WO2020221919A1 - Composition d'amélioration de récolte - Google Patents

Composition d'amélioration de récolte Download PDF

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Publication number
WO2020221919A1
WO2020221919A1 PCT/EP2020/062187 EP2020062187W WO2020221919A1 WO 2020221919 A1 WO2020221919 A1 WO 2020221919A1 EP 2020062187 W EP2020062187 W EP 2020062187W WO 2020221919 A1 WO2020221919 A1 WO 2020221919A1
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WO
WIPO (PCT)
Prior art keywords
lactam
composition
eutecting
agent
eutectic
Prior art date
Application number
PCT/EP2020/062187
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English (en)
Inventor
Bijpost ERIK ALEXANDER
Alexander Maslow
Wasil Maslow
Original Assignee
Novochem Green Additives 2 B.V.
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Publication of WO2020221919A1 publication Critical patent/WO2020221919A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N3/00—Preservation of plants or parts thereof, e.g. inhibiting evaporation, improvement of the appearance of leaves or protection against physical influences such as UV radiation using chemical compositions; Grafting wax
    • 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
    • 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
    • A01N3/00—Preservation of plants or parts thereof, e.g. inhibiting evaporation, improvement of the appearance of leaves or protection against physical influences such as UV radiation using chemical compositions; Grafting wax
    • A01N3/02—Keeping cut flowers fresh chemically
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, 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
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members

Definitions

  • the present invention relates to crop enhancement compositions.
  • the objective of the present invention is to provide novel crop enhancement compositions.
  • a further objective is to provide novel plant and/or flower preservation compositions.
  • a further objective is to provide novel herbicide compositions. All compositions of the invention make use of a single inventive concept, viz. the compositions comprise a lactam and/or a eutectic composition comprising a lactam and a eutecting agent.
  • the lactam and/or eutectic composition are capable of keeping the soil surrounding the plant and/or plant roots moist, even under drought conditions. This is especially advantageous in areas where water is scarce and/or where irrigation with water needs to be rationed. It could also lead to a better water management and water usage. Growth of the plants under low temperature conditions (i.e. below 7°C) has also been observed.
  • the composition of the invention generally has a low vapour pressure due to the high boiling point of the lactam.
  • the eutectic composition of the invention can be prepared using components, i.e. the lactam and the eutecting agent, that are both solid at room temperature.
  • compositions may be liquid at room temperature, like for example a eutectic composition of e-caprolactam and salicylic acid, g- butyrolactam and salicylic acid, and g-butyrolactam and maleic anhydride.
  • compositions comprised of a component that is solid at room temperature and a component that is liquid at room temperature may form a liquid eutectic composition, like for example g-butyrolactam and PEG 200 (polyethylene glycol), g-butyrolactam and citraconic anhydride, and e-caprolactam and citraconic anhydride.
  • compositions comprised of components that are liquid at room temperature are contemplated.
  • the agrochemical composition, and in particular the eutectic composition of the invention has a melting point below 0°C.
  • the inventive compositions are liquid at room temperature, rendering an easier processing and use of the eutectic composition of the invention.
  • the melting point of the eutectic composition of the invention is at most -5°C, more preferably at most -10°C, even more preferably at most -15°C, and most preferably at most -20°C, and preferably at least -100°C, more preferably at least -90°C, even more preferably at least -80°C, and most preferably at least -75°C.
  • the agrochemical composition of the invention generally has a (dynamic) viscosity at 20°C of at most 10,000 cP, preferably at most 1 ,000 cP, more preferably at most 100 cP and most preferably at most 10 cP, and preferably at least 0.1 cP, more preferably at least 0.2 cP and most preferably at least 0.5 cP.
  • a viscosity can be measured using techniques conventionally used in the art, e.g. Brookfield.
  • the crop enhancement composition of the invention comprises the eutectic composition comprising a lactam and a eutecting agent.
  • the composition of the invention comprises the eutectic composition in an amount of at most 90 % by weight (wt%), based on the total weight of the agrochemical composition.
  • the eutectic composition is present in an amount of at most 85 wt%, more preferably at most 80 wt%, even more preferably at most 75 wt%, even more preferably at most 70 wt%, even more preferably at most 60 wt% and even most preferably at most 50 wt%, and preferably at least 10 wt%, more preferably at least 15 wt%, even more preferably at least 20 wt%, even more preferably at least 25 wt%, even more preferably at least 30 wt% and most preferably at least 35 wt%, based on the total weight of the agrochemical composition.
  • the lactam of the invention is well known in the art and refers to a cyclic amide. Typically and preferably, the lactam is not substituted on the nitrogen in the ring. Most preferably, the lactam is not substituted. Examples of lactams include b-lactam, g-lactam, d-lactam and e-lactam. The lactam may be substituted, e.g. with C1 -C4 alkyl or vinyl, or unsubstituted. Unsubstituted lactams are preferred.
