WO2022156882A1 - Formulations contenant de la cyclodextrine et des acides gras pour combattre et repousser les insectes ayant un effet amélioré - Google Patents

Formulations contenant de la cyclodextrine et des acides gras pour combattre et repousser les insectes ayant un effet amélioré Download PDF

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Publication number
WO2022156882A1
WO2022156882A1 PCT/EP2021/051051 EP2021051051W WO2022156882A1 WO 2022156882 A1 WO2022156882 A1 WO 2022156882A1 EP 2021051051 W EP2021051051 W EP 2021051051W WO 2022156882 A1 WO2022156882 A1 WO 2022156882A1
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Prior art keywords
cyclodextrin
acid
composition
solvent
fatty acids
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PCT/EP2021/051051
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German (de)
English (en)
Inventor
Ingo Jeschke
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Wacker Chemie Ag
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Priority to PCT/EP2021/051051 priority Critical patent/WO2022156882A1/fr
Publication of WO2022156882A1 publication Critical patent/WO2022156882A1/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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the invention relates to a composition for use as an insecticide or biocide containing (i) saturated or unsaturated fatty acids, their salts or esters and (11) a cyclodextrin or cyclodextrin derivative, wherein after dissolving (i) and (ii) in a solvent in the solution (ii) is in a molar ratio to (i) of less than 1 (i.e. the ratio (i):(ii) is 1:less than 1 (mole:mole)). Furthermore, the invention relates to a formulation containing this composition, which is used as an insecticide or biocide, and a method for protecting against insects, characterized in that the composition according to the invention is applied to the skin or to other surfaces or textiles.
  • insects are considered pests of humans and animals because they are thought to be vectors of disease transmission. In addition, they can cause damage to agricultural products and are sometimes seen as a massive nuisance when staying outdoors. These insects include ants, cockroaches, bed bugs, sand fleas, dust mites, fleas, flies, lice, termites, wasps, ticks and most importantly mosquitoes. Many mosquitoes can transmit life-threatening diseases as so-called vectors. Aedes aegypti acts as a vector for dengue fever and yellow fever, Anopheles sspec. for malaria, Glossina sspec. for sleeping sickness and Culex sspec. for West Nile disease.
  • the migratory stable fly poses a threat to cattle herds, as it not only reduces milk yield, but also transmits the causative agent of bovine teat atresia.
  • Ticks are a worldwide parasite that feeds on the blood of many vertebrates. If the tick is infected with pathogens, a tick bite can be dangerous for humans.
  • the virus disease TBE (tick-borne encephalitis) and the bacterium Borreliosis sspec. be transmitted . When bed bugs bite, they emit a substance that can cause severe allergic reactions. Cockroaches or cockroaches can transmit salmonella and mold spores, increasing the risk of gastrointestinal disease.
  • insect repellents One way to avoid mosquito bites, ticks, bed bugs and other insects is to apply insect repellents to the skin. These substances can also be used to deter and eliminate insects on surfaces such as house interior walls, floors, terraces, etc. to be applied .
  • An important representative of the insect repellents is DEET (diethyl toluamide), which has a wide range of effects, but can cause allergies, damage plastics, synthetic fibers and leather with its dissolving properties and generally cause irritation.
  • Other repellents such as ethylbutyl acetylaminopropionate (IR 3535), I-caridin, para-menthane-3, 8-diol or certain essential oils are much more skin-friendly, but have a lower protective effect.
  • Insecticides are also used to kill, drive away or inhibit insects such as ants, cockroaches, bed bugs, termites or similar pests.
  • Important representatives of the classic synthetic insecticides are phosphoric acid esters, carbamates, neonicotinoids or pyrethroids. Despite their excellent effect, they can lead to strong resistances in the target organisms, are dangerous to humans and pets and can trigger allergies. Therefore, one is looking for alternative, less toxic active ingredients that can be used as insect repellents or insect repellents. Insecticides can be used to control pests.
  • Naturally occurring fatty acids contain both polar (carboxylic acid groups) and non-polar (alkyl groups) structural components and are described as natural repellents for a large number of insects.
  • Low molecular weight fatty acids are sufficiently volatile to evaporate from surfaces such as human skin. It has been found that fatty acids with 6 to 12 carbon atoms have a stronger repellent effect than DEET.
