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WO2006066874A1 - Nouveaux derives de triazolopyrimidine - Google Patents

Nouveaux derives de triazolopyrimidine Download PDF

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Publication number
WO2006066874A1
WO2006066874A1 PCT/EP2005/013710 EP2005013710W WO2006066874A1 WO 2006066874 A1 WO2006066874 A1 WO 2006066874A1 EP 2005013710 W EP2005013710 W EP 2005013710W WO 2006066874 A1 WO2006066874 A1 WO 2006066874A1
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formula
crc
hydrogen
alkyl
compound
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PCT/EP2005/013710
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English (en)
Inventor
Sebastian Volker Wendeborn
Clemens Lamberth
Kurt Nebel
Patrick Jelf Crowley
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Syngenta Participations Ag
Syngenta Limited
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Publication of WO2006066874A1 publication Critical patent/WO2006066874A1/fr

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    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0898—Compounds with a Si-S linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1896—Compounds having one or more Si-O-acyl linkages

Definitions

  • the present invention relates to novel triazolopyrimidine derivatives as active ingredients which have microbiocidal activity, in particular fungicidal activity.
  • the invention also relates to preparation of these active ingredients, to novel heterocyclic derivatives used as intermediates in the preparation of these active ingredients, to preparation of these novel intermediates, to agrochemical compositions which comprise at least one of the novel active ingredients, to preparation of these compositions and to use of the active ingredients or compositions in agriculture or horticulture for controlling or preventing infestation of plants or non-living materials by phytopathogenic microorganisms , preferably fungi.
  • the present invention provides a compound of formula (I):
  • R 2 and R 3 each independently of each other and independently of n when n is 2, 3 or
  • R 2 and R 3 together with the carbon atom to which they are attached, form an optionally substituted, three- to six-membered ring;
  • R 4 and R 5 are C r C 6 alkyl, CrC 6 haloalkyl, C 3 -
  • R 6 is hydrogen, CrCealkyl, CrC 6 haloalkyl or C 3 -C 6 cycloalkyl;
  • R 7 is an optionally substituted aryl or heteroaryl;
  • R 8 is CrC 6 alkyl, halogen or cyano
  • R 9 is hydrogen, mercapto or CrCealkylthio
  • X is oxygen or sulfur; and n is 1 , 2, 3 or 4.
  • n is 2, 3 or 4, which means that 2, 3 or 4 contiguous carbon atoms respectively are present between the nitrogen atom substituted by R 1 and the silicon atom
  • the R 2 and R 3 substituents on those carbon atoms can be the same or different substituents each independently of each other.
  • the first carbon atom can be substituted by R 2 as ethyl and R 3 as bromine
  • the second carbon atom can be substituted R 2 as methyl and R 3 as methyloxy.
  • aryl includes aromatic hydrocarbon rings like phenyl, naphthyl, anthracenyl, phenanthrenyl and biphenyl, with phenyl being preferred.
  • Heteroaryl stands for aromatic ring systems comprising mono-, bi- or tricyclic systems wherein at least one oxygen, nitrogen or sulfur atom is present as a ring member.
  • Examples are furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridiyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, indazolyl, benzotriazolyt, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxal
  • aryl and heteroaryl groups may be optionally substituted. This means that they may carry one or more identical or different substituents. Normally not more than three substituents are present at the same time.
  • substituents of aryl or heteroaryl groups are: halogen, alkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, alkenyl, haloalkenyl, cycloalkenyl, alkynyl, haloalkynyl, alkyloxy, haloalkyloxy, cycloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkenyloxy, alkylthio, haloalkylthio, cycloalkylthio, alkenylthio, alkynylthio, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkenylcarbony
  • Typical examples include phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethylphenyl, 2- methylphenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6- difluorophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6- dichlorophenyl, 2-chloro-3-fluorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5- fluorophenyl, 2-chloro-6-fluorophenyl, 3-chloro-2-fluorophenyl, 4-chloro-2- fluorophenyl, 5-chloro-2-fluorophenyl, 2-fluoro-3-trifluoromethylphenyl, 2-fluoro-4- trifiuoromethylphenyl
  • R 2 and R 3 can form an optionally substituted three- to six-membered attached ring together with the carbon atom to which they are attached.
  • Typical examples of three- to six-membered attached ring include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, oxiranyl, aziridinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, 1 ,3-dioxolanyl, 1 ,3-dioxanyl and 1 ,4- dioxanyl.
