WO2014154447A1 - Concentré émulsionnable comprenant un pesticide, un lactate d'alkyle et un amide gras - Google Patents

Concentré émulsionnable comprenant un pesticide, un lactate d'alkyle et un amide gras Download PDF

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Publication number
WO2014154447A1
WO2014154447A1 PCT/EP2014/054081 EP2014054081W WO2014154447A1 WO 2014154447 A1 WO2014154447 A1 WO 2014154447A1 EP 2014054081 W EP2014054081 W EP 2014054081W WO 2014154447 A1 WO2014154447 A1 WO 2014154447A1
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Prior art keywords
weight
concentrate
water
concentrate according
alkyl
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PCT/EP2014/054081
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English (en)
Inventor
Winfried Mayer
Jürgen JAKOB
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Basf Se
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Application filed by Basf Se filed Critical Basf Se
Priority to EA201500974A priority Critical patent/EA030150B1/ru
Priority to UAA201510376A priority patent/UA118758C2/uk
Priority to BR112015018869-9A priority patent/BR112015018869B1/pt
Priority to CN201480018172.XA priority patent/CN105188363A/zh
Priority to AU2014243307A priority patent/AU2014243307B2/en
Publication of WO2014154447A1 publication Critical patent/WO2014154447A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • Emulsifiable concentrate comprising pesticide, alkyl lactate and fatty amide
  • Subject matter of the present invention is an emulsifiable concentrate comprising a water- insoluble pesticide, an alkyl lactate, and an amide of the formula (I) as defined herein.
  • the invention further relates to a process for the preparation of said concentrate; an emulsion obtainable by mixing water, a water-insoluble pesticide, the components a) and b); and 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 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.
  • Emulsifiable concentrates are widely used formulations in crop protection.
  • the disadvantage of the known emulsifiable concentrates is the poor cold stability, the pronounced tendency to crystallize and the low pesticide concentration. It was an object of the present invention to provide an emulsifiable concentrate which overcomes these disadvantages.
  • an emulsifiable concentrate comprising a water-insoluble pesticide
  • 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 mixing of the emulsifiable concentrate with water may be done at 5 to 50 °C, typically at ambient temperature such as 25 °C.
  • the emulsion usually arises spontaneously. In another form the emulsion usually arises spontaneously upon mixing with water.
  • the resulting emulsion may have an average droplet size of more than 0.1 pm, preferably more than 0.5 ⁇ , in particular more than 0.8 pm, and most preferred more than 1.1 pm.
  • the average droplet size may be determined by laser diffraction, e.g. with a Malvern Mastersizer 2000.
  • the concentrate is preferably present as a homogeneous solution. It is usually virtually free from dispersed particles.
  • Suitable alkyl lactates are aliphatic Ci-Cis-alkyl lactates (in particular C6-Cio-alkyl lactates), which may be linear or branched. Examples are cyclohexyl lactate, 2-ethylhexyl lactate, 2- 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.
  • the concentrate can comprise at least 5% by weight, preferably at least 20% by weight, more preferably at least 35% by weight, and in particular at least 45% by weight of alkyl lactate (such as 2-ethylhexyl lactate).
  • the concentrate can comprise at least 25% by weight, preferably at least 30% by weight weight of alkyl lactate (such as 2-ethylhexyl lactate).
  • the concentrate can comprise not more than 80% by weight, preferably not more than 70% by weight and in particular not more than 60% by weight of the alkyl lactate.
  • Preferred amides of the formula (I) are those in which R 1 is Cz-Cn-alkyl (preferably linear) and R 2 is methyl.
  • Especially preferred amides of the formula (I) are those in which R 1 is Cz-Cgralkyl and R 2 is methyl.
  • R is n-nonyl and R 2 is methyl.
  • Mixtures of amides of the formula (I) are also possible, for example mixtures where R 1 is C7-C11- alkyl and R 2 is methyl.
  • Mixtures of amides of the formula (I) comprise in most cases two amides of the formula (I) in an amount of in each case at least 30% by weight (preferably at least 40% by weight) based on the total amount of amides of the formula (I).
