EP1272034A1 - Aqueous herbicidal agent - Google Patents

Aqueous herbicidal agent

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Publication number
EP1272034A1
EP1272034A1 EP01927862A EP01927862A EP1272034A1 EP 1272034 A1 EP1272034 A1 EP 1272034A1 EP 01927862 A EP01927862 A EP 01927862A EP 01927862 A EP01927862 A EP 01927862A EP 1272034 A1 EP1272034 A1 EP 1272034A1
Authority
EP
European Patent Office
Prior art keywords
compounds
formula
composition according
iodoxynil
saturated
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01927862A
Other languages
German (de)
French (fr)
Inventor
Horst-Werner Wollenweber
Benoit Abribat
Hans De Ruiter
Hans-Georg Mainx
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Cognis Deutschland GmbH and Co KG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis Deutschland GmbH and Co KG filed Critical Cognis Deutschland GmbH and Co KG
Publication of EP1272034A1 publication Critical patent/EP1272034A1/en
Withdrawn legal-status Critical Current

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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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles

Definitions

  • the present invention relates to aqueous herbicidal compositions which contain at least one agrochemical active ingredient from the group iodoxynil and its derivatives, and to certain alkoxylated fatty acid esters, the use of such fatty acid esters to increase the penetration of iodoxynil or its derivatives in plant leaves, and a process for combating undesired plant growth.
  • agrochemical active ingredients are therefore formulated in the form of an aqueous dispersion or emulsion and can then be used without problems, e.g. by spraying onto the plants, the emulsifier also acting as a wetting agent and allowing improved absorption of the active ingredient into the plant. The higher the penetration of the active ingredient, the more effectively and efficiently it can be used.
  • aqueous compositions which contain iodoxynil salts and, as formulation auxiliaries, alkali metal salts of alkyl polyglycol ether phosphate partial esters.
  • EP-0-485 207 discloses aqueous emulsions containing iodoxynil octanoate and heptanoate, which contain polyalkylene oxide-modified silanes or ethoxylated tall oil amides as emulsifiers.
  • aqueous compositions which contain iodoxynil or its derivatives and alkoxylated alcohols determined as emulsifiers enable very high penetration of the herbicide into the plant.
  • the present application therefore relates to aqueous compositions which contain iodoxynil or its derivatives and one or more compounds of the general formula (I)
  • RO- (C2H 4 0) n (C 3 H 6 0) m -R '(I) 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 "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.
  • the agents according to the invention contain iodoxynil and / or its derivatives, preferably iodoxynil alkyl esters or sodium and / or potassium salts of iodoxynil or its sulfates and carbonates. Agents which contain iodoxynil octanoate or heptanoate are particularly preferred.
  • 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 the formula (I) can be prepared by all methods known to the person skilled in the art, for example 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.
  • Compounds of the formula (I) which contain between 1 and 30 moles of ethylene oxide per mole of ester are preferred. It is preferred that, in addition to the ethylene oxide units, between one and 10 propylene oxide groups are 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-C3Q 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, palitoleic, oleic, elaidic, arachic, gadoleic, behenic and erucic acids.
  • 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 produced by the reaction of the full ester and the Partial esters can be obtained with alkoxides.
  • the radical R" is in the formula (I) therefore only for a branched or linear, saturated or unsaturated alkyl radical having 5 to 29 carbon atoms.
  • esters of the formula (I) whose fatty acid component is selected from linear, unbranched C 1 -C 4 -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.
  • alkoxylated 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.
  • compositions contain at least iodoxynil or its derivatives as herbicidal active ingredients, but mixtures with various other active ingredients are also possible.
  • the agents according to the invention can contain the active ingredient both in enriched form, ie they are concentrates with more than 50% by weight to a maximum of 90% by weight of active ingredient. But they can also be in diluted form. Agents which contain between 0.01 and 5% by weight of iodoxynil or its derivatives, based on the weight of the agents, are preferred. Are other agrochemical agents contain so they are present in amounts of 0.01 to 10 wt .-%.
  • the water content of the agents according to the invention is preferably between 10 and 99.9% by weight.
  • the quantitative ratio between the compounds of the formula (I) and the active compounds is preferably between 1: 1 and 1: 100.
  • Particularly preferred agents are those in which the weight ratio between the compounds of the formula (I) and the active compounds is in the range from 1: 10 to 1: 80 and in particular in the range from 1: 2 to 1: 5.
  • the aqueous compositions according to the invention can also contain other customary ingredients and additives.
  • solvents such as ethylene or propylene glycols and Ci-C ⁇ 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 do not contain any further emulsifiers or dispersants.
  • agents are preferred which are free of colloids, such as titanium dioxide and / or free of solvents, in particular of mineral oil-based solvents.
  • compositions according to the invention are stable in storage even at temperatures above 30 ° C. and can be prepared 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 iodoxynil-containing agent according to the above description being applied to the plant leaves in such amounts in any manner known to the person skilled in the art that the plants die.
  • the present invention further relates to the use of compounds of the formula (I) for increasing the penetration of iodoxynil or its derivatives in plant leaves.
  • the emulsifiers were each present in amounts of 0.5% by weight, based on the total agent.
  • the concentration of the sodium salt of iodoxynil was 4.1 mM.
  • 0.1 ⁇ l of the aqueous agent was applied to the first leaves of the deadly cherry. The penetration into the leaves was then measured after 24 hours. The results are shown in Table 2:

