WO2003075657A1 - Pesticidal composition comprising a lactate ester as crystal growth inhibitor - Google Patents

Pesticidal composition comprising a lactate ester as crystal growth inhibitor Download PDF

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Publication number
WO2003075657A1
WO2003075657A1 PCT/IL2003/000222 IL0300222W WO03075657A1 WO 2003075657 A1 WO2003075657 A1 WO 2003075657A1 IL 0300222 W IL0300222 W IL 0300222W WO 03075657 A1 WO03075657 A1 WO 03075657A1
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WO
WIPO (PCT)
Prior art keywords
lactate
rosin
composition
ester
pesticide
Prior art date
Application number
PCT/IL2003/000222
Other languages
French (fr)
Inventor
Yoel Sasson
Ofer Toledano
Ganit Levi-Ruso
Original Assignee
Makhteshim Chemical Works Ltd.
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
Priority to EP03710187A priority Critical patent/EP1482790B8/en
Priority to DK03710187T priority patent/DK1482790T3/en
Priority to EA200401079A priority patent/EA007031B1/en
Priority to NZ535303A priority patent/NZ535303A/en
Priority to MXPA04008923 priority patent/MX243369B/en
Priority to KR1020047014426A priority patent/KR101058816B1/en
Priority to CA2479053A priority patent/CA2479053C/en
Priority to APAP/P/2004/003139A priority patent/AP2004003139A0/en
Application filed by Makhteshim Chemical Works Ltd. filed Critical Makhteshim Chemical Works Ltd.
Priority to SI200331318T priority patent/SI1482790T1/en
Priority to YUP-809/04A priority patent/RS80904A/en
Priority to BRPI0308455A priority patent/BR0308455B1/en
Priority to AU2003214607A priority patent/AU2003214607B2/en
Priority to JP2003573944A priority patent/JP4657607B2/en
Priority to US10/507,103 priority patent/US20050169951A1/en
Priority to DE60322676T priority patent/DE60322676D1/en
Publication of WO2003075657A1 publication Critical patent/WO2003075657A1/en
Priority to HR20040815A priority patent/HRP20040815A2/en

