WO2023017427A1 - Composition concentrée émulsifiable comprenant du carvacrol - Google Patents

Composition concentrée émulsifiable comprenant du carvacrol Download PDF

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WO2023017427A1
WO2023017427A1 PCT/IB2022/057439 IB2022057439W WO2023017427A1 WO 2023017427 A1 WO2023017427 A1 WO 2023017427A1 IB 2022057439 W IB2022057439 W IB 2022057439W WO 2023017427 A1 WO2023017427 A1 WO 2023017427A1
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Prior art keywords
esters
oil
amount
composition according
ethoxylated
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PCT/IB2022/057439
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English (en)
Inventor
Elisa GALIMBERTI
Claudio DACARRO
Giovanni Pozzi
Stefano CIANNAMEA
Pietro QUERZOLA
Alessandra FRATANGELI
Francesca Borgo
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Sipcam Oxon S.P.A.
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Publication of WO2023017427A1 publication Critical patent/WO2023017427A1/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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • 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
    • A01N25/02—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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/22—Lamiaceae or Labiatae [Mint family], e.g. thyme, rosemary, skullcap, selfheal, lavender, perilla, pennyroyal, peppermint or spearmint
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides

Definitions

  • the present invention refers to compositions for the phytosanitary use.
  • the present invention refers to emulsifiable concentrated formulations comprising carvacrol.
  • plant protection product means compounds or compositions used in agriculture to at least partially kill the parasites damaging cultivated plants, such as for example fungi, pathogenic insects and the like, in order to protect the health of said plants and to guarantee their survival.
  • plant protection products or phytodrugs are also named, sometimes inappropriately, parasiticides, fungicides, pesticides and biocides.
  • Carvacrol or 2-methyl-5 -isopropylphenol, having the following formula (I) is present for example in the essential oil of oregano (Origanum spp.) and Satureja (Satureja spp.) and has very good antifungal and antibacterial properties, showing at the same time little toxicity to higher species of animals.
  • Carvacrol is poorly soluble in water.
  • the poor water solubility of such compound makes its administration to the plants difficult. Indeed, typically, the plant protection products are administered to the plants through an aqueous medium.
  • emulsifiable concentrates also known as "EC"
  • EC emulsifiable concentrates
  • the resulting emulsions are generally scarcely stable, quickly undergoing phase separation, that is, the separation of the oil phase from the aqueous one.
  • phase separation makes the product unusable.
  • a further problem of the known emulsifiable concentrates is the difficult to obtain homogeneous emulsions, that is, emulsions where the active ingredients, for example carvacrol, are uniformly distributed in the aqueous medium and do not form concentration gradients which could compromise the effectiveness of the treatment on the plants. Therefore, there is a need of having available formulations which allow to obtain homogeneous and stable emulsions of poorly water-soluble active ingredients, in particular of carvacrol.
  • Subject-matter of the invention is a composition comprising, and alternatively consists of: a) carvacrol in an amount from 10 to 45 wt%, for example from 10 wt% to 40 wt% or from 10 to 30 wt%; b) at least one water-immiscible solvent selected from vegetable oils and esters of the vegetable oils, preferably the esters of the vegetable oils, in an amount from 20 wt% to 40 wt%; c) at least one first non-ionic surfactant selected from ethoxylated vegetable oils, in an amount from 25 wt% to 40 wt%; d) at least one sulfonated anionic surfactant; e) at least one second non-ionic surfactant selected from ethoxylated polyarylphenols, for example ethoxylated tristyrylphenol, ethoxylated alcohols, ethoxylated fatty acids, sorbitan esters and eth
  • composition of the invention allows to obtain particularly stable emulsions in water that comprise carvacrol, that is, which do not undergo a substantial phase separation once diluted in water, making their application, that is, administration to plants, impossible.
  • composition of the invention allows to obtain particularly homogeneous emulsions in water.
  • composition is an emulsifiable concentrate (EC).
