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WO2025068079A1 - Compositions and methods for repelling birds from plants and plant propagation materials - Google Patents

Compositions and methods for repelling birds from plants and plant propagation materials Download PDF

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Publication number
WO2025068079A1
WO2025068079A1 PCT/EP2024/076576 EP2024076576W WO2025068079A1 WO 2025068079 A1 WO2025068079 A1 WO 2025068079A1 EP 2024076576 W EP2024076576 W EP 2024076576W WO 2025068079 A1 WO2025068079 A1 WO 2025068079A1
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WO
WIPO (PCT)
Prior art keywords
bird
compound
plant propagation
seed
tas2r4
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.)
Pending
Application number
PCT/EP2024/076576
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French (fr)
Inventor
Matthias GABERTHUEEL
Maik Behrens
Silvia SCHAEFER
Tatjana LANG
Olivier Loiseleur
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.)
Syngenta Crop Protection AG Switzerland
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Syngenta Crop Protection AG Switzerland
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Publication of WO2025068079A1 publication Critical patent/WO2025068079A1/en
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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N45/00Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01PBIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P17/00Pest repellants

Definitions

  • the present invention relates to compositions, formulations and methods that are useful for repelling birds from plants, more particularly preventing or reducing damage to plant propagation materials, in particular seeds, by birds.
  • bird deterrent techniques including visual deterrents (such as scarecrows, lasers or reflective tape) and auditory deterrents (including propane cannons and sonic or ultrasonic scarers). Since long, growers of agricultural crops have also treated their crops with bird-repelling agents to ward off pillaging birds.
  • bird-repelling agents to plants or their propagations materials, such as their seeds, is appealing, as these agents are, by definition, non-lethal to birds and are actually delivered to the target pest, i.e., the bird that feeds on the plant or seed.
  • a bird-repellent composition comprising a compound (A) that activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7.
  • the compound (A) activates two, preferably three, preferably four, and more preferably all bird taste receptors selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7.
  • these compounds are cholic acid or cholic acid derivatives.
  • the compounds that activate multiple bird taste receptors selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7 are compounds containing at least one tryptophan (Trp) and at most six tryptophan moieties, such as tritryptophan.
  • the invention pertains to a bird repellent composition
  • cholic acid A-1) taurolithocholic acid (A-3): or tritryptophan (A-4): or combinations thereof.
  • the invention is also directed to a seed treatment formulation comprising the bird-repellent composition as described herein.
  • the invention also encompasses method for preventing or reducing damage to plants and plant propagation materials, in particular seeds, by a bird, wherein said method comprises treating the plant or plant propagation material with a composition as disclosed herein.
  • the invention is further directed to the use of the compounds and compositions as defined herein for repelling birds from plants and plant propagation materials.
  • the invention relates to plant propagation materials, particularly seeds treated with the composition of the invention.
  • compositions and methods described herein are aimed at keeping birds from feeding on plants and their propagation material. These compositions and methods can be applied to many types of plants and propagation materials.
  • the active ingredient(s) of the invention is a compound (A) that activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7, or combinations of such compounds.
  • Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7 are members of the bitter taste receptor family, T2R (TAS2R or Tas2r), which has been found in a variety of species.
  • TAS2R genes encode bitter taste receptors, which are G-protein coupled receptors (GPCRs) located primarily on the surface of taste bud cells in the tongue. These receptors allow humans and other animals to detect and respond to bitter substances, a trait that is believed to have evolved as a protective mechanism to prevent the ingestion of potentially toxic substances, many of which taste bitter. It has been established previously that different animal species respond differently to individual bitter compounds.
  • the invention provides a bird-repellent composition
  • a bird-repellent composition comprising a compound (A) that activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7.
  • A a compound that activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7.
  • binding of the particular compound to the Tas2r1 , Tas2r3, Tas2r4, Tas2r5 and/or Tas2r7 receptor triggers a cascade of cellular events signalling the perception of a bitter taste; in addition to the likely immediate physiological reaction to the perception of a bitter taste of quitting consumption (or even spitting out) of the treated plant material, there may be the development of an aversion to consume the plant material in the future.
  • the composition comprises a compound (A) that activates at least one of the aforementioned bird taste receptors.
  • a compound (A) that activates at least one of the aforementioned bird taste receptors.
  • the composition comprises a compound (A) that activates the following two bird taste receptors: Tas2r1 and Tas2r3; Tas2r1 and Tas2r4; Tas2r1 and Tas2r5; Tas2r1 and Tas2r7; Tas2r3 and Tas2r4; Tas2r3 and Tas2r5; Tas2r3 and Tas2r7; Tas2r4 and Tas2r5; Tas2r4 and Tas2r7; or Tas2r5 and Tas2r7.
  • A that activates the following two bird taste receptors: Tas2r1 and Tas2r3; Tas2r1 and Tas2r4; Tas2r1 and Tas2r5; Tas2r1 and Tas2r7; Tas2r3 and Tas2r4; Tas2r3 and Tas2r5; Tas2r4 and Tas2r7; or Tas2r5 and Tas2r7.
  • the composition comprises a compound (A) that activates the following three bird taste receptors: Tas2r1 , Tas2r3, and Tas2r4; Tas2r1 , Tas2r3, and Tas2r5; Tas2r1 , Tas2r3, and Tas2r7; Tas2r1 , Tas2r4, and Tas2r5; Tas2r1 , Tas2r4, and Tas2r7;Tas2r3, Tas2r4, and Tas2r5;
  • A that activates the following three bird taste receptors: Tas2r1 , Tas2r3, and Tas2r4; Tas2r1 , Tas2r3, and Tas2r5; Tas2r1 , Tas2r3, and Tas2r7; Tas2r1 , Tas2r4, and Tas2r7;
  • Tas2r3, Tas2r4, and Tas2r7 are Tas2r3, Tas2r4, and Tas2r7; or Tas2r4, Tas2r5, and Tas2r7
  • the composition comprises a compound (A) that activates the following four bird taste receptors: Tas2r1 , Tas2r3, Tas2r4 and Tas2r5; Tas2r1 , Tas2r3, Tas2r4 and Tas2r7;
  • the composition comprises a compound (A) that activates all five bird taste receptors Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7.
  • cholic acid derivative means in the context of the present invention that one or more functional groups such as, e.g., hydroxyl, halo, (halo)alkyl, or aminoalkyl, may be present on one or more of the A, B, C and D rings of the cholic acid sterol skeleton, and/or that the heptanoic acid functionality is modified with, e.g., an ester, aminoalkyl, amidoalkyl, or alkylsulphonic acid functionality.
  • one or more functional groups such as, e.g., hydroxyl, halo, (halo)alkyl, or aminoalkyl
  • the invention of pertains to a bird repellent composition
  • a bird repellent composition comprising a compound (A) that activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7, wherein compound (A) is a compound containing from 1 to 6 tryptophan moieties.
  • the invention of pertains to a bird repellent composition
  • a bird repellent composition comprising a compound (A) that activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7, wherein compound (A) is cholic acid or a cholic acid derivative.
  • compound (A) is cholic acid or a cholic acid derivative. It has furthermore been found that certain specific compounds containing from 1 to 6 tryptophan moieties as well as cholic acid and cholic acid derivatives are each individually active on more than one Tas2r1 , Tas2r3, Tas2r4, Tas2r5 and/or Tas2r7 receptors in birds.
  • cholic acid derivatives that are individually active on multiple Tas2r1 , Tas2r3, Tas2r4, Tas2r5 and/or Tas2r7 receptors in birds are glycocholic acid and taurolithocholic acid.
  • the invention pertains to a bird repellent composition
  • a bird repellent composition comprising cholic acid (A-1) or a derivative thereof.
