EP0906290A1 - Phenyluraciles substitues et leur utilisation comme herbicides - Google Patents

Phenyluraciles substitues et leur utilisation comme herbicides

Info

Publication number
EP0906290A1
EP0906290A1 EP97921676A EP97921676A EP0906290A1 EP 0906290 A1 EP0906290 A1 EP 0906290A1 EP 97921676 A EP97921676 A EP 97921676A EP 97921676 A EP97921676 A EP 97921676A EP 0906290 A1 EP0906290 A1 EP 0906290A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
substituted
optionally substituted
halogen
optionally
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Withdrawn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
EP97921676A
Other languages
German (de)
English (en)
Inventor
Roland Andree
Mark Wilhelm Drewes
Markus Dollinger
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.)
Bayer CropScience AG
Original Assignee
Bayer AG
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 AG filed Critical Bayer AG
Publication of EP0906290A1 publication Critical patent/EP0906290A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/557—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the invention relates to new substituted phenyluracils, a process for their preparation and their use as herbicides
  • the object of the present invention was to provide new phenyluracils with optimized herbicidal activity and, at the same time, compatibility with crop plants.
  • the object was achieved in that new substituted phenyluracils of the general formula (I) were found,
  • R 1 represents hydrogen, formyl or optionally substituted alkyl
  • R 2 represents optionally substituted alkyl
  • R 3 represents hydrogen, halogen or optionally substituted alkyl
  • R 4 represents hydrogen, cyano, nitro, halogen or alkoxy.
  • R 3 represents hydrogen, hydroxy, amino or for optionally substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonylamino, alkoxycarbonyl, alkylsulfonyl, alkylsulfonylamino Alkenyl, alkenyloxy, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylamino, arylcarbonylamino, arylsulfonylamino, arylalkyl, heterocyclyl or heterocyclylalkyl, and
  • R 6 stands for hydrogen or for optionally substituted alkyl, alkenyl or alkynyl, or together with R s stands for an alkanediyl group which optionally contains an oxygen atom at the beginning or end or within the hydrocarbon chain
  • R, R ⁇ , R and R have the meanings given above,
  • the new substituted phenyluracils of the general formula (I) are notable for their strong herbicidal activity. Surprisingly, the new ones show Compounds of formula (I) have a significantly better tolerance to crop plants, such as wheat or barley, and a considerably stronger action against weeds
  • the invention preferably relates to compounds of the formula (I) in which
  • R 1 represents hydrogen, formyl or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy,
  • R 2 represents alkyl with 1 to 6 carbon atoms optionally substituted by halogen
  • R ' represents hydrogen, halogen or optionally substituted by halogen
  • R 4 represents hydrogen, cyano, nitro, halogen or alkoxy with I to 4 carbon atoms
  • R 5 represents hydrogen, hydroxyl, amino or alkyl, alkoxy, alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonylamino, alkoxycarbonyl, alkylsulfonyl or alkyisulfonylamino, each with up to 6 carbon in each case optionally substituted by cyano, halogen or C, -C 4 -alkoxy ⁇ atoms, for each optionally substituted by halogen alkenyl, alkenyloxy or alkynyl each having up to 6 carbon atoms, for each optionally substituted by cyano, halogen or C 4 -C 4 alkyl cycloalkyl or cycloalkyl alkyl having 3 to 6 carbon atoms in the Cycloalkyl group and optionally up to 4 carbon atoms in the alkyl part, for each optionally by cyano, halogen, C r C 4 alkyl, C, -C 4 halo
  • R .6 stands for hydrogen or for alkyl, alkenyl or alkynyl, each optionally substituted by halogen, each with up to 6 carbon atoms, or together with R 5 stands for an alkanediyl grouping with up to 6 carbon atoms, which may be at the beginning or
  • saturated or unsaturated hydrocarbon chains such as alkyl, alkenyl or alkynyl, are each straight-chain or branched
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably
  • the invention relates in particular to compounds of the formula (I) in which
  • R 1 represents hydrogen or methyl, ethyl, n- or i-propyl, n-, I-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
  • R 2 represents methyl or ethyl optionally substituted by fluorine and / or chlorine
  • R 3 represents hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine,
