 30 120 Ethoxylated sorbitan (g/L) 80 80 80 75 50 100 Solvesso 200ND (g/L) 30 50 The formulations L to 0 were subjected to the tests described in Example 1 above. The results are summarised in Table 10.

Table 10

FORMULATION P 0 R S T U Stability at Ambient + + + + + + Low Temperature Stability + + + + + + Emulsification effect Good Good Good Good Good Good Dilution stability + + + + + + As can be seen, formulations P to U exhibited a high stability of the active component at both ambient and low temperatures, excellent emulsification and a high stability when diluted with water.

Claims

CLAIMS1. A pesticidal emusifiable concentrate (EC) composition comprising: a) a water-insoluble pesticide; b) an amide of general formula (I): hl ( I) wherein n is an integer from 3 to 15; and c) a lactamide of general formula Op: CHa -CH(OH) -C(0) -N -R1 R2 wherein each of R1 and R2 is independently selected from a Ci to C4 alkyl group.
2. The composition according to claim 1, wherein the pesticide is selected from a microbiocide, a herbicide, an insecticide or mixtures thereof.
3. The composition according to either of claims 1 or 2, wherein the pesticide is selected from triazole pesticides, methoxyacrylate pesticides, carboxamide pesticides and mixtures thereof
4. The composition according to claim 3, wherein the pesticide is selected from azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, mefentrifluconazole, ipfentrifluconazole, azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, fenoxystrobin/flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, boscalid, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, penthiopyrad and mixtures thereof.
5. The composition according to any preceding claim, wherein the pesticide is present in the composition in an amount of from 0.1 to 60% by weight.
6. The composition according to any preceding claim, wherein n is an integer from 5 to 10.
7. The composition according to any preceding claim, wherein the amide of formula (I) is present in the composition in an amount of from 5 to 70% by weight.
8. The composition according to any preceding claim, wherein each of R1 and R2 are selected from Ci to C3 alkyl groups.
The composition according to claim 8, wherein both R1 and R2 are methyl.
10. The composition according to any preceding claim, wherein the lactamide of formula (II) is present in the composition in an amount of from 0.3 to 50% by weight.
11. The composition according to any preceding claim, wherein the amide of formula (I) is present in a greater amount by weight than the lactamide of formula (II).
12. The composition according to any preceding claim, wherein weight ratio of the amide of formula (I) to the lactamide of formula (II) present in the composition is from 1:1 to 20:1.
13. The composition according to any preceding claim, wherein the composition s comprises not more than 1% by weight of water.
14. The composition according to any preceding claim, wherein the composition further comprises one or more solvents selected from hydrocarbon solvents and plant-derived solvents.
15. The composition according to claim 14, wherein the further one or more solvents are present in the composition in an amount of from 0.1 to 50% by weight.
16. The composition according to any preceding claim, wherein the total amount of solvent present in the composition if from 5 to 90% by weight.
17. The composition according to any preceding claim, wherein the composition comprises from 10 to 60% by weight of an amide of formula (I), from 1 to 30% by weight of a lactamide of formula (I), and optionally from 1 to 20% by weight of hydrocarbon solvent, wherein the total amounts of these components adds up to from 12 to 90% by weight of the composition.
18. The composition according to any preceding claim, further comprising one or more auxiliary agents selected from liquid carriers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetrants, protective colloids, adhesives, thickening agents, microbicides, antifreezing agents, antifoaming agents, colorants, tackifiers and binders.
19. A method for preparing the emulsifiable concentrate composition according to any preceding claim, the method comprising mixing: a water-insoluble pesticide; an amide of formula (I) as hereinbefore described; a lactamide of formula (II) as hereinbefore described; and optionally one or more auxiliary agents.
20. An emulsion composition comprising the emulsifiable concentrate composition according to any of claims 1 to 18 or prepared by a method according to claim 19 s and water.
21. The emulsion composition according to claim 20, wherein the weight ratio of water to the emulsifiable concentrate composition is from 1:1 to 1000:1.
22. The emulsion composition according to either of claims 20 or 21, wherein the average droplet size of the dispersed phase is greater than 0.1 um.
23. A method for preventing and/or controlling pathogenic fungal infestation of a plant and/or undesired plant growth and/or undesired insect or mite infestation and/or regulating plant growth, the method comprising applying the emulsifiable concentrate composition according to any of claims 1 to 18 or the emulsion composition according to any of claims 20 to 22 to the plants, plant propagation materials or plant parts to be protected, their locus, or the environment of the pest infestation.
24. Use of the emulsifiable concentrate composition according to any of claims 1 to 18 or the emulsion composition according to any of claims 20 to 22 for preventing and/or controlling pathogenic fungal infestation of a plant and/or undesired plant growth and/or undesired insect or mite infestation and/or regulating plant growth.
25. Use of: a) an amide of general formula (I): ( I) wherein n is an integer from 3 to 15; and b) a lactamide of general formula (II): CHa -CH(OH) -C(0) -N -R1 (II) R2 wherein each of R1 and R2 is independently selected from a Ci to C.4 alkyl group; to increase the stability of an emulsifiable concentrate formulation of a water-insoluble pesticide.