  • a bird repellent composition comprising glycocholic acid (A-2):
  • a bird repellent composition comprising taurolithocholic acid (A- 3):
  • a bird repellent composition comprising a cholic acid derivative, different from A-1 , A-2 and A-3, such as for example lithocholic acid (A-3’):
  • a tryptophan-containing compound that is individually active on multiple Tas2r1 , Tas2r3, Tas2r4, Tas2r5 and/or Tas2r7 receptors in birds is tritryptophan (A-4):
  • the invention pertains to a bird repellent composition comprising tritryptophan.
  • aspects of the invention also pertain to a bird repellent composition
  • a bird repellent composition comprising a combination of two or more of compounds A-1 , A-2, A-3 and A-4.
  • the compounds cholic acid (CAS 81-25-4), glycocholic acid (CAS 475-31-0), taurolithocholic acid (CAS 516-90-5), lithocholic acid (CAS 434-13-9), and tritryptophan (CAS 59005-82-2) as well as their syntheses are known in the art.
  • the bird-repellent composition may comprise one or more auxiliaries and/or diluents and/or additional active ingredients, as will be described in more detail below.
  • the bird-repellent composition according to the invention is used in methods for treating crop plants and plant propagation materials in order to prevent or reduce damage to the plants and their propagation materials, in particular seeds, caused by birds.
  • treated and “treating” of the plant or plant propagation material with birdrepellent composition may refer to the process of applying to or covering, coating, dressing, overspreading, or overlaying the plant, or parts of the plant or the locus thereof, or its propagation material with the composition as defined in any one of embodiments according to the invention.
  • the term “damage to plants and plant propagation materials” may refer to any one of the following nuisances inflicted by birds: direct seed consumption; seedling damage caused by pulling seedlings for consumption; root damage resulting from digging in soil for insects or roots; stripping of mature cereals; feeding on flowers or buds; pecking of fruits and vegetables; breaking of nut shells; contamination by bird droppings; and transmission of diseases.
  • the bird-repellent composition is used for treating plant propagation materials, more particularly seeds.
  • a seed treatment formulation comprising the bird-repellent composition according to the invention.
  • plant propagation material can be understood to denote all generative parts of a plant, such as seeds, which can be used for the multiplication of the latter including vegetative plant material such as cuttings.
  • vegetative plant material such as cuttings.
  • plant propagation material seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, parts of plants.
  • the plant propagation material can be treated with the active ingredients) of the invention before the material is sown or planted.
  • the plant propagation material may be treated with the active ingredient(s) of the invention during sowing or planting. Additionally, the active ingredient(s) of the invention may be applied to the previously treated propagation material before or during its planting. The active ingredient(s) of the invention may be applied during the sowing of the seed. The active ingredients) may also be used to plant propagation material derived from plants grown in a green house and/or during transplantation. More preferably the plant propagation material is plant seeds.
  • the seeds may also still be present on the plant that produces them, for example when they have matured and have not yet been harvested. Such seeds may be directly exposed, such as seeds of cereals or of sunflower, or they may be borne by, or embedded in, a fruit. Both types of seeds are concerned with the invention. According to a particular embodiment, the seeds according to the invention are seeds that are present in a field in which they are placed for being grown or in which they have been grown, in which latter case the seeds are present on the ripening plants.
  • the invention also relates to a field comprising seeds treated with a composition according to the invention.
  • the compounds and compositions according to the invention can be used in combination with other active ingredients, including pesticides such as insecticides, herbicides, acaricides, nematicides, fungicides, or agents that enhance the activity of the composition according to the invention, in for example chemical treatment or pest control programs.
  • pesticides such as insecticides, herbicides, acaricides, nematicides, fungicides, or agents that enhance the activity of the composition according to the invention, in for example chemical treatment or pest control programs.
  • the combination may have further surprising advantages.
  • the bird-repellent composition of the present invention forms part of a pesticidal composition comprising one or more pesticidal compounds such as insecticides, herbicides, acaricides, nematicides, and/or fungicides.
  • pesticidal compounds such as insecticides, herbicides, acaricides, nematicides, and/or fungicides.
  • the bird-repellent composition of the present invention is applied separately to the plant or plant propagation material, optionally preceded and/or followed by the application of other active ingredients.
  • the bird-repellent composition of the present invention comprises as a further active ingredient a compound (B), wherein compound (B) is selected from acibenzolar-s-methyl, metalaxyl-M, metalaxyl, picarbutrazox, oxathiapiprolin, ethaboxam, fludioxonil, azoxystrobin, thiabendazole, difenoconazole, tebuconazole, ipconazole, mefentrifluconazole, prothioconazole, triticonazole, sedaxane, inpyrfluxam, penflufen, fluopyram, fluxapyroxad, pydiflumetofen, cyclobutrifluram, thiamethoxam, isocycloseram, isoflucypram, clothianidin, benzovindiflupyr, cymoxanil, phosphite (phosphon
  • the bird-repellent composition of the present invention comprises a compound (A) as defined herein and a compound (B) selected from metalaxyl-M, picarbutrazox, fludioxonil, tefluthrin, thiamethoxam, isocycloseram, cyclobutrifluram, cyantraniliprole, chlorantraniliprole, fluoxastrobin and prothioconazole, or combinations thereof.
  • a compound (B) selected from metalaxyl-M, picarbutrazox, fludioxonil, tefluthrin, thiamethoxam, isocycloseram, cyclobutrifluram, cyantraniliprole, chlorantraniliprole, fluoxastrobin and prothioconazole, or combinations thereof.
  • the weight ratio of compound (A) to compound (B) is in the range of 1 :500 to 500:1 , preferably 1 :100 to 100:1 , more preferably 1 :10 to 10:1.
  • the weight ratio of compound (A) to compound (B) is 25:1 , 20:1 , 16:1 , 10:1 , 8:1 , 6:1 , 5:1 , 4:1 , 3.2:1 , 3:1 , 2:1 , 1.5:1 , 1.25:1 , 1 :1 , 1 :1.25, 1 :1.5, 1 :2, 1 :3, 1 :3.2, 1 :4, 1 :5, 1 :8, 1 :10, 1 :16, 1 :20 or 1 :25.
  • compositions and formulations may additionally include non-active ingredients in some amount.
  • the compositions and formulations may include surfactants, solvents (e.g., water and/or other solvents), thickeners, preservatives (including bactericides and other biocides), humectants, antifreeze ingredients, antifoam ingredients and if appropriate colorants, or other additives.
  • the rates of application of the bid-repellent compounds, compositions and formulations of the present invention may vary within wide limits and depend on the nature of the soil, the method of application (pre- or post-emergence, seed dressing, application to the seed furrow, no tillage application etc.), the crop plant, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop.
  • the composition or formulation comprising the composition of the invention is typically applied at a rate corresponding to 0.01 to 2 mg of compound (A) per plant propagation material (e.g. seed), and preferably 0.2 to 1 mg of compound (A) per plant propagation material (e.g. seed).
  • the rate of application is between 0.0005 and 150 g of compound (A) per kg of seed, preferably between 0.005 and 100 g of compound (A) per kg of seed, and more preferably between 0.05 and 50 g of compound (A) per kg of seed. In specific examples, the rate of application is between 0.5 and 10 g of compound (A) per kg of seed.
  • composition or formulation comprising the composition of the invention is typically applied at a rate from 100 g to 4000 g/ha of compound (A), and preferably from 500 g to 1000 g/ha of compound (A).
  • the invention also pertains to a coated plant propagation material, preferably a seed, wherein the coating comprises a composition as defined in any one of embodiments according to the invention.
  • the compositions and formulations comprising such compositions are repellent and/or unpalatable to birds whose food is made, partially or entirely, of plants and their propagation materials, particularly seeds. Such birds are usually referred to as seed-eating birds or granivorous birds. According to such embodiment, the invention is most useful against birds feeding on crop seeds.