  • fatty acids and their salts have a toxic effect on certain insects such as beetles, lice, cicadas, bugs, ants, cockroaches and the like. It is assumed that the fatty acids or their salts attach themselves to the cuticle of the insects in order to then be incorporated via the trachea. Apparently, the fatty acids and their salts can destroy the structure of the cell membranes inside the insect.
  • Patent DE 698 17 595 T2 describes insect repellents which are based on a mixture of fatty acids.
  • Steven R. Sims Topicical and Vapor Toxicity of Saturated Fatty Acids to the German Cockroach ( Dictyoptera : Blattellidae ), J. of Economic Entomology, pp. 758-763, 2014 ) conducted tests in 2014 measuring the effectiveness of saturated fatty acids against cockroaches .
  • Junwei J. Zhu (Better than DEET Repellent Compounds Derived from coconut Oil , Nature Sei- entific Reports, p. 1453-1465, 2018) examined in 2018 the insect repellent effect of fatty acids, which were obtained from coconut oil as a cheap and toxicologically harmless alternative to synthetic active ingredients.
  • fatty acids and their salts represent an ecologically justifiable alternative to classic insect repellents and insecticides.
  • these are often not sufficiently effective compared to synthetic active substances, or do not remain at the site of action long enough to provide lasting benefit due to their high volatility .
  • Cyclodextrins are cyclic oligosaccharides containing six (a-), seven (ß-), or eight , containing D-glucopyranose units connected to one another via a-(1,4)-bonds and which are obtained enzymatically from starch. Due to their ring-shaped molecular structure with a hydrophobic cavity, cyclodextrins can form reversible complexes with hydrophobic guest molecules. Due to the hydrophilic surface of the cyclodextrins, the water solubility of hydrophobic substances can be greatly improved with their help.
  • WO 19/215645 and WO 20/084572 describe that pesticide-cyclodextrin complexes are particularly effective because they increase the solubility increase the potency of the pesticide, which improves bioavailability, which has been studied with the active substances tau-fluvalinate and prothioconazole.
  • active ingredients are the classic active ingredients that are bad for beneficial insects, can induce resistance and are toxic to the environment.
  • equimolar amounts or a molar excess of cyclodextrin were added to the active substances.
  • WO 2018/050211 describes that it is advantageous for the effective action of a repellent based on a complex of cyclodextrin and DEET if the active substance is not completely complexed so that it is available in sufficient proportion in the ambient air.
  • the disadvantage of this complex is that the classic insect repellent DEET has an irritating effect on many materials.
  • US 2012/149564 A is directed to an insecticidal composition containing athranil diamide insecticides and cyclodextrin.
  • This class of chemicals which is highly effective on insects and invertebrates, is a relatively new class of compounds that also affects beneficial insects. In addition, resistance can develop.
  • An approved formulation based on this was classified as hazardous to bees. Despite the classification as slightly toxic for humans, individual cases of poisoning by, for example, chlorantraniliprole have been reported, so that there are also disadvantages in the use of complexes with athranil diamides.
  • the object of the invention was to provide a composition containing an ecologically justifiable variant of a classic insecticide or biocide, ie an environmentally friendly active substance for combating insects, which can be used effectively in a formulation for controlling and repelling insects.
  • This object was achieved in that a composition for use as an insecticide or biocide containing (i) saturated or unsaturated fatty acids, their salts or esters and (ii) a cyclodextrin or cyclodextrin derivative, wherein after dissolving (i) and (ii) in a solvent in the solution (ii) is present in a molar ratio to (i) of less than 1 (ie the ratio (i):(ii) is 1:less than 1 (mole:mole)).
  • the composition is a mixture of components (i) and (ii).
  • the saturated or unsaturated fatty acids, their salts or esters are the insecticide or biocide, i.e. (i) is the insecticidally active part and is therefore also referred to as the active ingredient part.
  • the composition can be used as an insecticide or biocide, i.e. it is an environmentally friendly active ingredient for controlling insects and achieves an insecticidal effect.
  • the composition can be spread directly as a powder or processed and applied in the form of pellets.
  • the molar ratio of (i):(ii) according to the invention is achieved when the composition dissolves, for example in rainwater in rainwater or in morning dew water.
