EP2278877A2 - Suspensions concentrées contenant de la cyclodextrine, leur procédé de préapartion et leur utilisation - Google Patents

Suspensions concentrées contenant de la cyclodextrine, leur procédé de préapartion et leur utilisation

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Publication number
EP2278877A2
EP2278877A2 EP09734510A EP09734510A EP2278877A2 EP 2278877 A2 EP2278877 A2 EP 2278877A2 EP 09734510 A EP09734510 A EP 09734510A EP 09734510 A EP09734510 A EP 09734510A EP 2278877 A2 EP2278877 A2 EP 2278877A2
Authority
EP
European Patent Office
Prior art keywords
cyclodextrin
suspension concentrate
alcohol
herbicides
fungicides
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Withdrawn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
EP09734510A
Other languages
German (de)
English (en)
Inventor
Rainer Berghaus
Matthias Bratz
Rainer Dyllick-Brenzinger
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 SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to EP09734510A priority Critical patent/EP2278877A2/fr
Publication of EP2278877A2 publication Critical patent/EP2278877A2/fr
Withdrawn legal-status Critical Current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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels

Definitions

  • the invention relates to suspension concentrates with cyclodextrin, processes for their preparation and the use of the suspension concentrates for the treatment of plants and their habitat and corresponding methods, and also spray mixtures containing such a suspension concentrate.
  • Plant protection products may contain, in addition to or directly to the pests acting substance or substances (hereinafter referred to as crop protection active) various types of accompanying and auxiliary substances that enhance the desired effect in various ways, simplify the handling, increase the shelf life or otherwise improve the properties of the product (in literature then mostly “additives”, “adjuvants”, “accelerators”, “boosters” or “enhancers” called).
  • pesticides are dissolved, emulsified or dispersed in an aqueous medium to obtain an aqueous spray mixture, which is then applied to the plants or their habitat by the so-called spraying method.
  • the concomitant and auxiliary substances must be selected accordingly to give a suitable spray mixture.
  • effect-promoting adjuvants is generally based on their interfacial activity against the hydrophobic plant surface, which improves the contact of the spray mixture with the plant surface.
  • wetting agents spreaders, and permeabilizers ("penetrators"), which naturally overlap.
  • permeabilizers percutaneous permeabilizers
  • adjuvant which does not take into account physical details, is used to denote enhancers of agrochemical active substances, in particular crop protection active ingredients.
  • Nonionic, hydrophobic alkoxylates are known as suitable adjuvants for various crop protection agents, especially fungicides.
  • alkoxylates are used primarily in liquid formulations, which include solutions, emulsions, suspensions, suspoemulsions and other liquid formulation types. However, this is in many cases fraught with problems.
  • An object of the present invention are therefore suspension concentrates of a crop protection agent comprising alcohol alkoxylate and cyclodextrin.
  • suspension concentrate agents which have finely divided solid particles of an active ingredient as a suspension (dispersion) in a fluid medium
  • the active substance is accordingly only slightly soluble or virtually insoluble in the fluid medium (generally less than 2000 ppm ).
  • the suspension concentrates according to the invention comprise in addition to one or more active ingredients basically two components:
  • a cyclodextrin component consisting of one or more cyclodextrins.
  • the suspension concentrates according to the invention are usually pesticides, which is why the following also refers to pesticides or agents according to the invention.
  • the alcohol alkoxylate to be used is low melting or liquid.
  • liquid refers to the liquid state of matter at normal pressure and a temperature in the range of 20 to 30 0 C.
  • a low-melting alcohol alkoxylate generally has a melting point of less than 40 0 C, in particular less than 30 ° C.
  • the alcohol alkoxylate to be used is oily.
  • the term "oily” refers to a viscous, tacky greasy physical consistency; Chemically, the substance may be lipophilic, hydrophilic or amphiphilic. As a rule, the alcohol alkoxylates are amphiphilic.
  • the alcohol alkoxylates according to the invention basically comprise a hydrophobic or lipophilic part and one or more polymeric alkoxylate parts (polyalkoxylate or macrogol parts), the or each individual alkoxylate part being linked to the hydrophobic or lipophilic part via an ether bond.
  • polymer means at least two, in particular at least three and more particularly from 3 to 1000, low molecular weight units composed of one another, all of which may be the same, so as to give a monotone polymer, or at least two different types of alkylene oxide.
  • each case a plurality of alkylene oxide units of one type as a block, so that the structural elements of the polymer are at least two different alkylene oxide blocks, each of which consists of a monotone series of identical alkylene oxide units (block polymer If such block alkoxylates are used, it is preferred that the alkylene oxide part be composed of 2 or 3 and in particular of 2 blocks If the alkoxylate part comprises different blocks, the parts closest to the hydrophobic or lipophilic part will be as "proximal", the more distant than distal "and the terminal referred to as" terminal ".
  • alkoxylate in particular the alkylene oxides having 2 to 16 carbon atoms, in particular ethylene oxide (EO), propylene oxide (PO), butylene oxide (BO), pentylene oxide (PeO), hexylene oxide (HO) and decylene oxide (DeO).
  • EO ethylene oxide
  • PO propylene oxide
  • BO butylene oxide
  • PeO pentylene oxide
  • HO hexylene oxide
  • DeO decylene oxide
  • alcohol alkoxylates can be found among the alkoxylated fatty alcohols, alkoxylated alkylphenols and alkoxylated di- and tristyrylphenols, where the alkylphenyls are preferably alkylated several times, in particular twice or three times.
  • the alcohol alkoxylates may also be end group-modified, i. the terminal OH group of the alkoxylate part is modified, for example etherified or esterified.
  • Suitable end-group-modified alcohol alkoxylates include, in particular, alkylated, alkenylated or arylated alcohol alkoxylates, preferably those having a methyl or tert-butyl group or a phenyl group, or polyalkoxylate esters, e.g. Mono- or diphosphate esters or sulfate esters, and their salts, for example the alkali metal or alkaline earth metal salts.
  • Such end group modification can be carried out, for example, with dialkyl sulfate, ⁇ -dialkyl halide or phenyl halide.
  • WO 03/090531, WO 2005/015998, WO 00/35278, WO 99/03345 and WO 2005/084435 describe suitable alcohol alkoxylates.
  • the description of these alcohol alkoxylates in these documents is hereby incorporated by reference. with which the alcohol alkoxylates disclosed therein and also their preparation are part of the present disclosure.
  • alcohol alkoxylates are among alcohol alkoxylates according to the formula (I)
  • R 1 is an aliphatic hydrocarbon radical having 1 to 100 carbon atoms
  • R 2 is hydrogen, an organic radical or an inorganic acid group
  • n, p are independently an integer from 2 to 16, preferably from 2, 3, 4 or 5;
  • x, y, z independently represent a number from 0 to 1000;
  • x + y + z corresponds to a value of 2 to 1000.
  • the aliphatic hydrocarbon radical is generally hydrophobic or lipophilic, as a result of which the alcohol alkoxylates obtain their oil-like properties.
  • R 1 is a branched or linear hydrocarbon radical having 1 to 30 and preferably 5 to 24 carbon atoms, which may be saturated (in particular Ci_ 3 o-alkyl) or unsaturated (in particular C 3 _ 3 o-alkenyl).
  • the organic radical (R 2 ) typically contributes less than 10% and preferably less than 5% to the molecular weight of the alcohol alkoxylate of the formula (I) and is preferably hydrogen, alkyl, preferably C 1-10 -alkyl, more preferably methyl or tert-butyl, alkenyl, preferably C 2-io-alkenyl, acyl, especially acetyl, propionyl, benzoyl or butylene ryl, aryl, particularly phenyl, or an inorganic acid group, in particular phosphate, diphosphate or sulfate.
  • a plurality of alkylene oxide units may be arranged arbitrarily.
  • the structural unit - (C m H 2m O) ⁇ - (C n H 2n O) y- (CpH 2p O) z - can thus be a random copolymer, a gradient copolymer, an alternating or a block copolymer of alkylene oxide blocks (C m H 2m O) x , alkylene oxide blocks - (C n H 2n O) y and / or alkylene oxide blocks - (C p H 2p O) z - be.
  • the arrangement is in blocks.
  • the alcohol alkoxylates to be used according to the invention are ethoxylated or have at least one ethylene oxide block.
  • ethylene oxide blocks are combined in particular with propylene oxide, butylene oxide or pentylene oxide blocks.
