WO2007017040A2 - Micro-emulsions - Google Patents

Micro-emulsions Download PDF

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Publication number
WO2007017040A2
WO2007017040A2 PCT/EP2006/006904 EP2006006904W WO2007017040A2 WO 2007017040 A2 WO2007017040 A2 WO 2007017040A2 EP 2006006904 W EP2006006904 W EP 2006006904W WO 2007017040 A2 WO2007017040 A2 WO 2007017040A2
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WO
WIPO (PCT)
Prior art keywords
spp
microemulsions
concentrates
fipronil
agrochemical composition
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PCT/EP2006/006904
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English (en)
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WO2007017040A3 (fr
Inventor
Wang Bing
Ma Jufa
Guo Jingquan
Tong Xianming
Richard Dickmann
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Bayer Cropscience S.A.
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Application filed by Bayer Cropscience S.A. filed Critical Bayer Cropscience S.A.
Priority to MX2008001116A priority Critical patent/MX2008001116A/es
Priority to JP2008523177A priority patent/JP2009502826A/ja
Priority to EP06754725A priority patent/EP1912505A2/fr
Priority to BRPI0613908-6A priority patent/BRPI0613908A2/pt
Publication of WO2007017040A2 publication Critical patent/WO2007017040A2/fr
Publication of WO2007017040A3 publication Critical patent/WO2007017040A3/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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • 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

