EP3772944A1 - Suspensionskonzentrate auf ölbasis - Google Patents

Suspensionskonzentrate auf ölbasis

Info

Publication number
EP3772944A1
EP3772944A1 EP19716433.8A EP19716433A EP3772944A1 EP 3772944 A1 EP3772944 A1 EP 3772944A1 EP 19716433 A EP19716433 A EP 19716433A EP 3772944 A1 EP3772944 A1 EP 3772944A1
Authority
EP
European Patent Office
Prior art keywords
spp
oil
formula
suspension concentrates
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19716433.8A
Other languages
German (de)
English (en)
French (fr)
Inventor
Reiner Fischer
Oliver Gaertzen
Leonardo Pitta
Rolf Pontzen
Udo Reckmann
Arnoldus VERMEER
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP3772944A1 publication Critical patent/EP3772944A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A01N25/08—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 solids as carriers or diluents
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • 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
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • 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
    • A01N25/30—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 characterised by the surfactants
    • 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
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to novel, oil-based suspension concentrates of cyclic ketoenols, to a process for the preparation of these formulations and to their use for the application of the cyclic ketoenols present for controlling animal pests.
  • systemic agrochemically active compounds particularly systemic insecticides, require a formulation for the development of the biological activity which allows the active substances to be incorporated into the plant / target organisms. Therefore, systemic agrochemically active compounds are usually formulated as emulsion concentrate (EC), liquid liquid (SL) and / or adjuvanted suspension concentrate (SC) or oil-based suspension concentrate (OD).
  • EC and SL formulation the active ingredient is in dissolved form, in a SC and OD formulation as a solid. While the active ingredient in dissolved form meets the best conditions for uptake into the plant or the target organisms, the biological effect is increased in adjuvanted SC and OD formulations by the addition of penetration promoters.
  • adjuvants which improve the properties (retention, spreading behavior, rainfastness, etc.) are usually incorporated into the formulation.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself exhibiting a biological effect.
  • Adjuvants in general and penetrants in particular are surfactants which can come from different chemical classes (e.g., alkanol ethoxylates, amino ethoxylates, or esters of vegetable oils (e.g., MSO)).
  • oils to improve the effectiveness of pesticides by improving the wetting and spreading properties of the spray residues are described.
  • oils are mineral oils, vegetable oils and esters of these vegetable oils. It is known that vegetable oil esters improve the uptake of many pesticides into the leaf and that e.g. the very low volatility of vegetable oils increases the residual effectiveness of crop protection products.
  • EP-A 0 789 999 describes formulations of this type which, in addition to active ingredient and oil, contain a mixture of various surfactants, including those which serve as penetration promoters, and a hydrophobized alumino-layer silicate as thickener. The stability of these preparations is good.
  • oil-based suspension concentrates are known from US Pat. No. 6,165,940, in which, apart from the agrochemical active ingredient, penetration promoter and surfactant or surfactant mixture, an organic solvent is present, parafin oil or vegetable oil esters being suitable as such solvents. Crop compatibility and / or however, biological effectiveness and / or the stability of spray liquors prepared from these formulations by dilution with water is not always sufficient.
  • WO 05/084435 and WO 05/08441 describe oil-based suspension concentrates which, in addition to cyclic ketoenols and oil, contain a penetration promoter.
  • US Pat. No. 6,423,667 discloses oil-based suspension concentrates comprising ammonium sulfate and a nonionic surfactant which are used as herbicidal auxiliaries or as herbicidal compositions.
  • ammonium salts there is another group of adjuvants, that of ammonium salts.
  • ammonium ions enter into the formulations because the active ingredients used are used as ammonium salts, as is customary in particular with the widely used herbicide glyphosate (eg WO 07/050090, WO 05/117583, WO 05 / 013692, WO 06/050141, US 2003/104947, US 5,238,604, DE-A-197 52 552).
  • a separate ammonium salt is added. It has already been described in the literature that the effect of various active substances can be increased by adding ammonium salts.
  • salts acting as detergent eg WO 95/017817
  • salts with longer alkyl and / or aryl substituents which have a permeabilizing effect or increase the solubility of the active ingredient
  • the prior art describes the effect only for certain active ingredients and / or certain applications of the corresponding agents.
  • salts of sulfonic acids in which the acids themselves paralyzing effect on insects (US 2,842,476).
  • An increase in activity e.g. by ammonium sulfate, for example, for the herbicides glyphosate and phosphinothricin described (US 6,645,914, EP-A 0 036 106).
  • ammonium sulfate as a formulation aid is described for certain active ingredients and applications (WO 92/16108), but it is there to stabilize the formulation, not to increase the effect.
  • tank-mix compositions of cyclic ketoenols with ammonium salts to increase the potency of e.g. in WO 07/068427, WO 07/068428 and WO 08/067911.
  • the described adjuvants can be incorporated into the formulation of the agrochemical active ingredient (in-can formulation) or added after diluting the concentrated formulation of the spray mixture (tank mix). To avoid dosage errors and to improve the safety of users in the application of agrochemical products, it is advantageous to incorporate the additives in the formulation. Furthermore, this avoids the unnecessary use of additional packaging material for the tank mix products.
  • the compositions described above contain either an oil / penetrable system or an ammonium salt to increase the biological effect. However, the combination of both adjuvants in an "in-can" formulation containing agrochemical agents has not yet been described.
