Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
  • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
  • C07D487/04—Ortho-condensed systems
• • 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
  • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

• the present application relates to new uses of known triazolopyrimidine derivatives as micxobicides for protecting industrial materials, and to new microbicidal agents and new microbicidal mixtures comprising these compounds.
• US Pat. No. 5,985,883 also describes triazolopyrimidine derivatives which are substituted by 2,4,6-trichlorophenyl in the 6-position of the pyrimidine ring for protecting plants from attack by phytopathogenic fungi.
• the present invention relates to the use of triazolopyrimidine derivatives of the formula (I)
• R 1 represents optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl
• R 2 represents hydrogen or alkyl
• R 1 and R 2 together with the nitrogen atom to which they are attached represent an optionally substituted heterocyclic ring
• R 3 represents optionally substituted aryl
• R 4 represents hydrogen or halogen
• the 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 and preferably 1 to 4 C atoms.
• Particularly preferred Alkyl residues are methyl, ethyl and propyl.
• the alkenyl and alkynyl radicals mentioned are in each case straight-chain or branched, in each case unsubstituted or substituted and each contain 2 to 12 C atoms, in particular 2 to 8 C atoms and preferably 2 to 5 C atoms. Pentenyl and propynyl are particularly preferred.
• Cycloalkyl generally represents an unsubstituted or substituted cycloalkyl radical
• cycloalkyl radicals are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cyclooctyl.
• Aryl generally represents an unsubstituted or substituted 6 to 10-membered aromatic radical, in particular phenyl.
• Halogen generally represents fluorine, chlorine, iodine or bromine, in particular fluorine, chlorine or bromine.
• heterocyclic ring in the definition of R 1 and R 2 generally means a substituted or unsubstituted 3- to 10-membered heterocyclic ring which is saturated or mono- or polyunsaturated and which has at least one nitrogen atom and, if appropriate contains a further 1 to 3 heteroatoms from the series N, O, S.
• the above-mentioned radicals are each optionally substituted 1 to 5 times, preferably 1 to 5 times, in particular 1 to 3 times, identically or differently by halogen, C 1 -C 8 -alkyl, C 1 -C 1 -haloalkyl, Ci-Cio-halogen - alkoxy, phenyl, phenoxy, benzyl or benzyloxy.
• R 1 stands for C j -Cg-alkyl, which is optionally substituted one or more times, identically or differently by halogen, phenyl or -CC 6 -haloalkyl, stands for C 3 -C 8 cycloalkyl, which is optionally one or more is substituted alkyl, C ⁇ -C 6 haloalkyl, or phenyl, or represents C2-Cg-alkenyl or C2-Cg alkynyl, - more times, identically or differently, by halogen, C I -C east
• R 2 represents hydrogen or C -C 8 alkyl
• R 1 and R 2 together with the N atom to which they are attached represent a three- to eight-membered heterocyclic ring which is optionally substituted by phenyl or Ci- - alkyl,
• R 3 represents phenyl which is optionally substituted one or more times, identically or differently, by halogen, Cj-Cg-alkyl, Ci-Cg alkoxy, Phenyl or phenoxy,
• R 4 represents hydrogen, chlorine, fluorine or bromine.
• R 1 stands for C1-C4-alkyl, which is optionally substituted one to three times, identically or differently by fluorine, chlorine, bromine or trifluoromethyl, stands for C3-Cg-cycloalkyl, which optionally represents one to three times, identically or differently C j -CSS-alkyl, fluorine, chlorine, bromine or trifluoromethyl, or C2-C5 alkenyl, or C2-C5-alkinyl,
• R 2 represents hydrogen or C r C 3 alkyl
• R 1 and R 2 together with the nitrogen atom to which they are attached represent a five- to seven-membered heterocyclic ring which is optionally substituted by C 1 -C 3 -alkyl or phenyl,
• R 3 represents phenyl, which is optionally substituted 1 to 5 times, identically or differently, by halogen, C 1 -C 4 -alkyl, C 1 -C 3 -alkoxy, Cj-C2-
• Haloalkyl, -CC 2 haloalkoxy, phenyl or phenoxy and R 4 represents chlorine or bromine.
• R 1 represents methyl, ethyl, propyl, trifluoropropyl, 2- (l, l, l-trifluoropropyl), benzyl, pentenyl, propinyl, cyclopropyl, cyclopentyl, trimethylcyclopentyl, cyclohexyl, trimethylcyclohexyl or cyclooctyl,
• R 2 represents hydrogen, methyl or ethyl
• R 1 and R 2 together with the nitrogen atom to which they are attached for
• R 4 represents chlorine.
• the radicals specified in the respective definitions or preferred and particularly preferred definitions can be replaced as desired by radical definitions of other combinations, regardless of the combination specified in each case.
• residual definitions from any preferred area can also be omitted.
• the present invention also relates to the metal salts, the acid addition compounds, the N-oxides, which, if a chiral center is present, optionally enriched (R) and (S) isomers, and also their racemates, of the compounds having the general formula (I ) as microbicides to protect technical materials.