  • carvacrol it is meant herein the compound of formula (I) above indicated, whether of natural origin, i.e. obtained by extraction from the plants containing it, or produced by synthesis.
  • carvacrol also includes the extracts of the plants containing carvacrol, for example the oils extracted from said plants; in this case, the amounts of carvacrol set forth herein are always referred to carvacrol and not to the amounts of extract.
  • component a) can be in an amount in the range from 10 to 45 wt%, for example from 10 wt% to 40 wt% or from 10 wt% to 30 wt%, for example from 28 wt% to 32 wt%.
  • carvacrol is in an amount from 30 wt% to 30,8 wt%.
  • carvacrol is in an amount of 30 wt%.
  • carvacrol is in an amount of 30.8 wt%.
  • the water-immiscible solvent is in an amount in the range from 20 wt% to 36 wt%, preferably from 21 wt% to 30 wt%. In embodiments, the water-immiscible solvent can be in an amount of 21 wt%, in an amount of 28 wt%, in an amount of 29 wt%, in an amount of 29.2 wt%, in an amount of 30 wt%.
  • the weight ratio between said carvacrol a) and said water-immiscible solvent b) is 1 : 0.60 - 1.30, preferably 1 : 0.70 - 1.20, for example 1 : 0.70 - 1.
  • the weight ratio between said carvacrol and said water-immiscible solvent can be 1 : 0.7, can be 1 : 0.93, can be 1 : 0.95, can be 1 : 0.967, can be 1:1, can be 1 : 1.167, can be 1:1.2.
  • the water-immiscible solvent is selected from the esters of vegetable oils.
  • Such compounds can be used as water-immiscible solvents and are preferably selected from esters of rapeseed oil (CAS n. 85586-25-0), the esters of soybean oil, the esters of palm oil, the esters of palm kernel oil, the esters of hemp oil, the esters of linseed oil, the esters of rice oil, the esters of com oil, the esters of sunflower oil, the esters of peanut oil, the esters of cotton-seed oil and mixtures thereof, preferably said esters being methyl esters.
  • the water-immiscible solvent is made of methyl esters of rapeseed oil (CAS n.
  • the water-immiscible solvent can be the product currently available in the market under the name “Radia 7961” (methyl esters of rapeseed oil, CAS n. 85586-25-0), distributed by Oleon N.V.
  • the first non-ionic surfactant is in an amount in the range from 28 wt% to 40 wt%, preferably from 28 wt% to 39 wt%.
  • the first non-ionic surfactant is selected from ethoxylated vegetable oils.
  • the first non-ionic surfactant is the ethoxylated castor oil (CAS. n. 61791-12-6).
  • the first non-ionic surfactant is ethoxylated castor oil (CAS. n. 61791-12-6), for example ethoxylated castor oil comprising from 30 to 40 units of ethylene oxide, preferably comprising from 34 to 38 units of ethylene oxide, more preferably comprising 36 units of ethylene oxide per molecule.
  • the first non- ionic surfactant can be the product currently available on the market under the name “Emulson CO/36” (Ethoxylated castor oil), distributed by Lamberti S.p.A.
  • the weight ratio between said carvacrol a) and said first non-ionic surfactant c) can be 1 : 0.60 - 1.50, preferably 1 : 0.90 - 1.30, preferably 1 : 0.93 - 1.30.
  • the weight ratio between said carvacrol and said water-immiscible solvent can be, for example, 1 : 0.93, can be 1:1, can be 1 : 1.167, can be 1 : 1.168, can be 1 : 1.30.
  • the weight ratio between said water-immiscible solvent b) and said first non-ionic surfactant c) is 1 : 0.75 - 1.75, preferably 1 : 1 - 1.75, for example 1 : 1.2 - 1.75.
  • the weight ratio between said water-immiscible solvent and said first non-ionic surfactant can be 1 : 0.75 - 1.75, preferably 1 : 1 - 1.75, for example 1 : 1.2 - 1.75.