  • oils as intake enhancers in combination with ammonium salts for agrochemical compositions, possibly mixed with other uptake promoting surfactants, would be a logical alternative.
  • the literature mostly discloses only adjuvant compositions containing either oil (s) or ammonium salts.
  • oil (s) or ammonium salts One of the difficulties in developing such formulations is the form of the ammonium salt.
  • the ammonium salts are in the dissolved form resulting in a homogeneous liquid formulation.
  • the solubility of the appropriate ammonium salts is significantly less than the amount of salt necessary to increase the potency.
  • ammonium salt in the oil-based formulations will be in crystalline form, causing formulation problems.
  • the common ammonium salts are difficult to crush because of their hardness.
  • ammonium salt-containing oil-based formulations tend to have high viscosities after comminution and are generally difficult to stabilize in oil-based suspension concentrates.
  • the object therefore was to provide stable, storage-stable, liquid agrochemical compositions which contain at least one oil which is suitable for improving the action of cyclic ketoenols and a suitable ammonium salt with a small particle size distribution in a sufficient amount, and which Active ingredient either in the concentrate and / or in aqueous dilution in dissolved form provides.
  • this object is achieved by the specific composition of the present invention.
  • the present invention thus relates to oil-based agrochemical compositions containing at least one compound of formula (I) which is solid at room temperature.
  • W and Y are independently hydrogen, C
  • X is Ct-C ⁇ alkyl, C
  • D represents hydrogen or methyl
  • A, B and the carbon atom to which they are bonded represent Ü ⁇ -CG-cycloalkyl, optionally one ring member is replaced by nitrogen in which and which is optionally monosubstituted t by Ci-C -alkoxy is or
  • A, B and the carbon atom to which they are bonded represent Ü ⁇ -CG-cycloalkyl which is optionally substituted by by a C
  • - is substituted (' [ -alkyl or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl-substituted alkylenedioxy group which forms a 5-membered or 6-membered ketal with the carbon atom to which it is attached,
  • G is hydrogen (a) or one of the groups
  • E stands for a metal ion or an ammonium ion
  • M is oxygen or sulfur
  • R 1 is straight-chain or branched C 1 -C 8 -alkyl, represents straight-chain or branched C 1 -C 8 -alkyl and at least one suspended ammonium salt of the formula (1)
  • R 1 , R 2 , R 3 and R 4 are each independently hydrogen or each optionally mono- or polysubstituted Cj-Cs-alkyl or Cj-Cs-alkylene, wherein the substituents can be selected from halogen, nitro and cyano, n is 1, 2 or 3, R 5 is hydrogen carbonate, tetraborate, fluoride, bromide, iodide, chloride,
  • the number n in the formula (1) results from the ionic charge of the substituent R 5 .
  • Oil-based composition means that the compositions according to the invention are substantially free of water.
  • the water content is preferably less than 1.5% by weight, more preferably less than 0.7% by weight. Because of the low water content, the ammonium salt of the formula (1) is suspended in the compositions according to the invention.
  • the present invention further relates to processes for the preparation of these agrochemical compositions and their use for improving the action of crop protection agents.
  • oil-based agrochemical compositions according to the invention can be prepared by reacting at least one compound of the formula (I) which is solid at room temperature, at least one ammonium salt of the formula (I), at least one mineral oil, vegetable oil, fatty acid triglyceride or fatty acid alkyl ester, at least a non-ionic surfactant and / or at least one anionic surfactant, optionally a receiving promoter, and optionally one or more additives from the groups of spreading agents, the foam-inhibiting agent, the antioxidants, the dyes and / or the thickener mixed together and the resulting suspension optionally then grinds.
  • oil-based suspension concentrates according to the invention are very well suited for the application of the compounds of the formula (I) to plants and / or their dream habitat. Furthermore, it has been found that the oil-based suspension concentrates according to the invention are very suitable for controlling animal pests.
  • oil-based agrochemical compositions according to the invention have a low viscosity and a very good stability, and in particular that no significant crystal growth of the active ingredient and / or the ammonium salt is observed even after aging at alternating temperature. It is also unexpected that they show significantly better biological effectiveness than the spray mixture composed by means of a tank mixture. Incidentally, the oil-based agrochemical compositions according to the invention surprisingly also exceed in their activity analogous preparations which, in addition to the other components, contain either only one ammonium salt or only one oil. Such a synergistic effect was unpredictable due to the above-described prior art.
  • the oil-based agrochemical compositions of the invention are also characterized by a number of other advantages.
  • the number of necessary "tank-mix” components is reduced because several properties to be optimized are combined in the liquid agrochemical compositions of the invention.
  • the user therefore needs his Do not mix active ingredients with other mixing components in the spray mixture.
  • This has the advantage of avoiding dosage errors and increasing the safety of users in the application of agrochemicals.
  • this avoids the use of packaging material for several "tank-mix” products.
  • a further advantage is that when diluting the liquid agrochemical compositions according to the invention with water, the pH of the spray mixture can be controlled by the choice of the ammonium salt in the product.
  • oil-based agrochemical compositions according to the invention promote the biological activity of the active components of the formula (I) in the formulation, so that either a higher efficacy or less active ingredient is required compared to conventional preparations.
  • preferred embodiments of the subject invention will be described.