  • birds feeding on crop seeds include, but are not limited to, from the family Corvidae, more specifically of the genus Corvus, e.g. Corvus splendens, Corvus frugilegus, Corvus corone, and Corvus monedula. from the family Columbidae, more specifically of the genus Columba, e.g. Columba palumbus, Columba livia, Streptopelia decaocto;
  • compositions and formulations of the invention are used for repelling blackbirds (Turdus merula), crows (Corvus spp.), grackles (Quiscalus spp.), pheasants (Phasianus spp.), and/or starlings (Stumus vulgaris).
  • a further aspect of the invention pertains to a method for preventing or reducing damage to plants or plant propagation materials, in particular seeds, by a bird, wherein said method comprises treating the plant propagation material with a composition as defined in any one of embodiments according to the invention.
  • the method for preventing or reducing damage to plant propagation materials by birds encompasses prohibiting birds from feeding on newly planted crops.
  • the method for preventing or reducing damage to plant propagation materials by birds encompasses prohibiting birds from feeding on freshly sowed seeds.
  • the invention also pertain to the use of a compound which activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7, as a bird repellent.
  • the invention pertains to the use of a compound selected from cholic acid (CAS 81-25-4), glycocholic acid (CAS 475-31-0), taurolithocholic acid (CAS 516-90-5) and tritryptophan (CAS 59005- 82-2), or a combination thereof, as a bird repellent.
  • the above uses and methods exclude treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
  • Birds can cause damage to a variety of crops. The extent of damage may vary based on the type of bird, the stage of crop growth, and the region. Examples of crops that can be treated with the composition of the present invention include, - cereals such as wheat, barley, rye, oats, rice, maize (corn), sorghum, maize, millet, and triticale;
  • oilseed rape canola
  • mustard poppies
  • olives sunflowers
  • coconut castor
  • cocoa ground nuts
  • peanuts cucurbits like pumpkins, cucumbers, and melons
  • fibre plants including cotton, flax, hemp, jute, and sisal;
  • grasses such as Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass, and Zoysia grass;
  • vines such as grapes are also suitable target crops.
  • Crops are to be understood as being those which are naturally occurring, obtained by conventional methods of breeding, or obtained by genetic engineering. They include crops which contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour).
  • output traits e.g. improved storage stability, higher nutritional value and improved flavour.
  • crops is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
  • the seeds treated as described herein include seeds of corn (maize), cereals (such as wheat, barley, oat, rye, spelt) soybeans, rape, rice, sugar beet, cotton, millet varieties such as sorghum, sun flowers, beans, peas, oil plants such as canola, rape, soybeans, cabbages, tomatoes, eggplants (aubergines), pepper and other vegetables and spices as well as ornamental shrubs and flowers.
  • Suitable target crops also include transgenic crop plants of the foregoing.
  • the seed is from maize, sunflower, or cereal, particularly wheat or barley.
  • the seed treatment can occur to an unsown seed, and the term "unsown seed” is meant to include seed at any period between the harvest of the seed and the sowing of the seed in the ground for the purpose of germination and growth of the plant. Treatment to an unsown seed is not meant to include those practices in which the pesticide is applied to the soil but would include any application practice that would target the seed during the sowing/planting process.
  • the treated plant propagation material of the present invention can be treated in the same manner as conventional plant propagation material.
  • the treated propagation material can be stored, handled, sown and tilled in the same manner as any other pesticide treated material.
  • the term “locus” as used herein means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.
  • the compositions and formulations comprising the active ingredients) as defined herein can be advantageously in the form of a soluble concentrate (SL), or a flowable concentrate for seed treatment (FS), or a suspension concentrate (SC), and can be more preferably a seed treatment slurry to be applied onto seeds.
  • Slurries for seed treatment applications are well-known in the art.
  • a slurry can contain the active ingredient(s), in the form of a commercially available product or not, mixed with water and optionally with at least one polymer as described in the present invention, to optimize adhesion around the plant propagation material.
  • Preferred formulations can have the following compositions (weight %):
  • Flowable concentrate for seed treatment active ingredient: 1 to 75 %, preferably 10 to 50 % water: 98 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 30 %, preferably 2 to 20 %
  • Suspension concentrates active ingredient: 5 to 75 %, preferably 10 to 50 % water 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 %
  • Soluble concentrate active ingredient: 1 to 95 %, preferably 10 to 80 % liquid carrier: 5 to 99 %, preferably 20 to 90 %
  • Suspension concentrate The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • FS Flowable concentrate for seed treatment
  • the finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • Solution of any required dilution which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • Each active ingredient can be applied to the plant propagation material from different compositions respectively, or the active ingredients can be gathered in the same composition (ready-mix composition).
  • the composition may contain from about 0.001 % to about 99% by weight of the active ingredients) over the total weight of the composition.
  • the composition contains from about 0.001 % to about 50% by weight active ingredient(s) over the total weight of the composition. More suitably, the composition contains from about 0.001 % to about 10% by weight active ingredient(s) over the total weight of the composition. More suitably, the composition contains from about 0.001 % to about 1 % by weight active ingredient(s) over the total weight of the composition. If the formulation is in the form of a concentrate, requiring dilution with water before use, it will contain a higher amount of active ingredients than a composition that is ready to use without dilution.
  • the solid carrier can be a natural or synthetic solid material that is insoluble in water.
  • This carrier is generally inert and acceptable in agriculture, especially on the treated seed or other propagation material. It can be chosen, for example, from clay, diatomaceous earth, natural or synthetic silicates, titanium dioxide, magnesium silicate, aluminum silicate, talc, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, limestone, calcium carbonate, calcium montmorillonite, bentonite clay, Fuller's earth, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin, and the like.
  • the active ingredients) of the invention and more preferably the composition ⁇ ) comprising the active ingredient(s), can preferably adhere to the propagation material, such as a seed.
  • the present method can be applied to a seed in any physiological state, it is preferred that the seed be in a sufficiently durable state that it incurs no damage during the treatment process.
  • the seed would be a seed that had been harvested from the field; removed from the plant; and separated from any cob, stalk, outer husk, and surrounding pulp or other non-seed plant material.
  • the seed would preferably also be biologically stable to the extent that the treatment would cause no biological damage to the seed. It is believed that the treatment can be applied to the seed at any time between harvest of the seed and sowing of the seed or during the sowing process (seed directed applications).
  • compositions and formulations according to the present invention can be called a dressing composition, which relates to a liquid composition useful for covering and/or wetting a plant propagation material, and more preferably a seed, at least in part or in totality.
  • compositions and formulations according to the present invention are particularly suited for dressing applications on plant propagation material, especially on seeds.
  • compositions and formulations according to the present invention can be applied to seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful.
  • the seeds may be pre-sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art and are set out in more detail below.
  • the compositions and formulations of the invention can be applied to the seed as slurry or a soak. There also may be mentioned, e.g., film coating or encapsulation.
  • the coating processes are well known in the art, and employ, for seeds, the techniques of film coating or encapsulation, or for the other multiplication products, the techniques of immersion. More particularly, the treatment could vary from a thin film of the formulation containing the composition of the invention on a plant propagation material, such as a seed, where the original size and/or shape are recognizable to a thick film (such as a coating or pelleting with many layers of different materials (such as carriers, for example, clays; different formulations, such as of active ingredients; polymers; and colorants)) where the original shape and/or size of the seed is no longer recognizable.
  • a plant propagation material such as a seed
  • a thick film such as a coating or pelleting with many layers of different materials (such as carriers, for example, clays; different formulations, such as of active ingredients; polymers; and colorants)) where the original shape and/or size of the seed is no longer recognizable.
  • compositions and formulations according to the invention encompasses spraying or wetting the plant propagation material with the aqueous liquid preparation, or mixing the plant material with such liquid preparation. Also, before the application, the composition of the invention may be diluted with water by simple mixing at ambient temperature in order to prepare an on-farm seed treatment formulation.
  • a tank-mix formulation for seed treatment application comprises 0.25 % to 80 % by weight, especially 1 to 75 % by weight, of active ingredient(s), and 99.75 % to 20 % by weight, especially 99 % to 25 % by weight, of a solid or liquid auxiliary (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40 % by weight, especially 0.5 to 30 % by weight, based on the total weight of the tank-mix formulation.
