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WO2025131902A1 - Procédés de protection de plantes à l'aide de mélanges comprenant du soufre, des terpènes et des phosphites sélectionnés - Google Patents

Procédés de protection de plantes à l'aide de mélanges comprenant du soufre, des terpènes et des phosphites sélectionnés Download PDF

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WO2025131902A1
WO2025131902A1 PCT/EP2024/085587 EP2024085587W WO2025131902A1 WO 2025131902 A1 WO2025131902 A1 WO 2025131902A1 EP 2024085587 W EP2024085587 W EP 2024085587W WO 2025131902 A1 WO2025131902 A1 WO 2025131902A1
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Prior art keywords
sulfur
plant
liter
mixture
gram
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Raffaello ZITO
Ulla HILSINGER
Annett KUEHN
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BASF SE
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BASF SE
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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
    • A01N27/00—Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
    • 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
    • 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
    • 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
    • A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same 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
    • A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/02—Sulfur; Selenium; Tellurium; Compounds 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
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/26—Phosphorus; Compounds thereof
    • 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
    • A01P3/00—Fungicides

Definitions

  • the present invention relates to mixtures comprising sulfur, selected terpenes and phosphites, as well as to methods for protecting plants using such mixtures.
  • Crop plants are under constant threat by plant pathogens and plant pests. Thus, there is a constant need to develop a broad toolkit of alternative pesticides to protect crop plants and to improve on the shortcomings of existing pesticides.
  • One interest is to develop pesticides based on natural compounds, which show the same performance and ease of application as comparable pesticides based on synthetic compounds.
  • Sulfur is mainly used to protect fruits, vegetables and grapevines against phytopathogenic fungi, mites and insects, like aphids.
  • Sulfur fungicides are generally formulated as wettable powders or water dispersible granules. Sulfur wettable powder formulations are dusty and pose a risk to the user, mostly because of eye irritation, inhalation risk and skin irritation. Granular formulations are less dusty, but more expensive in production.
  • An improved formulation type are suspension concentrates.
  • water-based suspension concentrates of sulfur frequently show sedimentation during storage which is difficult to re-suspend and tend to form a supernatant serum. Sulfur particles formed during storage may block spray nozzles.
  • Another problem of water-based suspension concentrates is a low pourability and a high viscosity, which reduces the ease of application for the user of these formulations.
  • Variants of water-based suspension concentrates comprising different kinds of fatty acid or terpene-based plant oils have been described in W003/086073, which describes a composition to control grapevine powdery mildew (Uncinula necator), comprising sulfur and a 40% soybean oil in water emulsion.
  • Sulfur has limited applications in crops like wheat, barley, rye, triticale, oat, sugar and fodder beets. While sulfur protects these crops well against powdery mildews, like Blumeria graminis (also known as Erysiphe graminis), it requires high application rates of 6 to 8 kg of sulfur per hectare (ha) per treatment. Even at these high rates, sulfur shows insufficient effects against other phytopathogenic fungi of these crops. Accordingly, there is a need in the art to improve the protective effects of sulfur-based fungicides against other phytopathogenic fungi of these crops and/or to identify ways to apply sulfur in these crops which allow for a lower application rate per hectare and year.
  • Blumeria graminis also known as Erysiphe graminis
  • Terpenes are a diverse group of natural compounds and are parts of many plant essential oils. Their basic structure can be visualized as the result of linking isoprene (CsHs) units "head to tail” to form chains and rings. They are further classified depending on the amount of isoprene units used for their basic structure. Examples for these subgroups are monoterpenes, sesquiterpenes and diterpenes. Monoterpenes comprise two isoprene units and C10H16 in their basic structure, sesquiterpenes comprise three and diterpenes four isoprene units.
  • CsHs isoprene
  • WO2022/101613 describes a bio-fungicide composition comprising microencapsulated essential oils or isolated terpenes. Despite the fact, that sulfur and terpenes have been used as pesticides since a long time, it is less known about their combined effects and the conditions to achieve positive effects or to overcome technical hurdles arising from their combination.
  • WO2019/207112 describes a fungicidal mixture of limonene, cinnamaldehyde and one or more terpinenes, which can be used to replace other fungicides and thereby reduce the amount of other fungicides, like sulfur and copper, in spray regimes to protect plants. It describes that using the particular mixture in spray regimes has the potential to reduce the total amount of sulfur from 100 to 120 kg to 10 to 12 kg per season.