  • the degree of ethoxylation (value of x) is generally 1 to 20, preferably 2 to 15 and in particular 4 to 10
  • the degree of propoxylation (value of y) is generally 1 to 20, preferably 1 to 8 and in particular 2 to 5.
  • Theylonalkoxyl istsgrad, ie the sum of EO and PO units is usually 2 to 40, preferably 3 to 25 and especially 5 to 15.
  • the ratio of EO to BO (x to y) is preferably 1.1: 1 to 25: 1 and in particular 3: 1 to 10: 1.
  • the degree of ethoxylation (value of x) is generally 1 to 50, preferably 3 to 40 and in particular 5 to 30, the degree of butoxylation (value of y) is generally 0.5 to 30, preferably 1 to 20 and in particular 1, 5 to 15.
  • the Automatalkoxyl istsgrad, ie the sum of EO and BO units is usually 2 to 70, preferably 4.5 to 29 and especially 6.5 to 17.
  • the ratio of EO to PeO (x to y) is preferably 2: 1 to 25: 1 and in particular 4: 1 to 15: 1.
  • the degree of ethoxylation (value of x) is generally 1 to 50, preferably 4 to 25 and in particular 6 to 15, the degree of pentoxylation (value of y) is generally 0.5 to 20, preferably 0.5 to 4 and in particular 0.5 to 2.
  • Theylonalkoxyl michsgrad, ie the sum of EO and PeO units is usually 1.5 to 70, preferably 4.5 to 29 and especially 6.5 to 17.
  • these are EO-type alcohol alkoxylates in which the EO block is bound distally and another polyalkoxylate block is interposed between it and the aliphatic hydrocarbon residue.
  • the degree of ethoxylation (value of y) is generally 1 to 20, preferably 2 to 15 and in particular 4 to 10
  • the degree of propoxylation (value of x) is generally 0.5 to 10, preferably 0.5 to 6 and in particular 1 to 4.
  • Theylonalkoxyl istsgrad, ie the sum of EO and PO units is usually 1, 5 to 30, preferably 2.5 to 21 and especially 5 to 14.
  • the degree of butoxylation (value of x) is generally 0.5 to 30, preferably 1 to 20 and in particular 1.5 to 15, the degree of ethoxylation (value of y) is generally 1 to 50, preferably 3 to 40 and especially 5 to 30.
  • the Strategicalkoxyl istsgrad, ie the sum of EO and BO units is usually 2 to 70, preferably 4.5 to 29 and especially 6.5 to 17.
  • PeO-EO block alkoxylates in which the ratio of PeO to EO (x to y) is from 1:50 to 1: 3 and in particular from 1:25 to 1: 5 are preferred.
  • the degree of pentoxylation (value of x) is generally 0.5 to 20, preferably 0.5 to 4 and in particular 0.5 to 2
  • the degree of ethoxylation (value of y) is generally 3 to 50, preferably 4 to 25 and especially 5 to 15.
  • the Automatalkoxyltechniksgrad, ie the sum of EO and PeO units is generally 3.5 to 70, preferably 4.5 to 45 and in particular 5.5 to 17.
  • the alcohol alkoxylates of the formula (I) are not end-group-modified, ie R 2 is hydrogen.
  • the alcohol portion of the alcohol alkoxylates is based on alcohols or mixtures of alcohols known per se having from 5 to 30, preferably from 8 to 20 and in particular from 9 to 15 carbon atoms.
  • fatty alcohols having about 8 to 20 carbon atoms may be mentioned here.
  • Many of these fatty alcohols are known to be used for the preparation of nonionic and anionic surfactants, for which purpose the alcohols are subjected to a corresponding functionalization, for example by alkoxylation or glycosidation.
  • the alcohol part can be straight-chain, branched or cyclic. If it is linear, alcohols having 14 to 20, for example, 16 to 18 carbon atoms are to be mentioned in particular. If it is branched, according to a particular embodiment, the main chain of the alcohol part generally has 1 to 4 branches, it also being possible to use alcohols having a higher or lower degree of branching in a mixture with other alcohol alkoxylates, as long as the average number of branches of the mixture is in the specified range.
  • the alcohol part can be saturated or unsaturated. If it is unsaturated, it has, according to a particular embodiment, a double bond.
  • the branches of the alcohol moiety independently of one another have in each case 1 to 10, preferably 1 to 6 and in particular 1 to 4, carbon atoms.
  • Particular branches are methyl, ethyl, n-propyl or isopropyl groups.
  • Suitable alcohols, and especially fatty alcohols are derived from both native sources, e.g. by recovery and, if desired, by hydrolysis, transesterification and / or hydrogenation of glycerides and fatty acids, as well as by a synthetic route, for. B. by construction of educts with a lower number of carbon atoms available. So you get z.
  • SHOP process Shell Higher Olefinic Process
  • the functionalization of the olefins to the corresponding alcohols takes place z. B. by hydroformylation and hydrogenation.
  • the alkoxylation results from the reaction with suitable alkylene oxides.
  • suitable alkylene oxides Depending on the chosen for the reaction amounts of alkylene oxide (s) and the reaction conditions, the respective degree of alkoxylation results. This is usually a statistical average as the number of alkylene oxide units of the alcohol alkoxylates resulting from the reaction varies.
  • the degree of alkoxylation i. the average chain length of the polyether chains according to the invention to be used alcohol alkoxylates can by the molar ratio of
  • Alcohol to Alkylenoxid bestimmmt be.
  • reaction of the alcohols or alcohol mixtures with the alkylene oxide (s) is carried out by customary methods known to the person skilled in the art and in apparatuses customary for this purpose.
  • the alkoxylation reaction can be catalyzed by strong bases such as alkali hydroxides and alkaline earth hydroxides, Brönsted acids or Lewis acids such as AICI 3 , BF 3, etc.
  • strong bases such as alkali hydroxides and alkaline earth hydroxides, Brönsted acids or Lewis acids such as AICI 3 , BF 3, etc.
  • catalysts such as hydrotalcite or DMC can be used.
  • the alkoxylation is preferably carried out at temperatures in the range of about 80 to 250 0 C, preferably about 100 to 220 0 C.
  • the pressure is preferably between ambient pressure and 600 bar.
  • the alkylene oxide may be an inert gas admixture, e.g. From about 5 to 60%.
  • the alcohol alkoxylates to be used according to the invention are based on primary, ⁇ -branched alcohols of the formula (II)
  • R 3 , R 4 independently of one another represent hydrogen or C 1 -C 26 -alkyl.
  • R 3 and R 4 independently of one another are C 1 -C 6 -alkyl and in particular C 2 -C 4 -alkyl.
  • alcohol alkoxylates are used whose alcohol part is 2-propylheptanol.
  • These include in particular alcohol alkoxylates of the formula (I) in which R 1 is a 2-propylheptyl radical, ie R 3 and R 4 in formula (II) are each n-propyl.
  • Such alcohols are also referred to as Guerbet alcohols. These can be obtained, for example, by dimerization of corresponding primary alcohols (eg R 3 ' 4 - CH 2 CH 2 OH) at elevated temperature, for example 180 to 300 ° C., in the presence of an alkaline condensing agent such as potassium hydroxide. According to a further particular embodiment, alcohol alkoxylates are used whose alcohol part is a C 3 -oxo-alcohol.
  • Ci 3 -oxo 2 hydrocarbons are obtainable by hydroformylation and subsequent hydrogenation of unsaturated Ci, in particular by hydrogenation of hydroformylated trimeric butene or by hydrogenation of hydroformylated dimeric hexene is.
  • Ci 3 -oxo alcohol usually an alcohol mixture whose main component of at least one branched C 3 alcohol (isotridecanol) is formed.
  • Ci3-alcohols include, in particular tetramethylnonanols, for example, 2,4,6,8-tetramethyl 1-nonanol or 3,4,6,8-tetramethyl-1-nonanol and also ethyldimethylnonanols such as 5-ethyl-4,7-dimethyl-1-nonanol.
  • Suitable C 13 -alcohol mixtures are generally obtainable by hydrogenation of hydroformylated trimerbutene. In particular, you can
  • the buttrimerization preceding hydrogenation may be by homogeneous or heterogeneous catalysis.
  • Ci 3 is in one or more separation steps, first - alcohol mixtures by hydroformylation and hydrogenation of suitable C 2 olefin fraction isolated (step 2).
  • Suitable separation devices are the usual apparatuses known to the person skilled in the art.
  • Ci3-alcohol mixtures are obtainable by that
  • the inventive Ci3 alcohol mixture for use as component (a ⁇ ) can be obtained pure by conventional, known in the art purification process, in particular by fractional distillation.