  • lactams are used in the eutectic composition of the invention.
  • the lactam may also be an oligomer of the lactam, preferably the oligomer is a cyclic oligomer.
  • the oligomer can be a dimer, trimer, tetramer, pentamer of hexamer of lactam. Examples of the oligomers of lactam can be found in Abe et al. (Abe, Y. et al (2016) Isolation and Quantification of Polyamide Cyclic Oligomers in Kitchen Utensils and Their Migration into various Food Stimulants, PLoS ONE 1 1 (7): e0159547, doi:10.1371/journal. pone.0159547).
  • the oligomer is a dimer of lactam, even more preferably the dimer is a dimer of caprolactam, preferably 1 ,8-diaxacyclodecane-2,9-dione.
  • the lactam of the invention is a combination of g-butyrolactam and e-caprolactam.
  • the invention encompasses a eutectic composition comprising g- butyrolactam and e-caprolactam, as well as a eutectic composition comprising g-butyrolactam and e-caprolactam and a eutecting agent.
  • the eutectic composition comprises g-butyrolactam and e-caprolactam. In either the eutectic composition or the lactam combination, the molar ratio between g-butyrolactam and e-caprolactam is at least 0.01.
  • the ratio is at least 0.05, more preferably at least 0.1 , even more preferably at least 0.2, even more preferably at least 0.5, and most preferably at least 1 , and preferably at most 100, more preferably at most 75, even more preferably at most 50, even more preferably at most 40, even more preferably at most 20, even more preferably at most 10 and most preferably at most 5.
  • the eutectic composition of the invention comprises the lactam in an amount of at most 90 % by weight (wt%), based on the total weight of the eutectic composition.
  • the lactam is present in an amount of at most 85 wt%, more preferably at most 80 wt%, even more preferably at most 70 wt%, even more preferably at most 60 wt%, even more preferably at most 50 wt% and even most preferably at most 40 wt%, and preferably at least 1 wt%, more preferably at least 2 wt%, even more preferably at least 5 wt%, even more preferably at least 10 wt%, even more preferably at least 15 wt% and most preferably at least 20 wt%, based on the total weight of the eutectic composition.
  • the eutecting agent in the eutectic composition of the invention can be any eutecting agent capable of forming a eutectic mixture with the lactams.
  • the eutecting agent has an ionic part.
  • the ionic part can be cationic, anionic or amphiphilic, preferably the ionic part is amphiphilic.
  • the eutecting agent can be a hydrogen-bond donor, an electron pair donor, hydrogen-bond acceptor, an electron pair acceptor or a metal salt.
  • the eutecting agent is a hydrogen-bond donor or acceptor comprising a functional group selected from, but not limited to, acids, anhydrides, amines, amides, imides, alcohols, quaternary ammonium salts.
  • the eutecting agent is selected from the group consisting of cyclic acids, aliphatic acids, cyclic acid anhydrides, aliphatic acid anhydrides, amines, amides, imides and alcohols.
  • the eutecting agent is selected from the group consisting of cyclic acids and cyclic anhydrides.
  • cyclic acid refers to a ring-containing molecule comprising an acid group; the ring can be a phenyl group or a cycloalkyl group, for example and the acid group can be a carboxylic acid or a sulphonic acid group, for instance.
  • the eutecting agent comprises at least 2 functional groups.
  • the functional groups may be the same or different.
  • the advantage of a eutecting agent having at least two functional groups is that the resulting eutecting composition when combined with the lactam of the invention is more stable and less dependent on pH, temperature and/or concentration.
  • the eutecting agent comprises at least 2 functional groups in which at least two functional groups are separated by at most 3 atoms, preferably at most 2 atoms.
  • the polyfunctional compound comprises at least one of the substituents selected from the group consisting of carboxylic acid and ether.
  • the other group(s) may be any known functional group.
  • the eutecting agent comprises at least 3 carbon atoms, and preferably at least 4 carbon atoms.
  • the eutecting agent can be a monomer, an oligomer or a polymer.
  • the eutecting agent is an oligomer or polymer having a plurality of functional groups.
  • the molar ratio should be calculated based on the number of monomers present in the oligomer or polymer. In other words, a polymer comprising 500 monomer units should be contacted with 500 lactam molecules to reach a molar ratio between polymer and lactam of 1 or 1 :1.
  • Suitable acids include aliphatic monoacids such as formic acid, acetic acid, lactic acid and butyric acid; aliphatic polyacids such as oxalic acid, citric acid, citraconic acid and maleic acid; and cyclic acids such as salicylic acid, 2-phenol phosphinic acid, 2-phenol phosphonic acid and 2-phenol sulphonic acid.
  • the acid is a cyclic acid, more preferably the acid is salicylic acid.
  • the eutectic agent is an acid having a pKa (i.e.
