WO1996029314A1 - Thiocarbamoylverbindungen - Google Patents
Thiocarbamoylverbindungen Download PDFInfo
- Publication number
- WO1996029314A1 WO1996029314A1 PCT/EP1996/000971 EP9600971W WO9629314A1 WO 1996029314 A1 WO1996029314 A1 WO 1996029314A1 EP 9600971 W EP9600971 W EP 9600971W WO 9629314 A1 WO9629314 A1 WO 9629314A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- methyl
- compounds
- phenyl
- acid
- Prior art date
Links
- JIRRQZVKOJEHDK-UHFFFAOYSA-N NC([n]1ncc(CC2CCCC2)c1O)=S Chemical compound NC([n]1ncc(CC2CCCC2)c1O)=S JIRRQZVKOJEHDK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Definitions
- the application relates to the use of partially known thiocarbamoyl compounds, their preparation and their use for protecting industrial materials.
- Thiocarbamoyl compounds and their use in protecting materials are known and are e.g. in (DE 4 1 17 385).
- these compounds have the disadvantage that they do not always have a sufficient microbicidal action and, moreover, are washed out of the materials to be protected. Long-term protection is therefore not guaranteed by these known connections.
- R 1 , R 2 , R 3 each independently represent hydrogen or methyl
- R 4 represents cyclohexyl or cyclohexenyl
- the compounds of formula (I) are obtained by using formyl acid derivatives of formula (II) in which R and R have the meanings given above and R represents methyl, ethyl, n-, i-propyl or n-, i-, s- or t-butyl with thiosemicarbazides of the formula (III)
- 0.8 to 1.0 mol of thiosemicarbazide is preferably added per mol of ⁇ -formylacetic acid derivative.
- Sodium hydroxide, potassium hydroxide or potassium tert-butoxide, preferably in approximately equimolar amounts, are preferably added as bases
- alcohols such as ethanol or aromatic hydrocarbons such as toluene are suitable as solvents or diluents.
- the condensation reaction is carried out over a wide temperature range.
- first thiosemicarbazone formation For the first thiosemicarbazone formation,
- the cyclocondensation reaction which takes place after the addition of base is carried out at temperatures of 20 to 100 ° C., preferably 20 to 40 ° C.
- the 1-thiocarbamoyl compounds of the formula (I) according to the invention are isolated from the reaction mixtures by known methods.
- the procedure is generally such that the reaction mixtures are freed from the solvent and the residue is treated with aqueous hydrochloric acid.
- the resulting pyrazoles are separated off by suction.
- the thiosemicarbazides of the formula (III) are known or can be obtained by generally known preparation processes.
- the formyl acid derivatives of the formula (II) are new and also the subject of the application.
- bases such as NaH
- formylated in solvents or diluents such as cyclohexane and DMF
- amino acid esters such as methyl or ethyl esters.
- the formyl acid derivatives of the formula (II) are also obtained by corresponding ⁇ , ⁇ -unsaturated esters according to generally known methods, such as e.g. described in EP-417.597 or DE-2.643.205, hydroformylated.
- the active compounds of the formula (I) and the agents according to the invention have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
- the active compounds of the formula (I) and the agents according to the invention are used to protect industrial materials against
- Infestation and destruction by undesirable microorganisms are suitable and surprisingly more effective than the derivatives in which R 4 is cyclopentyl and cyclopentenyl.
- technical materials are to be understood as non-living materials that have been prepared for use in technology.
- technical materials which are to be protected from microbial change or destruction by active substances according to the invention adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials can be those of Microorganisms can be attacked or decomposed.
- parts of production plants for example cooling water circuits, may also be mentioned which can be impaired by the multiplication of microorganisms.
- the preferred technical materials are adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids. called, particularly preferably paints.
- Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
- the active substances or agents according to the invention preferably act against fungi, in particular molds, wood-staining and wood-destroying fungi (Basidiomycetes) and against mucus organisms and algae.
- microorganisms of the following genera may be mentioned:
- Alternaria such as Alternaria tenuis, Aspergillus, such as Aspergillus niger,
- Chaetomium like Chaetomium globosum
- Coniophora such as Coniophora puetana
- Lentinus such as Lentinus tigrinus
- Penicillium such as Penicillium glaucum
- Polyporus such as Polyporus versicolor
- Aureobasidium such as Aureobasidium pullulans
- Sclerophoma such as Sclerophoma pityophila
- Trichoderma like Trichoderma viride
- Escherichia such as Escherichia coli
- Pseudomonas such as Pseudomonas aeruginosa
- Staphylococcus such as Staphylococcus aureus.
- the active compounds of the formula (I) can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and very fine encapsulations in polymeric substances.
- formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
- extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
- 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.