  • R 4 represents hydrogen, cyano, nitro, fluorine, chlorine or methoxy
  • R 5 represents hydrogen, hydroxyl, amino or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, which are each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy , n- or i-propoxy, n-, 1-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, acetyl, propionyl, n- or i-butyroyl, Acetylamino, propionylamino, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl, ethylsulfonyl, n- or i-propyl sulf
  • R 6 represents hydrogen or methyl, ethyl, n- or i-propyl, propenyl, butenyl, propynyl or, in each case optionally substituted by fluorine or chlorine
  • Butinyl is, or together with R 5, ethane-1,2-diyl (dimethylene), propane-1,3-diyl (trimethylene), 2-oxa-propane-l, 3-diyl, butane-1,4-diyl (Tetra methylene), pentane-l, 4-diyl or 3-oxapentene-l, 5-diyl
  • the grouping NR R 6 has, for example, the meanings given in the following list: amino, hydroxyamino, hydrazino, methylamino, ethylamino, n-propylamino, i-
  • the grouping NR S R 6 has, for example, the meanings given above in Group 1
  • the grouping NR 5 R 6 has, for example, the meanings given above in Group 1
  • the grouping NR 5 R 6 has, for example, the meanings given above in Group 1.
  • the grouping NR 5r R 6 has here, for example, the meanings given above in Group 1.
  • the grouping NR ⁇ R 6 has, for example, the meanings given above in Group 1
  • the grouping NR R 6 has, for example, the meanings given above in Group 1 Group 8
  • the grouping NR 5 R 6 has, for example, the meanings given above in Group 1
  • Formula (I) chlorosulfonylphenyluracils to be used as starting materials are generally defined by the formula (II)
  • R ', R 2 , R 3 and R 4 preferably or in particular have those meanings which have already been mentioned above in connection with the description the compounds of formula (I) according to the invention preferably or as particularly preferred for R ! , R 2 , R 3 and R 4 were given
  • R 1 , R 2 , R 3 and R 4 have the meanings given above,
  • an alkali metal nitrite e.g. Sodium nitrite
  • hydrochloric acid e.g. hydrochloric acid
  • an organic diluent e.g. Acetic acid
  • a diluent such as Dichloromethane, 1,2-dichloroethane or acetic acid
  • a catalyst e.g. Copper (I) chloride and / or copper (II) chloride
  • aminophenyluracils of the general formula (IV) required as precursors are known and / or can be prepared by known processes (cf. EP 648749, preparation examples)
  • Formula (III) provides a general definition of the amino compounds to be used further as starting materials in the process according to the invention.
  • Formula (III) has R 3 and R 6 preferably or in particular those meanings which have already been described above in connection with the description of the compounds of the formula (I) according to the invention, preferably or as being particularly preferred for R 5 and R 6 were specified
  • the starting materials of the formula (III) are known synthetic chemicals
  • Suitable reaction auxiliaries for the process according to the invention for the preparation of the compounds of the formula (I) are generally the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates and hydrogen carbonates.
  • hydrides, hydroxides or alkanolates such as, for example Sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium - or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium - methanolate, ethanolate, -n- or -l-propanolate, -n-, -i-, -s- or -t-butanolate, furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamm, ethyl-dnsopropylamine, N, N-dimethyl-cyciohexylamine, dicyclohexylamine, ethyl-dicyclohexylamm, N, N-dimethylamline, N, N-dimethylbenzylamine, pyridine, 2-
  • Inert organic solvents are particularly suitable as diluents for carrying out the process according to the invention.
  • diluents include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene,
  • Chlorobenzene Chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane,
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C. and 150 ° C., preferably between 10 ° C. and 120 ° C.
  • the method according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the method according to the invention under high or reduced pressure - generally between 0.1 bar and 10 bar
  • the starting materials are used in approximately aquimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is stirred for several hours required temperature stirred
  • the working up is carried out according to customary methods (see the preparation examples)
