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WO2025032165A1 - Matière à base d'huile de ricin pour libérer des composés organiques volatils biogéniques pour applications agricoles - Google Patents

Matière à base d'huile de ricin pour libérer des composés organiques volatils biogéniques pour applications agricoles Download PDF

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Publication number
WO2025032165A1
WO2025032165A1 PCT/EP2024/072425 EP2024072425W WO2025032165A1 WO 2025032165 A1 WO2025032165 A1 WO 2025032165A1 EP 2024072425 W EP2024072425 W EP 2024072425W WO 2025032165 A1 WO2025032165 A1 WO 2025032165A1
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Prior art keywords
bvoc
castor oil
group
composition according
biodegradable
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Inventor
Alessio ZULIANI
Piero Baglioni
Teresa GUARAGNONE
Federico BRILLI
Paola RIZZARELLI
Ivan BACCELLI
Marco RAPISARDA
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CONSORZIO INTERUNIVERSITARIO PER LO SVILUPPO DEI SISTEMI A GRANDE INTERFASE CSGI
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CONSORZIO INTERUNIVERSITARIO PER LO SVILUPPO DEI SISTEMI A GRANDE INTERFASE CSGI
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Publication of WO2025032165A1 publication Critical patent/WO2025032165A1/fr
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    • 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
    • A01P21/00—Plant growth regulators
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—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 solids as carriers or diluents
    • 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
    • A01N25/08—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 solids as carriers or diluents
    • A01N25/10—Macromolecular compounds
    • 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
    • A01N25/18—Vapour or smoke emitting compositions with delayed or sustained release
    • 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
    • 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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8083—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2230/00—Compositions for preparing biodegradable polymers

Definitions

  • the present invention relates to the field of controlled-release of Biogenic Volatile Organic Compounds (BVOCs); in particular it relates to a biodegradable biomass- derived composition for controlled-release of Biogenic Volatile Organic Compounds (BVOCs).
  • BVOCs Biogenic Volatile Organic Compounds
  • BVOCs Biogenic Volatile Organic Compounds
  • BVOCs belong to a diverse class of biologically generated chemicals with medium to high vapor pressure, playing crucial roles in plant defence signalling and communication. Acting as airborne signals, BVOCs enable rapid defence signalling between distant plant organs and facilitate communication between plants. Furthermore, BVOCs have the ability to prime the defence system of plants, enhancing resistance against upcoming stresses. They can also repel herbivores or attract their natural enemies, such as parasitoids or predators. Plants possess the ability to maintain a memory of previous stress events, which influences their response to future stressful situations.
  • BVOCs Factors that shape this stress memory, referred to as "priming stimuli,” play a crucial role in plant BVOCs. Due to their volatility, plant BVOCs can quickly reach different parts of the plant and contribute to priming. Priming enables a plant to exhibit an earlier, stronger, and faster response when faced with subsequent stress, leading to increased resistance and/or tolerance. BVOCs have been extensively studied for their ability to prime defences against herbivorous insects, pathogens, and environmental stresses.
  • BVOCs green leaf volatiles
  • GLVs green leaf volatiles
  • MeSA methyl salicylate
  • MeJA monoterpenes
  • SAR systemic acquired resistance
  • Methanol a volatile compound ubiquitously emitted from plant leaves during cell division and cell wall expansion, has also shown potential as a priming stimulus by enhancing resistance to pathogenic bacteria.
  • VOCs Volatile Organic Compounds
  • VOCs VOCs
  • adsorption/desorption devices CN109092013, GB2563910
  • adsorption/desorption devices CN109092013, GB2563910
  • BVOCs-emitting plants which can release a few BVOCs and subtract land and nutrients for crops
  • d) the use of gels JP2006225289) or polymers (JP2000239104 and JP1999286402), which can be revolutionary if sustainable synthesis and applications can be accomplished.
  • NZ162021 describes the use of PVC (polyvinylchloride) and PVA (Poly(vinyl alcohol)) as carriers for organic phosphorus insecticide.
