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WO2022105987A1 - Formulations contenant de la cyclodextrine pour l'amélioration de l'efficacité d'acides gras en tant qu'herbicides non sélectifs - Google Patents

Formulations contenant de la cyclodextrine pour l'amélioration de l'efficacité d'acides gras en tant qu'herbicides non sélectifs Download PDF

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Publication number
WO2022105987A1
WO2022105987A1 PCT/EP2020/082411 EP2020082411W WO2022105987A1 WO 2022105987 A1 WO2022105987 A1 WO 2022105987A1 EP 2020082411 W EP2020082411 W EP 2020082411W WO 2022105987 A1 WO2022105987 A1 WO 2022105987A1
Authority
WO
WIPO (PCT)
Prior art keywords
cyclodextrin
fatty acids
mol
solvent
weeds
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.)
Ceased
Application number
PCT/EP2020/082411
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German (de)
English (en)
Inventor
Ingo Jeschke
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.)
Wacker Chemie AG
Original Assignee
Wacker Chemie 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 Wacker Chemie AG filed Critical Wacker Chemie AG
Priority to PCT/EP2020/082411 priority Critical patent/WO2022105987A1/fr
Publication of WO2022105987A1 publication Critical patent/WO2022105987A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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

Definitions

  • the invention relates to a composition for use as a herbicide 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 a herbicide, and a method for controlling weeds, in which this composition or the formulation containing the composition is applied to the areas to be treated.
  • Herbicides are substances designed to kill offending plants. They are mainly used in agriculture, but also on non-crop land. Crops compete with weeds for water, nutrients and light. Dense weed growth can make the harvest very difficult and significantly reduce it. Weeds can be decimated manually, with machines or with herbicides.
  • fatty acids are usually offered as concentrates that are diluted with water to form an oil-in-water emulsion before use.
  • other components such as surfactants and biocides or other classes of active ingredients such as growth regulators can be included in the products.
  • the application rate can vary depending on the weed species and is generally in the range of 30 to 60 kg of fatty acids per hectare applied with a water volume of 800 to 1,200 liters.
  • WO 93/09669 and US 6,323,156 describe aqueous formulations of organoammonium salts of herbicidal fatty acids. Alkylamine salts in particular have a strong odor or are more difficult to biodegrade.
  • EP 0 868 849 describes partially hydrolyzed ammonium salts of fatty acids.
  • succinic acid or other acids of the Krebs cycle are said to improve the herbicidal effect of the fatty acids.
  • WO 2011/161133 describes a pelargonic acid formulation in the form of an oil-in-water emulsion.
  • a commercial product is Scythe®, which contains 57% pelargonic acid and 3% related fatty acids and is proposed for use in combination with synthetic herbicides.
  • the product Finalsan® contains 18.67% pelargonic acid and 3% of a growth regulator and is recommended for home and garden use.
  • Cyclodextrins are cyclic oligosaccharides containing six (oc-), seven (ß-) or eight (y-) D-glucopyranose units connected to one another via a-(1,4) bonds and which are obtained enzymatically from starch. Because of their circular molecular structure with a hydrophobic cavity, cyclodextrins can form reversible complexes with hydrophobic guest molecules form. Due to the hydrophilic surface of cyclodextrins, they can be used to improve the water solubility of hydrophobic substances. At the same time, it is possible to reduce the volatility of volatile substances by forming complexes with cyclodextrins and to achieve delayed release.
  • WO 19/215645 and WO 20/084572 describe that pesticide-cyclodextrin complexes are particularly effective since they increase the solubility of the pesticide, which improves bioavailability, which was investigated with the active ingredients tau fluvalinate and prothioconazole.
  • the active substances were treated with an equimolar amount or with a molar excess of cyclodextrin.
  • WO 2018/050211 describes that it is advantageous for the effective action of a complex of cyclodextrin and insect repellent, i.e. an agent that is active in the air, if the active substance is not completely complexed so that a sufficient proportion is available in the ambient air .
  • the object of the invention was to provide a composition containing natural herbicides which is effective as a herbicide and can therefore be made available for economical use in many fields of application.
  • composition for use as a herbicide 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 one Solvent in the solution (ii) is in a molar ratio to (i) of less than 1 (i.e. the (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 natural herbicide, i.e. (i) is the herbicidal part and is therefore also referred to as the active ingredient part.
  • the composition can be used as a herbicide, i.e. it achieves a herbicidal effect.
  • the herbicidal effect is defined as applying a sample dissolved in 100 ml of solvent to an area of 1 m 2 in dry weather and at an ambient temperature of at least 10 °C, the area containing monocotyledonous and dicotyledonous weeds.
  • the maximum growth height of the weeds is 0.05 m to 0.1 m.
  • the solution is applied in such a way that the solution is sprayed out, ie it is sprayed onto the weeds from a distance of approx. 20-30 cm.
  • the areas are then quantified after different times with regard to their weed growth, with a classification from 0 (no impairment of weed growth) to 10 (complete death of the weeds) being made.
  • the composition can also be used in powder form as a herbicide and applied to the area to be treated.
  • 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.
  • Example 1 shows that the commercially available formulation containing pelargonic acid allowed the weeds to regrow on the treated area after just a few days, while all areas treated with formulations containing cyclodextrin remained free of weeds for a significantly longer period of time.
