AU2012348730A1

AU2012348730A1 - Emulsifiable concentrate comprising pesticide, dimethyl sulfoxide, benzyl alcohol, alkyl lactate

Info

Publication number: AU2012348730A1
Application number: AU2012348730A
Authority: AU
Inventors: Cedric Dieleman; Winfried Mayer; Thomas Ottillinger; Ralph STEINBACHER; Siegfried Strathmann
Original assignee: BASF SE
Current assignee: BASF SE
Priority date: 2011-12-05
Filing date: 2012-11-14
Publication date: 2014-07-03
Also published as: CA2854845A1; AR089659A1; CR20140241A; EA201400650A1; KR20140099926A; EP2787811A1; WO2013083372A1; BR112014013029A2

Abstract

Subject matter of the present invention is an emulsifiable concentrate comprising a water-insoluble pesticide, benzylalcohol, alkyl lactate and not more than 40% by weight of dimethyl sulfoxide. A further subject matter is an emulsion obtainable by mixing water with the emulsifiable concentrate; a process for the preparation of the emulsifiable concentrate; and a method for controlling phytopathogenic fungi and/or undesired vegetation and/or undesired attack by insects or mites and/or for regulating the growth of plants, where the concentrate or the emulsion is allowed to act on the respective pests, their environment or on the crop plants to be protected from the respective pests, on the soil and/or on undesired plants and/or on the crop plants and/or their environment.

Description

WO 2013/083372 PCT/EP2012/072565 1 Emulsifiable concentrate comprising pesticide, dimethyl sulfoxide, benzyl alcohol, alkyl lactate Description 5 Subject matter of the present invention is an emulsifiable concentrate comprising a water insoluble pesticide, benzyl alcohol, alkyl lactate and not more than 40% by weight of dimethyl sulfoxide. A further subject matter is an emulsion obtainable by mixing water with the emulsifiable concentrate; a process for the preparation of the emulsifiable concentrate; and a method for controlling phytopathogenic fungi and/or undesired vegetation and/or undesired 10 attack by insects or mites and/or for regulating the growth of plants, where the concentrate or the emulsion is allowed to act on the respective pests, their environment or on the crop plants to be protected from the respective pests, on the soil and/or on undesired plants and/or on the crop plants and/or their environment. The present invention comprises combinations of preferred features with other preferred features. 15 Emulsifiable concentrates (also referred to as emulsion concentrates or EC) are widely used formulations in crop protection. The disadvantage of the known emulsion concentrates is the poor cold stability, the pronounced tendency to crystallize and the low pesticide concentration. 20 It was an object of the present invention to provide an emulsion concentrate which overcomes these disadvantages. The object was achieved by an emulsifiable concentrate comprising a water-insoluble pesticide, benzyl alcohol, alkyl lactate and not more than 40% by weight of dimethyl sulfoxide. 25 Usually, an emulsifiable concentrate is taken to mean compositions which form an oil-in-water emulsion upon mixing with water (e.g. in a weight ratio of 1 part concentrate to 99 parts water). The emulsion usually arises spontaneously. The resulting emulsion may have an average droplet size of more than 0.1 pm, preferably more than 0.5 pm, in particular more than 0.8 pm, 30 and most preferred more than 1.1 pm. The resulting emulsion may have an average droplet size of up to 30 pm, preferably up to 10 pm, in particular up to 5 pm. The average droplet size may be determined by laser diffraction, e.g. with a Malvern Mastersizer 2000. Usually the resulting emulsion is not a miniemulsion, and not a microemulsion. 35 The concentrate is preferably present as a homogeneous solution. It is usually virtually free from dispersed particles. Suitable alkyl lactates are aliphatic C 1

-C

18 -alkyl lactates (in particular C 6

-C

1 o-alkyl lactates), which may be linear or branched. Examples are cyclohexyl lactate, 2-ethylhexyl lactate, 2 40 methylcyclohexyl lactate, heptyl lactate, octyl lactate, or mixtures of these. Especially preferred is 2-ethylhexyl lactate. The alkyl lactates can be present in the form of D- and/or L-lactates, with the L-lactates being preferred.

