WO2001051432A1 - Aqueous means containing micronutrients for plants - Google Patents

Aqueous means containing micronutrients for plants Download PDF

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Publication number
WO2001051432A1
WO2001051432A1 PCT/EP2000/013265 EP0013265W WO0151432A1 WO 2001051432 A1 WO2001051432 A1 WO 2001051432A1 EP 0013265 W EP0013265 W EP 0013265W WO 0151432 A1 WO0151432 A1 WO 0151432A1
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compounds
formula
saturated
micronutrients
branched
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PCT/EP2000/013265
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German (de)
French (fr)
Inventor
Horst-Werner Wollenweber
Hans-Georg Mainx
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Cognis Deutschland Gmbh & Co. Kg
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Priority to AU23697/01A priority Critical patent/AU2369701A/en
Publication of WO2001051432A1 publication Critical patent/WO2001051432A1/en

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    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05D—INORGANIC FERTILISERS NOT COVERED BY SUBCLASSES C05B, C05C; FERTILISERS PRODUCING CARBON DIOXIDE
    • C05D9/00—Other inorganic fertilisers
    • C05D9/02—Other inorganic fertilisers containing trace elements
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
    • C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
    • C05G3/50—Surfactants; Emulsifiers
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
    • C05G5/00—Fertilisers characterised by their form
    • C05G5/20—Liquid fertilisers
    • C05G5/27—Dispersions, e.g. suspensions or emulsions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/40—Bio-organic fraction processing; Production of fertilisers from the organic fraction of waste or refuse

Definitions

  • the present invention relates to aqueous compositions which contain micronutrients for plants, a process for increasing plant growth and the use of alkoxylated fatty acid esters to increase the penetration of micronutrients in plants.
  • micronutrients In addition to water, nitrogen and carbon dioxide, plants need so-called micronutrients to grow, albeit in small quantities. This includes inorganic or organic compounds of manganese, calcium, iron, magnesium, selenium, cobalt, nickel and zinc, which only have to be available to the plants in very small quantities, but which are nevertheless essential for plant growth. Common full fertilizers therefore contain e.g. also these connections for an adequate supply of the plants.
  • the micronutrients which are often also applied separately in the form of aqueous formulations, are not always absorbed to a sufficient extent by the plants, in particular because of the relative impermeability of the wax-containing, hydrophobic cuticle of the plant leaves. Therefore, relatively highly concentrated agents, which are therefore comparatively expensive, are often necessary in order to enable the plants to be adequately supplied with the essential nutrients.
  • aqueous compositions which contain micronutrients for plants and alkoxylated fatty acid esters determined as emulsifiers permit a very high penetration of these active substances into the plant.
  • the present application therefore relates to aqueous compositions which contain micronutrients for plants and one or more compounds of the general formula (I)
  • R in the RO stands for an alcohol radical selected from the group of the branched or linear, saturated or unsaturated monohydric alcohols with 1 to 6 C atoms or the polyols with 2 to 12 C atoms and 2 to 6 hydroxyl groups and R 'represents hydrogen and / or a group -CO- R "is in which R" is a branched or linear, saturated or unsaturated alkyl radical having 5 to 29 carbon atoms, n is a number between 1 and 50 and m is zero or a number between 1 and 10.
  • the agents according to the invention contain micronutrients for plants, preferably inorganic or organic compounds of manganese, calcium, iron, magnesium, selenium, cobalt, nickel and / or zinc.
  • the micronutrients are preferably used in the form of their inorganic salts, e.g. Carbonates, sulfates or phosphates.
  • the agents according to the invention are available as a suspension or solution.
  • alkoxylated compounds of the formula (I) are known substances which are described, for example, in US 2,678,935, US 3,539,518, US 4,022,808 or GB 1,050,497, the disclosure of which is also part of the present application.
  • the compounds of formula (I) can be prepared by all methods known to those skilled in the art, e.g. by esterification of fatty acids with alkoxylated methanol, as described in US Pat. No. 3,539,518.
  • this process has some disadvantages, it has two stages, the esterification takes a very long time and the products are colored by the high reaction temperatures.
  • fatty acid methyl ester ethoxylates produced in this way have relatively high OH numbers after the esterification, which can be problematic for some applications.
  • Another possibility is the direct reaction of fatty acid esters with alkylene oxides in the presence of transition metal catalysts, as described in US Pat. No. 4,022,808.
  • the fatty acid alkyl ester alkoxylates are preferably prepared by heterogeneously catalyzed direct alkoxylation of fatty acid alkyl esters with ethylene oxide and / or propylene oxide on calcined or hydrophobized hydrotalcites.
  • This synthesis method is described in detail in the laid-open publications WO 90/13533 and WO 91/15441, the disclosure of which is also part of the present application.
  • the resulting products are characterized by a low OH number, the reaction is carried out in one step and light-colored products are obtained.
  • the fatty acid alkyl esters used as starting materials can be obtained from natural oils and fats or produced synthetically.
  • the alkoxylated fatty acid esters contain at least 1 mole of ethylene oxide groups per mole of ester. Preference is given to compounds of the formula (I) which contain between 1 and 50, preferably 1 and 30, mol of ethylene oxide per mole of ester. It is preferred that in addition to the ethylene oxide units between one and 10 propylene oxide groups are still contained in the molecule. Those compounds of the formula (I) which contain between 1 and 30 moles of ethylene oxide per mole of ester and 1 to 10 moles of propylene oxide groups are also preferred.
