WO2004077950A1 - Triazole-carboxamides substitues - Google Patents

Triazole-carboxamides substitues Download PDF

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Publication number
WO2004077950A1
WO2004077950A1 PCT/EP2004/001746 EP2004001746W WO2004077950A1 WO 2004077950 A1 WO2004077950 A1 WO 2004077950A1 EP 2004001746 W EP2004001746 W EP 2004001746W WO 2004077950 A1 WO2004077950 A1 WO 2004077950A1
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WIPO (PCT)
Prior art keywords
formula
propyl
ethyl
carbon atoms
methyl
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PCT/EP2004/001746
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English (en)
Inventor
Ernst Rudolf Gesing
Mark Wilhelm Drewes
Peter Dahmen
Dieter Feucht
Rolf Pontzen
Peter Lösel
Qinghong Tang
Jin Cao
Liang Chen
Xiuli Li
Yongbin Zhang
Xiaofei Li
Dinghui Zou
Honghuii Wu
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Bayer Cropscience Ag
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Publication of WO2004077950A1 publication Critical patent/WO2004077950A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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 invention relates to novel substituted triazolecarboxamides, to a process for their preparation and to their use as crop treatment agents, in particular as herbicides.
  • R 3 represents a halogenoalkyl of the formula
  • R 4 represents hydrogen, ethyl, n- or i-propyl or n-, s-, i- or t- butyl, and
  • R 5 represents halogenoalkyl having 1 to 6 carbon atoms and 1 to 3 halogen atoms.
  • Alkyl is in each case straight-chain or branched as far as this is possible.
  • Optionally substituted radicals can be mono- or polysubstituted, and in the case of poly- substitution, the substituents can be identical or different. Possible substituents are for instance alkoxy having 1 to 4 carbon atoms or halogen.
  • Halogen stands for fluorine, chlorine, bromine or iodine and preferably for fluorine, chlorine or bromine. Compounds wherein the halogen atom is chlorine are especially preferred.
  • the compounds of the formula (I) according to the invention may contain one or more asymmetrically substituted carbon atoms, in which cases they may be present in different enantiomeric (R- and S-conf ⁇ gured) forms or diastereomeric forms. In these cases, the invention relates both to the use of the different possible individual enantiomeric or stereoisomeric forms of the compounds of the formula (I) and of mixtures of these isomeric compounds.
  • R 1 preferably represents hydrogen, alkyl having 1 to 4 carbon atoms or dialkylamino having 1 to 4 carbon atoms in each alkyl group.
  • R 1 more preferably represents hydrogen, methyl, ethyl, n- or i- propyl, dimethylamino or diethylamino.
  • R 1 most preferably represents hydrogen or dimethylamino.
  • R 2 preferably represents hydrogen or alkyl having 1 to 4 carbon atoms.
  • R 2 more preferably represents hydrogen, methyl, ethyl, n- or i- propyl.
  • R 2 most preferably represents hydrogen or methyl.
  • R 4 preferably represents hydrogen, ethyl or i-propyl.
  • R 5 preferably represents halogen-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl having 1 to 3 halogen atoms.
  • R , 5 more preferably represents substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is mono-substituted by halogen.
  • R 5 is chlorine.
  • R 3 represents 2- chloro-1 -ethyl-ethyl, l-(chloromethyl)-propyl, l-(chloromethyl)-2-methyl-propyl, 2-chloro- propyl, 3-chloro-propyl, 2,3-dichloro-propyl, 2,2-dimethyl-3-chloro-propyl, 3-chloro-butyl, 2- chloro-butyl, 5-chloro-pentyl, 6-chlorohexyl, 2-fluoro-l -ethyl-ethyl, l-(fluoromethyl)-propyl, 1- (fluoromethyl)-2-methyl-propyl, 2-fluoro-propyl, 3-fluoro-propyl, 2,3-fluoro-propyl, 2,2- dimethyl-3-fluoro-propyl, 3-fluoro-
  • novel substituted triazolecarboxamides of the formula (I) have strong herbicidal activity.
  • R 1 and R 2 are defined as above, and
  • R 3' represents a hydroxy-substituted alkyl of the formula
  • R 4 represents hydrogen, ethyl, n- or i-propyl or n-, s-, i- or t- butyl, and
  • R 6 represents hydroxy-substituted alkyl having 1 to 6 carbon atoms and 1 to 3 hydroxy substituents are reacted with a halogenating agent.
  • R 6 preferably represents hydroxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl having 1 to 3 hydroxy substituents or more preferably represents substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is mono-substituted by hydroxy.
  • the starting materials of the formula (I)' also form part of the subject-matter of the present application.
  • R 1 and R 2 are defined as mentioned above
  • R 3 is defined as in formula (I)'
  • R 1 and R 2 are defined as mentioned above,
  • R 7 represents Alkyl and R 3 is defined as in formula (I)'
  • R 1 , R 2 and R 4 preferably, more preferably or most preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred or more preferred or most preferred for R 1 , R 2 and R 4 .
  • the formula (II) provides a general definition of the formamidines to be used as starting materials in the process (a) according to the invention for preparing compounds of the formula (I) ⁇
  • R 1 and R 2 preferably, more preferably or most preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred or more preferred or most preferred for R ] and R 2 .
  • the starting materials of the formula (II) are known organic chemicals for synthesis and/or can be prepared by processes known per se.
  • the formula (III) provides a general definition of the oxalic acid amide hydrazides further to be used as starting materials in the process (a) according to the invention for preparing compounds of the formula (I)'.
  • R 3 preferably, more preferably or most preferably has those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I)' according to the invention, as being preferred, more preferred or most preferred for R 3 .
  • the hydrazides of the formula (III) are known organic chemicals for synthesis and/or can be prepared by processes known in the art (cf. EP 0 412 358 Al, EP 0 126 326 A and example 2 below).