  • PVC polyvinylchloride
  • PVA Poly(vinyl alcohol)
  • WO2015106342 relates to the encapsulation and controlled release of VOCs for increasing the shelf life of perishable products, by preparing fibres composed of pectin, alginate, guar gum, carrageenan, waxy com starch, a surfactant, and VOC(s).
  • the fibres are prepared by mixing the ingredients in solution followed by electrospinning. Yet, the cumbersome synthetic procedure and the utilization of surfactants limits the potentialities of the invention.
  • GR1000706 describes a system for controlled release and diffusion of biologically active volatile substances, comprised of a homogenous solution of an active component in an organic carrier, solid at room temperature and hermetically sealed in a specialised casing. Nevertheless, the use of castings limits the utilization in crops since many castings should be used and collected after utilization.
  • Subject matter of the present invention is therefore a biodegradable biomass- derived composition for control led-release of Biogenic Volatile Organic Compounds (BVOCs), said composition consisting of a continuous phase consisting of a crosslinked castor oil-based polymer and a dispersed phase comprising at least one Biogenic Volatile Organic Compound (BVOC), wherein said BVOC is biologically synthesized and effective for improving plant defence response, growth and/or productivity.
  • BVOCs Biogenic Volatile Organic Compounds
  • the biomass-derived composition of the invention demonstrated to be more efficient in controlled dispensing of BVOCs for extended periods of time.
  • the composition of the invention is biodegradable in soil and/or under light irradiation, making it disposable and capable to be assimilated into the natural environment. This stands in contrast to most current techniques and products.
  • the utilization of nonedible castor oil in the crosslinked castor oil-based polymers contributes to their low environmental impact, while their low cost and simple preparation make them advantageous.
  • Sustainable and bio-derived crosslinking agents can also be employed during production.
  • composition of the invention has the potentiality to revolutionize agricultural practices, enhance plant protection, and improve productivity while addressing concerns associated with conventional and already reported approaches.
  • the composition can be easily prepared on large scale, using environmentally friendly and biologically-derived compounds, and can be placed nearby potted plants into greenhouses, or field crops, without the need to be collected after utilization being biodegradable.
  • the present invention relates to the use of the above described composition in agriculture as well as in other applications, such as mulch, trellis netting, membranes for cooling/air conditioning systems and heat pumps, anti-hail and shading nets, and coatings.
  • the present invention relates to a controlled-release agrochemical BVOC formulation comprising or consisting of the biodegradable biomass-derived composition as above described.
  • the present invention related to an environmental friendly agricultural method of controlling the release of a single BVOC or a mixture of BVOCs effective in improving plant defence response, growth and/or productivity, said method comprising chemically or physically linking said single BVOC or a mixture of BVOCs to a biodegradable biomass-derived crosslinked castor oil-based polymer.
  • the present invention relates to a method for the agricultural controlled-release of a single BVOC or a mixture of BVOCs, said method comprising dispersing in the air surrounding crops or onto or into the soil a controlled-release agrochemical formulation as above described.
  • the present invention relates to a method for preparing the composition of the invention, said method comprising:
  • the present invention relates to an alternative method for preparing the composition of the invention, said method comprising: a', mixing a castor oil fatty acid or ester, at least one biodegradable crosslinking agent; b'. reacting the mixture of step A) at a temperature in the range from 10 to 150°C; c'. ’adding during the reaction of step b’) and at the end of it at least one BVOC having biological activity in improving plant defense response, growth and/or productivity.
  • the dispersed phase of a single BVOC or a mixture of BVOCs can be chemically and/or physically linked to the castor oil-based polymer.
  • the BVOCs can be in liquid, solid, or vapor phase.
  • BVOCs can be in the form of essential oils.
  • the single BVOC or mixture of BVOCs is selected in the group consisting of biologically derived alcohols, aldehydes, carboxylic acids, carboxylic esters and terpenes.