Definitions

  • the present invention relates to the field of crop protectant formulations.
  • the invention relates to liquid formulations in the form of microemulsions or concentrates thereof which comprise agrochemical active ingredients.
  • Active ingredients for crop protection are generally not employed in their pure fo ⁇ n. Depending on the field and type of application, and on physical, chemical and biological parameters, the active ingredient is employed as a mixture with conventional adjuvants and additives as a solid or liquid active ingredient formulation.
  • Liquid formulations are described, for example, in EP-A 0 261 492, EP-A 0 394 847, WO 2004/054360, WO 95/17822, WO 98/31223, WO 89/03176, EP-A 0 357 149, WO 02/45507, GB 2 267 825 A, WO 94/23578, EP-A 0 330 904, EP-A 0 533 057, DE-A 36 24 910, WO 01/74785, EP-A 0 400 585, and EP-A 0 118 579.
  • the object of the present invention was to provide an improved crop protectant formulation with superior chemical and physical stability and agrochemical activity.
  • the present invention relates to microemulsions and concentrates thereof comprising
  • fipronil ⁇ 5-amino-l-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-[(trifluoromethyl)-sulfinyl]-lH- pyrazole-3-carbonitrile (CAS-RN 120068-37-3) ⁇ and optionally one or more insecticidally active ingredient in addition to fipronil, b) ethonal, c) one or more anionic surfactants, and d) one or more nonionic surfactants.
  • microemulsions and concentrates thereof according to the invention may, if appropriate, additionally comprise conventional adjuvants and additives as further components.
  • microemulsion concentrate is understood as meaning a composition wliich forms microemulsions upon dilution with water, for example oil-in-water microemulsions or water-in-oil - - microemulsions.
  • a microemulsion is understood as being an emulsion which is thermodynamically stable and has a droplet size of the emulsified phase which is generally in the range of 10-400 run, preferably 50-250 nm.
  • microemulsion concentrates according to the invention comprise the following amounts of components a), b), c) and d), where "% by weight” here and in all of the description, unless otherwise defined, refers to the relative weight of the component in question based on the total weight of the formulation:
  • Component b) 0.1-5% by weight, preferably 0.5-2% by weight, especially preferably 1-2% by weight.
  • Component c) 0.1-25% by weight, preferably 1-20% by weight, especially preferably 2-15% by weight.
  • Component d) 0.1-40% by weight, preferably 1-30% by weight, especially preferably 2-15% by weight.
  • Suitable insecticidally active ingredients a are, for example, compounds selected from the group consisting of
  • acephate acequinocyl, acetamiprid, acetoprole, acrinathrin, alanycarb, aldicarb, aldoxycarb, allethrin (d- cis-trans, d-trans), allyxycarb, aluminium phosphide, amidoflumet, aminocarb, amitraz, avermectin, aza- dirachtin, azamethiphos, azinphos (-methylAethyl), azocyclotin, benclothiaz, bendiocarb, benfuracarb, bensultap, benzoximate, beta-cyfluthrin, bifenazate, bifenthrin, binapacyrl, bioallethrin, bioallethrin-S- cyclopentyl-isomer, bioethanomethrin, biopermethrin, bioresmethrin, bistriflur
  • insecticidally active ingredients a) which may be present in the microemulsions or concentrates thereof in addition to f ⁇ ronil are: cypermethrin, deltamethrin, imidacloprid, amitraz, triazophos, and their salts, for example the sodium salts, further preferred triazophos.
  • the active ingredients listed above are known from, for example, The Pesticide Manual, 13th edition (2003), British Crop Protection Council.
  • Component b) ethonal is a mixture of ethanol and benzene, which is well know to the skilled person.
  • Suitable as anionic surfactants c) are, for example, sulfates, sulfonates, phosphates and ph ' osponates of hydrocarbons which may optionally comprise alkylene oxide units.
  • the sulfates, sulfonates, - - phosphates and phosponates can exist in acid form or as salts.
  • Preferred anionic surfactants c) are those of the formula (I) hereinbelow:
  • the te ⁇ n alkylene oxide units is understood as meaning in particular units of C 2 -Ci O -alkylene oxides, such as ethylene oxide, propylene oxide or butylene oxide, it being possible for the units within the surfactant to be identical or different from one another and to be arranged as a random mixture or blockwise.
  • R is preferably a Ci-C 2 o-alkyl radical (for example methyl, ethyl, propyl, butyl) or a C 6 -C 24 -aryl radical (for example phenyl, biphenyl, naphthyl) which can optionally have attached to it one or more radicals, for example from the Ci-C 2 o-alkyl group (for example linear or branched Ci-C 2 o-alkyl such as sec-butyl or dodecyl) which can have attached to it one or more radicals such as C 6 -C 2 o-aryl radicals (for example phenyl, biphenyl, naphthyl), and C 6 -C 2 o-aryl (for example phenyl, biphenyl or naphthyl) which can optionally have attached to it one or more radicals such as Ci-Cjo-alkyl (for example methyl, ethyl, propyl, butyl), or