  • the amount of (i) and (ii) to be used to achieve the molar ratio according to the invention results from their molecular weight and is therefore easy to calculate.
  • the insect killing and repellent compositions containing cyclodextrin and fatty acids have improved efficacy and may be preferentially applied to the skin of humans or animals as well as for the treatment of textiles or surfaces. It was surprising that when using fatty acids, their salts or esters as the active substance, the cyclodextrins or cyclodextrin derivatives used could be added in a less than equimolar ratio to the active substance. This was particularly surprising for an environmentally friendly composition for use as an insecticide or biocide, which can thus be used effectively and cost-effectively, for example, in ecological agriculture, near children or directly on people.
  • insecticide is a means of killing, repelling or inhibiting insects and their developmental stages.
  • the term insecticide is used in agriculture and forestry.
  • composition is used as an insecticide and more preferred that the composition is used as an insecticide and the insecticide is an insecticide, ie. H . a means of killing insects.
  • a biocide is a non-agricultural and non-plant protection agent used to repel or kill insects.
  • the term is used in particular for the protection of stored products and materials, in animal breeding including livestock farming, in the hygiene sector and in private households.
  • the biocides include z. B. Disinfectants, rat poison or wood preservatives. Biocides are intended for that to protect human health and products, d . H . In comparison to insecticides, the type and place of use of biocides is different (on people or in their homes, in the fields or in greenhouses and storage).
  • composition is used as a biocide and most preferred that the composition is used as a biocide and the biocide is an insecticide, ie. H . a means of killing insects.
  • the composition is effective as an insect killer.
  • both the insecticide and the biocide are agents for killing insects.
  • agents that act as repellents, ie serve to deter and/or drive away insects, are not the subject of the invention.
  • Repellents are a class of biocides that repel organisms without killing them. They are also interchangeably referred to as insect repellents. Repellents are often perceived by an organism via the sense of smell. But an oral intake of the active substance, ie an effect on the sense of taste, is possible and is found e.g. B. used to deter wild boar
  • the insecticidal effect is defined as the application of a sample of about 2 ⁇ l with an active substance concentration of 1-2% to the surface of the cuticle, namely on the ventral side of the body between the pairs of legs of anesthetized crawling or flying insects belonging to the pests count, such as a cockroach.
  • the effect of the sample is determined as an LDso value within the next 24 hours, i. H . the dose is given in mg, the lethal effect of which relates to 50 percent of the observed population. The smaller the LDso value, the smaller the amount of sample that needs to be used for the insect to die.
  • insecticidal effect or insecticidal action is used both for insecticides and for biocides.
  • pests refers only to insects and is also referred to synonymously with harmful insects.
  • the expression is a collective term for organisms that reduce the economic success of humans, be it as destroyers of cultivated plants, as food competitors or by destroying buildings.
  • Agricultural pests field beetle, codling moth, aphids, leaf edge beetles, thrips, fruit shell moth, potato beetle, cherry fruit fly, May beetle, corn borer, plum moth, rhododendron cicada, seed owl, scale insects, gypsy moth, spider mite, grape berry moth , Walnut fruit fly, Whitefly, Western corn rootworm Forest pests: certain aphids, Blue pine borer, Bark beetle, Oak borer, Oak processiffy moth, Oak moth, Spruce spider sawfly, Common woodworm (often just referred to as the woodworm) , Large brown barkeater, Pine sawfly, Pine owl, Pine moth, Small spruce sawfly , nun, horse chestnut leaf miner, gypsy moth, sapwood beetle
  • Wood pests woodworm beetle (often colloquially referred to as "woodworm"), house longhorn (often mistakenly confused with wood tick), sapwood beetle, termites
  • a solvent also solvent or solvent is a substance that can dissolve or dilute gases, liquids or solids without chemical reactions occurring between the dissolved substance and the solvent. Water, alcohols or ketones can be used as solvents.
  • composition for use as an insecticide or biocide contains an active ingredient (i) that belongs to the class of environmentally friendly active ingredients and thus also in organic farming and all products on humans or in contact with the People or who can be used in his vicinity.
