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EP1641798A1 - Triazolopyrimidines - Google Patents

Triazolopyrimidines

Info

Publication number
EP1641798A1
EP1641798A1 EP04735570A EP04735570A EP1641798A1 EP 1641798 A1 EP1641798 A1 EP 1641798A1 EP 04735570 A EP04735570 A EP 04735570A EP 04735570 A EP04735570 A EP 04735570A EP 1641798 A1 EP1641798 A1 EP 1641798A1
Authority
EP
European Patent Office
Prior art keywords
formula
carbon atoms
halogen
alkyl
optionally substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP04735570A
Other languages
German (de)
English (en)
Inventor
Olaf Gebauer
Ulrich Heinemann
Hans-Ludwig Elbe
Herbert Gayer
Stefan Herrmann
Jörg Nico GREUL
Bernd-Wieland Krüger
Stefan Hillebrand
Ronald Ebbert
Ulrike Wachendorff-Neumann
Peter Dahmen
Karl-Heinz Kuck
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1641798A1 publication Critical patent/EP1641798A1/fr
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/55—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/61—Halogen atoms or nitro radicals
    • 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

Definitions

  • the present invention relates to new triazolopyrimidines, a process for their preparation and their use for controlling unwanted microorganisms.
  • the invention also relates to new intermediates and processes for their production.
  • R.1 stands for optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted cycloalkyl or for optionally substituted heterocyclyl,
  • R2 represents hydrogen or alkyl
  • Rl and R ⁇ together with the nitrogen atom to which they are attached represent an optionally substituted heterocyclic ring
  • R ⁇ represents optionally substituted pyridyl or optionally substituted pyridyl
  • R ⁇ and X have the meanings given above and
  • ⁇ l represents halogen
  • triazolopyrimidines of the formula (I) are very suitable for controlling unwanted microorganisms. Above all, they show a strong fungicidal activity and can be used both in crop protection and in material protection.
  • the triazolopyrimidines of the formula (I) according to the invention have a substantially better microbicidal activity than the constitutionally most similar, previously known substances with the same direction of action.
  • the compounds of the formula (T) according to the invention can, if appropriate, as mixtures of various possible isomeric forms, in particular of stereoisomers, such as E and Z, threo and erythro and optical isomers, such as R and S isomers or atropisomers, but if appropriate also of tautomers. Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, even if only the compounds of the formula (I) are mentioned here in general.
  • the compounds of the formula (I) have acidic or basic properties and can form salts. If the compounds of the formula (I) carry hydroxyl, carboxy or other groups which induce acidic properties, these compounds can be reacted with bases to form salts.
  • bases are, for example, hydroxides, carbonates, bicarbonates of the alkali and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines with (-C4) -alkyl radicals and mono-, di- and Trialkanolamines of (C ⁇ -C4) alkanols.
  • acids are, for example, mineral acids, such as salt, sulfuric and phosphoric acid, organic acids, such as acetic acid or oxalic acid, and acid salts, such as NaHSO4 and KHSO4.
  • the salts obtainable in this way also have fungicidal and microbicidal properties.
  • the invention also relates to the salt-like derivatives formed from compounds of the formula (I) by reaction with basic or acidic compounds, and to the N-oxides which can be prepared by customary oxygenation methods.
  • the triazolopyrimidines according to the invention are generally defined by the formula (I).
  • Preferred substances of the formula (I) are those in which
  • Rl stands for alkyl with 1 to 6 carbon atoms, which can be substituted one to five times, in the same way or differently, by halogen, cyano, hydroxy, alkoxy with 1 to 4 carbon atoms and / or cycloalkyl with 3 to 6 carbon atoms, or
  • Rl stands for alkenyl having 2 to 6 carbon atoms, which can be monosubstituted to trisubstituted, identical or different, by halogen, cyano, hydroxy, alkoxy having 1 to 4 carbon atoms and / or cycloalkyl having 3 to 6 carbon atoms, or
  • R! represents alkynyl having 3 to 6 carbon atoms, which can be monosubstituted to triple, identical or differently substituted by halogen, cyano, alkoxy having 1 to 4 carbon atoms and / or cycloalkyl having 3 to 6 carbon atoms, or
  • Rl stands for cycloalkyl with 3 to 6 carbon atoms, which can be monosubstituted to trisubstituted, identical or different, by halogen and / or alkyl having 1 to 4 carbon atoms, or Rl represents saturated or unsaturated heterocyclyl with 5 or 6 ring members and 1 to 3 heteroatoms, such as nitrogen, oxygen and / or sulfur, it being possible for the heterocyclyl to be mono- or disubstituted by halogen, alkyl having 1 to 4 carbon atoms, cyano and / or cycloalkyl with 3 to 6 carbon atoms,
  • R 2 represents hydrogen or alkyl having 1 to 4 carbon atoms