  • Ci invention alcohol mixtures generally have an average degree of branching of from 1 to 4., preferably from 2.0 to 2.5, and particularly 2.1 to 2.3 (based on trimeric butene) or 1, 3 to 1 , 8 and in particular 1, 4 to 1, 6 (based on dimer hexene).
  • the degree of branching is defined as the number of methyl groups in a molecule of the alcohol minus 1.
  • the mean degree of branching is the statistical mean of the degrees of branching of the molecules of a sample.
  • the average number of methyl groups in the molecules of a sample can easily be determined by 1 H NMR spectroscopy. For this, the signal area corresponding to the methyl protons in the 1 H-NMR spectrum of a sample is divided by 3 and related to the divided by two signal surface of the methylene protons in the CH 2 -OH group.
  • alcohol alkoxylates are used whose alcohol part is a Cio-oxo-alcohol.
  • the term "C 10 -oxoalcohol” is analogous to the already explained term “C 13 -oxoalcohol” for C 10 -alkoxy mixtures whose main component is formed from at least one branched C 10 -alcohol (isodecanol).
  • Cio-alcohol mixtures are obtained by hydrogenation of hydroformylated Trimerpropen.
  • the alcohol alkoxylates to be used according to the invention generally have a relatively low contact angle.
  • Particularly preferred are alkoxylates whose contact angle is less than 120 ° and preferably less than 100 °, when it is determined using a 2 wt .-% alkoxylate-containing aqueous solution on a paraffin surface in a conventional manner.
  • the surface-active properties of the alcohol alkoxylates depend on one aspect of the nature and distribution of the alkoxylate moiety.
  • the surface tension, which can be determined by the pendant drop method, of the alcohol alkoxylates to be used according to the invention is preferably in a range from 25 to 70 mN / m and in particular from 28 to 50 mN / m for a solution containing 0.1% by weight of alcohol alkoxylate, in a range of 25 up to 70 mN / m and in particular 28 to 45 mN / m for a solution containing 0.5% by weight of alcohol alkoxylate.
  • Alkoxylates preferably to be used according to the invention therefore qualify as amphiphilic substances.
  • Typical commercial products of the formula (I) are familiar to the person skilled in the art. They are z.
  • BASF SE under the common brand name of "Lutensole” offered, which differs depending on the basic alcohol Lutensole series A, AO, AT, ON, AP, FA, TO, XP, XL and XA
  • Lutensol AO 8 is a C13-15 oxo-alcohol with eight EO units. Also marketed under the brand name Plurafac mecanic mecanic, z.
  • polyalkoxylates are products of the company Akzo, z.
  • the "ethylan” series based on linear or branched alcohols.
  • "Ethylan SN 120” is a C 0 -i 2 alcohol with ten EO units
  • “Ethylan 4 S” is a C 2- 14 alcohol with four EO units.
  • alcohol alkoxylates according to the invention are castor oil ethoxylates (castor oil EO ⁇ ), z.
  • castor oil EO ⁇ castor oil ethoxylates
  • z z.
  • Alcohol alkoxylates according to the invention also include so-called “narrow range” products
  • the term “narrow rank” refers here to a narrower distribution of the number of EO units. These include z.
  • alcohol alkoxylates of the formula (I) which have at least one terminal block of alkylene oxide having more than 2 carbon atoms (in particular a PO, BO or PEO block).
  • these include the EO-PO, EO-BO and EO-PeO block alkoxylates disclosed herein, each with proximal EO block.
  • the proportion of alcohol lalkoxylat at least 1 wt .-%, preferably at least 5 wt .-% and in particular at least 10 wt .-%, based on the total weight of the composition.
  • the agent contains at most 50% by weight, preferably at most 40% by weight and in particular at most 30% by weight.
  • Alcohol alkoxylate is preferably at most 50% by weight, preferably at most 40% by weight and in particular at most 30% by weight.
  • cyclodextrins can be generally used as the cyclodextrin component (b).
  • cyclodextrin here stands for cyclic oligosaccharides of ⁇ -1, 4-glycosidically linked Gukoemolekülen obtainable by enzymatic degradation of starch. Depending on the number of glucose molecules building up, they are given a Greek letter as a prefix. Of particular importance are ⁇ -, ⁇ -, ⁇ - and ⁇ -cyclodextrins with 6, 7, 8 and 9 glucose molecules, respectively.
  • the cyclodextrins of the invention also include modified cyclodextrins.
  • Modified cyclodextrins are particularly obtainable by modifying one or more of the primary and / or secondary hydroxyl groups. For example, it is possible to alkylate or hydroxyalkylate the hydroxyl groups (ie alkylated or hydroxyalkylated cyclodextrins) to give -OR- and -CH 2 OR- groups, respectively.
  • R is alkyl, preferably C 1 -C 4 -alkyl, in particular methyl, ethyl or propyl; Hydroxyalkyl, preferably hydroxy-C 1 -C 4 -alkyl, especially hydroxymethyl, hydroxyethyl (1-hydroxyethyl or 2-hydroxyethyl), or hydroxypropyl (1-hydroxypropyl, 2-hydroxypropyl or 3-hydroxypropyl); or - [alkylene-O-] n -H, preferably - [methylene-O-] n -H, in particular - [ethylene-O-] n -H, or - [propylene-O-] n -H ( for example, - [1, 1-propylene-O-] n -H, - [1, 2-propylene-O-] n -H or - [1, 3-propylene-O-] n -H), wherein n is larger is 1 and preferably less than 5 stands.
  • cyclodextrins are generally known to the person skilled in the art and can in part also be purchased. Worth to mention here are, for example, the cyclodextrins of Wacker Chemie AG, Germany, marketed under the trade names CAVAMAX® and CAVASOL®.
  • Cyclodextrins have a cavity with which they can trap compounds. This property of cyclodextrins seems to be of importance for the use of the cyclodextrins in the suspension concentrates according to the invention. In this sense, the size of the cavity affects the ability of a cyclodextrin to form an inclusion compound with a particular compound. According to the invention, it has been found that ⁇ -, ⁇ -, and ⁇ -cyclodextrins and especially ⁇ - and ⁇ -cyclodextrins are to be preferred.
  • a natural or modified cyclodextrin is less important according to the invention.
  • the crop protection agent contains at least 0.5 wt .-%, preferably at least 5 wt .-% and in particular at least 10, 15 or wt .-% cyclodextrin.
  • the crop protection agent contains at most 50 wt .-%, preferably at most 45 wt .-% and in particular at most 40 wt .-% cyclodextrin.
  • the suspension concentrates according to the invention contain relatively high amounts of alcohol alkoxylate. Based on the amount of alcohol alkoxylate, it is preferred that the weight ratio of cyclodextrin to alcohol alkoxylate is at least 0.5: 1, preferably at least 1: 1 and more preferably at least 2: 1. there the proportion of alcohol alkoxylate may also be greater than the proportion of cyclodextrin, but preferably at most up to a weight ratio of 5: 1, 4: 1 or 3: 1.
  • suspension concentrates according to the invention in addition to the components a) and b) comprise as component c) further excipient.
  • component (c) can serve many purposes. In general, therefore, component (c) consists of a combination of several substances with different functions and properties. The choice of suitable auxiliaries is carried out according to the requirements usually by the person skilled in the art.
  • surface-active adjuvant refers to surfactants (hereinafter also referred to as surfactants) such as dispersants, emulsifiers or wetting agents.
  • the type of surface-active auxiliary to be selected is not particularly critical according to the invention, that is, it can be selected from known surface-active auxiliaries, in particular dispersants, emulsifiers and wetting agents.
  • surface-active auxiliaries in particular dispersants, emulsifiers and wetting agents.
  • the alcohol alkoxylates are already among the surface-active auxiliaries, which is why this has to be taken into account with regard to the type and amount of further surface-active auxiliary.
  • Dispersants are surface-active auxiliaries which bind primarily to the surface of the active substance particles via ionic and / or hydrophobic interaction and stabilize the particles in the fluid phase.
  • Wetting agents are surface-active adjuvants that primarily reduce the surface tension between the fluid phase and the solid particles dispersed in the fluid phase, thereby stabilizing the particles in the fluid phase.
  • Wetting agents can be selected by means of physical measurements of the contact angle. Particularly suitable wetting agents have a contact angle of less than 90 °, in particular less than 60 ° (at 24 ° C / 1013 mbar of a 1 M aqueous solution of wetting agent according to DIN 53914 using the Wilhelm method or according to the extended Washburn method under Use of active ingredient powder determined).