  • the weight ratio between said water-immiscible solvent and said first non-ionic surfactant can
  • 4 be, for example, 1 : 0.8, can be 1 : 0.83, can be 1 : 1, can be 1 : 1.23, can be 1 : 1.34, can be 1 : 1.67.
  • the anionic surfactant is in an amount in the range from 0.4 wt% to 7.5 wt%; preferably from 0.5 wt% to 7 wt%, for example from 0.8 wt% to 7 wt%.
  • the anionic surfactant is selected from the sulfonated surfactants.
  • the anionic surfactant can be selected from alkylsulfonates, alkylarylsulfonates, diphenylsulfonates, alpha-olefmsulfonates, lignosulfonates, sulfonates of fatty acids, sulfonates of alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates and sulfosuccinamates.
  • the anionic surfactant can be selected from the alkyl derivatives of benzenesulfonic acid.
  • the anionic surfactant is the calcium salt of linear C10-C13 alkyl derivatives of benzenesulfonic acid (CAS n. 1335202-81-7).
  • the second non-ionic surfactant is in an amount in the range from 0.15 wt% to 3 wt%, preferably from 0.2 wt% to 2.8 wt%, for example from 0.3 wt% to 2.8 wt%.
  • the second non-ionic surfactant is selected from ethoxylated polyarylphenols, preferably ethoxylated tristyrylphenol (CAS n. 99734-09-5), ethoxylated alcohols, ethoxylated fatty acids, sorbitan esters and ethoxylated derivatives thereof, ethoxylated and/or propoxylated block copolymers, alkyl polyglycosides, organosilicon compounds and mixtures thereof.
  • the second non-ionic surfactant is the ethoxylated tristyrylphenol (CAS. n. 99734-09-5).
  • two or more surfactants of the composition can be used in pre-mixed form.
  • the anionic surfactant and at least one of the two non-ionic surfactants can be used in pre-mixed form.
  • the anionic surfactant can be used in pre-mixed form with the second non-ionic surfactant.
  • the anionic surfactant preferably linear C10-C13 alkyl derivatives of benzenesulfonic acid
  • the second non-ionic surfactant preferably ethoxylated tristyrylphenol
  • the composition comprises the product currently available on the market under the name “Geronol FF 4 E” (mixture of calcium salt of linear C10-C13 alkyl derivatives of benzenesulfonic acid (CAS n. 1335202-81-7) and ethoxylated tristyrylphenol (CAS n. 99734-09-5) in 2-ethylhexanol), distributed by Solvay Solutions Italia S.p.A.
  • the composition can include a second solvent f), preferably 2- ethylhexanol.
  • a second solvent f preferably 2- ethylhexanol.
  • such second solvent, preferably 2-ethylhexanol is in an amount from 0.3 wt% to 6 %wt, preferably from 0.4 wt% to 5.6 wt%, and for example from 0.6 wt% to 4.5 wt%.
  • the composition does not include esters of lactic acid.
  • carvacrol a) is preferably in an amount in the range from 28 wt% to 32 wt%, more preferably from 29 wt% to 31 wt%, still more preferably from 30 wt% to 30.8 wt%.
  • the water-immiscible solvent b) is preferably in an amount in the range from 21 wt% to 30 wt%.
  • the first non-ionic surfactant c) is preferably in an amount in the range from 28 wt% to 39 wt%.
  • the anionic surfactant d) in preferably in an amount in the range from 0.5% to 7%, for example from 0.8% to 7% or from 0.8 to 6%.
  • the second non-ionic surfactant e) is preferably in an amount in the range from 0.2 wt% to 2.8 wt%, for example from 0.3 wt% to 2.8 wt% or from 0.3 to 2.3 %.
  • the composition comprises: a) carvacrol in an amount in the range from 29 wt% to 31 wt%; b) at least one ester of a vegetable oil in an amount in the range from 21 wt% to 30 wt%; c) at least one ethoxylated vegetable oil in an amount in the range from 28 wt% to 39 wt%; d) at least one sulfonated surfactant in an amount in the range from 0.5 wt% to 7 wt%, for example from 0.8 wt% to 7 wt%; e) ethoxylated tristyrylphenol in an amount in the range from 0.2 wt% to 2.8 wt%, for example from 0.3 wt% to 2.8 wt%.