  • mixed ethylene oxide / propylene oxide adducts can be used both those compounds which have been reacted with a mixture of ethylene oxide and propylene oxide, but also compounds which have been reacted in two separate steps with ethylene oxide and propylene oxide.
  • the alkoxides are statistically distributed among the OH groups present.
  • Suitable fatty acid components are natural or synthetic fatty acids, in particular straight-chain, saturated or unsaturated C6-C30 fatty acids, including technical mixtures thereof, as are obtainable by fat cleavage from animal and vegetable fats and oils, e.g.
  • caprylic capric, lauric, laurolein, myristic, myristoleic, palmitic, palmitoleic, oleic, elaidic, arachic, gadoic, behenic and erucic acid.
  • Straight-chain or branched, saturated or unsaturated monohydric alcohols having 1 to 6 carbon atoms e.g. Methanol, ethanol, n- and i-propanol, n- and i-butanol, pentanol, hexanol, 2-ethylhexanol and cyclohexanol are suitable.
  • Polyols having 2 to 6 carbon atoms for example, ethylene glycol, 1,2-propylene glycol, 1,2-butylene glycol glycerol or trimethylolpropane and penthaerythritol can be used.
  • the agents can therefore contain both compounds of the formula (I) which are obtained by reacting the full esters and the partial esters with alkoxides.
  • alkoxylated fatty acid esters of the formula (I) whose fatty acid component is selected from linear, unbranched C ⁇ to cis fatty acids and whose alcohol component is methanol, these esters of the formula (I) preferably between 1 and 3 mol of propylene oxide and contain between 1 and 6 moles of ethylene oxide per mole of ester.
  • Such compounds can be obtained, for example, by the above-described reactions of palmitic, stearic, oleic, linolinic or linolenic acid, lauric and myristic acid or their esters with alkoxides.
  • alkoxyated compounds in which glycerol is used as the alcohol component and the fatty acid component is selected from saturated or unsaturated, branched or unbranched fatty acids with 18 to 22 carbon atoms and the esters contain between 1 and 3 moles of ethylene oxide per mole of ester.
  • Compounds of the formula (I) in which n is 5, 10 or 30 and m is zero are particularly preferred.
  • Such compounds can be obtained, for example, by reacting glycerol esters of natural fatty acids such as, for example, palm, rapeseed, soybean or, preferably, castor oil with ethylene oxide.
  • the compounds of the formula (I) contained in the agents according to the invention are nonionic compounds which are additionally characterized by their HLB value (hydrophilic-lipophilic balance as defined by Griffin; see Römpp Lexikon Chemie, 10th edition 1997, page 1764) can be. Those agents are preferred which contain compounds of the formula (I) with HLB values between 4 and 10 and in particular between 5 and 9.
  • the agents contain at least one micronutrient, but preferably mixtures of different micronutrients in amounts suitable for the respective plant.
  • Agents which contain between 0.01 and 15% by weight of micronutrients, based on the weight of the agents, are preferred. However, it can also contain other constituents usually contained in fertilizers. These include compounds containing ammonium and phosphorus, such as urea and its derivatives or lecithins. These also include solvents such as ethylene or propylene glycols and C 1 -C 6 alcohols, solid carriers such as lignin, lignin derivatives or clays and other known emulsifiers or dispersants.
  • agents which contain only emulsifiers of the formula (I) and otherwise no further emulsifiers or dispersants. If the composition according to the invention also contains other constituents of the type mentioned above, these are present in amounts of 0.01 to 10% by weight.
  • the water content of the agents according to the invention is preferably between 10 and 99.9% by weight, preferably 30 to 99 and in particular 50 to 95% by weight.
  • compositions according to the invention are stable in storage at temperatures above 30 ° C. and can be produced without the action of high shear forces, for example by manual stirring.
  • the agents according to the invention are formed without the use of strong shear forces, e.g. by simply stirring by hand.
  • the compounds of the formula (I) can be introduced, for example, in liquid form.
  • the active ingredient is then added and this mixture is dispersed in water.
  • compounds of the formula (I) with melting points above room temperature are used, they can be used in molten form.
  • an aqueous agent having the composition described above being applied to the plants, preferably to their aerial parts, for example by spraying.
  • the present invention further relates to the use of compounds of the formula (I) for increasing the penetration of micronutrients in plants.
  • the combination of the micronutrients with the compounds of the formula (I) leads to improved penetration into the plant, preferably through the waxy cuticle on the leaf surface.
  • the agents according to the present invention can also be applied via the roots.
  • the use of the combination of micronutrients and compounds of the formula (I) leads to a substantial saving in micronutrients which, compared to the prior art, enables the concentration of micronutrients in the agent to be reduced by a factor of 3 to 10. Examples
  • the compound of formula (I) was contained in amounts of 0.01% by weight, based on the total agent.
  • the concentration of MnC0 3 was 0.2% by weight.
  • 0.1 ul of the aqueous agent was applied to the leaves of deadly cherries. The penetration was then measured after 48 hours. A significantly increased penetration rate was measured compared to commercially available agents that contained ethoxylated nonylphenol.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Fertilizers (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention relates to aqueous means containing micronutrients, such as calcium, iron, cobalt, magnesium, mangane, nickel and/or zinc, for plants and compounds of the general formula (I): RO-(C2H4O)n(C3H6O)m-R', wherein RO stands for an alcohol radical selected from the group of the branched or linear, saturated or unsaturated monovalent alcohols with 1 to 6 C-atoms or of the polyols with 2 to 12 C atoms and 2 to 6 hydroxyl groups and R' stands for hydrogen and/or an ester group CO-R'', wherein R'' means a branched or linear, saturated or unsaturated alkyl radical with 5 to 29 C atoms, n is a number between 1 and 50 and m is zero or a number between 1 and 10. An increased amount of said micronutrients pertaining to the inventive means penetrate the plant via the leaves.