  • WO2016/004326 discloses a seed, soil, or plant treatment composition, comprising one or more essential oils and one or more emulsifiers, wherein the one or more essential oils are present as an emulsion and the average particle size of the one or more essential oils in the emulsion is less than about 25 microns.
  • this plant treatment composition can be combined with several pesticides, including fungicides, such as sulfur. While these documents describe effects of sulfur and terpenes for protecting plants against fungal attack, they do not describe, how these compounds can be used together, without reducing the effectiveness of sulfur against fungal or insect pests and or to avoid enhanced phytotoxicity effects based on the combination of these compounds.
  • FR2599592 describes an antifungal composition (Helio- sulfre®), comprising suspended micronized sulfur in in an emulsion of pine oil and water and one or more surfactants.
  • One liter of this suspension concentrate comprises typically 60 to 170 g of pine oil; 25 to 70 g of surfactants; 400 to 1000 g of micronized or finely ground sulfur.
  • a combination of nanoparticulated sulfur with essential orange oil has been described as Oro Solve®.
  • Cesar et al. 2019, “"Nanoparticulated Sulfur and Essential Orange Oil (Oro Solve®) Increases Efficiency of Euschistus heros Control", Egypt. Acad. J. Biolog. Sci., 12(6): 111-120, describes that Oro Solve® is composed of orange essential oil + 45% nanoparticulate elemental sulfur, giving a concentration of 585 g per liter.
  • phosphite products are not compatible with alkaline materials such as lime, sulfur or spray oils. It has also be considered, that high concentrations of sulfur usually lead to high viscosity and poor pourability of formulations, which, especially when combined with sedimentation of sulfur, can cause severe problems during preparation and application of the spraying suspension and can cause uneven application of the active compounds on the crop and blocking of valves and spray nozzles of the crop protection sprayer.
  • terpenes usually have a high vapor pressure, so that a combined action of terpenes and sulfur on the respective plant pathogen or pest may be too short lived to provide any additional positive effect for plant protection.
  • the selected terpenes can be chemically synthesized or isolated from essential plant oils. Methods to synthesize the selected terpenes are well known in the art. However, the selected terpenes can also be isolated e.g. via centrifugal separation or steam distillation from plant essential oils.
  • essential plant oil comprises one or more of limonene, terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol.
  • suitable essential plant oils are: orange oil, tangerine oil, grapefruit oil, lemon oil, mandarin oil, which comprise high amounts of D-limonene.
  • Thyme oil which usually comprises thymol with 23% to 60%, y-terpinene with 18% to 50%, p-cymene with 8% to 44% and carvacrol with 2% to 8%.
  • Oregano oil comprises high amounts of thymol and carvacrol.
  • Pinene can be isolated from pine oil.
  • P-cymene can be found in the oils of cumin and thyme.
  • Eugenol can be isolated from cinnamon oil.
  • Geraniol is a component of citronella oil, rose oil and palmarosa oil.
  • the content of a given terpene in a certain essential oil can vary and will depend on the source of the plant material, such as genotype of the plant, environmental conditions during growth of the plant, harvesting conditions of the plant material, method of extraction and other factors.
  • the limonene, terpinene, pinene, p-cymene, eugenol, geraniol, thymol or carvacrol has been isolated from an essential plant oil or is provided as part of an essential plant oil.
  • the mixtures used in the described methods may comprise only one of limonene, terpinene, pinene, p-cymene, eugenol, geraniol, thymol or carvacrol, for example only limonene, preferably D-limonene, but may also comprise more than one of the selected terpenes.
  • Preferred mixtures of the selected terpenes are: a) mixtures of limonene, preferably D-limonene, with at least one of a-terpinene, p-cymene, carvacrol, eugenol, geraniol and thymol- b) mixtures of limonene, preferably D-limonene, with at least one of a-terpinene, p-cymene and carvacrol. c) mixtures of limonene, preferably D-limonene, with at least one of eugenol, geraniol and thymol.
  • the weight/weight ratio between limonene, preferably D-limonene, and one terpene selected from terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol is between 75 to 1 and 1 to 1, or between 50 to 1 and 1 to 1, or between 25 to 1 and 1 to 1, or between 10 to 1 and 1 to 1, or between 8 to 1 to 1 to 1, or between 5 to 1 and 1 to 1 , or between 2 to 1 and 1 to 1 .