WO 2013/083372 PCT/EP2012/072565 2 The concentrate can comprise not less than 10% by weight, preferably not less than 15% by weight, more preferably not less than 20% by weight and in particular not less than 30% by weight of alkyl lactate (such as 2-ethylhexyl lactate). The concentrate can comprise not more than 80% by weight, preferably not more than 65% by weight and in particular not more than 5 50% by weight of alkyl lactate (such as 2-ethylhexyl lactate). The concentrate can comprise not more than 30% by weight, preferably not more than 20% by weight, more preferably not more than 15% by weight and in particular not more than 10% by weight of dimethyl sulfoxide (DMSO). 10 The concentrate can comprise not more than 50% by weight, preferably not more than 35% by weight and in particular not more than 28% by weight of benzyl alcohol. The concentrate can comprise not less than 3% by weight, preferably not less than 8% by weight and in particular not less than 15% by weight of benzyl alcohol. 15 The concentrate can comprise from 0.5 to 20% by weight of DMSO, from 5 to 50% by weight of benzyl alcohol and from 10 to 60% by weight of alkyl lactate (such as 2-ethylhexyl lactate). Preferably, the concentrate can comprise from 1 to 10% by weight of DMSO, from 15 to 30% by weight of benzyl alcohol and from 15 to 50% by weight of alkyl lactate (such as 2-ethylhexyl 20 lactate). In most cases, the concentrate is free from water. In another form, the concentrate is essentially free from water. It can comprise not more than 3% by weight, preferably not more than 1% by weight and in particular not more than 0.5% by weight of water. In special form, the concentrate 25 may comprise not more than 0.3% by weight and in particular not more than 0.1 % by weight of water. The term pesticides refers to at least one active substance selected from the group of the fungicides, insecticides, nematicides, herbicides, safeners and/or growth regulators. Preferred pesticides are fungicides, insecticides, herbicides and growth regulators. Especially preferred 30 pesticides are fungicides. Mixtures of pesticides from two or more of the abovementioned classes may also be used. The skilled worker is familiar with such pesticides, which can be found, for example, in Pesticide Manual, 15th Ed. (2009), The British Crop Protection Council, London. The following pesticides are suitable, by way of example (pesticides A) to K) are fungicides): 35 A) Respiration inhibitors - complex-Ill-inhibitors at the Qo-site (for example strobilurins): azoxystrobin, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, fenaminstrobin, fenoxy strobin/flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, 40 picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, methyl 2-[2 (2,5-d imethylphenyloxymethyl)phenyl]-3-methoxyacrylate, 2-(2-(3-(2,6-dichloropheny)-1 methylallylideneaminooxymethyl)phenyl)-2-methoxyimi no-N-methylacetamide, pyribencarb, triclopyricarb/chlorodincarb, famoxadon, fenamidon; WO 2013/083372 PCT/EP2012/072565 3 - complex-Ill-inhibitors at the Qr-site: cyazofamid, amisulbrom; - complex-Il-inhibitors (for example carboxamides): benodanil, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, N-(4'-trifluoromethylthio 5 biphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(2-(1,3,3 trimethylbutyl)phenyl)-1,3-d imethyl-5-fluoro-1 H-pyrazole-4-carboxamide and N-[9 (dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1 methyl-1 H-pyrazole-4-carboxamide; - other respiration inhibitors (for example complex 1, decouplers): diflumetorim; nitrophenyl 10 derivatives: binapacryl, dinobuton, dinocap, fluazinam; ferimzone; organometal compounds: fentin salts such as fentin acetate, fentin chloride or fentine hydroxide; ametoctradin; and silthiofam; B) Sterol biosynthesis inhibitors (SBI fungicides) - C14-demethylase inhibitors (DMI fungicides): triazoles: azaconazole, bitertanol, 15 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; imidazoles: imazalil, pefurazoate, 20 prochloraz, triflumizole; pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox, triforine; - delta 14-reductase inhibitors: aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine; - 3-ketoreductase inhibitors: fenhexamid; 25 C) Nucleic acid synthesis inhibitors - phenylamides or acylamino acid fungicides: benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl; - others: hymexazole, octhilinone, oxolinic acid, bupirimate; D) Cell division and cytoskeleton inhibitors 30 - tubulin inhibitors such as benzimidazoles, thiophanates: benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate-methyl; triazolopyrimidines: 5-chloro-7-(4-methyl piperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine; - further cell division inhibitors: diethofencarb, ethaboxam, pencycuron, fluopicolid, zoxamid, metrafenon, pyriofenon; 35 E) Amino acid synthesis and protein synthesis inhibitors - methionine synthesis inhibitors (anilinopyrimidines): cyprodinil, mepanipyrim, pyrimethanil; - protein synthesis inhibitors; F) Signal transduction inhibitors - MAP/histidine kinase inhibitors: fluoroimide, iprodione, procymidone, vinclozolin, fenpiclonil, 40 fludioxonil; - G-protein inhibitors: quinoxyfen; G) Lipid and membrane synthesis inhibitors - phospholipid biosynthesis inhibitors: edifenphos, iprobenfos, pyrazophos, isoprothiolane; WO 2013/083372 PCT/EP2012/072565 4 - lipid peroxidation: dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole; - phospholipid biosynthesis and cell wall attachment: dimethomorph, flumorph, mandipropamid, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate and 4-fluorophenyl 5 N-(1 -(1 -(4-cyanophenyl)ethanesulfonyl)but-2-yl)carbamate; - compounds which affect cell membrane permeability and fatty acids: propamocarb, propamocarb hydrochloride H) "Multi-site" inhibitors - inorganic active substances: Bordeaux mixture, copper acetate, copper hydroxide, copper 10 oxychloride, basic copper sulfate, sulfur; - thio- and dithiocarbamates: ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram; - organochlorine compounds (for example phthalimides, sulfamides, chloronitriles): anilazine, chlorothalonil, captafol, captan, folpet, dichlofluanid, dichlorophen, flusulfamide, 15 hexachlorobenzene, pentachlorophenol and its salts, phthalid, tolylfluanid, N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide; - guanidines and others: guanidine, dithianon; I) Cell wall biosynthesis inhibitors - glucan synthesis inhibitors: validamycin, polyoxin B; melanin synthesis inhibitors: pyroquilon, 20 tricyclazole, carpropamid, dicyclomet, fenoxanil; J) Resistance inductors - acibenzolar-S-methyl, probenazol, isotianil, tiadinil, prohexadione-calcium; phosphonates: fosetyl, fosetyl-aluminum, phosphorous acid and its salts; K) Unknown mode of action 25 - bronopol, quinomethionate, cyflufenamid, cymoxanil, dazomet, debacarb, diclomezin, difenzoquat, difenzoquat-methyl sulfate, diphenylamine, fenpyrazamine, flumetover, flusulfamid, flutianil, methasulfocarb, nitrapyrin, nitrothal-isopropyl, oxine-copper, proquinazid, tebufloquin, tecloftalam, triazoxide, 2-butoxy-6-iodo-3-propylchromene-4-one, N-(cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluorophenyl)methyl)-2-phenyl 30 acetamide, N'-(4-(4-chloro-3-trifluoromethylphenoxy)-2,5-d imethylphenyl)-N-ethyl-N methylformamidine, N'-(4-(4-fluoro-3-trifluoromethylphenoxy)-2,5-d imethylphenyl)-N-ethyl-N methylformamidine, N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanylpropoxy)phenyl)-N ethyl-N-methylformamidine, N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanylpropoxy) phenyl)-N-ethyl-N-methylformamidine, N-methyl-(1,2,3,4-tetrahydronaphthalen-1-yl)-2-{1-[2 35 (5-methyl-3-trifluoromethylpyrazol-1 -yl)acetyl]piperidin-4-yl}thiazole-4-carboxamide, N methyl-(R)-1,2,3,4-tetrahyd ronaphthalen-1 -yl-2-{1 -[2-(5-methyl-3-trifluoromethylpyrazol-1 -yl) acetyl]piperidin-4-yl}thiazole-4-carboxamide, 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3 isoxazolyl]-2-thiazolyl]-1 -piperid inyl]-2-[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 yl]ethanone, 6-tert.