  • Example 2 also proves that the use of formulations in which pelargonic acid was contained in combination with cyclodextrins made it possible to use significantly lower amounts of active substance in comparison to using the same formulation without the addition of cyclodextrins in order to achieve the same herbicidal effect.
  • the application frequency of the herbicides can also be lowered, which led to large savings in time and material.
  • the effectiveness of (i) can be significantly improved when using the composition as a herbicide, resulting in a reduction in the proportion of (i) (active ingredient proportion), a temporal extension of the herbicidal effect, i.e. prolonged duration of action and a Improvement in the possible uses of the herbicide, e.g. also on weeds with a greater growth height.
  • composition for use as a herbicide ensures that part of the active ingredient (i) remains longer on the site of action after its application, which means that the time of action is significantly prolonged, or the concentration of (i ) can be reduced and the possible uses extended to older and grassy weeds.
  • composition for use as a herbicide contains an active ingredient (i) which belongs to the class of natural herbicides and is therefore environmentally friendly and can also be used in organic farming.
  • the area to be treated is an agricultural, forestry or horticultural area that should remain weed-free.
  • the soil can be treated before sowing. Preference is given to the to treated area around a green area, particularly preferably around a grassy area.
  • Weeds are plants of the spontaneous "accompanying vegetation" in crop stands, grassland or gardens that are not deliberately cultivated there and develop from the seed potential of the soil, via root runners or by the seeds flying in.
  • weeds or crop companions are often spoken of today Undesirable weeds include girsch, thistles, nettles, celandine, clover and dandelion.
  • the composition is suitable for use as a herbicide, which is a non-selective herbicide, i.e. it acts not only against certain plants, but as a broad spectrum or total herbicide.
  • the composition is preferably used as a herbicide, particularly preferably as a non-selective herbicide.
  • a 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, preferably alcohol mixed with water, the solvent is particularly preferably an ethanol-water mixture and particularly preferably water.
  • 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 1:0.05 (mol:mol).
  • composition is preferably characterized in that (ii) is selected from the group consisting of ⁇ -cyclodextrin, ⁇ -cyclodextrin, ⁇ -cyclodextrin, hydroxypropyl- ⁇ -cyclodextrin, acetyl- ⁇ -cyclodextrin, hydroxypropyl- ⁇ - Cyclodextrin, hydroxypropyl- ⁇ -cyclodextrin, acetyl- ⁇ -cyclodextrin, methyl- ⁇ -cyclodextrin, acetyl- ⁇ -cyclodextrin and mixtures thereof.
  • (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 - ⁇ -cyclodextrin or mixtures thereof, it is particularly preferred that (ii) is hydroxypropyl- ⁇ -cyclodextrin, methyl- ⁇ -cyclodextrin or hydroxypropyl- ⁇ -cyclodextrin.
  • a cyclodextrin derivative such as hydroxypropyl- ⁇ -cyclodextrin, acetyl- ⁇ -cyclodextrin, hydroxypropyl- ⁇ -cyclodextrin, hydroxypropyl- ⁇ -cyclodextrin, acety
  • the methyl-ß-cyclodextrin and the hydroxypropyl-ß-cyclodextrin have a water solubility that is many times higher than that of the native ß-cyclodextrin.
  • 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 caprylic acid (C8), pelargonic acid (C9), capric acid (CIO), undecanoic acid (CII), lauric acid (C12) and mixtures thereof. Especially (i) is preferably caprylic acid (C8), pelargonic acid (C9), capric acid (CIO) or a mixture thereof, particularly preferably pelargonic acid (C9).
  • the composition is characterized in that after dissolving (i) and (ii) in a solvent, the percentage of (i) in the solution is 3%, more preferably 2% and most preferably 1%.
  • the percentage refers to the total concentration of (i) in the composition, i.e. if (i) is a mixture of, for example, three different fatty acids and each is present at 1%, the percentage of (i) total is 3% .
  • the composition can be used as a herbicide.
  • 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 a herbicide.
  • a formulation can contain components such as solvents, biocides, 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 additionally contains a solvent.
  • a solvent it being particularly preferred that water is used as the solvent.
  • the herbicidal formulation is produced in a known manner by combining all the components to form a formulation.
  • the cyclodextrin complexes can be prepared 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 fatty acid 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 fatty acid is added in portions and the mixture is stirred at the stated temperature for 16 hours. Uncomplexed fatty acids are filtered off and the complex is isolated by freeze drying.
  • the cyclodextrin or cyclodextrin derivative is combined with the fatty acid in the desired Ratio mixed and water added at a level of 30% 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 eight hours, the paste is dried and ground for further use.
  • the cyclodextrin complex can easily be obtained as a physical mixture by metering the cyclodextrins into a formulation already containing the active ingredients.
  • a further subject matter is a method for controlling weeds, characterized in that the formulation is applied to the areas to be treated.
  • the herbicidal formulation containing saturated or unsaturated fatty acids, their salts or esters and cyclodextrins or cyclodextrin derivatives and optionally other components such as a solvent is currently typically applied in agriculture at an application rate of 30 kg to 60 kg of active ingredient per hectare (Ha). applied , which means that it is applied with 800 to 1200 liters of water per ha .
  • the application takes place by means of spray aircraft or spray vehicles or smaller spray devices.
  • the active substance content refers here to the content of fatty acids, their salts or esters.
  • the amount used can be reduced to 10 kg to 20 kg of active ingredient per hectare.
  • the herbicidal formulation is sprayed onto the weeds using standard methods. Not only young weeds with a growth height below 0.05 m, but also taller weeds can be treated. In addition, not only broadleaf weeds but also grassy weeds can be treated with it.
  • Example 1 Use of a commercial concentration of fatty acids in combination with cyclodextrins