  • R 2 and R 3 form an optionally substituted three- to six-membered attached ring together with the carbon atom to which they are attached; the ring is linked to the same carbon atom when n is 1 , or can be linked to the same carbon atom or to another carbon atom when n is 2, 3 or 4.
  • the above-defined three- to six-membered attached rings may be optionally substituted: they may carry one or more identical or different substituents. Normally not more than three substituents are present at the same time.
  • substituents of said attached ring include hydrogen, halogen, Ci-C 6 alkyl, Cr C 6 haloalkyl, Ci-C ⁇ cycloalkyl and cyano.
  • halogen is fluorine, chlorine, bromine or iodine.
  • alkyl, alkenyl or alkynyl radicals may be straight-chained or branched.
  • Alkyl on its own or as part of another substituent is, depending upon the number of carbon atoms mentioned, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl and the isomers thereof, for example, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl or tert-pentyl.
  • a haloalkyl group may contain one or more identical or different halogen atoms and for example may stand for CH 2 CI, CHCI 2 , CCI 3 , CH 2 F, CHF 2 , CF 3 , CF 3 CH 2 , CH 3 CF 2 , CF 3 CF 2 , CCI 3 CCI 2 , etc.
  • Cycloalkyl on its own or as part of another substituent is, depending upon the number of carbon atoms mentioned, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Alkenyl on its own or as part of another substituent is, depending upon the number of carbon atoms mentioned, for example, ethenyl, allyl, 1-propenyl, buten-2- yl, buten-3-yl, penten-1-yl, penten-3-yl, hexen-1-yl or 4-methyl-3-pentenyl.
  • Alkynyl on its own or as part of another substituent is, depending upon the number of carbon atoms mentioned, for example, ethynyl, propyn-1-yl, propyn-2-yl, butyn-1-yl, butyn-2-yl, 1-methyl-2-butynyl, hexyn-1-yl or 1-ethyl-2-butynyl.
  • the presence of one or more possible asymmetric carbon atoms in the compounds of formula I means that the compounds may occur in optically isomeric, that means enantiomeric or diastereomeric forms.
  • optically isomeric that means enantiomeric or diastereomeric forms.
  • geometric isomerism that means cis-trans or [E)-[Z) isomerism may also occur.
  • atropisomers may occur as a result of restricted rotation about a single bond.
  • Formula I is intended to include all those possible isomeric forms and mixtures thereof.
  • the compounds of formula I according to the invention are in free form or in an agronomically usable salt form.
  • R 1 is hydrogen, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl
  • R 2 and R 3 are hydrogen, halogen, C r C 6 alkyl or C r C 3 haloalkyl;
  • R 4 and R 5 are Ci-C 6 alkyl, C r C 6 haloalkyl or C 3 -
  • R 6 is hydrogen, CrC 6 alkyl or Ci-C 6 haloalkyl
  • R 7 is an optionally substituted aryl
  • R 8 is C r C 3 alkyl or halogen
  • R 9 is hydrogen, mercapto or methylthio
  • X is oxygen or sulfur; and n is 1 , 2 or 3.
  • R 1 is hydrogen or C 2 -C 4 alkynyl
  • R 2 and R 3 each independently of each other and independently of n when n is 2, 3 or
  • R 4 and R 5 are CrC 3 alkyl or C r C 3 haloalkyl;
  • R 6 is CrCjjalkyl or C r C 3 haloalkyl;
  • R 7 is phenyl substituted at least in one ⁇ rf/?f>-position with halogen
  • R 8 is chloro or fluoro
  • R 9 is hydrogen or mercapto
  • X is oxygen; and n is 1 or 2.
  • R 2 and R 3 are hydrogen, methyl or trifluoromethyl
  • R 4 and R 5 are methyl or ethyl
  • R 6 is methyl or ethyl
  • R 7 is 2,4,6-trifluorophenyl or 2-chloro-6-fluorophenyl; R 8 is chloro; R 9 is hydrogen; X is oxygen; and n is i.
  • Preferred individual compounds are:
  • the compounds of formula I can be obtained by coupling of a compound of formula II, wherein R 7 , R 8 and R 9 are as defined for formula I and Hal is halogen, preferably fluorine, chlorine or bromine, with a compound of formula III, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X and n are as defined for formula I.
  • the reaction (Il + III -> I) can be carried out in a manner known per se for the transformation of amines with heterocyclic halides, e.g. 4-halopyrimidines or 7- halotriazolo[1 ,5-a]pyrimidines.
  • the reaction is carried out in solution.
  • organic solvents like N,N-dimethylformamide, N 1 N- dimethylacetamide, acetonitrile, dioxane, N-methylpyrrolidon, methanol, ethanol or dimethylsulfoxide, or organic solvents, like toluene or xylene in mixture with water and a phase transfer catalyst.
  • the reaction is advantageously carried out in the presence of a base.
  • organic or inorganic bases may be used, for instance triethylamine, diisopropylethylamine, pyridine, 4-dimethylaminopyridine, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, sodium carbonate or potassium carbonate.
  • Reaction temperatures are between 0 0 C and +100 0 C, preferably between +10 0 C and +50 0 C.