  • R is a radical R 2 O-(AO) W , where w is an integer from 1 to 100 and AO is an alkylene oxide unit, for example (EO) x (PO) x (BO) 2 , where EO is an ethylene oxide unit, PO a propylene oxide unit, BO a butylene oxide unit, x an integer from 0-100, y an integer from 0- 100, z an integer from 0 to 100 and the total x+y+z is at least 1, and the alkylene oxide unit, for example (EO) x (PO) y (BO) z , can be arranged randomly or blockwise, and
  • R 2 is H, a Ci-C 2 o-alkyl radical (for example methyl, ethyl, propyl, butyl) or a C 6 -C 24 -aryl radical (for example phenyl, biphenyl, naphthyl), which can optionally have attached to it one or more radicals, for example from the Ci-C 2 o-alkyl group (for example linear or branched Ci-C 2 o-alkyl such as sec- butyl or dodecyl) which can have attached to it one or more radicals such as Ce-C 2O - aryl radicals (for example phenyl, biphenyl, naphthyl), and C 6 -C 2 o-aryl (for example phenyl, biphenyl or naphthyl) which can optionally have attached to it one or more radicals such as Q-Cio-alkyl (for example methyl, ethyl, propyl, butyl), or R 2
  • alkylarylsulfonates such as dodecylbenzenesulfonates, for example alkaline earth metal dodecylbenzenesulfonates such as calcium dodecylbenzenesulfonates (for example Phenylsulfonat® CaIOO by Clariant), alkylarylpolyglycol ether sulfates and sulfonates, in particular arylalkylaryl polyglycol ether sulfates such as tristyrylphenyl polyglycol ether sulfates, in particular the alkali metal or ammonium or triethanolamine salts (for example Soprophore® series by Rhodia), alkyl ether sulfates and their salts (for example such as Genapol® LRO by Clariant), alkyl sulfates and alkylsulfonates (for example such as the Hostapur® series by Clariant), alkylarylsulfonates, for example al
  • Suitable nonionic surfactants d) are, for example, alkoxylates, for example ethoxylates, propoxylates or butoxylates and their combinations.
  • alkoxylates is understood as meaning compounds comprising alkylene oxide units, in particular units of C 2 -Ci 0 -alkylene oxides, such as ethylene oxide, propylene oxide or butylene oxide, it being possible for the units within the surfactant to be identical or different from one another and arranged randomly or blockwise.
  • alkoxylates d) are compounds of the formula (II) hereinbelow: R'-(AO) W -R 2 ( ⁇ ) in which R 1 is selected from the group H, HO, Ci-C 3 o-alkyl, which can be linear or branched (for example methyl, ethyl, propyl, butyl, pentyl, hexyl), CpQo-alkoxy, preferably Q-Cio-alkoxy, which can be linear or branched (for example methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy), C 6 -C 24 -aryl (for example phenyl), which can optionally have attached to it one or more radicals such as Ci-C 3 o-arylalkyl (for example styrylphenyl) or Ci-C 30 -alkyl, in which the alkyl groups can be linear or branched (for example butyl or dodecyl), C 6
  • R 1 is a sorbitan ester residue, a glycerol ester residue or Ci-C 3 o-alkyl-NR 4 , preferably Ci O -C 2 o-alkyl- NR 4 , in which the Ci-C 2 o-alkyl group can be linear or branched (for example dodecyl, hexadecyl, octadecyl) and in which R 4 equals H or C r Cio-alkyl (for example methyl, ethyl, propyl, butyl), R 2 equals H or CpC ⁇ -alkyl which can be linear or branched (for example methyl, ethyl, propyl, butyl, pentyl or hexyl), and
  • w is an integer from 1 to 100, •
  • AO is an alkylene oxide unit, for example (EO) x (PO) y (BO) z , where EO is an ethylene oxide unit, PO a propylene oxide unit, BO a butylene oxide unit, x an integer from 0-100, y an integer from 0-100, z an integer from 0 to 100 and the total x+y+z is at least 1, and the alkylene oxide unit, for example (EO) x (PO) y (BO) z , has a random or blockwise structure.
  • alkylaryl polyalkoxylates for example the ethoxylates, propoxylates and/or butoxylates, arylalkylaryl polyalkoxylates such as tristyrylphenyl polyalkoxylates (for example Soprophor® series by Rhodia) and alkylphenyl polyalkoxylates such as tributylphenyl polyalkoxlates (for example Sopagenat® series by Clariant), alkylene oxide block copolymers such as ethylene oxide (EO)/propylene oxide (PO) block copolymers or ethylene oxide (EOybutylene oxide (BO) block copolymers (for example Pluronic® series by BASF), polyalkylene oxides such as polyethyene oxides, polypropylene oxides or polybutylene oxides, optionally substituted at one of the two terminal oxygen atoms by Ci-C 22 -hydrocarbon radicals, preferably Cio-
  • carbon-containing radicals such as alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio, and the corresponding unsaturated and/or substituted radicals
  • their carbon skeleton can be straight-chain or branched in each case.
  • these radicals generally have 1 to 30 carbon atoms, the lower carbon skeletons, for example those having 1 to 6 carbon atoms, or, in the case of unsaturated groups, 2 to 6 carbon atoms, being preferred.
  • Alkyl radicals also in the composite meanings such as alkoxy, haloalkyl and the like, are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or sec-butyl, pentyls, hexyls, such as n-hexyl, i- hexyl and 1, 3- dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1,4- dimethylpentyl; alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals which correspond to the alkyl radicals; for example, alkenyl is allyl, l-methylprop-2-en-l-yl, 2-methylprop-2-en-l-yl, but-2-en-l-yl, but-3-en-l-yl, l-methylbut-3-en-l-yl and l-methylbut