  • the concentrate can comprise not more than 60% by weight, preferably not more than 45% by weight and in particular not more than 30% by weight of amide of the formula (I).
  • the concentrate can comprise at least 5% by weight, preferably at least 10% by weight and in particular at least 15% by weight of amide of the formula (I).
  • the weight ratio of the alkyl lactate to the amide of the formula (I) may be in the range from 1 :20 to 10: 1 , preferably from 1 :10 to 4: 1 , more preferably from 1 :6 to 1 .5:1 , and in particular from 1 :4 to 1 : 1 .2.
  • the weight ratio of the alkyl lactate to the amide of the formula (I) may be in the range from 1 :10 to 20:1 , preferably from 1 :4 to 10:1 , more preferably from 1 : 1 .5 to 6: 1 , and in particular from 1 :1.2 to 3:1 .
  • the concentrate may further comprise benzyl alcohol in addition to the aforementioned solvents a) and b).
  • the concentrate can comprise not more than 30% by weight, preferably not more than 10% by weight and in particular not more than 7% by weight of benzyl alcohol.
  • the concentrate can comprise at least 0.5% by weight, preferably at least 1 .5% by weight and in particular at least 3% by weight of benzyl alcohol.
  • the concentrate may further comprise dimethyl sulfoxide (DMSO) in addition to the DMSO.
  • DMSO dimethyl sulfoxide
  • the concentrate can comprise not more than 20% by weight, preferably not more than 10% by weight and in particular not more than 3% by weight of dimethyl sulfoxide.
  • the concentrate can comprise at least 0.1 % by weight, preferably at least 0.5% by weight and in particular at least 1 % by weight of DMSO. In another form the concentrate is free of DMSO.
  • the concentrate may further comprise benzyl alcohol and dimethyl sulfoxide (DMSO) in addition to the aforementioned solvents a) and b).
  • DMSO dimethyl sulfoxide
  • the amounts of these components a), b) and optionally benzyl alcohol and optionally DMSO add up to a sum of 5 to 95% by weight, preferably 40 to 90% by weight, and in particular 55 to 85% by weight.
  • the concentrate can comprise from 20 to 80% by weight of the alkyl lactate (e.g. 2-ethylhexyl lactate), 1 to 50% by weight of the amide of the formula (I) (e.g. in which R 1 is C7-Cn-alkyl and R 2 is methyl), and optionally 1 to 25% by weight of the benzyl alcohol, wherein the amounts of these components adds up to a sum of 40 to 95% by weight.
  • alkyl lactate e.g. 2-ethylhexyl lactate
  • the amide of the formula (I) e.g. in which R 1 is C7-Cn-alkyl and R 2 is methyl
  • optionally 1 to 25% by weight of the benzyl alcohol e.g. in which R 1 is C7-Cn-alkyl and R 2 is methyl
  • the concentrate can comprise from 40 to 70% by weight of the alkyl lactate (e.g. 2- ethylhexyl lactate), 3 to 40% by weight of the amide of the formula (I) (e.g. in which R 1 is C7-C11- alkyl and R 2 is methyl), and optionally 2 to 20% by weight of the benzyl alcohol, wherein the amounts of these components adds up to a sum of 40 to 95% by weight.
  • the alkyl lactate e.g. 2- ethylhexyl lactate
  • the amide of the formula (I) e.g. in which R 1 is C7-C11- alkyl and R 2 is methyl
  • optionally 2 to 20% by weight of the benzyl alcohol wherein the amounts of these components adds up to a sum of 40 to 95% by weight.
  • the concentrate can comprise from 50 to 65% by weight of the alkyl lactate (e.g. 2- ethylhexyl lactate), 10 to 25% by weight of the amide of the formula (I) (e.g. in which R 1 is C7- Cn-alkyl and R 2 is methyl), and optionally 5 to 15% by weight of the benzyl alcohol, wherein the amounts of these components adds up to a sum of 50 to 95% by weight.