-butyl-8-fluoro-2,3-dimethylquinolin-4-yl methoxyacetate, N-methyl-2-{1 40 [(5-methyl-3-trifluoromethyl-1 H-pyrazol-1 -yl)acetyl]piperidin-4-yl}-N-[(1 R)-1,2,3,4 tetrahyd ronaphthalen-1 -yl]-4-thiazolecarboxamide, 3-[5-(4-methylphenyl)-2,3 dimethylisoxazolidin-3-yl]-pyridine, 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolid in-3-yl] pyridine (pyrisoxazol), N-(6-methoxypyridin-3-yl) cyclopropanecarboxamide, 5-chloro-1-(4,6- WO 2013/083372 PCT/EP2012/072565 5 d imethoxypyrimidin-2-yl)-2-methyl-1 H-benzoimidazole, 2-(4-chlorophenyl)-N-[4-(3,4-di methoxyphenyl)isoxazol-5-yl]-2-prop-2-ynyloxyacetamide; M) Growth regulators - abscisic acid, amidochlor, ancymidole, 6-benzylaminopurine, brassinolide, butralin, 5 chlormequat (chlormequat chloride), choline chloride, cyclanilid, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gibberellic acid, inabenfid, indole-3-acetic acid, maleic hydrazide, mefluidid, mepiquat (mepiquat chloride), metconazole, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazole, prohexadione (prohexadione-calcium), prohydrojasmone, thidiazuron, 10 triapenthenol, tributylphosphorotrithioate, 2,3,5-triiodobenzoic acid, trinexapac-ethyl and uniconazole; N) Herbicides - acetamides: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, flufenacet, mefenacet, metolachlor, metazachlor, napropamid, naproanilid, pethoxamid, pretilachlor, 15 propachlor, thenylchlor; - amino acid analogs; - aryloxyphenoxypropionates: clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl; - bipyridyls; 20 - carbamates and thiocarbamates: asulam, butylate, carbetamide, desmedipham, dimepiperat, eptam (EPTC), esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate; - cyclohexanediones: butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim; 25 - dinitroanilines: benfluralin, ethalfluralin, oryzalin, pendimethalin, prodiamine, trifluralin; - diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen; - hydroxybenzonitriles: bromoxynil, dichlobenil, ioxynil; - imidazolinones: imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr; 30 - phenoxyacetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, mecoprop; - pyrazines: chloridazon, flufenpyr-ethyl, fluthiacet, norflurazon, pyridate; - pyridines: aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr; 35 - sulfonylureas: amidosulfuron, azimsulfuron, bensulfuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron, iodosulfuron, mesosulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, thifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, 40 triflusulfuron, tritosulfuron, 1-((2-chloro-6-propylimidazo[1,2-b]pyridazin-3-yl)sulfonyl)-3-(4,6 dimethoxypyrimidin-2-yl)urea; - triazines: ametryne, atrazine, cyanazine, dimethametryne, ethiozine, hexazinone, metamitron, metribuzine, prometryne, simazine, terbuthylazine, terbutryne, triaziflam; WO 2013/083372 PCT/EP2012/072565 6 - ureas: chlortoluron, daimuron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, tebuthiuron; - other acetolactate synthase inhibitors: bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, orthosulfamuron, penoxsulam, 5 propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalide, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfon, pyroxsulam; - others: amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin, bencarbazone, benfluresate, benzofenap, bentazone, benzobicyclon, bromacil, bromobutide, butafenacil, butamifos, cafenstrole, carfentrazone, cinidon-ethyl, chlorthal, cinmethylin, clomazone, 10 cumyluron, cyprosulfamid, dicamba, difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, ethofumesate, etobenzanid, fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam, fluorochloridon, flurtamon, indanofan, isoxaben, isoxaflutol, lenacil, propanil, propyzamide, quinclorac, quinmerac, mesotrione, methylarsenic acid, naptalam, oxadiargyl, oxadiazone, oxaziclomefon, pentoxazone, pinoxaden, pyraclonil, pyraflufen-ethyl, pyrasulfotol, 15 pyrazoxyfen, pyrazolynate, quinoclamin, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuryltrione, tembotrione, thiencarbazone, topramezone, 4-hydroxy-3-[2-(2-methoxyethoxy methyl)-6-trifluoromethyl pyrid in-3-carbonyl]bicyclo[3.2.1 ]oct-3-en-2-one, ethyl (3-[2-chloro-4 fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)phenoxy]pyridin 