Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
• • 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
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
  • C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
  • C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
  • C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
  • C07D279/08—1,3-Thiazines; Hydrogenated 1,3-thiazines condensed with carbocyclic rings or ring systems

Definitions

• the present invention relates to new thiazines, processes for their preparation and their use for controlling unwanted microorganisms, new
• the thiazines of the general formula (1) according to the invention have better fungicidal activity than the constitutionally most similar, known substances. Furthermore, it was found that the new thiazines of the general formula (I) are very suitable for protecting industrial materials against attack by microorganisms.
• the present invention relates to thiazines of the general formula (I)
• R 1 for hydrogen or for optionally substituted alkyl, aryl or
• R 2 to R 7 independently of one another represent hydrogen or represent optionally substituted alkyl, aryl or cycloalkyl, at least one of the substituents R 2 to R 7 being different from hydrogen,
• alkyl radicals mentioned are straight-chain or branched, unsubstituted or substituted and contain 1 to 12 C atoms, in particular 1 to 8 C atoms.
• Preferred alkyl radicals are methyl, ethyl, butyl and octyl.
• Cycloalkyl generally represents an unsubstituted or substituted cycloalkyl radical having 3 to 8 C atoms, in particular 3 to 7 C atoms. Cyclopropyl and cyclohexyl are preferred.
• Aryl generally represents a substituted or unsubstituted aromatic radical, in particular phenyl and naphthyl.
• Halogen generally represents fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine and bromine.
• Heterocyclyl stands for a saturated, unsaturated or aromatic substituted or unsubstituted 5 to 7-membered ring, in particular 5 or 6-membered ring, with one or more identical or different heteroatoms, in particular with 1 to 4 heteroatoms and preferably with 1 to 3 heteroatoms , Heteroatoms are in particular N, O and S, preferably N and S. If appropriate, a further carbocyclic ring is fused onto the heterocyclyl radical, in particular one 6-membered carbocyclic ring, preferably a 6-membered aromatic ring.
• the term carbocyclic ring stands for a saturated or mono- to polyunsaturated, substituted or unsubstituted carbocyclic ring with 3 to 12 carbon atoms, in particular 3 to 8 carbon atoms.
• radicals are optionally substituted 1 to more times, identically or differently, in particular 1 to 5 times, preferably 1 or 3 times, the following being suitable in each case: halogen, in particular fluorine, chlorine, bromine; Alkyl, in particular -CC 8 alkyl; Cycloalkyl, especially C 3 -C 8 cycloalkyl; Haloalkyl, in particular C 1 -C 6 haloalkyl; Alkoxy, especially Ci-Ce-alkoxy;
• Haloalkoxy in particular Ci-C ⁇ -haloalkoxy; nitro; nitrilo; Arnino; Alkylamino or DiaJJylamino (collectively referred to as (di) alkylamino, in particular (D ⁇ -CrC ö alkylamino; hydroxy; phenyl, biphenyl; naphthyl; phenoxy and phenoxyphenyl.
• R 1 for hydrogen or for in each case optionally substituted C 1 -C 4 -alkyl, C 6 -C 10 -aryl or 5- to 7-membered heterocyclyl having 1 to 4 identical or different heteroatoms, which optionally have one condensed on
• R 2 to R 7 independently of one another represent hydrogen or represent optionally substituted CrC ⁇ alkyl, C 6 -C 10 aryl or C 3 -C 8 cycloalkyl, at least one of the substituents R 2 to R 7 being different from hydrogen .
• substituents from the R 2 to R 7 series together with the C atoms to which they are attached represent an optionally substituted 3 to 12-membered carbocyclic ring and the remaining substituents from the R 2 to R 7 series are hydrogen stand.