  • the weight/weight ratio between limonene, preferably D-limonene, and the combined amount of the one or more of terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol is between 75 to 1 and 1 to 1, or between 50 to 1 and 1 to 1, or between 25 to 1 and 1 to 1, or between 10 to 1 and 1 to 1, or between 8 to 1 to 1 to 1, or between 5 to 1 and 1 to 1 , or between 2 to 1 and 1 to 1.
  • mixtures of the selected terpenes are: a) mixtures of a-terpinene, p-cymene and limonene. b) mixtures of at least two of eugenol, geraniol and thymol.
  • the terpenes selected from limonene, terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol may be accompanied by other terpenes, in particular if at least one of limonene, terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol is provided as part of an essential plant oil.
  • the weight/weight ratio between the combined amounts of the terpenes, selected from limonene, terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol, and the combined amounts of other terpenes is between 75 to 1 and 1 to 1, or between 50 to 1 and 1 to 1, or between 25 to 1 and 1 to 1, or between 10 to 1 and 1 to 1, or between 8 to 1 to 1 to 1, or between 5 to 1 and 1 to 1, or between 2 to 1 and 1 to 1.
  • the weight/weight ratio between limonene, preferably D-limonene, and the combined amount of terpenes other than, terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol is between 75 to 1 and 1 to 1 , or between 50 to 1 and 1 to 1 , or between 25 to 1 and 1 to 1 , or be-tween 10 to 1 and 1 to 1 , or between 8 to 1 to 1 to 1 , or between 5 to 1 and 1 to 1 , or between 2 to 1 and 1 to 1 .
  • the weight/weight ratio between limonene, preferably D-limonene, and the combined amount of terpenes including terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol is between 75 to 1 and 1 to 1, or between 50 to 1 and 1 to 1, or between 25 to 1 and 1 to 1 , or be-tween 10 to 1 and 1 to 1 , or between 8 to 1 to 1 to 1 , or between 5 to 1 and 1 to 1 , or between 2 to 1 and 1 to 1 and preferably more than 90 to 1 or higher, 100 to 1 or higher, 300 to 1 or higher, 500 to 1 or higher or 1000 to 1 or higher.
  • phosphites are phosphorous acid and its (alkali metal or alkaline earth metal) salts such as potassium phosphites e.g. KH2PO3 and K2HPO3, sodium phosphites and ammonium phosphites, and (C-C4) alkyl esters of phosphorous acid and their salts such as aluminum ethyl phosphite (fosetyl-AI), calcium ethyl phosphite, magnesium isopropyl phosphite, magnesium isobutyl phosphite, magnesium sec-butyl phosphite and aluminum N-butyl phosphite.
  • the weight/weight ratio of a) the amount of sulfur to the combined amounts of the terpenes, selected from limonene, terpinene, pinene, p-cy- mene, eugenol, geraniol, thymol and carvacrol is between 100 to 1 and 1 to 1 , or between 70 to 1 and 1 to 1 , or between 65 to 1 and 1 to 1 , or between 50 to 1 and 1 to 1 , or between 40 to 1 and 1 to 1 , or between 30 to 1 and 1 to 1 , or between 30 to 1 and 5 to 1 , or between 25 to 1 and 1 to 1 , or between 25 to 1 and 2 to 1 , or between 25 to 1 and 3 to 1 , or between 25 to 1 and 4 to 1 , or between 25 to 1 and 5 to 1 , or between 25 to 1 and 6 to 1 , or between 25 to 1 and 7 to 1 , or between 25 to 1 and 8 to 1, or between 25 to 1 and 9 to 1, or between 15 to 1 and 7
  • Suspoemulsion and suspension concentrate formulations comprising sulfur, selected terpenes and phosphites.
  • a further embodiment of the invention are suspoemulsion and suspension concentrate formulations comprising: a) sulfur b) one or more terpenes, selected from limonene, terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol, c) phosphites, d) one or more carrier oils and e) optionally further components.
  • Agrochemical suspoemulsions are also known as "SE" type agro formulations.
  • the suspoemulsion usually comprises a continuous aqueous phase, a dispersed oil phase, and a suspended solid phase.
  • the oil phase usually forms droplets within the aqueous phase.
  • the oil phase usually comprises the water-immiscible active ingredient.
  • the oil phase usually comprises at least one pesticide, which may be dissolved in a water-immiscible solvent.
  • the solid phase usually consists of solid particles within the aqueous phase.