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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
    • A01N25/02—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
    • 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
    • A01N25/22—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 ingredients stabilising the active ingredients
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to the field of pesticidal compositions, particularly to the use of lactate acid esters as a crystal growth inhibitor in said compositions.
  • EP 637,202 describes a liquid pesticidal composition containing as crystallization inhibitor benzene which contains two or three hydroxy groups and substituted by one or more lower alkyl groups.
  • crystallization inhibitors are organic substances which are essentially insoluble in an aqueous medium.
  • the current practice in pest control is to reduce the use of organic solvents.
  • WO 00/35284 describes an aqueous suspension concentrate of triazole fungicides which contains a tristyrylphenol-ethoxylate, phosphate or sulfate thereof, with a vinylpyrrolidon polymer or copolymer thereof, as a crystal growth inhibitor.
  • a mixture of crystallization inhibitors at least a binary mixture thereof.
  • the crystal growth inhibitors disclosed in the prior publications do not offer a solution for all needs, practices and conditions employed in agriculture.
  • the crystal growth inhibitor may vary in accordance with the active ingredient.
  • there is an ongoing need to develop further crystal growth inhibitors which overcome the shortcomings of the prior art.
  • a further purpose of the present invention is to present the new use of a compound as a crystal growth inhibitor.
  • Yet a further purpose of the present invention is to provide a method for crystal growth inhibition in pesticidal compositions.
  • the present invention provides a method for preventing crystallization of pesticidal compositions during application, comprising adding a lactate ester as a crystallization prevention agent to the composition.
  • the present invention provides a liquid pesticidal composition comprising one or more pesticide as an active ingredient and a lactate ester as a crystal growth inhibitor.
  • esters of lactic acid are effective as crystal growth inhibitor in liquid pesticidal compositions.
  • lactate esters and esters of lactic acid are used it is meant to include both optical isomers as well as mixtures thereof.
  • mixtures of lactate esters with rosin gum, or derivatives thereof selected from among a group comprising of rosin gum, rosin esters, modified rosins, hydro genated rosin esters, polymerized rosin esters and phenolic modified rosin esters or mixtures thereof prevent the crystallization in the pesticidal composition.
  • Pesticides suitable for the practice of the present invention may be, but are not limited to azole fungicides selected from among a group comprising of epoxiconazole, tebuconazole, cyproconazole, prochloraz, penconazole, defenoconazole, flusilazole, metconazole, triadimenol, hexaconazole, flutriafol, triflumizole, fenbuconazole, bromuconazole, fluquinconazole, azaconazole, triticonazole, triadimefon and imibenconazole; strobilurin analogues, e.g. kresoxim-methyl and pyraclostrobin; maneb, mancozeb, ziram, thiram and mixtures thereof.
  • azole fungicides selected from among a group comprising of epoxiconazole, tebuconazole, cy
  • the present invention there is provided a method for preventing crystallization of pesticidal compositions during application, comprising adding a lactate ester or a mixture of lactate esters as a crystallization prevention agent to the composition.
  • prevention of crystallization also encompasses "inhibition” of crystallization.
  • the lactate ester is added to a pesticidal composition so that the lactate ester is 3% to 80% of the total composition, preferably 20% to 60%.
  • a lactate ester is added to a pesticidal composition so that the weight ratio between the pesticide and the lactate ester is from 1:0.2 to 1:5, preferably 1:1 to 1:4.
  • lactate ester also encompasses mixtures of lactate esters.
  • a mixture of LA ester and a Rosin derivative are added as a crystallization prevention agent.
  • the LA ester is added according to the aforementioned percentages or ratios.
  • a Rosin derivative is added to a pesticidal composition so that the Rosin derivative is 0.5% 0 to 20% of the total pesticidal composition, preferably 1% to 10%>.
  • a Rosin derivative may be added so that the weight ratio between the Rosin derivative and the pesticide is from 1:0.05 to 1:1, preferably 1:0.1 to 1:0.5.
  • the preferred lactate esters for the practice of the invention are lactate acid esters of C 4 to C 12 saturated and unsaturated alkyl, C 4 to C 12 saturated and unsaturated cyclically, C 4 to C 12 saturated and unsaturated branched alkyl lactates and mixtures thereof.
  • Particularly preferable lactate esters are 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof.
  • the preferred Rosin derivative is rosin gum.
  • a lactate ester is added to a pesticidal composition in order to prevent crystallization during application, wherein the pesticidal composition contains, subsequent to the addition, 3% to 80%, preferably 10% to 50% of a pesticide selected from among a group comprising of tebuconazole, epoxiconazole and prochloraz and 3% to 80%, preferably 20% to 60% lactate ester selected from among a group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof.
  • a pesticide selected from among a group comprising of tebuconazole, epoxiconazole and prochloraz
  • 3% to 80% preferably 20% to 60% lactate ester selected from among a group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcycl
  • a lactate ester and Rosin derivative are added to a pesticidal composition in order to prevent crystallization during application, wherein the pesticidal composition contains, subsequent to the addition, 3% to 80% , preferably 10% to 50% of a pesticide selected from among a group comprising of tebuconazole, epoxiconazole and prochloraz 3% to 80%, preferably 20% to 60% lactate ester selected from among a group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof, and 0.5% to 20%, preferably 1%> to 10% of a Rosin derivative selected from among a group comprising of rosin gum, rosin esters, modified rosins, hydrogenated rosin esters, polymerized rosin esters and phenolic modified rosin esters.
  • the present invention further provides a pesticidal composition which does not crystallize during application.
  • Said composition comprising a pesticide or mixture of pesticides as active ingredient and a lactate ester.
  • the composition comprising 3% to 80%, preferably 10% to 50% of a pesticide or mixture of pesticides and 3% to 80%>, preferably 20%o to 60% lactate ester.
  • a pesticidal composition which does not crystallize during application comprises 3% to 80%, preferably 10% to 50% of a pesticide or mixture of pesticides, 3% to 80%, preferably 20% to 60% lactate ester and 0.5% to 20%, preferably 1% to 10% of a Rosin derivative.
  • the present compositions comprise 10% to 50% pesticide selected from among a group comprising of tebuconazole, epoxiconazole and prochloraz, 20% to 60% of lactate ester selected from among a group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof, and 0.5% to 20% of a Rosin derivative selected from among a group comprising of rosin gum, and methyl ester of rosin gum.
  • compositions according to the present invention may further contain surfactant agents, thickeners, anti-foaming agents, dispersing agents and wetting agents.
  • 1% to 40% of the present composition may be surfactant agents wherein non-limiting examples of suitable surface-active compounds are nonionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties.
  • surfactants will also be understood as comprising mixtures of surfactants.
  • Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surface-active compounds.
  • Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (C 10 -C 22 ), e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained, e.g. from coconut oil or tallow oil.
  • Further suitable surfactants are also the fatty acid methyltaurin salts as well as modified and unmodified phospholipids.
  • so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
  • the fatty sulfonates or sulfates are usually in the form of alkali metal salts, alkali earth metal salts or unsubstituted or substituted ammonium salts and contain a C 8 -C 22 alkyl radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, of dodecylsulfate, or of a mixture of fatty alcohol sulfates obtained from natural fatty acids.
  • acyl radicals e.g. the sodium or calcium salt of lignosulfonic acid, of dodecylsulfate, or of a mixture of fatty alcohol sulfates obtained from natural fatty acids.
  • These compounds also comprise the salts of sulfuric acid esters and sulfonic acids of fatty alcohol/ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms.
  • alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonic acid/formaldehyde condensation product.
  • corresponding phosphates e.g. salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 moles of ethylene oxide.
  • Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, or saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.
  • non-ionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit.
  • non-ionic surfactants are nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
  • Fatty acid esters of polyoxyethylene sorbitan, e.g. polyoxyethylene sorbitan trioleate, are also suitable non-ionic surfactants.
  • Cationic surfactants are preferably quaternary ammonium salts which contain, as N-substituent, at least one C 8 -C 22 alkyl radical and, as further substituents, unsubstituted or halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals.
  • the salts are preferably in the form of halides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammonium chloride or benzyldi (2-chloroethyl) ethylammonium bromide, preferably 1% to 40%.
  • Anti-foaming agents (AF) suitable for use in the present composition are those customarily employed in pesticidal compositions, wherein non-limiting examples of said agents are silicon oils or silicon oil emulsions in water commercially available as, e.g., Dapro DF-1161, wherein 0% to 1% of anti-foaming agent are employed, preferably 0% to 0.2%.
  • compositions of the present invention can be either aqueous or non-aqueous compositions which contain 0% to 50%> water.
  • Non-limiting examples of such compositions are: emulsifiable concentrates (EC) and emulsion in water (EW) formulations.
  • Example 1 Non-crystallizing formulation of tebuconazole
  • NMP N-Methyl Pyrrolydone
  • Example 4 Formulation of a mixture of prochloraz and tebuconazole
  • the formation of crystals in spraying solutions is determined in various conditions in order to assure no crystal formation in various spraying conditions.
  • 10 liters of spraying solutions are prepared using hard water (CIPAC standard water D, 342 ppm) in 3 different concentrations: 0.5, 1, 2 times the recommended spraying concentration for each formulation. Each sample is placed at 3 different temperatures: 2°C, 15°C and 30°C for 24 hours to allow crystal growth.
  • the solutions are sprayed using a personal spraying machine and using two filters ( ⁇ 8 gr. each): 100 and 50 mesh. After spraying the filters are dried and weighed. A weight difference of the filter before and after spraying of less than 0.05 gr. indicates essentially no crystal growth. Hence, there will not be filter blocking.

