WO1999026473A1 - Composes d'inclusion contenant des hydrates de carbone modifies et des principes actifs agrochimiques - Google Patents

Composes d'inclusion contenant des hydrates de carbone modifies et des principes actifs agrochimiques Download PDF

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Publication number
WO1999026473A1
WO1999026473A1 PCT/EP1998/007196 EP9807196W WO9926473A1 WO 1999026473 A1 WO1999026473 A1 WO 1999026473A1 EP 9807196 W EP9807196 W EP 9807196W WO 9926473 A1 WO9926473 A1 WO 9926473A1
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WIPO (PCT)
Prior art keywords
formula
inclusion complexes
stand
integers
complexes according
Prior art date
Application number
PCT/EP1998/007196
Other languages
German (de)
English (en)
Inventor
Günter WULFF
Andreas Konrad Steinert
Wolfram Andersch
Klaus Stenzel
Jürgen HÖLTERS
Uwe Priesnitz
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU18719/99A priority Critical patent/AU1871999A/en
Publication of WO1999026473A1 publication Critical patent/WO1999026473A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • 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
    • A01N25/08—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 solids as carriers or diluents
    • A01N25/10—Macromolecular 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • the present invention relates to new inclusion complexes of modified carbohydrates and agrochemical active substances, a process for the preparation of the new complexes and their use for the application of agrochemical active substances.
  • R 1 , R 2 and R 3 represent hydrogen or a radical of the formula -CH-CH 2 -OH, -CH, -CH-OH. -CH 2 -CH-CH 2 OH - -C-CH-
  • R 2 also for a glucose chain of the formula
  • n integers from 10 to 10,000
  • inclusion complexes according to the invention can be prepared by
  • inclusion complexes according to the invention are very suitable as plant treatment agents.
  • the inclusion complexes according to the invention show a considerably better activity in the treatment of plants than complexes of natural starch and agrochemical active substances, which are the most similar, known preparations of the same direction of action.
  • inclusion complexes according to the invention as plant treatment agents is associated with a number of advantages. So are the agrochemical
  • Active substances in the complexed form are more stable against photochemical degradation and oxidative decomposition than in the non-complexed form.
  • an increase in effectiveness is achieved in comparison to the non-complexed preparations.
  • the substances according to the invention are inclusion complexes of modified carbohydrates of the formula (I) and agrochemical active substances.
  • modified carbohydrates preference is given to compounds of the formula (I) in which
  • R 1 , R 2 and R 3 represent hydrogen or a radical of the formula
  • R 2 also for a glucose chain of the formula
  • m stands for integers from 100 to 10,000.
  • a particularly preferred group of compounds of formula (I) are modified amyloses. This includes carbohydrates of the formula (I) in which
  • R 1 , R 2 and R 3 represent hydrogen or a radical of the formula
  • R 2 also for a glucose chain of the formula
  • n stands for integers from 0 to 500
  • n represents integers from 500 to 5,000.
  • Another group of particularly preferred compounds of the formula (I) are modified maltodextrins.
  • This includes carbohydrates of the formula (I) in which R 1 , R 2 and R 3 represent hydrogen or a radical of the formula
  • R 2 also for a glucose chain of the formula
  • n stands for integers from 0 to 500
  • n represents integers from 10 to 1,000.
  • the degree of substitution that is to say the proportion of those groups in which R 1 , R 2 and R 3 are different from hydrogen, is between 0.05 and 100%. Such compounds with low degrees of substitution are preferred. Modified carbohydrates of the form are particularly preferred. mel (I), in which on 2 to 30 glucose units only one of the radicals R 1 , R 2 and R 3 is not hydrogen.
  • m stands for 900 on average
  • m stands for 900 on average
  • m stands for 900 on average
  • radicals R 1 , R 2 and R 3 represent -CH, -CH-CH, -OH.
  • Modified maltodextrin from potatoes i.e. a compound of formula (I) in which m stands for 50 on average and
  • the modified carbohydrates of the formula (I) are known or can be prepared by known methods (cf. Makromol. Chem.. [93, 1071-1080 (1992)).
  • agrochemical active ingredients are all for
  • Fungicides Fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, plant growth regulators and plant nutrients may preferably be mentioned.
  • fungicides are:
  • Imazalil Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodion, Isoprothiolan, Kasugamycin
  • copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