  • Rl and R 2 together with the nitrogen atom to which they are attached represent a saturated or unsaturated heterocyclic ring with 3 to 6 ring members, where the heterocycle may contain a further nitrogen, oxygen or sulfur atom as an Rmg member and wherein the heterocycle bis can be substituted three times by fluorine, chlorine, bromine, alkyl having 1 to 4 carbon atoms and / or haloalkyl having 1 to 4 carbon atoms and 1 to 9 fluorine and / or chlorine atoms.
  • R ⁇ stands for pyridyl, which can be substituted by up to four, the same or different
  • Haloalkyl or haloalkoxy each having 1 to 3 carbon atoms and 1 to 7 halogen atoms
  • R ⁇ • stands for pyrimidyl, which can be monosubstituted to triple, identical or differently substituted by
  • Haloalkyl or haloalkoxy each having 1 to 3 carbon atoms and 1 to 7 halogen atoms
  • Rl represents allyl, dichlorallyl, propargyl, cyclopropyl, cyclopentyl, cyclohexyl, piperidinyl or morpholinyl,
  • R 2 represents hydrogen, methyl or ethyl, or
  • Rl and R 2 together with the nitrogen atom to which they are attached represent pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, 3,6-dihydro-l (2H) -piperidinyl or tetrahydro-l (2H) -pyridazinyl, where these radicals can be substituted by 1 to 3 fluorine atoms, 1 to 3 methyl groups and / or trifluoromethyl;
  • R ⁇ stands for pyridyl which is linked in the 2- or 4-position and can be mono- to tetrasubstituted, identical or differently substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximino methyl, methoximinoethyl and / or trifluoromethyl, or
  • R ⁇ stands for pyrimidyl which is linked in the 4-position and can be mono- to trisubstituted, identical or differently substituted by fluorine, chlorine, bromine, cyano, methyl, ethyl, methoxy, methylthio, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximinoethyl and / or trifluoromethyl,
  • X represents fluorine or chlorine.
  • Formula (H) provides a general definition of the dihalotriazolo-pyrimidines required as starting materials when carrying out process (a) according to the invention.
  • R 1 and X preferably have those meanings which have already been mentioned as preferred for these radicals in connection with the description of the substances of the formula (I) according to the invention.
  • ⁇ l preferably represents fluorine, chlorine or bromine, particularly preferably fluorine or chlorine.
  • the dihalotriazolopyrimidines of the formula (H) are new. These substances are also suitable for controlling unwanted microorganisms.
  • the dihalotriazolopyrimidines can be prepared by:
  • R ⁇ has the meaning given above
  • halogenating agents optionally in the presence of a diluent.
  • Formula (IV) provides a general definition of the dihydroxytriazolopyrimidines required as starting materials when carrying out process (b).
  • R ⁇ preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • the dihydroxy-triazolopyrimidines of the formula (IV) are also not yet known. They can be made by
  • R ⁇ has the meaning given above and
  • R ⁇ represents alkyl having 1 to 4 carbon atoms
  • Formula (V) provides a general definition of the heteroarylmalonic esters required as starting materials for carrying out process (c) according to the invention.
  • R ⁇ preferably has those meanings which have already been mentioned as preferred for this radical in connection with the description of the substances of the formula (I) according to the invention.
  • Rr stands for methyl or ethyl.
  • heteroarylmalonic esters of the formula (V) are known (cf. DE 38 20 538-A and WO 01-11 965).
  • R4 has the meaning given above and
  • ⁇ represents halogen or haloalkyl.
  • R6 represents halogen or haloalkyl
  • R ⁇ and R8 are independently hydrogen, fluorine, chlorine, bromine, methyl, ethyl or methoxy.
  • the pyridylmalonic esters of the formula (V-a) can be prepared by
  • Y 2 represents halogen
  • R ⁇ has the meaning given above
  • Formula (VU) provides a general definition of the halopyridines required as starting materials for carrying out process (d) according to the invention.
  • R- > preferably represents fluorine, chlorine or trifluoromethyl.
  • Y 2 preferably represents chlorine or bromine.
  • halopyridines of the formula (VII) are known synthetic chemicals.
  • the malonic esters of the formula (VIH) which are furthermore required as starting materials for carrying out the process (d) according to the invention are likewise known synthetic chemicals.
  • the pyrimidylmalonic esters of the formula (V-b) can be prepared by
  • R ⁇ , R? and R ⁇ have the meanings given above and
  • R4 has the meaning given above
  • the halopyrimidines required as starting materials for carrying out process (e) according to the invention are generally defined by the formula (Dt).
  • R preferably represents fluorine, chlorine or trifluoromethyl.
  • R ⁇ and R ° are also preferably independently of one another hydrogen, fluorine, chlorine, bromine, methyl, ethyl or methoxy.
  • Y ⁇ preferably represents chlorine or bromine.
  • the halopyrimidines of the formula (IX) are known and can be prepared by known methods (cf. J. Chem. Soc. 1955. 3478, 3481).
  • aminotriazole of the formula (VI) which is also required as a starting material for carrying out process (c) according to the invention is a commercially available chemical.
  • Suitable halogenating agents for carrying out process (b) are all components customary for the replacement of hydroxyl groups by halogen.
  • Phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphorus oxychloride, thionyl chloride, thionyl bromide or mixtures thereof are preferably usable.
  • the corresponding fluorine compounds of the formula (IT) can be prepared from the chlorine or bromine compounds by reaction with potassium fluoride.
  • Formula (E1) generally defines the amines which are further required as starting materials for carrying out process (a) according to the invention.
  • R ⁇ and R 2 preferably have those meanings which have already been given as preferred for R and R 2 in connection with the description of the compounds of the formula (I) according to the invention.
  • the amines of the formula (III) are known or can be prepared by known methods.
  • Suitable diluents for carrying out process (a) according to the invention are all customary inerts. organic solvents.
  • Halogenated hydrocarbons such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane, can preferably be used;
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, 1,2- Diethoxyethane or anisole;
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile;
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide
  • Suitable acid acceptors for carrying out process (a) according to the invention are all inorganic or organic bases customary for such reactions.
  • Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates such as, for example, sodium hydride, sodium amide, lithium diisopropylamide, sodium methylate, sodium ethylate, potassium tert-butoxide, are preferably usable , Sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate and sodium hydrogen carbonate, and also ammonium compounds such as ammonium hydroxide, ammonium acetate and ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-N-dimethylanil N-dimethyl-benzylamine, pyridine, N-methylpipe
  • Suitable catalysts for carrying out process (a) according to the invention are all reaction accelerators customary for such reactions. Fluorides such as sodium fluoride, potassium fluoride or ammonium fluoride can preferably be used.
  • reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 0 ° C and 80 ° C.
  • Suitable diluents for carrying out process (b) according to the invention are all solvents customary for such halogenations.
  • Halogenated aliphatic or aromatic hydrocarbons such as chlorobenzene, can preferably be used.
  • the halogenating agent itself for example phosphorus oxychloride or a mixture of halogenating agents, can also act as the diluent.
  • the temperatures can also be varied within a wide range when carrying out process (b). In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.
  • dihydroxy-triazole pyrimidine of the formula (IV) is generally reacted with an excess of halogenating agent.
  • the processing takes place according to usual methods.
  • Suitable diluents for carrying out process (c) are all inert organic solvents which are customary for such reactions.
  • Alcohols such as methanol, ethanol, n-propanol, i-propanol, n-butanol and tert-butanol can preferably be used.
  • Suitable acid binders for carrying out process (c) are all inorganic and organic bases customary for such reactions.
  • Tertiary amines such as tributylamine or pyridine can preferably be used. Amine used in excess can also act as a diluent.
  • the temperatures can be varied within a substantial range when carrying out process (c). In general, temperatures between 20 ° C and 200 ° C, preferably between 50 ° C and 180 ° C.
  • heteroarylmalonic esters of the formula (V) and aminotriazole of the formula (VI) are generally reacted in equivalent amounts. However, it is also possible to use one or the other component in an excess. The processing takes place according to usual methods.
  • Suitable diluents for carrying out processes (d) and (e) according to the invention are all customary, inert organic solvents.
  • Halogenated hydrocarbons such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane, can preferably be used;
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;
  • Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile;
  • Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylform
  • Suitable acid acceptors for carrying out processes (d) and (e) according to the invention are in each case all of the customary inorganic or organic bases.
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • reaction temperatures can also be varied within a substantial range when carrying out processes (d) and (e) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 0 ° C and 80 ° C.
  • the processes according to the invention are generally carried out under atmospheric pressure. However, it is also possible to work under increased pressure.
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as, for example, Pseudpmonas syringae pv. Lachrymans;
  • Erwinia species such as, for example, Erwinia amylovora;
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe Arte ⁇ such as Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Urorrryces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tületia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea; ,