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Abstract

The present invention is a method of preventing crystallization of pesticidal compositions during application by adding a lactate ester as a crystallization preventing agent.

Description

PESTICIDAL COMPOSITION COMPRISING A LACTATE ESTER AS CRYSTAL GROWTH INHIBITOR
Field of the Invention
The present invention relates to the field of pesticidal compositions, particularly to the use of lactate acid esters as a crystal growth inhibitor in said compositions.
Background of the Invention
Perhaps the most prevalent practice for applying pesticides to plants is by spraying a liquid composition onto the plant. Some technical difficulties are associated with this practice when predominantly aqueous compositions of pesticides which are essentially water insoluble, are employed, h such cases, often certain parts of the spraying equipment, e.g. filters and nozzles, are clogged as a result of crystal growth of the water- insoluble pesticide in said parts. A particular method for overcoming this problem is by inhibiting or preventing the crystal growth of the pesticide in the sprayer parts by employing a crystal growth inhibitor in the pesticidal composition. U.S. 5,206,225 describes the employment of alkylcarboxylic acid dimethylamides as crystallization inhibitors of azole fungicides. EP 637,202 describes a liquid pesticidal composition containing as crystallization inhibitor benzene which contains two or three hydroxy groups and substituted by one or more lower alkyl groups. Notwithstanding, the prior art crystallization inhibitors are organic substances which are essentially insoluble in an aqueous medium. Hence, it is necessary to employ an organic co-solvent in which the pesticide and crystal growth inhibitor are soluble. This may present difficulties in terms of environmental safety and phytotoxicity. The current practice in pest control is to reduce the use of organic solvents.
WO 00/35284 describes an aqueous suspension concentrate of triazole fungicides which contains a tristyrylphenol-ethoxylate, phosphate or sulfate thereof, with a vinylpyrrolidon polymer or copolymer thereof, as a crystal growth inhibitor. However, in order to inhibit crystal growth according to WO 00/35284 it is necessary to employ a mixture of crystallization inhibitors; at least a binary mixture thereof. Furthermore, the crystal growth inhibitors disclosed in the prior publications do not offer a solution for all needs, practices and conditions employed in agriculture. The crystal growth inhibitor may vary in accordance with the active ingredient. Thus, there is an ongoing need to develop further crystal growth inhibitors which overcome the shortcomings of the prior art.
It is therefore a purpose of the present invention to provide a pesticidal composition with a new crystal growth inhibitor.
A further purpose of the present invention is to present the new use of a compound as a crystal growth inhibitor.
Yet a further purpose of the present invention is to provide a method for crystal growth inhibition in pesticidal compositions.
Other objects of the invention will become apparent as the description proceeds.
Summary of the Invention
The present invention provides a method for preventing crystallization of pesticidal compositions during application, comprising adding a lactate ester as a crystallization prevention agent to the composition.
The present invention provides a liquid pesticidal composition comprising one or more pesticide as an active ingredient and a lactate ester as a crystal growth inhibitor.
Detailed Description of the Invention
The following description is illustrative of embodiments of the invention. The following description is not to be construed as limiting, it being understood that the skilled person may carry out many obvious variations to the invention. Tl roughout the description, percentages of components are by weight, unless specifically noted differently. Furthermore, throughout the description "pesticide" refers to insecticides, herbicides, fungicides and mixtures thereof. Throughout the specification the term "azole" or "azole fungicide" also means mixtures thereof.
It has surprisingly been found that esters of lactic acid (LA) are effective as crystal growth inhibitor in liquid pesticidal compositions. Throughout the description wherein the term lactic acid, lactate esters and esters of lactic acid are used it is meant to include both optical isomers as well as mixtures thereof. Furthermore, it has surprisingly been found that mixtures of lactate esters with rosin gum, or derivatives thereof selected from among a group comprising of rosin gum, rosin esters, modified rosins, hydro genated rosin esters, polymerized rosin esters and phenolic modified rosin esters or mixtures thereof (hereinafter "Rosin derivatives") prevent the crystallization in the pesticidal composition.
Pesticides suitable for the practice of the present invention may be, but are not limited to azole fungicides selected from among a group comprising of epoxiconazole, tebuconazole, cyproconazole, prochloraz, penconazole, defenoconazole, flusilazole, metconazole, triadimenol, hexaconazole, flutriafol, triflumizole, fenbuconazole, bromuconazole, fluquinconazole, azaconazole, triticonazole, triadimefon and imibenconazole; strobilurin analogues, e.g. kresoxim-methyl and pyraclostrobin; maneb, mancozeb, ziram, thiram and mixtures thereof.
According to a particular aspect the present invention there is provided a method for preventing crystallization of pesticidal compositions during application, comprising adding a lactate ester or a mixture of lactate esters as a crystallization prevention agent to the composition. In the present context the term "prevention" of crystallization also encompasses "inhibition" of crystallization. The lactate ester is added to a pesticidal composition so that the lactate ester is 3% to 80% of the total composition, preferably 20% to 60%. According to yet a further embodiment, a lactate ester is added to a pesticidal composition so that the weight ratio between the pesticide and the lactate ester is from 1:0.2 to 1:5, preferably 1:1 to 1:4. Throughout the description the term lactate ester also encompasses mixtures of lactate esters.
According to yet a further embodiment a mixture of LA ester and a Rosin derivative are added as a crystallization prevention agent. The LA ester is added according to the aforementioned percentages or ratios. A Rosin derivative is added to a pesticidal composition so that the Rosin derivative is 0.5%0 to 20% of the total pesticidal composition, preferably 1% to 10%>. According to a further embodiment a Rosin derivative may be added so that the weight ratio between the Rosin derivative and the pesticide is from 1:0.05 to 1:1, preferably 1:0.1 to 1:0.5.
According to a preferred embodiment of the present invention, the preferred lactate esters for the practice of the invention are lactate acid esters of C4 to C12 saturated and unsaturated alkyl, C4 to C12 saturated and unsaturated cyclically, C4 to C12 saturated and unsaturated branched alkyl lactates and mixtures thereof. Particularly preferable lactate esters are 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof. The preferred Rosin derivative is rosin gum.
In a particular embodiment of the invention a lactate ester is added to a pesticidal composition in order to prevent crystallization during application, wherein the pesticidal composition contains, subsequent to the addition, 3% to 80%, preferably 10% to 50% of a pesticide selected from among a group comprising of tebuconazole, epoxiconazole and prochloraz and 3% to 80%, preferably 20% to 60% lactate ester selected from among a group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof.