• R 1 for hydrogen, optionally 1- to 5-fold, identical or different by halogen, QC ö alkoxy, Ci-C ⁇ -haloalkyl or Ci-C ö haloalkoxy-substituted C 1 -C 8 alkyl, for 1- up to 3 times, identical or different, by halogen, Ci-Cs-alkyl, Ci-Cg-alkoxy, C j -Cg-haloalkyl, C j -Cg-haloalkoxy, hydroxy, nitro, nitrilo, amino, (di) -C ⁇ -C 6 - alkylamino, C3-Cg-cycloalkyl, phenyl or phenoxy-substituted C 6 -C 10 - aryl, or for 5- to 6-membered heterocyclyl with 1 to 3 identical or different heteroatoms from the series N, O, S, which optionally contains a fused-on aromatic 6-ring and which is optionally substituted by Ci
• R 2 to R 7 independently of one another for hydrogen, for optionally 1 to 5 times, identical or different by halogen, -C -C 6 - haloalkyl or C ⁇ -C ⁇ -haloalkoxy substituted CrC ⁇ alkyl, optionally 1 to 5 times, the same or different by halogen, C j -Cg alkyl, C ⁇ Cg alkoxy, Ci-C ö -haloalkyl or -
• R 1 for hydrogen, optionally 1 to 3 times, identical or different by fluorine, chlorine, bromine, CrCs-alkoxy, C 1 -C -haloalkyl or Ct-C 2 - haloalkoxy substituted -CC 8 alkyl or for each optionally 1- to 3-fold, identical or different by fluorine, chlorine, bromine, d-Cs-alkyl, C 1 -C 3 alkoxy, C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy, hydroxy Nitro
• Nitrilo amino, (D -Ci-Cs-alkylamino, C 3 -Cg-cycloalkyl, phenyl or phenoxy-substituted phenyl or naphthyl, or for 5- or 6-membered heterocyclyl with 1 or 2 identical or different heteroatoms from the Row N, O, S, which optionally contains a fused aromatic 6-ring and which is optionally substituted by C 1 -C 6 -alkyl,
• R 2 to R 7 are independently hydrogen, optionally 1 to 3 times by identical or different fluorine, chlorine, bromine, Q-Cs alkoxy, C ⁇ -C 2 haloalkyl, or C 1 -C 2 -haloalkoxy-substituted CrCs-alkyl, optionally substituted 1 to 3 times, identically or differently by fluorine, chlorine, bromine, C r C 4 alkyl, C r C 4 alkoxy dC 2 - haloalkyl or C 1 -C 2 haloalkoxy or for optionally 1 to 3 times, identical or different by fluorine, Chlorine, bromine, C 1 -C 4 alkyl, C r C 4 alkoxy C 1 -C 2 haloalkyl or C ⁇ -C 2 haloalkoxy, C 3 -C substituertes -cycloalkyl, wherein at least one of the substituents R to R of Hydrogen is different
• Halogenalkoxy substituted 3- to 8-membered carbocyclic ring and the remaining substituents from the series R 2 to R 7 are hydrogen.
• R 2 and R 3 independently of one another represent optionally substituted alkyl, preferably dC ⁇ alkyl and in particular CrCs alkyl;
• R represents optionally substituted alkyl, cycloalkyl or aryl, preferably C ⁇ -Ci 2 -alkyl, C 3 -C 8 cycloalkyl or optionally mono- or polysubstituted by identical or different substituents from halogen, C ⁇ -C 8 alkyl or C ⁇ -C 6 - Alkoxy-substituted phenyl, and in particular represents Ci-Cg-alkyl, C 3 -C 7 -cycloalkyl or optionally 1 to 3 times, identical or different phenyl substituted by chlorine, bromine, fluorine, Q-Giralkyl or CrQ-alkoxy;
• R 4 represents optionally substituted alkyl and R 5 represents hydrogen or optionally substituted alkyl, preferably R 4 represents C1-C 12 alkyl and R 5 represents hydrogen or C 1 -C 2 -alkyl and in particular R 4 represents C 1 -C 8 - Alkyl and R 5 represents hydrogen or d-Cs-alkyl;
• R 4 stands for optionally substituted aryl or cycloalkyl, preferably for C 3 -C 8 cycloalkyl or optionally phenyl substituted one or more times or identically or differently by halogen, CrCg-alkyl or Ci-C ö alkoxy, and in particular for C 3 -C 7 cycloalkyl or optionally 1- to 3-fold, identical or different phenyl substituted by chlorine, bromine, fluorine, Ci-Cs-alkyl, d-Cs-alkox;
• R 7 represents optionally substituted alkyl, aryl or cycloalkyl, preferably C 1 -C 2 alkyl, C 3 -C 8 cycloalkyl or phenyl which is substituted one or more times by the same or different means by halogen, CrCs alkyl or CC 6 alkoxy stands, and in particular for Ci-Cs-alkyl, C 3 - C 7 cycloalkyl or optionally 1 to 3 times, identically or differently by chlorine, bromine, fluorine, Ci-Cg-alkyl, CrC 3 -alkoxy substituted phenyl ;
• R 6 and R 7 independently of one another represent optionally substituted alkyl, preferably represent C 1 -C 12 -alkyl, and in particular represent CrCg-alkyl;
