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
  • 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
  • A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
  • A01N37/50—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
• • 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
  • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
  • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
  • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/32—Oximes
  • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
  • C07C251/42—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a ring other than a six-membered aromatic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/32—Oximes
  • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
  • C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2601/00—Systems containing only non-condensed rings
  • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
  • C07C2601/14—The ring being saturated
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2601/00—Systems containing only non-condensed rings
  • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
  • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

• the present invention relates to organic compounds having herbicidal properties and plant growth regulating properties; to herbicidal compositions and processes utilising such compounds and to plant growth regulating compositions and processes utilising such compositions.
• cyclohexanone oxime ether compounds similar to those of Formula 1 below except that the substituent on the oxyamino group consists of an optionally substituted phenyl connected by a C 4 alkylene or alkenylene bridging chain to the ether oxygen, and that the cyclohexanone ring carries a single substituent in the 4-position. It is claimed that these compounds are herbicides with high selectivity for grasses. In a recently published European Patent Application EP 0 456 069 Al, (13 November 1991) BASF AG claim herbicides differing from those of US 5,022,914 in that the bridging chains are C 3 , C 5 and C 6 alkylene or alkenylene.
• the single substituent claimed on 4-position of the cyclohexanone ring is selected from C 1 -C 4 alkoxy- C 1 -C 4 alkyl, C 1 -C 4 alkythio-C 1 -C 6 -alkyl, optionally substituted C 3 -C 7 cycloalkyl, an optionally substituted five membered saturated heterocycle containing one or two heteroatoms selected from O or S, an optionally substituted saturated or unsaturated 6 to 7 membered heterocycle containing one or two heteroatoms selected from O or S, an optionally substituted five membered heteroaromatic containing one or two nitrogen atoms and one oxygen or sulphur atom, or phenyl or pyridyl which may be substituted with a substituent selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy,
• EP 0 456 069 specifically discloses as pendent substituents at the 4-position of the cyclohexanone ring only ethylthiopropyl, cyclohexyl, cyclohexenyl, or one of a series of heterocyclic rings, e.g. tetrahydrofuranyl, tetrahydrothiophenyl, dioxolanyl, dithiolanyl,
• US 5,022,914 and EP 0 456 069 in which the oxime capping group includes a phenyl or substituted' phenyl group other than those disclosed in US 4,440,566, US 5,022,914 or EP 0 456 069 are highly active pre-emergent and/or post-emergent herbicides or plant growth regulators and are particularly useful for controlling certain grass weeds in dryland and paddy rice.
• this invention provides novel compounds of Formula (1), agriculturally useful compositions of these compounds and methods of using these compounds as pre-emergent and/or post-emergent herbicides, and plant growth regulators: wherein
• A is selected from the group C 1 -C 3 alkylene and C 3 alkenylene each optionally substituted with 1-4 independently selected C 1 -C 3 alkyl substituents;
• X is selected from the group O, and a single bond
• R 1 is selected from the group H, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl,
• R 2 is selected from the group C 1 -C 6 alkyl, C 2 -C 8 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkylthio, C 3 -C 6 cycloalkyl, C 5 -C 6 cycloalkenyl, C 2 -C 8 alkoxyalkyl, C 2 -C 8 alkylthioalkyl, C 1 -C 4 alkyl substituted with a substituent selected from the group consisting of phenyl, phenoxy and thiophenoxy wherein the aromatic ring of said substituents is optionally substituted with 1- substituents selected from halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, nitro, cyano, amino, C 1 -C 4 haloalkyl and C 1 -C 4 haloalkoxy, and phen
• R 5 and R 6 are independently selected from the group H, C 1 -C 6 alkyl, C 2 -C 4
• R 5 and R 6 together with the ring carbon to which they are attached form a saturated or an unsaturated 3- to 7-membered carbocyclic ring, or a saturated or an unsaturated 5- to 7-membered heterocyclic ring containing 1-3 heteroatoms selected from the group consisting of 0-3 nitrogen, 0-2 oxygen and 0-2 sulphur atoms; the carbocyclic or heterocyclic ring being optionally substituted with 1-4 substituents independently selected from the group halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkoxycarbonyl, -COOH, C 2 -C 8 alkoxyalkyl, C 2 -C 8 alkylthioalkyl, and
• R 7 , R 8 and R 9 are independently selected from the group H; halogen; C 1 -C 4 alkyl;
• M is selected from the group Li + , Na + , K + , NH 4 + , and N(R 11 ) 4 + where R 11 is C 1 -C 4 alkyl;
• R 12 is selected from the group H, C 1 -C 4 alkyl ,benzyl, CO(C 1 -C 4 alkyl), and CO 2 (C 1 -C 4 alkyl);
• R 13 , R 15 , R 18 , R 22 and R 23 are independently selected from H and C 1 -C 3 alkyl;
• R 14 , R 16 , R 17 , R 19 and R 20 are independently selected from C 1 -C 3 alkyl;
• R 16 and R 17 can be taken together as -(CH 2 ) 2 - or -(CH 2 ) 3 -;
• R 19 and R 20 can be taken together as -(CH 2 ) 2 - or -(CH 2 ) 3 -; provided that:
• alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl”, denotes straight chain or branched alkyl, e.g. methyl, ethyl, n-propyl, isopropyl or the different butyl, pentyl or hexyl isomers.
