EP1017671A1 - Nouveaux derives de benzamidoxime, produits intermediaires et procedes pour les preparer et leur utilisation comme fongicides - Google Patents

Nouveaux derives de benzamidoxime, produits intermediaires et procedes pour les preparer et leur utilisation comme fongicides

Info

Publication number
EP1017671A1
EP1017671A1 EP98947519A EP98947519A EP1017671A1 EP 1017671 A1 EP1017671 A1 EP 1017671A1 EP 98947519 A EP98947519 A EP 98947519A EP 98947519 A EP98947519 A EP 98947519A EP 1017671 A1 EP1017671 A1 EP 1017671A1
Authority
EP
European Patent Office
Prior art keywords
formula
alkyl
alkoxy
derivatives
benzamide
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Withdrawn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
EP98947519A
Other languages
German (de)
English (en)
Inventor
Karl Eicken
Joachim Rheinheimer
Frank Wetterich
Eberhard Ammermann
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 EP1017671A1 publication Critical patent/EP1017671A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • the present invention relates to new benzamidoxime derivatives, processes and intermediates for their preparation and their use as fungicides.
  • JP-A 02/006453 describes benzamide oxime derivatives with fungicidal activity, which, however, cannot be completely satisfactory, especially when the application rates are low.
  • R 1 is hydrogen or fluorine
  • R 2 is phenyl-Ci-C ß -alkyl, which may carry one or more substituents selected from the group consisting of halo, C ⁇ -C4-alkyl, C ⁇ -C4-haloalkyl, C ⁇ -C 4 alkoxy or C ⁇ -C 4 ⁇ Can carry haloalkoxy, or
  • Thienyl-C . -C 4 alkyl which optionally one or more substituents selected from the group consisting of halogen, C ⁇ -C 4 -alkyl, C 4 haloalkyl, C ⁇ -C can carry 4 -haloalkoxy 4 alkoxy or C ⁇ -C , or
  • Pyrazole -CC 4 alkyl which optionally one or more substituents selected from the group consisting of halogen, -C 4 alkyl, Cj . -C 4 -Halogenalkyl, C ⁇ -C 4 alkoxy or -CC 4 ⁇ haloalkoxy can wear.
  • substituents R 1 and R the terms given stand as a term for a group of compounds.
  • Halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
  • - C 1 -C 4 alkyl for: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl, in particular for methyl or ethyl;
  • C ⁇ -C 4 haloalkyl for: a C ⁇ ⁇ C 4 alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, Chlorofluoromethyl, dichlorofluoromethyl, chlorine - difluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro 2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-
  • C 1 -C 4 -Alko y for: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy, in particular for methoxy or ethoxy;
  • - C ⁇ -C 4 haloalkoxy for: a C ⁇ -C 4 alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluorometh ⁇ oxy , Trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2, 2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2 -Chlor-2, 2-difluoroethoxy, 2,2-di-chloro-2-fluoroethoxy, 2, 2, 2-trichloroethoxy, pentafluoroethoxy, 2-fluor
  • Phenyl-Ci-Cg-alkyl for: e.g. Benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-1-yl, 1- (phenylmethyl) -eth-l-yl, 1- (Phenylmethyl) -1- (methyl) eth-l-yl or 1- (phenylmethyl) prop-1-yl, especially for benzyl or 2-phenylethyl;
  • Thienyl -CC 4 alkyl for: for example 2-thienylmethyl, 3-thienylmethyl, 2-thienylethyl, 2-thienylprop-l-yl or 3-thienylprop-1-yl;
  • Pyrazole-C 1 -C 4 -alkyl for: for example 1-pyrazolyl-methyl, 2-pyrazolyl methyl, 3-pyrazolylmethyl, 2-pyrazolylylethyl, 2-pyrazolyl-ylprop-1-yl or 3-pyrazolylprop-l-yl;
  • substituent R 2 is benzyl, which has one to three substituents selected from the above-mentioned group on the phenyl ring, in particular one to three substituents selected from fluorine, chlorine, methyl, methoxy or trifluoromethyl, have been found to be particularly special proven effective.
  • 4-fluorobenzyl, 4-chlorobenzyl, 4-methylbenzyl, 4-methoxybenzyl, 4-trifluoromethylbenzyl and 4-difluoromethoxybenzyl may be mentioned as particularly preferred substituents R 2 .
  • the benzamide oxime derivatives of the formula I according to the invention are obtained by the process according to the invention by reacting benzonitriles of the formula II with hydroxylamm or its salts in aqueous solution, preferably water or water / alkanol mixtures, if appropriate in the presence of a base, to give the benzamide oximes of the formula III, which are then reacted in a manner known per se in the presence of a base with cyclopropylmethyl halide to give the compounds of the formula IV.
  • the benzamide oximes IV can then be acylated in a manner known per se with the corresponding acid halides, preferably the corresponding acid chlorides, by heating inert solution (preferably to temperatures in the range from 20 to 100 ° C.).
  • Suitable inert solvents are in particular hydrocarbons or ethers, particularly preferably aromatic hydrocarbons such as toluene or xylene, to name just two examples.
  • the compounds I are distinguished by an excellent action against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. They are partly systemically effective and can therefore also be used as leaf and soil fungicides.
  • the plants are normally sprayed or dusted with the active compounds or the seeds of the plants are treated with the active compounds.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, in the case of water as
  • Diluents 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), wet nurses (e.g. ethanolamm, dimethylformamide) ) and water;
  • Carriers such as natural starch flours (e.g. kaolins, clays, talc, chalk) and synthetic starch flours (e.g.
  • Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignite sulfite liquors and methyl cellulose.
  • nonionic and anionic emulsifiers e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates
  • dispersants such as lignite sulfite liquors and methyl cellulose.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignm
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, Ammonium phosphate, ammonium nitrate, ureas and herbal products such as
  • Cereal flour tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • Castor oil A dispersion is obtained by finely distributing the solution in water.
  • V a mixture of 80 parts by weight, preferably a solid compound I according to the invention, 3 parts by weight of the sodium salt of di-iso-butylnaphthalm-2-sulfonic acid and 10 parts by weight of the sodium salt of a lignosulfonic acid, ground in a hammer mill from a sulfite waste liquor and 7 parts by weight of powdered silica gel; a spray broth is obtained by finely distributing the mixture of water;
  • a stable aqueous dispersion of 40 parts by weight of a compound I according to the invention, 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water can be further diluted;
  • Calcium salt of dodecylbenzenesulfonic acid 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 50 parts by weight of a paraffinic mineral oil.
  • the new compounds are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Deuteromycetes, Ascomycetes, Phycomycetes and Basidiomycetes. Some of them are systemically effective and can be used as foliar and soil fungicides.
  • the compounds are used by treating the fungi or the seeds, plants, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds.
  • the new compounds are particularly suitable for combating the following plant diseases:
  • Erysiphe graminis in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton and turf, Ustilago sugar species on cereals, Ustilago sugar on cereals, Ustilago varieties on cereals, Ustilago sugar varieties on cereals, Ustilago varieties on cereals, Ustilago varieties inaequalis (scab) on apples, Helminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinerea (gray mold) on strawberries, vines, ornamental plants and vegetables, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat, barley, Reisicularophyte oryzaza infestans on potatoes and tomatoes, Fu
  • the new connections can also be used in material protection (wood protection), e.g. against Paecilomyces variotii.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates are between 0.025 and 2, preferably 0.1 to 1 kg of active ingredient per ha.
  • active compound 0.001 to 50, preferably 0.01 to 10 g per kg of seed are generally required.
  • 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.
  • other active compounds for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
  • the fungicidal activity spectrum is enlarged in many cases.
  • Sulfur, dithiocarbamates and their derivatives such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese-zinc-ethylene-diamine-bis-dithiocarbamate, tetramethylthiuron-bis-dithiocarbamate, (bis) dithiocarbamate (bis) dithiocarbamate (bis) dithiocarbamate, bis-dithiocarbamate (bis) dithiocarbamate (bis) dithiocarbamate (bis) dithiocarbamate (bis) dithiocarbamate (bis) dithiocarbamate (dithiurocarbamate), , Ammonia complex of zinc (N, N '-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-
  • Nitroderivatives such as dinitro- (1-methylheptyl) phenylcrotonate, 2-sec. -Butyl-4, 6-dinitrophenyl-3, 3-dimethylacrylate, 2-sec. - Butyl-4, 6-dinitrophenyl-iso-propyl carbonate, 5-nitro-iso-phthalic acid di-iso-propyl ester;
  • heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, 0, O-diethyl-phthalimidophosphonothioate, 5-amino-l- [bis - (dimethylamino) -phosphinyl] - 3-phenyl-l, 2,4-triazole, 2,3-dicyano-l, 4-dithioanthraquinone,
  • fungicides such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N- (2,6-dimethylphenyl) -N-furoyl (2) -alaninate, DL-N- (2, 6-dimethyl-phenyl) -N- (2'-methoxyacetyl) -alanine-methyl ester, N- (2, 6-dimethylphenyl) -N -chloroacetyl-D, L-2-aminobutyrene - acton, DL-N- (2, 6-dimethylphenyl) -N- (phenylacetyl) -alanine methyl ester, 5-methyl-5-vinyl-3- (3, 5- dichlorophenyl) -2, 4-dioxo-l, 3-oxazolidine
  • Strobilurins such as methyl -E-methoximino- [ ⁇ - (o-tolyloxy) - o-tolyl] acetate, methyl -E-2 - ⁇ 2- [6- (2 -cyanophenoxy) pyridimin-4 -yl-oxy] phenyl ⁇ - 3-methoxyacrylate, methyl -E-methoximino- [ ⁇ - (2,5-dimethyloxy) -otolyl] acetamide.
  • Anilino-pyrimidines such as N- (4, 6-dimethylpyrimidin-2-yl) aniline, N- [4 -methyl -6 - (1-propynyl) pyrimidin-2-yl] aniline, N- (4-methyl-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.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des dérivés de benzamidoxime de la formule (I) dans laquelle les substituants ont la signification suivante: R<1> désigne hydrogène ou fluor, R<2> désigne phényle-alkyle C1-C6, qui peut porter sur le composé cyclique phényle un ou plusieurs substituants sélectionnés dans le groupe comprenant halogène, alkyle C1-C4, halogénure d'alkyle C1-C4, alcoxy C1-C4 ou halogénure d'alcoxy C1-C4, ou thiényle-alkyle C1-C4, qui peut éventuellement porter un ou plusieurs substituants sélectionnés dans le groupe comprenant halogène, alkyle C1-C4, halogénure d'alkyle C1-C4, alcoxy C1-C4 ou halogénure d'alcoxy C1-C4, ou pyrazol-alkyle C1-C4, qui peut éventuellement porter un ou plusieurs substituants sélectionnés dans le groupe comprenant halogène, alkyle C1-C4, halogénure d'alkyle C1-C4, alcoxy C1-C4 ou halogénure d'alcoxy C1-C4.
EP98947519A 1997-09-18 1998-09-05 Nouveaux derives de benzamidoxime, produits intermediaires et procedes pour les preparer et leur utilisation comme fongicides Withdrawn EP1017671A1 (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
DE19741098 1997-09-18
DE19741098 1997-09-18
DE19753520 1997-12-03
DE19753520 1997-12-03
DE19802460 1998-01-23
DE19802460 1998-01-23
PCT/EP1998/005618 WO1999014188A1 (fr) 1997-09-18 1998-09-05 Nouveaux derives de benzamidoxime, produits intermediaires et procedes pour les preparer et leur utilisation comme fongicides