  • the acid dissociation constant) of at most 6 preferably a pKa of at most 5, and more preferably a pKa of at most 4, even more preferably a pKa of at most 3.5 and most preferably a pKa value of at most 3, and preferably a pKa of at least 0, more preferably a pKa of at least 0.5 and most preferably a pKa of at least 1.
  • Suitable acid anhydrides include aliphatic acid anhydrides such as formic anhydride, acetic anhydride, propanoic anhydride, butyric anhydride, crotonic anhydride and benzoic anhydride; and cyclic acid anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, phthalic anhydride, trimellitic anhydride, hexahydrophthalic anhydride, methyl hexahydrophthalic anhydride, tetrahydrophthalic anhydride, methyl tetrahydrophthalic anhydride, tetrachlorophthalic anhydride, pyromellitic dianhydride, himic anhydride, succinic anhydride, dodecenylsuccinic anhydride, chlorendic anhydride and tetrabromophthalic anhydride.
  • aliphatic acid anhydrides such as formic anhydride, acetic anhydride, prop
  • the acid anhydride is a cyclic acid anhydride. More preferably, the cyclic acid anhydride is selected from the group consisting of maleic anhydride, citraconic anhydride, itaconic anhydride and phthalic anhydride, even more preferably the cyclic acid anhydride is maleic anhydride or citraconic anhydride, and most preferably, the acid anhydride is maleic anhydride.
  • the advantage of maleic anhydride and citraconic anhydride is their potential to react with water, oxygen and radicals. These anhydrides are further advantageous in ternary or quaternary eutectic compositions to reduce the viscosity of the resulting eutectic composition.
  • a solute when dissolved in the eutectic composition of the invention its viscosity may increase at higher solute concentrations - which tend to be higher than the solubility in conventional solvents - the cyclic anhydride, and in particular maleic anhydride and/or citraconic anhydride, significantly reduces the viscosity of the eutectic composition.
  • Suitable ethers include monomeric ethers such as methyl ethyl ether, methyl phenyl ether, diethylene glycol, triethylene glycol, dibutyl ether, and dihexyl ether; and polyethers such as paraformaldehyde, polyethylene glycol (PEG), polypropylene glycol (PPG), polytetramethylene glycol (PTMG), polytetramethylene ether glycol (PTMEG),
  • monomeric ethers such as methyl ethyl ether, methyl phenyl ether, diethylene glycol, triethylene glycol, dibutyl ether, and dihexyl ether
  • polyethers such as paraformaldehyde, polyethylene glycol (PEG), polypropylene glycol (PPG), polytetramethylene glycol (PTMG), polytetramethylene ether glycol (PTMEG),
  • PPOX polypropylene oxide
  • EO/PO block copolymers polyethyleneglycol-polypropyleneglycol
  • Aromatic ethers such as phenolic and benzylic ethers, are also suitable.
  • polysaccharides examples include celluloses such as cellulose, methyl cellulose (MC), ethyl cellulose (EC), hydroxyethyl cellulose (HEC), ethyl hydroxyethyl cellulose (EHEC), methyl ethyl hydroxyethyl cellulose (MEHEC), carboxymethyl cellulose (CMC), hydroxypropyl methyl cellulose (HPMC); and starches such as starch, oxidized starch, hydroxyethyl starch, hydroxypropyl starch and carboxymethyl starch; chitin and arabinoxylans.
  • the polysaccharide can have any degree of polymerization (DP) and degree of substitution (DS) known in the art.
  • Examples of functionalized polymers include polyvinyl alcohol (PVA), polyvinyl acetate, polyvinylbutyral (PVB), polyvinylamine, polyvinylamides, polyurethanes, polyamides, polyimides, polycarbonates, polyesters, poly lactic acid (PLA), poly(lactic-co-glycolic acid) (PLGA), and polyvinyl pyrrolidone (PVP).