  • Mancopper Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol,
  • Nickel dimethyldithiocarbamate Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxycarboxin,
  • Probenazole prochloraz, procymidone, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilone,
  • PCNB Quintozen
  • Tebuconazole Tecloftalam, Technazen, Tetraconazole, Thiabendazole, Thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadimenol,
  • Triazoxide trichlamide, tricyclazole, tridemorph, triflumizole, triforin, triticonazole,
  • bactericides are:
  • insecticides examples include acaricides and nematicides.
  • Bacillus thuringiensis 4-bromo-2- (4-chlorophenyl) -1 - (ethoxymethyl) -5- (trifluoromethyl) -lH-pyrrole-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, brofenprox , Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloetho- carb, Chloretoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, N - [(6-Chlorinyl) - 3-pyrid -methyl] -N'-cyano-N-methyl-ethanimidamide,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flucycloxuron, Flucythrinat, Flufenxurophone, Flufenoxurion, Fufionxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron, Flufenoxuron,
  • Tebufenozide Tebufenpyrad
  • Tebupirimiphos Teflubenzuron
  • Tefluthrin Temefos
  • Terbam Terbufos
  • Tetrachlorvinphos Thiafenox, Thiodicarb, Thiofanox, Thiomethonon, Thionazin, Thuringiensin, Tralomethrinononium, Tralomethrinononium, Transal XMC, xylylcarb, zetamethrin.
  • herbicides are:
  • Anilides e.g. Diflufenican and Propanil
  • Aryl carboxylic acids e.g. Dichloropicolinic acid, dicamba and picloram
  • Aryloxyalkanoic acids e.g. 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr
  • Aryloxy-phenoxy-alkanoic acid esters e.g. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl
  • Azinones e.g.
  • Chloridazon and norflurazon Carbamates, e.g. Chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides, e.g. Alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; Dinitroanilines, e.g. Oryzalin, pendimethalin and trifluralin; Diphenyl ethers, e.g. Acifluorfen, Bifenox, Fluoroglycfen, Fomesafen, Halosafen, Lactofen and Oxyfluorfen; Ureas, e.g.
  • Imazaquin Nitriles, e.g. Bromoxynil, dichlobenil and ioxynil; Oxyacetamides, e.g. Mefenacet; Sulfonylureas, e.g. Amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; Thiol carbamates, e.g. Butylates, cycloates, dialates,
  • EPTC Esprocarb, Molinate, Prosulfocarb, Thiobencarb and Triallate
  • Triazines e.g. Atrazin, cyanazin, simazin, simetryne, terbutryne and terbutylazin
  • Triazinones such as Hexazinone, metamitron and metribuzin
  • Others such as Aminotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clopyralid, Difenzoquat, Dithiopyr, Ethofumesate, Fluorochloridone, Glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tridiphane.
  • Chlorcholine chloride and ethephon are examples of plant growth regulators.
  • Examples of plant nutrients are customary inorganic or organic fertilizers for supplying plants with macro and / or micronutrients.
  • inclusion complexes according to the invention contain one or more agrochemical active substances.
  • the molar proportion of agrochemical active ingredients can be varied within a relatively wide range. In general, 0.01 to 1.0 mol, preferably 0.01 to 0.1 mol, of one or more agrochemical active ingredients are contained per mole of anhydroglucose units.
  • reaction temperatures can be carried out when carrying out the process according to the invention.
  • Procedure can be varied within a certain range. In general, temperatures between 10 ° C and 100 ° C, preferably at reflux temperature.
  • the process according to the invention is generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure.
  • the starting components are used in such amounts that generally 0.1 to 1 mol, preferably 0.15 to 0.5 mol, of one or more per mole of anhydroglucose unit agrochemical active ingredients are included.
  • the procedure is such that the components are mixed with one another in any desired order in the presence of water and, if appropriate, a further water-miscible organic diluent.
  • the procedure is preferably such that an aqueous solution or suspension of modified carbohydrate of the formula (I) is heated, then mixed with one or more agrochemical active ingredients, if appropriate dissolved in a water-miscible organic solvent, and then heated.
  • the processing takes place according to usual methods.
  • the procedure is such that any excess agrochemical active ingredient present is filtered off and the desired product is then isolated by freeze-drying.
  • the inclusion complexes according to the invention are very suitable as plant treatment agents. Depending on the agrochemical active ingredients they contain, they can be used as fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, plant growth regulators or to supply plants with nutrients.