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Alternaria species such as, for example, Alternaria brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
  • the active compounds according to the invention also have a very good strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defense forces against attack by unwanted microorganisms.
  • Plant-strengthening (resistance-inducing) substances are to be understood in the present context as substances which are able to stimulate the defense system of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesired microorganisms.
  • Undesirable micro-organisms in the present case are to be understood as phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can thus be used to protect plants against attack by the pests mentioned within a certain period of time after the treatment.
  • the period of time within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days, after the plants have been treated with the active compounds.
  • the fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
  • the active compounds according to the invention can be used with particularly good success for combating cereal diseases, for example against Erysiphe species, for diseases in wine, fruit and vegetable cultivation, for example against Botrytis, Venturia, Sphaerotheca and Podosphaera species ,
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of the plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and in the case of propagation material, in particular seeds single or multi-layer wrapping.
  • the invention 'for protecting industrial materials against attack and destruction can be used by undesirable microorganisms.
  • technical materials are understood to mean non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms .
  • parts of production systems for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms.
  • 'industrial materials are preferably glues, sizes, papers and cardboards, leather, wood, paints, cooling and scnmierstoff called heat transfer fluids particularly preferably wood.
  • 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 according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • 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 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, 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, 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, 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.
  • organic solvents can, for example, 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, for example petroleum fractions
  • alcohols such as butanol or glycol as well as their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dirthethyl 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 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.
  • Solid carriers for granules are possible: e.g.
  • Suitable emulsifiers and or foaming agents are: for example nonionic 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 dispersants are: eg 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 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 to broaden the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Dagger G debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; Diclomezine; dicloran; diethofencarb; Difenoconazole; diflumetorim; dimethirimol; dimethomorph; dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolon; edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole;
  • famoxadone fenamidone; Fenapanil; fenarimol; Fenbuconazole; fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover; flumorph; fluoromides; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil; Furmecyclox;
  • mancozeb maneb; Meferimzone; mepanipyrim; mepronil; metalaxyl; Metalaxyl-M; Metconazole; methasulfocarb; Methfuroxam; metiram; metominostrobin; Metsulfovax; mildiomycin; myclobutanil; myclozoline;
  • natamycin natamycin
  • nicobifen Nitro Thal-isopropyl
  • Noviflumuron nuarimol
  • tebuconazole tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; Triazbutil; triazoxide; Tricyclamide; Tricyclazole; tridemorph; trifloxystrobin; triflumizole; triforine; triticonazole;
  • copper salts and preparations such as Bordeaux mixture; copper; Copper naphthenate; copper oxychloride; Copper sulfate; Cufraneb; copper; mancopper; Oxine-copper.
  • DDT Deltamethrin, Demeton-S-methyl, Demeton-S-methylsulphone, Diafenthiuron, Dialifos, Diazinone, Dichlofenthion, Dichlorvos, Dicofol, Dicrotophos, Dicyclanil, Diflubenzuron, Dimethoate, Dimethylvinphoc, Diap, Dinobutoni, Dinobutono, Dinobutoni Docusat-sodium, Dofenapyn, DOWCO-439,
  • Halofenozide HCH, HCN-801, Heptenophos, Hexaflumuron, Hexythiazox, Hydra-methylnone, Hydroprene, IKA-2002, hnidacloprid, imiprothrin, indoxacarb, iodofenphos, iprobefos, isazofos, isofenphos, isoprocarb, isoxathion, ivermectin,
  • Mecarbam Mesulfenfos, Metaldehyde, Metam-sodium, Methacrifos, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoprene, Methoxychlor, Methoxyfenozide, Metolcarb, Metoxadiazone, MilevinephinI, Mevincinin MKB, Mevincinin MK5 MON-45700, Monocrotophos, Moxidectin, MTI-800,
  • NC-104 NC-170, NC-184, NC-194, NC-196, Niclosamide, Nicotine, Nitenpyram, Nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768, Novaluron, Noviflumuron,