  • the formula (IN) provides a general definition of the aminoguanidines to be used as starting materials in the process (b) according to the invention for preparing compounds of the formula (I)'.
  • R 1 and R 2 preferably, more preferably or most preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I) according to the invention, as being preferred, more preferred or most preferred for R ⁇ nd R 2 .
  • aminoguanidines of the formula (IN) are known organic chemicals for synthesis and/or can be prepared by processes known in the art (cf. EP 0 332 991 Al).
  • the compounds of the formula (II) and (IN) can be used in form of acid adduct e.g. adducts with HC1 or acetic acid.
  • the formula (N) provides a general definition of the oxalic acid ester amides further to be used as starting materials in the process (b) according to the invention for preparing compounds of the formula (I)'.
  • R 3' preferably, more preferably or most preferably has those meanings which have already been mentioned above, in connection with the description of the compounds of the formula (I)' according to the invention, as being preferred, more preferred or most preferred for R 3 .
  • the starting materials of the formula (N) are known and/or can be prepared by processes known per se (cf. EP 0 332 991 Al).
  • Suitable halogenating agents are the customary chemicals suitable for converting akylhydroxy groups to the corresponding halogenoalkyl groups. Examples of suitable halogenating agents which may be mentioned are: SOCl 2 or POCl 3 .
  • DBU l,5-diazabicyclo[4.3.0]non-5-ene
  • DBU l,8-diazabicyclo[5.4.0]undec-7-ene
  • the process (a) according to the invention for preparing the compounds of the formula (I)' is preferably carried out using one or more diluents.
  • Suitable diluents for carrying out the process (a) according to the invention are preferably inert organic solvents.
  • reaction temperatures can be varied within a relatively wide range.
  • the processes are carried out at temperatures between +20°C and +150°C, preferably between 50°C and 100°C.
  • the processes according to the invention are generally carried out under atmospheric pressure.
  • the processes according to the invention under elevated or reduced pressure - in general between 0.1 bar and 10 bar.
  • the starting materials are generally employed in approximately equimolar amounts, except for the halogenating agent which is usually used in molar excess.
  • the reaction mixture is generally stirred at the required temperature for a number of hours.. Work-up is carried out by customary methods
  • the active compounds according to the invention can be used, for example, in connection with the following plants:
  • Daucus Glycine, Gossypium, Ipomoea, Lactuca, Linum, ycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
  • Monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.
  • the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
  • the active compounds according to the invention are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and rail tracks, and on paths and areas with and without tree plantings.
  • the active compounds according to the invention can be employed for controlling weeds in perennial crops, for example forests, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns, turf and pastureland, and for the selective control of weeds in annual crops.
  • the active compounds according to the invention can also be employed for controlling animal pests and fungal or bacterial plant diseases.
  • they can be used as insecticides and nematicides. If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.
  • Plants are to be understood as meaning in the present context all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional plant breeding and optimization methods or by biotechnological and recombinant methods or by combinations of these methods, including the transgenic plants and inclusive of the cultivars protectable or not protectable by plant breeders' rights.
  • Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes.
  • the plant parts also include harvested material, and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offsets and seeds.
  • Treatment according to the invention of the plants and plant parts with the active compounds is carried out directly or by allowing the compounds to act on their surroundings, environment or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
  • the active compounds can be converted into the customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, ⁇ soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric materials.
  • formulations are produced in a known manner, for example- by mixing the active compounds with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surfactants, that is, emulsifiers and/or dispersants, and or foam formers.
  • extenders that is, liquid solvents and/or solid carriers
  • surfactants that is, emulsifiers and/or dispersants, and or foam formers.
  • organic solvents as cosolvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chloro- benzenes, chloroethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, or else water.
  • Suitable solid carriers are: for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as highly-disperse silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or else protein
  • Tackii ⁇ ers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other possible additives are mineral and vegetable oils.
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic colorants such alizarin colorants, azo colorants and metal phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used as mixtures with known herbicides and/or substances which improve the compatibility with crop plants ("safeners"), finished formulations or tank mixes being possible. Also possible are mixtures with weed-killers comprising one or more known herbicides and a safener.
  • Possible components for the mixtures are known herbicides, for example