• Preferred metal salts are salts of metals from main groups II to IV and from groups I and II and from IV to VIII of the periodic table, copper, zinc, manganese, magnesium, tin, iron,
• Calcium, aluminum, lead, chromium, cobalt and nickel may be mentioned as examples.
• Anions of the salts are those which are preferably derived from the following acids: hydrohalic acids, e.g. Hydrochloric acid and hydrobromic acid, also phosphoric acid, nitric acid and
• 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.
• Hydrohalic acids such as hydrochloric acid and hydrobromic acid, especially hydrochloric acid, also phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as acetic acid, propionic acid, 2-ethylhexanoic acid, butyric acid, mandelic acid, oxalic acid, succinic acid, 2-hydroxy-ethane-dicarboxylic acid, maleic acid, fumaric acid - acid, tartaric acid, citric acid, salicylic acid, sorbic acid, lactic acid and
• Sulfonic acids 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 general formula (I) can be easily prepared by conventional salt formation methods, e.g. by solving one
• Compound of general formula (I) in a suitable inert "solvent and adding the acid, for example hydrochloric acid, can be obtained and, for example, filtration in a known manner by Ab, isolated and optionally purified by washing with an inert organic solvent.
• the substances of the formula (I) which can be used according to the invention surprisingly have a strong microbicidal action and can be used to control undesirable microorganisms, such as fungi and bacteria, in the protection of materials.
• the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
• technical materials are to be understood as non-living materials that have been prepared for use in technology.
• Invention to be protected against microbial change or destruction adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials that can be attacked or decomposed by microorganisms.
• parts of production plants for example cooling water circuits, are also mentioned which are impaired by the multiplication of microorganisms can be.
• technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids.
• Mixtures are preferably used to protect wood and wood-based materials against microorganisms, e.g. against wood-destroying or wood-discoloring organisms, especially fungi.
• Mixtures can be protected, for example, but not ' exclusively ' : timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wooden fences, wooden paneling, wooden windows and doors, plywood, chipboard, carpentry and wood products that are used in house building or joinery.
• a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure processes.
• Bacteria, fungi, yeasts, algae and slime organisms can be mentioned as materials.
• the active compounds according to the invention preferably act against fungi, in particular molds and wood-discoloring and wood-destroying fungi.
• microorganisms of the following genera may be mentioned:
• Aspergillus such as Aspergillus niger
• Chaetomium such as 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, such as 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 the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and ULV Cold and warm fog formulations.
• the formulations or agents for protecting industrial materials are prepared 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, ie emulsifiers and / or dispersants and / or foam-generating agents.
• extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
• water e.g. organic solvents can also be used as auxiliary solvents.
• the following are essentially suitable as liquid 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, for example petroleum fractions, alcohols such as butanol or glycerol 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, for example Aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
• Solid carriers come into question: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
• natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
• synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
• Possible solid carriers for granules are: eg broken and fractionated natural rocks such as calcite, marble, bimns, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut husks, corn cobs and tobacco stems .
• Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionogenic emulsifiers, such as
• Polyoxyethylene fatty acid esters polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates.
• Possible dispersants are: e.g. Lignin sulfite leaching 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.
• Mineral and vegetable oils can also be used as additives.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalcycanin 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 mixed with known fungicides, bactericides, acaricides, nematicides or insecticides can be used to broaden the spectrum of activity or 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.
• Triazoles such as:
• Azaconazole Azocyclotin, Bitertanol, Bromuconazole, Cyproconazole, Diclobutrazole, Difenoconazole, Diniconazole, Epoxyconazole, Etaconazole, Fenbuconazole,