  • PVA polyvinyl alcohol
  • PVB polyvinylbutyral
  • PVAm polyvinylamine
  • polyvinylamides polyurethanes
  • polyamides polyamides
  • polyimides polyimides
  • polycarbonates polyesters
  • PVA poly lactic acid
  • PLA poly(lactic-co-glycolic acid)
  • PVP polyvinyl pyrrolidone
  • Suitable amines include aliphatic polyamines include EDA homologues such as linear, branched and cyclic EDA homologues including tetraethylene pentamine (TEPA), triethylene tetramine (TETA), diethylene triamine (DETA), hexaethylene pentamine (HEPA) and N-aminoethyl piperazine (NAEP); propylene homologues such as dipropylene triamine (DPTA; methylene homologues such as hexamethylene pentamine (HMPA); polyether monoamines such as Jeffamine® M-600 amine, Jeffamine® M-1000 amine, Jeffamine® M-2005 amine and Jeffamine® M-2070 amine; polyether diamines such as Jeffamine® D-230 amine, Jeffamine® D-2300 amine, Jeffamine® D-400 amine, Jeffamine® D-4000 amine, Jeffamine® ED-600 amine, Jeffamine® ED-900 amine, Jeffamine® ED-2003 amine, Jeffamine® E
  • dipropylene triamines such as dodecyl dipropylene triamine, oleyl dipropylene triamine, octyl dipropylene triamine, stearyl dipropylene triamine and tallow dipropylene triamine and other polyamines such as N-tallowalkyl dipropylene tetramine, N-tallowalkyl tripropylene triamine, N- (3-aminopropyl)-N-cocoalkyl propylene diamine, N-(3-aminopropyl)-N-tallowalkyl propylene diamine, N-(3-aminopropyl)-N-cocoalkyl trimethylenediamine, N-(3-aminopropyl)-N-tallowalkyl trimethylenediamine and dendrimers containing propylene diamines; bisalkylated amines such as di(dodecyl) amine, di(oleyl) amine, di(arachi
  • di(cocoalkyloxy) amine di(cocoalkyloxy) amine
  • alkoxylated amines such as isopropyloxypropyl amine
  • Suitable amides include aliphatic unsubstituted amides such as urea, formamide, acetamide, propanamide, butanamide, pentanamide, hexanamide and heptanamide; substituted aliphatic amides such as N-methylpropanamide, N-ethylpropanamide, N-methylbutanamide, N- ethylbutanamide, N-acetyl-3-oxopentanamide, N-acetyl butanamide, N-acetyl propanamide, N- Acetyl-2-amino-5-(diaminomethylideneamino) pentanamide, N-acetyl benzamide, N- methylpentanamide, N-ethylpentanamide; aromatic amides such as benzamide, ethenzamide and salicylamide.
  • aliphatic unsubstituted amides such as urea, formamide, acetamide, propan
  • suitable imides include aliphatic imides such as trifluoromethylsulfonyl imide, pentafluoroethylsulfonyl imide, methylsulfonyl imide and ethylsulfonyl imide; cyclic imides such as succinimide, maleimide, citraconimide, glutarimide, phthalimide, tetrahydrophthalimide, hexahydrophthalimide, pyromellitic diimide, 1 ,8-naphthalimide, cyclohexane-1 ,2-dicarboximide and 1 ,3-bis(citraconimidomethyl) benzene (Perkalink® 900).
  • the imide is 1 ,3- bis(citraconimidomethyl) benzene.
  • suitable alcohols include aliphatic polyols such as 1 ,2-ethanediol, 1 ,3-propanediol, 1 ,4-butanediol, glycerol, ethylene glycol, propylene glycol, mannitol and trimethylol propane (TMP); and cyclic alcohols such as ascorbic acid, glucuronic acid, catechol and salicylic acid; monosaccharides such as glucose, altrose, fructose, mannose, iodose, talose, allose, gulose, galactose, ribose, arabinose, xylose, lyxose and glucosamine; and disaccharides such as sucrose, lactose, lactulose, trehalose, cellobiose and chitobiose.
  • aliphatic polyols such as 1 ,2-ethanediol, 1 ,3-propanedi
  • the eutectic composition of the invention comprises the lactam in an amount of at least 10 % by weight (wt%), based on the total weight of the eutectic composition.
  • the lactam is present in an amount of at least 15 wt%, more preferably at least 80 wt%, even more preferably at least 30 wt%, even more preferably at least 40 wt%, even more preferably at least 50 wt% and even most preferably at least 60 wt%, and preferably at most 99 wt%, more preferably at most 98 wt%, even more preferably at most 95 wt%, even more preferably at most 90 wt%, even more preferably at most 85 wt% and most preferably at most 80 wt%, based on the total weight of the eutectic composition.
  • the molar ratio between lactam and the eutecting agent is at least 0.01.
  • the ratio is at least 0.05, more preferably at least 0.1 , even more preferably at least 0.2, even more preferably at least 0.5, and most preferably at least 1 , and preferably at most 100, more preferably at most 75, even more preferably at most 50, even more preferably at most 40, even more preferably at most 20, even more preferably at most 10 and most preferably at most 5.
  • the molar ratio between lactam and the eutecting agent is at least 0.01.
  • the ratio is at least 0.05, more preferably at least 0.1 , even more preferably at least 0.2, even more preferably at least 0.5, and most preferably at least 1 , and preferably at most 100, more preferably at most 75, even more preferably at most 50, even more preferably at most 40, even more preferably at most 20, even more preferably at most 10 and most preferably at most 5.
  • the eutecting agent is water.
  • the eutectic composition comprises a lactam and water. The lactam may be the same as indicated above.
  • lactam and water can form a eutectic composition, which results in a lowering of the melting temperature of the resulting eutectic composition compared to the individual melting points of the lactam and water.
  • Eutectic compositions of lactam and water were observed to be liquid at temperatures below 0°C, even as low as -10°C. These eutectic compositions are able to dissolve both hydrophilic and hydrophobic components.