- aromatics such as xylene, toluene, alkylnaphthalenes, chlorinated Aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, 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 or dimethyl sulfoxide, and water;
- Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide;
- Solid carrier materials are possible: for example natural rock powder, such as
- Solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; the following may be used as emulsifying and / or foaming agents: e.g.
- non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
- Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
- Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers, 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, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper,
- Cobalt, molybdenum and zinc can be used.
- the active compounds of the formula (I) according to the invention are preferably used to protect paints against attack and destruction by undesired microorganisms.
- painting is to be understood as meaning a coating made of paints on a substrate.
- the paint may have penetrated more or less into the surface. It can consist of one or more layers and can be produced by processes such as brushing, spraying, dipping, flooding or similar processes.
- the compounds of the formulas (I) are incorporated in the paints or in precursors for the preparation of the paints by customary methods, e.g. by mixing the active ingredients with the other components.
- Paints according to the invention therefore contain, in addition to at least one fungicidal active ingredient of the formula (I), customary paint components in e.g. liquid, pasty or powdery form such as
- Colorants such as pigments or dyes, preferably pigments.
- examples include titanium dioxide, zinc oxide and iron oxide.
- Binders such as, for example, oxidatively drying alkyd resins, vinyl polymers and vinyl copolymers, acrylic polymers and acrylic copolymers, plastic powders, novolaks, amino resins, polyester resins, epoxy resins, silicone resins, isocyanate resins, vinyl polymers and vinyl copolymers, acrylic polymers and other acrylic copolymers and acrylic copolymers are preferred usable binders.
- the paints may also contain the following additives
- Fillers such as heavy spar, calcite, dolomite and talc,
- Solvents such as alcohols, ketones, esters, glycol ethers and aliphatic and aromatic hydrocarbons,
- Drying agents skin contraceptives, leveling agents, anti-foaming agents, corrosion inhibitors, UV absorbers, fragrances, antistatic agents, antifreeze agents.
- the following may preferably be mentioned as paints or precursors for the production of paints:
- Plastic dispersions such as latex dispersions or dispersions based on other polymers.
- Starch products such as Pressure thickener.
- Carbon black pigments, titanium dioxide pigments) or slurries of fillers such as
- Kaolin or calcium carbonate - bitumen emulsions.
- Triazoles such as:
- Succinate dehydrogenase inhibitors such as: fenfuram, furcarbanil, cyclafluramide, furmecyclox, seedvax, metsulfovax, pyrocarbolide, oxycarboxin, shirlan, mebenil (mepronil), benodanil, flutolanil (moncut);
- Naphthalene derivatives such as terbinafine, naftifine, butenafine, 3-chloro-7- (2-aza-
- Sulfenamides such as dichlofluanid, tolylfluanid, folpet, fluorfolpet; Captan,
- Benzimidazoles such as carbendazim, benomyl, furathiocarb, fuberidazole, thiophonate methyl, thiabendazole or their salts;
- Mo ⁇ holinderivate such as Tridemo ⁇ h, Fenpropimo ⁇ h, Falimo ⁇ h, Dimethomo ⁇ h, Dodemo ⁇ h, Aldimo ⁇ h, Fenpropidin and their arylsulfonic acid salts, such as e.g. p-
- Benzothiazoles such as 2-mercaptobenzothiazole;
- Benzamides such as 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide;
- Boron compounds such as boric acid, boric acid ester, borax;
- Formaldehyde and formaldehyde releasing compounds such as benzyl alcohol mono-
- Aldehydes such as cinnamaldehyde, formaldehyde, glutardialdehyde, ⁇ -bromocinnamaldehyde;
- Thiocyanates such as thiocyanatomethylthiobenzothiazole, methylene bisthiocyanate, etc; quaternary ammonium compounds such as benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, didecyldimethaylammonium chloride; Iodine derivatives such as diiodomethyl p-tolyl sulfone, 3-iodo-2-propynyl alcohol, 4-chlorophenyl-3-iodopropargyl formal, 3-bromo-2,3-diiodo-2-propenylethyl carbamate, 2,3,3-triiodo allyl alcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propynyl-n-hexyl carbamate, 3-iodo-2-propynyl
- Phenol derivatives such as tribromophenol, tetrachlorophenol, 3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol, dichlorophen, o-phenylphenol, m-phenylphenol, p-phenylphenol, 2-benzyl-4-chlorophenol and their alkali and
- Microbicides with activated halogen group such as chloroacetamide, bronopol, bronidox, tectamer such as 2-bromo-2-nitro-l, 3-propanediol, 2-bromo-4'-hydroxy-acetophenone, 2,2-dibromo-3- nitrile propionamide, 1,2-dibromo-2,4-dicyanobutane, ⁇ -bromo- ⁇ -nitrostyrene;
- Pyridines such as l-hydroxy-2-pyridinthione (and their Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimethanol, mepanipyrim, dipyrithione, 1-hydroxy-4-methyl-6- (2nd , 4,4-trimethylpentyl) -2 (1H) pyridine;
- Metal soaps such as tin, copper, zinc naphtenate, octoate, 2-ethylhexanoate, oleate, phosphate, benzoate;
- Metal salts such as copper hydroxycarbonate, sodium dichromate, potassium dichromate, potassium chromate, copper sulfate, copper chloride, copper borate, zinc fluorosilicate, copper fluorosilicate;
- Oxides such as tributyltin oxide, Cu 2 O, CuO, ZnO; Dialkyldithiocarbamates such as Na and Zn salts of dialkyldithiocarbamates,
- Nitriles such as 2,4,5,6-tetrachloroisophthalonitrile, disodium cyano-dithioimidocarbamate;
- Quinolines such as 8-hydroxyquinoline and their Cu salts; Mucochloric acid, 5-hydroxy-2 (5H) furanone;
- Zeolites containing Ag, Zn or Cu alone or included in polymeric active substances Zeolites containing Ag, Zn or Cu alone or included in polymeric active substances.