Description

Wäßrige Mittel, die Mikronährstoffe für Pflanzen enthalten Aqueous agents containing micronutrients for plants
Die vorliegenden Erfindung betrifft wäßrige Mittel, die Mikronährstoffe für Pflanzen enthalten, ein Verfahren zur Steigerung des Pflanzenwachstums sowie die Verwendung von alkoxylierten Fettsäureestern zur Steigerung der Penetration von Mikronährstoffen in Pflanzen.The present invention relates to aqueous compositions which contain micronutrients for plants, a process for increasing plant growth and the use of alkoxylated fatty acid esters to increase the penetration of micronutrients in plants.
Pflanzen benötigen zum Wachstum neben Wasser, Stickstoff und Kohlendioxid, wenn auch in untergeordnete Mengen noch sogenannte Mikronährstoffe. Darunter werden anorganische oder organische Verbindungen des Mangans, Calciums, Eisens, Magnesiums, Selens, Kobalts, Nickels und Zinks zusammengefasst, die zwar nur in sehr geringen Mengen für die Pflanzen verfügbar sein müssen, die aber trotzdem essentiell für das Pflanzenwachstum sind. Übliche Volldüngemittel enthalten daher z.B. auch diese Verbindungen für eine ausreichende Versorgung der Pflanzen. Allerdings werden die Mikronährstoffe, die häufig auch separat in Form wäßriger Formulierungen appliziert werden, nicht immer in ausreichendem Maße von den Pflanzen, insbesondere aufgrund der relativen Undurchlässigkeit der wachshaltigen, hydrophoben Kutikula der Pflanzenblätter, aufgenommen. Daher sind häufig relativ hoch konzentrierte Mittel, die daher vergleichsweise teuer sind notwendig, um eine ausreichende Versorgung der Pflanzen mit den essentiellen Nährstoffen zu ermöglichen.In addition to water, nitrogen and carbon dioxide, plants need so-called micronutrients to grow, albeit in small quantities. This includes inorganic or organic compounds of manganese, calcium, iron, magnesium, selenium, cobalt, nickel and zinc, which only have to be available to the plants in very small quantities, but which are nevertheless essential for plant growth. Common full fertilizers therefore contain e.g. also these connections for an adequate supply of the plants. However, the micronutrients, which are often also applied separately in the form of aqueous formulations, are not always absorbed to a sufficient extent by the plants, in particular because of the relative impermeability of the wax-containing, hydrophobic cuticle of the plant leaves. Therefore, relatively highly concentrated agents, which are therefore comparatively expensive, are often necessary in order to enable the plants to be adequately supplied with the essential nutrients.
Überraschenderweise wurde gefunden, daß wäßrige Mittel, die Mikronährstoffe für Pflanzen und als Emulgatoren bestimmte alkoxyiierte Fettsäureester enthalten eine sehr hohe Penetration dieser Wirkstoffe in die Pflanze ermöglichen.Surprisingly, it has been found that aqueous compositions which contain micronutrients for plants and alkoxylated fatty acid esters determined as emulsifiers permit a very high penetration of these active substances into the plant.
Gegenstand der vorliegenden Anmeldung sind daher wäßrige Mittel, die Mikronährstoffe für Pflanzen enthalten und eine oder mehrere Verbindungen der allgemeinen Formel (I)The present application therefore relates to aqueous compositions which contain micronutrients for plants and one or more compounds of the general formula (I)
RO-(C2H40)n(C3H6θ)m-R' (I)RO- (C 2 H 4 0) n (C3H6θ) m -R '(I)
in der RO für einen Alkoholrest, ausgewählt aus der Gruppe der verzweigten oder linearen, gesättigten oder ungesättigten einwertigen Alkohole mit 1 bis 6 C-Atomen oder der Polyole mit 2 bis 12 C-Atomen und 2 bis 6 Hydroxylgruppen steht und R' für Wasserstoff und/oder eine Gruppe -CO- R" steht, in der R" einen verzweigten oder linearen, gesättigten oder ungesättigten Alkylrest mit 5 bis 29 C-Atomen bedeutet, n eine Zahl zwischen 1 und 50 ist und m Null ist oder eine Zahl zwischen 1 und 10 bedeutet.in the RO stands for an alcohol radical selected from the group of the branched or linear, saturated or unsaturated monohydric alcohols with 1 to 6 C atoms or the polyols with 2 to 12 C atoms and 2 to 6 hydroxyl groups and R 'represents hydrogen and / or a group -CO- R "is in which R" is a branched or linear, saturated or unsaturated alkyl radical having 5 to 29 carbon atoms, n is a number between 1 and 50 and m is zero or a number between 1 and 10.
Die erfindungsgemäßen Mittel enthalten Mikronährstoffe für Pflanzen, vorzugsweise anorganische oder organische Verbindungen von Mangan, Calcium, Eisen, Magnesium, Selen, Kobalt, Nickel und/oder Zink. Vorzugsweise werden die Mikronährstoffe in Form ihrer anorganischen Salze eingesetzt, z.B. Carbonate, Sulfate oder Phosphate. Je nach Löslichkeit der Mikronährstoffe liegen die erfindungsgemäßen Mittel als Suspension oder Lösung vor.The agents according to the invention contain micronutrients for plants, preferably inorganic or organic compounds of manganese, calcium, iron, magnesium, selenium, cobalt, nickel and / or zinc. The micronutrients are preferably used in the form of their inorganic salts, e.g. Carbonates, sulfates or phosphates. Depending on the solubility of the micronutrients, the agents according to the invention are available as a suspension or solution.