2-yloxy)acetate, methyl 6-am ino-5-chloro-2-cyclopropylpyrim idine-4-carboxylate, 6-chloro 20 3-(2-cyclopropyl-6-methylphenoxy)pyridazin-4-ol, 4-amino-3-chloro-6-(4-chlorophenyl)-5 fluoropyridin-2-carboxylic acid, methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxy phenyl)pyridin-2-carboxylate and methyl 4-amino-3-chloro-6-(4-chloro-3-dimethylamino-2 fluorophenyl)pyridin-2-carboxylate; 0) Insecticides 25 - organo(thio)phosphates: acephate, azamethiphos, azinphos-methyl, chlorpyrifos, chIorpyrifos-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 30 methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon; - carbamates: alanycarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenoxycarb, furathiocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, triazamate; 35 - pyrethroids: allethrin, bifenthrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, alpha cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, imiprothrin, lambda-cyhalothrin, permethrin, prallethrin, pyrethrin I and II, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin, 40 - insect growth inhibitors: a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, cyramazin, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazin; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) WO 2013/083372 PCT/EP2012/072565 7 juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen, spiromesifen, spirotetramate; - nicotine receptor agonists/antagonists: clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1 -(2-chlorothiazol-5-ylmethyl)-2-nitrimino-3,5-di methyl 5 [1,3,5]triazinane; - GABA antagonists: endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole, pyriprole, N-5-amino-1-(2,6-dichloro-4-methylphenyl)-4-sulfinamoyl-1 H-pyrazole-3-thiocarboxamide; - macrocyclic lactones: abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram; 10 - mitochondrial electron transport chain inhibitor (METI) I acaricides: fenazaquin, pyridaben, tebufenpyrad, tolfenpyrad, flufenerim; - METI || and Ill substances: acequinocyl, fluacyprim, hydramethylnone; - decouplers: chlorfenapyr; - inhibitors of oxidative phosphorylation: cyhexatin, diafenthiuron, fenbutatin oxide, propargite; 15 - insect ecdysis inhibitors: cryomazine; - 'mixed function oxidase' inhibitors: piperonyl butoxide; - sodium channel blockers: indoxacarb, metaflumizone; - others: benclothiaz, bifenazate, cartap, flonicamid, pyridalyl, pymetrozin, sulfur, thiocyclam, flubendiamide, chlorantraniliprole, cyazypyr (HGW86); cyenopyrafen, flupyrazofos, 20 cyflumetofen, amidoflumet, imicyafos, bistrifluron and pyrifluquinazone. The pesticide is water-insoluble. Usually, it is soluble in water to not more than 1 g/l, preferably to not more than 200 mg/I and in particular to not more than 50 mg/I at 25'C. Examples of water-insoluble pesticides are fluxapyroxad. Using simple preliminary experiments, the skilled 25 worker can select a pesticide with a suitable water-solubility from the above pesticide list. The pesticide can have a melting point of more than 40 0 C, preferably more than 70'C and in particular more than 90'C. 30 The pesticide is preferably present in the concentrate in dissolved form. Using simple preliminary experiments, the skilled worker can select, from the above pesticide list, a pesticide with a suitable solubility. In addition to the water-insoluble pesticide, the concentrate can comprise one or more further 35 pesticides. The further pesticide is preferably water-insoluble. Usually, it is soluble in water to not more than 1 g/l, preferably to not more than 200 mg/I and in particular to not more than 50 mg/I at 25 0 C. Using simple preliminary experiments, the skilled worker can select a pesticide with a suitable water-solubility from the above pesticide list. In an especially preferred form, the concentrate does not comprise any further pesticide. In another especially preferred form, the 40 further pesticide is epoxiconazol. In a preferred form the concentrate comprises the water insoluble pesticide fluxapyroxad and optionally a further pesticide, which is water insoluble (e.g. epoxiconazol).

