WO1995032621A2 - Herbicides pour cultures de specialites - Google Patents

Herbicides pour cultures de specialites Download PDF

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Publication number
WO1995032621A2
WO1995032621A2 PCT/US1995/003188 US9503188W WO9532621A2 WO 1995032621 A2 WO1995032621 A2 WO 1995032621A2 US 9503188 W US9503188 W US 9503188W WO 9532621 A2 WO9532621 A2 WO 9532621A2
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WO
WIPO (PCT)
Prior art keywords
sugarcane
methyl
citrus
grapes
compound
Prior art date
Application number
PCT/US1995/003188
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English (en)
Other versions
WO1995032621A3 (fr
Inventor
Kofi Sam Amuti
Original Assignee
E.I. Du Pont De Nemours And Company
Degussa Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by E.I. Du Pont De Nemours And Company, Degussa Aktiengesellschaft filed Critical E.I. Du Pont De Nemours And Company
Priority to AU19981/95A priority Critical patent/AU1998195A/en
Priority to BR9507902-5A priority patent/BR9507902A/pt
Priority to EP95913687A priority patent/EP0762833A2/fr
Publication of WO1995032621A2 publication Critical patent/WO1995032621A2/fr
Publication of WO1995032621A3 publication Critical patent/WO1995032621A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • TITLE HERBICIDES FOR SPECIALTY CROPS This invention comprises certain triazolinones and their agriculturally suitable salts for weed control in plantation crops. Some compounds employed in the instant invention are disclosed in
  • the yields of selected plantation crops such as citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, and fruit trees tend to be lessened by undesired plants such as crabgrass, guineagrass, itchgrass and the like.
  • the yields of these crops tend to be reduced by crop plants such as corn, cotton, wheat, rice, and the like. A need therefore exists for controlling undesired plants to improve the yields of plantation crops such as those mentioned above.
  • R 1 is F or Cl
  • R 2 is H, CH 3 , or CH 2 CH 3 ; and R 3 is C ⁇ -C 4 alkyl or C r C 4 haloalkyl; or the corresponding N-oxide or agriculturally suitable salt thereof.
  • Preferred 1 The method-of-use described above employing compounds of
  • Preferred 2 The method of Preferred 1 wherein the compound is l-(7-chloro-5- fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-4-difluoromethyl-4,5-dihydro- 3-methyl-l,2,4-triazol-5(lH)-one.
  • Formula I wherein the crop is selected from the group consisting of coffee, cocoa, oil palm, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, rubber, pineapple and loblolly pine.
  • Preferred 4 The method of Preferred 3 wherein the plantation crops are selected from the group consisting of sugarcane, citrus, grapes, and fruit trees.
  • Preferred 5 The method of Preferred 2 wherein the plantation crops are selected from the group consisting of coffee, cocoa, oil palm, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, rubber, pineapple and loblolly pine.
  • Preferred 6 The method of Preferred 5 wherein the plantation crops are selected from the group consisting of sugarcane, citrus, grapes, and fruit trees.
  • Preferred 7 The method of Preferred 4 wherein the crop is citrus.
  • Preferred 8 The method of Preferred 4 wherein the crop is sugarcane.
  • Preferred 9 The method of Preferred 4 wherein the crop is grapes.
  • Preferred 10 The method of Preferred 2 wherein the crop is fruit trees.
  • Compounds of Formula I can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers and geometric isomers.
  • One skilled in the art will appreciate that one stereoisomer may be more active than the others and how to separate said stereoisomers.
  • the present invention comprises mixtures, individual stereoisomers, and optically active mixtures of compounds of Formula I as well as agriculturally suitable salts thereof.
  • alkyl used either alone or in compound words such as “haloalkyl” includes straight or branched alkyl such as methyl, ethyl, n-propyl, isopropyl and the different butyl isomers.
  • halo in “haloalkyl”, denotes fluorine, chlorine, bromine or iodine.
  • said alkyl can be partially or fully substituted with independently selected halogen atoms. Examples pf haloalkyl include CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFC1.
  • C4 alkyl designates the various isomers of an alkyl group containing a total of 4 carbon atoms, examples including CH 2 CH 2 CH 2 CH 3 , CH 2 CH(CH 3 ) 2 , and C(CH 3 ) 3 .
  • R 1 through R 3 in the compounds of Formulae 1-8 below are as defined above in the Summary of the Invention.