  • a solid or liquid auxiliary including, for example, a solvent such as water
  • a pre-mix formulation for seed treatment application comprises 0.5 to 99.9 % by weight, especially 1 to 95 % by weight, of active ingredient(s), and 99.5 to 0.1 % by weight, especially 99 to 5 % by weight, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 % by weight, especially 0.5 to 40 % by weight, based on the total weight of the pre-mix formulation.
  • a solid or liquid adjuvant including, for example, a solvent such as water
  • the formulation is a flowable concentrate for seed treatment (FS) formulation comprising 10 wt% to 60wt % of active ingredient(s), preferably from 40 to 50 wt% by total weight of the formulation.
  • FS flowable concentrate for seed treatment
  • Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7 receptors were isolated from blood samples of rooks (Corvus frugilegus).
  • Bitter taste receptors can be functionally expressed in mammalian cell lines to characterize their activation spectra (Meyerhof W, Tble J, Born S, Behrens M. Prortest processor Kurs Auffinden vonesmodulatoren. Aktuel. Ernaehrungsmed. 2013;38-.30-36).
  • the cDNAs of the receptors were cloned into an expression vector that contains a sequence coding for the first 45 amino acids of the rat somatostatin receptor subtype-3 (sst3-tag) (Ammon C, Schafer J, Kreuzer OJ, Meyerhof W. Presence of a plasma membrane targeting sequence in the amino-terminal region of the rat somatostatin receptor 3. Arch Physiol Biochem. 2002;110:137-45). This sequence was added to the 5’-end of the receptor cDNA and served as export-epitope (Bufe et al. 2002).
  • the expression vector contains a herpes simplex virus glycoprotein D epitope which is added to the 3’-end and can be used for immunofluorescent detection of the receptors.
  • the cells had been engineered to constitutively express the chimeric G protein Ga16gust44 (Ueda T, Ugawa S, Yamamura H, Imaizumi Y, Shimada S. Functional interaction between T2R taste receptors and G- protein alpha subunits expressed in taste receptor cells. J Neurosci. 2003;23:7376-80).
  • the cell line HEK 293T-Ga16gust44 were a gift from J. Slack (Givaudan Inc.).
  • the compounds tested were cholic acid (Calbiochem), glycocholic acid (Sigma-Aldrich), Tauro- lithocholic acid (Cayman Chemical), and tritryptophan (Bachem).
  • the cells were then transiently transfected using Lipofectamine 2000 (0.3pL Lipofectamine 2000 + 150ng plasmid DNA per well). Besides the receptor cDNAs, empty expression vector was transfected as a negative control (mock). After 5 h the transfection was stopped by exchanging the medium to regular growth medium and the cells were further incubated for ⁇ 24 h under standard culture conditions. At the next day the cells were loaded with the calcium-sensitive dye Fluo4- am in the presence of 2.5 mM probenecid for 30min in the dark. Cells were then washed with C1 buffer using a BioTek cell washer and subsequently stored in the dark for 30 min at room temperature.

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Abstract

The present invention relates to a bird-repellent composition, particularly a bird-repellent composition comprising a compound that activates at least one bird taste receptor selected from Tas2r1, Tas2r3, Tas2r4, Tas2r5, and Tas2r7, to the use thereof in methods for repelling birds from plants and plant propagation materials. The invention is further directed to seed treatment formulations and their use in preventing or reducing damage to plants or plant propagation materials caused by birds.

Description

COMPOSITIONS AND METHODS FOR REPELLING BIRDS FROM PLANTS AND PLANT PROPAGATION MATERIALS
Field of the invention
The present invention relates to compositions, formulations and methods that are useful for repelling birds from plants, more particularly preventing or reducing damage to plant propagation materials, in particular seeds, by birds.
Introduction
Protecting plant crops, including their propagation materials, from damage caused by birds feeding on them is a vital concern for farmers, given the significant economic losses bird damage can incur. Whilst birds play a crucial role in controlling harmful insects and rodents, they may also cause drastic decrease in crop yields by damaging them during their sowing, seedling, and ripening stages. Besides reduced yields, damage inflicted by birds may also result in the crops appearing less attractive, as well as the crops to become more susceptible to infestation by other pests, such as fungal diseases.
To mitigate these issues, farmers employ various bird deterrent techniques, including visual deterrents (such as scarecrows, lasers or reflective tape) and auditory deterrents (including propane cannons and sonic or ultrasonic scarers). Since long, growers of agricultural crops have also treated their crops with bird-repelling agents to ward off pillaging birds. The concept of applying bird-repelling agents to plants or their propagations materials, such as their seeds, is appealing, as these agents are, by definition, non-lethal to birds and are actually delivered to the target pest, i.e., the bird that feeds on the plant or seed.
Unfortunately, at present very few reliable bird-repellent solutions are available.
Hence, there is need to provide new compositions and methods for controlling or preventing damage to plants, in particular plant propagation materials, caused by birds. Accordingly, it is an object of the present invention to provide new compositions and methods for repelling birds from crop plants and plant propagation materials, particularly seeds.
It is a particular object of the present invention to provide a seed-applied bird repellent that prevents birds from feeding on freshly sowed crops, such as maize (corn), sunflower, and cereals crops.
It is another object to provide bird-repellent compositions and formulations that are easy to apply, are non-lethal to birds and are environmentally friendly.
Summary of the invention
It has now surprisingly been found that certain compounds are very effective in keeping birds from feeding on plants and their propagation materials. More specifically, it has been found that certain specific compounds and compositions comprising these compounds are capable of rendering plants and their propagation materials unpalatable or repellent to birds by activating one or more specific bird taste sensors that are associated with bitter taste.
Accordingly, in a first aspect of the present invention there is provided a bird-repellent composition comprising a compound (A) that activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7. Surprisingly, it was found that compounds that activate at least one of these specific bitter taste receptors in birds, when applied to crop plants and plant propagation materials, particularly seeds thereof, cause these birds to stop feeding on them. In favourable cases, the compounds and compositions of the invention cause birds to learn to stop eating the crop treated with it and even prefer to starve.
In some examples, the compound (A) activates two, preferably three, preferably four, and more preferably all bird taste receptors selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7. In certain embodiments, these compounds are cholic acid or cholic acid derivatives. In other specific embodiments, the compounds that activate multiple bird taste receptors selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7 are compounds containing at least one tryptophan (Trp) and at most six tryptophan moieties, such as tritryptophan.
In a particular aspect the invention pertains to a bird repellent composition comprising cholic acid (A-1)
Figure imgf000003_0002
taurolithocholic acid (A-3):
Figure imgf000003_0001
or tritryptophan (A-4):
Figure imgf000004_0001
or combinations thereof.
The invention is also directed to a seed treatment formulation comprising the bird-repellent composition as described herein.
The invention also encompasses method for preventing or reducing damage to plants and plant propagation materials, in particular seeds, by a bird, wherein said method comprises treating the plant or plant propagation material with a composition as disclosed herein.
The invention is further directed to the use of the compounds and compositions as defined herein for repelling birds from plants and plant propagation materials.
In another aspect the invention relates to plant propagation materials, particularly seeds treated with the composition of the invention.
Detailed description
The compositions and methods described herein are aimed at keeping birds from feeding on plants and their propagation material. These compositions and methods can be applied to many types of plants and propagation materials.
The active ingredient(s) of the invention is a compound (A) that activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7, or combinations of such compounds. Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7 are members of the bitter taste receptor family, T2R (TAS2R or Tas2r), which has been found in a variety of species. TAS2R genes encode bitter taste receptors, which are G-protein coupled receptors (GPCRs) located primarily on the surface of taste bud cells in the tongue. These receptors allow humans and other animals to detect and respond to bitter substances, a trait that is believed to have evolved as a protective mechanism to prevent the ingestion of potentially toxic substances, many of which taste bitter. It has been established previously that different animal species respond differently to individual bitter compounds.