- Fungicides Acypetacs, 2-aminobutanes, ampropylfos, anilazines, benalaxyl, bupirimate,
- Metalaxyl methasulfocarb, nitrothal-isopropyl, Nuarimol, Ofurace, Oxadiyl, Perfluorazoate, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Procymidone, Prop-amocarb, Propineb, Pyrazophos, Pyrifenox, Pyroquilon, Quintozene, Quintozene, Quintozene , Thiophanate-methyl, Tolclofos-methyl, Triazoxide, Trichlamide, Tricyclazole, Triforine, Vinclozolin.
- Phosphoric acid esters such as azinphos-ethyl, azinphos-methyl, ⁇ -l (4-chlorophenyl) -4- (O-ethyl, S-propyl) phosphoryloxy-pyrazole, Chlo ⁇ yrifos, Coumaphos, Demeton, Demeton-S-methyl, diazinon, dichlorvos, Dimethoate, Ethoate, Ethoprophos, Etrimfos, Fenitrothion, Fenthion, Heptenophas, Parathion, Parathion-methyl,
- Phosalones Phoxim, Pirimiphos-ethyl, Pirimiphos-methyl, Profenofos, Prothiofos, Sulfprofos, Triazophos and Trichlo ⁇ hon; Carbamates such as aldicarb, bendiocarb, ⁇ -2- (l-methylpropyl) phenylmethyl carbamate, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Isoprocarb, Methomyl, Oxamyl, Pirimicarb, Promecarb, Propoxur and Thiodicarb; Organosilicon compounds, preferably dimethyl (phenyl) silyl-methyl-3-phenoxybenzyl ether such as dimethyl- (4-ethoxyphenyl) -silylmethyl-3-phenoxybenzylether or
- (Dimethylphenyl) silylmethyl-2-phenoxy-6-pyridylmethyl ether such as e.g. Dimethyl- (9-ethoxy-phenyl) -silylmethyl-2-phenoxy-6-pyridylmethylether or [(phenyl) -3- (3-phenoxyphenyl) -propyl] (dimethyl) -silanes such as e.g.
- N-nitro-1H-imidazole-2-amine (imidacloprid), N - [(6-chloro-3-pyridyl) methyl-] N 2 - cyano-N'-methylacetamide (NI-25);
- Fentin acetates metaldehydes, methiocarb.
- Niclosamide thiodicarb, trimethacarb.
- Algicide Coppersulfate, dichlororphen, Endothal, Fentinacetate, Quinoclamine.
- Herbicides acetochlor, acifluorfen, aclonifen, acrolein, alachlor, alloxydim, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam atrazine, aziptrotryne, benazolin, benfluralin, benfuresate, bensulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfonon, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron, benzenesulfuron borax, dichlo ⁇ rop, dichlorprop-P, diclofop, diethatyl, difenoxuron
- DPX-E96361, DSMA eglinazine, endothal, EPTC, esprocarb, ethalfluralin, ethidimuron, ethofumesate, fenoxaprop, fenoxaprop-P, fenuron, flamprop, flamprop-M, flazasulfuron, fluazifop, fluazifop-P, fluchloronalonium, fluorofuronaline, flumofenyluron, flumofenol, flumofenol flupropanate, flurenol, fluridone, flurochloridone, fluoroxypyr, cycloate, cycloxydim, 2,4-D, daimuron, dalapon, dazomet, 2,4-DB, desmedipham, desmetryn, dicamba, dichlorobile, isoproturon, isouron, isoxaben, isoxapyrifop lenac
- the weight ratios of the active ingredients in these active ingredient combinations can be varied within relatively large ranges.