hi yet a further particular embodiment of the invention a lactate ester and Rosin derivative are added to a pesticidal composition in order to prevent crystallization during application, wherein the pesticidal composition contains, subsequent to the addition, 3% to 80% , preferably 10% to 50% of a pesticide selected from among a group comprising of tebuconazole, epoxiconazole and prochloraz 3% to 80%, preferably 20% to 60% lactate ester selected from among a group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof, and 0.5% to 20%, preferably 1%> to 10% of a Rosin derivative selected from among a group comprising of rosin gum, rosin esters, modified rosins, hydrogenated rosin esters, polymerized rosin esters and phenolic modified rosin esters.
The present invention further provides a pesticidal composition which does not crystallize during application. Said composition comprising a pesticide or mixture of pesticides as active ingredient and a lactate ester. The composition comprising 3% to 80%, preferably 10% to 50% of a pesticide or mixture of pesticides and 3% to 80%>, preferably 20%o to 60% lactate ester. According to a further embodiment of the invention a pesticidal composition which does not crystallize during application comprises 3% to 80%, preferably 10% to 50% of a pesticide or mixture of pesticides, 3% to 80%, preferably 20% to 60% lactate ester and 0.5% to 20%, preferably 1% to 10% of a Rosin derivative.
According to a preferred embodiment of the invention, the present compositions comprise 10% to 50% pesticide selected from among a group comprising of tebuconazole, epoxiconazole and prochloraz, 20% to 60% of lactate ester selected from among a group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof, and 0.5% to 20% of a Rosin derivative selected from among a group comprising of rosin gum, and methyl ester of rosin gum.
Compositions according to the present invention may further contain surfactant agents, thickeners, anti-foaming agents, dispersing agents and wetting agents.
1% to 40% of the present composition may be surfactant agents wherein non-limiting examples of suitable surface-active compounds are nonionic, cationic and/or anionic surfactants having good emulsifying, dispersing and wetting properties. The term "surfactants" will also be understood as comprising mixtures of surfactants. T IL03/00222
-6-
Suitable anionic surfactants can be both water-soluble soaps and water-soluble synthetic surface-active compounds. Suitable soaps are the alkali metal salts, alkaline earth metal salts or unsubstituted or substituted ammonium salts of higher fatty acids (C10 -C22), e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained, e.g. from coconut oil or tallow oil. Further suitable surfactants are also the fatty acid methyltaurin salts as well as modified and unmodified phospholipids.
More frequently, however, so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
The fatty sulfonates or sulfates are usually in the form of alkali metal salts, alkali earth metal salts or unsubstituted or substituted ammonium salts and contain a C8 -C22 alkyl radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of lignosulfonic acid, of dodecylsulfate, or of a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also comprise the salts of sulfuric acid esters and sulfonic acids of fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonic acid/formaldehyde condensation product. Also suitable are corresponding phosphates, e.g. salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 moles of ethylene oxide.
Non-ionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, or saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols.
Further suitable non-ionic surfactants are the water-soluble adducts of polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which adducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit.
Representative examples of non-ionic surfactants are nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, polyethylene glycol and octylphenoxypolyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan, e.g. polyoxyethylene sorbitan trioleate, are also suitable non-ionic surfactants.
Cationic surfactants are preferably quaternary ammonium salts which contain, as N-substituent, at least one C8 -C22 alkyl radical and, as further substituents, unsubstituted or halogenated lower alkyl, benzyl or hydroxy-lower alkyl radicals. The salts are preferably in the form of halides, methylsulfates or ethylsulfates, e.g. stearyltrimethylammonium chloride or benzyldi (2-chloroethyl) ethylammonium bromide, preferably 1% to 40%.
Anti-foaming agents (AF) suitable for use in the present composition are those customarily employed in pesticidal compositions, wherein non-limiting examples of said agents are silicon oils or silicon oil emulsions in water commercially available as, e.g., Dapro DF-1161, wherein 0% to 1% of anti-foaming agent are employed, preferably 0% to 0.2%.
According to a particular aspect of the present invention, the compositions of the present invention can be either aqueous or non-aqueous compositions which contain 0% to 50%> water. Non-limiting examples of such compositions are: emulsifiable concentrates (EC) and emulsion in water (EW) formulations. 00222
-8-
Examples
Example 1: Non-crystallizing formulation of tebuconazole
Composition tebuconazole tech. - 200 kg. (204 kg. as 98%)
Berol 8291 - 110 kg.
Emcol 45002 - 50 kg. rosin Gum - 30 kg. Soft water - 15 kg.
AF 100% (DF-1161)3 - 0.1 kg.
Purasolve EHL(2-ethyl hexyl lactate) - up to 1000 liters (about 580 kg.)
1 Berol 829 - Castor oil ethoxylated 20 ethylene oxide (EO) 2 Emcol 4500 - Na dioctyl sulfosuccinate
3 Anti-foaming - Dapro DF-1161 produced by Daniel products company, NJ
Preparation:
Charge the Purasolve to the vessel and heat to 50 - 60°C. Add the tebuconazole and rosin gum and mix until homogenous solution is obtained. Cool to ambient temp, and add the Berol, Emcol and AF and mix until homogenous solution is obtained. Add the water, mix for another hour.
Example 2: Comparative preparation without crystallization inhibitors
tebuconazole tech. - 200 kg. (204 kg. as 98%)
Suprofor 14/ R (ethoxylated castor oil) - 90 kg.
Witconol NS 500 LQ (EO/POblockcc-polymer) - 80 kg. rosin Gum - 160 kg. Soft water - 25 kg.
AF 100% (DF-1161) - 0.1 kg.
NMP (N-Methyl Pyrrolydone) - up to 1000 liters This formulation was found to crystallize during application.
Example 3: Formulation of prochloraz
Composition prochloraz tech. 450 kg. (464 kg. As 97%) Rosin Gum 30 kg. Berol 829 140 kg. Emcol 4500 60 kg. Purasolve EHL up to 1000 litre (about 410 kg.)
Example 4: Formulation of a mixture of prochloraz and tebuconazole
Composition Tebuconazole tech. 133 kg (136 kg. as 98%) Prochloraz tech. 267 kg (281 kg. as 95%) Emulan EL4 160 kg. Emcol 4500 40 kg Soft water 15 kg. AF 100% (DF-1161) 0.1 kg. Purasolve EHL up to 1000 liters (about 440 kg.)
4 Emulan EL - Castor oil ethoxylated
Test of crystal growth inhibition
The formation of crystals in spraying solutions is determined in various conditions in order to assure no crystal formation in various spraying conditions.
10 liters of spraying solutions are prepared using hard water (CIPAC standard water D, 342 ppm) in 3 different concentrations: 0.5, 1, 2 times the recommended spraying concentration for each formulation. Each sample is placed at 3 different temperatures: 2°C, 15°C and 30°C for 24 hours to allow crystal growth. The solutions are sprayed using a personal spraying machine and using two filters (~8 gr. each): 100 and 50 mesh. After spraying the filters are dried and weighed. A weight difference of the filter before and after spraying of less than 0.05 gr. indicates essentially no crystal growth. Hence, there will not be filter blocking.
While embodiments of the invention have been described by way of illustration, it will be apparent that the invention may be carried out with many modifications, variations and adaptations, without departing from its spirit or exceeding the scope of the claims.