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

Abstract

L'invention concerne une composition destinée à être utilisée en tant qu'herbicide, contenant (i) des acides gras saturés ou insaturés ou des sels ou esters de ceux-ci et (ii) une cyclodextrine ou un dérivé de cyclodextrine. Après la dissolution de (i) et (ii) dans un solvant, (ii) est présent dans la solution en un rapport molaire à (i) inférieur à 1 (c'est-à-dire que le rapport (i):(ii) est de 1:moins de 1 (mol:mol)). En outre, l'invention concerne une formulation qui contient ladite composition et qui est utilisée en tant qu'herbicide et un procédé pour la lutte contre des mauvaises herbes, ladite composition ou la formulation contenant la composition étant appliquée sur les zones à traiter.
PCT/EP2020/082411 2020-11-17 2020-11-17 Formulations contenant de la cyclodextrine pour l'amélioration de l'efficacité d'acides gras en tant qu'herbicides non sélectifs Ceased WO2022105987A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/EP2020/082411 WO2022105987A1 (fr) 2020-11-17 2020-11-17 Formulations contenant de la cyclodextrine pour l'amélioration de l'efficacité d'acides gras en tant qu'herbicides non sélectifs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2020/082411 WO2022105987A1 (fr) 2020-11-17 2020-11-17 Formulations contenant de la cyclodextrine pour l'amélioration de l'efficacité d'acides gras en tant qu'herbicides non sélectifs

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WO2022105987A1 true WO2022105987A1 (fr) 2022-05-27