Abstract

The invention relates to aqueous agents containing ioxynil or the derivatives thereof and compounds of general formula (I) in which: RO represents an alcohol residue selected from the group of branched or linear, saturated or unsaturated monohydric alcohols with 1 to 6 C atoms or of polyols with 2 to 12 C atoms and 2 to 6 hydroxyl groups; R' represents hydrogen and/or an ester group -CO-R'', in which R'' represents a branched or liner, saturated or unsaturated alkyl residue with 5 to 29 C atoms; n is a number between 1 and 50, and; m is either equal to zero or to a number between 1 and 10. The inventive agents exhibit an increased level of penetration of the active substance into plants.

Description

Wäßriges herbizides Mittel IIAqueous herbicidal composition II
Die vorliegenden Erfindung betrifft wäßrige herbizide Mittel, die mindestens einen agrochemischen Wirkstoff aus der Gruppe lodoxynil und dessen Derivate enthält sowie bestimmte alkoxylierte Fettsäureester, die Verwendung solcher Fettsäureester zur Steigerung der Penetration von lodoxynil bzw. dessen Derivaten in Pflanzenblätter sowie ein Verfahren zur Bekämpfung unerwünschten Pflanzenwachstums.The present invention relates to aqueous herbicidal compositions which contain at least one agrochemical active ingredient from the group iodoxynil and its derivatives, and to certain alkoxylated fatty acid esters, the use of such fatty acid esters to increase the penetration of iodoxynil or its derivatives in plant leaves, and a process for combating undesired plant growth.
Zu Bekämpfung von Unkräuter sind eine Vielzahl von herbiziden Substanzen bekannt, die häufig nur geringe oder keine Wasserlöslichkeit zeigen. Ein wichtiger Vertreter ist das lodoxynil (3,5-Diiodo-4- Hydroxybenzonitril) und dessen Derivate. Bei der Applikation dieser Wirkstoffe kommt es wegen der geringen Wasserlöslichkeit nur zu einer geringen Penetration in die Pflanze und damit zu einer unzureichenden herbiziden Wirkung. Solche agrochemischen Wirkstoffe werden daher in Form einer wäßrigen Dispersion bzw. Emulsion formuliert und können dann problemlos, z.B. durch Aufspritzen auf die Pflanzen verwendet werden, wobei der Emulgator auch als Benetzer fungiert und eine verbesserte Aufnahme des Wirkstoffs in die Pflanze ermöglicht. Je höher die Penetration des Wirkstoffs ist, umso wirksamer und effizienter kann er eingesetzt werden. Es besteht daher generell Bedarf an Formulierungen, die eine möglichst vollständige Penetration des herbiziden Wirkstoffs in die Pflanze ermöglichen. Aus der DE-OS 29 24 403 sind beispielsweise wäßrige Mittel, bekannt, die lodoxynilsalze und als Formulierungshilfsmittel Alkalisalze von Alkylpolyglykoletherphosphat- Partialestem enthalten. Aus der EP-0-485 207 sind lodoxyniloctanoat und- heptanoat enthaltende, wäßrige Emulsionen bekannt, die als Emulgatoren polyalkylenoxidmodifizierte Silane oder ethoxylierte Tallölamide enthalten.A large number of herbicidal substances are known for controlling weeds, which frequently have only little or no water solubility. An important representative is iodoxynil (3,5-diiodo-4-hydroxybenzonitrile) and its derivatives. When these active substances are applied, there is little penetration into the plant due to the low solubility in water and therefore an inadequate herbicidal action. Such agrochemical active ingredients are therefore formulated in the form of an aqueous dispersion or emulsion and can then be used without problems, e.g. by spraying onto the plants, the emulsifier also acting as a wetting agent and allowing improved absorption of the active ingredient into the plant. The higher the penetration of the active ingredient, the more effectively and efficiently it can be used. There is therefore a general need for formulations which enable the herbicidal active ingredient to penetrate into the plant as completely as possible. From DE-OS 29 24 403, for example, aqueous compositions are known which contain iodoxynil salts and, as formulation auxiliaries, alkali metal salts of alkyl polyglycol ether phosphate partial esters. EP-0-485 207 discloses aqueous emulsions containing iodoxynil octanoate and heptanoate, which contain polyalkylene oxide-modified silanes or ethoxylated tall oil amides as emulsifiers.
Überraschenderweise wurde gefunden, daß wäßrige Mittel, die lodoxynil oder dessen Derivate sowie als Emulgatoren bestimmte alkoxylierte Alkohole enthalten eine sehr hohe Penetration des Herbizids in die Pflanze ermöglichen.Surprisingly, it has been found that aqueous compositions which contain iodoxynil or its derivatives and alkoxylated alcohols determined as emulsifiers enable very high penetration of the herbicide into the plant.