• R and R independently of one another represent optionally substituted alkyl, preferably stand, and in particular stand for C Cs-alkyl;
• R 2 , R 3 and R 7 independently of one another are optionally substituted alkyl and R 6 is hydrogen or optionally substituted alkyl, preferably R 2 , R 3 and R 7 are dC 12 alkyl and R 6 is hydrogen or dC 12 - Is alkyl, and in particular R 2 , R 3 and R 7 are d-Cs-alkyl and R 6 is hydrogen or -CC 8 alkyl;
• R 3 and R 4 together with the C atoms to which they are attached represent an optionally substituted carbocyclic ring, preferably a 3 to 12-membered carbocyclic ring, and in particular a 3 to 8-membered carbocyclic ring ;
• R 5 and R 6 together with the carbon atoms to which they are attached represent an optionally substituted carbocyclic ring, stand for a 3- to 12-membered carbocytic ring and in particular a 3- to 8-membered carbocyclic ring.
• Some of the compounds of the general formula (I) can be present as ice or trans isomers. This invention relates both to the isomer mixtures and to the isomerically enriched or isomerically pure compounds obtained by chromatographic methods.
• the new compounds of formula (I) can be prepared by reacting mercaptans of formula (II) or their salts
• R 1 has the meaning given above
• R 2 to R 7 have the meanings given above,
• R 1 has the meaning described above
• R 1 has the meaning given above
• X represents halogen or a leaving group
• R to R have the meanings described above,
• the present invention furthermore relates to the preparation of the new intermediates of the general formula (V) by reacting compounds of the general formula (VII) or their salts
• R 2 to R 7 have the meanings described above,
• X represents halogen or leaving group
• the salts can be prepared and reacted in situ or used in bulk.
• the alkali and alkaline earth metal salts preferably the alkali metal salts and particularly preferably the sodium and potassium salts can be used as salts.
• the salts are prepared using common chemical methods.
• the starting materials of the general formula (II), (IV) and (NI) are commercially available, described in the literature or can be prepared by simple chemical operations.
• the compounds of the general formulas (III) or (V) and (VII) can, if appropriate, be generated in situ and reacted directly or used as a pure substance.
• Possible diluents added are both water and all customary inert organic solvents. These preferably include hydrocarbons such as toluene, xylene or hexane, chlorinated hydrocarbons such as chlorobenzene, methylene chloride or chloroform, ketones such as acetone or butanone, ethers such as tetrahydrofuran, diethyl ether, methyl tert-butyl ether, dimethoxyefhan or dioxane, nitriles such as acetonitrile , Amides such as ⁇ , ⁇ -dimethylformamide, N, N-dimethylacetamide or N-methylpyrolidone, sulfoxides such as dimethyl sulfoxide, sulfones such as sulfolane, and esters such as ethyl acetate or
• reaction temperatures can be varied over a wide temperature range in the manufacturing process. In general, one works between -30 ° C and + 150 ° C, preferably between 0 ° C and + 110 ° C.
• 1 mol of the starting material of the general formula (ITI) or (V) or (VII) is generally 1 to 10 mol, preferably 1 to 5 mol, of the compounds of the general formula (II) or . (TV) or (VI) on.
• the processing takes place according to the usual methods.
• Both organic and inorganic bases can be used as acid scavengers.
• Suitable inorganic bases are carbonates, hydroxides, phosphates and hydrides of the alkali, alkaline earth and transition metals; preference is given to using the carbonates, hydroxides and hydrides of the alkali and alkaline earth metals.
• Primary, secondary and tertiary amines can be used as organic bases. Tertiary amines such as trimethylarnine, triethylamine, tributylamine, DBU, DBN and pyridine, N, N-dimethylaniline or N, N-dimethylpyridine are preferred.
• the diazotizations can be carried out in the presence of an alkali metal nitrite or an alkyl nitrite.
• alkali metal nitrites can be used as the alkali metal nitrite; sodium or potassium nitrite is preferably used.