Die alkoxylierten Verbindungen der Formel (I) sind bekannte Substanzen, die beispielsweise in der US 2,678,935, US 3,539,518, US 4,022,808 oder GB 1,050,497 beschrieben werden, deren Offenbarung auch Teil der vorliegenden Anmeldung ist.The alkoxylated compounds of the formula (I) are known substances which are described, for example, in US 2,678,935, US 3,539,518, US 4,022,808 or GB 1,050,497, the disclosure of which is also part of the present application.
Die Verbindungen der Formel (I) können durch alle dem Fachmann bekannten Methoden hergestellt werden, z.B. durch Veresterung von Fettsäuren mit alkoxyliertem Methanol, wie es die US 3,539,518 beschreibt. Dieses Verfahren ist jedoch mit einigen Nachteilen verbunden, es verläuft zweistufig, die Veresterung dauert sehr lange und die Produkte sind durch die hohen Reaktionstemperaturen gefärbt. Außerdem besitzen solchermaßen hergestellte Fettsäuremethylesterethoxylate nach der Veresterung relativ hohe OH-Zahlen, was für manche Anwendungen problematisch sein kann. Eine weitere Möglichkeit besteht in der direkten Umsetzung von Fettsäureestern mit Alkylenoxiden in Gegenwart von Übergangsmetallkatalysatoren, wie in der US 4,022,808 beschrieben. Vorzugsweise werden die Fettsäurealkylesteralkoxylate aber durch eine heterogen katalysierte Direktalkoxylierung von Fettsäurealkylestern mit Ethylenoxid und/oder Propylenoxid an calcinierten bzw. hydrophobierten Hydrotalciten hergestellt. Dieses Syntheseverfahren sind in den Offenlegungsschriften WO 90/13533 und WO 91/15441, deren Offenbarung auch Teil der vorliegenden Anmeldung ist, ausführlich beschrieben. Die dabei entstehenden Produkte zeichnen sich durch eine niedrige OH-Zahl aus, die Reaktion wird einstufig durchgeführt und man erhält hellfarbige Produkte. Die als Ausgangsstoffe dienenden Fettsäurealkylester können sowohl aus natürlichen Ölen und Fetten gewonnen als auch auf synthetischem Wege hergestellt werden.The compounds of formula (I) can be prepared by all methods known to those skilled in the art, e.g. by esterification of fatty acids with alkoxylated methanol, as described in US Pat. No. 3,539,518. However, this process has some disadvantages, it has two stages, the esterification takes a very long time and the products are colored by the high reaction temperatures. In addition, fatty acid methyl ester ethoxylates produced in this way have relatively high OH numbers after the esterification, which can be problematic for some applications. Another possibility is the direct reaction of fatty acid esters with alkylene oxides in the presence of transition metal catalysts, as described in US Pat. No. 4,022,808. However, the fatty acid alkyl ester alkoxylates are preferably prepared by heterogeneously catalyzed direct alkoxylation of fatty acid alkyl esters with ethylene oxide and / or propylene oxide on calcined or hydrophobized hydrotalcites. This synthesis method is described in detail in the laid-open publications WO 90/13533 and WO 91/15441, the disclosure of which is also part of the present application. The resulting products are characterized by a low OH number, the reaction is carried out in one step and light-colored products are obtained. The fatty acid alkyl esters used as starting materials can be obtained from natural oils and fats or produced synthetically.
Die alkoxylierten Fettsäureester enthalten mindestens 1 Mol Ethylenoxidgruppen pro Mol Ester. Bevorzugt sind Verbindungen der Formel (I), die pro Mol Ester zwischen 1 und 50, vorzugsweise 1 und 30 Mol Ethylenoxid enthalten. Es ist bevorzugt, daß zusätzlich zu den Ethylenoxid-Einheiten noch zwischen einer und 10 Propylenoxidgruppen im Molekül enthalten sind. Bevorzugt sind auch solche Verbindungen der Formel (I), die zwischen 1 und 30 Mol Ethylenoxid pro Mol Ester und 1 bis 10 Mol Propylenoxidgruppen enthalten. Bei diesen gemischten Ethylenoxid/Propylenoxid-Addukten können sowohl solche Verbindungen verwendet werden, die mit einer Mischung aus Ethylenoxid und Propylenoxid umgesetzt wurden, aber auch Verbindungen, die in zwei getrennten Schritten mit Ethylenoxid und Propylenoxid umgesetzt wurden. Die Alkoxide verteilen sich in Abhängigkeit vom Herstellverfahren statistisch auf die vorhandenen OH-Gruppen.The alkoxylated fatty acid esters contain at least 1 mole of ethylene oxide groups per mole of ester. Preference is given to compounds of the formula (I) which contain between 1 and 50, preferably 1 and 30, mol of ethylene oxide per mole of ester. It is preferred that in addition to the ethylene oxide units between one and 10 propylene oxide groups are still contained in the molecule. Those compounds of the formula (I) which contain between 1 and 30 moles of ethylene oxide per mole of ester and 1 to 10 moles of propylene oxide groups are also preferred. These mixed ethylene oxide / propylene oxide adducts can be used both those compounds which have been reacted with a mixture of ethylene oxide and propylene oxide, but also compounds which have been reacted in two separate steps with ethylene oxide and propylene oxide. Depending on the manufacturing process, the alkoxides are statistically distributed among the OH groups present.