  • the solid phase may comprise at least one pesticidal substance, which is suspended in a continuous aqueous phase. A further pesticidal substance is dissolved in the water- immiscible solvent.
  • the further pesticidal substance is present at least in the dispersed oil phase of the suspoemulsion.
  • the first pesticidal substance is suspended in the continuous aqueous phase.
  • the first pesticidal substance is present at least in the solid phase of the suspoemulsion.
  • Agrochemical suspension concentrates typically relates to compositions, which comprise solid particles, which are homogenously dispersed in a continuous aqueous phase.
  • Agrochemical suspension concentrate is usually preformed in the commercial product and is conventionally diluted with a carrier, such as water, when making up the spray mixture (also called the tank mix).
  • the continuous aqueous phase of the suspension concentrate is usually free of other dispersed phases beside the pesticide particles.
  • the suspoemulsion and suspension concentrate formulations preferably comprise a) sulfur b) at least one terpene, selected from limonene, terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol, in a weight/weight ratio of sulfur to the combined amount of limonene, terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol and c) phosphites, in weight/weight ratios as described for the mixtures above.
  • Suitable carrier oils should have a low solubility in water.
  • a further group comprises C12 - C20 fatty alcohols, octanol, decyl alcohol, tridecanol, 2-ethylhexanol, oleyl alcohol, cetyl alcohol and lauryl alcohol.
  • the combined amount of all terpenes is preferably between 10 and 300 gram/liter, 10 and 250 gram/liter, between 10 and 200 gram/liter, between 15 and 150 gram/liter, between 20 and 150 gram/liter, between 20 and 130 gram/liter, between 20 and 70 gram/liter or between 30 and 60 gram/liter.
  • the selected terpenes and carrier oils used in the suspoemulsion or suspension concentrate formulations described in Table 1 to 3 are preferably selected limonene, a-terpinene, p-cymene, eugenol, geraniol, thymol and carvacrol and carrier oils, in particular preferred are formulations comprising a combination of limonene and methyl oleate or limonene and isopropyl myristate or limonene and one or more carrier oils selected from soybean oil, rape oil, sunflower oil, peanut oil, linseed oil, cottonseed oil, corn oil or castor oil.
  • the suspoemulsion or suspension concentrate formulations usually have a pH from 5.5 to 8.5, preferably form 6.5. to 7.5.
  • suspoemulsion or suspension concentrate formulations described herein are selected based on their good storage stability.
  • the change of the value for the percentage of sulfur particles larger than 2 micrometer, the D50, the D90 and/or the D[4;3] value should not be larger than plus or minus 15%, preferably plus or minus 10%, more preferred plus or minus 5%.
  • the change of the value for the percentage of sulfur particles larger than 2 micrometer, the D50, the D90 and/or the D[4;3] value should not be larger than plus or minus 25%, preferably plus or minus 20%, more preferred plus or minus 15%, even more preferred plus or minus 10%.
  • suspoemulsion or suspension concentrate formulations may comprise further components, such as auxiliaries known to be suitable for agrochemical formulations,.
  • auxiliaries are liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wet- ters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, antioxidants, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foam- ing agents, colorants, tackifiers and binders.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharide powders e.g. cellulose, starch
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • Antoxidants are a preferred suspension concentrate or suspoemulsion formulations, if it is intended to enhance their antioxidant capacity above the level provided by the other components, e.g. provided by terpenes which are liquid at 20°C and/or the carrier oils.
  • additional antioxidants are preferably selected from tocopherols, e.g. vanillin, a- tocopherol, ascorbic acid, ascorbate, carotenoids, e.g. beta-carotene, n-propyl gallate, butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), tert-Butylhydroquinone (TBHQ).
  • n-propyl gallate Ascorbic acid, sodium sulfite, tocopherol-acetate and butylated hydroxyanisole (BHA).
  • the antioxidant capacity can be measured by methods known in the art, for example methods discussed in Slo- anu and Apetrei, Int. J. Mol. Sci.; Analytical Methods Used in Determining Antioxidant Activity: A Review; 2021, 22, 3380. https://doi.org/10.3390/ijms22073380.
  • the suspension concentrate or suspoemulsion formulations comprise a) to f) a) 50 to 20 gram/liter of one or more dispersants (e.g. Morwet D 425, CAS 577773-56-9), and b) 50 to 20 gram/liter of one or more antifreeze (e.g. 1 ,2-Propylene glycol) and c) 50 to 1, or 50 to 20 gram/liter of one or more anionic surfactants (e.g. Wettol NT1 CAS 211565-27-4 or Wettol EM 1, CAS 26264-06-2 ) and d) 100 to 1, or 10 to 1 gram/liter of one or more nonionic surfactants (e.g.