WO 2013/083372 PCT/EP2012/072565 8 The concentrate may comprise from 0.1 to 60% by weight, preferably from 1 to 25% by weight, in particular from 5 to 15% by weight, of pesticide, the basis being the total of all the pesticides present in the concentrate. 5 The emulsifiable concentrate can furthermore comprise auxiliaries conventionally used for crop protection products. Suitable auxiliaries are solvents, liquid carriers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetrants, protective colloids, stickers, thickeners, bactericides, antifreeze agents, antifoam agents, colorants, adhesives and binders. 10 Suitable solvents and liquid carriers are organic solvents such as mineral oil fractions with medium to high boiling point, for example kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, for example toluene, paraffin, tetrahydro naphthalene, alkylated naphthalenes; alcohols, for example ethanol, propanol, butanol, 15 cyclohexanol; glycols; ketones, for example cyclohexanone; esters, for example lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, for example N-methylpyrrolidone, fatty acid dimethyl amides; and their mixtures. Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and 20 amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetrant, protective colloid, or auxiliary. Examples of surfactants are listed in McCutcheon's, Vol.1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.). 25 Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of 30 naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or 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. 35 Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide 40 and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose WO 2013/083372 PCT/EP2012/072565 9 esters or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate. Preferred nonionic surfactants are alkoxylates. Nonionic surfactants such as alkoxylates may also be employed as adjuvants. 5 Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. 10 Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines. Suitable adjuvants are compounds which have negligible or even no pesticidal activity 15 themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5. 20 Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones, chloroisothiazolinones and benzisothiazolinones. Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerol. Suitable antifoam agents are silicones, long-chain alcohols, and salts of fatty acids. Suitable colorants (e.g. in red, blue, or green) are pigments which are sparingly soluble in water, and water-soluble dyes. Examples are inorganic colorants (e.g. iron 25 oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin, azo and phthalocyanine colorants). The concentrate preferably comprises at least one anionic surfactant. The concentrate usually comprises not less than 0.5% by weight of anionic surfactants, preferably not less than 2% by 30 weight and in particular not less than 3% by weight. The composition can comprise not more than 30% by weight of anionic surfactants, preferably not more than 15% by weight and in particular not more than 10% by weight. The concentrate preferably comprises at least one nonionic surfactant (such as alkoxylates, 35 especially alkoxylated alcohols). The concentrate usually comprises not less than 1 % by weight of nonionic surfactants, preferably not less than 5% by weight and in particular not less than 10% by weight. The composition can comprise not more than 65% by weight of nonionic surfactants, preferably not more than 45% by weight and in particular not more than 35% by weight. 40 In a preferred form, the concentrate preferably comprises at least one alkoxylate, in particular an alkoxylated C6-C22-alcohol. The concentrate usually comprises not less than 2% by weight of alkoxylates (in particular an alkoxylated C 6