  • Nional surfactants include in particular:
  • non-polymeric anionic surfactants having a SO 3 "or PO 3 2" group zBc1 C8-C22 alkyl sulfonates such as lauryl sulfonate and Isotridecylsulfonat; c.2 C 8 -C 22 alkyl sulfates such as lauryl sulfate, isotridecyl sulfate, cetyl sulfate and
  • stearyl c.3 aryl and C 1 -C 6 -alkylarylsulfonates such as naphthalenesulfonate, mono-, di- and
  • Tri-d-C 16 -alkyl naphthylsulfonates such as dibutylnaphthylsulfonates, dodecyldiphenyl ether sulfonates, mono-, di- and tri-d-C 16 -alkylphenylsulfonates such as
  • Polymeric anionic surfactants having an SO 3 " or PO 3 2" group for example c9 condensates of arylsulfonic acid with formaldehyde and optionally with urea.
  • Non-polymeric anionic surfactants having at least one carboxylate group, eg c10 fatty acids such as stearates and c.1 1 NC 6 -C 22 acylglutamates.
  • Polymeric anionic surfactants having at least one carboxylate group e.g. c.12 anionic graft copolymers grafted onto a polymer backbone
  • Polyethylene oxide units comprising PEO and carboxylate groups attached to the polymeric backbone, c.13 anionic copolymers containing in polymerized form (i) monoethylenically unsaturated C 3 -C 5 carboxylic acid monomers, and optionally (ii) hydrophobic monomers having a water solubility of not more than 60 g / l at
  • the sodium, potassium, calcium and ammonium salts of the anionic surfactants are preferred.
  • From the group c.3 are mono- or di-C 4 -C 8 alkylnaphthalenesulfonic acid and mono- di-C 4 -C 6 -alkylbenzenesulfonic acid and their alkali metal salts, such as the sodium or potassium salt, and the alkaline earth metal salts, in particular the Preferred are calcium salts thereof.
  • alkali metal salts such as the sodium or potassium salt
  • alkaline earth metal salts in particular the Preferred are calcium salts thereof.
  • a particularly suitable example is Morwet® EFW (Akzo Nobel).
  • From the group c.8 are the alkali metal salts of di (C 6 -C 2 alkyl) sulfosuccinates, where C6-Ci 2 alkyl stands for a straight or branched alkyl group having 6 to 12 carbon atoms, for example n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, 2-hexyl, 2-heptyl, 2-octyl, 2-nonyl and 2-ethylhexyl.
  • C6-Ci 2 alkyl stands for a straight or branched alkyl group having 6 to 12 carbon atoms, for example n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-dodecyl, 2-hexyl, 2-hepty
  • an alkali metal dioctylsulfosuccinate is used, wherein the octyl moiety may be linear or branched and wherein the alkali metal is selected from sodium and potassium.
  • a particularly preferred example is Aerosol® OTB (Cytec).
  • the arylsulfonic acids may be, for example, phenolsulfonic acids and naphthalenesulfonic acids which are unsubstituted or substituted by one or more, eg 1, 2, 3 or 4 C 1 -C 2 0 alkyl groups.
  • the surfactant c.9 is an alkali metal salt or alkaline earth metal salt of a reaction product (condensate) of naphthalenesulfonic acid and formaldehyde; a particularly prized example is Morwet® D425 (Akzo Nobel).
  • Preferred graft copolymers from the group c.12 contain, in polymerized form, (i) monoethylenically unsaturated C 3 -C 5 -carboxylic acid monomers, such as acrylic acid, methacrylic acid and maleic acid, (ii) polyethylene oxide groups which are bonded to the polymer backbone via either ester bonds or ether bonds, and optionally (iii) hydrophobic monomers having a water solubility of not more than 60 g / l at 20 0 C and 1013 mbar, for example, dC methacrylates 6 alkyl esters of C 3 -C 5 monoethylenically unsaturated carboxylic acid monomers such as Ci-C ⁇ alkyl acrylates and, vinylaromati - cal monomers such as styrene and C 2 -C 2 -monolefins such as ethene, propene, 1-butene, isobutene, hexene,
  • Preferred polymeric surfactants of group c.13 are those containing in polymerized form (i) at least one monoethylenically unsaturated C 3 -C 5 carboxylic acid monomer, and (ii) at least one hydrophobic monomer as defined above.
  • Suitable monoethylenically unsaturated C 3 -C 5 -carboxylic acid monomers and suitable hydrophobic be monomers are those mentioned in group c.13.
  • Preferred monoethylenically unsaturated C 3 -C 5 carboxylic acid monomers include acrylic acid, methacrylic acid and maleic acid.
  • Preferred hydrophobic monomers are monoolefins 2 select from vinylaromatic monomers such as styrene monomers and C 2 -C.
  • the surfactants c.13 in polymerized form contain (i) at least one mnoethylenically unsaturated C 3 -C 5 carboxylic acid monomer, especially acrylic acid or methacrylic acid, and (ii) at least one hydrophobic monomer selected from styrenic monomers and C 2 -C 2 -monolefins.
  • the weight ratio of acid monomer to hydrophobic monomer is preferably in the range of 10: 1 to 1: 3; preferably from 5: 1 to 1: 2.
  • a particularly suitable example of a surfactant is c.13 Atlox Metasperse 500L ® (Uniqema).
  • Nonionic surfactants include, in particular, c.14 polyethyleneglycol C 1 -C 22 -alkyl ethers, polyethylene glycol / polypropylene glycol d-C 22 -alkyl ethers, in particular polyethoxylates and polyethoxylate-co-propoxylates of linear or branched C 8 -C 2 0-alkanols, more preferably polyethoxylated C 8 -C 22 fatty alcohols and polyethoxylated C 8 -C 22 oxo alcohols, such as polyethoxylated lauryl alcohol, polyethoxylated isotridecanol, polyethoxylated cetyl alcohol, polyethoxylated stearyl alcohol, polyethoxylate-co-propoxylates of lauryl alcohol, poly-ethoxylate-co-propoxylates of Cetyl alcohol, poly-ethoxylate-co-propoxylates of isotridecyl alcohol, poly-e
  • alkylpolyglucosides c.19 polyethoxylates and poly-ethoxylate-co-propoxylates of C 6 -C 22 fatty amines; c.20 polyethoxylates and poly-ethoxylate-co-propoxylates of C 6 -C 22 -fatty acids and polyethoxylates and poly-ethoxylate-co-propoxylates of hydroxyl C 6 -C 22 -fatty acids; c.21 Polyethoxylates of partial esters of polyols with C 6 -C 22 -alkanoic acids, in particular polyethoxylates of mono- and diesters of glycerol and polyethoxylates of mono-, di- and triesters of sorbitan, such as polyethoxylates of glycerol nostearate, polyethoxylates of sorbitan monooleate, polyethoxylates of sorbitan monostearate and polyethoxylates of
  • polyethylene glycol, polyethoxylates and polyethoxylated refer to polyether radicals derived from ethylene oxide.
  • polyethoxylate-co-propoxylate refers to a polyether radical derived from a mixture of ethylene oxide and propylene oxide.
  • Polyethoxylates therefore have repeat units of the formula [CH 2 CH 2 O]
  • polyethoxylate-co-propoxylates have repeat units of the formulas [CH 2 CH 2 O] and [CH (CH 3 ) CH 2 O].
  • the surfactants c.14, c.15 and c.18 to c.24 may belong to the group of non-polymeric surfactants or the group of polymeric surfactants, depending on the number of alkylene oxide repeating units. In the surfactants of these groups, the number of such repeating units generally ranges from 2 to 200, especially from 3 to 100, especially from 3 to 50.
  • the surfactants of groups c.17 and c.18 belong to non-polymeric surfactants, while the surfactants of groups c.25 and c.26 are usually polymeric surfactants.
  • surfactants c.14 From the group of surfactants c.14, polyethoxylates and poly (ethoxylate-co-propoxylates) of linear C 8 -C 22 -alkanols are preferred. In an analogous manner, poly (ethoxylate-co-propoxylates) of C 1 -C 10 -alkanols are preferred, especially butanol being emphasized.
  • those having a number-average molecular weight M N of not more than 5000 daltons are preferred.
  • a phenoxy radical carries 1, 2 or 3 styryl units and a polyethylene oxide unit PEO or a poly (ethylene oxide-co-propylene oxide) unit PEO / PPO.