  • one or more dispersants e.g. Morwet D 425, CAS 577773-56-9
  • antifreeze e.g. 1 ,2-Propylene glycol
  • anionic surfactants e.g. Wettol NT1 CAS 211565-27-4 or Wetto
  • biocides e.g. Acticide MV and Acticide B 20
  • antifoams e.g. SRE-PFL
  • CAS Numbers are defined by the Chemical Abstracts Service (CAS).
  • the suspension concentrate or suspoemulsion formulations comprise a) to g) and preferably also h) a) 70 to 10, or 50 to 20 gram/liter of one or more dispersants, b) 70 to 20, or 50 to 20 gram/l iter of one or more antifreeze, c) 50 to 1, or 50 to 20 gram/liter of one or more anionic surfactants, d) 100 to 1, or 10 to 1 gram/liter of one or more nonionic surfactants, e) 10 to 2, or 5 to 3 gram/liter of one or more biocides, f) 10 to 1 gram/liter of one or more antifoams, g) 10 to 1 gram/liter of one or more antioxidants, h) 10 to 1 gram/liter of one or more thickener g) 10 to 1 gram/liter of one or more antioxidants, h) 10 to 1 gram/liter of one or more thickener
  • the auxiliaries in the suspension concentrate or suspoemulsion formulations comprise auxiliaries selected from the following groups: a) fatty alcohol alkoxylates, b) silicone adjuvants, c) sulphosuccinates, or d) mixtures of at least two of a to c).
  • Preferred fatty alcohol alkoxylates are Plurafac LF 221 (CAS 208350-19-0), Plurafac LF 901 (CAS 166736-08-9), Lutensol TO 8 and Lutensol ON 60 (CAS 123897-56-3),
  • Preferred silicone adjuvants are Silwet HS 604 (CAS 2524826-13-7) and Silwet HS 312 (CAS 1012786-03-6)
  • a preferred sulphosuccinate is Lutensit A-BO (CAS 577-11-7),
  • auxiliaries selected from groups a) to c) or combinations thereof are:
  • One or more sulphosuccinates preferably at least one sulphosuccinate is a salt of bis(2-ethylhexyl) sulfosuccinate, more preferred it is sodium bis(2-ethylhexyl) sulfosuccinate, even more preferred it is Lutensit A-BO.
  • One or more fatty alcohol alkoxylates preferably at least one fatty alcohol alkoxylate is selected from Plurafac LF 221, Plurafac LF 901, Lutensol TO 8 and Lutensol ON 60.
  • One or more silicone adjuvants preferably selected from Silwet HS 604 and Silwet HS 312
  • a mixture of one or more sulphosuccinates and one or more fatty alcohol alkoxylates preferably a mixture comprising a salt of bis(2-ethylhexyl) sulfosuccinate, more preferred comprising sodium bis(2-ethylhexyl) sulfosuccinate, even more preferred comprising Lutensit A-BO.
  • Preferred fatty alcohol alkoxylates are selected from Plurafac LF 221, Plurafac LF 901, Lutensol TO 8 and Lutensol ON 60.
  • a mixture of one or more fatty alcohol alkoxylates and one or more silicone adjuvants is selected from Plurafac LF 221, Plurafac LF 901, Lutensol TO 8 and Lutensol ON 60.
  • at least one of the silicone adjuvants is selected from Silwet HS 604 and Silwet HS 312.
  • the weight/weight ratio between the combined amounts of sulphosuccinates and the combined amounts of fatty alcohol alkoxylates is between 5 to 1 and 1 to 5 or between 3 to 1 and 1 to 3 or between 2 to 1 and 1 to 2 or is 1 to 1.
  • the weight/weight ratio between the combined amounts of fatty alcohol alkoxylates and the combined amounts of silicone adjuvants is between 5 to 1 and 1 to 5 or between 3 to 1 and 1 to 3 or between 2 to 1 and 1 to 2 or is 1 to 1 .