  • the reaction of trialkylsilyl- containing amines with compounds of formula Il is already described in WO 98/46607, US 6117876 and US 6297251.
  • C-(oxysilanyl)methylamines of formula (Ilia) can be achieved from chloro-chloromethylsilanes of formula (V), following a route described in J. Organomet. Chem. 1980, 190, 247 - 256, WO 2003/068845 and WO 2004/067605.
  • novel compounds of formula I have, for practical purposes, a very advantageous spectrum of activities for protecting plants against diseases that are caused by fungi as well as by bacteria and viruses.
  • the compounds of formula I can be used in the agricultural sector and related fields of use as active ingredients for controlling plant pests or on non-living materials for control of spoilage microorganisms or organisms potentially harmfull to man.
  • the novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and are used for protecting numerous cultivated plants.
  • the compounds of formula I can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protec- ting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.
  • compositions comprising a compound of formula I before planting: seed, for example, can be dressed before being sown.
  • the active ingredients according to the invention can also be applied to grains (coating), either by impregnating the seeds in a liquid formulation or by coating them with a solid formulation.
  • the composition can also be applied to the planting site when the propagation material is being planted, for example, to the seed furrow during sowing. The invention relates also to such methods of treating plant propagation material and to the plant propagation material so treated.
  • the compounds according to present invention can be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene management.
  • the invention could be used to protect non-living materials from fungal attack, e.g. lumber, wall boards and paint.
  • the compounds of formula I are, for example, effective against the phytopathogenic fungi of the following classes: Fungi imperfecti (e.g. Botrytis spp., Alternaria spp.) and Basidiomycetes (e.g. Rhizoctonia spp., Hemileia spp., Puccinia spp., Phakopsora spp.). Additionally, they are also effective against Ascomycetes (e.g. Venturia spp., Blumeria spp., Podosphaera leucotricha, Monilinia spp., Fusarium spp., Uncinula spp., Mycosphaerella spp.
  • Fungi imperfecti e.g. Botrytis spp., Alternaria spp.
  • Basidiomycetes e.g. Rhizoctonia spp., Hemileia spp., Puccinia spp., Pha
  • target crops to be protected typically comprise the following species of plants: cereal (wheat, barley, rye, oat, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamomum, camphor) or plants such as tobacco
  • the target crops in accordance with the invention include conventional as well as genetically enhanced or engineered varieties such as, for example, insect resistant (e.g. Bt. And VIP varieties) as well as disease resistant, herbicide tolerant (e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®) and nematode tolerant varieties.
  • suitable genetically enhanced or engineered crop varieties include the Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.
  • the compounds of formula I are used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they are conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances.
  • the methods of application such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • the compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackif iers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
  • Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackif iers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.
  • the compounds of formula I are normally used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds.
  • further compounds can be e.g. fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.
  • the compounds of formula I are normally used in the form of fungicidal compositions for controlling and protecting against phytopathogenic microorganisms, comprising as active ingredient at least one compound of formula I, in free form or in agrochemically usable salt form, and at least one of the above-mentioned adjuvants.
  • the compounds of formula I can be mixed with other fungicides, resulting in some cases in unexpected synergistic activities.
  • Mixing components which are particularly preferred are: Azoles, such as azaconazole, BAY 14120, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole;
  • Pyrimidinyl carbinole such as ancymidol, fenarimol, nuarimol
  • 2-amino-pyrimidines such as bupirimate, dimethirimol, ethirimol
  • Morpholines such as dodemorph, fenpropidine, fenpropimorph, spiroxamine, tridemorph
  • Anilinopyrimidines such as cyprodinil, mepanipyrim, pyrimethanil;
  • Pyrroles such as fenpiclonil, fludioxonil
  • Phenylamides such as benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace, oxadixyl
  • Benzimidazoles such as benomyl, carbendazim, debacarb, fuberidazole, thiabendazole;
  • Dicarboximides such as chlozolinate, dichlozoline, iprodione, myclozoline, procymidone, vinclozoline;