  • W is particularly preferably methyl
  • X is particularly preferably chlorine or methyl (highlighted for methyl),
  • Y is particularly preferably chlorine, bromine or methyl
  • D is particularly preferably hydrogen
  • A, B and the carbon atom to which they are attached are particularly preferably saturated
  • G is particularly preferably hydrogen (a) or one of the groups in which
  • E is a metal ion equivalent or an ammonium ion (highlighted for sodium or potassium)
  • R 1 particularly preferably represents straight-chain or branched C 1 -C 4 -alkyl, particularly preferably represents straight-chain or branched C
  • -.. ( '(Alkyl Featured preferred are the compounds of formula (I) where G hydrogen.
  • optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
  • Ammonium salts according to the invention are defined by formula (1)
  • R 1 , R 2 , R 3 and R 4 are each independently hydrogen or each optionally mono- or polysubstituted Cj-Cs-alkyl or Cj-Cs-alkylene, where the substituents can be selected from halogen, nitro and cyano .
  • R 1 , R 2 , R 3 and R 4 preferably independently of one another represent hydrogen or in each case optionally monosubstituted C 1 -C 4 -alkyl, where the substituents can be selected from halogen, nitro and cyano,
  • R 1 , R 2 , R 3 and R 4 more preferably independently of one another are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl,
  • R 1 , R 2 , R 3 and R 4 most preferably represent hydrogen
  • R 1 , R 2 , R 3 and R 4 furthermore very particularly preferably simultaneously represent methyl or simultaneously represent ethyl, n represents 1, 2 or 3, n preferably represents 1 or 2,
  • Dihydrogen phosphate hydrogen sulfate, tartrate, sulfate, nitrate, thiosulfate, thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoate, citrate, oxalate, carbonate, pentaborate, sulfite,
  • R 5 is preferably lactate, sulphate, nitrate, thiosulphate, thiocyanate, citrate, oxalate, formate, monohydrogenphosphate or dihydrogenphosphate, R 5 is particularly preferred for sulfate, monohydrogen phosphate or dihydrogen phosphate.
  • Preferred salts are ammonium hydrogencarbonate, ammonium tetraborate, ammonium fluoride, ammonium bromide, ammonium iodide, ammonium chloride, diammonium monohydrogenphosphate, ammonium dihydrogenphosphate, ammonium hydrogensulfate, ammonium tartrate, ammonium sulfate, ammonium nitrate, ammonium thiosulfate, ammonium thiocyanate, ammonium formate, ammonium lactate, ammonium acetate, ammonium propionate, ammonium butyrate, ammonium carbonate.
  • Ammonium benzoate ammonium hydrogen oxalate, ammonium hydrogen citrate, ammonium methyl sulfate or ammonium tetrafluoroborate.
  • Particularly preferred salts are diammonium monohydrogenphosphate,
  • Ammonium dihydrogen phosphate ammonium sulfate, ammonium nitrate, ammonium thiosulfate, ammonium thiocyanate, ammonium formate, ammonium lactate, ammonium citrate or ammonium oxalate.
  • Particularly preferred salts are diammonium monohydrogenphosphate,
  • Diammonium monohydrogen phosphate diammonium hydrogen phosphate
  • ammonium sulfate diammonium phosphate
  • the vegetable oils contained in the adjuvant compositions of the present invention are well known and commercially available.
  • the term vegetable oils or fatty acid triglycerides for example oils from ölellenden plant species such as soybean oil, rapeseed oil, corn oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, thistle oil, walnut oil, peanut oil, olive oil, castor oil, rapeseed oil, palm kernel oil, coconut oil and especially soybean oil , Rapeseed oil, corn oil or sunflower oil and mixtures thereof.
  • suitable triglycerides can be synthesized by known methods by reaction of glycerol with fatty acids or fatty acid derivatives.
  • Triglycerides of this type are also well known and commercially available.
  • the vegetable oils or triglycerides are preferably esters of C 8 -C 22 fatty acids of glycerol.
  • the C 8 -C 22 -Fettklarenester of glycerol are, for example, esters of unsaturated or saturated C 8 -C 2 o-fatty acids, especially with an even number of carbon atoms, for example caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, erucic acid and in particular Cis-fatty acid such as stearic acid, Oleic acid, linoleic acid or linolenic acid.
  • Emphasis should be given to caprylic acid / capric acid triglyceride ester (Mitlyol 812 N® (Sasol, Germany)).
  • Suitable mineral oils are various commercially available distillation fractions of petroleum and paraffin oils. Preference is given to mixtures of open-chain C 14 -C 30 hydrocarbons, closed-chain hydrocarbons (naphthenes) and aromatic hydrocarbons.
  • the hydrocarbons can be both linear and branched. Particular preference is given to mixtures which have an aromatic fraction of less than 8% by weight. All Particular preference is given to mixtures which have an aromatic fraction of less than 4% by weight.
  • paraffin oils are linear and branched Ci4-C3o-hydrocarbons in question.
  • Paraffin oils are also known as base oil or white oil and are commercially available as Bayol® 85 (Exxon Mobil, Machelen, Belgium), Marcol® 82 (Exxon Mobil, Machelen, Belgium), BAR 0020 (RA.M.oil SpA, Naples, Italy ), Pioneer 0032-20 (Hansen & Rosenthal KG, Hamburg, Germany) or eg Kristol M14 (Carless, Surrey, England).
  • Suitable fatty acid esters are alkyl fatty acid esters such as C 1 -C 20 -alkyl-C 10 -C 22 -fatty acid esters. Preference is given to methyl esters, ethyl esters, propyl esters, butyl esters, 2-ethylhexyl esters and dodecyl esters. Particularly preferred are methyl esters and ethyl esters.
  • Examples of synthetic fatty acid esters are e.g. those derived from odd carbon number fatty acids, such as C11-C21 fatty acid esters.
  • the production of said fatty acid esters e.g. by transesterification can be carried out by known methods, such. described in Römpp Chemie Fexikon, 9th edition, volume 2, page 1343, Thieme Verlag, Stuttgart.
  • the fatty acid esters may be included in the adjuvant compositions of the invention in the form of commercially available esters, especially esters such as rapeseed oil methyl ester, e.g. Edenor® MESU (Cognis, Germany) or the Agnique® ME series (Cognis, Germany) or in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil methyl or ethyl ester, e.g. Hasten® (Victoria Chemicals, Australia), Actirob® B (Novance, France) or Stefes Mero® (Stefes, Germany). Highlighted is rapeseed oil methyl ester.