  • the composition comprises: a) carvacrol in an amount in the range from 29 wt% to 31 wt%; b) methyl esters of rapeseed oil in an amount in the range from 21 wt% to 30 wt%; c) ethoxylated castor oil in an amount in the range from 28 wt% to 39 wt%;
  • the composition can further comprise a second solvent f), preferably 2-ethylhexanol, in an amount from 0.3 wt% to 6 %wt, preferably from 0.4 wt% to 5.6 wt%, for example from 0.6 wt% to 4.5 wt%.
  • a second solvent f preferably 2-ethylhexanol
  • the composition comprises: a) carvacrol in an amount in the range from 30 wt% to 31 wt%; b) methyl esters of rapeseed oil in an amount in the range from 28 wt% to 30 wt%; c) ethoxylated castor oil in an amount in the range from 35 wt% to 38 wt%; d) calcium salt of linear C10-C13 alkyl derivatives of benzenesulfonic acid, preferably in an amount in the range from 1.6 wt% to 2 wt%; e) ethoxylated tristyrylphenol, preferably in an amount in the range from 0.6 wt% to 0.8 wt%, and optionally, f) 2-ethylhexanol, preferably in an amount in the range from 1.2 wt% to 1.6 wt%.
  • the weight ratio between methyl esters of rapeseed oil b) and ethoxylated castor oil c) e 1 1.60 - 1.80.
  • the weight ratio between carvacrol a) and methyl esters of rapeseed oil b) is 1 : 0.9 - 1.
  • the weight ratio between carvacrol a) and ethoxylated castor oil c) is 1 : 1.15 - 1.20.
  • the composition can be prepared by mixing, optionally in sequence, all the components, according to techniques known, per se, in the art.
  • the emulsifiable concentrated compositions are typically diluted with water to form an emulsion.
  • dilution can, for example, occur in suitable containers, such as barrels, where usually the plant protection products are diluted before the administration to plants; the dilution is carried out until obtaining a suitable concentration of the active ingredients, for example of carvacrol.
  • the emulsion is then administered to the plants by means of known methods such as, for example, foliar spray, administrations by fertigation to the soil and in the seed furrow and treatment by seed incorporation.
  • the composition of the invention is diluted with water at a concentration from 0.1 wt% to 3.0 wt% for foliar applications and soil fertigation, preferably from 0.5 wt% to 2.0 wt%, while it is used as it is for the incorporation in seed.
  • the present invention refers to an aqueous composition
  • an aqueous composition comprising the composition of the invention in an amount from 0.1 wt% to 3.0 wt%, for example from 0.5 wt% to 2.0 wt%.
  • tackifiers and/or colorants can for example be added, during the seed dressing.
  • composition of the invention can be used in combination with other plant protection products added for example in the aqueous composition described above.
  • subject-matter of the invention is the use of the concentrated composition and/or the aqueous composition to prevent or treat a variety of plant infections, in particular fungal such as, for examples but not limited to, infections by Oomycetes, Aschomycota, Basidiomycota, e.g. Pythium, V. inaequalis, P. recondita, P. viticola, P. infestans.
  • fungal such as, for examples but not limited to, infections by Oomycetes, Aschomycota, Basidiomycota, e.g. Pythium, V. inaequalis, P. recondita, P. viticola, P. infestans.
  • subject-matter of the invention is the use of the concentrated composition and/or the aqueous composition as an insecticide to kill a variety of plant pests included, but not limited to, Hemiptera, Lepidoptera, e,g, the D. plantaginea and H. armigera.
  • subject-matter of the invention is a method to prevent or treat a variety of plant infections, in particular fungal such as, for examples but not limited to, infections by Oomycetes, Aschomycota, Basidiomycota, e.g. Pythium, V. inaequalis, P. recondita, P. viticola, P. infestans, which comprises administering to the plant or crop concerned the concentrated composition and/or the aqueous composition of the invention.