In an embodiment, the invention provides a bird-repellent composition comprising a compound (A) that activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7. Without wishing to be bound by theory, it is believed that activation of at least one TAS2R gene upon consumption of a crop plant or propagation material treated with the composition, leading to the perception by the bird of a bitter taste, results in the composition acting as a deterrent or repellent to the bird. More specifically, it is considered that binding of the particular compound to the Tas2r1 , Tas2r3, Tas2r4, Tas2r5 and/or Tas2r7 receptor triggers a cascade of cellular events signalling the perception of a bitter taste; in addition to the likely immediate physiological reaction to the perception of a bitter taste of quitting consumption (or even spitting out) of the treated plant material, there may be the development of an aversion to consume the plant material in the future.
In order to be effective as a bird-repellent composition, the composition comprises a compound (A) that activates at least one of the aforementioned bird taste receptors. However, it is preferred that at least two, preferably three, preferably four, and more preferably all, of the receptors selected among Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7, are activated by the compound.
Thus, in some embodiments, the composition comprises a compound (A) that activates the following two bird taste receptors: Tas2r1 and Tas2r3; Tas2r1 and Tas2r4; Tas2r1 and Tas2r5; Tas2r1 and Tas2r7; Tas2r3 and Tas2r4; Tas2r3 and Tas2r5; Tas2r3 and Tas2r7; Tas2r4 and Tas2r5; Tas2r4 and Tas2r7; or Tas2r5 and Tas2r7.
In some embodiments, the composition comprises a compound (A) that activates the following three bird taste receptors: Tas2r1 , Tas2r3, and Tas2r4; Tas2r1 , Tas2r3, and Tas2r5; Tas2r1 , Tas2r3, and Tas2r7; Tas2r1 , Tas2r4, and Tas2r5; Tas2r1 , Tas2r4, and Tas2r7;Tas2r3, Tas2r4, and Tas2r5;
Tas2r3, Tas2r4, and Tas2r7; or Tas2r4, Tas2r5, and Tas2r7
In some embodiments, the composition comprises a compound (A) that activates the following four bird taste receptors: Tas2r1 , Tas2r3, Tas2r4 and Tas2r5; Tas2r1 , Tas2r3, Tas2r4 and Tas2r7;
Tas2r3, Tas2r4, Tas2r5 and Tas2r7; Tas2r1 , Tas2r3, Tas2r5 and Tas2r7; or Tas2r1 , Tas2r4, Tas2r5 and Tas2r7.
In some embodiments, the composition comprises a compound (A) that activates all five bird taste receptors Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7.
It has been found that in particular compounds containing from 1 to 6 tryptophan moieties are active on Tas2r1 , Tas2r3, Tas2r4, Tas2r5 and/or Tas2r7 receptor in birds. It has further been found that cholic acid and cholic acid derivatives are active on Tas2r1 , Tas2r3, Tas2r4, Tas2r5 and/or Tas2r7 receptor in birds.
The term “cholic acid derivative” means in the context of the present invention that one or more functional groups such as, e.g., hydroxyl, halo, (halo)alkyl, or aminoalkyl, may be present on one or more of the A, B, C and D rings of the cholic acid sterol skeleton, and/or that the heptanoic acid functionality is modified with, e.g., an ester, aminoalkyl, amidoalkyl, or alkylsulphonic acid functionality.
In another embodiment, the invention of pertains to a bird repellent composition comprising a compound (A) that activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7, wherein compound (A) is a compound containing from 1 to 6 tryptophan moieties.
Hence, in an embodiment, the invention of pertains to a bird repellent composition comprising a compound (A) that activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7, wherein compound (A) is cholic acid or a cholic acid derivative. It has furthermore been found that certain specific compounds containing from 1 to 6 tryptophan moieties as well as cholic acid and cholic acid derivatives are each individually active on more than one Tas2r1 , Tas2r3, Tas2r4, Tas2r5 and/or Tas2r7 receptors in birds.
Examples of cholic acid derivatives that are individually active on multiple Tas2r1 , Tas2r3, Tas2r4, Tas2r5 and/or Tas2r7 receptors in birds are glycocholic acid and taurolithocholic acid.
Hence, in an aspect the invention pertains to a bird repellent composition comprising cholic acid (A-1)
Figure imgf000006_0001
or a derivative thereof.
In a particular aspect there is provided a bird repellent composition comprising glycocholic acid (A-2):
Figure imgf000006_0002
In another particular aspect there is provided a bird repellent composition comprising taurolithocholic acid (A- 3):
Figure imgf000006_0003
In another particular aspect there is provided a bird repellent composition comprising a cholic acid derivative, different from A-1 , A-2 and A-3, such as for example lithocholic acid (A-3’):
Figure imgf000006_0004
An example of a tryptophan-containing compound that is individually active on multiple Tas2r1 , Tas2r3, Tas2r4, Tas2r5 and/or Tas2r7 receptors in birds is tritryptophan (A-4):
Figure imgf000007_0001
Hence, in an aspect the invention pertains to a bird repellent composition comprising tritryptophan.
Aspects of the invention also pertain to a bird repellent composition comprising a combination of two or more of compounds A-1 , A-2, A-3 and A-4.
The compounds cholic acid (CAS 81-25-4), glycocholic acid (CAS 475-31-0), taurolithocholic acid (CAS 516-90-5), lithocholic acid (CAS 434-13-9), and tritryptophan (CAS 59005-82-2) as well as their syntheses are known in the art.
The bird-repellent composition may comprise one or more auxiliaries and/or diluents and/or additional active ingredients, as will be described in more detail below.
The bird-repellent composition according to the invention is used in methods for treating crop plants and plant propagation materials in order to prevent or reduce damage to the plants and their propagation materials, in particular seeds, caused by birds.
As used herein, the term “treated” and “treating” of the plant or plant propagation material with birdrepellent composition may refer to the process of applying to or covering, coating, dressing, overspreading, or overlaying the plant, or parts of the plant or the locus thereof, or its propagation material with the composition as defined in any one of embodiments according to the invention.
In the context of the present disclosure, the term “damage to plants and plant propagation materials” may refer to any one of the following nuisances inflicted by birds: direct seed consumption; seedling damage caused by pulling seedlings for consumption; root damage resulting from digging in soil for insects or roots; stripping of mature cereals; feeding on flowers or buds; pecking of fruits and vegetables; breaking of nut shells; contamination by bird droppings; and transmission of diseases.
Besides reduced yields, these adverse events may cause the crops to become more susceptible to infestation by other pests, such as fungal diseases.
In a particular aspect, the bird-repellent composition is used for treating plant propagation materials, more particularly seeds. Accordingly, in another aspect there is provided a seed treatment formulation comprising the bird-repellent composition according to the invention. In the present invention, the term "plant propagation material” can be understood to denote all generative parts of a plant, such as seeds, which can be used for the multiplication of the latter including vegetative plant material such as cuttings. There may be mentioned, as plant propagation material, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, parts of plants. The plant propagation material can be treated with the active ingredients) of the invention before the material is sown or planted. Alternatively, the plant propagation material may be treated with the active ingredient(s) of the invention during sowing or planting. Additionally, the active ingredient(s) of the invention may be applied to the previously treated propagation material before or during its planting. The active ingredient(s) of the invention may be applied during the sowing of the seed. The active ingredients) may also be used to plant propagation material derived from plants grown in a green house and/or during transplantation. More preferably the plant propagation material is plant seeds.
The seeds may also still be present on the plant that produces them, for example when they have matured and have not yet been harvested. Such seeds may be directly exposed, such as seeds of cereals or of sunflower, or they may be borne by, or embedded in, a fruit. Both types of seeds are concerned with the invention. According to a particular embodiment, the seeds according to the invention are seeds that are present in a field in which they are placed for being grown or in which they have been grown, in which latter case the seeds are present on the ripening plants.