  • the advantages mentioned for eutectic compositions comprising lactam and a eutecting agent generally also apply to the eutectic compositions comprising lactam and water.
  • the molar ratio between lactam and water is at least 0.01.
  • the ratio is at least 0.05, more preferably at least 0.1 , even more preferably at least 0.2, even more preferably at least 0.5, and most preferably at least 1 , and preferably at most 100, more preferably at most 75, even more preferably at most 50, even more preferably at most 40, even more preferably at most 20, even more preferably at most 10 and most preferably at most 5.
  • the eutectic composition of the invention comprises the lactam in an amount of at most 90 % by weight (wt%), based on the total weight of the eutectic composition.
  • the lactam is present in an amount of at most 85 wt%, more preferably at most 80 wt%, even more preferably at most 75 wt%, even more preferably at most 70 wt%, even more preferably at most 60 wt% and even most preferably at most 50 wt%, and preferably at least 1 wt%, more preferably at least 2 wt%, even more preferably at least 5 wt%, even more preferably at least 10 wt%, even more preferably at least 15 wt%, even more preferably at least 20 wt% and most preferably at least 25 wt%, based on the total weight of the eutectic composition.
  • the eutectic composition of the invention comprises water in an amount of at least 15 wt% and at most 75 wt%.
  • These eutectic compositions generally have a lower melting point than eutectic compositions comprising water amounts outside of the indicated range.
  • the lactam such as e-caprolactam, may at least partially solidify at temperatures below 0°C.
  • amounts of water above 75 wt% may cause freezing of the water in the composition at temperatures below 0°C.
  • the eutectic composition of the invention comprises water in an amount of at least 10 % by weight (wt%), based on the total weight of the eutectic composition.
  • water is present in an amount of at least 15 wt%, more preferably at least 20 wt%, even more preferably at least 25 wt%, even more preferably at least 30 wt%, even more preferably at least 40 wt% and even most preferably at least 50 wt%, and preferably at most 99 wt%, more preferably at most 98 wt%, even more preferably at most 95 wt%, even more preferably at most 90 wt%, even more preferably at most 85 wt%, even more preferably at most 80 wt% and most preferably at most 75 wt%, based on the total weight of the eutectic composition.
  • the eutectic composition of the invention further comprises a second eutecting agent.
  • the second eutecting agent may be the same as the eutecting agent indicated above.
  • the eutectic composition further comprises a hydroxide salt.
  • hydroxide salts include alkali metal hydroxides such as potassium hydroxide and sodium hydroxide. Of these hydroxide salts potassium hydroxide and sodium hydroxide are preferred.
  • the addition of such hydroxide salts generally causes the lactam to be converted into lactamate. Such lactamates generally have all the advantages the lactam has in the eutectic compositions of the invention.
  • the eutectic composition of the invention comprises the hydroxide salt in an amount of at most 90 % by weight (wt%), based on the total weight of the eutectic composition.
  • the hydroxide salt is present in an amount of at most 85 wt%, more preferably at most 80 wt%, even more preferably at most 75 wt%, even more preferably at most 70 wt%, even more preferably at most 60 wt% and even most preferably at most 50 wt%, and preferably at least 1 wt%, more preferably at least 2 wt%, even more preferably at least 5 wt%, even more preferably at least 10 wt%, even more preferably at least 15 wt%, even more preferably at least 20 wt% and most preferably at least 25 wt%, based on the total weight of the eutectic composition.
  • the molar ratio between lactam and hydroxide salt is at least 0.01.
  • the ratio is at least 0.05, more preferably at least 0.1 , even more preferably at least 0.2, even more preferably at least 0.5, and most preferably at least 1 , and preferably at most 100, more preferably at most 75, even more preferably at most 50, even more preferably at most 40, even more preferably at most 20, even more preferably at most 10 and most preferably at most 5.
  • the molar ratio between lactam and hydroxide salt should be at least 1. In this way, the hydroxide is completely consumed by the lactam and no or a small amount of residual hydroxide remains in the eutectic composition.
  • the crop enhancement composition further comprises water.
  • the crop enhancement composition of the invention comprises water in an amount of at most 99.9 % by weight (wt%), based on the total weight of the crop enhancement composition.
  • the water is present in an amount of at most 99.5 wt%, more preferably at most 99 wt%, and most preferably at most 98 wt%, and preferably at least 1 wt%, more preferably at least 5 wt%, even more preferably at least 10 wt%, even more preferably at least 50 wt%, even more preferably at least 80 wt% and most preferably at least 90 wt%, based on the total weight of the crop enhancement composition.
  • the crop enhancement composition of the invention comprises water in an amount of at most 99.9 % by weight (wt%), based on the total weight of the crop enhancement composition.
  • the water is present in an amount of at most 99.5 wt%, more preferably at most 99 wt%, and most preferably at most 98 w
  • the enhancement composition of the invention generally is compatible with water, and can be readily diluted with water.