  • the alkyl lactate e.g. 2- ethylhexyl lactate
  • the amide of the formula (I) e.g. in which R 1 is C7- Cn-alkyl and R 2 is methyl
  • optionally 5 to 15% by weight of the benzyl alcohol wherein the amounts of these components adds up to a sum of 50 to 95% by weight.
  • the concentrate is free from water.
  • 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 may comprise not more than 0.3% by weight and in particular not more than 0.1 % by weight of water.
  • the concentrate may comprise further solvents (e.g. the organic solvents listed below) in addition the components a), b), benzyl alcohol and DMSO.
  • the term "further solvents" usually relates to solvents which are different from the components a), b), benzylalcohol and DMSO.
  • the concentrate can comprise not more than 30% by weight, preferably not more than 10% by weight and in particular not more than 1 % by weight of the further solvents.
  • 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 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):
  • Inhibitors of complex III at Q 0 site e.g. strobilurins: azoxystrobin, coumethoxystrobin,
  • coumoxystrobin dimoxystrobin, enestroburin, fenaminstrobin, fenoxy- strobin/flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, trifloxystrobin, 2-[2-(2,5- dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid methyl ester and 2-(2-(3-(2,6-di- chlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl- acetamide, pyribencarb, triclopyricarb/chlorodincarb, famoxadone, fenamidone;
  • - inhibitors of complex II e. g. carboxamides: benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, tecloftalam, thifluzamide, N-(4'- trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N-(2- (1 ,3,3-trimethyl-butyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide,
  • complex II e. g. carboxamides: benodanil, benzovindiflupyr, bixafen, boscalid,
  • respiration inhibitors e.g. complex I, uncouplers: diflumetorim, (5,8-difluoroquinazolin-
  • nitrophenyl derivates binapacryl, dinobuton, dinocap, fluazinam; ferimzone; organometal compounds: fentin salts, such as fentin-acetate, fentin chloride or fentin hydroxide; ametoctradin; and silthiofam;
  • DMI fungicides triazoles: azaconazole, bitertanol,
  • epoxiconazole fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole,
  • pyrimidines, pyridines and piperazines fenarimol, nuarimol, pyrifenox, triforine;
  • Delta14-reductase inhibitors aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine;
  • phenylamides or acyl amino acid fungicides benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl;
  • hymexazole hymexazole, octhilinone, oxolinic acid, bupirimate, 5-fluorocytosine, 5-fluoro-2-(p- tolylmethoxy)pyrimidin-4-amine, 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine;
  • - tubulin inhibitors such as benzimidazoles, thiophanates: benomyl, carbendazim,
  • cell division inhibitors diethofencarb, ethaboxam, pencycuron, fluopicolide, zoxamide, metrafenone, pyriofenone;
  • - methionine synthesis inhibitors anilino-pyrimidines: cyprodinil, mepanipyrim, pyrimethanil;
  • blasticidin-S blasticidin-S, kasugamycin, kasugamycin hydrochloride-hydrate, mildiomycin, streptomycin, oxytetracyclin, polyoxine, validamycin A;
  • MAP / histidine kinase inhibitors fluoroimid, iprodione, procymidone, vinclozolin, fenpiclonil, fludioxonil;
  • - Phospholipid biosynthesis inhibitors edifenphos, iprobenfos, pyrazophos, isoprothiolane;
  • lipid peroxidation dicloran, quintozene, tecnazene, tolclofos-methyl, biphenyl, chloroneb, etridiazole;
  • oxathiapiprolin oxathiapiprolin
  • organochlorine compounds e.g. phthalimides, sulfamides, chloronitriles: anilazine,
  • chlorothalonil captafol, captan, folpet, dichlofluanid, dichlorophen, flusulfamide,
  • guanidines and others guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate), dithianon, 2,6-dimethyl- 1 H,5H-[1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone;
  • glucan synthesis inhibitors validamycin, polyoxin B; melanin synthesis inhibitors:
  • abscisic acid amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat (chlormequat chloride), choline chloride, cyclanilide, daminozide, dikegulac, dimethipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet,