Publications (1)

Publication Number Publication Date
EP1017671A1 true EP1017671A1 (fr) 2000-07-12

Family

ID=27217751

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98947519A Withdrawn EP1017671A1 (fr) 1997-09-18 1998-09-05 Nouveaux derives de benzamidoxime, produits intermediaires et procedes pour les preparer et leur utilisation comme fongicides

Country Status (6)

Country Link
US (2) US6417398B1 (fr)
EP (1) EP1017671A1 (fr)
AR (1) AR017121A1 (fr)
AU (1) AU9440198A (fr)
CA (1) CA2304052A1 (fr)
WO (1) WO1999014188A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2080433A2 (fr) 2002-03-21 2009-07-22 Basf Se Mélanges fongicides

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1125931A1 (fr) * 2000-02-17 2001-08-22 Hunan Research Institute of Chemical Industry (Hétéro)aryl-kétoxime-O-éthers alkyle substitués et méthode pour les fabriquer
DK1370633T3 (da) 2001-02-13 2005-11-21 Shell Int Research Smöremiddelsammensætning
EP2255627A3 (fr) 2004-04-30 2012-09-26 Basf Se Mélanges fongicides

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2696342B2 (ja) * 1988-06-27 1998-01-14 日本曹達株式会社 アミジン誘導体、その製造方法及び殺ダニ剤・農園芸用殺菌剤
CA2208585C (fr) 1994-12-19 2001-12-18 Nippon Soda Co., Ltd. Derive de benzamidoxime, procede de production, et bactericide agrohorticole
JPH1067730A (ja) * 1995-12-06 1998-03-10 Nippon Soda Co Ltd 新規なベンズアミドオキシム誘導体、その製法及び農園芸用殺菌剤

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9914188A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2080433A2 (fr) 2002-03-21 2009-07-22 Basf Se Mélanges fongicides

Also Published As

Publication number Publication date
WO1999014188A1 (fr) 1999-03-25
AR017121A1 (es) 2001-08-22
AU9440198A (en) 1999-04-05
US20030078437A1 (en) 2003-04-24
US6417398B1 (en) 2002-07-09
CA2304052A1 (fr) 1999-03-25

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