Hence, in an aspect the invention also relates to a field comprising seeds treated with a composition according to the invention.
Generally, the compounds and compositions according to the invention can be used in combination with other active ingredients, including pesticides such as insecticides, herbicides, acaricides, nematicides, fungicides, or agents that enhance the activity of the composition according to the invention, in for example chemical treatment or pest control programs. The combination may have further surprising advantages.
In an exemplary embodiment, the bird-repellent composition of the present invention forms part of a pesticidal composition comprising one or more pesticidal compounds such as insecticides, herbicides, acaricides, nematicides, and/or fungicides.
In another exemplary embodiment, the bird-repellent composition of the present invention is applied separately to the plant or plant propagation material, optionally preceded and/or followed by the application of other active ingredients.
In some embodiments, the bird-repellent composition of the present invention comprises as a further active ingredient a compound (B), wherein compound (B) is selected from acibenzolar-s-methyl, metalaxyl-M, metalaxyl, picarbutrazox, oxathiapiprolin, ethaboxam, fludioxonil, azoxystrobin, thiabendazole, difenoconazole, tebuconazole, ipconazole, mefentrifluconazole, prothioconazole, triticonazole, sedaxane, inpyrfluxam, penflufen, fluopyram, fluxapyroxad, pydiflumetofen, cyclobutrifluram, thiamethoxam, isocycloseram, isoflucypram, clothianidin, benzovindiflupyr, cymoxanil, phosphite (phosphonate), silthiofam, pyraclostrobin, isotianil, tolprocarb, quinofumelin, ipflufenoquin, metyltetraprole, florylpicoxamid, fenpicoxamid, fluoxytioconazole, fluindapyr, fluoxapiprolin, broflanilide, imidacloprid, acetamiprid, cyantraniliprole, chlorantraniliprole, tetraniliprole, fluxamethamide, penthiopyrad, mandipropamid, dimpropyridaz, flupyrimin, triflumezopyrim, oxazosulfyl, dichlobentiazox, benzpirimoxan, hymexazol, pyrapropoyne, cyclaniliprole, mandestrobin, copper, lambda-cyhalothrin, phenamacril, abamectin, tefluthrin, picoxystrobin, spiropidion, oligosaccharins, Melaleuca alternifolia, fosthiazate, fenamifos, oxamyl, fluensulfone, fluazanindolizine, spirotetramat, spidoxamat, fluazinam, indazapyroxamet, thiophanate methyl, zoxamide, fluoxastrobin, pirimifos, tetrachlorantraniliprole, bifenthrin, and emamectin, or combinations thereof.
In some embodiments, the bird-repellent composition of the present invention comprises a compound (A) as defined herein and a compound (B) selected from metalaxyl-M, picarbutrazox, fludioxonil, tefluthrin, thiamethoxam, isocycloseram, cyclobutrifluram, cyantraniliprole, chlorantraniliprole, fluoxastrobin and prothioconazole, or combinations thereof.
Typically, the weight ratio of compound (A) to compound (B) is in the range of 1 :500 to 500:1 , preferably 1 :100 to 100:1 , more preferably 1 :10 to 10:1. In some embodiments, the weight ratio of compound (A) to compound (B) is 25:1 , 20:1 , 16:1 , 10:1 , 8:1 , 6:1 , 5:1 , 4:1 , 3.2:1 , 3:1 , 2:1 , 1.5:1 , 1.25:1 , 1 :1 , 1 :1.25, 1 :1.5, 1 :2, 1 :3, 1 :3.2, 1 :4, 1 :5, 1 :8, 1 :10, 1 :16, 1 :20 or 1 :25.
The compositions and formulations may additionally include non-active ingredients in some amount. For example, the compositions and formulations may include surfactants, solvents (e.g., water and/or other solvents), thickeners, preservatives (including bactericides and other biocides), humectants, antifreeze ingredients, antifoam ingredients and if appropriate colorants, or other additives.
The rates of application of the bid-repellent compounds, compositions and formulations of the present invention may vary within wide limits and depend on the nature of the soil, the method of application (pre- or post-emergence, seed dressing, application to the seed furrow, no tillage application etc.), the crop plant, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop.
When used in a seed treatment, the composition or formulation comprising the composition of the invention is typically applied at a rate corresponding to 0.01 to 2 mg of compound (A) per plant propagation material (e.g. seed), and preferably 0.2 to 1 mg of compound (A) per plant propagation material (e.g. seed).
In certain examples, the rate of application is between 0.0005 and 150 g of compound (A) per kg of seed, preferably between 0.005 and 100 g of compound (A) per kg of seed, and more preferably between 0.05 and 50 g of compound (A) per kg of seed. In specific examples, the rate of application is between 0.5 and 10 g of compound (A) per kg of seed.
When used in soil application or in-furrow application, the composition or formulation comprising the composition of the invention is typically applied at a rate from 100 g to 4000 g/ha of compound (A), and preferably from 500 g to 1000 g/ha of compound (A).
The invention also pertains to a coated plant propagation material, preferably a seed, wherein the coating comprises a composition as defined in any one of embodiments according to the invention. In an aspect of the invention, the compositions and formulations comprising such compositions, are repellent and/or unpalatable to birds whose food is made, partially or entirely, of plants and their propagation materials, particularly seeds. Such birds are usually referred to as seed-eating birds or granivorous birds. According to such embodiment, the invention is most useful against birds feeding on crop seeds.
Examples of birds feeding on crop seeds include, but are not limited to, from the family Corvidae, more specifically of the genus Corvus, e.g. Corvus splendens, Corvus frugilegus, Corvus corone, and Corvus monedula. from the family Columbidae, more specifically of the genus Columba, e.g. Columba palumbus, Columba livia, Streptopelia decaocto;
From the family Phasianidae, more specifically of the genus Phasianus, e.g. Phasianus colchicus, or of the genus Perdix, Perdix perdix; from the family Turdidae, more specifically of the genus Turdus, e.g. Turdus merula;
Stum us vulgaris, Passer domesticus, Agelaius phoeniceus, Quiscalus quiscula from the family Antatidae, more specifically of the genus Anas, e.g. Anas platyrhynchos and the genus Anser , e.g. Anser answer.
In some aspects, the compositions and formulations of the invention are used for repelling blackbirds (Turdus merula), crows (Corvus spp.), grackles (Quiscalus spp.), pheasants (Phasianus spp.), and/or starlings (Stumus vulgaris).
A further aspect of the invention pertains to a method for preventing or reducing damage to plants or plant propagation materials, in particular seeds, by a bird, wherein said method comprises treating the plant propagation material with a composition as defined in any one of embodiments according to the invention.
In a preferred embodiment, the method for preventing or reducing damage to plant propagation materials by birds encompasses prohibiting birds from feeding on newly planted crops.
In a preferred embodiment, the method for preventing or reducing damage to plant propagation materials by birds encompasses prohibiting birds from feeding on freshly sowed seeds.
The invention also pertain to the use of a compound which activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7, as a bird repellent.
In an aspect, the invention pertains to the use of a compound selected from cholic acid (CAS 81-25-4), glycocholic acid (CAS 475-31-0), taurolithocholic acid (CAS 516-90-5) and tritryptophan (CAS 59005- 82-2), or a combination thereof, as a bird repellent.
In an embodiment, the above uses and methods exclude treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.
Birds can cause damage to a variety of crops. The extent of damage may vary based on the type of bird, the stage of crop growth, and the region. Examples of crops that can be treated with the composition of the present invention include, - cereals such as wheat, barley, rye, oats, rice, maize (corn), sorghum, maize, millet, and triticale;
- leguminous crops like beans, lentils, peas, and soybean;
- oil crops such as oilseed rape (canola), mustard, poppies, olives, sunflowers, coconut, castor, cocoa, ground nuts, and peanuts; cucurbits like pumpkins, cucumbers, and melons; fibre plants including cotton, flax, hemp, jute, and sisal;
- grasses such as Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass, and Zoysia grass;
- palms, for example oil palm;
- ornamentals including flowers, shrubs, and trees;
- vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, bell peppers, broccoli, garlic, marrow, okra, pumpkin, and rhubarb. Additionally, vines such as grapes are also suitable target crops.