  • the total amount of the auxiliaries selected from the following groups: fatty alcohol alkoxylates, silicone adjuvants and sulphosuccinates, in the suspension concentrate or suspoemulsion formulations, is preferably in an amount of 100 to 1 gram/liter, 80 to 1 gram/liter, 70 to 1 gram/liter, 60 to 1 gram/liter, 50 to 1 gram/liter, 40 to 1 gram/liter, 30 to 1 gram/liter, 20 to 1 gram/liter or 10 to 1 gram/liter.
  • the suspension concentrate or suspoemulsion formulations of the invention usually have a good pourability, a low viscosity and a low phytotoxicity.
  • the invention comprises a method for controlling phytopathogenic fungi selected from the genera, Erysiphe, Blumeria, Podosphaera, Septoria, Cercospora, Sclerotinia, Pyrenophora, Ramularia, Fusarium, Venturia, and Diplocarpon, comprising contacting the fungi, the plant or the plant parts to be protected against fungal attack with a fungicidally effective amount of a mixture comprising sulfur, at least one terpene, selected from limonene, terpinene, pinene, p- cymene, eugenol, geraniol, thymol and carvacrol and at least one phosphite, wherein the weight/weight ratio of the amount of sulfur to the combined amounts of the selected terpenes, is between 100 to 1 and 1 to 1, or between 70 to
  • More preferred at least one fungus is from a species selected from: Puccinia triticina, Puccinia striiformis, Erysiphe graminis, Septoria tritici, Cercospora beticola, Cercospora sojina, Sclerotinia sclerotiorum, Ramularia collo-cygni and Fusarium graminearum.
  • the mixture is applied when the phytopathogenic fungi is present or infections are likely due to the weather conditions.
  • the invention comprises also a method for controlling or reducing Fusarium head blight (FHB) in wheat, barley, rye or oat, comprising a) identifying a plant or a plurality of plants infected or in danger of being infected by Fusarium head blight and b) contacting the fungi, the plant or the plant parts infected or in danger of being infected by Fusarium head blight with a fungicidally effective amount of a mixture comprising sulfur, at least one terpene, selected from limonene, terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol, and at least one phosphite, wherein the weight/weight ratio of the amount of sulfur to the combined amounts of the selected terpenes, is between 100 to 1 and 1 to 1 , or between 70 to 1 and 1 to 1, or between 65 to 1 and 1 to 1 , or
  • At least one of the selected terpenes is limonene, preferably D-limonene, wherein the weight/weight ratio between sulfur and limonene is between 100 to 1 and 1 to 1 , or between 70 to 1 and 1 to 1 , or between 65 to 1 and 1 to 1 , or between 50 to 1 and 1 to 1 , or between 40 to 1 and 1 to 1 , or between 30 to 1 and 1 to 1, or between 30 to 1 and 5 to 1 , or between 25 to 1 and 1 to 1, or between 25 to 1 and 2 to 1 , or between 25 to 1 and 3 to 1 , or between 25 to 1 and 4 to 1, or between 25 to 1 and 5 to 1, or between 25 to 1 and 6 to 1 , or between 25 to 1 and 7 to 1 , or between 25 to 1 and 8 to 1 , or between 25 to 1 and 9 to 1 , or between 15 to 1 and 7 to 1, or between 12 to 1 and 7 to 1 , or between 10 to 1 and 7 to 1 , or between 12 to 1 and 8 to 1 , or between
  • Fusarium head blight is caused by several species of the fungal genus Fusarium.
  • Fusarium graminearum is the species that causes the most serious damage to crops.
  • Fungi of the genus Fusarium are known to produce mycotoxins.
  • Fusarium graminearum frequently produces zearalenone and trichothecenes, such as nivalenol, deox- ynivalenol (DON) and/or acetylated derivatives of DON such as 3-acetyl-DON and 15-acetyl-DON.
  • Fungi of the genus Cercospora are known to produce mycotoxins called cercosporins.
  • the phytopathogenic fungi of the genus Puccinia are preferably selected from the species Puccinia triticina, Puccinia graminis f. sp. avenae, Puccinia graminis f. sp. poae, Puccinia graminis f. sp. secalis, Puccinia graminis f. sp. tritici, Puccinia graminis subsp. graminicola, Puccinia helianthi, Puccinia hordei, Puccinia sorghi, Puccinia striiformis f. sp. hordei and Puccinia striiformis f. sp. tritici.
  • the phytopathogenic fungi are from the species Puccinia triticina.