  • Alkenyl in the form (C 3 -C 4 )alkenyl, (C 3 -C 5 )alkenyl, (C 3 -C 6 )alkenyl, (C 3 -Cg)alkenyl or (C 3 -C] 2 )- alkenyl is preferably an alkenyl radical having 3 to 4, 3 to 5, 3 to 6, 3 to 8 or 3 to 12 carbon atoms in which the double bond is not located at the carbon atom which is linked to the remaining moiety of the compound of the formula (I) ("yl" position).
  • This also applies analogously to (C 3 -C 4 )alkynyl and -the like, (C 3 -C 4 ) alkenyloxy and the like and (C 3 -C 4 )alkynyloxy and the like.
  • a hydrocarbon radical means a straight-chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic hydrocarbon radical, for example alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl.
  • a hydrocarbon radical preferably has 1 to 40 carbon atoms, with preference 1 to 30 carbon atoms; a hydrocarbon radical is especially preferably alkyl, alkenyl or alkynyl having up to 12 carbon atoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydro- naphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl.
  • a heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic and unsubstituted or substituted; it preferably contains one or more hetero atoms in the ring, preferably from the group consisting of N, O and S; it is preferably an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms and contains 1, 2 or 3 hetero atoms.
  • the heterocyclic radical can be for example a heteroaromatic radical or ring (heteroaryl), such as, for example, a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more hetero atoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or it is a partially or fully hydrogenated radical such as oxiranyl, oxetanyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydro- furyl.
  • heteroaryl such as, for example, a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more hetero atoms, for example pyri
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned further below, and additionally also oxo.
  • the oxo group can also be present at those hetero ring atoms which may exist at various levels of oxidation, for example in the case of N and S.
  • Halogen is, for example, fluorine, chlorine, bromine or iodine.
  • Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl or alkynyl which is partially or fully substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example CF 3 , CHF 2 , CH 2 F, CF 3 CF 2 , CH 2 FCHCl, CCl 3 , CHCl 2 , CH 2 CH 2 Cl;
  • haloalkoxyl is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 Cl; this also applies analogously to haloalkenyl and other halogen-substituted radicals.
  • Hydrocarbon radicals for example alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or heterocyclyl or heteroaryl can be substituted, the substituents meaning, for example, one or more, preferably 1 , 2 or 3, radicals from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkyl- -aminocarbonyl, substituted amino such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals, also alkyl and haloalkyl and unsaturated
  • substituents are, as a rule, those from the group consisting of halogen, for example fluorine and chlorine, (C r C 4 )alkyl, preferably methyl or ethyl, (C r C 4 )haloalkyl, preferably trifluoromethyl, (Ci-C 4 )alkoxy, preferably methoxy or ethoxy, (Ci-C 4 )haloalkoxy, nitro and cyano.
  • substituents methyl, methoxy and chlorine.
  • Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubsti- tuted, preferably up to trisubstituted, by identical or different radicals from the group consisting of halogen, (Ci-C 4 )alkyl, (C)-C 4 )alkoxy, (Ci-C 4 )halogenoalkyl, (C r C 4 )halogenoalkoxy and nitro, for example o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4- chlorophenyl, 2-, 3- and 4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2, 5- and 2,3-dichlorophenyl, o-, m- and p- methoxyphenyl.
  • An acyl radical means the radical of an organic acid which is formed formally by eliminating an OH group from the organic acid, for example a carboxylic acid radical and radicals of acids derived from it such as thiocarboxylic acid, optionally N-substituted iminocarboxylic acids or the radicals of carbonic monoesters, optionally N-substituted carbamic acids, sulfonic acids, sulfinic acids, phosphonic acids and phosphinic acids.
  • An acyl radical is preferably fo ⁇ nyl or aliphatic acyl from the group consisting of CO-R X , CS-R X , CO-OR", CS-OR", CS-SR", SOR Y or SO 2 R Y , where R" and R ⁇ in each case denotes a C 1 -C 30 - hydrocarbon radical which is unsubstituted or substituted, or aminocarbonyl or aminosulfonyl, the two last-mentioned radicals being unsubstituted, N-monosubstituted or N,N-disubstituted.
  • Acyl is, for example, formyl, halogenoalkylcarbonyl, alkylcarbonyl such as (Ci-C 4 )alkylcarbonyl, phenylcarbonyl, it being possible for the phenyl ring to be substituted, for example as stated above for phenyl, or alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N- alkyl- 1-iminoalkyl and other radicals of organic acids.
  • the formula (I) and the other compounds mentioned in the present description also encompass all of the stereoisomers and their mixtures.