• Alkoxy denotes straight chain or branched alkoxy, e.g. methoxy, ethoxy, n-propoxy, isopropyloxy, and the different butyloxy isomers.
• Alkenyl denotes groups formed from straight chain or branched alkenes, e.g. vinyl, 1-propenyl, 2-propenyl, 3-propenyl, etc.
• Alkynyl denotes groups formed from straight chain or branched alkynes, e.g., ethynyl, 1-propynyl, 2-propynyl, and the different butynyl isomers.
• Alkylsulphonyl denotes methylsulphonyl, ethylsulphonyl, propylsulphonyl, and the different butylsulphonyl isomers.
• Alkylthio alkylsulphinyl
• alkylamino alkylamino
• Cycloalkyl denotes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl.
• halogen either alone or in compound words such as “haloalkyl”, denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl” said alkyl may be partially halogenated or fully substituted with halogen atoms which may be the same or different. Examples of haloalkyl include CH 2 CH 2 F, CF 2 CF 3 and CH 2 CHFCl. "Alkylcarbonyl” denotes acetyl, propionyl, and the different butyryl isomers.
• Alkoxycarbonyl denotes methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, and the different butoxycarbonyl isomers.
• C i -C j prefix where i and j are numbers from 1 to 10.
• C 2 -C 3 alkylthioalkyl would designate -CH 2 SCH 3 , -CH 2 SC 2 -CH 2 CH 2 SCH 3 or -CH(CH 3 )SCH 3
• C 2 -C 5 alkoxyalkyl would represent -CH 2 OCH 3 through to -(CH 2 ) 4 OCH 3 or
• Groups of compounds of general formula (1) which are preferred for reasons including ease of synthesis and greater herbicidal efficacy include the following:
• R 1 is H, alkylsulphonyl, arylsulphonyl or M; and R 2 is C 1 -C 4 alkyl,
• C 1 -C 4 haloalkyl C 1 -C 4 alkenyl or C 2 -C 4 alkynyl .
• A is C 1 -C 2 alkylene or C3 -C 4 alkenylene optionally substituted with CH 3 or C 2 H 5 ;
• R 7 , R 8 and R 9 are independently H, Cl, Br, F, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, nitro, cyano or
• R 1 is H, Li+, Na +, or K+;
• R 2 is CH 3 , C 2 H 5 , n-C 3 H 7 or n-C 4 H 9 ;
• R 3 and R 4 are independently H, CH 3 or C 2 H 5 ;
• R 7 R 8 and R 9 are independently H, Cl, Br, F, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , SCH 3 , SC 2 H 5 , CF 3 , CHF 2 , CF 2 CF 3 , OCHF 2 , OCF 3 , OCH 2 CF 3 , NO 2 , CN CO 2 CH 3 Ph, SO 2 Ph, COPh, CH 2 Ph, OCH 2 Ph, OPh, SPh, NHPh or N(Me)Ph.
• R 5 and R 6 are independently C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkylthio or C 2 -C 6 alkylthioalkyl.
• R 1 is H, Li+, Na+ or K +;
• R 2 is CH 3 , C 2 H 5 , n-C 3 H 7 or n-C 4 H 9 ;
• R 3 and R 4 are independently H or CH 3 ;
• R 7 , R 8 and R 9 are independently H, Cl, Br, F, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , SCH 3 , SC 2 H 5 , CF 3 , CHF 2 CF 2 CF 3 , OCHF 2 , OCF 3 , OCH 2 CF 3 , NO 2 , CN, CO 2 CH 3 , Ph, SO 2 Ph, COPh, CH 2 Ph, OCH 2 Ph, OPh, SPh, NHPh or N(Me)Ph.