  • the PEO unit typically comprises 5 to 50 ethylene oxide groups.
  • Preferred surfactants c.24 can be named by the formula (C 2 H 4 O) n • C 30 H 30 O. wherein n is an integer of 5 to 50 and C30H30O is a tri (styryl) phenol group.
  • a particularly suitable example is Soprophor® BSU (Rhodia).
  • the nonionic block copolymers of surfactant class c.25 comprise at least one poly (ethylene oxide) unit PEO and at least one hydrophobic polyether unit PAO.
  • the PAO unit typically comprises at least 3, preferably at least 5 and especially 10 to 100 repeat units (number average) derived from C3-Cio-alkylene oxides, such as propylene oxide, 1, 2-butylene oxide, cis- or trans-2,3-butylene oxide or isobutylene oxide, 1, 2-pentene oxide, 1, 2-hexene oxide, 1, 2-decene oxide and styrene oxide derived, of which C3-C4 alkylene oxides are preferred.
  • the PAO units comprise at least 50% by weight and more preferably at least 80% by weight of repeating units derived from propylene oxide.
  • the PEO units typically comprise at least 3, preferably at least 5, and more preferably at least 10 repeating units (number average) derived from ethylene oxide.
  • the weight ratio of PEO units to PAO units is usually in the range from 1:10 to 10: 1, preferably from 1:10 to 2: 1, more preferably from 2: 8 to 7: 3 and especially from 3: 7 to 6: 4.
  • the PEO units and the PAO units make up at least 80% by weight, and preferably at least 90% by weight, e.g. From 90 to 99.5 weight percent of the nonionic block copolymer surfactant.
  • Suitable surfactants are described, for example, in WO2006 / 002984, in particular those having the formulas P1 to P5 specified therein.
  • the non-ionic block copolymer surfactants of group c.25 can be obtained, for example, under the trade names Pluronic®, such as Pluronic® P 65, P84, P 103, P 105, P 123 and Pluronic® L 31, L 43, L 62, L 62 LF, L 64, L 81, L 92 and L 121, Pluraflo® such as Piplaflo® L 860, L1030 and L 1060; Tetronic®, such as Tetronic® 704, 709, 104, 1304, 702, 1102, 1302, 701, 901, 10110, 1301 (BASF Aktiengesellschaft), Agrilan® AEC 167 and Agrilan® AEC 178 (Akcros Chemicals), Antarox ® B / 848 (Rhodia), Berol® 370 and Berol® 374 (Akzo Nobel Surface Chemistry), Dowfax® 50 C15, 63 N 10, 63 N30, 64 N40 and 81 N10 (Dow Europe), Genapol®
  • Preferred graft copolymers of group c.26 contain in polymerized form (i) methyl esters or hydroxy C 2 -C 3 alkyl esters of monoethylenically unsaturated C 3 -C 5 carboxylic acid monomers, such as methyl acrylate, methyl methacrylate, hydroxyethyl acrylate and hydroxyethyl methacrylate, and (ii) polyethylene oxide Groups attached to the polymer backbone via either ester bonds or ether bonds.
  • the backbone of the surfactant c.26 contains poly- merterrorismer form methyl methacrylate and Polyethylenoxidester of methacrylic acid, for example, Atlox ® 4913 (Akzo Nobel) are particularly suitable.
  • nonionic block copolymer surfactants from group c.25 are preferably used as dispersants in the suspension concentrates according to the invention.
  • the proportion of the surface-active auxiliary component (d) in the total weight of the composition is generally up to 25% by weight, preferably up to 20% by weight, especially up to 15% by weight, and especially up to 10 wt .-%, based on the total mass of the composition.
  • anti-settling agents comprise a multitude of possible substances. They are familiar to the expert.
  • thickeners i.e., compounds which impart modified flowability to the formulation, i.e., high viscosity at rest and low viscosity when in motion
  • thickeners find use as antisettling or antisettling agents, e.g. Polysaccharides such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (R.T. Vanderbilt) as well as organic and inorganic layer minerals such as Attaclay® (Engelhardt).
  • the antifreeze agents include, for example, dC 4 -alkanols such as ethanol, isopropanol, n-butanol, isobutanol, and C 2 -C 6 -polyols such as glycerol, ethylene glycol, hexylene glycol and / or propylene glycol.
  • dC 4 -alkanols such as ethanol, isopropanol, n-butanol, isobutanol
  • C 2 -C 6 -polyols such as glycerol, ethylene glycol, hexylene glycol and / or propylene glycol.
  • anti-foaming agents examples include silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, e.g. Magnesium stearate, fluoroorganic compounds and mixtures thereof.
  • Bactericides can be added for stabilization.
  • bactericides are bactericides based on diclorophene and Benzylalkoholhemiformal (Proxel® the Fa. ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas) and also isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).
  • the proportion of the auxiliary component (c2) in the total weight of the composition is - if present - usually up to 15 wt .-%, preferably up to 10 wt .-% and in particular up to 5 wt .-%, based on the total mass of agent.
  • the agents may also include dyes. This is especially true if the seeds are intended for seed treatment.
  • dyes include both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned under the names rhodamine B, Cl. Pigment Red 1 12 and Cl.
  • Solvent Red 1 known dyes, as well as pigment blue 15: 4, pigment blue 15: 3, pigment blue 15: 2, pigment blue 15: 1, pigment blue 80, pigment yellow 1, pigment yel- low 13, pigment red 112, pigment red 48: 2, pigment red 48: 1, pigment red 57: 1, pigment red 53: 1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25 , basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • the agent contains a total of at most 60% by weight, preferably at most 45% by weight and in particular at most 30% by weight of further adjuvant (c).
  • the weight ratio of components (a) and (b) to (c) is at least 3, preferably at least 5.
  • the suspension concentrates according to the invention comprise, in addition to the components a) and b) as component d), usually a fluid, preferably a liquid, in which at least part of the active substance is suspended.
  • a fluid preferably a liquid, in which at least part of the active substance is suspended.
  • solubility of the active ingredient in the fluid should not be more than 2 g / l at 25 ° C / 1013 mbar.
  • the fluid may also serve to contain other ingredients, for example, dissolved, dispersed or suspended.
  • suitable fluids is carried out according to the requirements usually by a person skilled in the art.
  • component (d) are in particular:
  • polyhydric C 2 -C 4 -alcohols are ethylene glycol, 1,2-propanediol, 1,3-propanediol, glycerol and 1,4-butanediol, ethylene glycol and 1,3-propanediol being emphasized.
  • the fluid consists essentially of water, ie water makes up at least 99% by weight of the total weight of the fluid (component (d)).
  • the fluid is a mixture of water and at least one of the previously mentioned polyhydric C 2 -C 4 alcohols.
  • the weight ratio of water to polyhydric alcohol is preferably in the range of 99: 1 to 1: 1, more preferably in the range of 50: 1 to 2: 1, and more preferably in the range of 40: 1 to 10: 1
  • the agent contains a total of at least 10% by weight, preferably at least 20% by weight and in particular at least 30% by weight of component d1).
  • the agent contains a total of at most 80 wt .-%, preferably at most 70 wt .-% and in particular at most 60 wt .-% component d1).
  • At least part of the active ingredient in the suspension concentrates is in the form of dispersed particles whose volume average diameter determined by dynamic light scattering is less than 1 ⁇ m, for example not more than 900 nm, 800 nm, 700 nm or 500 nm, z. From 10 to ⁇ 100 nm, 20 to 900 nm, 50 to 800 nm, 70 to 700 nm or 100 to 500 nm.
  • the average particle diameters described herein are volume average particle diameter d (0.5) or d (v 0.5), ie 50% by volume of the particles have a diameter above and 50% of the particles have a diameter below that indicated Mean value lies.
  • Such average particle diameters can be determined by means of dynamic light scattering, which is usually carried out on dilute suspensions containing from 0.01 to 1% by weight of active ingredient. These methods are known to the person skilled in the art and are described, for example, in H. Wiese (D. Distler, Ed.), Aqueous Polymer Dispersions (Aqueous Polymer Dispersions), Wiley-VCH 1999, Chapter 4.2.1, p. 40ff, and the literature cited therein; H. Auweter, D. Horn, J. Colloid Interf. Be.
  • the plant protection agent (pesticide) of the component (e) may be referred to any substance whose purpose or effect is to prevent the infestation of a plant by any pest or repel the pest, deter, destroy or otherwise caused by him To reduce damage.