Crops are to be understood as being those which are naturally occurring, obtained by conventional methods of breeding, or obtained by genetic engineering. They include crops which contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour).
The term "crops" is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
In one embodiment, the seeds treated as described herein include seeds of corn (maize), cereals (such as wheat, barley, oat, rye, spelt) soybeans, rape, rice, sugar beet, cotton, millet varieties such as sorghum, sun flowers, beans, peas, oil plants such as canola, rape, soybeans, cabbages, tomatoes, eggplants (aubergines), pepper and other vegetables and spices as well as ornamental shrubs and flowers. Suitable target crops also include transgenic crop plants of the foregoing. In one embodiment, the seed is from maize, sunflower, or cereal, particularly wheat or barley.
The seed treatment can occur to an unsown seed, and the term "unsown seed" is meant to include seed at any period between the harvest of the seed and the sowing of the seed in the ground for the purpose of germination and growth of the plant. Treatment to an unsown seed is not meant to include those practices in which the pesticide is applied to the soil but would include any application practice that would target the seed during the sowing/planting process.
The treated plant propagation material of the present invention can be treated in the same manner as conventional plant propagation material. The treated propagation material can be stored, handled, sown and tilled in the same manner as any other pesticide treated material.
In the present invention, the term “locus” as used herein means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation. According to the present invention, the compositions and formulations comprising the active ingredients) as defined herein can be advantageously in the form of a soluble concentrate (SL), or a flowable concentrate for seed treatment (FS), or a suspension concentrate (SC), and can be more preferably a seed treatment slurry to be applied onto seeds. Slurries for seed treatment applications are well-known in the art. For example, a slurry can contain the active ingredient(s), in the form of a commercially available product or not, mixed with water and optionally with at least one polymer as described in the present invention, to optimize adhesion around the plant propagation material.
Preferred formulations can have the following compositions (weight %):
Flowable concentrate for seed treatment: active ingredient: 1 to 75 %, preferably 10 to 50 % water: 98 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 30 %, preferably 2 to 20 %
Suspension concentrates: active ingredient: 5 to 75 %, preferably 10 to 50 % water 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 %
Soluble concentrate: active ingredient: 1 to 95 %, preferably 10 to 80 % liquid carrier: 5 to 99 %, preferably 20 to 90 %
The following Examples further illustrate, but do not limit, the invention.
Suspension concentrate (SC)
Figure imgf000012_0001
The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
Flowable concentrate for seed treatment (FS)
Figure imgf000013_0001
The finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
Soluble concentrate (SL)
Figure imgf000013_0002
Solution of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.
Each active ingredient can be applied to the plant propagation material from different compositions respectively, or the active ingredients can be gathered in the same composition (ready-mix composition). The composition may contain from about 0.001 % to about 99% by weight of the active ingredients) over the total weight of the composition. Suitably, the composition contains from about 0.001 % to about 50% by weight active ingredient(s) over the total weight of the composition. More suitably, the composition contains from about 0.001 % to about 10% by weight active ingredient(s) over the total weight of the composition. More suitably, the composition contains from about 0.001 % to about 1 % by weight active ingredient(s) over the total weight of the composition. If the formulation is in the form of a concentrate, requiring dilution with water before use, it will contain a higher amount of active ingredients than a composition that is ready to use without dilution.
The solid carrier can be a natural or synthetic solid material that is insoluble in water. This carrier is generally inert and acceptable in agriculture, especially on the treated seed or other propagation material. It can be chosen, for example, from clay, diatomaceous earth, natural or synthetic silicates, titanium dioxide, magnesium silicate, aluminum silicate, talc, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, limestone, calcium carbonate, calcium montmorillonite, bentonite clay, Fuller's earth, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin, and the like.
Accordingly, the active ingredients) of the invention, and more preferably the composition^) comprising the active ingredient(s), can preferably adhere to the propagation material, such as a seed.
Although it is believed that the present method can be applied to a seed in any physiological state, it is preferred that the seed be in a sufficiently durable state that it incurs no damage during the treatment process. Typically, the seed would be a seed that had been harvested from the field; removed from the plant; and separated from any cob, stalk, outer husk, and surrounding pulp or other non-seed plant material. The seed would preferably also be biologically stable to the extent that the treatment would cause no biological damage to the seed. It is believed that the treatment can be applied to the seed at any time between harvest of the seed and sowing of the seed or during the sowing process (seed directed applications).
The compositions and formulations according to the present invention can be called a dressing composition, which relates to a liquid composition useful for covering and/or wetting a plant propagation material, and more preferably a seed, at least in part or in totality.
The compositions and formulations according to the present invention are particularly suited for dressing applications on plant propagation material, especially on seeds.
The techniques of seed treatment application are well known to those skilled in the art, and they may be used readily in the context of the present invention.
The compositions and formulations according to the present invention can be applied to seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful. The seeds may be pre-sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art and are set out in more detail below. The compositions and formulations of the invention can be applied to the seed as slurry or a soak. There also may be mentioned, e.g., film coating or encapsulation. The coating processes are well known in the art, and employ, for seeds, the techniques of film coating or encapsulation, or for the other multiplication products, the techniques of immersion. More particularly, the treatment could vary from a thin film of the formulation containing the composition of the invention on a plant propagation material, such as a seed, where the original size and/or shape are recognizable to a thick film (such as a coating or pelleting with many layers of different materials (such as carriers, for example, clays; different formulations, such as of active ingredients; polymers; and colorants)) where the original shape and/or size of the seed is no longer recognizable.
One method of applying the compositions and formulations according to the invention encompasses spraying or wetting the plant propagation material with the aqueous liquid preparation, or mixing the plant material with such liquid preparation. Also, before the application, the composition of the invention may be diluted with water by simple mixing at ambient temperature in order to prepare an on-farm seed treatment formulation.
Typically, a tank-mix formulation for seed treatment application comprises 0.25 % to 80 % by weight, especially 1 to 75 % by weight, of active ingredient(s), and 99.75 % to 20 % by weight, especially 99 % to 25 % by weight, of a solid or liquid auxiliary (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40 % by weight, especially 0.5 to 30 % by weight, based on the total weight of the tank-mix formulation.
Typically, a pre-mix formulation for seed treatment application comprises 0.5 to 99.9 % by weight, especially 1 to 95 % by weight, of active ingredient(s), and 99.5 to 0.1 % by weight, especially 99 to 5 % by weight, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 % by weight, especially 0.5 to 40 % by weight, based on the total weight of the pre-mix formulation.
In an embodiment, the formulation is a flowable concentrate for seed treatment (FS) formulation comprising 10 wt% to 60wt % of active ingredient(s), preferably from 40 to 50 wt% by total weight of the formulation.
Whereas commercial products will preferably be formulated as concentrates (e.g., pre-mix composition (formulation)), the end user will normally employ dilute formulations (e.g., tank mix composition).
Biological examples
Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7 receptors were isolated from blood samples of rooks (Corvus frugilegus). Bitter taste receptors can be functionally expressed in mammalian cell lines to characterize their activation spectra (Meyerhof W, Tble J, Born S, Behrens M. Rezeptortestverfahren zum Auffinden von Geschmacksmodulatoren. Aktuel. Ernaehrungsmed. 2013;38-.30-36). In order to achieve expression at the cell surface, the cDNAs of the receptors were cloned into an expression vector that contains a sequence coding for the first 45 amino acids of the rat somatostatin receptor subtype-3 (sst3-tag) (Ammon C, Schafer J, Kreuzer OJ, Meyerhof W. Presence of a plasma membrane targeting sequence in the amino-terminal region of the rat somatostatin receptor 3. Arch Physiol Biochem. 2002;110:137-45). This sequence was added to the 5’-end of the receptor cDNA and served as export-epitope (Bufe et al. 2002). Moreover, the expression vector contains a herpes simplex virus glycoprotein D epitope which is added to the 3’-end and can be used for immunofluorescent detection of the receptors. To effectively couple the receptors to the intracellular calcium signaling cascade, the cells had been engineered to constitutively express the chimeric G protein Ga16gust44 (Ueda T, Ugawa S, Yamamura H, Imaizumi Y, Shimada S. Functional interaction between T2R taste receptors and G- protein alpha subunits expressed in taste receptor cells. J Neurosci. 2003;23:7376-80). The cell line HEK 293T-Ga16gust44 were a gift from J. Slack (Givaudan Inc.).