  • the triazolinone can be functionalized with R 3 to form compounds of Formula I as described in GB 2,090,250 and illustrated in Scheme 2.
  • the triazolinone of Formula 4 is reacted with a base and a haloethylene or an electrophile of Formula R 3 Z wherein Z is a halide.
  • the reaction is generally performed at a temperature of about 0°-150°C.
  • An inert solvent is preferably used in the reaction.
  • benzene, toluene, chlorobenzene, xylene, diethyl ether, tetrahydrofuran, dioxane, methanol, ethanol, propanol, ethylene glycol, acetone, methyl ethyl ketone, cyclohexanone, ethyl acetate, dimethylformamide, dimethylacetamide, water, or dimethylsulfoxide can be used.
  • These solvents can be used alone or in combination with one another.
  • the bases which can be used for the above reaction include, for example, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydroxide, potassium carbonate, sodium methoxide, pyridine, trimethylamine, triethylamine, diethylaniline, or l,8-diazabicyclo[5.4.0]undec-7-ene.
  • Preferred bases ire sodium hydroxide, potassium hydroxide, and potassium carbonate.
  • a two-phase reaction can also be used to conduct the reaction, between an aqueous solution layer containing a base such as sodium hydroxide, and an organic solvent layer in the presence of a phase transfer catalyst such as triethylbenzylammonium chloride or tetrabutylammonium bromide.
  • a phase transfer catalyst such as triethylbenzylammonium chloride or tetrabutylammonium bromide.
  • the desired triazolinone can be obtained through extraction into a water-immiscible solvent and purification by chromatography or recrystallization.
  • the hydrazine of Formula 2 can be prepared from the corresponding aniline using well-known methods for preparing phenylhydrazines (e.g., see J. Timberlake; J. Stowell; The Chemistry of the Hydrazo, Azo, andAzoxy Groups (S. Patai, Ed.) John Wiley and Sons, Ltd., London (1975), p 69; and Demers, J. P.; Klaubert, D. J.; Tetrahedron Lett. (1987), 4933).
  • the aniline can be prepared by reduction of the corresponding nitro-substituted dihydrobenzofuran, for example by hydrogenation over palladium on carbon.
  • the nitro- substituted dihydrobenzofuran can be prepared by the methods disclosed in U.S. 4,881,967, U.S 4,213,773, and U.S. 4,315,767.
  • One method involves cyclization of a phenol as illustrated in Scheme 3.
  • the CH 2 R 4 group in Formula 6 corresponds to R 2 as methyl or ethyl.
  • the cyclization can be effected by heating, acid-catalysis, or free radical methods.
  • Preparation of the dihydrobenzofuran can also be accomplished by dehydration of a diol as illustrated in Scheme 4 and taught in U.S. 4,881,967.
  • dihydrobenzofuran ring can be prepared using the methods illustrated in Schemes 3 and 4 with the triazolinone ring in place of the nitro group.
  • Formulation/Utilitv Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent and/or a surfactant wherein the formulation is consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels.
  • Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible (“wettable”) or water-soluble.
  • Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredient.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses.
  • All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
  • Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,_V-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers.
  • Solid diluents include, for example, clays such as bentonite, montmorillinite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • clays such as bentonite, montmorillinite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4- methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
  • Solutions can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
  • Example B Wettable Powder l-(7-chloro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)- 4-difluoromethyl-4,5-dihydro-3-methyl- 1 ,2,4-triazol-5( lH)-one 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
  • Example C Granule l-(7-chloro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)- 4-difluoromethyl-4,5-dihydro-3-methyl- 1 ,2,4-triazol-5( lH)-one 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%.
  • Example D Extruded Pellet l-(7-chloro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)- 4-difluoromethyl-4,5-dihydro-3-methyl- 1 ,2,4-triazol-5( lH)-one 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