-C

22 -alcohol), preferably not less than 7% by weight WO 2013/083372 PCT/EP2012/072565 10 and in particular not less than 10% by weight. Preferably, the concentrate comprises a nonionic surfactant (such as alkoxylates) and an anionic surfactant (such as sulfates or sulfonates). 5 The invention furthermore relates to a process for the preparation of the emulsifiable concentrate according to the invention by mixing the water-insoluble pesticide, not more than 40% by weight of dimethyl sulfoxide, benzyl alcohol and alkyl lactate. In most cases, the pesticide will be dissolved in the solvent upon mixing. 10 The invention furthermore relates to an emulsion obtainable (preferably obtained) by mixing water with the emulsifiable concentrate according to the invention. The emulsion normally arises spontaneously upon mixing. In most cases, the emulsion is an oil-in-water emulsion. The mixing ratio of water to concentrate can be in the range of from 1000 to 1 up to 1 to 1, preferably 200 to 15 1 up to 3 to 1. The invention furthermore relates to a method for controlling phytopathogenic fungi and/or undesired vegetation and/or undesired attack by insects or mites and/or for regulating the growth of plants, where the concentrate according to the invention or the emulsion according to 20 the invention is allowed to act on the respective pests, their environment or on the crop plants to be protected from the respective pests, on the soil and/or on undesired plants and/or on the crop plants and/or their environment. In general, the therapeutic treatment of humans and animals is excluded from the method for controlling phytopathogenic fungi and/or undesired vegetation and/or undesired attack by insects or mites and/or for regulating the growth of plants. 25 When employed in crop protection, the application rates of the pesticides amount to from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha and in particular from 0.1 to 0.75 kg per ha, depending on the nature of the desired effect. In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching 30 seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and in particular from 5 to 100 g, per 100 kg of plant propagation material (preferably seed) are generally required. When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 35 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material. Various types of oils, wetters, adjuvants, fertilizers or micronutrients and further pesticides (for example herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the 40 emulsion in the form of a premix or optionally only shortly before use (tank mix). These agents can be admixed to the compositions according to the invention at a weight ratio of from 1:100 to 100:1, preferably from 1:10 to 10:1.

WO 2013/083372 PCT/EP2012/072565 11 The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition 5 according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area. Advantages of the present invention are, inter alia, that the concentrate is highly stable to low temperatures (e.g. even below 0 0 C); that the pesticide does not precipitate, cream or crystallize 10 in the concentrate at low temperatures (e.g. even below 0 0 C); that high pesticide concentrations in the concentrate can be employed; that an emulsion forms spontaneously upon dilution of the concentrate with water; that the concentrate is capable of being stored over prolonged periods; that the concentrate does not require the presence of water (e.g. because it might freeze below 0 'C or would favour bacterial growth during storage); that the concentrate forms a stable 15 emulsion upon dilution with water; that the concentrate ; or that adjuvants (such as alcohol alkoxylates) can be included in the concentrate formulations. The examples which follow illustrate the invention without imposing any limitation. 20 Examples DMA: dimethyl adipate BenzOH: benzyl alcohol Al1: fluxapyroxad 25 A12: epoxiconazole A13: pyraclostrobin NS1: nonionic surfactant, liquid ethoxylated polyalkylarylphenol, HLB 12-13. NS2: nonionic surfactant, liquid alkoxylated fatty alcohol, surface tension (1 g/l, 23'C) 28-30 mN/m; Brookfield viscosity (23'C) 70-80 mPas. 30 AS1: calcium tetrapropylenebenzenesulfonate, 40% by weight in aromatic solvent. AS2: polyarylphenylethyl sulfate, acid number 39-52 mg KoH/g. Example 1 - 11: Preparation of emulsion concentrates The emulsifiable concentrates of fluxapyroxad (in each case 62.5 g/l) were prepared by mixing the components and making up to 1.0 I with (S)-2-ethylhexyl lactate. 35 Table 1: Composition of examples 1-11 (all data in g/) Example BenzOH DMSO DMA AS1 NS1 NS2 NS3 1 200 30 50 50 50 150 50 2 100 30 50 50 50 250 50 3 200 50 100 50 50 100 75 4 200 30 100 25 25 100 100 5 200 30 50 50 50 150 50 WO 2013/083372 PCT/EP2012/072565 12 6 200 30 50 100 50 150 50 7 200 30 50 140 30 150 50 8 200 30 50 70 50 150 150 9 200 60 100 50 50 150 50 10 200 60 150 50 50 150 50 11 200 30 100 75 75 100 50 Example 12-25: Preparation of emulsion concentrates The emulsifiable concentrates in Table 2 were prepared by mixing the components and making up to 1.0 I with (S)-2-ethylhexyl lactate. 5 Table 2: Composition of examples 12-16 (all data in g/) Example All A12 A13 BenzOH DMSO AS1 AS2 NS1 NS2 12 63 63 - 250 50 75 - 75 13 63 63 - 250 50 90 - 60 150 14 63 63 - 250 50 60 - 90 150 15 63 63 - 250 50 45 - 105 150 16 63 63 - 250 50 30 - 120 150 17 63 63 - 250 50 15 - 135 150 18 59 63 - 250 50 75 - 75 19 50 50 81 200 30 - 50 100 200 20 50 50 81 250 - 75 - 75 21 50 50 81 250 30 75 - 75 22 50 50 81 250 30 75 - 75 150 23 50 50 81 250 30 - 50 50 24 42 42 67 200 30 - 50 100 200 25 42 42 61 200 30 - 50 100 200