  • plant pests may belong to different groups of animals; Among the higher animals, insects and mites in particular contain many important pests, as well as nematodes and snails; Vertebrates such as mammals and birds are of secondary importance in industrialized countries today. Numerous groups of microbes including fungi, bacteria including mycoplasmas, viruses and viroids include pests, and also weeds that compete with crops for scarce habitat and other resources may be counted among the pests in the broader sense.
  • Pesticides include, in particular, avicides, acaricides, desiccants, bactericides, chemosterilizers, defoliants, feedstocks, fungicides, herbicides, herbicidal safetics, insect attractants, insecticides, insect repellants, molluscicides, nematicides, mating disrupters, plant activators, plant growth regulators, rodenticides, mammalian quenchers, synergists, avian deterrents and virucides.
  • pesticides include, in particular, acylalanic fungicides, acylamino acid fungicides, aliphatic amide organothiophosphate insecticides, aliphatic organothiophosphate insecticides, aliphatic nitrogen fungicides, amide fungicides, amide herbicides, anilide fungicides, anilide herbicides, inorganic fungicides, inorganic herbicides, inorganic rodenticides, antiauxins, antibiotic acaricides , antibiotics, fungicides, antibiotics, herbicides, antibiotics, insecticides, Antibiotikanematizide, Aromaten Acidfungizide, AromatenLiterenherbizide, arsenic herbicides, arsenic insecticides, Arylalaninherbizide, Aryloxyphenoxypropionchureherbizide, auxins, Avermectina- carizide, Avermectininsektizide, Benza
  • Phthalatherbizide Phthalimidacarizide, Phthalimidfungizide, Phthalimidinsektizide, PI colatherbizide, polymeric dithiocarbamate fungicides, Polysulfidfungizide, Precocene, Py- razolacarizide, Pyrazolfungizide, Pyrazolinsektizide, Pyrazolopyrimidineorganothio- phosphate insecticidal, Pyrazolyloxyacetophenonherbizide, Pyrazolylphenylherbizide, Py- rethroidacarizide, acaricidal Pyrethroidesteracarizide, Pyrethroidesterinsektizide, Pyrethroidether-, Pyrethroidetherinsektizide, pyrethroid insecticides , Pyridazinherbizide, pyrid azinonherbizide, Pyridinfungizide, Pyridinherbizide, Pyridinorgan
  • the pesticide for use according to the invention is selected in particular from fungicides (e1), herbicides (e2) and insecticides (e3).
  • Fungicides include, for example, aliphatic nitrogen fungicides such as butylamine, cadmoxanil, dodicin, dodine, guazatine, iminoctadine; Amide fungicides, such as carpropamide, chloraniformethane, cyflufenamid, diclocymet, ethaboxam, fenoxanil, flumetover, fumaretpyr, mandipropamide, penthiopyrad, prochloraz, quinazamide, silthiofam, triforine; in particular acylamino acid fungicides, such as benalaxyl, benalaxyl-M, furalaxyl, meta-laxyl, metalaxyl-M, pefurazoate; Anilide fungicides, such as benalaxyl, benalaxyl-M, boscalid, carboxin, fenhexamide, metalaxy
  • fungicides (e1) include:
  • strobilurins such as Azoxystrobin, dimoxystrobin, enestroburine, fluoxastrobin,
  • Carboxylic anilides such as B. Benalaxyl, Benodanil, Boscalid, Carboxin, Me- pronil, Fenfuram, Fenhexamid, Flutolanil, Furametpyr, Metalaxyl, Ofurace,
  • Suitable carboxylic acid anilides are also Benaxa IyI-M, Bixafen, Isotianil, Kiralaxyl, Tecloftalam, 2-amino-4-methylthiazole-5-carboxylic acid anilide, 2-chloro-N- (1, 1, 3-trimethylindan-4-ylnicotinamid, N - (3 ', 4'-
  • Carboxylic acid morpholides such as. Eg dimethomorph, flumorph
  • Benzoic acid amides such as. Flumetover, fluopicolide (picobenzamide), zoxamide. Also suitable is N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formuylamino
  • carboxylic acid amides such as. Carpropamide, diclocymet, mandipropamide, N- (2- (4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-methylsulfonylamino 3-methylbutyramide, N- (2- [4- [3- (4-chloro-phenyl) -prop-2-ynyloxy] -3-methoxyphenyl) -ethyl) -2-ethylsulfonylamino-3-methyl- butyramide.
  • Triazoles such as. B. bitertanol, bromuconazoles, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fenbuconazole, flusilazole, flucinconazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, Tetraconazole, triadimenol, triadimefon, triticonazole;
  • imidazoles such as Cyazofamide, imazalil, pefurazoate, prochloraz, triflumizole;
  • Benzimidazoles such as. Benomyl, carbendazim, fuberidazole, thiabendazoles; and others, such as ethaboxam, etridiazoles, hymexazoles;
  • pyridines such as Fluazinam, pyrifenox, 3- [5- (4-chloro-phenyl) -2,3-dimethylisoxazolidin-3-yl] -pyridine;
  • Pyrimidines such as. B. bupirimate, cyprodinil, ferimzone, fenarimol, panipyrim, nuarimol, pyrimethanil;
  • Pyrroles such as fludioxonil, fenpiclonil
  • Morpholines such as aldimorph, dodemorph, fenpropimorph, tridemorph
  • Dicarboximides such as iprodione, procymidone, vinclozolin; • others, such as acibenzolar-S-methyl, anilazine, captan, captafol, dazomet, di-zimezine, fenoxanil, folpet, fenpropidin, famoxadone, fenamidone, octhilinone, probenazole, proquinazide, pyroquilone, quinoxyfen, tricyclazole, 6-aryl [1,2,4] triazolo [1,5-a] pyrimidines, for example compounds of formula (IV) defined below, e.g.
  • Dithiocarbamates such as Ferbam, Mancozeb, Maneb, Metiram, Metam, Propineb, Thiram, Zineb, Ziram;
  • Carbamates such as diethofencarb, flubenthiavalicarb, iprovalicarb, propamocarb, 3- (4-chlorophenyl) -3- (2-isopropoxycarbonylamino-3-methyl-butyrylamino) -propionic acid methyl ester, N- (1- (1- (4-cyanophenyl ethylsulfonyl) -but-2-yl) -carbamic acid (4-fluorophenyl) ester;
  • Guanidines such as dodine, iminoctadine, guazatine
  • Antibiotics such as kasugamycin, polyoxins, streptomycin, validamycin A;
  • Organometallic compounds such as fentin salts
  • Sulfur-containing heterocyclyl compounds such as isoprothiolanes, dithianone;
  • Organophosphorus compounds such as edifenphos, fosetyl, fosetylaluminum, Iprobenfos, pyrazophos, tolclofos-methyl, phosphorous acid and their salts;
  • Organochlorine compounds such as thiophanate methyl, chlorothalonil, dichlofluanid, tolylfluanid, flusulphamides, phthalides, hexachlorobenzene, pencycuron, quintocene;
  • Nitrophenyl derivatives such as binapacryl, dinocap, dinobuton; • Other, such as Spiroxamine, cyflufenamid, cymoxanil, metrafenone.