Claims

1. A method for preventing crystallization of pesticidal compositions during application, comprising adding a lactate ester as a crystallization prevention agent to the composition.
2. A method according to claim 1 wherein the lactic acid ester is selected from among a group comprising of C4 to C12 saturated and unsaturated alkyl, C4 to C12 saturated and unsaturated cycloalkyl and C4 to C12 saturated and unsaturated branched alkyl lactates and mixtures thereof.
3. A method according to claim 2 wherein the lactate ester is selected from among a group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof.
4. A method according to claim 1 wherein the lactate ester is added to a pesticidal composition so that the lactate ester is 3%> to 80% of the total composition.
5. A method according to claim 4 wherein the lactate ester is added to a pesticidal composition so that the lactate ester is 20% to 60% of the total composition.
6. A method according to claim 1 wherein a lactate ester is added to a pesticidal composition so that the weight ratio between the pesticide and the lactate ester is from 1:0.1 to 1:5.
7. A method according to claim 6 wherein a lactate ester is added to a pesticidal composition so that the weight ratio between the pesticide and the lactate ester is
Figure imgf000013_0001
8. A method according to any one of claims 1 to 7 wherein a rosin derivative is further added.
9. A method according to claim 8 wherein the rosin derivative is selected from among a group comprising of rosin gum, rosin esters, modified rosins, hydrogenated rosin esters, polymerized rosin esters and phenolic modified rosin esters or mixtures thereof.
10. A method according to claim 8 wherein the Rosin derivative is added so that the Rosin derivative is 0.5% to 20% of the total pesticidal composition.
11. A method according to claim 10 wherein the Rosin derivative is added so that the Rosin derivative is 1% to 10% of the total pesticidal composition.
12. A method according to claim 8 wherein the Rosin derivative may be added so that the weight ratio between the Rosin derivative and the pesticide is from 1:0.05 to 1:1.
13. A method according to claim 12 wherein the Rosin derivative may be added so that the weight ratio between the Rosin derivative and the pesticide is from 1:0.1 to 1:0.5.
14. A method according to any one of claims 1 to 13 wherein the pesticidal compositions contains as an active ingredient a pesticide selected from among a group comprising of epoxiconazole, tebuconazole, cyproconazole, prochloraz, penconazole, defenoconazole, flusilazole, metconazole, triadimenol, hexaconazole, flutriafol, triflumizole, fenbuconazole, bromuconazole, fluquinconazole, azaconazole, triticonazole, triadimefon and imibenconazole; strobilurin analogues, maneb, mancozeb, ziram, thiram and mixtures thereof.
15. A liquid pesticidal composition comprising one or more pesticide as an active ingredient and a lactate ester as a crystal growth inhibitor.
16. A composition according to claim 15 wherein the lactate ester is selected from among a group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2- methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof.
17. A composition according to claim 15 further comprising a Rosin derivative.
18. A composition according to claim 17 wherein the Rosin derivative is selected from among a group comprising of rosin gum, rosin esters, modified rosins, hydrogenated rosin esters, polymerized rosin esters and phenolic modified rosin esters or mixtures thereof.
19. A composition according to any of claims 15 and 17 wherein the pesticide is selected from among a group comprising of epoxiconazole, tebuconazole, cyproconazole, prochloraz, penconazole, defenoconazole, flusilazole, metconazole, triadimenol, hexaconazole, flutriafol, triflumizole, fenbuconazole, bromuconazole, fluquinconazole, azaconazole, triticonazole, triadimefon and imibenconazole; strobilurin analogues, maneb, mancozeb, ziram, thiram and mixtures thereof.
20. A composition according to claim 15 comprising 3% to 80% lactate ester.
21. A composition according to claim 20 comprising 1% to 10% Rosin derivative.
22. A composition according to claim 15 wherein the weight ratio between the pesticide and the lactate ester is from 1 :0.1 to 1 :5.
23. A composition according to claim 17 wherein the weight ratio between the pesticide and the Rosin derivative is from 1 :0.05 to 1 : 1
24. A composition according to claim 17 comprising 1% to 10% Rosin derivative. A composition according to claim 17 comprising 20% to 60% of a lactate ester selected from among a group comprising of 2-ethyl hexyl lactate, cyclohexyl lactate, 2-methylcyclohexyl lactate, heptyl lactate, octyl lactate and mixtures thereof and 1% to 10 % of rosin gum.
A method as herein described and exemplified.
A composition as herein described and exemplified.
PCT/IL2003/000222 2002-03-14 2003-03-13 Pesticidal composition comprising a lactate ester as crystal growth inhibitor WO2003075657A1 (en)