  • the phytopathogenic fungi of the genus Podosphaera are preferably selected from the species Podosphaera fuligi- nea, Podosphaera leucotricha, Podosphaera clandestina, Podosphaera pannosa, Podosphaera tridactyla, Podosphaera xanthii, Podosphaera mors-uvae and Podosphaera aphanis or are selected from Podosphaera leucotricha, Podosphaera clandestina, Podosphaera pannosa, Podosphaera tridactyla, Podosphaera xanthii, Podosphaera mors- uvae and Podosphaera aphanis.
  • the phytopathogenic fungi are from the species Blumeria graminis.
  • the phytopathogenic fungi of the genus Septoria are preferably selected from the species Zymoseptoria tritici, also known as Septoria tritici, Septoria betae, Septoria glycines, Septoria helianthi and Septoria secalis. In one embodiment the phytopathogenic fungi are from the species Zymoseptoria tritici.
  • the phytopathogenic fungi of the genus Sclerotinia are preferably selected from the species Sclerotinia sclerotiorum.
  • the phytopathogenic fungi of the genus Ramularia are preferably selected from the species Ramularia collo-cygni and Ramularia beticola. In one embodiment the phytopathogenic fungi are from the species Ramularia collo-cygni.
  • the plant or the plant parts to be protected is from the genus Triticum, preferably of the species Triticum aestivum or Triticum durum, more preferred from the species Triticum aestivum, and the phytopathogenic fungi is from a species selected from Puccinia triticina, Puccinia graminis f. sp. tritici, Puccinia striiformis f. sp. tritici, Erysiphe graminis, Blumeria graminis f. sp. tritici, Zymoseptoria tritici and Pyrenophora tritici-repenti.
  • the plant or the plant parts are protected from Puccinia triticina and Erysiphe graminis. More preferred, the plant or the plant parts are protected from Puccinia triticina, Erysiphe graminis, and at least one of Zymoseptoria tritici and Pyrenophora tritici-repentis.
  • the plant or the plant parts to be protected is from the species Hordeum vulgare and the phytopathogenic fungi is from a species selected from Pyrenophora teres, Blumeria graminis f. sp. hordei and Ramularia collo-cygni.
  • the plant or the plant parts are protected from at leat two of Pyrenophora teres, Blumeria graminis f. sp. hordei and Ramularia collo-cygni.
  • the plant or the plant parts to be protected is from the species Secale cereale and the phytopathogenic fungi is from a species selected from Puccinia graminis f. sp. secalis, Blumeria graminis f. sp. secalis and Septoria secalis.
  • the plant or the plant parts are protected from Puccinia graminis f. sp. secalis and Blumeria graminis f. sp. secalis.
  • the plant or the plant parts to be protected is from the species Zea mays and the phytopathogenic fungi is from a species selected from Puccinia sorghi and Cercospora zeae-maydis.
  • the plant or the plant parts to be protected is from the species Beta vulgaris and the phytopathogenic fungi is from a species selected from Cercospora beticola, Septoria betae and Ramularia beticola.
  • the plant or the plant parts are protected from Cercospora beticola and at least one of Septoria betae and Ramularia beticola.
  • the plant or the plant parts to be protected is from the species Brassica napus and the phytopath- ogenic fungi is from a species selected from Sclerotinia sclerotiorum and Erysiphe cruciferarum.
  • the plant or the plant parts are protected from Sclerotinia sclerotiorum.
  • the plant or the plant parts to be protected is from the species Glycine max and the phytopatho- genic fungi is from a species selected from Cercospora kikuchii, Cercospora sojina, Septoria glycines and Sclerotinia sclerotiorum.
  • the plant or the plant parts are protected from Sclerotinia sclerotiorum. or Cercospora sojina.
  • the plant or the plant parts to be protected is from the species Solanum tuberosum and the phy- topathogenic fungi is from a species selected from Erysiphe cichoracearum, Cercospora concors, Cercospora solani, Cercospora solani-tuberosi, and Sclerotinia sclerotiorum.
  • the plant or the plant parts are protected from Sclerotinia sclerotiorum.
  • the plant or the plant parts to be protected is from the species Helianthus annuus and the phyto- pathogenic fungi is from a species selected from Puccinia helianthi, Septoria helianthi, and Sclerotinia sclerotiorum.
  • the plant or the plant parts are protected from Sclerotinia sclerotiorum.