  • esters such as rapeseed oil methyl ester, e.g. Edenor® MESU (Cognis, Germany) or the Agnique® ME series (Cognis, Germany) or in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil methyl or
  • rapeseed oil methyl ester and caprylic acid / capric acid triglyceride ester are particularly noteworthy.
  • Suitable nonionic surfactants or dispersing agents are all substances of this type which can usually be used in agrochemical compositions.
  • reaction products of linear or branched alcohols with ethylene oxide and / or propylene oxide reaction products of fatty acids with ethylene oxide and / or propylene oxide, reaction products of alkylphenols and / or arylalkylphenols with ethylene oxide and / or propylene oxide such as ethoxylated nonylphenols, as well as sorbitan derivatives such as Sorbitan fatty acid esters and ethoxylated sorbitan fatty acid esters, also alkylpolyglycosides, taurides, as well as ethoxylated vegetable oils such as ethoxylated soybean oil, furthermore castor oil ethoxylates.
  • polyethylene oxide-polypropylene oxide block copolymers polyvinyl alcohol, polyvinylpyrrolidone, copolymers of polyvinyl alcohol and polyvinylpyrrolidone and copolymers of (meth) acrylic acid and (meth) acrylic acid esters.
  • Some of the above classes of substances may optionally be sulfated or phosphated and neutralized with bases.
  • ethoxylated vegetable oils and castor oils phosphated and neutralized alkyl ethoxylates, ethoxylated sorbitan fatty acid esters.
  • Suitable anionic surfactants or dispersants are all substances of this type which can usually be used in agrochemical compositions. Preference is given to alkali metal, alkaline earth metal and ammonium salts of alkylsulfonic acids, alkylarylsulfonic acids, alkyl sulfates or alkylaryl sulfates.
  • alkali metal, alkaline earth metal and ammonium salts of sulfated or phosphated Alkylphenolethoxylaten or ethoxypropoxylaten such as calcium dodecylbenzenesulfonate / CaDBS, Arylalkylphenolethoxylaten or ethoxy-propoxylates or linear or branched alcohol ethoxylates or ethoxypropoxylates.
  • salts of polystyrenesulfonic acids salts of polyvinylsulfonic acids, salts of maleic acid 2,4,4-trimethylpentenes copolymers such as Geropon T36, salts of naphthalenesulfonic acid-formaldehyde condensation products such as Morwet D-425, salts of condensation products of naphthalenesulfonic acid, Phenolsulfonic acid and formaldehyde, and salts of lignosulfonic acids.
  • Receiving conveyors are in this context defined by the fact that they can penetrate from the aqueous spray mixture and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of active ingredients in the cuticle.
  • the method described subsequently and in the literature can be used to determine this property.
  • Suitable absorption enhancers are, for example, alkanol alkoxylates.
  • Receiving promoters according to the invention are alkanol alkoxylates of the formula
  • R is straight-chain or branched alkyl having 4 to 20 carbon atoms
  • R is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl or n-hexyl,
  • AO stands for an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical or mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals and m stands for numbers from 2 to 30.
  • a preferred group of uptake promoters are alkanol alkoxylates of the formula R-0 - (- EO-) b -R '(Pa) in which R has the meaning given above,
  • EO is -CH 2 -CH 2 -O- and b is a number from 2 to 20.
  • alkanol alkoxylates of the formula R-0 - (- E0-) p - (- P0-) q -R '(Pb), and
  • R ' has the meaning given above, EO is -CH 2 -CH 2 -O-,
  • CH 3 p is a number from 1 to 10 and q is a number from 1 to 10.
  • alkanol alkoxylates of the formula R-O - (- EO-) v - (- B0-) x -R '(II-d), and
  • EO is CH 2 -CH 2 -O-
  • BO stands for v represents numbers from 1 to 10 and x represents numbers from 1 to 10.
  • R is preferably butyl, i-butyl, n-pentyl, i-pentyl, neopentyl, n-hexyl, i-hexyl, n-octyl, i-octyl, 2-ethyl-hexyl, nonyl, i-nonyl, decyl, n Dodecyl, i-dodecyl, lauryl, myristyl, i-tridecyl, trimethyl-nonyl, palmityl, stearyl or eicosyl.
  • alkanol alkoxylates are generally defined by the above formulas. These substances are mixtures of substances of the specified type with different chain lengths. For the indices, therefore, average values are calculated, which can also differ from whole numbers.
  • alkanol alkoxylates of the formulas given are known and are partly commercially available or can be prepared by known methods (cf., WO 98-35553, WO 00-35278 and EP-A 0 681 865).
  • Suitable spreading agents are all substances customarily usable for this purpose in agrochemical compositions. Preference is given to alkylsiloxanes.
  • Suitable foam-inhibiting substances are all substances customarily usable for this purpose in agrochemical compositions.
  • Preferred are silicone oils and magnesium stearate.
  • antioxidants are all commonly used for this purpose in agrochemical agents substances into consideration. Preference is given to 2,6-di-tert-butyl-4-methylphenol.
  • Suitable dyes are all substances customarily usable for this purpose in agrochemical compositions. Examples include titanium dioxide, carbon black, zinc oxide and blue pigments as well as permanent red FGR.
  • Suitable thickeners are all substances which can usually be used for this purpose in agrochemical compositions and which act as thickeners. Preference is given to inorganic particles, such as carbonates, silicates and oxides, and also talc, and also organic substances, such as urea Formaldehyde condensates. Kaolin, rutile, silicon dioxide, so-called highly disperse silica, silica gels, as well as natural and synthetic silicates such as attapulgites, bentonites, seipiolites, or montmorillites, as well as organomodified derivatives thereof, may be mentioned by way of example.
  • compositions comprising a) from 0.5 to 20% by weight of the compound of the formula (I) b) from 5 to 35% by weight of ammonium salt of the formula (1) c) from 20 to 75% by weight of the oil d) 1 - 25% by weight of nonionic surfactant and / or anionic surfactant e) 0-25% by weight of receiving promoter f) 0-10% by weight of one or more additives from the groups of foam-inhibiting agents, antioxidants, spreading agents , the dyes and / or a thickener.