• All customary alkyl nitrites preferably having 1 to 10 carbon atoms, in particular methyl nitrite, ethyl nitrite, n-propyl nitrite, i-
• Propyl nitrite and isoamyl nitrite can be used. Copper, copper salts, palladium or palladium salts can be used as the catalyst for the diazotization. Copper chips, copper (I) iodide, palladium (II) acetate or tetrakis (triphenylphoshin) palladium (O) are preferred.
• the process according to the invention is generally carried out at atmospheric pressure. However, it is also possible to work at reduced or increased pressures, in the range from 0.1 to 10 bar.
• esters of sulfonic acids in particular mesylates, can be used as leaving groups.
• Tosylates or triflates can be used.
• Lewis acids in particular soft Lewis acids according to the HSAB concept, or N, N-dimethylaminopyridine can optionally be used as catalysts.
• the present invention also relates to the metal salts and acid addition compounds of the compounds of the general formula (I).
• Preferred metal salts are salts of metals from II to IN.
• Suitable anions of the salts are those which can preferably be derived from the following acids: hydrohalic acids, e.g. Hydrochloric acid and hydrobromic acid, also phosphoric acid, nitric acid and sulfuric acid.
• the metal salt complexes of the compounds of the general formula (I) can be obtained in a simple manner by customary processes, e.g. by dissolving the metal salt in
• Alcohol e.g. Ethanol and adding to compounds of general formula (I).
• the metal salt complexes can be prepared in a known manner, e.g. isolate by filtering and if necessary clean by recrystallization.
• Formula (I) preferably includes the following acids: the hydrohalic acids, e.g. Hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, also phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, e.g. Acetic acid, propionic acid, 2-ethylhexanoic acid, butyric acid, mandelic acid, oxalic acid,
• the hydrohalic acids e.g. Hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, also phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, e.g. Acetic acid, propionic acid, 2-ethylhexanoic acid, butyric acid, mandelic acid, oxalic acid,
• Succinic acid 2-hydroxy-ethane-dicarboxylic acid, maleic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid, lactic acid and sulfonic acids, such as e.g. p-toluenesulfonic acid, 1,5-naphthalenedisulfonic acid, alkanesulfonic acids, benzoic acid and optionally substituted benzoic acids.
• the acid addition salts of the compounds of the general formula (I) can be obtained in a simple manner by customary salt formation methods, for example by dissolving a compound of the general formula (I) in a suitable inert solvent and adding the acid, for example hydrochloric acid, and in a known manner , for example by filtration, isolated and, if necessary, cleaned by washing with an inert organic solvent.
• the compounds of the formula (I) have a strong microbicidal action and can be used to control unwanted microorganisms, such as, for example, fungi, bacteria and algae.
• the compounds of the general formula (I) are preferably used to combat undesirable microorganisms in material protection.
• the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
• technical materials are understood to mean non-living materials that have been prepared for use in technology.
• the technical materials are adhesives, glues, paper and cardboard, textiles, leather, wood, wood-based materials, paints and plastic articles, cooling lubricants and other materials by
• Microorganisms can be attacked or decomposed. Furthermore, technical materials within the scope of the present invention also include parts of production plants, for example cooling water circuits, which can be impaired by the multiplication of microorganisms.
• Technical materials that are preferably to be protected are adhesives, glues, papers and cartons,
• the compounds of the general formula (I) according to the invention are particularly suitable for protecting wood, plastics, cooling lubricants and coating systems such as paints, varnishes or renders against attack by microorganisms.
• the compounds of the general formula (I) according to the invention are very particularly suitable for protecting wood, plastics and coating systems such as paints, varnishes or plasters from attack by microorganisms.
• 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 compounds of the general formula (I) according to the invention preferably act against fungi, in particular molds, wood-staining and wood-destroying fungi (Basidiomycetes) and against mucus organisms and algae.
• the action of the active compounds of the general formula (I) as film fungicides is particularly preferred.
• Microorganisms of the following genera may be mentioned, for example:
• 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 ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
• formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
• extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate 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.
• water e.g. organic solvents can also be used as auxiliary solvents.
• aromatics such as xylene, toluene or alkylnaphthalenes
• chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
• aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. 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 and dimethyl sulfoxide, and water.
• Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
• Possible solid carriers are: e.g. natural rock powders such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates. As fixed
• Carriers for granules are possible: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
• Suitable emulsifiers and / or foam-generating agents are: for example nonionogenic 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.
• Possible dispersing agents are, for example, lignin sulfite waste 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 also 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 formulations generally 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 in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the activity spectrum or to prevent the development of resistance. In many cases, synergistic effects are obtained, ie the effectiveness of the mixture is greater than the effectiveness of the individual components.
• the effectiveness and the spectrum of activity of the active compounds of the general formula (I) or the agents, precursors or very generally formulations which can be prepared therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active compounds are used to enlarge the spectrum of action or achieving special
• Triazoles such as:
• Imidazoles such as:
• Clotrimazole Bifonazole, Climbazole, Econazole, Fenapamil, Imazalil, Isoconazole, Ketoconazole, Lombazole, Miconazole, Pefurazoate, Prochloraz, Triflumizole, Thiazolcar l-Imidazolyl-l- (4'-chlorophenoxybutyl) -3,3 their
• Succinate dehydrogenase inhibitors such as:
• Naphthalene derivatives such as:
• Sulfenamides such as:
• Dichlorfluanide tolylfluanid, folpet, fluorfolpet; Captan, Captofol;
• Benzimidazoles such as:
• Morpholine derivatives such as:
• Tridemorph, trimorphamide and their arylsulfonic acid salts e.g. p-toluenesulfonic acid and p-dodecylphenyl sulfonic acid;
• Benzthiazoles such as:
• Formaldehyde and formaldehyde releasing compounds such as:
• Isothiazolinones such as:
• Aldehydes such as:
• Benzalkonium chloride ben ⁇ yldimemyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, DicWorbenzyl-dimemyl-alkyl-ammonium chloride, Di-decyldimethylammonium chloride, Dioctyl-dimethyl-ammonium chloride, N-Hexadecyl-trimethyl-ammonium chloride, 1-hexadino-chloride (1-hexidine) albesilate);
• Iodine derivatives such as:
• Phenols such as:
• Microbicides with activated halogen group such as: Bronopol, Bronidox, 2-bromo-2-nitro-1,3-propanediol, 2-bromo-4'-hydroxy-acetophenone, 1-bromo-3-chloro-4,4,5,5-tetramethyl-2 -imidazoldinone, ß-bromo-ß-nitrostyrene, chloroacetamide, chloramine T, l, 3-dibromo-4,4,5,5-tetrametyl-2-imidazoldinone, dichloroamine T, 3,4-dichloro- (3H) -l, 2-dithiol-3-one, 2,2-dibromo-3-nitrile-propionamide, l, 2-dibromo-2,4-dicyanobutane, halanes, halazones, mucochloric acid, phenyl- (2-chloro-cyan- vinyl) sulfone, phenyl- (1
• Azoxystrobin Dimoxystrobin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Trifloxystrobin, 2,4-dihydro-5-methoxy-2-memyl-4- [2 - [[- [[((trifluoromemyl ) phenyl] e ylidenes] amino] oxy] methyl] phenyl] -3H-l, 2,4-triazol-3-one (CAS No. 185336-79-2)
• Salts of the metals tin, copper and zinc with higher fatty, resin, naphthenic and phosphoric acids such as e.g. Tin, copper, zinc naphtenate, octoate, 2-ethylhexanoate, oleate, phosphate, benzoate;
• Metal salts such as:
• Oxides of the metals tin, copper and zinc such as Tributyltin oxide, CU2O, CuO, ZnO;
• Oxidizing agents such as:
• Cufraneb ferban, potassium N-hydroxymethyl-N'-methyl-dithiobarbamate, Na- or K-dimethyldithiocarbamate, Macozeb, Maneb, Metam, Metiram, Thiram, Zineb, Ziram;
• Nitriles such as:
• Diflumetorin Diflumetorin, Quinoxyfen, Famoxadone, Polyoxorim, Acibenzolar-S-methyl, Furametpyr, thifluzamide, methalaxyl-M, benthiavalicarb, metrafenone, cyflufenamid, tiadinil, tea tree oil, phenoxyethanol,
• Zeolites containing Ag, Zn or Cu alone or enclosed in polymeric materials Zeolites containing Ag, Zn or Cu alone or enclosed in polymeric materials.