• R 5 and R 6 together with the carbon to which they are attached form a saturated or unsaturated 5-, 6- or 7-membered heterocyclic ring containing 1-2 heteroatoms selected from the group consisting of 0-2 nitrogen, 0-1 oxygen and 0-2 sulphur atoms; said ring is optionally substituted with 1-4 CH 3 groups.
• R 1 is H, Li +, Na+ or K+;
• R 2 is CH 3 C 2 H 5 , n-C 3 H 7 or n-C 4 H 9 ;
• R 3 and R 4 are independently H, CH 3 or C 2 H 5 ;
• R 7 , R 8 and R 9 are independently H, Cl, Br, F, CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , SCH 3 , SC 2 H 5 , CF 3 , CHF 2 , CF 2 CF 3 , OCHF 2 , OCF 3 , OCH 2 CF 3 , NO 2 , CN, CO 2 CH 3 , Ph, SO 2 Ph, COPh, CH 2 Ph, OCH 2 Ph, OPh, SPh, NHPh or N(Me)Ph. Examples of compounds within the scope of this invention are given in the Table 1 which follows.
• the compounds of the invention may be prepared by standard synthetic procedures including the process outlined in US 4,440,566.
• Appropriate cyclohexanediones may be acylated on oxygen and the enol esters isomerised (Fries rearrangement) to give th C-substituted products .
• the C-acylated derivatives may be reacted with O-substituted hydroxylamines which may in turn be generated in situ from appropriate precursors, to afford derivatives of the general Formula (1) wherein R 1 is hydrogen.
• R 1 is not hydrogen
• compounds of the inventio of Formula (1) wherein R 1 is an organic or inorganic cation may be prepared from compounds of the invention of Formula (1) wherein R 1 is hydrogen by reacting thes latter compounds with an appropriate inorganic or organic base.
• the compounds of the invention are highly active pre- emergent and/or post-emergent herbicides or plant growth regulants. These compounds are useful for controlling certain grass weeds in small grain cereals such as wheat (Triticum aestivum) and barley (Hordeum vulgare), examples of which include, but are not limited to, Centurk wheat, Era wheat, Igri barley and Klages barley.
• Many of the compounds of this invention are especially useful for the control of selected grass weeds, such as wild oats (Avena fatua), black grain (Alopecurus myosoides), crabgrass (Digitaria sanguinalis), foxtails (Setaria spp.) and Italian ryegrass (Lolium multiflonim). These compounds are also particularly useful for controlling certain grass weeds in dryland and paddy rice (Orysa sativa), examples of which include, but are not limited to, Indica and Japonica varieties of the crop. Many of the compounds of this invention are especially useful for the control of selected grass weeds, such as barnyardgrass (Echinochloa crusgalli), in paddy rice.
• selected grass weeds such as barnyardgrass (Echinochloa crusgalli), in paddy rice.
• these compounds also have utility for broad-spectrum pre- and/or post-emergence weed control in areas where control of all vegetation is required. Alternatively, these compounds are useful to regulate plant growth. Rates of application for compounds of this invention are determined by a number of factors. These factors include formulation selection, method of application, amount of vegetation present, growing conditions, etc. In general, the subject compounds should be applied at rates of 0.005 to 5 kg/ha with a preferred rate range of 0.01 to 1 kg/ha. One skilled in the art can easily determine application rates necessary for the desired level of weed control.
• the invention provides a herbicidal composition comprising a mixture of at least one herbicidal compound of formula (1) as hereinbefore defined with at least one other herbicide.
• the invention provides a method for regulating the growth of a plant comprising applying to the plant, to the seed of the plant, or to the growth medium of the plant an effective amount of a compound of Formula (1) as hereinbefore defined.
• Rates of application of these compounds can be influenced by many factors of the environment and should be determined under actual use conditions. Weed grasses in graminaceous crops can normally be killed when treated at a rate of from less than 0.1 to about 1 kg active ingredient/ha.
• the compounds of this invention can be mixed with fungicides, bactericides, acaricides, nematicides, insecticides, or other biologically active compounds in order to achieve desired results with a minimum expenditure of time, effort and material.
• Amounts of these biologically active materials added for each part by weight of the composition of this invention may vary from 0.05 to 25 parts by weight. Suitable agents of this type are well known to those skilled in the art.
