EP1127046A1 - Derives d'acide 2-phenoxyphenylacetique, procede et produits intermediaires pour leur production, leur utilisation et agents les contenant pour la lutte contre des champignons parasites - Google Patents

Derives d'acide 2-phenoxyphenylacetique, procede et produits intermediaires pour leur production, leur utilisation et agents les contenant pour la lutte contre des champignons parasites

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Publication number
EP1127046A1
EP1127046A1 EP99955883A EP99955883A EP1127046A1 EP 1127046 A1 EP1127046 A1 EP 1127046A1 EP 99955883 A EP99955883 A EP 99955883A EP 99955883 A EP99955883 A EP 99955883A EP 1127046 A1 EP1127046 A1 EP 1127046A1
Authority
EP
European Patent Office
Prior art keywords
formula
compounds
alkyl
weight
acid methyl
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Withdrawn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
EP99955883A
Other languages
German (de)
English (en)
Inventor
Wassilios Grammenos
Hubert Sauter
Andreas Gypser
Oliver Cullmann
Markus Gewehr
Bernd Müller
Arne Ptock
Norbert Götz
Roland Götz
Thorsten Volk
Eberhard Ammermann
Thomas Grote
Gisela Lorenz
Siegfried Strathmann
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
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 BASF SE filed Critical BASF SE
Publication of EP1127046A1 publication Critical patent/EP1127046A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids

Definitions

  • the present invention relates to 2-phenoxyphenylacetic acid derivatives of the formula I,
  • R a is hydrogen or -CC 4 alkyl
  • n 1, 2, 3 or 4 where the groups R 1 can be different if n is not 1;
  • R 2 is halogen, CH 3 or CF 3 ;
  • the invention relates to processes and intermediates for the preparation of the compounds I and the use of the compounds I for controlling harmful fungi.
  • 2-phenoxyphenylacetic acid esters are known from EP-A 253 213 and EP-A 254 426, and such amides are described in EP-A 398 692 and EP-A 477 631.
  • the compounds described in the abovementioned documents are suitable as crop protection agents against harmful fungi. However, their effect is unsatisfactory in many cases.
  • the compounds of the formula I differ from the compounds known from the abovementioned publications in the specific embodiment of the substitution on the 2-phenoxy radical by a substituted phenyl ring in the meta or para position and, if appropriate, a further substituent in the meta or para position.
  • the compounds of the formula I can be obtained per se by the processes described in EP-A 253 213, EP-A 254 426, EP-A 398 692 and EP-A 477 631.
  • the compounds of the formula I are obtained by reacting alkyl ⁇ -phenyl- ⁇ -ketoacetic acid of the formula II under basic conditions with phenols of the formula III to give alkyl ⁇ - (2-phenoxyphenyl) - ⁇ -ketoacetic acid of the formula IV.
  • L represents a leaving group customary for nucleophilic aromatic substitution, such as halogen, in particular fluorine or chlorine, or sulfonate or nitro. This reaction takes place under generally customary conditions analogous to WO-A 97/24317.
  • Keto esters IV are reacted with O-methylhydroxylamine or its acid addition salt of the formula Va, optionally in the presence of a base, to give oxime ethers of the formula IA under the conditions described in EP-A 493 711.
  • Q stands for the anion of an inorganic acid, in particular a halide ion.
  • Phenols of the formula III are known from the literature or can be obtained by methods known from the literature [cf. WO-A 96/23749;
  • the compounds of the formula I can also be obtained by the process known from WO-A 95/34526.
  • compounds of the formula I can also be prepared from compounds of the formula VI by transition-catalyzed coupling with a phenyl derivative of the formula VII.
  • M represents an organometallic residue, such as, for example, B (OH) 2 , Sn (CH 3 ) 3 , Sn (nC 4 H 9 ) 3 , Mg-Hal or Zn-Hal.
  • “shark” represents a halogen atom, such as chlorine, bromine or iodine, especially bromine and iodine.
  • the reaction of VI with VII usually takes place at temperatures from 10 ° C. to 150 ° C., preferably 50 ° C. to 120 ° C., in an inert organic solvent [cf. WO-A 98/11070; Synth. Commun. P. 513 (1981); Appl. Chem. Ind. Ed. P. 508 (1986)].
  • M in formula VII is B (OH) 2 , it is carried out in the presence of a base [cf. Synth. Commun. P. 513 (1981); ibid. p. 709 (1994); J. Het. Chem. P. 865 (1989); J. Org. Chem. P. 2052 (1988); ibid. p. 6095 (1994)].
  • Suitable solvents are ethers, such as dioxane, dimethoxyethane and tetrahydrofuran. Mixtures of the solvents mentioned can also be used.
  • Bases suitable for the Suzuki reaction are, for example, potassium carbonate, sodium carbonate, sodium hydrogen carbonate and triethylamine.
  • Suitable catalysts are: trans-bis (acetonitrile) palladium (II) chloride, bis (dibenzylidene acetone) palladium (0), bis (triphenylphosphine) palladium (II) chloride, palladium acetate, palladium chloride and Tetrakis (triphenylphosphine) palladium (0).
  • the compounds of formula VI are from EP-A 253 213, EP-A
  • the reaction mixtures are worked up in a conventional manner, e.g. by mixing with water, separating the phases and, if necessary, chromatographically cleaning the raw products.
  • the intermediate and end products fall partly in the form of colorless or slightly brownish, viscous oils, which are freed from volatile components or purified under reduced pressure and at a moderately elevated temperature. If the intermediate and end products are obtained as solids, they can also be purified by recrystallization or digesting.
  • Double bonds are obtained as E / Z isomer mixtures, e.g. can be separated into the individual compounds by crystallization or chromatography in the usual way.
  • isomer mixtures are obtained in the synthesis, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (for example under the action of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus to be combated.
  • the E isomers of the compounds I are preferred in terms of their activity (configuration based on the OCH 3 group in relation to the COX group).
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals with 1 to 4 carbon atoms, for example C 1 -C 4 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1, 1- Dimethylethyl;
  • Haloalkyl straight-chain or branched alkyl groups with 1 to 4 carbon atoms (as mentioned above), it being possible for part or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, bromomethyl, dichloroethyl, Trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-di-fluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro 2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichlor
  • Alkoxy straight-chain or branched alkyl groups with 1 to 4 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (-0-);
  • Haloalkoxy straight-chain or branched haloalkyl groups with 1 to 4 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (-0-);
  • Alkylamino a straight-chain or branched alkyl group with 1 to 4 carbon atoms (as mentioned above) which is bonded to the skeleton via an amino group (-NH-);
  • Dialkylamino two independent, straight-chain or branched alkyl groups each having 1 to 4 carbon atoms (as mentioned above) which are bonded to the skeleton via a nitrogen atom;
  • Alkoxycarbonyl an alkoxy group with 1 to 4 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group (-CO-);
  • Alkylaminocarbonyl an alkylamino group with 1 to 4 carbon atoms (as mentioned above) which is bonded to the skeleton via a carbonyl group (-CO-);
  • Dialkylaminocarbonyl a dialkylamino group (as mentioned above) which is bonded to the skeleton via a carbonyl group (-C0-);
  • R 1 is halogen, C ⁇ -C 4 alkoxy, CF3, C ⁇ -C4-haloalkoxy, C ⁇ -C nyl 4 -Alkoxycarbo-, C ⁇ -C 4 alkylaminocarbonyl or di- ( C ⁇ -C 4 alkyl) aminocarbonyl.
  • compounds I are preferred in which two groups R 1 are in the 2,4-position.
  • the compounds I are suitable as fungicides. They are characterized by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidio / nycetes, out. Some of them are systemically active and can be used in plant protection as leaf and soil fungicides.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines
  • Erysiphe graminis (powdery mildew) on cereals, Fusarium and Verticillium species on various plants, Helminthosporium species on cereals, Mycosphaerella species on bananas and peanuts, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Podosphaera leucelnicha on
  • Rhizoctonia species on cotton, rice and lawn Septoria nodorum on wheat, Uncinula necator on vines,
  • the compounds I are also suitable for combating harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds.
  • the application can take place both before and after the infection of the materials, plants or seeds by the fungi.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.
  • the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably
  • the compounds I can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as a diluent, other organic solvents can also be used as auxiliary solvents.
  • auxiliaries solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g.
  • Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates)
  • Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid sulfates, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ethers, condensates of sulfonated Naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral soils, such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, do
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • V. 80 parts by weight of a compound according to the invention are mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel well mixed and ground in a hammer mill (active ingredient content 80% by weight).
  • VIII.20 parts by weight of a compound according to the invention are mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene- ⁇ -sulfonic acid, 17 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of pulp.
  • mixed silica gel well mixed and ground in a hammer mill By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
  • the active ingredients as such in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or pouring.
  • the application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
  • emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.
  • the active substance concentrations in the ready-to-use preparations can be varied over a wide range. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume process
  • Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
  • the compositions according to the invention can also be present together with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers. Mixing the compounds I or the compositions containing them in the use form as fungicides with other fungicides results in an enlargement of the fungicidal spectrum of action in many cases.
  • Sulfur, dithiocarbamates and their derivatives such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese zinc ethylenediamine bisdithiocarbamate, tetramethylthiaminodithidiumdithidiumdiamide, bis-dithiocarbamate, Ammonia complex of zinc (N, N 'propylene bis dithiocarbamate), zinc (N, N' propylene bis dithiocarbamate), N, N 'polypropylene bis (thiocarbamoyl) disulfide; Nitroderivate, such as dinitro- (1-methylheptyl) phenylcrotonate, 2-sec-butyl-4, 6-dinitrophenyl-3, 3-dimethylacrylate, 2-sec-butyl-4, 6-dinitrophenyl-isopropyl carbon
  • Heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, 0.0-diethyl-phthalimidophosphonothioate, 5-amino-l- [ bis- (dimethylamino) -phosphinyl] -3-phenyl-l, 2,4-triazole, 2,3-dicyano-1,4-di-thioanthraquinone, 2-thio-1,3-dithiolo [4,5 -b] Quinoxaline, 1- (butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester, 2-methoxycarbonylamino-benzimidazole, 2- (furyl- (2)) -benz - imidazole, 2- (thiazolyl- (4)) -benzimidazole, N. - (1, 1, 2, 2-t
  • Strobilurins such as methyl-E-methoxyimino- [ ⁇ - (o-tolyloxy) -o-tolyl] acetate, methyl-E-2- ⁇ 2- [6- (2-cyanophenoxy) pyrimidin-4-yl - oxy] -phenyl ⁇ -3-methoxyacrylate, methyl-E-methoxyimino- [ ⁇ - (2-phenoxyphenyl)] acetamide, methyl-E-methoxyimino- [ ⁇ - (2, 5-dimethylphenoxy) -o-tolyl ] acetamide,
  • Anilinopyrimidines such as N- (4, 6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- [4-Me- thyl-6-cyclopropyl-pyrimidin-2-yl] aniline,
  • Phenylpyrroles such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyrrole-3-carbonitrile,
  • Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acrylic morpholide, and various fungicides such as dodecylguanidine acetate,
  • the active ingredients were separated or together as a 10% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight .-% Wettol® EM (non-ionic emulsifier based on ethoxylated castor oil) prepared and diluted with water according to the desired concentration.
  • Nekanil® LN Litensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • .-% Wettol® EM non-ionic emulsifier based on ethoxylated castor oil
  • Example of use 1 Activity against wheat flour au
  • Leaves of potted vines of the "Müller-Thurgau" variety were sprayed to runoff point with aqueous preparation of active compound, which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier.
  • the plants were placed in the greenhouse for 7 days after the spray coating had dried on. Only then were the leaves inoculated with an aqueous suspension of zoospores from Plasmopara viticola.
  • the vines were then placed for 48 hours in a steam-saturated chamber at 24 ° C and then for 5 days in a greenhouse at temperatures between 20 and 30 ° C. After this time, the plants were again placed in a moist chamber for 16 hours in order to accelerate the sporangium carrier outbreak. The extent of the development of the infestation on the undersides of the leaves was then determined visually.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des dérivés d'acide 2-phénoxyphénylacétique de formule (I), dans laquelle les substituants et les indices ont la signification suivante: A représente (Ia) où R1 représente halogène, alkyle C¿1?-C4, alcoxy C1-C4, CF3, halogénure d'alcoxy C1-C4, formyle, C(=O)NR?aRb ou C(Ra)=NORb, Ra¿ représente hydrogène ou alkyle C¿1?-C4, R?b¿ représente alkyle C¿1?-C4, n vaut 1, 2, 3 ou 4, les groupes R?1¿ pouvant être différents lorsque n est différent de 1; R2 représente halogène, CH¿3? ou CF3; m vaut 0 ou 1 et X représente OCH3 ou NHCH3. L'invention concerne également un procédé et des produits intermédiaires pour la production des composés de formule (I) et l'utilisation de ces composés pour la lutte contre des champignons parasites.
EP99955883A 1998-11-04 1999-10-26 Derives d'acide 2-phenoxyphenylacetique, procede et produits intermediaires pour leur production, leur utilisation et agents les contenant pour la lutte contre des champignons parasites Withdrawn EP1127046A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19850729 1998-11-04
DE19850729 1998-11-04
PCT/EP1999/008083 WO2000026182A1 (fr) 1998-11-04 1999-10-26 Derives d'acide 2-phenoxyphenylacetique, procede et produits intermediaires pour leur production, leur utilisation et agents les contenant pour la lutte contre des champignons parasites