  • Paecilomyces fumosoroseus Parathion-methyl, Parathion (-ethyl), Permethrin (eis, trans-), Petroleum, PH-6045, Phenothrin (lR-trans isomer), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Piperonyl butoxide, Pirimicarb, Pirimiphos-methyl, Piri i-phos-ethyl, Prallethrin, Profenofos, Promecarb, Propaphos, Propargite, Propetamphos, Propoxur, Prothiofos, Prothoate, Protrifenbute, Pymetrozine, Pyraclofos, Pyrethridylrine, Pyreshridylrine Pyridathione, pyrimidifene, pyriproxyfen,
  • the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad antimycotic activity spectrum in particular against dermatophytes and yeasts, molds and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata), and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, microsporon species such as microsporon canis and a ⁇ douinii.
  • the list of these mushrooms is in no way a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.
  • the compounds of the formula (I) according to the invention are furthermore suitable for suppressing the growth of tumor cells in humans and mammals. This is based on an interaction of the compounds according to the invention with tubulin and microtubules and by promoting microtubule polymerization.
  • an effective amount of one or more compounds of formula (I) or pharmaceutically acceptable salts thereof can be administered.
  • the active compounds can be soluble as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes Powders, dusts and granules can be used. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to prepare the active ingredient or the active ingredient itself Inject soil. The seeds of the plants can also be treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the " application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • all plants and their parts can be treated.
  • wild plant species and plant varieties and their parts obtained by conventional biological breeding methods such as crossing or protoplast fusion, are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “parts of plants” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been cultivated by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, breeds, bio- and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic”) effects.
  • superadditive for example, reduced application rates and / or widening of the activity spectrum and / or one Strengthening the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the crop products possible, which go beyond the expected effects.
  • the preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the crop products, higher storability and / or workability of the harvested products.
  • transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton, tobacco and rapeseed are highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects, arachnids, namatodes and snails by toxins arising in the plants, especially those which are caused by the genetic material from Bacillus thuringiensis (e.g. by the genes Cry ⁇ A (a ), CryIA (b), Cry ⁇ A (c), CryHA, CrylUA, CryIIJB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter referred to as "Bt plants”).
  • Bacillus thuringiensis e.g. by the genes Cry ⁇ A (a ), CryIA (b), Cry ⁇ A (c), CryHA, CrylUA, CryIIJB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations
  • traits As properties (“traits”) the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized.
  • SAR systemic acquired resistance
  • the traits are furthermore particularly emphasized by the plants' increased tolerance to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example "PAT” gene).
  • the genes which impart the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Bt plants are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YTELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucoton® (cotton) and NewLeaf® (potato).
  • YTELD GARD® e.g. corn, cotton, soy
  • KnockOut® e.g. corn
  • StarLink® e.g. corn
  • Bollgard® Cotton
  • Nucoton® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties which are marketed under the trade names Roundup Ready® (tolerance against glyphosate, for example corn, cotton, soybeans), Liberty Link® (tolerance against phos- phinotricin, for example rapeseed), IMI® (tolerance to lrnidazolinones) and STS® (tolerance to sulfonylureas, for example maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the tributylamine is decanted off and the 6- (3-trifluoromethyl-pyridin-2-yl) - [1,2,4] triazolo [1,5-a] pyrimidine-5,7-diol obtained (yield: about 8 g, 60% purity) is used in the next reaction step without further purification.
  • the tributylamine is decanted off and the 6- (5-chloro-4-pyrimidmyl) [1,2,4] triazolo [1,5-a] pyrimidine-5,7-diol obtained (yield: about 15 g, 11% purity) , about 15% of theory) is used in the next reaction step without further purification.
  • Emulsifier 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in the greenhouse at approximately 21.degree. C. and a relative atmospheric humidity of approximately 90%.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Botrytis test (bean) / protective
  • Emulsifier 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Emulsifier 0.6 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Example 2 shows an efficiency of over 90% at an application rate of 500 g / ha.