  • compositions comprising a) 1 to 15% by weight of the compound of the formula (I) b) 15-30% by weight of ammonium salt of the formula (1) c) 35 to 65% by weight of oil d) 5 20% by weight of nonionic surfactant and / or anionic surfactant e) 0-20% by weight of receiving promoter f) 0-8% by weight of one or more additives from the groups of foam-inhibiting agents, antioxidants, spreading agents, the dyes and / or a thickener.
  • the preparation of the oil-based agrochemical compositions according to the invention is carried out by mixing the components together in the ratios desired in each case.
  • the order in which the ingredients are mixed together is arbitrary. Conveniently, one uses the solid components in a finely ground state. However, it is also possible to first subject the suspension resulting from the mixing of the constituents to a coarse and then to a fine grinding so that the average particle size is below 20 ⁇ m lies. Preference is given to suspension concentrates in which the solid particles have an average particle size between 1 and 10 ⁇ m.
  • the temperatures can be varied in carrying out the method according to the invention in a certain range. It generally works at temperatures between 10 ° C and 60 ° C, preferably between 15 ° C and 40 ° C.
  • customary mixing and grinding devices which are used for the production of agrochemical formulations are suitable.
  • oil-based agrochemical compositions according to the invention are formulations which remain stable even after prolonged storage at elevated temperatures or in the cold, since no crystal growth is observed. They can be converted by dilution with water into homogeneous spray liquids.
  • the application rate of the oil-based suspension concentrates according to the invention can be varied within a relatively wide range. It depends on the particular agrochemical active ingredients and their content in the formulations.
  • agrochemical active substances can be applied in a particularly advantageous manner to plants and / or their habitat.
  • the agrochemical active compounds of the formula (I) present thereby develop a better biological activity (in particular a better insecticidal and / or acaricidal activity and / or a better crop plant compatibility) than when applied in the form of the corresponding conventional formulations.
  • compositions according to the invention are suitable for plant protection, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids and nematodes used in agriculture, in horticulture, in forests and in gardens and recreational facilities. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include: Pests from the strain of Arthropoda, in particular from the class of Arachnida z. Acarus spp., E.g.
  • Acarus siro Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B.
  • Oligonychus coffeae Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., E.g.
  • Panonychus citri Metatetranychus citri
  • Panonychus ulmi Metatetranychus ulmi
  • Phyllocoptruta oleivora Platytetranychus multidigituli
  • Polyphagotarsonemus latus Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp. Steneotarsonemus spinki, Tarsonemus spp. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g.
  • Epitrix cucumeris Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes b Camillus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., E.g.
  • Hypothenemus hampei Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., E.g. Luperoptera spp., Luperodes spp., Luperomorpha xanthodera, Lyctus spp., Megacyllene spp., E.g. Megacyllene robiniae, Megascelis spp., Melanotus spp., E.g.
  • Melanotus longulus oregonensis Meligethes aeneus, Melolontha spp., E.g. Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g.
  • Otiorhynchus cribricollis Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., E.g.
  • Phyllotreta armoraciae Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., E.g.
  • Tribolium audax Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Diptera z.
  • Aedes spp. Z. Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans, Agromyza spp., E.g. Agromyza frontella, Agromyza parvicornis, Anastrepha spp., Anopheles spp., E.g.
  • Anopheles quadrimaculatus, Anopheles gambiae, Asphondylia spp., Bactrocera spp. E.g. Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae, Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp., Chrysomya spp., Chrysops spp., Chrysozona pluvialis, Cochliomya spp., Contarinia spp., E.g.
  • Acyrthosiphon pisum Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., E.g. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp.
  • Aspidiella spp. Aspidiella spp., Aspidiotus spp., E.g. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., E.g. B.
  • Icerya purchasi Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., E.g.
  • B. Lecanium corni ( Parthenolecanium corni), Lepidosaphes spp., Z. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma americanula, Macrosiphum spp., E.g.
  • Macrosiphum euphorbiae Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., E.g.
  • Nephotettix spp. e.g. Nephotettix cincticeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g.
  • Paratrioza cockerelli Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Z. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B.
  • Planococcus citri Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g.
  • Rhopalosiphum maidis Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g.
  • Trioza spp. E.g. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z.
  • Aelia spp. Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g.
  • Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g.
  • Lygus elisus Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monalonion atratum, Nezara spp., Z. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g.
  • Hoplocampa cookei Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., E.g. B. Sirex noctilio, Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp., Vespa spp., e.g. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z.
  • Cydia nigricana Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Dioryctria spp., E.g. B. Dioryctria tremani, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., E.g.
  • Grapholita molesta Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Z. Helicoverpa armigera, Helicoverpa zea, Heliothis spp. Homo. Spp., Hyponomeuta padella, Kakivoria flavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B. Leucoptera coffeella, Lithocolletis spp., Z. B.