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SI200331318T SI1482790T1 (en) 2002-03-14 2003-03-13 Pesticidal composition comprising a lactate ester as crystal growth inhibitor
DK03710187T DK1482790T3 (en) 2002-03-14 2003-03-13 Pesticide composition comprising a lactate ester as a crystal growth inhibitor
YUP-809/04A RS80904A (en) 2002-03-14 2003-03-13 Pesticidal compositions comprising a lactave ester as crystal growth inhibitor
MXPA04008923 MX243369B (en) 2002-03-14 2003-03-13 PESTICIDE COMPOSITION THAT INCLUDES A LACTATE ESTER AS A GLASS GROWTH INHIBITOR.
KR1020047014426A KR101058816B1 (en) 2002-03-14 2003-03-13 Insecticidal compositions comprising lactate esters as crystal growth inhibitors
CA2479053A CA2479053C (en) 2002-03-14 2003-03-13 Pesticidal composition comprising a lactate ester as crystal growth inhibitor
APAP/P/2004/003139A AP2004003139A0 (en) 2002-03-14 2003-03-13 Pesticidal composition comprising a lactate ester as crystal growth inhibitor
EP03710187A EP1482790B8 (en) 2002-03-14 2003-03-13 Pesticidal composition comprising a lactate ester as crystal growth inhibitor
EA200401079A EA007031B1 (en) 2002-03-14 2003-03-13 Pesticidal composition comprising a lactate ester as crystal growth inhibitor
NZ535303A NZ535303A (en) 2002-03-14 2003-03-13 Pesticidal composition comprising a lactate ester as crystal growth inhibitor
BRPI0308455A BR0308455B1 (en) 2002-03-14 2003-03-13 method for preventing crystallization of pesticidal compositions during application and liquid pesticidal composition of emulsifying concentrates (ec) or an emulsion in water (ew)
AU2003214607A AU2003214607B2 (en) 2002-03-14 2003-03-13 Pesticidal composition comprising a lactate ester as crystal growth inhibitor
JP2003573944A JP4657607B2 (en) 2002-03-14 2003-03-13 Agrochemical composition containing lactic acid ester as crystal growth inhibitor
US10/507,103 US20050169951A1 (en) 2002-03-14 2003-03-13 Pesticidal composition comprising a lactate ester as crystal growth inhibitor
DE60322676T DE60322676D1 (en) 2002-03-14 2003-03-13 PESTICIDE COMPOSITION CONTAINING A LACTATE ESTER AS CRYSTAL GROWTH INHIBITOR
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005074685A1 (en) * 2004-02-06 2005-08-18 Bayer Cropscience Gmbh Plant protection compositions and use thereof
WO2007028538A2 (en) 2005-09-09 2007-03-15 Bayer Cropscience Aktiengesellschaft Use of lactate esters for improving the action of agricultural pesticides
WO2007036585A3 (en) * 2005-09-26 2007-05-18 Gat Formulation Gmbh Pesticide formulations which risk crystallisation and process for producing the same
WO2008128666A2 (en) * 2007-04-21 2008-10-30 Cognis Ip Management Gmbh Agrochemical preparations
JP2008540471A (en) * 2005-05-13 2008-11-20 ランクセス・ドイチュランド・ゲーエムベーハー Fungicidal mixture
WO2011012493A2 (en) 2009-07-28 2011-02-03 Basf Se Pesticidal suspo-emulsion compositions
EP2292092A1 (en) 2009-09-02 2011-03-09 Cognis IP Management GmbH Biocide compositions comprising esters of ketocarboxylic acids
WO2011098419A2 (en) 2010-02-12 2011-08-18 Basf Se Anhydrous composition comprising a dissolved pesticide and a suspended pesticide, alkyl lactate and alcohol
EP2387886A1 (en) * 2010-05-18 2011-11-23 Cognis IP Management GmbH Biocide compositions comprising isoamyl lactate
WO2013014126A1 (en) 2011-07-26 2013-01-31 Bayer Intellectual Property Gmbh Etherified lactate esters, method for the production thereof and use thereof for enhancing the effect of plant protecting agents
US20130172188A1 (en) * 2010-08-17 2013-07-04 Rotam Agrochem International Co.,Ltd Herbicidal compositions
WO2017108662A1 (en) * 2015-12-22 2017-06-29 Bayer Cropscience Aktiengesellschaft Emulsion concentrates of lipophilic compounds

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060171978A1 (en) 2005-01-28 2006-08-03 Lopes John A Disinfecting and antimicrobial compositions
MX2008013846A (en) * 2006-04-28 2009-01-20 Summit Vetpharm Llc High concentration topical insecticides containing pyrethroids.
AR062587A1 (en) * 2006-08-30 2008-11-19 Dow Agrosciences Llc AGRICOLALLY USEFUL COMPOSITIONS
MX2010011950A (en) * 2008-04-30 2010-12-01 Valent Usa Corp Novel pyriproxyfen compositions.
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WO2011037968A1 (en) * 2009-09-22 2011-03-31 Valent U.S.A, Corporation Metconazole compositions and methods of use
AU2015201945B2 (en) * 2010-03-12 2017-03-16 Monsanto Technology Llc Plant health compositions comprising a water-soluble pesticide and a water-insoluble agrochemical
MX352352B (en) * 2010-03-12 2017-11-21 Monsanto Technology Llc Plant health compositions comprising a water-soluble pesticide and a water-insoluble agrochemical.
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AR093942A1 (en) * 2012-12-19 2015-07-01 Akzo Nobel Chemicals Int Bv COMPOSITIONS AND METHODS TO IMPROVE THE COMPATIBILITY OF HERBICIDE SALTS SOLUBLE IN WATER AND CONCENTRATED FERTILIZER

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0357559A2 (en) * 1988-09-02 1990-03-07 AgrEvo UK Limited Aqueous formulations and their use
JPH02108602A (en) * 1988-10-19 1990-04-20 Toho Chem Ind Co Ltd Stable oil-in-water type emulsified agricultural chemical composition
WO1993015605A2 (en) * 1992-02-18 1993-08-19 Agrevo Uk Limited Liquid pesticidal formulations
WO2000018227A1 (en) * 1998-09-25 2000-04-06 American Cyanamid Company Non-aqueous suspension concentrate