  • acetochlor alachlor, butachlor, dimethachlor, dimethenamid, flufenacet,
  • mefenacet metolachlor, metazachlor, napropamide, naproanilide, pethoxamid, pretilachlor, propachlor, thenylchlor;
  • - aryloxyphenoxypropionates clodinafop, cyhalofop-butyl, fenoxaprop, fluazifop, haloxyfop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuryl;
  • EPTC esprocarb, molinate, orbencarb, phenmedipham, prosulfocarb, pyributicarb, thiobencarb, triallate;
  • acifluorfen acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, fomesafen, lactofen, oxyfluorfen;
  • - pyridines aminopyralid, clopyralid, diflufenican, dithiopyr, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;
  • - sulfonyl ureas 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, tritosulfuron
  • - triazines ametryn, atrazine, cyanazine, dimethametryn, ethiozin, hexazinone, metamitron, metribuzin, prometryn, simazine, terbuthylazine, terbutryn, triaziflam;
  • ureas chlorotoluron, daimuron, diuron, fluometuron, isoproturon, linuron, metha- benzthiazuron,tebuthiuron;
  • acetolactate synthase inhibitors bispyribac-sodium, cloransulam-methyl, diclosulam, florasulam, flucarbazone, flumetsulam, metosulam, ortho-sulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam;
  • amicarbazone amicarbazone, aminotriazole, anilofos, beflubutamid, benazolin,
  • organo(thio)phosphates acephate, azamethiphos, azinphos-methyl, chlorpyrifos,
  • chlorpyrifos-methyl chlorfenvinphos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos,
  • methidathion methidathion, methyl-parathion, mevinphos, monocrotophos, oxydemeton-methyl, paraoxon, parathion, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos- methyl, profenofos, prothiofos, sulprophos, tetrachlorvinphos, terbufos, triazophos, trichlorfon;
  • - 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 I I, resmethrin, silafluofen, tau-fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, profluthrin, dimefluthrin;
  • - insect growth regulators a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron,
  • cyramazin diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexythiazox, etoxazole, clofentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadirachtin; c) juvenoids: pyriproxyfen, methoprene, fenoxycarb; d) lipid biosynthesis inhibitors:
  • - nicotinic receptor agonists/antagonists compounds dothianidin, dinotefuran, flupyradifurone, imidacloprid, thiamethoxam, nitenpyram, acetamiprid, thiacloprid, 1 -2-chloro-thiazol-5- ylmethyl)-2-nitrimino-3,5-dimethyl-[1 ,3,5]triazinane;
  • - GABA antagonist compounds endosulfan, ethiprole, fipronil, vaniliprole, pyrafluprole,
  • - macrocyclic lactone insecticides abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram;
  • oxidative phosphorylation inhibitors cyhexatin, diafenthiuron, fenbutatin oxide, propargite;
  • cryomazine cryomazine
  • the pesticide is water-insoluble. Usually, it is soluble in water to not more than 1 g/l, preferably not more than 200 mg/l and in particular to not more than 50 mg/l at 25°C. Examples of water- insoluble pesticides are fluxapyroxad. Using simple preliminary experiments, the skilled worker can select a pesticide with a suitable water-solubility from the above pesticide list.
  • the concentrate is free of metconazol.
  • the pesticide does not contain metconazol.
  • the pesticide can have a melting point of more than 40°C, preferably more than 70°C and in particular more than 90°C.
  • 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.
  • the concentrate can comprise one or more further pesticides.
  • the further pesticide is preferably water-insoluble. Usually, it is soluble in water to not more than 1 g/l, preferably not more than 200 mg/l and in particular not more than 50 mg/l at 25°C. Using simple preliminary experiments, the skilled worker can select a pesticide with a suitable water-solubility from the above pesticide list.
  • the concentrate does not comprise any further pesticide.
  • the further pesticide is epoxiconazol.
  • the concentrate comprises the water insoluble pesticide fluxapyroxad and optionally a further pesticide, which is water insoluble (e.g. epoxiconazol).
  • 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.