• Useful formulations of the compounds within the scope of this invention can be prepared in conventional ways. They include dusts, granules, pellets, solutions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from one litre to several hundred litres per hectare. High strength compositions are primarily used as intermediates for further
• the formulations broadly, contain about 1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 5% to 99% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the approximate proportions given in the table below:
• compositions may be in the form of dusting powders or granules comprising the active ingredient and a solid diluent or carrier therefor, for example, kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth, gypsum, Hewill's earth, diatomaceous earth, and China clay.
• the compositions may also be in the form of dispersible powders or grains comprising a wetting agent to facilitate the dispersion in liquids of the powder or grains which may contain also solid diluents, fillers and suspending agents.
• Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J. The more absorptive diluents are preferred for the wettable powders and the denser ones for dusts. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.
• compositions for dressing seed may contain an agent (for example a mineral oil) for assisting the adhesion of the composition to the seed.
• agent for example a mineral oil
• the aqueous dispersions or emulsions may be prepared by dissolving the active ingredient(s) in an organic solvent optionally containing wetting, dispersing or emulsifying agent(s) and then adding the mixture to water which may also contain wetting, dispersing or emulsifying agent(s).
• Suitable solvents are acetone, ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, the xylenes and trichloroethylene amongst others.
• Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C.
• McCutcheon's Detergents and Emulsif ⁇ ers Annual MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses.
• compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, US Pat. No. 3.060,084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. The synthesis and biological activity of the compounds of formula 1 is illustrated by the following non-limiting examples.
• N,N-diisopropylethylamine (15.4g) in DMF (30 ml). After 48 hours at 20°C and 48 hours at 45°C the mixture was diluted with water (1000 ml) and filtered. The residue was washed thoroughly with water to give the product as a white solid (13.8g ), m.p.
• Tri-N-propylamine (31.5g) was added dropwise to a mixture of 5,5-dimethylcyclohexane-1,3-dione(14g), butyric anhydride(17.4g) and
• N,N-(4-dimethyIamino)pyridine (1g) and the mixture stirred at room temperature for 16 hours.
• the solution was cooled in ice, acidified to pH 3 with 2N hydrochloric acid and extracted with ether (x3).
• the combined ether extracts were washed with water, dried and the solvent removed under reduced pressure.
• the product was freed from residual butyric acid and butyric anhydride by heating at 50°C and 1mm pressure until no further material was removed and the residue was used in the next step without further purification.
• N-(4-phenylbenzyloxy)phthalimide (2.2g) in ethanol (24 ml). After a clear solution had formed the butyroyl compound (1.3g) was added and the solution was buffered t pH 4 by the addition of glacial acetic acid. After 16 hours at 20° the solvent was removed under reduced pressure, the residue was acidified to pH 2-3 with dilute hydrochloric acid and then extracted with ether (3x). The combined ether extracts were washed with water, the ether removed by evaporation and the residue was purified by chromatography over silica to give the product as a colourless solid (1.3g m.p.
• N,N-Diethylethylenediamine (0.5g) was added to a stirred suspension of N-(4-fluorophenyl)benzyloxyphthalimide (1g) in ethanol (12ml). After a clear solution had formed the crude triketone (1c, 0.6g) was added and the reaction mixture was buffered to pH4 by the addition of glacial acetic acid. After 24hrs volatile materials were removed under reduced pressure, the residue was stirred into water (50ml) and the mixture was extracted with ether. The ether extract was washed with brine, dried and the ether removed by evaporation.
• Example 6 To demonstrate the effectiveness of compounds of Formula (1) of the present invention as herbicidal agents, the compounds of Formula (1) listed in Table 2 were applied to bamyardgrass and rice postemergent at 0.1 and 0.4 kg/hectare. The herbicidal data are shown in Table 2 In the table 0 signifies no effect and 10 signifies plant dead. As can be seen the compounds of Formula (1) selectively control bamyardgrass in rice, although a few of the compounds, notably 1.48 and 1.118 are sufficiently active to kill rice at the test concentrations. In secondary screening tests at lower application rates (30 and 60 g/ha) these compounds show good selectivity.

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• Chemical & Material Sciences (AREA)
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• Engineering & Computer Science (AREA)
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• Wood Science & Technology (AREA)
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• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 1992
  • 1992-11-03 TW TW081108711A patent/TW221367B/zh active
  • 1992-11-13 PT PT101060A patent/PT101060A/pt not_active Application Discontinuation
  • 1992-11-13 JP JP5508826A patent/JPH07500841A/ja active Pending
  • 1992-11-13 WO PCT/AU1992/000612 patent/WO1993010081A1/en active Application Filing
  • 1992-11-14 CN CN92114386A patent/CN1073675A/zh active Pending

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