  • the eutectic composition may comprise substances that have a low water solubility, and allow these substances to be stably present in water at concentrations above their maximum water solubility. It is envisaged that the eutectic composition may lose its eutectic nature upon addition of substantial amounts of water, e.g. above 50 wt%.
  • the crop enhancement composition comprises at least 95 wt%, preferably at least 98 wt%, of water, the drought tolerance or resistance and/or cold tolerance of the plants will increase. It is also envisaged that the crop enhancement composition is diluted with water prior to its application.
  • the amount of water in the diluted crop enhancement composition is at least 95 wt%, preferably at least 98 wt%, and at most 99.9 wt%, preferably at most 99.5 wt%, based on the total weight of the crop enhancement composition.
  • the crop enhancement composition further comprises an active ingredient.
  • the active ingredient in the composition of the invention can be any active ingredient known in the art.
  • the active ingredient may be an insecticide, a fungicide, a nematicide, a herbicide and/or a herbicide safener. Combinations of two or more active ingredients are also present.
  • the active ingredient has a solubility in water at 20°C of at most 10,000 mg/I, preferably of at most 5,000 mg/I, more preferably of at most 2,000 mg/I and most preferably of at most 1 ,000 mg/I, and preferably of at least 0.0001 mg/I, more preferably of at least 0.01 mg/I, even more preferably of at least 0.1 and most preferably of at least 1 mg/I.
  • suitable insecticides include neonicotinoids such as imidacloprid, clotianidin, thiamethoxam, acetamiprid, dinotefuran, nitempyram and thiacloprid; carbamates such as thiodicarb, aldicarb, carbofuran, furadan, fenoxycarb, carbaryl, sevin ethienocarb and fenobucarb; diamides such as chlorantraniliprole, cyantraniliprole and flubendiamide; spinosyns such as spinosad and spinetoram; pyrethroids such as lambda-cyhalothrin, gamma-cyhalothrin and tefluthrin; and phenylpyrazole such as fipronil.
  • neonicotinoids such as imidacloprid, clotianidin, thiamethoxam, acetamiprid, di
  • fungicides examples include azoxystrobin, trifloxystrobin, fluoxastrobin,
  • cyproconazole difenoconazole, prothioconazole, tebuconazole, triticonazole, fludioxonil, thiabendazole, ipconazole, cyprodinil, myclobutanil, metalaxyl, metalaxyl-M (mefenoxam), amisulbrom, ametoctradin, boscalid, fluopyram, ilsotianil, penflufen, penthiopyrad, proquianazid, sedaxane and penflufen.
  • herbicides examples include 2,3,6-TBA, 2,4-D, 2,4-D-2-ethylhexyl, 2,4-D-butoyl, 2,4- D-isopropyl, acetochlor, aclonifen, alachlor, allidochlo, ametryn, amidosulfuron, aminopyralid, anilofos, atraton, atrazine, aziprotryne, barban, beflubutamid, benazolin-ethyl, benfluralin, benfuresate, benzoifenap, bifenox, bromacil, bromobutide, bromuron, butachlor, butamnifos, butenachlor, butralin, buturon, butylate, carfentrazone-ethyl, chlomethoxyfen, chlorbromuron, chlorphthalim, chlorpropham, chlorthal-dimethyl, chlorthiamid, cinmethylin, cleth
  • tembotrione tepraloxydim, terbacil, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazafluron, thiazopyr, thiencarbazone, thiobencarb, thifensulfuron, tiocarbazil,mm tralkoxydim, triasulfuron, tri-allate, triclopyr, tridiphane, trifluralin, tritosulfuron, vernolate, and ZA9244.
  • herbicide safeners include AD67, BAS 145138, benoxacor, cloquintocet- mexyl, cyprosulfamide, dichlormid, fenchlorazole-ethyl, flurazole, fluxofenim, furilazole, MG 191 , oxabetrinil, naphthalic anhydride, mefenpyr-methyl, mefenpyr-diethyl, isooxadifen, oxabenitril, fenclorim, mefenpyr, cyometrinil and N-(2-methoxybenzoyl)-4-(methylamino carbonyl) amino) benzene sulfonamide.
  • the crop enhancement composition of the invention comprises the active ingredient in an amount of at most 85 % by weight (wt%), based on the total weight of the crop enhancement composition.
  • the active ingredient is present in an amount of at most 70 wt%, more preferably at most 60 wt%, even more preferably at most 50 wt%, even more preferably at most 40 wt% and most preferably at most 30 wt%, and preferably at least 1 wt%, more preferably at least 2 wt%, even more preferably at least 5 wt% and most preferably at least 10 wt%, based on the total weight of the crop enhancement composition.
  • the remaining part of the agrochemical composition may be comprised of other components commonly or not commonly used in agrochemical compositions.
  • the lactam, the eutecting agent, water and the active ingredient the other components add up to 100 wt% of the total weight of the agrochemical composition.