• Fenchlorazole fenethanil, fluquinconazole, flusilazole, flutriafoi; Furconazole, Hexaconazole, Imibenconazle, Ipconazole, Isozofos, Myclobutanil, Metconazole, Paclobutrazol, Penconazole, Propioconazole, ( ⁇ ) -cis-l- (4-chlorophenyl) -2- (lH-l, 2,4-triazol-l-yl ) -cycloheptanol, 2- (l-tert-butyl) -l- (2-chlorophenyl) -3- (l, 2,4-triazol-l-yl) propan-2-ol, tebuconazole, tetraconazole, triadimphone , Triadimenol, triapenthenol,
• Imidazoles such as:
• Pyridines and pyrimidines such as: ancymidol, buthiobate, fenarimol, mepanipyrin, nuarimol, pyroxyfur, triamirol;
• Succinate dehydrogenase inhibitors such as:
• Sulfenamides such as: dichlofluanid, tolylfluanid, folpet, fluorfolpet; Captan, Captofol;
• Benzimidazoles such as:
• Morpholine derivatives such as:
• Benzthiazoles such as:
• Benzothiophene dioxides such as:
• Benzamides such as: 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide, tecloftalam;
• Boron compounds such as: boric acid, boric acid ester, borax;
• Formaldehyde and formaldehyde releasing compounds such as:
• Aldehydes such as:
• Cinnamaldehyde formaldehyde, glutardialdehyde, ß-bromocinnamaldehyde
• Benzalkonium chloride benzyldimethyltetradecylammonium chloride, benzyldimethyldodecylammonium chloride, dichlorobenzyldimethylalkylammonium chloride, dimethyldimethylammmonium chloride, dioctyldimethylammonium chloride, N-hexadecyltrimethylammonium chloride, 1-hexadidylchloride, 1-hexadidylchloride, ;
• Iodine derivatives such as:
• Phenols such as:
• Microbicides with activated halogen group such as: Bronidox, 2-bromo-2-nitro-l, 3-propanediol, 2-bromo-4'-hydroxy-acetophenone, 1-
• Pyridines such as: l-hydroxy-2-pyridinthione (and their Na, Fe, Mn, Zn salts), tetrachloro-4-methylsulfonylpyridine, pyrimethanol, mepanipyrim, dipyrithione, l-hydroxy-4-methyl-6 - (2,4,4-trimethylpentyl) -2 (1 H) pyridine;
• Trifluoxystrobin alpha- (methoxymethylene) -2- [[[[[[[[[[1 - [tri fluoromethyl) pheny 1] ethylidene] amino] - oxy] mefhyl] benzeneaceticacid methyl ester, 2 - [[[5-chloro-3- (trifluoromethyl) -2-pyridinyl] oxy] methyl] -alpha- (methoxyimino) -N-methylbenzeneacetamide,
• Metal salts such as:
• Oxides such as: tributyltin oxide, CU2O, CuO, ZnO;
• Insecticides / acaricides / nematicides Insecticides / acaricides / nematicides:
• Bacillus thuringiensis Barthrin, 4-Bromo-2 (4-chloro-phenyl) -l- (ethoxymethyl) -5- (trifluoromethyl) -lH-pyrrole-3-carbonitrile, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, Bioresmethrin, Bioallesmethrin, Bio bromophos A, bromophos M, Bufencarb, buprofezin, Butathiophos, Butocarboxim, Butoxycarboxim, cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, quinoline methionate, Chloethocarb, chlordane, chlorethoxyfos, chlorfenapyr, Chlorfen- vinphos, chlorfluazuron, chlormephos, N [(6-Chloro-3-pyr
• 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, Propoxuros Prothiophos, Prothoat, Pymetrozin, Pyrachlophos, Pyridaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
• Flurochloridone fluroxypyr, fomesafen, Fosamine, Fosametine, flamprop-isopropyl, flamprop-isopropyl-L, flumiclorac-pentyl, flumipropyn, Flumioxzim, hall atoms Flumioxzim, flupyrsulfuron-methyl, fluthiacet-methyl, glyphosate, Glufo- Sinate-ammonium, Haloxyfop, hexazinones, Imazamethabenz, Isoproturon, Isoxaben, Isoxapyrifop, Imazapyr, Imazaquin, Imazethapyr, Ioxynil, Isopropalin, Imazosulfuron, Imazomox, Isoxaflutole, Imazapic, Lactofen, Lenacil, Linuron,
• MCPA MCPA-thioethyl
• MCPB Mecoprop, Mecoprop-P, Mefenacet, Mefluidide, Metam, Metamitron, Metazachlor, Methabenzthiazuron, Methazole, Methoropytryne,
• Sethoxydim Sifuron, Simazine, Simetryn, Sulfosulfuron, Sulfometuron, Sulfentrazone, Sulcotrione, Sulfosate, Tar Oils, TCA, tebutam, Tebuthiuron, Terbacil, Terbumeton, Terbuthylazine,
• the active compounds can be used as such, in the form of concentrates or 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.
• the agents used to protect industrial materials generally contain active ingredients in an amount of 1 to 95%, preferably 10 to 75%.
• the application concentrations of the active compounds according to the invention 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.
• Mycelial pieces were cut out from colonies of Gloeophyllum trabeum (Pl), Coniophora souna (P2), Poria placenta (P3), Lentinus tigrinus (P4), Coriolus versicolor (P5) and Stemm sanguino- lentum (P6) and on an agama soil at 26 ° C incubated.
• the inhibition of hyphal growth on the nutrient-containing nutrient medium active substance concentration 6 ppm was compared to the growth in length without the addition of active substance and rated as a percentage inhibition.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Dentistry (AREA)
• Wood Science & Technology (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Agronomy & Crop Science (AREA)
• General Health & Medical Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Lubricants (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Chemical And Physical Treatments For Wood And The Like (AREA)
• Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Priority Applications (12)