Gegenstand der vorliegenden Anmeldung sind daher wäßrige Mittel, die lodoxynil oder dessen Derivate enthalten und eine oder mehrere Verbindungen der allgemeinen Formel (I)The present application therefore relates to aqueous compositions which contain iodoxynil or its derivatives and one or more compounds of the general formula (I)
RO-(C2H40)n(C3H60)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.RO- (C2H 4 0) n (C 3 H 6 0) m -R '(I) 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 "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.
Die erfindungsgemäßen Mittel enthalten lodoxynil und/oder dessen Derivate, vorzugsweise lodoxynilalkylester bzw. Natrium- und/oder Kaliumsalze des lodoxynils oder dessen Sulfate und Carbonate. Besonders bevorzugt sind Mittel, die lodoxyniloctanoat oder -heptanoat enthalten.The agents according to the invention contain iodoxynil and / or its derivatives, preferably iodoxynil alkyl esters or sodium and / or potassium salts of iodoxynil or its sulfates and carbonates. Agents which contain iodoxynil octanoate or heptanoate are particularly preferred.
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 Fettsäurealkylestem 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. Die alkoxylierten Fettsäureester enthalten mindestens 1 Mol Ethylenoxidgruppen pro Mol Ester. Bevorzugt sind Verbindungen der Formel (I), die pro Mol Ester zwischen 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 compounds of the formula (I) can be prepared by all methods known to the person skilled in the art, for example 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. The alkoxylated fatty acid esters contain at least 1 mole of ethylene oxide groups per mole of ester. Compounds of the formula (I) which contain between 1 and 30 moles of ethylene oxide per mole of ester are preferred. It is preferred that, in addition to the ethylene oxide units, between one and 10 propylene oxide groups are 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 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 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-C3Q Fettsäuren, einschließlich technischer Gemische derselben, wie sie durch Fettspaltung aus tierischen und pflanzlichen Fetten und Ölen zugänglich sind, z.B. aus Kokosöl, Palmkemöl, Sojaöl, Sonnenblumenöl, Rüböl, Baumwollsaatöl, Fischöl, Rindertalg und Schweineschmalz; spezielle Beispiele sind Capryl-, Caprin-, Laurin-, Laurolein-, Myristin-, Myristolein-, Palmitin-, Pal itolein-, Öl-, Elaidin-, Arachin-, Gadolein-, 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-C3Q 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, turnip oil, cottonseed oil, fish oil, beef tallow and lard; specific examples are caprylic, capric, lauric, laurolein, myristic, myristoleic, palmitic, palitoleic, oleic, elaidic, arachic, gadoleic, behenic and erucic acids.
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 produced by the reaction of the full ester and the Partial esters can be obtained 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 closed with ester groups of the formula -CO-R ". In these preferred compounds, the radical R" is in the formula (I) therefore only 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 C& bis Cιβ 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 those alkoxylated fatty acid esters of the formula (I) whose fatty acid component is selected from linear, unbranched C 1 -C 4 -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 alkoxylierte 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 alkoxylated 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 als herbizide Wirkstoffe mindestens lodoxynil oder dessen Derivate, es sind aber auch Mischungen mit verschiedenen anderen Wirkstoffen möglich. Die erfindungsgemäßen Mittel können den Wirkstoff sowohl in angereicherter Form enthalten, d.h. es handelt sich um Konzentrate mit mehr als 50 Gew.-% bis maximal 90 Gew.-% Wirkstoff. Sie können aber auch in verdünnter Form vorliegen. Bevorzugt sind Mittel, die zwischen 0,01 und 5 Gew.-% an lodoxynil bzw. dessen Derivate, bezogen auf das Gewicht der Mittel, enthalten. Sind andere agrochemische Wirkstoffe 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.-%. Das Mengenverhältnis zwischen den Verbindungen der Formel (I) und den Wirkstoffen liegt vorzugsweise zwischen 1 : 1 und 1 : 100. Besonders bevorzugt sind solche Mittel, bei denen das Gewichtsverhältnis zwischen den Verbindungen der Formel (I) und den Wirkstoffen im Bereich von 1 : 10 bis 1 : 80 und insbesondere im Bereich von 1 : 2 bis 1 : 5 beträgt.The compositions contain at least iodoxynil or its derivatives as herbicidal active ingredients, but mixtures with various other active ingredients are also possible. The agents according to the invention can contain the active ingredient both in enriched form, ie they are concentrates with more than 50% by weight to a maximum of 90% by weight of active ingredient. But they can also be in diluted form. Agents which contain between 0.01 and 5% by weight of iodoxynil or its derivatives, based on the weight of the agents, are preferred. Are other agrochemical agents contain so they are present in amounts of 0.01 to 10 wt .-%. The water content of the agents according to the invention is preferably between 10 and 99.9% by weight. The quantitative ratio between the compounds of the formula (I) and the active compounds is preferably between 1: 1 and 1: 100. Particularly preferred agents are those in which the weight ratio between the compounds of the formula (I) and the active compounds is in the range from 1: 10 to 1: 80 and in particular in the range from 1: 2 to 1: 5.