  • acetochlor acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazone, benzfendizone, benzobicyclon, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl), ch
  • safeners for example AD-67, BAS-145138, ben- oxacor, cloquintocet (-mexyl), cyometrinil, 2,4-D, DKA-24, dichlormid, dymron, fenclorim, fen- chlorazol (-ethyl), flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292, R-29148.
  • safeners for example AD-67, BAS-145138, ben- oxacor, cloquintocet (-mexyl), cyometrinil, 2,4-D, DKA-24, dichlormid, dymron, fenclorim, fen- chlorazol (-ethyl), flurazole, fluxofen
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in a customary manner, for example by watering, spraying, atomizing or broadcasting.
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.
  • the amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.
  • the treatment according to the invention may also result in superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used according to the invention also in combination with other agrochemically active compounds, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible which exceed the effects which were actually to be expected.
  • transgenic plants or cultivars which are preferably treated according to the invention include all plants which, in the genetic modification, received genetic material which imparted particularly advantageous useful properties ("traits") to these plants.
  • traits particularly advantageous useful properties
  • Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products.
  • transgenic plants which may. be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton and oilseed rape.
  • Traits that are emphasized are in particular increased defence of the plants against insects by toxins formed in the plants, in particular those formed in the plants by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A(a), CryIA(b), Cry ⁇ A(c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and also combinations thereof) (hereinbelow referred to as "Bt plants”).
  • Traits that are also particularly emphasized are the increased defence of the plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • Plant plants which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants examples include maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylurea, for example maize).
  • Herbicide-resistant plants plants bred in a conventional manner for herbicide tolerance
  • Clearfield® for example maize
  • the plants listed can be treated according to the invention in a particularly advantageous manner with the compounds of the formula (I) or the active compound mixtures according to the invention where in addition to the effective control of the weeds, the abovementioned synergistic effects with the transgenic plants or plant cultivators occur.
  • the preferred ranges stated above for the active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.
  • Example 2 To 20 ml SOC-2 there is added in small portions 2.74 g (16 mmol) 4H-l,2,4-triazol-3-yl- carboxylic acid-N-(2-hydroxy-propyl) amide under stirring. Then the reaction mixture is heated under reflux for two hours before the excess SOCl 2 is removed under vacuum and the residue is crystalized from ether, filtered and air dried.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants of a height of 5 - 15 cm are sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area.
  • the concentration of the spray liquor is chosen such that the particular amounts of active compound desired are applied in 1000 1 of water/ha.
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the preparation of active compounds such that the particular amount of active compound desired is applied per unit area.
  • the concentration of active compound in the spray liquor is chosen such that the particular amount of active compound desired is applied in 1000 litres of water per hectare.
  • Emulsifier part by weight of alkylaryl polyglycolether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) which are heavily infested by aphids (Myzus persicae) are treated by being dipped into the preparation of the active compound of the desired concentration.
  • mortality in % is determined. 100% means that all the beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.
  • Emulsifier 2 part by weight of alkylaryl polyglycolether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of the active compound of the desired concentration and are infested with larvae of the diamond- black moth (Plutella xylostella) as long as the leaves are still moist.
  • Emulsifier 2 part by weight of alkylaryl poly glycolether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Bean plants Phaseolus vulgaris which are heavily infested with all stages of the two- spotted spider mite (Tetranychus urticae) are treated by being dipped into the preparation of the active compound of the desired concentration.
  • Emulsifier 2 part by weight of alkylaryl polyglycolether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.

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  • 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)
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Abstract

L'invention concerne des triazole-carboxamides substitués de formule (I) dans laquelle R1, R2 et R3 sont tels que définis dans la description. Cette invention se rapporte en outre à l'utilisation de ces composés en tant qu'agents de traitement de récoltes, en particulier dans des herbicides, ainsi qu'à des procédés et des produits intermédiaires permettant de les préparer.
PCT/EP2004/001746 2003-03-06 2004-02-23 Triazole-carboxamides substitues WO2004077950A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN03119928.3 2003-03-06
CNA031199283A CN1526704A (zh) 2003-03-06 2003-03-06 取代的三唑甲酰胺化合物

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WO2004077950A1 true WO2004077950A1 (fr) 2004-09-16

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AR (1) AR043445A1 (fr)
WO (1) WO2004077950A1 (fr)

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