Werden Verbindungen der Formel (I) eingesetzt, die als Alkoholrest RO Polyole enthalten, so beziehen sich die Angaben zur Menge der Ethylen- bzw. Propylenoxideinheiten (Indizes n und m) immer auf das gesamte Molekül. Die genaue Verteilung der Ethylen- bzw. Propylenoxideinheiten auf die verschiedenen Hydroxylgruppen der Polyole gehorcht aber bekanntermaßen einer vom Syntheseverfahren abhängigen statistischen Verteilungen.If compounds of the formula (I) are used which contain RO as the alcohol radical RO, the information on the amount of ethylene or propylene oxide units (indices n and m) always relates to the entire molecule. However, it is known that the exact distribution of the ethylene or propylene oxide units among the various hydroxyl groups of the polyols obeys a statistical distribution which is dependent on the synthesis process.
Die Fettsäureesterreste -CO-R" enthalten Alkylreste R" mit 5 bis 29 C-Atomen. Als Fettsäurekomponente eignen sich natürliche oder synthetische Fettsäuren, insbesondere geradkettigte, gesättigte oder ungesättigte C6-C30 Fettsäuren, einschließlich technischer Gemische derselben, wie sie durch Fettspaltung aus tierischen und pflanzlichen Fetten und Ölen zugänglich sind, z.B. aus Kokosöl, Palmkernöl, Sojaöl, Sonnenblumenöl, Rüböl, Baumwollsaatöl, Fischöl, Rindertalg und Schweineschmalz; spezielle Beispiele sind Capryl-, Caprin-, Laurin-, Laurolein-, Myristin-, Myristolein-, Palmitin-, Palmitolein-, Öl-, Elaidin-, Arachin-, Gadoiein-, Behen- und Erucasäure.The fatty acid ester residues -CO-R "contain alkyl residues R" with 5 to 29 carbon atoms. Suitable fatty acid components are natural or synthetic fatty acids, in particular straight-chain, saturated or unsaturated C6-C30 fatty acids, including technical mixtures thereof, as are obtainable by fat cleavage from animal and vegetable fats and oils, e.g. from coconut oil, palm kernel oil, soybean oil, sunflower oil, rape oil, cottonseed oil, fish oil, beef tallow and lard; specific examples are caprylic, capric, lauric, laurolein, myristic, myristoleic, palmitic, palmitoleic, oleic, elaidic, arachic, gadoic, behenic and erucic acid.
Als Alkoholkomponente RO sind geradkettigte oder verzweigte, gesättigte oder ungesättigte einwertige Alkohole mit 1 bis 6 C-Atomen, z.B. Methanol, Ethanol, n- und i-Propanol, n- und i- Butanol, Pentanol, Hexanol, 2-Ethylhexanol und Cyclohexanol geeignet. Als Polyole mit 2 bis 6 C- Atomen können beispielsweise Ethylenglykol,- 1 ,2-Propylenglykol, 1 ,2-Butylenglykol Glycerin oder Trimethylolpropan und Penthaerythrit verwendet werden.Straight-chain or branched, saturated or unsaturated monohydric alcohols having 1 to 6 carbon atoms, e.g. Methanol, ethanol, n- and i-propanol, n- and i-butanol, pentanol, hexanol, 2-ethylhexanol and cyclohexanol are suitable. Polyols having 2 to 6 carbon atoms, for example, ethylene glycol, 1,2-propylene glycol, 1,2-butylene glycol glycerol or trimethylolpropane and penthaerythritol can be used.
Grundsätzlich sind alle Hydroxylgruppen der Alkohole mit den Alkoxiden substituiert, allerdings sind nicht alle endständigen Alkoxidreste mit Estergruppen verschlossen. Wird von Polyolen als Alkoholkomponente RO ausgegangen, wie Glycerin oder Ethylenglykol, können die Mittel daher sowohl Verbindungen der Formel (I) enthalten, die durch Umsetzung der Vollester als auch der Partialester mit Alkoxiden erhalten werden. Es sind aber solche Verbindungen der Formel (I) bevorzugt, bei denen alle Hydroxlygruppen der Alkohole alkoxyliert und weiterhin alle endständigen Alkoxid-Gruppen mit Estergruppen der Formel -CO-R" verschlossen sind. Bei diesen bevorzugten Verbindungen steht der Rest R" in der Formel (I) daher ausschließlich für einen verzweigten oder linearen, gesättigten oder ungesättigten Alkylrest mit 5 bis 29 C-Atomen.Basically, all hydroxyl groups of the alcohols are substituted with the alkoxides, but not all terminal alkoxide residues are sealed with ester groups. If polyols are used as the alcohol component RO, such as glycerol or ethylene glycol, the agents can therefore contain both compounds of the formula (I) which are obtained by reacting the full esters and the partial esters with alkoxides. However, preference is given to those compounds of the formula (I) in which all the hydroxyl groups of the alcohols are alkoxylated and all terminal alkoxide groups are furthermore sealed with ester groups of the formula -CO-R " Compounds the radical R "in formula (I) therefore stands exclusively for a branched or linear, saturated or unsaturated alkyl radical having 5 to 29 carbon atoms.