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Citations (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2626862A (en) 1950-06-30 1953-01-27 Thompson Boyce Plant Res Method of killing plants
US4975110A (en) 1989-10-13 1990-12-04 Safer, Inc. Fatty acid based herbicidal compositions
WO1991005472A1 (fr) * 1989-10-13 1991-05-02 Safer, Inc. Concentre emulsifiable a base d'acides gras presentant une activite herbicide
GB2247621A (en) 1990-09-06 1992-03-11 Pan Britannica Ind Ltd Herbicidal composition
US5098467A (en) 1989-10-13 1992-03-24 Safer, Inc. Fatty acid based herbicidal compositions
US5106410A (en) 1989-10-13 1992-04-21 Safer, Inc. Fatty acid based herbicidal compositions
WO1993009669A1 (fr) 1991-11-22 1993-05-27 Mycogen Corporation Nouveaux sels d'acides gras presentant une efficacite herbicide
US5284819A (en) 1992-05-01 1994-02-08 Mycogen Corporation Herbicidally-active glycol esters of fatty acids
EP0868849A1 (fr) 1997-04-04 1998-10-07 W. NEUDORFF GmbH KG Savon herbicide non tachent
US6323156B1 (en) 2000-04-27 2001-11-27 Falcon Lab Llc Method of using ammonium fatty acid salts as non-selective herbicides
US20040186022A1 (en) 1999-10-26 2004-09-23 Applied Carbochemicals, Inc. Enhanced herbicides
WO2010049954A1 (fr) * 2008-10-31 2010-05-06 Lipid Pharmaceuticals Ehf. Acides gras pour utilisation comme médicament
WO2011161133A2 (fr) 2010-06-24 2011-12-29 Compo Gmbh& Co. Kg Formulation d'acide pélargonique
US8569211B2 (en) 2008-02-18 2013-10-29 Nof Corporation Method of applying a herbicidal composition
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
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 (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2626862A (en) 1950-06-30 1953-01-27 Thompson Boyce Plant Res Method of killing plants
US4975110A (en) 1989-10-13 1990-12-04 Safer, Inc. Fatty acid based herbicidal compositions
WO1991005472A1 (fr) * 1989-10-13 1991-05-02 Safer, Inc. Concentre emulsifiable a base d'acides gras presentant une activite herbicide
US5035741A (en) 1989-10-13 1991-07-30 Safer, Inc. Fatty acid based emulsifiable concentrate having herbicidal activity
US5098467A (en) 1989-10-13 1992-03-24 Safer, Inc. Fatty acid based herbicidal compositions
US5106410A (en) 1989-10-13 1992-04-21 Safer, Inc. Fatty acid based herbicidal compositions
GB2247621A (en) 1990-09-06 1992-03-11 Pan Britannica Ind Ltd Herbicidal composition
WO1993009669A1 (fr) 1991-11-22 1993-05-27 Mycogen Corporation Nouveaux sels d'acides gras presentant une efficacite herbicide
US5284819A (en) 1992-05-01 1994-02-08 Mycogen Corporation Herbicidally-active glycol esters of fatty acids
EP0868849A1 (fr) 1997-04-04 1998-10-07 W. NEUDORFF GmbH KG Savon herbicide non tachent
US20040186022A1 (en) 1999-10-26 2004-09-23 Applied Carbochemicals, Inc. Enhanced herbicides
US6323156B1 (en) 2000-04-27 2001-11-27 Falcon Lab Llc Method of using ammonium fatty acid salts as non-selective herbicides
US8569211B2 (en) 2008-02-18 2013-10-29 Nof Corporation Method of applying a herbicidal composition
WO2010049954A1 (fr) * 2008-10-31 2010-05-06 Lipid Pharmaceuticals Ehf. Acides gras pour utilisation comme médicament
WO2011161133A2 (fr) 2010-06-24 2011-12-29 Compo Gmbh& Co. Kg Formulation d'acide pélargonique
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
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

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SZENTE L ET AL: "FATTY ACID-CYCLODEXTRIN COMPLEXES: PROPERTIES AND APPLICATIONS", JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, KLUWER, DORDRECHT, NL, vol. 16, no. 4, 1 January 1993 (1993-01-01), pages 339 - 354, XP000675556, ISSN: 0923-0750, DOI: 10.1007/BF00708714 *

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