  • the effectiveness of (i) in the composition can be significantly improved, resulting in a reduction in the proportion of (i) (active ingredient proportion), a temporal extension of the effect and an improvement in the possible uses as an insecticide or biocide result.
  • An advantage of the more effective effectiveness of the complexes from (i) and (ii) is, for example, that the application frequency can be lowered, which leads to a large saving in time and material.
  • Example 1 proves that the complexation of fatty acids, such as in this case getanoic, nonanoic or decanoic acid, with methylated beta-cyclodextrin (M-ß-CD) brings about a significant improvement in insecticidal effectiveness compared to the corresponding free, non-complexed fatty acid.
  • M-ß-CD methylated beta-cyclodextrin
  • test result from example 2 shows a clear increase in the insect repellent effect by up to 40% when fatty acids are used together with cyclodextrins compared to the use of fatty acids without the addition of cyclodextrins. This result could be shown for three different fatty acids and two different cyclodextrin derivatives.
  • the test results mentioned clearly show that the combination of cyclodextrins with fatty acids to improve the insecticidal effect has the advantage of being able either to reduce the amount of fatty acids used or to be able to maintain the effectiveness of the fatty acids over a longer period of time. It was surprisingly found that the amount of cyclodextrin used must be lower than the sum of the fatty acids.
  • fatty acids cyclodextrin mixture offers an effective ecological alternative to conventional insecticides or biocides.
  • fatty acids effectively as an insecticidal or biocidal active ingredient with cyclodextrins in insect control and defense means that an environmentally friendly composition that is non-toxic to both humans and animals, including pets, can be made available.
  • the composition is characterized in that after dissolving (i) and (ii) in a solvent, the molar ratio of (i):(ii) in the solution is between 1:0.01 and 1:0.5 (mol: mol) lies. Particularly preferably, after dissolving (i) and (ii) in a solvent, the molar ratio of (i):(ii) in the solution is 1:0.025 to 1:0.05 (mol:mol), particularly preferably 1: 0.05 (mole : mole) .
  • (ii) is selected from the group consisting of ⁇ -cyclodextrin, ⁇ - Cyclodextrin, y-cyclodextrin, hydroxypropyl-a-cyclodextrin, acetyl-a-cyclodextrin, hydroxypropyl-ß-cyclodextrin, hydroxypropyl-y-cyclodextrin, acetyl-ß-cyclodextrin, methyl-ß-cyclodextrin, acetyl-y-cyclodextrin and their mixtures.
  • (ii) is particularly preferably a native cyclodextrin such as ⁇ -cyclodextrin, ⁇ -cyclodextrin, ⁇ -cyclodextrin or a mixture thereof, particularly preferably ⁇ -cyclodextrin and/or ⁇ -cyclodextrin.
  • (ii) is a cyclodextrin derivative such as hydroxypropyl- ⁇ -cyclodextrin, acetyl- ⁇ -cyclodextrin, hydroxypropyl- ⁇ -cyclodextrin, hydroxypropyl- ⁇ -cyclodextrin, acetyl- ⁇ -cyclodextrin, methyl- ⁇ -cyclodextrin , Acetyl-y-cyclodextrin or mixtures thereof, it is particularly preferred that (ii) is hydroxypropyl-ß-cyclodextrin or methyl-ß-cyclodextrin.
  • Saturated or unsaturated fatty acids, their salts or esters are used as insecticidal or biocidal active ingredients.
  • the composition is preferably characterized in that (i) has a chain length of 6 to 20 carbon atoms. Particular preference is given to (i) being selected from the group consisting of hexanoic acid (C6, caproic acid), heptanoic acid (C7, enanthic acid), octanoic acid (C8, caprylic acid), nonanoic acid (C9, pelargonic acid), decanoic acid (CIO, capric acid) , undecanoic acid (Cll), dodecanoic acid (C12, lauric acid), their unsaturated representatives, their homologues and mixtures thereof.
  • C6 hexanoic acid
  • C7 heptanoic acid
  • octanoic acid C8 caprylic acid
  • nonanoic acid C9, pelargonic acid
  • decanoic acid C
  • (i) is particularly preferably caprylic acid (C8), pelargonic acid (C9), capric acid (CIO) or a mixture thereof, particularly preferably it is a mixture of a C8, C9 and ClO fatty acid in each case equal share.