The compounds tested were cholic acid (Calbiochem), glycocholic acid (Sigma-Aldrich), Tauro- lithocholic acid (Cayman Chemical), and tritryptophan (Bachem).
The functional experiments were done as previously published (e.g. Lang T, Lang R, Di Pizio A, Mittermeier V, Schlagbauer V, Hofmann T, Behrens M. Numerous compounds orchestrate coffee’s bitterness. J. Agric. Food Chem. 2020;68:6692-6700; Lang R, Lang T, Dunkel A, Ziegler F, Behrens M. Overlapping activation pattern of bitter taste receptors affect sensory adaptation and food perception. Front. Nutr. 2022;9:1082698). For the experiment cells were plated onto 96-well plates (black with clear bottom) treated with 10pg/mL poly-D-lysine to increase adhesion and incubated under normal conditions overnight. The cells were then transiently transfected using Lipofectamine 2000 (0.3pL Lipofectamine 2000 + 150ng plasmid DNA per well). Besides the receptor cDNAs, empty expression vector was transfected as a negative control (mock). After 5 h the transfection was stopped by exchanging the medium to regular growth medium and the cells were further incubated for ~24 h under standard culture conditions. At the next day the cells were loaded with the calcium-sensitive dye Fluo4- am in the presence of 2.5 mM probenecid for 30min in the dark. Cells were then washed with C1 buffer using a BioTek cell washer and subsequently stored in the dark for 30 min at room temperature. After a second wash with C1 buffer the 96-well plates were placed in a fluorometric imaging plate reader (FLIPRTETRA) where automated test compound application occurred and the changes in fluorescence upon substance application were monitored. A second application of somatostatin-14 served as vitality control. Using the software Screenworks 4.2, the data were mock subtracted and exported to Microsoft Excel for initial calculations of the relative changes in fluorescence (AF/F). If full dose-response relationships were measured, the calculations of ECso-concentrations were done with SigmaPlot software.
The results are summarized in the table 1 below. “X” denotes activated receptors. The threshold concentrations (defined as lowest substance concentration that results in statistically significant responses of receptor expressing cells compared to cells transfected with empty expression vector) in pM (micromolar) are provided between parentheses. Table 1 : Receptor response in rook (Corvus frugilegus)
Figure imgf000017_0001

Claims

1. A method for preventing or reducing damage to plants or plant propagation materials by a bird, wherein said method comprises applying to the plant propagation material a bird-repellent composition comprising a compound (A) that activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7.
2. The method of claim 1 , wherein compound (A) activates two, preferably three, preferably four, and more preferably all bird taste receptors selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7.
3. The method of claim 2, wherein compound (A) activates bird taste receptors Tas2r1 and Tas2r3; Tas2r1 and Tas2r4; Tas2r1 and Tas2r5; Tas2r1 and Tas2r7; Tas2r3 and Tas2r4; Tas2r3 and Tas2r5; Tas2r3 and Tas2r7; Tas2r4 and Tas2r5; Tas2r4 and Tas2r7; or Tas2r5 and Tas2r7.
4. The method of any one of claims 1 -3, wherein compound (A) is cholic acid or a cholic acid derivative.
5. The method of any one of claims 1-3, wherein compound (A) is a compound containing at least one tryptophan (Trp) moiety.
6. The method of any one of claims 1-3, wherein compound (A) is selected from:
Figure imgf000018_0001
Glycocholic acid (CAS 475-31-0),
Figure imgf000019_0001
Taurolithocholic Acid (CAS 516-90-5), and
Figure imgf000019_0002
Tritryptophan (CAS 59005-82-2), or combinations thereof.
7. A method for preventing or reducing damage to plants or plant propagation materials by a bird, wherein said method comprises applying to the plant propagation material a composition comprising a compound (A) selected from:
Figure imgf000019_0003
Glycocholic acid (CAS 475-31-0),
Figure imgf000020_0001
Taurolithocholic Acid (CAS 516-90-5), and
Figure imgf000020_0002
Tritryptophan (CAS 59005-82-2), or combinations thereof.
8. The method according to of any one of claims 1 -7, wherein the bird-repellent composition comprises as a further active ingredient a compound (B), wherein compound (B) is selected from acibenzolar- s-methyl, metalaxyl-M, metalaxyl, picarbutrazox, oxathiapiprolin, ethaboxam, fludioxonil, azoxystrobin, thiabendazole, difenoconazole, tebuconazole, ipconazole, mefentrifluconazole, prothioconazole, triticonazole, sedaxane, inpyrfluxam, penflufen, fluopyram, fluxapyroxad, pydiflumetofen, cyclobutrifluram, thiamethoxam, isocycloseram, isoflucypram, clothianidin, benzovindiflupyr, cymoxanil, phosphite (phosphonate), silthiofam, pyraclostrobin, isotianil, tolprocarb, quinofumelin, ipflufenoquin, metyltetraprole, florylpicoxamid, fenpicoxamid, fluoxytioconazole, fluindapyr, fluoxapiprolin, broflanilide, imidacloprid, acetamiprid, cyantraniliprole, chlorantraniliprole, tetraniliprole, fl uxa meth am ide, penthiopyrad, mandipropamid, dimpropyridaz, flupyrimin, triflumezopyrim, oxazosulfyl, dichlobentiazox, benzpirimoxan, hymexazol, pyrapropoyne, cyclaniliprole, mandestrobin, copper, lambda-cyhalothrin, phenamacril, abamectin, tefluthrin, picoxystrobin, spiropidion, oligosaccharins, Melaleuca alternifolia, fosthiazate, fenamifos, oxamyl, fluensulfone, fluazanindolizine, spirotetramat, spidoxamat, fluazinam, indazapyroxamet, thiophanate methyl, zoxamide, fluoxastrobin, pirimifos, tetrachlorantraniliprole, bifenthrin, and emamectin, or combinations thereof.
9. Use of a composition as defined in any one of claims 1-8, for repelling birds from plants and plant propagation materials.
10. The method according to any one of claims 1-8, or the use according to claim 9, wherein the plant propagation material is a seed, and preferably a maize seed, a rice seed or a cereal seed.
11 . The method according to any one of claims 1 -8 or 10, or the use according to claim 9, wherein the composition is applied at a rate corresponding to 0.01 to 2 mg of compound (A) per plant propagation material, and preferably 0.2 to 1 mg of compound (A) per plant propagation material.
12. The method according to any one of claims 1-8, 10 or 11 , orthe use according to claim 9, wherein the bird is a selected from blackbirds (Turdus merula), crows (Corvus spp.), grackles (Quiscalus spp.), pheasants (Phasianus spp.), and/or starlings (Stumus vulgaris).
13. Seed treatment formulation comprising the bird-repellent composition as defined in any one of claims 1-8.
14. A coated plant propagation material, preferably a coated seed, wherein the coating comprises a composition as defined in any one of claims 1-8.
15. Use of a compound as defined in any one of claims 1-8, which activates at least one bird taste receptor selected from Tas2r1 , Tas2r3, Tas2r4, Tas2r5, and Tas2r7, as a bird repellent.
PCT/EP2024/076576 2023-09-28 2024-09-23 Compositions and methods for repelling birds from plants and plant propagation materials Pending WO2025068079A1 (en)

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