  • Carboxamides such as boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide; guanidines, such as guazatine, dodine, iminoctadine;
  • Strobilurines such as azoxystrobin, dimoxystrobin (SSF 129), enestroburin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin;
  • Dithiocarbamates such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram;
  • N-halomethylthiotetrahydrophthalimides such as captafol, captan, dichlofluanid, fluoromides, folpet, tolyfluanid;
  • Cu-compounds such as Bordeaux mixture, copper hydroxide, copper oxychlo- ride, copper sulfate, cuprous oxide, mancopper, oxine-copper;
  • Nitrophenol-derivatives such as dinocap, nitrothal-isopropyl
  • Organo-p-derivatives such as edifenphos, iprobenphos, isoprothiolane, phosdiphen, pyrazophos, tolclofos-methyl; and
  • a method of controlling and preventing an infestation of crop plants or nonliving materials by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms which comprises the application of a compound of formula I as active ingredient to the plants, to parts of the plants or to the locus thereof, or to any part of the non-living materials.
  • a preferred method of controlling and preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, which comprises the application of a compound of formula I, or an agrochemical composition which contains at least one of said compounds, is foliar application.
  • the frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen.
  • the compounds of formula I can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field.
  • the compounds of formula I may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
  • a formulation that is, a composition containing the compound of formula I] and, if desired, a solid or liquid adjuvant or monomers for encapsulating the compound of formula I, is prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • extenders for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • the agrochemical formulations will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the compound of formula I, 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant.
  • Advantageous rates of application are normally from 5g to 2kg of active ingredient (a.i.) per hectare (ha), preferably from 10g to 1kg a.i./ha, most preferably from 2Og to 60Og a.iVha.
  • convenient dosages are from 10mg to 1 g of active substance per kg of seeds.
  • Table 1 provides 144 compounds of formula (l.a):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.c):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.d):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.e):
  • R , R and R y are as defined in Table 1.
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (Li):
  • R , R and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (I.I):
  • R , R and R are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.m):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.n):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • R , R and R are as defined in Table 1.
  • R , R and R are as defined in Table 1.
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.t):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.u):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.v):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.x):
  • R 37 , r R>8 b and R are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.y):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Alternaria solani/ tomato / preventive (Action against Alternaria on tomato) 4 weeks old tomato plants cv. Roter Gnom are treated with the formulated test compound in a spray chamber. Two days after application tomato plants are inoculated by spraying a spore suspension on the test plants. After an incubation period of 4 days at 22/18° C and 95% r. h. in a greenhouse the disease incidence is assessed.
  • Uncinula necator/ grape / preventive (Action against powdery mildew on grape) 5 weeks old grape seedlings cv. Gutedel are treated with the formulated test compound in a spray chamber.
  • grape plants are inoculated by shaking plants infected with grape powdery mildew above the test plants.

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Abstract

La présente invention concerne des nouveaux dérivés de triazolopyrimidine répondant à la formule (I) en tant que substances actives qui ont une activité microbiocide, en particulier une activité fongicide, les substituants étant tels que définis dans la revendication 1.
PCT/EP2005/013710 2004-12-22 2005-12-20 Nouveaux derives de triazolopyrimidine WO2006066874A1 (fr)

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EP04030438 2004-12-22
EP04030438.8 2004-12-22
EP05022957 2005-10-20
EP05022957.4 2005-10-20

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6297251B1 (en) * 1997-04-14 2001-10-02 American Cyanamid Co. Fungicidal trifluorophenyl-triazolopyrimidines

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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