  • the BVOC is preferably selected in the group consisting of MeOH, benzaldehyde, acetic acid, methyl salicylate, isoprene, caryophyllene, bisabolol, selinene, germacrene, humulene, farnesene, curcumene, bergamotene, zingiberene, valencene, pinene, linalool, geraniol, eucalyptol, citronellol, cymene, cineole, thymol, menthol, hexenal, myrcene, nerol, eugenol.
  • the mass ratio of the crosslinked castor oil-based polymer to the BVOC(s) typically ranges between 20:80 to 99.9:0.1 , preferably 95:5.
  • the biomass-derived composition of the invention comprises at least one continuous phase consisting of a crosslinked castor oil-based polymer.
  • Castor oil derived from non-edible castor beans (Ricinus communis L.), is primarily composed of triglycerides of fatty acids, with ricinoleic acid (cis-12-hydroxyoctadec-9-enoic acid) normally accounting for 82-93% of its composition.
  • Castor oil-based polymers including polyurethanes, polyesters, polyethers, polyamides, and polysulfides, have been widely used in the polymer industry due to their bio-based nature (Bioresource Technol., 97 (9) 1086, 2006).
  • the advantage of using castor oil-based polymers lies in their low environmental impact, biodegradability, and compatibility with lipophilic properties of many BVOCs (i.e. terpenes) suitable for various agricultural purposes, being involved in plant defence against insects, pathogenic microbes and environmental stresses, as well as enhancing plant growth and productivity.
  • BVOCs i.e. terpenes
  • the use of bioderived crosslinking agents further enhance the sustainable features of the material and eventually boost its biodegradable characteristics.
  • the crosslinked castor oilbased polymer forms the continuous phase, acting as a net and cage for loading the dispersed phase of BVOCs.
  • the crosslinked polymer is formed by polymerizing a castor oil fatty acid or ester with a biodegradable crosslinking agent capable of forming covalent or ionic bonds with castor oil. This resulting polymer provides mechanical and thermal stability to block and stabilize the dispersed phase, even during the manufacturing process.
  • said crosslinked castor oil-based polymer is therefore obtained by polymerization of a castor oil fatty acid or ester with a crosslinking agent comprising a functional group selected from: an isocyanate group, a carboxyl group, an anhydride group, an anion group of a carboxylic acid, an amino group, an imino group, an amide group, a sulfonic acid group, an anion group of a sulfonic acid, a methanedithioic acid group, an anion group of a methanedithioic acid, or a mixture thereof.
  • Said crosslinking agent is bioderived and contains in the chemical structure polar groups such as sulfonic acid, phosphate, and sulphates that enhance the biodegradability of the material.
  • said crosslinked castor oil-based polymer is selected from the group consisting of a polyurethane, a polyester, a polyether, a polyamide, and a polysulfide.
  • the crosslinked castor oil-based polymer is a polyurethane obtained by polymerizing a castor oil fatty acid or ester with poly(hexamethylene diisocyanate), pentamethylene diisocyanate, or 3- (cyclohexylamino)-l -propanesulfonic acid- and 2-ethyl-1 -hexanol-blocked 1 ,5- pentamethylene diisocyanate, or 2-ethyl-1 -hexanol-blocked 1 ,5-pentamethylene diisocyanate, or a mixture thereof.
  • the weight ratio of the castor oil fatty acid or ester to poly(hexamethylene diisocyanate), pentamethylene diisocyanate, 3- (cyclohexylamino)-l -propanesulfonic acid- and 2-ethyl-1 -hexanol-blocked 1 ,5- pentamethylene diisocyanate, or a mixture thereof preferably ranges from 60:40 to 10:90, with 25:75 being more preferable.
  • the mixture of step A) or a’) may be shaped or applied onto a substrate, and the reaction can be carried out in sealed container, like cases, bags, bins, cans, to prevent BVOC evaporation.
  • said reaction is carried out at a temperature in the range from 50 to 90°C.