  • the compounds of Formula I are active herbicides for selective and/or general broadleaf and grass weed control in plantation crops including coffee, cocoa, oil palm, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, rubber, pineapple and loblolly pine. Preferred is the method of using compounds of Formula I in sugarcane, citrus, grapes, and fruit trees.
  • the compounds of Formula I can be applied as a preemergence or postemergence treatment using techniques such as banding, directed sprays, or broadcast applications.
  • the compounds of Formula I can be used in areas where control of vegetation is desired, such as around fuel storage tanks, industrial storage areas, oil well sites, drive-in theaters, around billboards, highway and railroad structures and in fence rows.
  • the compounds of Formula I can be used for selective weed control in plantation crops.
  • the compounds of this invention are used at 5 to 5000 g/ha with a preferred rate range of 10 to 2000 g/ha rate.
  • One skilled in the art can select the proper rates for a given situation.
  • Compositions comprising the active compounds of Formula I are generally used alone or in combination with other commercial herbicides, insecticides or fungicides.
  • the compounds of Formula I are particularly useful in combinations with other herbicides for total vegetation control in plantation crops.
  • Examples of other herbicides with which compounds of Formula I can be formulated are: acetochlor, acifluorfen, acrolein, azimsulfuron, 2-propenal, alachlor, ametryn, amidosulfuron, ammonium sulfamate, amitrole, anilofos, asulam, atrazine, barban, benazolin, benefin, benfuresate, bensulfuron methyl, bensulide, bentazon, benzofluor, benzoylprop, bifenox, bromacil, bromoxynil, bromoxynil heptanoate, bromoxynil octanoate, butachlor, buthidazole
  • Compound No. 1 Compound No.2 TEST A Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloa crus-galli), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), cheatgrass (Bromus secalinus), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail (Setariafaberi ⁇ ), lambsquarters (Chenopodium album), morningglory (Ipomoea hederace ⁇ ), rape (Brassica napus), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrast ⁇ ), wheat (Tritic
  • Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.
  • Rate 400 g/ha 1 2 Rate 400 g/ha 1 2
  • Morningglory 9 Morningglory 10
  • Rate 100 g/ha 1 2 Rate 100 g/ha 1 2
  • Morningglory 8 Morningglory 10 6
  • test compound was formulated in a non-phytotoxic solvent mixture which includes at least one surfactant and applied preemergence and/or postemergence to the plants. Preemergence applications were made within one day of planting the seeds or plant parts. Postemergence applications were applied when the plants were in the two to four leaf stage (three to twenty cm). Untreated control plants and treated plants were placed in the greenhouse and visually evaluated for injury at 14 to 28 days after herbicide application. Plant response ratings, summarized in Table B, are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash (-) response indicates no test result.
  • Rate 500 g/ha 1 Rate 500 g/ha 1
  • Peanuts 30 Peanuts 0
  • Rate 250 g/ha 1 2 Rate 250 g/ha 1 2
  • Dallisgrass 17 a 0 Dallisgrass 100 a 100
  • Guineagrass 5 a 0 Guineagrass 100 a 70
  • Peanuts 5 a 10 Peanuts 29 a 20
  • Rate 125 g/ha 1 Rate 125 g/ha 1
  • Guineagrass 0 Guineagrass 100
  • Morningglory 65 Morningglory 60
  • Morningglory 20 Morningglory 15
  • the pots were sprayed preemergence with the compound formulated in a non-phytotoxic solvent mixture which includes a surfactant.
  • the treatments were visually rated 23 and 51 days-after-treatment (DAT) and compared with appropriate controls.
  • the plant response ratings scale used in Test B were also used here. The results are shown in Table D. A dash indicates the test was not run.
  • Guineagrass 100 100 80 30 51 DAT
  • Itchgrass 100 100 0 0
  • Guineagrass 100 100 80 20
  • Guineagrass 0 0 0 0 0 0 0 0 0 0 0
  • Rooted cuttings of citrus were planted in plastic pots.
  • the pots were also seeded with guineagrass, sandbur, goosegrass and green pigweed (Amaranthus viridis), another pot was planted with sugarcane stem pieces and purple nutsedge tubers.
  • the citrus was sprayed to simulate field type post-directed herbicide application, the sugarcane and purple nutsedge were treated postemergence and the weeds were treated preemergence with the compound in a non-phytotoxic solvent mixture which includes a surfactant. Treated plants were visually rated and compared with appropriate controls. The plant response ratings used in Test B were also used here. The results are shown in Table F.