- the active compound combinations preferably contain the active compound of the formula (I) in an amount of 0.1 to 99.9%, in particular 1 to 75%, particularly preferably 5 to 50%, the remainder being filled 100% by one or more of the above-mentioned mixing partners .
- microbicidal agents or concentrates used to protect the industrial materials contain the active ingredient or combination of active ingredients in a concentration of 0.01 and 95% by weight, in particular 0.1 to 60% by weight.
- the application concentrations of the active ingredients to be used or the active ingredient combinations depend on the type and the occurrence of the microorganisms to be controlled and on the composition of the material to be protected.
- the optimal amount can be determined by test series.
- the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.
- the active substances or agents according to the invention advantageously make it possible to replace the microbicidal agents available hitherto with more effective ones. They show good stability and advantageously have a broad spectrum of activity.
- the substance to be tested for its fungicidal activity is incorporated in the desired concentration in the (dispersion) color using a dissolver.
- the paint is then spread on both sides on a suitable surface.
- test specimens are leached with running water (24 h; 20 ° C) before the test for mold resistance.
- test specimens thus prepared are placed on an agar culture medium.
- Test specimens and culture medium are contaminated with types of fungus. After storage for 1 to 3 weeks at 29 + 1 ° C and 80 to 90% rel. Humidity is checked.
- the paint is permanently mold-resistant if the test specimen remains free of fungi or if at most a slight edge infestation can be seen.
- Fungus spores of the following nine molds which are known as paint destroyers or are often found on paints, are used for contamination:
- the following table shows the active ingredient concentrations at which the paint sample remains fungus-free (concentrations based on the solids content of the
- Emulsion paint The Emulsion paint.
- Comparative Example A Comparative Example B:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP96906748A EP0815085A1 (de) | 1995-03-20 | 1996-03-07 | Thiocarbamoylverbindungen |
AU50038/96A AU5003896A (en) | 1995-03-20 | 1996-03-07 | Thiocarbamoyl compounds |
JP8528029A JPH11502207A (ja) | 1995-03-20 | 1996-03-07 | チオカルバモイル化合物 |
MXPA/A/1997/006968A MXPA97006968A (en) | 1995-03-20 | 1997-09-12 | Composite of tiocarbamo |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19510058.1 | 1995-03-20 | ||
DE1995110058 DE19510058A1 (de) | 1995-03-20 | 1995-03-20 | Thiocarbamoylverbindungen |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1996029314A1 true WO1996029314A1 (de) | 1996-09-26 |
Family
ID=7757167
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1996/000971 WO1996029314A1 (de) | 1995-03-20 | 1996-03-07 | Thiocarbamoylverbindungen |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0815085A1 (de) |
JP (1) | JPH11502207A (de) |
AU (1) | AU5003896A (de) |
DE (1) | DE19510058A1 (de) |
WO (1) | WO1996029314A1 (de) |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4117385A1 (de) * | 1991-05-28 | 1992-12-03 | Bayer Ag | Verwendung von 1-thiocarbamoyl-5-hydroxy-pyrazolen als mikrobizide, neue 1-thiocarbamoyl-5-hydroxy-pyrazole und verfahren zu ihrer herstellung |
EP0638556A1 (de) * | 1993-08-11 | 1995-02-15 | Bayer Ag | Arzneimittel enthaltend 1-Thiocarbamoyl-5-hydroxypyrazolen und deren Verwendung als Mittel zur Bekämpfung des septischen Schocks |
WO1995004722A1 (de) * | 1993-08-11 | 1995-02-16 | Bayer Aktiengesellschaft | Thiocarbamoylverbindungen als mikrobizide |
-
1995
- 1995-03-20 DE DE1995110058 patent/DE19510058A1/de not_active Withdrawn
-
1996
- 1996-03-07 JP JP8528029A patent/JPH11502207A/ja active Pending
- 1996-03-07 EP EP96906748A patent/EP0815085A1/de not_active Withdrawn
- 1996-03-07 WO PCT/EP1996/000971 patent/WO1996029314A1/de not_active Application Discontinuation
- 1996-03-07 AU AU50038/96A patent/AU5003896A/en not_active Abandoned
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4117385A1 (de) * | 1991-05-28 | 1992-12-03 | Bayer Ag | Verwendung von 1-thiocarbamoyl-5-hydroxy-pyrazolen als mikrobizide, neue 1-thiocarbamoyl-5-hydroxy-pyrazole und verfahren zu ihrer herstellung |
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Also Published As
Publication number | Publication date |
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AU5003896A (en) | 1996-10-08 |
EP0815085A1 (de) | 1998-01-07 |
MX9706968A (es) | 1997-11-29 |
JPH11502207A (ja) | 1999-02-23 |
DE19510058A1 (de) | 1996-09-26 |
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