  • the crop enhancement composition further comprises an additive.
  • the additive can be any additive known in the art and suitably used in crop enhancement compositions. Examples of such additives include UV protectants, pigments, dyes, extenders such as flour, dispersing agents, preservatives, seed safeners, seed conditioners,
  • micronutrients organic fertilizers, inorganic fertilizers, fungus (e.g mycorrhiza), biocontrol agents, surfactants, sequestering agents, plasticizers, colorants, brighteners, emulsifiers, flow agents such as calcium stearate, talc and vermiculite, coalescing agents, defoaming agents, humectants, thickeners, waxes, bactericides, odor-modifying agents, fillers such as cellulose, glass fibers, clay, kaolin, talc, pulverized tree bark, calcium carbonate and wood meal; and excipients such as mineral substances like pumice, attapulgite, bentonite, kaoline zeolite, diatomite and other clays, and organic substances like peat moss and wood powder.
  • biocontrol agents such as calcium stearate, talc and vermiculite, coalescing agents, defoaming agents, humectants, thickeners, waxe
  • the crop enhancement composition of the invention comprises the additive in an amount of at most 30 % by weight (wt%), based on the total weight of the crop enhancement composition.
  • the additive is present in an amount of at most 25 wt%, more preferably at most 20 wt%, even more preferably at most 15 wt%, even more preferably at most 10 wt% and most preferably at most 5 wt%, and preferably at least 0.1 wt%, more preferably at least 0.2 wt%, even more preferably at least 0.5 wt% and most preferably at least 1 wt%, based on the total weight of the crop enhancement composition.
  • the invention further pertains to the use of a lactam and/or a eutectic composition comprising a lactam and a eutecting agent in a crop enhancement composition.
  • the invention further pertains to the use of a lactam and/or a eutectic composition comprising a lactam and a eutecting agent as a crop enhancement agent.
  • the composition can be applied as a soil treatment, a foliar treatment or a seed treatment.
  • the crop enhancement composition of the invention can be in any form known in the art. Examples of such forms include solutions, emulsions, granules, powders and pellets.
  • plant propagation material is understood to denote all the generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative plant materials such as cutting and tubers (e.g. potatoes), roots, fruits, bulbs, rhizomes, stem parts of gramineous plants (e.g. sugar cane) and other parts of a plant. Also germinated plants and young plants are included.
  • vegetative plant materials such as cutting and tubers (e.g. potatoes), roots, fruits, bulbs, rhizomes, stem parts of gramineous plants (e.g. sugar cane) and other parts of a plant. Also germinated plants and young plants are included.
  • the invention further pertains to a flower and/or plant preservation composition comprising a lactam and/or a eutectic composition comprising a lactam and a eutecting agent, and optionally water.
  • the invention further pertains to the use of a lactam and/or a eutectic composition comprising a lactam and a eutecting agent as a flower and/or plant preservative.
  • the inventors have found that applying the preservation composition of the invention to a leaf or a flower of a plant that the water content remains higher when compared to an untreated leaf or flower. When the leaf and/or flower is deprived of water, e.g.
  • the preservation composition of the invention enables (young) flowers and/or plants to survive and maintain their color and shape during transport, and consequently a higher percentage of plants and/or flowers will survive and reach the customer.
  • the plant and/or flower preservation composition of the invention can take any form known in the art that renders it suitable to be applied to plant and/or flowers (optionally after addition to water).
  • the form of the plant and/or flower preservation composition is liquid, e.g. a solution, suspension or emulsion.
  • the preservation composition of the invention may further comprise an active ingredient.
  • the active ingredient and lactam and/or a eutectic composition comprising a lactam and a eutecting agent can be used in similar amounts as described above for crop enhancement compositions. Examples of suitable active ingredients, lactam and eutecting agent can also be found in the description above. The skilled person will understand which active ingredients can be suitably used in plant and/or flower preservation compositions.
  • the plant and/or flower preservation composition of the invention may further comprise additives as described above.
  • the present invention further pertains to a herbicide composition comprising a lactam and/or a eutectic composition comprising a lactam and a eutecting agent, and optionally water.
  • the plant propagation material dies.
  • the exact effective herbicidal amount will depend on the plant propagation material. (Well) below the effective herbicidal amount, the lactam and/or the eutectic composition comprising the lactam and the eutecting agent may act as a crop enhancement agent as described above. Without being bound by theory, it is believed that applying a higher concentration of the herbicide composition to soil and/or to the plant propagation material water is retained to such an extent that it cannot be used advantageously for the plant propagation material rendering the material to die eventually.
  • the herbicide composition of the invention may further comprise an active ingredient.
  • the active ingredient and lactam and/or a eutectic composition comprising a lactam and a eutecting agent can be used in amounts effective to achieve a herbicidal effect, which is generally considerably higher than amounts as described above for crop enhancement compositions. Examples of suitable active ingredients, lactam and eutecting agent can also be found in the description above.