In den erfindungsgemäßen Mitteln werden weiterhin vorzugsweise solche alkoxylierten Fettsäureester der Formel (I) eingesetzt, deren Fettsäurekomponente ausgewählt ist aus linearen, unverzweigten Cδ bis Cis Fettsäuren und deren Alkoholkomponente Methanol darstellt, wobei diese Ester der Formel (I) vorzugsweise zwischen 1 und 3 Mol Propylenoxid und zwischen 1 und 6 Mol Ethylenoxid pro Mol Ester enthalten. Solche Verbindungen können beispielsweise durch die oben beschriebenen Reaktionen von Palmitin-, Stearin-, Olein-, Linolin- oder Linolensäure Laurin- und Myristinsäure bzw. deren Estern mit Alkoxiden erhalten werden.In the agents according to the invention, preference is furthermore given to using alkoxylated fatty acid esters of the formula (I) whose fatty acid component is selected from linear, unbranched Cδ to cis fatty acids and whose alcohol component is methanol, these esters of the formula (I) preferably between 1 and 3 mol of propylene oxide and contain between 1 and 6 moles of ethylene oxide per mole of ester. Such compounds can be obtained, for example, by the above-described reactions of palmitic, stearic, oleic, linolinic or linolenic acid, lauric and myristic acid or their esters with alkoxides.
Geeignet sind auch alkoxyiierte Verbindungen, bei denen als Alkoholkomponente Glycerin verwendet wird und die Fettsäurekomponente ausgewählt wird aus gesättigten oder ungesättigten, verzweigten oder unverzweigten Fettsäuren mit 18 bis 22 C-Atomen und die Ester zwischen 1 und 3 Mol Ethylenoxid pro Mol Ester enthalten. Besonders bevorzugt sind Verbindungen der Formel (I), in denen n 5, 10 oder 30 bedeutet und m Null ist. Derartige Verbindungen können beispielsweise durch Umsetzung von Glycerinestem natürlicher Fettsäuren wie beispielsweise Palm-, Raps-, Soja- oder vorzugsweise von Ricinusöl mit Ethylenoxid erhalten werden.Also suitable are alkoxyated compounds in which glycerol is used as the alcohol component and the fatty acid component is selected from saturated or unsaturated, branched or unbranched fatty acids with 18 to 22 carbon atoms and the esters contain between 1 and 3 moles of ethylene oxide per mole of ester. Compounds of the formula (I) in which n is 5, 10 or 30 and m is zero are particularly preferred. Such compounds can be obtained, for example, by reacting glycerol esters of natural fatty acids such as, for example, palm, rapeseed, soybean or, preferably, castor oil with ethylene oxide.
Die in den erfindungsgemäßen Mitteln enthaltenen Verbindungen der Formel (I) sind nichtionische Verbindungen, die zusätzlich auch durch ihren HLB-Wert (hydrophilic-lipophilic-balance gemäß der Definition von Griffin; siehe Römpp Lexikon Chemie, 10. Auflage 1997, Seite 1764) charakterisiert werden können. Es sind solche Mittel bevorzugt, die Verbindungen der Formel (I) mit HLB-Werten zwischen 4 und 10 und insbesondere zwischen 5 und 9 enthalten.The compounds of the formula (I) contained in the agents according to the invention are nonionic compounds which are additionally characterized by their HLB value (hydrophilic-lipophilic balance as defined by Griffin; see Römpp Lexikon Chemie, 10th edition 1997, page 1764) can be. Those agents are preferred which contain compounds of the formula (I) with HLB values between 4 and 10 and in particular between 5 and 9.
Die Mittel enthalten mindestens einen Mikronährstoff, vorzugsweise aber Abmischungen verschiedener Mikronährstoffe in für die jeweilige Pflanze geeigneten Mengen. Bevorzugt sind Mittel, die zwischen 0,01 und 15 Gew.-% an Mikronährstoffen, bezogen auf das Gewicht der Mittel, enthalten. Es können aber noch weitere in Düngemittel üblicherweise enthaltende Bestandteile enthalten sein. Dazu zählen ammonium- und phosphorhaltige Verbindungen, wie Harnstoff und dessen Derivate oder Lecithine. Dazu zählen weiterhin Lösungsmittel, wie Ethlyen- oder Propylenglykole und Cι-C6-Alkohole, feste Trägerstoffe, wie Lignin, Lignin-Derivate oder Tone und weitere bekannte Emulgatoren bzw. Dispergatoren. Besonders bevorzugt sind jedoch solche Mittel, die ausschließlich Emulgatoren der Formel (I) enthalten und ansonsten keine weiteren Emulgatoren oder Dispergatoren enthalten. Sind in den erfindungsgemäßen Mittel noch andere Bestandteile der oben angesprochenen Art enthalten, so liegen diese in Mengen von 0,01 bis 10 Gew.-% vor. Der Wasseranteil der erfindungsgemäßen Mittel liegt vorzugsweise zwischen 10 und 99,9 Gew.-%, vorzugsweise 30 bis 99 und insbesondere 50 bis 95 Gew.-%.The agents contain at least one micronutrient, but preferably mixtures of different micronutrients in amounts suitable for the respective plant. Agents which contain between 0.01 and 15% by weight of micronutrients, based on the weight of the agents, are preferred. However, it can also contain other constituents usually contained in fertilizers. These include compounds containing ammonium and phosphorus, such as urea and its derivatives or lecithins. These also include solvents such as ethylene or propylene glycols and C 1 -C 6 alcohols, solid carriers such as lignin, lignin derivatives or clays and other known emulsifiers or dispersants. However, particular preference is given to agents which contain only emulsifiers of the formula (I) and otherwise no further emulsifiers or dispersants. If the composition according to the invention also contains other constituents of the type mentioned above, these are present in amounts of 0.01 to 10% by weight. The water content of the agents according to the invention is preferably between 10 and 99.9% by weight, preferably 30 to 99 and in particular 50 to 95% by weight.