  • the emulsifiable concentrate can furthermore comprise auxiliaries conventionally used for crop protection products.
  • 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.
  • 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, cyclohexanol; glycols; ketones, for example cyclohexanone; esters, for example carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, for example N-methylpyrrolidone; and their mixtures.
  • 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, par
  • 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 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.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • 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 naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • phosphates are phosphate esters.
  • carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Preferred anionic surfactants are sulfates and sulfonates. Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • 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 and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-subsititued fatty acid amides are fatty acid glucamides or fatty acid
  • alkanolamides examples include esters, fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • 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.
  • 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.
  • 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 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.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones 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
  • examples are inorganic colorants (e.g. iron 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 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).
  • 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.
  • 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 C6-C22-alcohol), preferably not less than 7% by weight and in particular not less than 10% by weight.
  • the concentrate comprises a nonionic surfactant (such as alkoxylates) and an anionic surfactant (such as sulfates or sulfonates).
  • the invention furthermore relates to a process for the preparation of the emulsifiable
  • the invention furthermore relates to an emulsion obtainable (preferably obtained) by mixing water, the water-insoluble pesticide, the components a) and b) according to the invention, optionally benzyl alcohol, and optionally dimethyl sulfoxide.
  • the emulsion normally arises spontaneously upon mixing.
  • 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 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 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.
  • 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.
  • 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, especially 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.
  • 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 most preferably from 5 to 100 g, per 100 kg of plant propagation material (preferably seed) are generally required.
  • 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 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 may be added to the 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 .
  • composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • a predosage device usually from a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • 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 according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • the concentrate is highly stable to low temperatures (e.g. even below 0°C); that the pesticide does not precipitate, cream or crystallize in the concentrate at low temperatures (e.g. even below 0°C); that the pesticide does not precipitate, cream or crystallize in the emulsion obtained from the concentrate, e.g. at low temperatures (e.g. even below 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.
  • the concentrate forms a stable emulsion upon dilution with water; that adjuvants (such as alcohol alkoxylates) can be included in the concentrate formulations; that the pesticide does in the emulsion obtained from the concentrate does not clogg any spraying filters or nozzles, e.g. at low temperatures, or when diluted with hard water.
  • adjuvants such as alcohol alkoxylates
  • NS1 nonionic surfactant, liquid ethoxylated polyalkylarylphenol, HLB 12-13.
  • AS1 calcium alkylbenzenesulfonate, 40% by weight in aromatic solvent.
  • Examples 1 Preparation of emulsifiable concentrates (EC)
  • the emulsifiable concentrates of fluxapyroxad and epoxiconazol were prepared by mixing the components and making up to 1 .0 I with (S)-2-ethylhexyl lactate.
  • compositions are summarized in Table 1 .
  • Table 1 Composition (all data in g/l)
  • Example 1 The EC of Example 1 or the comparative Example Comp-1 was diluted with hard water (CIPAC D) to prepare 1000 ml of an oil-in-water emulsion containing 1 wt% of said EC. This emulsion was cycled for 60 min through a cartridge with a metal sieve (150 ⁇ ) and a pumping rate of 180 I per hour. During the test, the temperature was kept constant at about 10°C in order to simulate cold well water.
  • CIPAC D hard water

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne un concentré émulsionnable comprenant un pesticide insoluble dans l'eau, a) un lactate d'alkyle et b) un amide de formule (I), tels que définis dans la description. La présente invention concerne en outre un procédé de préparation dudit concentré, une émulsion pouvant être obtenue en mélangeant de l'eau, un pesticide insoluble dans l'eau, et les constituants a) et b); et un procédé pour lutter contre les champignons phytopathogènes et/ou une végétation indésirable et/ou une attaque indésirable par des insectes ou des acariens et/ou pour réguler la croissance de plantes, selon lequel on laisse agir le concentré ou l'émulsion sur les organismes nuisibles respectifs, sur leur environnement ou sur les plantes cultivées à protéger contre les organismes nuisibles respectifs, sur le sol et/ou sur des plantes indésirables et/ou sur les plantes cultivées et/ou leur environnement.