  • Herbicides (e2) include, for example, amide herbicides such as allidochlor, beflubutamide, benzadox, benzipram, bromobutide, cafenstrole, CDEA, chlorthiamide, cyprazole, dimethenamid, dimethenamid-P, diphenamid, epronaz, etnipromide, fentrazamide, flupoxam, fomesafen, halosafen, isocarbamide, Isoxaben, napropamide, naptalam, pethoxamide, propyzamide, quinone amide, tebutam; in particular anilide herbicides such as chloranocryl, cisanilide, clomeprop, cypromide, diflufenican, etobenzanide, fenasulam, flufenacet, flufenican, mefenacet, mefluidide, metamifop
  • herbicides (e2) include: 1, 3,4-thiadiazoles such as buthidazoles and cyprazoles;
  • Amides such as allidochlor, benzoylpropyl, bromobutide, chlorthiamide, dimepiperate, dimethenamid, diphenamid, etobenzanide, flampropmethyl, fosamine, isoxaben, metazite, monalides, naptalame, pronamide, propanil;
  • Aminophosphoric acids such as bilanafos, buminafos, glufosinate-ammonium, glyphosate, sulfosates;
  • Aminotriazoles such as amitrole, anilides such as anilofos, mefenacet;
  • Anilides such as anilofos, mefenacet
  • Aryloxyalkanoic acid such as 2,4-D, 2,4-DB, Clomeprop, dichlorprop, dichlorprop-P, fenoprop, fluroxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napro-panilide, triclopyr;
  • Benzoic acids such as Chloramben, Dicamba;
  • Benzothiadiazinones such as bentazone
  • Bleachers such as Clomazone, Diflufenican, Fluorochloridone, Flupoxam, Fluridone, Pyrazolate, Sulcotrione; Carbamates such as carbetamide, chlorobufam, chlorpropham, desmedipham,
  • dihydrobenzofurans such as ethofumesates
  • dihydrofuran-3-ones such as flurtamones
  • Dinitroanilines such as Benefin, Butraline, Dinitramine, Ethalfluralin, Fluchloralin, Isopropaline, Nitralin, Oryzalin, Pendimethalin, Prodiamine, Profluralin, Trifluralin,
  • Dinitrophenols such as bromofenoxime, dinoseb, dinoseb acetate, dinoterb, DNOC, medinoterb acetate; Diphenyl ethers such as acifluorfen-sodium, aclonifen, bifenox, chloronitrofen,
  • Dipyridyls such as cyperquat, difenzoquat-methylsulfate, diquat, paraquat-dichloride;
  • Imidazoles such as isocarbamide; Imidazolinones such as imazamethapyr, imazapyr, imazaquin, imazamethabenzomethyl, imazethapyr, imazapic, imazamox;
  • Oxadiazoles such as methazoles, oxadiargyl, oxadiazon;
  • Phenols such as bromoxynil, loxynil; Phenoxyphenoxypropionic acid esters such as clodinafop, cyhalofop-butyl, diclofopmethyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenthiapropethyl, fluazifop-butyl, fluazifop-p-butyl, haloxyfop-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl , Isoxapyrifop, propaquizafop, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-tefuryl;
  • Phenylacetic acids such as chlorfenac;
  • Ppi agents such as benzofenap, flumiclorac-pentyl, flumioxazine, flumipropyne, flupropacil, pyrazoxyfen, sulfentrazone, thidiazimin; • pyrazoles such as Nipyraclofen;
  • Pyridazines such as Chloridazon, Maleic hydrazide, Norflurazon, Pyridate;
  • Pyridinecarboxylic acids such as clopyralid, dithiopyr, picloram, thiazopyr;
  • Pyrimidyl ethers such as pyrithia-bac acid, pyrithiobac-sodium, KIH-2023, KIH-6127;
  • sulfonamides such as flumetsulam, metosulam
  • Triazole carboxamides such as triazofenamide
  • Uracils such as bromacil, lenacil, terbacil;
  • Benazoline Benfuresate, Bensulide, Benzofluor, Bentazone, Butamifos, Cafenstrole, Chlorthal-dimethyl, Cinmethylin, Dichlobenil, Endothall, Fluoroben- tranil, Mefluidide, Perfluidone, Piperophos, Topramezone and Prohexadione-Calcium;
  • Sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, flazasulfuron, halosulfuron-methyl, imazosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, prosulfuron, pyrazosulfuron-ethyl, Rimsul - furon, sulfometuron-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, triflusulfuron-methyl, tritosulfuron;
  • Cyclohexenone-type pesticides such as alloxydim, clethodim, cloproxydim, cycloxydim, sethoxydim and tralkoxydim.
  • Very particularly preferred cyclohexenone-type herbicidal active compounds are: tepraloxydim (compare AGROW, No. 243, 3.1.195, page 21, cycloxydim) and 2- (1- [2- ⁇ 4-
  • Insecticides include, for example, antibiotic insecticides such as allosamidin, thurin giensin; in particular macrocyclic lactone insecticides such as spinosad; in particular vermectin insecticides, such as abamectin, doramectin, emamectin, eprinomectin, ivermectin, selamectin; and milbemycin insecticides such as lepimectin, milbemectin, milbemycin oxime, moxidectin; Arsenic insecticides, such as calcium arsenate, copper aceto-arsenite, copper senate, lead arsenate, potassium arsenite, sodium arsenite; herbal insecticides, such as anaba- sin, azadirachtin, D-limonene, nicotine, pyrethrins, cinerine E, cinerine I, cinerine II, jasminin I, jas
  • Organo (thio) phosphates such as acephates, azamethiphos, azinphos-ethyl, azinphos-methyl, cadudsafos, chloroethoxyphos, chlorfenvinphos, chloremephos, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinphos, coumaphos, cyanophos, demeton-S-methyl, diazinon , Dichlorvos / DDVP, dicrotophos, dimethoates, dimethylvinphos, disulphoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthione, fosthiazate, heptenophos, isoxathione, malathion, mecarbam, methamidophos, methidathione, methylparathion, mevinphos , Monocrotophos,
  • Carbamates such as alanycarb, aldicarb, bendoxycarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfane, ethiofencarb, fenobucarb, fenoxycarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox , Triazemates, trimethacarb, XMC, xylylcarb;
  • Pyrethroids such as acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin , Cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, deltamethrin, pententhrine, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin,
  • Arthropod growth regulators a) chitin synthesis inhibitors z.
  • B. benzoylureas such as bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenonoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, clofentezine;
  • ecdysone antagonists such as chromafenozides, halofenozides, methoxyfenozides,
  • Tebufenozide Azadirachtin
  • juvenoids such as pyriproxyfen, hydroprene, kynoprenes, methoprene, fenoxycarb
  • lipid biosynthesis inhibitors such as spirodicofen, spiromesifen, spirotetramat
  • Agonists / antagonists of nicotine receptors acetamiprid, clothianidin, di-notafuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, nicotine, benign sultap, cartap hydrochloride, thiocyclam, sodium thiosultap; the thiazole compound of the formula (F 1 )
  • GABA antagonists such as acetoprole, chlordane, endosulfan, ethiprole, gamma-HCH (lindane), fipronil, vaniliprole, pyrafluprol, pyriprole, vaniliprole, phenylpyrazole compounds of the formula F 2
  • Macrocyclic lactones such as abamectin, emamectin, emamectin benzoates, miimectectin, lepimectin, spinosad;
  • METI I compounds such as Fenazaquin, Fenpyroximate, Flufenerim, Pyridaben, Pyrimidifen, Rotenone, Tebufenpyrad, Tolfenpyrad;
  • METI II and III compounds such as acequinocyl, fluacrypyrim, hydramethylnone;
  • decoupling compounds such as Chlorfenapyr, DNOC
  • inhibitors of oxidative phosphorylation such as azocyclotine, cyhexatin, di-thiuron, fenbutatin oxide, propargite, tetradifone;
  • oxidase inhibitors such as piperonyl butoxide
  • Microbial disruptors such as Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis;
  • a 1 is CH 3 , Cl, Br, I, X is CH, C-Cl, CF or N, Y 'is F, Cl or Br, Y "is F, Cl, CF 3 , B 1 is hydrogen, Cl, Br, I, CN, B 2 is Cl, Br, CF 3 , OCH 2 CF 3 , OCF 2 H and R B is hydrogen, CH 3 or CH (CH 3 ) 2 , and malononitriles as described in JP 2002 284608, WO 02/89579, WO 02/90320, WO 02/90321, WO 04/06677, WO 04/20399 or JP 2004 99597.
  • R is methyl or ethyl and Het * for 3,3-dimethylpyrrolidin-1-yl, 3-methylpiperidin-1-yl, 3,5-dimethylpiperidin-1-yl, 4-methylpiperidin-1-yl, hexa-hydroazepine 1-yl, 2,6-dimethylhexahydroazepin-1-yl or 2,6-dimethylmorpholin-4-yl.
  • salts in particular agriculturally useful salts.
  • the crop protection agent is a fungicide.
  • the fungicide is an active ingredient from the group of anilides, triazolopyrimidines, strobilurins or triazoles, in particular an anilide selected from boscalid, carboxin, metalaxyl and oxadixyl, the triazolopyrimidine 5-chloro-7- (4-methylpiperidin 1-yl) -6- (2,4,6-trifluorophenyl) - [1,2,4] triazolo [1,5-a] -pyrimidine, a strobilurin selected from azoxystrobin, pyraclostrobin, dimoxystrobin, trifloxystrobin, fluoxystrobin , Picoxystrobin and orysastrobin or a triazole selected from epoxiconazole, metconazole, tebuconazole, flusilazole, fluquinconazole, triticonazole, propiconazole, penconazole, cyproconazo
  • Particularly preferred according to the invention is the use of epoxiconazole.