Die erfindungsgemäßen Mittel sind bei Temperaturen von über 30 °C lagerstabil und lassen sich ohne Einwirkung hoher Scherkräfte, beispielsweise durch manuelles Umrühren, herstellen. Die erfindungsgemäßen Mittel bilden sich ohne Anwendung starker Scherkräfte, z.B. durch einfaches Umrühren per Hand. Die Verbindungen der Formel (I) können dazu beispielsweise in flüssiger Form vorgelegt werden. Anschließend wird dann der Wirkstoff zugegeben und diese Mischung in Wasser dispergiert. Werden Verbindung der Formel (I) mit Schmelzpunkten oberhalb der Raumtemperatur eingesetzt, können sie in geschmolzener Form verwendet werden. Es ist aber bevorzugt solche Verbindungen der Formel (I) einzusetzen, die einen Schmelzpunkt unterhalb von 25 °C aufweisen. Es ist aber auch möglich zunächst eine Mischung des agrochemischen Wirkstoffs in Wasser herzustellen und diese Mischung anschließend durch Zugabe von Verbindungen der Formel (I) zu emulgieren bzw. dispergieren.The compositions according to the invention are stable in storage at temperatures above 30 ° C. and can be produced without the action of high shear forces, for example by manual stirring. The agents according to the invention are formed without the use of strong shear forces, e.g. by simply stirring by hand. For this purpose, the compounds of the formula (I) can be introduced, for example, in liquid form. The active ingredient is then added and this mixture is dispersed in water. If compounds of the formula (I) with melting points above room temperature are used, they can be used in molten form. However, preference is given to using those compounds of the formula (I) which have a melting point below 25 ° C. However, it is also possible first to prepare a mixture of the agrochemical active ingredient in water and then to emulsify or disperse this mixture by adding compounds of the formula (I).
Weiterhin wird ein Verfahren zur Steigerung des Pflanzenwachstums beansprucht, wobei auf die Pflanzen, vorzugsweise auf deren oberirdische Teile, eine wäßriges Mittel gemäß der oben beschriebenen Zusammensetzung aufgetragen wird, beispielsweise durch Aufsprühen.Furthermore, a method for increasing plant growth is claimed, an aqueous agent having the composition described above being applied to the plants, preferably to their aerial parts, for example by spraying.
Ein weiterer Gegenstand der vorliegenden Erfindungen betrifft die Verwendung von Verbindungen der Formel (I) zur Steigerung der Penetration von Mikronährstoffen in Pflanzen. Die Kombination der Mikronährstoffe mit den Verbindungen der Formel (I) führt zu einer verbesserten Penetration in die Pflanze, vorzugsweise durch die wachshaltige Kutikuia der Blattoberfläche. Prinzipiell können die Mittel gemäß der vorliegenden Erfindung aber auch über die Wurzeln appliziert werden. Die Verwendung der Kombination aus Mikronährstoffen und Verbindungen der Formel (I) führt zu einer substantiellen Einsparung an Mikronährstoffen, die gegenüber dem Stand der Technik eine Verringerung der Konzentration an Mikronährstoffen in den Mittel um den Faktor 3 bis 10 ermöglicht. BeispieleThe present invention further relates to the use of compounds of the formula (I) for increasing the penetration of micronutrients in plants. The combination of the micronutrients with the compounds of the formula (I) leads to improved penetration into the plant, preferably through the waxy cuticle on the leaf surface. In principle, however, the agents according to the present invention can also be applied via the roots. The use of the combination of micronutrients and compounds of the formula (I) leads to a substantial saving in micronutrients which, compared to the prior art, enables the concentration of micronutrients in the agent to be reduced by a factor of 3 to 10. Examples
Es wurden eine wäßrige Mangancarbonat-haltige Suspension hergestellt, die als erfindungsgemäßes Mittel eine Verbindung der Formel (I) mit RO = Glycerin, R' = COR" mit R" =C16-C18, m= 0, n = 10 enthielt. Die Verbindung der Formel (I) war in Mengen von 0,01 Gew.-%, bezogen auf das gesamte Mittel, enthalten. Die Konzentration des MnC03 betrug 0,2 Gew.-%. 0,1 μl der wäßrigen Mittel wurden auf die Blätter von Tollkirschen aufgebracht. Anschließend wurde die Penetration nach 48 Stunden gemessen. Im Vergleich zu handelsüblichen Mittel, die ethoxyliertes Nonylphenol enthielten wurde eine deutlich gesteigerte Penetrationsrate gemessen. An aqueous suspension containing manganese carbonate was prepared which, as an agent according to the invention, contained a compound of the formula (I) with RO = glycerol, R '= COR "with R" = C16-C18, m = 0, n = 10. The compound of formula (I) was contained in amounts of 0.01% by weight, based on the total agent. The concentration of MnC0 3 was 0.2% by weight. 0.1 ul of the aqueous agent was applied to the leaves of deadly cherries. The penetration was then measured after 48 hours. A significantly increased penetration rate was measured compared to commercially available agents that contained ethoxylated nonylphenol.