Publications (1)

Publication Number Publication Date
EP1127046A1 true EP1127046A1 (fr) 2001-08-29

Family

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EP99955883A Withdrawn EP1127046A1 (fr) 1998-11-04 1999-10-26 Derives d'acide 2-phenoxyphenylacetique, procede et produits intermediaires pour leur production, leur utilisation et agents les contenant pour la lutte contre des champignons parasites

Country Status (5)

Country Link
US (1) US6469195B1 (fr)
EP (1) EP1127046A1 (fr)
JP (1) JP2002528529A (fr)
AU (1) AU1266000A (fr)
WO (1) WO2000026182A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2009001876A (es) * 2006-08-21 2009-03-06 Array Biopharma Inc Derivados de acido fenoxifenilacetico 4-sustituidos.
US8435560B2 (en) * 2006-12-28 2013-05-07 Dow Corning Corporation Polynuclear microcapsules

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3623921A1 (de) 1986-07-16 1988-01-21 Basf Ag Oximether und diese enthaltende fungizide
GB8617648D0 (en) 1986-07-18 1986-08-28 Ici Plc Fungicides
ES2097583T3 (es) * 1989-05-17 1997-04-01 Shionogi & Co Procedimiento de preparacion de derivados de alcoxiiminoacetamida y un intermediario de este procedimiento.
DE4030038A1 (de) 1990-09-22 1992-03-26 Basf Ag Ortho-substituierte phenylessigsaeureamide
GB9023292D0 (en) * 1990-10-25 1990-12-05 Ici Plc Fungicides
DE4320499A1 (de) * 1993-05-14 1994-11-17 Bayer Ag Verfahren zur Herstellung von 2-Oximinoessigsäurederivaten

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0026182A1 *

Also Published As

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US6469195B1 (en) 2002-10-22
JP2002528529A (ja) 2002-09-03
WO2000026182A1 (fr) 2000-05-11
AU1266000A (en) 2000-05-22

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