Claims

1. An emulsifiable concentrate comprising a water-insoluble pesticide, benzyl alcohol, alkyl lactate and not more than 40% by weight of dimethyl sulfoxide. 5

2. The emulsifiable concentrate according to claim 1, comprising not more than 20% by weight of dimethyl sulfoxide.

3. The emulsifiable concentrate according to claim 1 or 2, comprising not less than 30% by 10 weight of 2-alkyl lactate.

4. The emulsifiable concentrate according to claims 1 to 3, comprising not more than 50% by weight of benzyl alcohol. 15

5. The emulsifiable concentrate according to claims 1 to 4, comprising 0.5 to 20% by weight of DMSO, 5 to 50% by weight of benzyl alcohol and 10 to 60% by weight of alkyl lactate.

6. The emulsifiable concentrate according to claims 1 to 5, comprising 1 to 10% by weight of DMSO, 15 to 30% by weight of benzyl alcohol and 15 to 50% by weight of alkyl lactate. 20

7. The emulsifiable concentrate according to claims 1 to 6, comprising a nonionic and an anionic surfactant.

8. The emulsifiable concentrate according to claims 1 to 7, wherein the alkyl lactate is 2 25 ethylhexyl lactate.

9. The emulsifiable concentrate according to claims 1 to 8, wherein the concentrate is present as a homogeneous solution. 30

10. The emulsifiable concentrate according to claims 1 to 9, wherein the pesticide is soluble in water to not more than 1 g/l at 25C.

11. The emulsifiable concentrate according to claims 1 to 10, wherein the pesticide has a melting point of above 40'C. 35

12. The emulsifiable concentrate according to claims 1 to 11, wherein the concentrate comprises not more than 3% by weight of water.

13. The emulsifiable concentrate according to claims 1 to 12, wherein the pesticide is 40 fluxapyroxad.

14. An emulsion obtainable by mixing water with the emulsifiable concentrate according to claims 1 to 13. WO 2013/083372 PCT/EP2012/072565 14

15. A process for the preparation of the emulsifiable concentrate according to claims 1 to 13 by mixing the water-insoluble pesticide, dimethyl sulfoxide, benzyl alcohol and alkyl lactate. 5

16. A method for controlling phytopathogenic fungi and/or undesired vegetation and/or undesired attack by insects or mites and/or for regulating the growth of plants, where the concentrate according to any of claims 1 to 13 or the emulsion according to claim 14 is allowed to act on the respective pests, their environment or on the crop plants to be protected from the respective pests, on the soil and/or on undesired plants and/or on the 10 crop plants and/or their environment.