• Aldoxycarb Aldrin, Allethrin, Alpha-cypermethrin, Amidoflumet, Amitraz, Avermectin, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
• Fenamiphos Fenazaquin, Fenbutatinoxid, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fensulfothion, Fenthion, Fenvalerate, Fipronil, Flonicamid, Fluacrypyrim, Fluazuron,
• Flucycloxuron Flucythrinate, Flufenerim, Flufenoxuron, Flupyrazofos, Flufenzine, Flumethrin Flufenprox, Fluvalinate, Fonophos, Formethanate, Formofhion, Fosmethilan Fosthiazat, Fubfenprox, Furathiocarb,
• Halofenocid HCH (CAS RN: 58-89-9), heptenophos, hexaflumuron, hexythiazox,
• Parathion A Parathion M, Penfluron, Permethrin, 2- (4-phenoxyphenoxy) ethyl ethyl carbamate, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Prallethrin, Profenophos, Promecarb, Propaphos Propoxur, prothiophos, prothoat, pymetrozin, pyrachlophos,
• Benzofencap Benzthiazuron, Bifenox, Bispyribac, Bispyribac-Sodium, Borax, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butamifos, Butralin, Butylate, Bialaphos, Benzoyl-prop, Bromobutide, Butroxydim,
• Carbetamides carfentrazone-ethyl, carfenstrole, chloromethoxyfen, chloramben,
• Diclosulam Dichlorprop, Dichlorprop-P, Diclofop, Diethatyl, Difenoxuron, Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethipin, Dinitramine, Dinoseb, Dinoseb Acetate, Dinoterb, Dithonidhen, Dithhenamid , 2,4-D, Daimuron, Dalapon, Dazomet, 2,4-DB, Desmedipham, Desmetryn, Dicamba, Dichlobenil, Dimethamid, Dithiopyr, Dimethametryn,
• the weight ratios of the active substances in these combinations of active substances can be varied within relatively large ranges.
• the active compound combinations preferably contain from 0.1 to 99.9%, in particular from 1 to 75%, particularly preferably from 5 to 50%, the remainder being added
• 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 1.5% 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 to date with more effective ones. They show good stability and advantageously have a broad spectrum of activity.
• the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc.
• MIC minimum inhibitory concentrations
• the active compounds according to the invention were each added to an agar which was produced using malt extract in concentrations of 0.1 mg / 1 to 5,000 mg / 1. After the agar had solidified, it was contaminated with pure cultures of the test organisms listed in Table 3. After a 2-week incubation period at 28 ° C and 60 to 70% relative humidity, the MIC was determined. The MIC is the lowest active substance concentration at which no growth occurs due to the microbe species used, it is shown in Table 2.
• the adhesive to be tested was coated on both sides on a suitable base. In order to obtain practical results, some of the test specimens were leached with running water (24 h, 20 ° C) before the test for mold resistance; another part was treated with a warm fresh air stream (7 days, 40 ° C).
• the samples prepared in this way were then placed on an agar culture medium and both the sample and culture medium were contaminated with fungal spores. After 2-3 weeks of storage (29 ⁇ 1 ° C, 80-90% rel. Air humidity) the samples were taken.
• the paint is classified as permanently mold-resistant if the sample remains free of fungus or if there is at least a small amount of edge infestation.
• Fungus spores of the following molds which are known as paint destroyers or are frequently found on paints, were used for the contamination:
• Coatings according to recipe A are mold-resistant (even after leaching and exposure to the wind tunnel) if, for example, they contain 1.5% (based on solids) of example compound 47.
• Recipe A exterior emulsion paint based on Acroal 290 D (styrene acrylate)
• Solids content 135.5 61.6%.

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• 2002
  • 2002-07-29 DE DE10234425A patent/DE10234425A1/de not_active Withdrawn
• 2003
  • 2003-07-14 WO PCT/EP2003/007587 patent/WO2004013113A1/de not_active Application Discontinuation
  • 2003-07-14 AU AU2003250049A patent/AU2003250049A1/en not_active Abandoned
  • 2003-07-14 BR BR0313466-0A patent/BR0313466A/pt not_active IP Right Cessation
  • 2003-07-14 EP EP03766161A patent/EP1527054A1/de not_active Withdrawn
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  • 2003-07-14 US US10/522,865 patent/US20060089352A1/en not_active Abandoned
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