  • Pectinophora gossypiella, Perileucoptera spp., Phthorimaea spp., Z. Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter spp., E.g. Phyllonorycter blancardella, Phyllonorycter crataegella, Pieris spp., E.g. Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella ( Plutella maculipennis), Podesia spp., E.g.
  • Trichoplusia ni Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of Orthoptera or Saltatoria z.
  • Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. Cacopaurus pestis, Criconemella spp., E.g. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax ( Mesocriconema xenoplax), Criconemoides spp., E.g. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., E.g.
  • Fongidorus africanus Meloidogyne spp., E.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., E.g. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., E.g.
  • Pratylenchus penetrans Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus spp., Scutellonema spp., Subanguina spp., Trichodorus spp. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. Tylenchorhynchus annulatus, Tylenchulus spp., E.g. B. Tylenchulus semipenetrans, Xiphinema spp., Z. B. Xiphinema index.
  • a nematocide in crop protection as described herein has the ability to control nematodes.
  • controlling nematodes means killing the nematodes or preventing or aggravating their development or growth or preventing or hindering their penetration into or their sucking on the plant tissue.
  • the effectiveness of the compounds is compared by mortality, bile formation, cyst formation, nematode density per volume of soil, nematode density per root, number of nematode eggs per volume of soil, motility of the nematodes between a plant treated with the compound of formula (I) or plant part Soil and an untreated plant, plant part or untreated soil (100%).
  • a reduction of 25-50% compared to an untreated plant, plant part or untreated soil more preferably a reduction of 51-79%, and most preferably complete suppression or complete prevention of development and growth of the nematodes by reduction achieved by 80 to 100%.
  • Control of nematodes as described herein also includes control of nematode proliferation (development of cysts and / or eggs).
  • Compounds of formula (I) may also be used to maintain the plants or animals healthy and may be used for curative, preventive or systemic control of nematode control.
  • Methods are known to the person skilled in the art, such as mortalities, bile formation, cyst formation, nematode density per soil volume, nematode density per root, number of nematode eggs per soil volume, mobility of the nematodes.
  • the use of a compound of the formula (I) can maintain the plant in a healthy state and also involves a reduction in the damage caused by nematodes and an increase in the amount of harvest.
  • nematodes in the present context refers to plant nematodes, under which one summarizes all nematodes that damage plants.
  • Plant nematodes include plant parasitic nematodes and nematodes living in the soil.
  • Plant parasitic nematodes include ectoparasites such as Xiphinema spp., Longidorus spp. and Trichodorus spp .; Semi-parasites such as Tylenchulus spp .; migratory endoparasites such as Pratylenchus spp., Radopholus spp.
  • Root parasitic soil nematodes are, for example, cyst-forming nematodes of the genera Heterodera or Globodera, and / or root-knot nematodes of the genus Meloidogyne.
  • Harmful species of these genera are, for example, Meloidogyne incognita, Heterodera glycines (soybean cyst nematode), Globodera pallida and Globodera rostochiensis (yellow potato cyst nematode), which species are effectively controlled by the compounds described herein.
  • the use of the compounds described herein is by no means limited to these genera or species, but extends equally to other nematodes.
  • the plant parasitic nematodes include e.g. Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp. Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
  • Anguina spp. Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera
  • the listed plants can be treated particularly advantageously with the suspension concentrates according to the invention.
  • the preferred ranges given above for the suspension concentrates also apply to the treatment of these plants.
  • Particularly emphasized is the plant treatment with the suspension concentrates specifically listed herein.
  • the invention is illustrated by the following examples. These are in no way limiting.
  • a suspension concentrate all liquid components are first mixed together. In the next step, the solids are added and the mixture is stirred until a homogeneous suspension is obtained. The homogeneous suspension is first subjected to a coarse and then a fine grinding, so that one contains a suspension in which 90% of the solid particles have a particle size below 10 pm. Then add Kelzan® S and water with stirring at room temperature to achieve the specified viscosity. There is obtained a homogeneous suspension concentrate.
  • Example 3 (OD 048) To prepare an oil-based suspension concentrate, 48 g of the compound of the formula (1-2)
  • Example 5 (OD 024) To prepare an oil-based suspension concentrate, 24 g of the compound of the formula (1-2)
  • One-leaved paprika plants (Capsicum annuum) which are heavily infested with the green peach aphid (Myzus persice) are treated by spraying the leaf top with the preparation of active compound at the desired concentration.
  • the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals were killed.
  • One-leaved cotton plants (Gossypium hirsutum) heavily infested with the cotton aphid (Aphis gossypii) are treated by spraying the leaf top with the preparation of active compound at the desired concentration. After the desired time the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals were killed.
  • RME rapeseed oil methyl ester
  • the evaluation is carried out 3, 5, 7, 10 and 15 days after the treatment by scoring the killing of the animals on the leaves.
  • the evaluation takes place 7, 14 and 21 days after the second treatment by scoring the killing of the animals on the leaves.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP19716433.8A 2018-04-13 2019-04-12 Suspensionskonzentrate auf ölbasis Withdrawn EP3772944A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP18167223 2018-04-13
PCT/EP2019/059445 WO2019197621A1 (de) 2018-04-13 2019-04-12 Suspensionskonzentrate auf ölbasis