Neben lodoxynil bzw. dessen Derivaten und den Verbindungen der Formel (I) können die erfindungsgemäßen wäßrigen Mittel noch weitere übliche Inhaltsstoffe und Additive enthalten. Dazu zählen Lösungsmittel, wie Ethlyen- oder Propylenglykole und Ci-Cε-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. Insbesondere sind solche Mittel bevorzugt, die frei von Kolloiden, wie Titandioxid und/oder frei von Lösungsmitteln, insbesondere von mineralölbasierten Lösungsmitteln sind.In addition to iodoxynil or its derivatives and the compounds of the formula (I), the aqueous compositions according to the invention can also contain other customary ingredients and additives. These include solvents such as ethylene or propylene glycols and Ci-Cε 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 do not contain any further emulsifiers or dispersants. In particular, agents are preferred which are free of colloids, such as titanium dioxide and / or free of solvents, in particular of mineral oil-based solvents.
Die erfindungsgemäßen Mittel sind auch 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 even at temperatures above 30 ° C. and can be prepared 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 Bekämpfung unerwünschter Pflanzen beansprucht, wobei eine wäßriges lodoxynil-haltiges Mittel gemäß der obigen Beschreibung in jeder dem Fachmann bekannten Art auf die Pflanzenblätter in solchen Mengen aufgebracht wird, daß die Pflanzen absterben. Ein weiterer Gegenstand der vorliegenden Erfindungen betrifft die Verwendung von Verbindungen der Formel (I) zur Steigerung der Penetration von lodoxynil bzw. dessen Derivaten in Pflanzenblätter. Furthermore, a method for controlling unwanted plants is claimed, an aqueous iodoxynil-containing agent according to the above description being applied to the plant leaves in such amounts in any manner known to the person skilled in the art that the plants die. The present invention further relates to the use of compounds of the formula (I) for increasing the penetration of iodoxynil or its derivatives in plant leaves.
BeispieleExamples
Es wurden sechs wäßrige lodoxinyl-Na-Salz Emulsionen hergestellt, die entweder frei von Emulgatoren waren oder bekannte Emulgatoren enthielten und diese verglichen mit einem erfindungsgemäßen Mittel, enthaltend als Additiv eine Verbindung der Formel (I) mit RO = Glycerin, R' = COR" mit R" =C16-C18, m= 0, n = 30.Six aqueous iodoxinyl Na salt emulsions were prepared which were either free of emulsifiers or contained known emulsifiers and compared them with an agent according to the invention containing an additive of a compound of the formula (I) with RO = glycerol, R '= COR " with R "= C16-C18, m = 0, n = 30.
Die Emulgatoren waren jeweils in Mengen von 0,5 Gew.-%, bezogen auf das gesamte Mittel, enthalten Die Konzentration des Natriumsalz des lodoxynils betrug 4,1 mM. Jeweils 0,1 μl der wäßrigen Mittel wurden auf die ersten Blätter der Tollkirsche aufgebracht.. Anschließend wurde die Penetration nach 24 Stunden in die Blätter gemessen. Die Ergebnisse sind in Tabelle 2 wiedergegeben:The emulsifiers were each present in amounts of 0.5% by weight, based on the total agent. The concentration of the sodium salt of iodoxynil was 4.1 mM. In each case 0.1 μl of the aqueous agent was applied to the first leaves of the deadly cherry. The penetration into the leaves was then measured after 24 hours. The results are shown in Table 2:
Tabelle 1 :Table 1 :
Versuch EmulgatorTry emulsifier
(1) -(1) -
(2) C_-ι.-Alkyl(oligo)glucosid(2) C 1-8 alkyl (oligo) glucoside
(3) Cδ-io-Fettsäuremethylester + 3 EO(3) Cδ-io fatty acid methyl ester + 3 EO
(4) Cδ-iö-Fettsäuremethylester + 6 EO(4) Cδ-iö fatty acid methyl ester + 6 EO
(5) Nonylphenol + 10 EO(5) Nonylphenol + 10 EO
(6) erfindungesgemäßes Triglycerid(6) Triglyceride according to the invention
Tabelle 2:Table 2:
Versuch Penetration nach 24 h in %Trial penetration after 24 h in%
(1) 0(1) 0
(2) 2(2) 2
(3) 22(3) 22
(4) 56(4) 56
(5) 42(5) 42
(6) 82(6) 82
Die Ergebnisse zeigen die Steigerung der Penetration des lodoxynils durch Zusatz der erfindungsgemäßen Mittel. The results show the increase in the penetration of the iodoxynil by adding the agents according to the invention.