  • fungal such as, for examples but not limited to, infections by Oomycetes, Aschomycota, Basidiomycota, e.g. Pythium, V. inaequalis, P. recondita, P. viticola, P. infestans
  • subject-matter of the invention is a method to provide insecticidal activity to kill a variety of plant pests included, but not limited to, Hemiptera, Lepidoptera, e,g, the D. plantaginea and H armigera. which comprises administering to the plant or crop concerned the concentrated composition and/or the aqueous composition of the invention.
  • composition of the invention allows to obtain homogeneous and particularly stable emulsions in water, that is, which do not undergo phase separation, or which do not substantially undergo a phase separation once diluted in water.
  • present "experimental section” reports experiments which demonstrate such technical effect.
  • Emmulson CO/36 Ethoxylated castor oil, distributed by Lamberti S.p.A., (amount of active ingredient: 100%)
  • “Geronol FF 4 E” mixture of calcium salt of linear C10-C13 alkyl derivatives of benzenesulfonic acid (CAS n. 1335202-81-7; amount of active ingredient >40% - ⁇ 50%) and ethoxylated tristyrylphenol (CAS n. 99734-09-5; amount of active ingredient >15%
  • Soprophor BSU ethoxylated tristyrylphenol (CAS n. 99734-09-5; amount of active ingredient >99% - ⁇ 100%), distributed by Solvay Solutions Italia S.p.A.
  • Rhodacal 60 BE mixture of calcium salt of linear C10-C13 alkyl derivatives of benzenesulfonic acid (CAS n. 1335202-81-7; amount of active ingredient >60% - ⁇ 70%) and 2-ethylhexanol CAS n. 104-76-7; amount of active ingredient >30% - ⁇ 40%).
  • amount of active ingredient it is meant the concentration of the compound specified within the commercial product.
  • the stability of the compositions has been measured by diluting each composition at 5% in CIPAC D water (water with hardness of 342 ppm), in a graduated cylinder, and by evaluating the amount of cream or oil or phase separation after 2 hours.
  • Table 1 reports the data of the compositions according to the present invention, and the respective results.
  • Table 2 reports the data of comparative compositions, and the respective results. particular, a sulfonated anionic surfactant) and do not comprise the second non-ionic surfactant (in particular, ethoxylated tristyrylphenol).
  • the comparative composition 10 shows a weight ratio between the water-immiscible solvent (methyl esters of rapeseed oil) and the first non-ionic surfactant (ethoxylated castor oil) of 1 : 0.47; and a weight ratio between carvacrol and said solvent of 1 : 1.50.
  • the comparative composition 11 shows a weight ratio between the water-immiscible solvent (methyl esters of rapeseed oil) and the first non-ionic surfactant (ethoxylated castor oil) of 1 : 2.14.
  • the comparative composition 13 does not comprise the second non-ionic surfactant (in particular, ethoxylated tristyrylphenol).
  • the comparative composition 14 does not comprise the first non-ionic surfactant, i.e. the ethoxylated castor oil.
  • compositions of the invention are particularly stable and result to be particularly useful in the use as phytosanitary agent, in particular as antifungal and/or insecticidal agricultural agent.

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  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Wood Science & Technology (AREA)
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  • Agronomy & Crop Science (AREA)
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Abstract

La présente invention concerne des compositions pour une utilisation phytosanitaire. En particulier, la présente invention concerne des formulations concentrées émulsifiables comprenant du carvacrol.
PCT/IB2022/057439 2021-08-10 2022-08-10 Composition concentrée émulsifiable comprenant du carvacrol WO2023017427A1 (fr)

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IT102021000021710A IT202100021710A1 (it) 2021-08-10 2021-08-10 Composizione concentrata emulsionabile comprendente carvacrolo e/o timolo.
IT102021000021710 2021-08-10

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