Publications (1)

Publication Number Publication Date
EP3772944A1 true EP3772944A1 (de) 2021-02-17

Family

ID=61972450

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19716433.8A Withdrawn EP3772944A1 (de) 2018-04-13 2019-04-12 Suspensionskonzentrate auf ölbasis

Country Status (7)

Country Link
US (1) US20210144992A1 (ko)
EP (1) EP3772944A1 (ko)
JP (1) JP2021521157A (ko)
KR (1) KR20200143434A (ko)
CN (1) CN111970928B (ko)
BR (1) BR112020020186A2 (ko)
WO (1) WO2019197621A1 (ko)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113749089B (zh) * 2020-06-02 2023-11-03 江苏龙灯化学有限公司 一种具有改善的稳定性的油分散组合物
CA3228123A1 (en) * 2021-08-12 2023-02-16 Ishihara Sangyo Kaisha, Ltd. Method for preventing deformation of resin-made agrochemical container

Family Cites Families (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2842476A (en) 1953-04-23 1958-07-08 Mclaughlin Gormley King Co Insecticidal compositions
DE3008186A1 (de) 1980-03-04 1981-10-15 Hoechst Ag, 6000 Frankfurt Synergistische kombinationen von phosphinothricin
JPS638302A (ja) 1986-06-27 1988-01-14 Kao Corp 殺生剤用効力増強剤
JPH0618761B2 (ja) 1986-07-14 1994-03-16 花王株式会社 粒状農薬の製造方法
US5238604A (en) 1987-10-05 1993-08-24 Basf Corporation Crop oil concentrates
JPH0747523B2 (ja) 1990-04-16 1995-05-24 花王株式会社 殺生剤効力増強剤
US5352674A (en) 1991-03-25 1994-10-04 Valent U.S.A. Chemically stable granules containing insecticidal phosphoroamidothioates
US5462912A (en) 1991-10-09 1995-10-31 Kao Corporation Agricultural chemical composition enhancer comprising quaternary di(polyoxyalkylene) ammonium alkyl sulfates
MY111077A (en) 1992-11-13 1999-08-30 Kao Corp Agricultural chemical composition
EP0685995B1 (en) 1993-12-28 1999-07-14 Kao Corporation Enhancer composition for agricultural chemicals and agricultural chemical composition
DE4401542A1 (de) 1994-01-20 1995-07-27 Hoechst Schering Agrevo Gmbh Synergistische Kombinationen von Ammoniumsalzen
DE4416303A1 (de) 1994-05-09 1995-11-16 Bayer Ag Schaumarmes Netzmittel und seine Verwendung
DE19605786A1 (de) 1996-02-16 1997-08-21 Hoechst Schering Agrevo Gmbh Ölsuspensionskonzentrate
GB9703054D0 (en) 1997-02-14 1997-04-02 Ici Plc Agrochemical surfactant compositions
DE19752552A1 (de) 1997-11-27 1999-06-02 Hoechst Schering Agrevo Gmbh Tensidsysteme für flüssige wässrige Zubereitungen
US6165940A (en) 1998-09-25 2000-12-26 American Cyanamid Co. Non-aqueous suspension concentrate
DE19857963A1 (de) 1998-12-16 2000-06-21 Bayer Ag Agrochemische Formulierungen
US7156655B2 (en) 2001-04-13 2007-01-02 Orametrix, Inc. Method and system for comprehensive evaluation of orthodontic treatment using unified workstation
US6423667B1 (en) 2001-05-15 2002-07-23 Honeywell International Inc. Ammonium sulfate suspensions in oils
US6689720B2 (en) 2001-11-14 2004-02-10 Ndsu-Research Foundation High-pH oil based adjuvant blend for enhancing efficacy of pesticides
US6645914B1 (en) 2002-05-01 2003-11-11 Ndsu-Research Foundation Surfactant-ammonium sulfate adjuvant composition for enhancing efficacy of herbicides
WO2003101197A1 (en) 2002-05-31 2003-12-11 Cjb Industries, Inc. Adjuvant for pesticides
US6984662B2 (en) 2003-11-03 2006-01-10 The Hartz Mountain Corporation High concentration topical insecticide containing insect growth regulator
US7132448B2 (en) 2002-09-12 2006-11-07 The Hartz Mountain Corporation High concentration topical insecticide containing insect growth regulator
GB0318448D0 (en) 2003-08-06 2003-09-10 Syngenta Ltd Formulation
DE102004011006A1 (de) * 2004-03-06 2005-09-22 Bayer Cropscience Ag Suspensionskonzentrate auf Ölbasis
DE102004011007A1 (de) 2004-03-06 2005-09-22 Bayer Cropscience Ag Suspensionskonzentrate auf Ölbasis
DE102004026937A1 (de) 2004-06-01 2005-12-22 Bayer Cropscience Gmbh Konzentrierte wäßrige Formulierungen für den Pflanzenschutz
US7651977B2 (en) 2004-10-28 2010-01-26 Valent U.S.A. Corporation Herbicidal compositions
DE102005008021A1 (de) * 2005-02-22 2006-08-24 Bayer Cropscience Ag Spiroketal-substituierte cyclische Ketoenole
WO2007050090A1 (en) 2005-10-28 2007-05-03 Valent U.S.A. Corporation Herbicidal compositions
DE102005059471A1 (de) 2005-12-13 2007-07-12 Bayer Cropscience Ag Herbizide Zusammensetzungen mit verbesserter Wirkung
DE102005059469A1 (de) * 2005-12-13 2007-06-14 Bayer Cropscience Ag Insektizide Zusammensetzungen mit verbesserter Wirkung
DE102006057036A1 (de) 2006-12-04 2008-06-05 Bayer Cropscience Ag Biphenylsubstituierte spirocyclische Ketoenole
MX2011000806A (es) * 2008-07-24 2011-03-15 Bayer Cropscience Ag Espesante para concentrados compatibles con plantas, dispersables en agua.
CA2746394C (en) * 2008-12-12 2017-08-29 Syngenta Limited Spiroheterocyclic n-oxypiperidines as pesticides
BR112015029268B1 (pt) * 2013-05-23 2020-10-20 Syngenta Participations Ag composição pesticida, pacote de combinação, utilização, método de aumento da eficácia e redução da fitotoxicidade de compostos de ácido tetrâmico ativos em termos pesticidas, método não terapêutico para combater e controlar pragas
USRE49006E1 (en) * 2013-05-23 2022-04-05 Syngenta Participations Ag Tank-mix formulations
US20170188581A1 (en) * 2014-03-27 2017-07-06 Bayer Cropscience Aktiengesellschaft Insecticidal and nematocidal active ingredient combinations
CN109563066B (zh) * 2016-08-04 2023-08-29 拜耳作物科学股份公司 制备螺缩酮取代的环状酮烯醇的方法
JP6220945B2 (ja) * 2016-09-27 2017-10-25 花王株式会社 農園芸用殺虫剤
CN107484767A (zh) * 2017-08-14 2017-12-19 江苏龙灯化学有限公司 一种油基悬浮剂及其制备方法和用途