  • composition of the invention can be used as such or put in a container or applied on a substrate.
  • composition of the invention can be in solid form or in form of a highly viscous liquid which can easily dispersed in the air surrounding crops or onto or into the soil.
  • the composition according to the present invention is in form of block, powder, thin film, membrane, pellet, ball, foam, sphere, , sheet, string, paste, honeycomb, bead, mesh, fiber, corrugated sheet, net, or rotor.
  • the composition of the invention may have numerous benefits, including improving plant defence response, growth and productivity. Indeed, slow and continuous release of BVOCs can exert a protective effect against abiotic stressors by quenching the excessive production of reactive oxygen species (ROS) which can damage plant tissues.
  • ROS reactive oxygen species
  • the continuous release of BVOC by the composition of the invention can also inhibit the germination and growth of plant pathogens, repels herbivores, and attracts herbivore parasitoids.
  • exposure of plant to the BVOCs released by the composition of the invention may induce the synthesis of defence proteins and metabolites, such as phytoalexins, which impede microbial colonization.
  • the BVOCs released by the material may also acts as a priming stimulus by inducing epigenetic changes and the accumulation of transcription factors, facilitating faster expression of plant defences. Furthermore, prolonged exposure to BVOCs released by the composition of the invention may interacts with senescence mechanisms and help fights against unwanted weed species by exerting allelopathic effects.
  • the BVOC releasing rate is determined by the exposition of the composition of the invention, loaded with different amount of BVOCs and prepared using different castor oil to crosslinker ratios, to a controlled atmosphere and monitored by weight losses.
  • the releasing rate is reported as an average of the releasing rate measured every day for at least 10 days.
  • the BVOCs releasing rate is reported normalized to the mass of the biomass-derived composition.
  • the biomass-derived cross-linked castor oil based polymer without BVOCs is used as reference.
  • the BVOCs concentration is monitored by international standards (such as OSHA PV2199 for acetic acid) also using chromatography analysis (for example, with a GC-MS from PerkinElmer, USA or a PTR--MS analyzer from lonicon, Austria). Degradation in soil burial test
  • Soil burial tests are carried out at 30.0 ⁇ 0.1 °C, under moisture-controlled conditions.
  • Triplicate specimens of film samples are placed in darkened vessels containing a multi-layer substrate.
  • Filter paper is used as a positive control.
  • Sample portions of 2 cm x 2 cm are cut.
  • the bottom and top layers are filled with 60 g of perlite moistened with 120 mL of distilled water.
  • the protective effect against pathogens is measured by running experiments with the fungus Botrytis cinerea, a pathogen able to infect hundreds of plant species on their aboveground organs (leaves and fruits), in controlled and sealed atmosphere.
  • the experiments are performed with the fungus grown in vitro on appropriate growth medium (potato dextrose agar, PDA), and by using tomato leaves where fungal spores are inoculated.
  • Fig. 1 Controlled release of VOC (/.e., isoprene) by the biomass-derived material of the invention as by the two formulations of different texture, soft (material 5A) and dense (material 5B).
  • the release of VOC (i.e., isoprene) is expressed on a volume (Fig. lA) or on mass basis (Fig.1 B) of the material.
  • EXAMPLE 1 controlling the BVOC releasing rate under dynamic conditions
  • Methyl salicylate is known as to elicit plant defence and repel herbivores (e.g.in Brassica rapa subsp. chinensis against peach potato aphids, Myzus persicae).
  • herbivores e.g.in Brassica rapa subsp. chinensis against peach potato aphids, Myzus persicae.
  • the mixtures were then poured into aluminium bags, sealed, and pressed in a mould to obtain foils of 10x10x0.5 cm and cured at 85°C for 24 hours. Samples were thus cut in pieces of 2x2x0.5 cm and placed in a 20 L box under an air flux of 0.1 ml min’ 1 .
  • the BVOC releasing rates were obtained according to the method above detailed and measured on average on fifty days. The results are reported in Table 1.