Applications Claiming Priority (2)

Publications (2)

Family

ID=7685242

Family Applications (1)

Country Status (20)

Cited By (5)

Families Citing this family (16)

Citations (5)

Family Cites Families (9)

• 2001
  • 2001-05-18 DE DE10124208A patent/DE10124208A1/de not_active Withdrawn
• 2002
  • 2002-05-06 DE DE50207651T patent/DE50207651D1/de not_active Expired - Lifetime
  • 2002-05-06 PL PL363947A patent/PL208003B1/pl not_active IP Right Cessation
  • 2002-05-06 AT AT02724307T patent/ATE333793T1/de active
  • 2002-05-06 PT PT02724307T patent/PT1395117E/pt unknown
  • 2002-05-06 WO PCT/EP2002/004965 patent/WO2002094020A1/de not_active Ceased
  • 2002-05-06 RU RU2003136617/04A patent/RU2335128C2/ru not_active IP Right Cessation
  • 2002-05-06 AU AU2002255002A patent/AU2002255002B2/en not_active Ceased
  • 2002-05-06 EE EEP200300538A patent/EE05437B1/xx not_active IP Right Cessation
  • 2002-05-06 ES ES02724307T patent/ES2269677T5/es not_active Expired - Lifetime
  • 2002-05-06 JP JP2002590749A patent/JP4593881B2/ja not_active Expired - Fee Related
  • 2002-05-06 CA CA2447623A patent/CA2447623C/en not_active Expired - Fee Related
  • 2002-05-06 DK DK02724307.0T patent/DK1395117T4/da active
  • 2002-05-06 EP EP02724307A patent/EP1395117B2/de not_active Expired - Lifetime
  • 2002-05-06 NZ NZ529567A patent/NZ529567A/en not_active IP Right Cessation
  • 2002-05-06 BR BRPI0209830-0A patent/BR0209830B1/pt not_active IP Right Cessation
  • 2002-05-06 CZ CZ20033129A patent/CZ20033129A3/cs unknown
  • 2002-05-06 CN CNB028101391A patent/CN100342786C/zh not_active Expired - Fee Related
  • 2002-05-16 US US10/147,224 patent/US7888371B2/en not_active Expired - Fee Related
• 2003
  • 2003-11-11 NO NO20035012A patent/NO330409B1/no not_active IP Right Cessation
  • 2003-11-14 ZA ZA200308893A patent/ZA200308893B/xx unknown
• 2010
  • 2010-12-31 US US12/982,927 patent/US8143275B2/en not_active Expired - Fee Related

Patent Citations (5)

Also Published As

Similar Documents

Legal Events