Claims

Patentansprüche claims
1. Wäßriges Mittel, enthaltend Mikronährstoffe für Pflanzen, dadurch gekennzeichnet, daß es weiterhin mindestens eine oder mehrere Verbindungen der allgemeinen Formel (I) enthält,1. Aqueous composition containing micronutrients for plants, characterized in that it further contains at least one or more compounds of the general formula (I),
RO-(C2H40)n(C3H60)m-R' (I)RO- (C 2 H 4 0) n (C3H 6 0) m -R '(I)
in der RO für einen Alkoholrest, ausgewählt aus der Gruppe der verzweigten oder linearen, gesättigten oder ungesättigten einwertigen Alkohole mit 1 bis 6 C-Atomen oder der Polyole mit 2 bis 12 C-Atomen und 2 bis 6 Hydroxylgruppen steht und R' für Wasserstoff und/oder eine Estergruppe -CO-R" steht, in der R" einen verzweigten oder linearen, gesättigten oder ungesättigten Alkylrest mit 5 bis 29 C-Atomen bedeutet, n eine Zahl zwischen 1 und 50 ist und m Null ist oder eine Zahl zwischen 1 und 10 bedeutet.in the RO stands for an alcohol radical selected from the group of the branched or linear, saturated or unsaturated monohydric alcohols with 1 to 6 C atoms or the polyols with 2 to 12 C atoms and 2 to 6 hydroxyl groups and R 'represents hydrogen and / or an ester group -CO-R "in which R" is a branched or linear, saturated or unsaturated alkyl radical having 5 to 29 carbon atoms, n is a number between 1 and 50 and m is zero or a number between 1 and 10 means.
2. Mittel nach Anspruch 1 , dadurch gekennzeichnet, daß in den Verbindungen der Formel (I) R" ausschließlich für einen verzweigten oder linearen, gesättigten oder ungesättigten Alkylrest mit 5 bis 29 C-Atomen steht.2. Composition according to claim 1, characterized in that in the compounds of formula (I) R "stands exclusively for a branched or linear, saturated or unsaturated alkyl radical having 5 to 29 carbon atoms.
3. Mittel nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß in den Verbindungen der Formel (I) RO für einen Glycerinrest und R" für einen verzweigten oder linearen, gesättigten oder ungesättigten Alkylrest mit 17 bis 21 C-Atomen steht.3. Composition according to claim 1 or 2, characterized in that in the compounds of formula (I) RO stands for a glycerol residue and R "for a branched or linear, saturated or unsaturated alkyl radical having 17 to 21 carbon atoms.
4. Mittel nach Ansprüchen 1 bis 3, dadurch gekennzeichnet, daß in den Verbindungen der Formel (I) n eine Zahl zwischen 1 und 30 und m 0 oder eine Zahl zwischen 1 und 5 bedeutet.4. Composition according to claims 1 to 3, characterized in that in the compounds of formula (I) n is a number between 1 and 30 and m 0 or a number between 1 and 5.
5. Mittel nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß in den Verbindungen der Formel (I) n für 5, 10 oder 30 steht und m Null bedeutet.5. Agent according to one of claims 1 to 4, characterized in that in the compounds of formula (I) n is 5, 10 or 30 and m is zero.
6. Mittel nach den Ansprüchen 1 bis 5, dadurch gekennzeichnet, daß in den Verbindungen der Formel (I) -CO-R" für einen Ricinolsäurerest und RO für einen Glycerinrest stehen. 6. Composition according to claims 1 to 5, characterized in that in the compounds of formula (I) -CO-R "stand for a ricinoleic acid residue and RO for a glycerol residue.
7. Mittel nach Anspruch 1 , dadurch gekennzeichnet, daß in den Verbindungen der Formel (I) RO für einen Methanolrest und R" für einen verzweigten oder linearen, gesättigten oder ungesättigten Alkylrest mit 5 bis 17 C-Atomen steht.7. Composition according to claim 1, characterized in that in the compounds of formula (I) RO stands for a methanol radical and R "for a branched or linear, saturated or unsaturated alkyl radical having 5 to 17 carbon atoms.
s 8. Mittel nach einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, daß die Verbindungen der Formel (I) einen HLB-Wert zwischen 4 und 10 aufweisen.8. Agent according to one of claims 1 to 7, characterized in that the compounds of formula (I) have an HLB value between 4 and 10.
9. Mittel nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, daß sie zwischen 0,01 und 1 Gew.-% an Verbindungen der Formel (I) enthalten. 09. Composition according to one of claims 1 to 8, characterized in that they contain between 0.01 and 1 wt .-% of compounds of formula (I). 0
10. Mittel nach einem der Ansprüche 1 bis 9, dadurch gekennzeichnet, daß die Mikronährstoffe ausgewählt sind aus der Gruppe der organischen oder anorganischen Verbindungen von Mangan, Calcium, Eisen, Magnesium, Selen, Kobalt, Nickel und/oder Zink.10. Composition according to one of claims 1 to 9, characterized in that the micronutrients are selected from the group of organic or inorganic compounds of manganese, calcium, iron, magnesium, selenium, cobalt, nickel and / or zinc.
s 11. Verfahren zur Steigerung des Pflanzenwachstums, dadurch gekennzeichnet, daß man ein wäßriges Mittel gemäß Anspruch 1 auf die Blätter der Pflanzen aufbringt.11. Process for increasing plant growth, characterized in that an aqueous agent according to claim 1 is applied to the leaves of the plants.
12. Verwendung von Verbindungen der Formel (I) zur Steigerung der Penetration von Mikronährstoffen in Pflanzen. 12. Use of compounds of formula (I) to increase the penetration of micronutrients in plants.
PCT/EP2000/013265 2000-01-07 2000-12-23 Aqueous means containing micronutrients for plants WO2001051432A1 (en)

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