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3247050A1 (en) * 1982-12-20 1984-06-20 Bayer Ag, 5090 Leverkusen HERBICIDAL AGENTS
DE3910921C1 (en) * 1989-04-05 1990-05-17 Bayer Ag, 5090 Leverkusen, De
DE4013522A1 (en) * 1990-04-27 1991-10-31 Bayer Ag USE OF ALKYLCARBONIC ACID DIMETHYLAMIDES AS CRYSTALLIZATION INHIBITORS
DE69132334T2 (en) * 1990-05-18 2000-11-30 Agriculture Victoria Serv Pty COMPOSITION WITH CONTROLLED ACTIVE SUBSTANCE DELIVERY OF A BIOCID IN AN AQUEOUS DISPERSION OF A VISCOSE OIL
JPH05178763A (en) * 1991-02-19 1993-07-20 Nippon Saafuakutanto Kogyo Kk Resolvent composition for sparingly soluble medicine
US5531995A (en) * 1992-10-29 1996-07-02 Makhteshim Chemical Works Ltd. Low ecotoxic formulations of pesticides
JPH07165515A (en) * 1993-10-21 1995-06-27 Mitsubishi Chem Corp Solid agrochemical composition
JPH07278459A (en) * 1994-04-08 1995-10-24 Toyo Ink Mfg Co Ltd Monoazo lake pigment composition and gravure ink
JPH0826907A (en) * 1994-07-04 1996-01-30 Makhteshim Chem Works Ltd Low environmentally noxious emulsifiable concentrated agricultural chemical preparation
JPH0826906A (en) * 1994-07-04 1996-01-30 Makhteshim Chem Works Ltd Low environmentally noxious agricultural chemical preparation
BR9807396A (en) * 1997-02-18 2000-03-14 Sumitomo Chemical Co Herbicidal composition
US6165940A (en) * 1998-09-25 2000-12-26 American Cyanamid Co. Non-aqueous suspension concentrate
JP2000119103A (en) * 1998-10-12 2000-04-25 Fumakilla Ltd Aqueous and suspended insecticidal composition
BR9916268A (en) * 1998-12-17 2001-09-04 Syngenta Participations Ag Pesticide concentrates in aqueous suspension
JP3524445B2 (en) * 1999-09-17 2004-05-10 カネボウ株式会社 Freshener composition
EP1210877A1 (en) * 2000-12-01 2002-06-05 Aventis CropScience GmbH Oil-in-water emulsion formulation of insecticides
US20040253287A1 (en) * 2002-08-03 2004-12-16 Denton Robert Michael Environmentally safe insecticides
US20060199736A1 (en) * 2002-12-16 2006-09-07 Vertec Biosolvents, Inc. Environmentally benign bioactive formulation
AU2005336297B2 (en) * 2005-09-05 2010-11-11 Cheminova A/S Concentrated liquid triazole-fungicide formulations
DE102005042876A1 (en) * 2005-09-09 2007-03-22 Bayer Cropscience Ag Use of lactate esters to improve the effect of pesticides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0357559A2 (en) * 1988-09-02 1990-03-07 AgrEvo UK Limited Aqueous formulations and their use
JPH02108602A (en) * 1988-10-19 1990-04-20 Toho Chem Ind Co Ltd Stable oil-in-water type emulsified agricultural chemical composition
WO1993015605A2 (en) * 1992-02-18 1993-08-19 Agrevo Uk Limited Liquid pesticidal formulations
WO2000018227A1 (en) * 1998-09-25 2000-04-06 American Cyanamid Company Non-aqueous suspension concentrate

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 014, no. 314 (C - 0737) 5 July 1990 (1990-07-05) *
WATLING H: "Gibbsite crystallization inhibition - 2. Comparative effects of selected alditols and hydroxycarboxylic acids", HYDROMETALLURGY, ELSEVIER SCIENTIFIC PUBLISHING CY. AMSTERDAM, NL, vol. 55, no. 3, April 2000 (2000-04-01), pages 289 - 309, XP004196083, ISSN: 0304-386X *

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007520511A (en) * 2004-02-06 2007-07-26 バイエル クロップサイエンス ゲーエムベーハー Plant protection composition and use thereof
WO2005074685A1 (en) * 2004-02-06 2005-08-18 Bayer Cropscience Gmbh Plant protection compositions and use thereof
JP2008540471A (en) * 2005-05-13 2008-11-20 ランクセス・ドイチュランド・ゲーエムベーハー Fungicidal mixture
JP4685931B2 (en) * 2005-05-13 2011-05-18 ランクセス・ドイチュランド・ゲーエムベーハー Fungicidal mixture
EP1926369B1 (en) 2005-09-09 2015-06-17 Bayer Intellectual Property GmbH Use of lactate esters for improving the action of agricultural pesticides
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EA014782B1 (en) * 2005-09-09 2011-02-28 Байер Кропсайенс Аг Use of lactate esters for improving the action of agricultural pesticides, a method for improving pesticide activity
AU2006289348B2 (en) * 2005-09-09 2011-04-21 Bayer Intellectual Property Gmbh Use of lactate esters for improving the action of agricultural pesticides
ES2288093A1 (en) * 2005-09-26 2007-12-16 Gat Formulation Gmbh Pesticide formulations which risk crystallisation and process for producing the same
WO2007036585A3 (en) * 2005-09-26 2007-05-18 Gat Formulation Gmbh Pesticide formulations which risk crystallisation and process for producing the same
EA015417B9 (en) * 2005-09-26 2012-01-30 Байер Кропсайенс Аг Pesticide formulations which risk crystallisation and process for producing the same
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WO2008128666A3 (en) * 2007-04-21 2009-09-24 Cognis Ip Management Gmbh Agrochemical preparations
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US8728978B2 (en) 2009-09-02 2014-05-20 Cognis Ip Management Gmbh Biocide compositions (IV)
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