Also Published As

Publication number Publication date
WO2019197621A1 (de) 2019-10-17
CN111970928B (zh) 2023-04-07
JP2021521157A (ja) 2021-08-26
CN111970928A (zh) 2020-11-20
BR112020020186A2 (pt) 2021-01-05
KR20200143434A (ko) 2020-12-23
US20210144992A1 (en) 2021-05-20

Similar Documents

Publication Publication Date Title
WO2015150348A1 (de) VERWENDUNG VON N-ARYLAMIDIN-SUBSTITUIERTEN TRIFLUOROETHYLSULFOXID-DERIVATEN ZUR BEKÄMPFUNG VON SCHÄDLINGEN DURCH ANGIEßEN, TRÖPFCHENAPPLIKATION, TAUCHAPPLIKATION, BODENINJEKTION ODER DURCH DIE BEHANDLUNG VON SAATGUT
ES2905101T3 (es) Combinaciones de compuestos activos con propiedades insecticidas/acaricidas
KR102625757B1 (ko) 살곤충/살진드기 특성을 갖는 활성 화합물 조합물
EP3772944A1 (de) Suspensionskonzentrate auf ölbasis
WO2019197619A1 (de) Suspensionskonzentrate auf ölbasis
EP2531030B1 (de) Wirkstoffkombinationen enthaltend azadirachtin und eine substituierte enaminocarbonylverbindung
AU2018350611B2 (en) Active compound combinations having insecticidal/acaricidal properties
AU2019250592B2 (en) Use of tetramic acid derivatives for controlling pests by watering or droplet application
WO2019197617A1 (de) Verwendung von tetramsäurederivaten zur bekämpfung von tierischen schädlingen durch angiessen, tröpfchenapplikation. pflanzlochbehandlung oder furchenapplikation
WO2023148037A1 (en) Methods and compositions for controlling pests in vegetables
WO2023148034A1 (en) Methods and compositions for controlling pests in perennials
WO2019224143A1 (de) Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften
EP3772960A1 (de) Wirkstoffkombinationen mit insektiziden, nematiziden und akariziden eigenschaften
WO2019076751A1 (en) COMBINATIONS OF ACTIVE COMPOUNDS HAVING INSECTICIDAL / ACARICIDE PROPERTIES

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20201113

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: EXAMINATION IS IN PROGRESS

17Q First examination report despatched

Effective date: 20230118

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: GRANT OF PATENT IS INTENDED

INTG Intention to grant announced

Effective date: 20230904

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20240116