  • plant protection active ingredients chosen here includes isomeric forms of this compound. Particular mention may be made of stereoisomers, such as enantiomers or diastereoisomers of the formulas. In addition to the substantially pure isomers belonging to the compounds of formulas and their isomer mixtures, eg. B. stereoisomer mixtures.
  • Agents with a higher proportion of the biologically more active stereoisomer than the optical antipode are generally preferred, particularly preferably isomerically pure active ingredients.
  • the proportion of the active ingredient component (e) in the total weight of the agent is usually more than 1 wt .-%, preferably more than 2 wt .-% and in particular more than 2.5 wt .-% of.
  • the proportion of component (e) in the total weight of the composition is usually less than 65% by weight, preferably less than 50% Wt .-% and in particular less than 40 wt .-%, based on the total mass of the composition of.
  • the amount of alcohol alkoxylate based on the amount of active ingredient i. the weight ratio of alcohol alkoxylate to crop protection agent at least 0.5, preferably at least 1 and in particular at least 2.
  • the invention relates to suspension concentrates comprising: (a) 1 to 50% by weight, preferably 5 to 50% by weight, e.g. about 25% by weight of alcoholic acylate; (b) 0.5 to 50% by weight, preferably 5 to 50% by weight, e.g. about 25% by weight of cyclodextrin;
  • (c2) 0.1 to 10% by weight, preferably 1 to 10% by weight, e.g. about 5% by weight anti-settling agent; (d) 10 to 80% by weight, preferably 5 to 50% by weight, e.g. about 27.5% by weight of water; and (e) 1 to 65% by weight, preferably 5 to 50% by weight, e.g. about 12.5 wt .-% crop protection agent.
  • suspension concentrates according to the invention can be prepared in a manner known per se, for example by a process which comprises the following process steps:
  • the ingredients may be mixed together in conventional, suitable apparatus. There should be sufficient shear force on the mixture to ensure the maintenance of a suspension.
  • the grinding can also be carried out in a manner known per se. Preference is given to wet grinding processes in corresponding devices, with ball mills in particular having proven particularly advantageous, for example the Drais Superfinlow DCP SF 12 ball mill from DRAISWERKE, INC.
  • Another object of the present invention is the pesticides, especially fungicidal, insecticidal or herbicidal, treatment of plants and their habitats with a suspension concentrate of the invention or the use of the disclosed suspension concentrates for pesticides, especially fungicides, insecticides or herbicides, treatment of plants and their habitats.
  • the suspension concentrates according to the invention are usually prepared by the user, e.g. the farmer or gardener, in a basically known manner by dissolving, dispersing or emulsifying in water in a ready-to-use administration form, e.g. processed into a spray mixture (tank mix method).
  • the application of the spray mixtures applied can be carried out in a generally known manner by spraying, in particular by spraying, for example with a mobile spraying machine, by means of very finely distributing nozzles.
  • spraying in particular by spraying, for example with a mobile spraying machine, by means of very finely distributing nozzles.
  • the devices and working techniques still used for this purpose are known to the person skilled in the art.
  • the treatment of plants and their habitats in the spray process is preferred if the preparation of the spray mixture to be applied takes place by dissolving, dispersing or emulsifying.
  • a further subject of the present invention is a spray mixture containing a suspension concentrate according to the invention for the pesticidal treatment of plants.
  • the spray mixture contains 0.0001 to 10 wt .-%, preferably 0.001 to 1 wt .-% and in particular 0.01 to 0.5 wt .-% crop protection agent. This corresponds to about 0.01 to 5 wt .-%, preferably 0.05 to 3 wt .-% and in particular 0.1 to 2 wt .-% of inventive suspension onskonzentrat.
  • the suspension concentrates according to the invention show better activity than comparable suspension concentrates without alcohol alkoxylate. Even over long periods of time, no appreciable agglomeration of the active ingredient particles is observed.
  • the suspension concentrates can be easily diluted with water, resulting in spray liquors, which are stable in themselves, and can be applied advantageously.
  • Epoxiconazole 62.5 g Epoxiconazole were milled in an agitating ball mill (Dynomühle) together with 20 g / l dispersant (Atlas G 5000 (Uniquema / Croda), Synperonic A (Uniquema / Croda)) and 50 g / l of propylene glycol in an aqueous medium until a particle size of 80% ⁇ 2 microns was achieved.
  • To the mixture was added 3 g / l of antifoam, eg Rhodorsil 426 (Rhodia), 3 g / l of thickener, eg Thodopol 23 (Rhodia) and a biocide, eg Acticide MBS (Thor Chemie).
  • alcohol alkoxylate (a C 9 -Cn alcohol + 7 EO + 1, 5 BO) were stirred into this mixture until the formulation was homogeneous.
  • the same or twice the amount of cyclodextrin (Cavamax W 6 or W 7 or W 8, ⁇ -cyclodextrin, ⁇ -cyclodextrin or ⁇ -cyclodextrin from Wacker Chemie AG, Germany) was then stirred into these mixtures and homogenized for 2 hours. Finally, the batches were made up to 1 liter with water.
  • the percentage of the suspended active ingredient was determined with a particle size of less than 2 microns.

Abstract

L'invention porte sur des suspensions concentrées d'un agent phytosanitaire, contenant de l'alcoxylat d'alcool et de la cyclodextrine. Elle concerne également des procédés de préparation desdites suspensions concentrées et l'utilisation desdites suspensions concentrées pour le traitement de plantes et de leur habitat, ainsi que des procédés correspondants, et des bouillies de pulvérisation contenant une telle suspension concentrée.
EP09734510A 2008-04-24 2009-04-23 Suspensions concentrées contenant de la cyclodextrine, leur procédé de préapartion et leur utilisation Withdrawn EP2278877A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP09734510A EP2278877A2 (fr) 2008-04-24 2009-04-23 Suspensions concentrées contenant de la cyclodextrine, leur procédé de préapartion et leur utilisation

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Application Number Priority Date Filing Date Title
EP08155134 2008-04-24
EP09734510A EP2278877A2 (fr) 2008-04-24 2009-04-23 Suspensions concentrées contenant de la cyclodextrine, leur procédé de préapartion et leur utilisation
PCT/EP2009/054899 WO2009130282A2 (fr) 2008-04-24 2009-04-23 Suspensions concentrées contenant de la cyclodextrine, leur procédé de préapartion et leur utilisation

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EP2278877A2 true EP2278877A2 (fr) 2011-02-02

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US (1) US20120021914A1 (fr)
EP (1) EP2278877A2 (fr)
JP (1) JP2011518806A (fr)
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WO (1) WO2009130282A2 (fr)

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GB0907003D0 (en) * 2009-04-23 2009-06-03 Syngenta Ltd Formulation
CN106117231B (zh) * 2010-09-14 2019-09-03 巴斯夫欧洲公司 含有啶南平杀虫剂和助剂的组合物
CN103748181B (zh) 2011-03-16 2016-10-12 科莱恩金融(Bvi)有限公司 作为水性分散性涂料的除气的润湿剂和分散剂的支化聚亚烷基二醇醚
JP5777478B2 (ja) * 2011-10-12 2015-09-09 信越化学工業株式会社 水分散型性フェロモン徐放製剤
US20160120181A1 (en) * 2013-05-10 2016-05-05 Syngenta Participations Ag Physically and chemically stable agrichemical formulations
AU2015257857B2 (en) * 2014-05-06 2019-01-17 Basf Se Composition comprising a pesticide and a hydroxyalkyl polyoxylene glycol ether
CN108137459B (zh) 2015-10-07 2021-06-18 海名斯精细化工公司 润湿-防泡剂
JPWO2019216296A1 (ja) * 2018-05-08 2021-05-13 日産化学株式会社 水性懸濁状農薬組成物
BR112020021363A2 (pt) * 2018-05-09 2021-01-19 Adama Makhteshim Ltd. Uso de ciclodextrinas como sistema de distribuição de agroquímico
US20210212321A1 (en) * 2018-06-01 2021-07-15 Bayer Cropscience Lp Stabilized fungicidal composition comprising cyclodextrin
JP7391962B2 (ja) * 2018-12-11 2023-12-05 ダウ グローバル テクノロジーズ エルエルシー ポリアルコキシル化アミノアルコールを使用する難溶性有効成分の水溶液

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JP2011518806A (ja) 2011-06-30
US20120021914A1 (en) 2012-01-26
BRPI0909773A2 (pt) 2015-10-06
WO2009130282A3 (fr) 2010-06-17

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