  • Example 1 was repeated without adding any BVOC, to determine the weight losses and adjust the average BVOC releasing rate accordingly.
  • Example 2 was repeated without adding acetic acid.
  • a biomass-derived composition according to the invention was prepared as follow: 78 g of castor oil (Pharma Quality, Giomavaro Sri, Italy), 22 g of 3- (cyclohexylamino)-l -propanesulfonic acid- and 2-ethyl-1 -hexanol-blocked 1 ,5- pentamethylene diisocyanate (Covestro SA, Germany) and 1 g of p-cymene were mixed with a magnetic stirrer for 5 minutes at 20°C.
  • p-cymene is a BVOC known to have an antimicrobial activity.
  • Material 5A was prepared as follows: 78 g of castor oil (Pharma Quality, Giomavaro Sri, Italy) and 22 g of 2-ethyl-1 -hexanol-blocked 1 ,5-pentamethylene-diisocyanate (Covestro SA, Germany) were mixed in a round flask with a magnetic stirrer for 15 minutes at 20°C; 100 pl of isoprene were then added. Isoprene is a small lipophilic VOC produced by several plant species and known to protect them from a wide range of abiotic and biotic stresses. The mixture was then poured into aluminium bags, sealed, and pressed in a mould to obtain foils of 10x10x0.5 cm and cured at 85°C for 24 hours.
  • Material 5B was prepared by following the same procedure as material 5A, but using 56 g of castor oil (Pharma Quality, Giomavaro Sri, Italy) and 44 g of 2-ethyl-1 - hexanol-blocked 1 ,5-pentamethylene-diisocyanate (Covestro SA, Germany), into which 100 pl of isoprene was added.
  • Material 5A resulted softer and less rigid than material 5B, due to a lower formation of polyurethanes. Accordingly, the material 5A is referred to as “soft” in the figure 1 , whereas the material 5B is referred to as “dense”.
  • the controlled release of the VOC was then normalized by either the volume (Fig.1 A) or density (Fig. 1 B) of the two different formulations of the biomass-derived material (5A and 5B).
  • both the biomass-derived materials showed a controlled and long-lasting release of the VOC (/.e., isoprene), reaching a constant rate (/.e., a plateau) within a few hours.
  • VOC /.e., isoprene
  • the constant release rate of the VOC released achieved after a few hours
  • the amount of VOC /'.e. , isoprene
  • the different rate of release of VOC by the two materials can be ascribed to the peculiar physicochemical interactions of isoprene with castor oil, rather than the different polymeric mesh which characterizes the materials. Indeed, the less dense the material, the more the amount of castor oil that was used for the preparation, which interacted through higher intramolecular bonds (/.e., Van der Walls, etc.) with isoprene, thus entrapping this relatively high-vapour-pressure (733.3 hPa at 25°C) VOC and slowing down the release rate. Hence, depending on the different application, it is possible to modulate the release rate of the VOC embedded into the biomass-derived material of the present invention by varying the composition of the material components herein described.

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

La présente invention concerne une composition dérivée de biomasse biodégradable permettant la libération contrôlée de composés organiques volatils biogéniques (COVb), ladite composition étant formée d'une phase continue constituée d'un polymère à base d'huile de ricin réticulé et d'une phase dispersée comprenant au moins un composé organique volatil biogénique (COVb), ledit COVb étant synthétisé biologiquement et efficace pour améliorer la réponse défensive des plantes, leur croissance et/ou leur productivité.
PCT/EP2024/072425 2023-08-10 2024-08-08 Matière à base d'huile de ricin pour libérer des composés organiques volatils biogéniques pour applications agricoles Pending WO2025032165A1 (fr)

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IT102023000017154A IT202300017154A1 (it) 2023-08-10 2023-08-10 Materiale a base di olio di ricino per il rilascio di composti organici volatili biogenici per applicazioni agricole
IT102023000017154 2023-08-10

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