  • inclusion complexes according to the invention are well tolerated by plants allows treatment of above-ground parts of plants, of propagation stock and seeds and of
  • inclusion complexes according to the invention can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and in coating compositions for seeds.
  • formulations are made in a known manner, e.g. by mixing the inclusion complexes with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents include aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and the like their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or m
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Solid carrier materials are suitable: for example natural rock powder, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates.
  • Carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
  • Possible emulsifiers and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
  • Alkylaryl polyglycol ethers alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • the following dispergies are possible: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Mineral and vegetable oils can also be used as additives.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc, can be used .
  • the formulations generally contain between 0.1 and 95 percent by weight of inclusion complexes, preferably between 0.5 and 90 percent by weight.
  • inclusion complexes according to the invention can, as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use
  • Solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules can be used. They are used in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to introduce the inclusion complexes themselves or their preparations into the soil. The seeds of the plants can also be treated.
  • the inclusion complexes according to the invention can be used to introduce agrochemical substances into the soil.
  • they are used as depot preparations near the roots of the plants to be treated, e.g. incorporated into the earth in the form of flours, dusts or granules or stuck into the earth as rods, balls, tablets or other shaped bodies.
  • inclusion complexes according to the invention can also be used to treat individual
  • Plants such as Trees.
  • they are preferably introduced into the sap flow of the plants in the form of suitable moldings, such as rods, tablets, plates, foils, tiles, fabrics, strips, rivets, nails, clamps, pins, needles, hollow nails or wires.
  • suitable moldings such as rods, tablets, plates, foils, tiles, fabrics, strips, rivets, nails, clamps, pins, needles, hollow nails or wires.
  • the shaped bodies are either introduced into the cavities produced in the plant or simply into the
  • Plant tissue pressed, pressed or beaten. You can also take it carefully loosened bark or parts of plants are pushed, the bark or parts of plants then serving again for covering.
  • the inclusion complexes according to the invention can also be used for the production of transcuticular formulations.
  • they are applied to the plant surface in the form of paints, film-forming pastes, films, foils or plasters.
  • the inclusion complexes according to the invention can also be in the form of solutions, emulsions or suspensions in the sap flow of plants, e.g. by injection.
  • the application rate of the inclusion complexes according to the invention can be varied within a relatively wide range. It depends on the respective agrochemical active substances and their content in the inclusion complexes.
  • m stands for 900 on average
  • bitertanol 5.5 g of bitertanol are added in 79 ml of water at room temperature with stirring. The resulting mixture is first heated under reflux, then slowly cooled to room temperature with stirring and then intensively stirred for a further 48 hours at room temperature. The reaction mixture is then filtered and the filtrate is freeze-dried. In this way, 7.2 g of an inclusion complex of the above-mentioned modified amylose and bitertanol are obtained. The bitertanol content in this product is 0.15% by weight.
  • m stands for 900 on average
  • OH in 60 ml of water is heated to 70 ° C. with stirring and then filtered hot.
  • 5.0 g of tebuconazole are added to the filtrate at 50 ° C. while stirring.
  • the resulting mixture is first heated under reflux for 30 minutes, then slowly cooled to room temperature with stirring and then shaken for 24 hours at room temperature.
  • the reaction mixture is then filtered and the filtrate is freeze-dried. In this way, 6.5 g of an inclusion complex of the above-mentioned modified starch and tebuconazole are obtained.
  • the content of tebuconazole in this product is 0.12% by weight.
  • m stands for 900 on average
  • radicals R 1 , R 2 and R 3 represent -CH, -CH-CH, -OH,