Claims

Patentansprüche claims
1. Herbizides Mittel, enthaltend Wasser und lodoxynil und/oder dessen Derivate, dadurch gekennzeichnet, daß es weiterhin mindestens eine oder mehrere Verbindungen der allgemeinen1. Herbicidal agent containing water and iodoxynil and / or its derivatives, characterized in that it further comprises at least one or more compounds of the general
Formel (I) enthält,Contains 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.
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. Composition 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 5 Gew.-% lodoxynil bzw. dessen Derivate enthalten.9. Composition according to one of claims 1 to 8, characterized in that they contain between 0.01 and 5 wt .-% iodoxynil or its derivatives.
10. Mittel nach einem der Ansprüche 1 bis 9, dadurch gekennzeichnet, daß es lodoxynilalkylester, vorzugsweise iodoxyniloctanoat oder- heptanoat enthält.10. Composition according to one of claims 1 to 9, characterized in that it contains iodoxynil alkyl esters, preferably iodoxynil octanoate or heptanoate.
11. Mittel nach einem der Ansprüche 1 bis 10, dadurch gekennzeichnet, daß Natrium- und/oder Kaliumsalze des lodoxynils enthält.11. Agent according to one of claims 1 to 10, characterized in that sodium and / or potassium salts of iodoxynil contains.
12. Mittel nach einem der Ansprüche 1 bis 11, dadurch gekennzeichnet, daß es frei von kolloidem Material ist.12. Composition according to one of claims 1 to 11, characterized in that it is free of colloidal material.
13. Verfahren zur Bekämpfung von unerwünschten Pflanzen, dadurch gekennzeichnet, daß man eine wäßriges Mittel gemäß Anspruch 1 auf die Blätter der unerwünschten Pflanze in solchen Mengen aufbringt, daß die Pflanze abstirbt.13. A method for controlling unwanted plants, characterized in that an aqueous composition according to claim 1 is applied to the leaves of the unwanted plant in such amounts that the plant dies.
14. Verwendung von Verbindungen der Formel (I) zur Steigerung der Penetration von lodoxynil bzw. dessen Derivaten in Pflanzenblätter. 14. Use of compounds of formula (I) to increase the penetration of iodoxynil or its derivatives in plant leaves.
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EP2861065B1 (en) * 2012-06-18 2017-03-15 Basf Se Agroformulations containing a lactone based alkoxylate
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