PCT/EP2014/054081 2013-03-27 2014-03-03 Concentré émulsionnable comprenant un pesticide, un lactate d'alkyle et un amide gras WO2014154447A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EA201500974A EA030150B1 (ru) 2013-03-27 2014-03-03 Эмульгируемый концентрат, включающий пестицид, алкиллактат и жирный амид
UAA201510376A UA118758C2 (uk) 2013-03-27 2014-03-03 Концентрат, що емульгується, який включає пестицид, алкіллактат і жирний амід
BR112015018869-9A BR112015018869B1 (pt) 2013-03-27 2014-03-03 Concentrado emulsificável, processo de preparação do concentrado, emulsão e método de controle de fungos
CN201480018172.XA CN105188363A (zh) 2013-03-27 2014-03-03 包含农药、乳酸烷基酯和脂肪酰胺的可乳化浓缩物
AU2014243307A AU2014243307B2 (en) 2013-03-27 2014-03-03 Emulsifiable concentrate comprising pesticide, alkyl lactate and fatty amide

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EP13161249.1 2013-03-27
EP13161249 2013-03-27
EP13179207 2013-08-05
EP13179207.9 2013-08-05

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WO2017017055A1 (fr) * 2015-07-27 2017-02-02 Basf Se Concentré émulsifiable comprenant un fongicide de triazole, un amide d'acide gras et un hydrocarbure aromatique
WO2017108662A1 (fr) * 2015-12-22 2017-06-29 Bayer Cropscience Aktiengesellschaft Concentrés d'émulsion de composés lipophiles
US20230139501A1 (en) * 2021-11-03 2023-05-04 Rotam Agrochem International Company Limited High-content abamectin emulsifiable concentrate
WO2023111296A1 (fr) * 2021-12-17 2023-06-22 Basf Se Composition comprenant un agent antimicrobien et un carboxamide

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017017055A1 (fr) * 2015-07-27 2017-02-02 Basf Se Concentré émulsifiable comprenant un fongicide de triazole, un amide d'acide gras et un hydrocarbure aromatique
CN107920525A (zh) * 2015-07-27 2018-04-17 巴斯夫欧洲公司 包含三唑类杀真菌剂、脂肪酸酰胺和芳族烃的可乳化浓缩物
AU2016299332B2 (en) * 2015-07-27 2020-07-09 Basf Se Emulsifiable concentrate comprising triazole fungicide, fatty acid amide and aromatic hydrocarbon
US10874105B2 (en) 2015-07-27 2020-12-29 Basf Se Emulsifiable concentrate comprising triazole fungicide, fatty acid amide and aromatic hydrocarbon
CN107920525B (zh) * 2015-07-27 2021-02-12 巴斯夫欧洲公司 包含三唑类杀真菌剂、脂肪酸酰胺和芳族烃的可乳化浓缩物
WO2017108662A1 (fr) * 2015-12-22 2017-06-29 Bayer Cropscience Aktiengesellschaft Concentrés d'émulsion de composés lipophiles
CN108471737A (zh) * 2015-12-22 2018-08-31 拜耳农作物科学股份公司 亲脂性化合物的乳液浓缩物
US11369108B2 (en) 2015-12-22 2022-06-28 Bayer Cropscience Aktiengesellschaft Emulsion concentrates of lipophilic compounds
US20230139501A1 (en) * 2021-11-03 2023-05-04 Rotam Agrochem International Company Limited High-content abamectin emulsifiable concentrate
WO2023111296A1 (fr) * 2021-12-17 2023-06-22 Basf Se Composition comprenant un agent antimicrobien et un carboxamide

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AU2014243307B2 (en) 2017-09-28
AU2014243307A1 (en) 2015-09-03
EA030150B1 (ru) 2018-06-29
CN105188363A (zh) 2015-12-23
UA118758C2 (uk) 2019-03-11
EA201500974A1 (ru) 2016-04-29
BR112015018869B1 (pt) 2021-04-13

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