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne de nouveaux composés d'inclusion contenant A) des hydrates de carbone modifiés de la formule (I) où R?1, R2, R3¿ et m ont la signification donnée dans la description et B) des principes actifs agrochimiques. L'invention concerne également la production de nouveaux composés et leur utilisation comme produits phytosanitaires.
PCT/EP1998/007196 1997-11-21 1998-11-11 Composes d'inclusion contenant des hydrates de carbone modifies et des principes actifs agrochimiques WO1999026473A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU18719/99A AU1871999A (en) 1997-11-21 1998-11-11 Inclusion complexes comprised of modified carbohydrates and agrochemical active ingredients

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19751630.0 1997-11-21
DE1997151630 DE19751630A1 (de) 1997-11-21 1997-11-21 Inklusionskomplexe aus modifizierten Kohlenhydraten und agrochemischen Wirkstoffen

Publications (1)

Publication Number Publication Date
WO1999026473A1 true WO1999026473A1 (fr) 1999-06-03

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AU (1) AU1871999A (fr)
DE (1) DE19751630A1 (fr)
WO (1) WO1999026473A1 (fr)

Cited By (1)

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Publication number Priority date Publication date Assignee Title
WO2008117037A1 (fr) * 2007-03-23 2008-10-02 Syngenta Limited Co-cristaux de propiconazole

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Publication number Priority date Publication date Assignee Title
US6919446B1 (en) 1998-01-20 2005-07-19 Grain Processing Corp. Reduced malto-oligosaccharides
KR100485358B1 (ko) 1998-01-20 2005-04-25 그레인 프로세싱 코포레이션 환원된 말토-올리고사카라이드
US6380379B1 (en) 1999-08-20 2002-04-30 Grain Processing Corporation Derivatized reduced malto-oligosaccharides
US6593469B1 (en) 1999-10-20 2003-07-15 Grain Processing Corporation Compositions including reduced malto-oligosaccharide preserving agents
JP2003512508A (ja) 1999-10-20 2003-04-02 グレイン・プロセッシング・コーポレーシヨン 還元型マルトオリゴサッカリド・クレンジング組成物
US6258749B1 (en) * 2000-02-22 2001-07-10 The Dow Chemical Company Methods for treating plants and enhancing plant growth using polyacylglycosides and/or polyalkylglycosides and formulations for same

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US2876160A (en) * 1954-07-26 1959-03-03 Corn Prod Refining Co Starch matrix material containing imbedded material and process for preparing same
US3092546A (en) * 1962-02-26 1963-06-04 Upjohn Co Antifungal cycloheximide starch inclusion compositions
EP0361163A1 (fr) * 1988-09-14 1990-04-04 L. GIVAUDAN &amp; CIE Société Anonyme Bêta-bromo-bêta-nitrostyrène pour la conservation de systèmes aqueux
WO1994017676A1 (fr) * 1993-02-08 1994-08-18 Eastman James E Hydrolysats d'amidon utilises comme agents sequestrants

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Publication number Priority date Publication date Assignee Title
US2876160A (en) * 1954-07-26 1959-03-03 Corn Prod Refining Co Starch matrix material containing imbedded material and process for preparing same
US3092546A (en) * 1962-02-26 1963-06-04 Upjohn Co Antifungal cycloheximide starch inclusion compositions
EP0361163A1 (fr) * 1988-09-14 1990-04-04 L. GIVAUDAN &amp; CIE Société Anonyme Bêta-bromo-bêta-nitrostyrène pour la conservation de systèmes aqueux
WO1994017676A1 (fr) * 1993-02-08 1994-08-18 Eastman James E Hydrolysats d'amidon utilises comme agents sequestrants

Non-Patent Citations (1)

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Title
GÜNTER WOLFF & STFEAN KUBIK: "Helical amylose complexes with organic complexands, 1 Micorcalorimetric and circular dichroitic investigations", DIE MAKROMOLEKULARE CHEMIE, MACROMOLECULAR CHEMISTRY AND PHYSICS, vol. 193, no. 5, May 1992 (1992-05-01), BASEL, CH;, pages 1071 - 80, XP000268858 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008117037A1 (fr) * 2007-03-23 2008-10-02 Syngenta Limited Co-cristaux de propiconazole
CN101679389B (zh) * 2007-03-23 2012-11-07 先正达有限公司 丙环唑的共晶
US8318789B2 (en) 2007-03-23 2012-11-27 Syngenta Limited Co-crystals of propiconazole

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DE19751630A1 (de) 1999-05-27
AU1871999A (en) 1999-06-15

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