  • Such compounds contain one or more asymmetric carbon atoms or else double bonds which are not mentioned specifically in the general formula.
  • the possible stereoisomers which are defined by their specific spatial shape, such as enantiomers, diastereomers, Z- and E-isomers, are all encompassed by the respective formulae and can be obtained from mixtures of the stereoisomers by customary methods or else be prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.
  • microemulsion concentrates according to the invention can be prepared by customary methods, for example mixing by dissolving or emulsifying the individual components, preferably at room temperature. If further auxiliaries and additives are present, they are likewise preferably introduced at room temperature. In general, the individual components can be added in any desired sequence.
  • the formulation auxiliaries such as inert materials and further additives, are likewise known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed.,
  • agrochemical active ingredients other than component a such as herbicides, fungicides, insecticides, safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or a tank mix.
  • microemulsion concentrates according to the invention can be diluted with water to give micro- emulsions which are likewise subject matter of the present invention.
  • the weight ratio microemulsion concentrate:water can be, for example, 1 :0.1 to 1 :100, preferably 1 : 1 to 1 :100, which gives concentrated microemulsions which, per se, are storage stable.
  • they can be diluted further with water to give spray mixtures which are generally present in the form of emulsions such as microemulsions, aqueous solutions, suspensions or suspoemulsions.
  • microemulsion concentrates and microemulsions according to the invention may be present together in a ready mix which can then be applied in the customary manner, for example in the form of a spray mixture.
  • microemulsion concentrates and microemulsions according to the invention including the spray mixtures which can be obtained from them
  • auxiliaries such as anti-drift agents, humectants, fertilizers such as ammonium sulfate, urea or compound fertilizers, for example on a phosphorus, potassium and nitrogen basis, such as P,K,N fertilizers, or commercially available surfactants other than components c) and d), such as betainic or polymeric surfactants, stabilizers such as pH stabilizers, biocides, UV stabilizers, antifoams, synthetic or natural polymers, solvents, for example polar solvents such as water or unpolar solvents such as saturated or unsaturated aliphatic solvents which can be branched or unbranched, or aromatic solvents such as Solvesso®100, Solvesso®150 or Solvesso®) 200 or xylene.
  • formulation auxiliaries such as anti-drift agents, humectants, fertilizers such as ammonium sulfate, urea or compound fertilizers, for example on a phosphorus, potassium and nitrogen basis, such
  • wetters such as Genapol® LRO (0-20% by weight), dispersants such as Tamol® (0-15% by weight) or further surfactants (nonionic, cationic, anionic, polymeric surfactants) (0-30% by weight);
  • inorganic salts such as NaCl, Na 2 SC ⁇ , MgCl 2 (0-50% by weight), (oligo-, poly-) phosphates; carbonates such as potassium carbonate;
  • fertilizers such as ammonium sulfate, ammonium nitrate, urea, phosphorus- and potassium- containing components, if appropriate further trace elements (0-60% by weight);
  • antifoams such as Fluowet® PP (0-2% by weight);
  • binders such as suitable natural or synthetic substances such as polyamino acids, polyvinyl alcohols, polyvinylpyrrolidone, polyacrylic acid derivatives, (0-15% by weight); or
  • the agrochemical compositions according to the invention can be employed for example by application to the harmful organisms or the locations where they occur, for example by spraying.
  • the agrochemical compositions according to the invention are applied in the form of a spray mixture which comprises the components a), b), c) and d) in effective amounts and, if appropriate, further customary auxiliaries and additives, for example for formulation or use.
  • the spray mixture is prepared on the basis of water, it being possible to add customary auxiliaries and additives, for example oils, such as vegetable oils, or high-boiling hydrocarbons, such as kerosene or paraffin.
  • the concentration of agrochemical active ingredient a) is generally 10 "6 to 10% by weight, preferably 10 "5 to 4% by weight in the applied composition, for example the spray mixture, at an application rate of 1 to 5 000 1/ha, preferably 50 to 1 000 1/ha.
  • concentrated formulations which are present in commercially available form are, if appropriate, diluted in the customary manner, for example by means of water. It may be advantageous to add further amounts of components b), c) and d) and/or other conventional auxiliaries and additives for use, in particular self-emulsifying oils or paraffin oils, to the spray mixtures. Additional components a) or other agrochemical active ingredients other than component a) may also be added.