  • the active compounds according to the invention can be used as defohants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants which grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends depends essentially on the amount applied
  • the active compounds according to the invention can be used, for example, in the following plants
  • Alopecurus apera Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.
  • the compounds of the formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon crops, such as, for example, maize, wheat and barley, both in the pre-emergence and in the post-emergence process
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in poly ⁇ other fabrics.
  • formulations are prepared in a known manner, e.g. B by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents
  • organic solvents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, Chlorethylene or methylene chloride, aliphatic carbon Hydrogens such as cyclohexane or paraffins, e.g.
  • Solid carrier materials that come into question are, for example, ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmonellonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, and solid carrier materials for granules Question e.g. broken and fractionated natural rocks like
  • emulsifiers and / or foam-generating agents are nonionic and anionic emulsifiers , such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates, as dispersants are, for example, 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 natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizann, 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 in general contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used as a weed control mixture with known herbicides, finished formulations being used or tank mixes are possible
  • known herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil, arylcarboxylic acids, such as, for example, dichloropicolinic acid, dicamba and picloram, aryloxyalkanoic acids, such as, for example, 2.4 D, 2.4 DB, 2.4 DP , Fluroxypyr, MCPA, MCPP and triclopyr, aryloxy-phenoxy-alkanoic acid esters, such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl,
  • chlorpropham, desmedipham, phenmedipham and propham chloroacetanihde, such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor, dinitroanilines, such as, for example, oryzalin, pendimethalin and trifluralin, biphenyl ether, such as zhenoxifluoride, biphenyl ether, such as z , Fluoroglycofen,
  • T ⁇ azines such as, for example, atrazine, cyanazine, simazin, Simetryne, terbutryne and terbutylazine
  • T ⁇ azinones such as, for example, hexazinone, metamitron and met ⁇ buzin, others, such as, for example, aminot ⁇ azole, benfuresate, bentazone, cinmethylin, clomazone, clopyralide, difithioquat , Ethofumesate, Fluorochlo ⁇ done, Glufosinate, Glyphosate, Isoxaben, Py ⁇ date, Quinchlorac, Quinmerac, Sulphosate and
  • 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.
  • the use is carried out in a customary manner, for example by pouring, spraying, spraying, Scatter
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • a solution of 0.42 g of sodium nitrite in 1.2 ml of water is stirred with stirring to a mixture of 2.0 g (6.1 mmol) of 1- (5-amino-4-cyano) cooled to 0 ° C. to 5 ° C. -5-fluorophenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-l (2H) -pyrimidine, 3.5 ml conc. Hydrochloric acid and 2 ml of acetic acid added dropwise. The mixture is stirred for about 30 minutes at 0 ° C. to 5 ° C.
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is watered with the preparation of the active ingredient
  • the amount of water per unit area expediently constant.
  • concentration of active substance in the preparation is irrelevant; the decisive factor is only the amount of active substance applied per unit area
  • Cultivated plants such as maize (0%), wheat (0%) and barley (0%), have a considerably stronger action than the known compound (A) against weeds such as Datura (100%), Ipomoea (100%), Polygonum ( 100%), echinochlea (70%), sorghum (100%) and xanthium (95%)
  • Datura 100%
  • Ipomoea 100%
  • Polygonum 100%
  • echinochlea 70%
  • sorghum 100%
  • xanthium xanthium
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants which have a height of 5-15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area.
  • the concentration of the spray mixture is chosen so that the respectively desired amounts of active compound are applied in 1000 l of water / ha