  • the herbicide composition of the invention may further comprise additives as described above.
  • the invention further pertains to a method of controlling undesired vegetation in crops of useful plants, which comprises allowing a herbicidally effective amount of the herbicide composition of the invention to act where control is desired.
  • crops of useful plants is meant the crops that are harvested for commercial purposes including the food and feed market. Such crops are generally known in the art and include corn, soy, wheat, rice as well as genetically modified crops such as herbicide-resistant corn.
  • undesired vegetation refers to vegetation that is not a crop of useful plants such as weeds and grasses, which may limit the growth and harvest of useful plants.
  • The“herbicidally effective amount” refer to an amount effective, at dosages and for periods of time necessary, to achieve the desired herbicidal result. Typically, this amount is higher than the amount necessary for an effective crop enhancement amount.
  • the herbicide composition of the invention is applied to plant propagation material wherein the amount of the lactam and/or eutectic composition comprising lactam and a eutecting agent is at least 2 wt%.
  • the amount is at least 3 wt%, more preferably at least 4 wt% and most preferably at least 5 wt%, and preferably at most 60 wt%, more preferably at most 50 wt%, even more preferably at most 40 wt% and most preferably at most 20 wt%.
  • the herbicide composition of the invention may be applied to treat a plant propagation material and/or its surroundings before or after the plant propagation material was planted or sown.
  • the herbicide composition can be applied as a soil treatment, a foliar treatment or a seed treatment.
  • the herbicide composition of the invention can be in any form known in the art. Examples of such forms include solutions, emulsions, granules, powders and pellets.
  • the invention further pertains to the use of the herbicide composition of the invention as a herbicide.
  • the invention is exemplified in the following Examples.
  • Example 1 g-butyrolactam and e-caprolactam (weight ratio 1 :1 )
  • Example 2 g-butyrolactam and e-caprolactam (weight ratio 2:1 )
  • Example 3 g-butyrolactam and e-caprolactam (weight ratio 1 :1 ) garlic seeds
  • both baskets were placed outside at a temperature below 7 °C (varying over the next days from -2°C to 6°C). Under these conditions, the seeds treated with the eutectic composition grew faster than the seeds treated with water alone.
  • both baskets were placed outside at varying temperatures ranging from 2 to 16°C.
  • the plants were treated for the next 5 days in which the plants still evenly grew.
  • the plants treated with the eutectic composition of the invention did grow and the leaves maintained their green colour.
  • the soil was still moist after 8 days of drought.
  • Example 6 g-butyrolactam and e-caprolactam (weight ratio 1 :1 ) common daisy flower
  • Example 7 g-butyrolactam and e-caprolactam (weight ratio 1 :1 ) grass plot
  • Example 1 The eutectic composition of Example 1 was added to water in an amount of 2 wt%. A part of a outside grass plot containing grass and moss was sprayed once with the eutectic composition of the invention. After 2 days the grass and moss were brown. After 1 week the grass and moss had not grown back and was still dead.
  • Example 8 e-caprolactam: bird seeds
  • each of the baskets 50 bird seeds (blend of seeds) were evenly spread and sown in soil e- caprolactam was added to water in an amount of 0.2 wt%.
  • the first basket was sprayed on the first day with the caprolactam solution of the invention.
  • the second basket was sprayed with water (without e-caprolactam).
  • the following days both baskets were sprayed with water (without the eutectic composition).
  • the bird seeds in the first basket germinated and grew above soil at the same time as the seeds in the second basket. For the next 10 days the resulting plants in both baskets grew evenly and uniformly.
  • both baskets were placed outside at varying temperatures ranging from 2 to 16°C.
  • the plants were treated for the next 5 days in which the plants still evenly grew.
  • the plants treated with the caprolactam composition of the invention did grow and the leaves maintained their green colour.
  • Example 9 e-caprolactam and water (weight ratio 9:1 ): separated broad leaf
  • a fresh broad leaf was taken and half of the leaf was treated with a composition of e- caprolactam and water in a weight ratio of 9:1. After 10 days, the untreated part of the leaf turned brown and curled up; the treated part of the leaf was lighter green and maintained its original shape (straight and broad).

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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Agronomy & Crop Science (AREA)
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Abstract

L'invention concerne une composition d'amélioration de récolte comprenant une composition de lactame et/ou eutectique comprenant un lactame et un agent eutectique, et éventuellement de l'eau. L'invention concerne en outre une composition herbicide comprenant une composition de lactame et/ou eutectique comprenant un lactame et un agent eutectique, et éventuellement de l'eau.
PCT/EP2020/062187 2019-05-01 2020-05-01 Composition d'amélioration de récolte WO2020221919A1 (fr)

Applications Claiming Priority (4)

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EP19172102 2019-05-01
EP19172102.6 2019-05-01
EP19020632 2019-11-12
EP19020632.6 2019-11-12

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