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  • Organic Chemistry (AREA)
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Abstract

L'invention concerne de nouvelles triazolopyrimidines de la formule (I) dans laquelle R<1>, R<2>, R<3> et X ont la signification donnée dans le descriptif, un procédé de fabrication de ces composés et leur utilisation dans la lutte contre des micro-organismes nuisibles. L'invention concerne également de nouveaux intermédiaires des formules (II), (IV), (V-a), et (V-b), et des procédés de fabrication de ces composés.
EP04735570A 2003-06-04 2004-06-01 Triazolopyrimidines Ceased EP1641798A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10325133A DE10325133A1 (de) 2003-06-04 2003-06-04 Triazolopyrimidine
PCT/EP2004/005876 WO2004108727A1 (fr) 2003-06-04 2004-06-01 Triazolopyrimidines

Publications (1)

Publication Number Publication Date
EP1641798A1 true EP1641798A1 (fr) 2006-04-05

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EP04735570A Ceased EP1641798A1 (fr) 2003-06-04 2004-06-01 Triazolopyrimidines

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US (1) US20070275985A1 (fr)
EP (1) EP1641798A1 (fr)
JP (1) JP2006526587A (fr)
KR (1) KR20060015304A (fr)
CN (1) CN1802379A (fr)
BR (1) BRPI0410906A (fr)
CO (1) CO5721005A2 (fr)
CR (1) CR8074A (fr)
DE (1) DE10325133A1 (fr)
EC (1) ECSP056201A (fr)
IL (1) IL172098A0 (fr)
MX (1) MXPA05012951A (fr)
WO (1) WO2004108727A1 (fr)
ZA (1) ZA200509637B (fr)

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BRPI0517432A (pt) * 2004-12-17 2008-10-07 Basf Ag composto, uso dos mesmos, agente para combater fungos fitopatogênicos, processo para combater fungos fitopatogênicos, e, semente
US20080132412A1 (en) * 2004-12-17 2008-06-05 Basf Aktiengesellschaft 7-Amino-6-Heteroaryl-1,2,4-Triazolo[1,5-A]Pyrimidines and Their Use for Controlling Harmful Fungi
WO2006092428A2 (fr) * 2005-03-02 2006-09-08 Basf Aktiengesellschaft 7-amino-azolopyrimidine 2-substituee, son procede de fabrication et son utilisation pour lutter contre les champignons nuisibles, et agents renfermant ce compose
WO2006122740A2 (fr) * 2005-05-17 2006-11-23 Basf Aktiengesellschaft 7-amino-6-hetarylimidazolo[1,2-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles
WO2007006723A1 (fr) * 2005-07-13 2007-01-18 Basf Aktiengesellschaft Composes de 7-amino-6-tetrazolyl-1,2,4-triazolo[1,5-a]pyrimidine et utilisation de ceux-ci pour lutter contre des champignons nuisibles
WO2007101870A1 (fr) * 2006-03-08 2007-09-13 Basf Se Triazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
CN101153041B (zh) * 2006-09-28 2010-05-12 中国科学院化学研究所 1,2,3-三唑并1,3-二氮杂环化合物及其制备方法与应用
WO2008092836A2 (fr) * 2007-01-30 2008-08-07 Basf Se Procédé d'amélioration de la santé des plantes
EP1952691A3 (fr) * 2007-01-31 2008-09-17 Basf Se Procédé d'amélioration de la santé végétale par application d'un dérivé de triazolopyrimidine
US9101131B2 (en) 2007-12-03 2015-08-11 Valent U.S.A., Corporation Seed treatment formulations
EP2229052B1 (fr) * 2007-12-03 2016-08-24 Valent U.s.a., Corporation Formulations de traitement des semences et procédés d'utilisation
EP2204366A1 (fr) 2008-12-19 2010-07-07 Bayer CropScience AG Pyridazinones substitués par phényle agissant en tant qu'herbicide et insecticide
WO2011035878A1 (fr) 2009-09-25 2011-03-31 Bayer Cropscience Ag Pyridazinones à activité herbicide substitués par un phényle
WO2011045271A1 (fr) 2009-10-15 2011-04-21 Bayer Cropscience Ag Pyridazinones à substitution hétérocyclyle, à effet herbicide
RU2013114184A (ru) 2010-09-01 2014-10-10 Байер Интеллектуэль Проперти Гмбх Гербицидно-активные кетосультамы и дикетопиридины
CN106810550A (zh) * 2017-01-10 2017-06-09 湖南华腾制药有限公司 一种萘啶衍生物的制备方法

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DE10325133A1 (de) 2004-12-23
US20070275985A1 (en) 2007-11-29
ECSP056201A (es) 2006-04-19
JP2006526587A (ja) 2006-11-24
MXPA05012951A (es) 2006-02-13
CO5721005A2 (es) 2007-01-31
BRPI0410906A (pt) 2006-06-27
ZA200509637B (en) 2007-02-28
CR8074A (es) 2007-09-11
KR20060015304A (ko) 2006-02-16
CN1802379A (zh) 2006-07-12
WO2004108727A1 (fr) 2004-12-16
IL172098A0 (en) 2009-02-11

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