  • unsaturated representatives or homologues of the fatty acids mentioned can also be used.
  • the composition is characterized in that after dissolving (i) and (ii) in a solvent, the percentage of each fatty acid in the solution is 1.5%.
  • This preferred percentage level does not relate to the total concentration of (i) in the composition but to each individual fatty acid, ie where (i) is a mixture of for example three different fatty acids each is preferably present at a level of 1.5% .
  • the dry composition can be used directly as an insecticide or biocide, for example by scattering the powder and dissolving in rainwater.
  • the composition according to the invention can also serve as a basis for the production of a formulation.
  • a further object of the invention is therefore a formulation containing the composition according to the invention, characterized in that it is used as an insecticide or biocide.
  • a formulation may contain components such as solvents, surfactants, viscosity regulators, antifoams, preservatives, emulsifiers and/or other classes of active ingredients such as growth regulators.
  • the aim of the formulation is to optimize the biological effect of the composition in the target organism and, at the same time, to bring the finished product into a form that can be used in technical equipment. In this way, not only the effectiveness but also, for example, the shelf life of the formulation should be optimized.
  • the formulation is used to kill insects.
  • the formulation additionally contains a solvent.
  • a solvent is particularly preferred for the solvent to contain water.
  • the solvent is particularly preferably an acetone-water mixture.
  • composition according to the invention is produced in a manner known per se by combining all the components.
  • Active substances can be used either in the form of a physical mixture with the cyclodextrins, or these in the form of cyclodextrin complexes, or be used as a combination of these two options.
  • the fatty acid-cyclodextrin complexes can be produced by any of the methods known in the prior art, preferably by the co-precipitation process, the melting-in process or the paste process.
  • the active substance is dissolved in a suitable solvent and added in the desired ratio to an aqueous solution of the cyclodextrin or cyclodextrin derivative heated to 20 to 70.degree. C., preferably to 50.degree.
  • the solution is stirred for a period of 16 hours and then the solvent is removed.
  • the residue is dried at 40° C.
  • the solvent is preferably acetone, methanol or ethanol.
  • the cyclodextrin or cyclodextrin derivative is placed in water and heated to 20 to 70.degree. C., preferably 50.degree.
  • the active ingredient is added in portions and stirred at the stated temperature for 16 hours. Uncomplexed active substance is filtered off and the complex is isolated by freeze-drying.
  • the cyclodextrin or the cyclodextrin derivative is mixed together with the active substance in the desired ratio and water is added in a proportion of 30 percent by weight of the two components.
  • the resulting paste is kept in a closed glass vessel at 70° C. for a period of eight hours and mixed hourly with a spatula. After the eight hours, the paste is dried and for the further
  • the fatty acid-cyclodextrin complex is then incorporated into the solution used as formulation, for example by dissolving the product from the co-precipitation, melting-in or paste process in the solution used as formulation while stirring at room temperature.
  • the cyclodextrin complex can easily be produced as a physical mixture by metering the cyclodextrins into a formulation that already contains the active ingredients.
  • a further object is a method for protecting against insects, characterized in that the composition, preferably the formulation, is applied to the skin or to other surfaces or textiles.
  • the method according to the invention makes it possible to repel and control insects with a clear improvement in the effectiveness of the insect repellent and a clear prolongation of the duration of action of the insect repellent.
  • cockroaches each (BioGenius, Technologiepark, Bergisch Gladbach) were placed in a 10 cm x 2 cm Petri dish, the sides of which were treated with a mixture of mineral oil and vaseline (ratio 1:3, Sigma Aldrich) to prevent the to avoid animals.
  • the cockroaches were treated with carbon dioxide for 15 to 25 seconds until anesthetized and positioned ventral side up. 2 ⁇ l each of the formulations were applied to the area between the pairs of legs and the insects were examined within the next 24 hours.
  • the mortality of the individual formulations was evaluated by determining the mean lethal dose LD50.
  • the LDso value indicates the dose in mg whose lethal effect relates to 50 percent of the observed population.