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

Abstract

Cette invention se rapporte à l'utilisation d'herbicides représentés par la formule (I), où R1 représente F ou Cl; R2 représente H, CH¿3? ou CH2CH3; et R?3¿ représente alkyle C¿1?-C4 ou haloalkyle C1-C4; ou à l'utilisation du N-oxyde correspondant ou de leurs sels appropriés à un usage agricole. Les herbicides qui contiennent des composés de la formule (I) possèdent un pouvoir désherbant à large spectre dans les cultures de plantations, telles que le citrus, la canne à sucre, le café, la banane, le palmier à huile, le pin à encens, le caoutchouc, le cacao, le raisin, le plantin, l'ananas, les arbres fruitiers, ainsi que les noyers, noisetiers, amandiers, arachides, et similaires.
PCT/US1995/003188 1994-05-27 1995-03-20 Herbicides pour cultures de specialites WO1995032621A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU19981/95A AU1998195A (en) 1994-05-27 1995-03-20 Herbicides for specialty crops
BR9507902-5A BR9507902A (pt) 1994-05-27 1995-03-20 Método para controle de ervas daninhas em culturas de plantação
EP95913687A EP0762833A2 (fr) 1994-05-27 1995-03-20 Herbicides pour cultures de specialites

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US25040094A 1994-05-27 1994-05-27
US08/250,400 1994-05-27

Publications (2)

Publication Number Publication Date
WO1995032621A2 true WO1995032621A2 (fr) 1995-12-07
WO1995032621A3 WO1995032621A3 (fr) 1996-02-22

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EP (1) EP0762833A2 (fr)
AU (1) AU1998195A (fr)
BR (1) BR9507902A (fr)
WO (1) WO1995032621A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1053679A1 (fr) * 1999-05-05 2000-11-22 Aventis Cropscience S.A. Compositions herbicides
JP2002521001A (ja) * 1997-02-26 2002-07-09 エフ エム シー コーポレーション シクロイミド置換ベンゾ縮合ヘテロ環状除草剤

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0271170A2 (fr) * 1986-12-10 1988-06-15 Shell Internationale Researchmaatschappij B.V. Benzofurannes et benzopyrannes substitués herbicides
WO1992004827A1 (fr) * 1990-09-13 1992-04-02 E.I. Du Pont De Nemours And Company Triazoles herbicides bicycliques substitues
WO1992013453A1 (fr) * 1991-02-01 1992-08-20 E.I. Du Pont De Nemours And Company Herbicides utilises dans la culture d'agrumes, de cannes a sucre , de palmiers a huile et analogues
EP0578089A1 (fr) * 1992-07-10 1994-01-12 Bayer Ag Triazolinones substitués par des hétérocycles, procédé pour leur préparation et leur utilisation comme herbicides
EP0597360A1 (fr) * 1992-11-12 1994-05-18 Bayer Ag N-phényle-triazolin (thi)ones substitués, procédés et produits intermédiaires pour leur préparation et leur utilisation comme herbicides, insecticides et acaricides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0271170A2 (fr) * 1986-12-10 1988-06-15 Shell Internationale Researchmaatschappij B.V. Benzofurannes et benzopyrannes substitués herbicides
WO1992004827A1 (fr) * 1990-09-13 1992-04-02 E.I. Du Pont De Nemours And Company Triazoles herbicides bicycliques substitues
WO1992013453A1 (fr) * 1991-02-01 1992-08-20 E.I. Du Pont De Nemours And Company Herbicides utilises dans la culture d'agrumes, de cannes a sucre , de palmiers a huile et analogues
EP0578089A1 (fr) * 1992-07-10 1994-01-12 Bayer Ag Triazolinones substitués par des hétérocycles, procédé pour leur préparation et leur utilisation comme herbicides
EP0597360A1 (fr) * 1992-11-12 1994-05-18 Bayer Ag N-phényle-triazolin (thi)ones substitués, procédés et produits intermédiaires pour leur préparation et leur utilisation comme herbicides, insecticides et acaricides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002521001A (ja) * 1997-02-26 2002-07-09 エフ エム シー コーポレーション シクロイミド置換ベンゾ縮合ヘテロ環状除草剤
EP1053679A1 (fr) * 1999-05-05 2000-11-22 Aventis Cropscience S.A. Compositions herbicides

Also Published As

Publication number Publication date
WO1995032621A3 (fr) 1996-02-22
BR9507902A (pt) 2004-10-19
AU1998195A (en) 1995-12-21
EP0762833A2 (fr) 1997-03-19

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