  • the application rate required of the agrochemical active ingredients a) can vary with the external condi- tions such as temperature, humidity, type of herbicide used. It can vary within wide limits, for example between 0. 001 and 10 kg/ha or more active substance; it is preferably between 0.005 and 5 kg/ha.
  • the agrochemical compositions according to the invention are preferably insecticidal compositions. They have an outstanding insecticidal activity against a broad spectrum of economically important insects.
  • the active compounds are suitable for protecting plants and plant organs, for increasing the harvest yields, for improving the quality of the harvested material and for controlling animal pests, in particular insects, arachnids and nematodes, which are encountered in agriculture, in forests, in gardens and leisure facilities, in the protection of stored products and of materials, and in the hygiene sector, and have good plant tolerance and favourable toxicity to warm-blooded animals and are tolerated well by the environment.
  • animal pests in particular insects, arachnids and nematodes, which are encountered in agriculture, in forests, in gardens and leisure facilities, in the protection of stored products and of materials, and in the hygiene sector, and have good plant tolerance and favourable toxicity to warm-blooded animals and are tolerated well by the environment.
  • They may be preferably employed as plant protection agents. They are active against normally sensitive and resistance species and against all or some stages of development.
  • the abovementioned pests include: - -
  • Anoplura e.g. Damalinia spp., Haematopi ⁇ us spp., Linognathus spp., Pediculus spp., Trichodectes spp.
  • Arachnida e.g. Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Omithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotar- sonemus la
  • Gastropoda e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
  • Ancylostoma duodenale From the order of the Helminths e.g. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus
  • Isopoda e.g. Armadillidium vulgare, Oniscus asellus, Porcellio scaber.
  • Isoptera e.g. Reticulite ⁇ nes spp.
  • Odontotermes spp From the order of the Lepidoptera e.g.
  • Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
  • compositions according to the invention in economically important transgenic crops of useful plants and ornamentals, such as of Gramineae crops such as wheat, barley, rye, oats, sorghum and millet, rice and maize or else crops of sugar beet, cotton, soybean, oilseed rape, potato, tomato, pea and other vegetables is also possible.
  • the compositions according to the invention may preferably be employed as herbicides in crops of useful plants which are resistant to the phytotoxic effects of the herbicides or which have been rendered resistant to the phytotoxic effects of the herbicides by recombinant means.
  • the crops of plants can also have been genetically modified or obtained by the selection of mutants.
  • agrochemical compositions in particular insecticidal compositions, according to the invention may, if appropriate, be present in the fo ⁇ n of mixed formulations together with further agrochemical active ingredients and customary auxiliaries and additives, and these mixed formulations are then applied in the customary manner as a dilution with water, or else be prepared in the form of what are known as tank mixes by jointly diluting the separately formulated, or partially separately formulated, components with water.
  • insecticidal compositions according to the invention can be applied in the customary manner, for example with water as carrier in spray mixture rates of approximately 5 to 4 000 liters/ha. Likewise the compositions can be applied by what are known as the low-volume and ultra-low-volume methods (ULV).
  • UUV ultra-low-volume methods
  • insecticidal compositions of the invention may also comprise one, two or more agrochemical active ingredients other than the insecticides a) (for example herbicids, fungicides), usually in minor amounts, in order to complement the property profile.
  • agrochemical active ingredients other than the insecticides a) (for example herbicids, fungicides), usually in minor amounts, in order to complement the property profile.
  • microemulsion concentrates according to the invention give stable microemulsions upon dilution with water without the use of alcoholic solvent.
  • microemulsion concentrates and microemulsions according to the invention show an advantageous physical application behavior.
  • the agrochemical active ingredient remains uniformly distributed in the spray tank, making possible a uniform application to the crop or area under cultivation.
  • Even mixtures formed in the spray tank ,(tank mixes) such as aqueous solutions, suspensions, emulsions or suspoemulsions are stable.
  • the agrochemical compositions according to the invention have an outstanding biological activity and preferably act synergistically. These effects pe ⁇ nit, inter alia, the application rate to be reduced, a broader spectrum of harmful organisms to be controlled, gaps in the control to be overcome, a more rapid and reliable activity, an extended long-term activity, complete control of the harmful organisms with only one or few applications, and the application window to be widened.