  • the plant or the plant parts to be protected is from the genus Triticum, Hordeum, Secale or Zea, preferably of the species Triticum aestivum, Triticum durum, Hordeum vulgare, Secale cereale or Zea mays, more preferred from the species Triticum aestivum, and the phytopathogenic fungi is from a species selected from the genus Fusarium, preferably from the species Fusarium graminearum, Fusarium culmorum, Fusarium avenaceum, Fusarium verticilloides, Fusarium oxysporum and Fusarium poae, more preferred from the species Fusarium graminearum.
  • the plant or the plant parts to be protected is from the genus Malus, preferably of the species Ma- lus domestica and the phytopathogenic fungi is from the species Venturia inaequalis, Podosphaera leucotricha.or Diplocarpon mali.
  • the plant or the plant parts to be protected is from the genus Pyrus, preferably of the species Py- rus communis or Pyrus pyrifolia and the phytopathogenic fungi is from the species Venturia pyrina, Venturia nash- icola or Diplocarpon mespili.
  • the plant or the plant parts to be protected is from the genus Malus, Prunus, Pyrus or Olea, preferably of the species Malus domestica, Prunus persica, Prunus domestica, Prunus domestica, Prunus armeniaca, Prunus avium, Prunus cerasus, Pyrus pyrifolia, Pyrus communis or Olea europaea, and the phytopathogenic fungi is from a species selected from the genus Venturia, preferably of the species Venturia inaegualis, Venturia carpophila, Venturia cerasi, Venturia nashicola, Venturia pyrina, or Venturia oleaginea.
  • the plant or the plant parts to be protected is from banana or plantain and the phytopathogenic fungi is from a species selected from Mycosphaerella fiijiensis, Mycosphaerella musicola, Cercospora hayi, Sclerotinia sclerotiorum, or Septoria eumusae.
  • the plant species named above are understood to comprise all subspecies, variants, varieties and/or hybrids which belong to the respective plant species, including but not limited to winter and spring varieties, in particular in cereals such as wheat and barley, as well as oilseed rape, e.g. winter wheat, spring wheat, winter barley etc, further including dwarf, semi-dwarf and full-dwarf varieties and/or hybrids with reduced height and thicker and shorter stems.
  • Corn is also known as Indian corn or maize (Zea mays) which comprises all kinds of corn such as field corn and sweet corn.
  • all soybean cultivars or varieties are comprised, in particular indeterminate and determinate cultivars or varieties.
  • the mixtures may be combined with biopesticides.
  • the biopesticides may be added to the mixtures as a tank mix to prepare the spraying suspensions or may be directly added as integral part of the agrochemical formulation comprising the mixtures.
  • the biopesticides can be applied to the fungi, the plant or the plant parts to be protected against fungal attack shortly before or after the spraying suspension comprising the mixtures is applied.
  • biopesticides can be used in combination with the mixtures described herein.
  • the list is intended to illustrate the possible combinations but does not limit them:
  • Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity Ampelo- myces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. amyloliquefaciens ssp. plantarum (also referred to as B. velezensis), B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var. amyloliquefaciens, B.
  • the mixtures described above are the mixtures described above to be used in the methods for controlling phy- topathogenic fungi.
  • the mixtures comprise sulfur, at least one terpene, selected from limonene, terpinene, pinene, p-cymene, eugenol, geraniol, thymol and carvacrol and at least one phosphite, wherein the weight/weight ratio of the amount sulfur to the combined amounts of the selected terpenes, is between 100 to 1 and 1 to 1, or between 70 to 1 and 1 to 1, or between 65 to 1 and 1 to 1, or between 50 to 1 and 1 to 1, or between 40 to 1 and 1 to 1, or between 30 to 1 and 1 to 1 , or between 30 to 1 and 5 to 1 , or between 25 to 1 and 1 to 1 , or between 25 to 1 and 2 to 1 , or between 25 to 1 and 3 to 1 , or between 25 to 1 and 4 to 1 , or between 25 to 1 and 5 to 1 , or between 25 to 1
  • the mixtures are comprised in agrochemical formulations, which are then diluted with water to prepare the spraying suspensions.
  • agrochemical formulations which are then diluted with water to prepare the spraying suspensions.

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Abstract

La présente invention concerne des mélanges comprenant du soufre, des terpènes et des phosphites sélectionnés ainsi que des procédés de protection de plantes utilisant de tels mélanges.
PCT/EP2024/085587 2023-12-21 2024-12-11 Procédés de protection de plantes à l'aide de mélanges comprenant du soufre, des terpènes et des phosphites sélectionnés Pending WO2025131902A1 (fr)

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