  • Example 2 Efficacy of fatty acids complexed with cyclodextrin to combat ants
  • Example 2 The experiment described in Example 1 was repeated, with the difference that, to improve the effectiveness, hydroxypropylated beta-cyclodextrin (HP-ß-CD, Wacker Chemie AG, molecular weight 1542 g/mol) was used in a molar ratio of 1:0.5 (fatty acid : cyclodextrin) was added. The pure solvent mixture served as a control. tab . 2: Contact toxicity when using the formulations from Example 2. This formulation can also be applied to other pests such as ticks, beetles, lice, leaf hoppers and the like.
  • HP-ß-CD Wacker Chemie AG, molecular weight 1542 g/mol

Abstract

L'invention concerne une composition destinée à être utilisée comme insecticide ou biocide, la composition contenant (i) des acides gras saturés ou insaturés, des sels ou des esters de ceux-ci, et (ii) une cyclodextrine ou un dérivé de cyclodextrine, après que (i) et (ii) sont dissous dans un solvant, (ii) est présent dans la solution selon un rapport molaire avec (i) inférieur à 1 (autrement dit, le rapport de (i) : (ii) est de 1 : moins de 1 (mol : mol)). L'invention concerne également une formulation contenant cette composition, laquelle est utilisée comme insecticide ou biocide, et un procédé pour repousser les insectes. L'invention est caractérisée en ce que la composition ou la formulation selon l'invention est appliquée sur la peau ou sur d'autres surfaces ou textiles.
PCT/EP2021/051051 2021-01-19 2021-01-19 Formulations contenant de la cyclodextrine et des acides gras pour combattre et repousser les insectes ayant un effet amélioré WO2022156882A1 (fr)

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US2827452A (en) * 1955-05-31 1958-03-18 Univ Minnesota Stabilization of materials
FR2596617A1 (fr) * 1986-04-08 1987-10-09 Orstom Composition a base d'acide gras complexe par des cyclodextrines, son procede de preparation et application phytosanitaire
DE69817595T2 (de) 1997-06-30 2004-04-22 Reifenraht, William G., Richmond Natürliches insekten- und arthropodenvertreibungsmittel
WO2010049954A1 (fr) * 2008-10-31 2010-05-06 Lipid Pharmaceuticals Ehf. Acides gras pour utilisation comme médicament
US20120149564A1 (en) 2010-12-13 2012-06-14 E. I. Du Pont De Nemours And Company Anthranilic diamide and cyclodextrin compositions for propagule coating
WO2018050211A1 (fr) 2016-09-13 2018-03-22 Wacker Chemie Ag Formulation contenant de la cyclodextrine pour combattre et repousser les insectes dotée d'une efficacité améliorée
WO2019048759A1 (fr) * 2017-09-08 2019-03-14 Inoventeam Composition phytopharmaceutique à base d'alkyl pentoside et d'acide nonanoïque et son utilisation en tant qu'herbicide
CN109793014A (zh) * 2019-02-21 2019-05-24 江西生成卫生用品有限公司 一种高效低毒杀虫剂及其制备方法
WO2019215645A1 (fr) 2018-05-09 2019-11-14 Adama Makhteshim Ltd. Utilisation de cyclodextrines comme système d'administration agrochimique
WO2020084572A1 (fr) 2018-10-24 2020-04-30 Adama Makhteshim Ltd. Utilisation de cyclodextrines comme système d'administration agrochimique

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2827452A (en) * 1955-05-31 1958-03-18 Univ Minnesota Stabilization of materials
FR2596617A1 (fr) * 1986-04-08 1987-10-09 Orstom Composition a base d'acide gras complexe par des cyclodextrines, son procede de preparation et application phytosanitaire
DE69817595T2 (de) 1997-06-30 2004-04-22 Reifenraht, William G., Richmond Natürliches insekten- und arthropodenvertreibungsmittel
WO2010049954A1 (fr) * 2008-10-31 2010-05-06 Lipid Pharmaceuticals Ehf. Acides gras pour utilisation comme médicament
US20120149564A1 (en) 2010-12-13 2012-06-14 E. I. Du Pont De Nemours And Company Anthranilic diamide and cyclodextrin compositions for propagule coating
WO2018050211A1 (fr) 2016-09-13 2018-03-22 Wacker Chemie Ag Formulation contenant de la cyclodextrine pour combattre et repousser les insectes dotée d'une efficacité améliorée
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