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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 des micro-émulsions ou des concentrats de celle-ci comprenant (a) du fipronil et éventuellement une ou plusieurs substances actives insecticides en plus du fipronil, (b) un ou plusieurs solvants organiques non alcooliques, (c) un ou plusieurs tensioactifs non ioniques. Ces micro-émulsions ou ces concentrats de micro-émulsion conviennent dans le domaine de la protection des récoltes.
PCT/EP2006/006904 2005-07-27 2006-07-14 Micro-emulsions WO2007017040A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
MX2008001116A MX2008001116A (es) 2005-07-27 2006-07-14 Microemulsiones y concentrados que contienen fipronil.
JP2008523177A JP2009502826A (ja) 2005-07-27 2006-07-14 フィプロニルを含んでいるマイクロエマルション及び濃厚物
EP06754725A EP1912505A2 (fr) 2005-07-27 2006-07-14 Microemulsions et concentres contenant du fipronil
BRPI0613908-6A BRPI0613908A2 (pt) 2005-07-27 2006-07-14 microemulsões

Applications Claiming Priority (2)

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CN200510087934.4 2005-07-27
CNA2005100879344A CN1903029A (zh) 2005-07-27 2005-07-27 微乳剂

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WO2007017040A2 true WO2007017040A2 (fr) 2007-02-15
WO2007017040A3 WO2007017040A3 (fr) 2007-12-06

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EP (1) EP1912505A2 (fr)
JP (1) JP2009502826A (fr)
KR (1) KR20080032225A (fr)
CN (1) CN1903029A (fr)
BR (1) BRPI0613908A2 (fr)
MX (1) MX2008001116A (fr)
WO (1) WO2007017040A2 (fr)
ZA (1) ZA200800676B (fr)

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WO2008129060A2 (fr) * 2007-04-23 2008-10-30 Basf Se Augmentation de la productivité d'une plante par combinaison d'agents chimiques avec des modifications transgéniques
US20100159400A1 (en) * 2008-12-24 2010-06-24 Samsung Electronics Co., Ltd. Composition for removing a photoresist pattern and method of forming a metal pattern using the composition
US8367583B2 (en) 2009-05-25 2013-02-05 Sumitomo Chemical Company, Limited Composition and method for controlling pests

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CN100433979C (zh) * 2007-01-18 2008-11-19 江苏太湖地区农业科学研究所 含氟虫腈和异丙威的杀虫组合物
BR112013024184A2 (pt) * 2011-03-23 2017-03-28 Makhteshim Chem Works Ltd método para controlar insetos agrícolas em uma cultura, uso de uma composição, composição e kit
CN102428913B (zh) * 2011-11-11 2014-01-22 山东一览科技有限公司 一种微乳剂杀虫剂及其生产工艺
GB201707930D0 (en) * 2017-05-17 2017-06-28 Syngenta Participations Ag Formulation component
CN109169644A (zh) * 2018-09-07 2019-01-11 东北农业大学 一种艾蒿微乳剂及其制备方法

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WO2004054360A2 (fr) * 2002-12-17 2004-07-01 Bayer Cropscience Gmbh Concentres de microemulsion
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008129060A2 (fr) * 2007-04-23 2008-10-30 Basf Se Augmentation de la productivité d'une plante par combinaison d'agents chimiques avec des modifications transgéniques
WO2008129060A3 (fr) * 2007-04-23 2009-02-19 Basf Se Augmentation de la productivité d'une plante par combinaison d'agents chimiques avec des modifications transgéniques
EP2392662A3 (fr) * 2007-04-23 2012-03-14 Basf Se Amélioration de la productivité des plantes en combinant les agents chimiques avec des modifications transgéniques
EA017621B1 (ru) * 2007-04-23 2013-01-30 Басф Се Повышение продуктивности растений путем комбинирования химических веществ с трансгенными модификациями
US20100159400A1 (en) * 2008-12-24 2010-06-24 Samsung Electronics Co., Ltd. Composition for removing a photoresist pattern and method of forming a metal pattern using the composition
US8367583B2 (en) 2009-05-25 2013-02-05 Sumitomo Chemical Company, Limited Composition and method for controlling pests

Also Published As

Publication number Publication date
KR20080032225A (ko) 2008-04-14
EP1912505A2 (fr) 2008-04-23
ZA200800676B (en) 2009-05-27
WO2007017040A3 (fr) 2007-12-06
MX2008001116A (es) 2008-03-13
BRPI0613908A2 (pt) 2011-02-15
CN1903029A (zh) 2007-01-31
JP2009502826A (ja) 2009-01-29

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