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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne de nouveaux phényluraciles substitués de formule générale (I), dans laquelle R?1, R2, R3, R4, R5 et R6¿ ont les significations données dans la description, un procédé de production de ces nouveaux composés, ainsi que leur utilisation comme herbicides. L'invention concerne en outre de nouveaux chlorophényluraciles substitués de formule (II), dans laquelle R?1, R2, R3 et R4¿ ont les significations données dans la description, ainsi qu'un procédé pour la production de ces composés.
EP97921676A 1996-05-02 1997-04-21 Phenyluraciles substitues et leur utilisation comme herbicides Withdrawn EP0906290A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19617532 1996-05-02
DE19617532A DE19617532A1 (de) 1996-05-02 1996-05-02 Substituierte Phenyluracile
PCT/EP1997/001998 WO1997042176A1 (fr) 1996-05-02 1997-04-21 Phenyluraciles substitues et leur utilisation comme herbicides

Publications (1)

Publication Number Publication Date
EP0906290A1 true EP0906290A1 (fr) 1999-04-07

Family

ID=7793060

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97921676A Withdrawn EP0906290A1 (fr) 1996-05-02 1997-04-21 Phenyluraciles substitues et leur utilisation comme herbicides

Country Status (10)

Country Link
US (1) US6107252A (fr)
EP (1) EP0906290A1 (fr)
JP (1) JP2000509401A (fr)
CN (1) CN1216983A (fr)
AU (1) AU718404B2 (fr)
BR (1) BR9708893A (fr)
CA (1) CA2253383A1 (fr)
DE (1) DE19617532A1 (fr)
IL (1) IL126827A0 (fr)
WO (1) WO1997042176A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001172108A (ja) * 1999-12-16 2001-06-26 Sumitomo Chem Co Ltd 除草方法
MEP7108A (en) * 2001-09-14 2010-06-10 Basf Se Herbicidal mixtures based on 3-phenyluracils
CN100405908C (zh) * 2003-03-13 2008-07-30 巴斯福股份公司 基于3-苯基尿嘧啶的除草混合物
RU2362772C2 (ru) * 2003-04-08 2009-07-27 Басф Акциенгезельшафт Производные бензолсульфонамида
WO2005007628A1 (fr) * 2003-07-11 2005-01-27 Bristol-Myers Squibb Company Derives de tetrahydroquinoleine constituant des modulateurs des recepteurs des cannabinoides

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5169430A (en) * 1991-08-09 1992-12-08 Uniroyal Chemical Company, Inc. Benzenesulfonamide derivatives and methods for their production
DE4140661A1 (de) * 1991-12-10 1993-06-17 Basf Ag Verwendung von 3-phenylurazil-derivaten zur desikkation und abzission von pflanzenteilen
ES2110667T3 (es) * 1993-08-18 1998-02-16 Bayer Ag N-cianoaril-heterociclos nitrogenados.
US5681794A (en) * 1993-08-18 1997-10-28 Bayer Aktiengesellschaft N-cyanoaryl-nitrogen heterocycles
DE4329537A1 (de) * 1993-09-02 1995-03-09 Basf Ag Substituierte 1-Amino-3-phenyluracile
US5486661A (en) * 1994-07-12 1996-01-23 Eaton Corporation Limit switch lever
JPH08157312A (ja) * 1994-12-02 1996-06-18 Nippon Bayeragrochem Kk 水稲用除草剤
DE19528305A1 (de) * 1995-08-02 1997-02-06 Bayer Ag Substituierte Phenyluracile

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9742176A1 *

Also Published As

Publication number Publication date
AU2766197A (en) 1997-11-26
US6107252A (en) 2000-08-22
BR9708893A (pt) 1999-08-03
CN1216983A (zh) 1999-05-19
IL126827A0 (en) 1999-08-17
WO1997042176A1 (fr) 1997-11-13
CA2253383A1 (fr) 1997-11-13
JP2000509401A (ja) 2000-07-25
DE19617532A1 (de) 1997-11-06
AU718404B2 (en) 2000-04-13

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