WO2006100037A1 - Derives de triazolopyrimidine utilises comme microbiocides - Google Patents

Derives de triazolopyrimidine utilises comme microbiocides Download PDF

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WO2006100037A1
WO2006100037A1 PCT/EP2006/002590 EP2006002590W WO2006100037A1 WO 2006100037 A1 WO2006100037 A1 WO 2006100037A1 EP 2006002590 W EP2006002590 W EP 2006002590W WO 2006100037 A1 WO2006100037 A1 WO 2006100037A1
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formula
independently
compound
hydrogen
halogen
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PCT/EP2006/002590
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Clemens Lamberth
Sebastian Wendeborn
Kurt Nebel
Patrick Jelf Crowley
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Syngenta Participations Ag
Syngenta Limited
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    • 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 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 and non-living materials by phytopathogenic microorganisms, preferably fungi.
  • the present invention provides a compound of formula I:
  • R 1 , R 2 , R 3 , R 4 , R 10 , R 11 , R 12 and R 13 are hydrogen, halogen, CpCealkyl, (VC ⁇ haloalkyl, CrCealkyloxy, C 1 - C 6 acyloxy or cyano; or
  • R 5 and R 6 are hydrogen, halogen, Ci-C 6 alkyl, C 1 - C 6 haloalkyl or C-i-C 6 alkyloxy;
  • R 7 is an optionally substituted aryl, or heteroaryl;
  • R 8 is Ci-C 6 alkyl, halogen or cyano;
  • R 9 is hydrogen, mercapto or Ci-C 3 alkylthio;
  • X is oxygen, sulfur or N-R 16 ;
  • R 14 , R 15 and R 16 each independently of each other are hydrogen, halogen, Ci-C 6 alkyl, C 1 - C 6 haloalkyl or CrC 6 alkyloxy; m, n and j, independently of each other, are 0, 1 , 2, 3 or 4; (m + n) is equal to 0, 1, 2, 3 or 4; t is 1 , 2, 3 or 4; and w is 0, 1 or 2.
  • w is 1 or 2.
  • j is 1 , 2, 3, or 4.
  • the R 1 and R 2 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 1 as ethyl and by R 2 as bromine and the second carbon atom can be substituted by R 1 as methyl and by R 2 as methoxy.
  • the same situation could happen to (R 3 R 4 C) n when n is 2, 3 or 4, for R 3 and R 4 , and to (R 10 R 11 C)] when j is 2, 3 or 4, for R 10 and R 11 , respectively.
  • 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, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, indazolyl, benzotriazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl and naphthyridinyl.
  • Each heteroaryl can be linked by a carbon atom or by
  • 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- trifluoromethylphenyl, 2-fluor
  • 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, CHCl 2 , CCI 3 , CH 2 F, CHF 2 , CF 3 , CF 3 CH 2 , CH 3 CF 2 , CF 3 CF 2 or CCl 3 CCI 2 .
  • 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.
  • R 1 is part of an endocyclic bound or R 5 forms an endocyclic bound, that R 1 and R 5 respectively are taking part in the formation of the endocyclic double bound and no longer are substituents.
  • the compounds of formula I according to the invention are in free form or in an agronomically usable salt form.
  • Preferred subgroups of compounds of formula I according to the invention are those wherein R 1 , R 2 , R 3 , R 4 , R 10 , R 11 , R 12 and R 13 , each independently of each other and independently of anyone of m, n, j and t, are hydrogen, halogen, d-C 6 alkyl, CrC 6 haloalkyl,
  • R 5 and R 6 are hydrogen, halogen, Ci-C 6 alkyl, C 1 - C 6 haloalkyl or C r C 6 alkyloxy;
  • R 7 is an optionally substituted aryl, or heteroaryl
  • R 8 is Ci-C 6 alkyl, halogen or cyano
  • R 9 is hydrogen, mercapto or C r C 3 alkylthio
  • X is oxygen, sulfur or N-R 16 .
  • (m + n) is equal to 0, 1 , 2, 3 or 4;
  • (w + j) is equal to 1 , 2, 3, 4 or 5.
  • More preferred subgroups of compounds of formula I according to the invention are those wherein R 1 , R 2 , R 3 , R 4 , R 10 , R 11 , R 12 and R 13 , each independently of each other and independently of anyone of m, n, j and t, are hydrogen, halogen or C r C 6 alkyl;
  • R 5 and R 6 are hydrogen, halogen or C-rC 6 alkyl; R 7 is an optionally substituted aryl; R 8 is CrC 3 alkyl or halogen; R 9 is hydrogen, mercapto or methylthio; X is oxygen, sulfur or N-methyl.
  • (m + n) is equal to 0, 1 , 2 or 3; (w + j) is equal to 1 , 2, 3 or 4.
  • R 1 , R 2 , R 3 , R 4 , R 10 , R 11 , R 12 and R 13 are hydrogen or CrC 3 alkyl
  • R 5 and R 6 are hydrogen or methyl
  • R 7 is phenyl substituted at least in one o/iffro-position with halogen
  • R 8 is chloro or fluoro
  • R 9 is hydrogen or mercapto
  • X is oxygen or N-methyl. (m + n) is equal to 0, 1 or 2;
  • (w + j) is equal to 1 , 2 or 3.
  • Especially preferred subgroups of compounds of formula I according to the invention are those wherein R 1 , R 2 , R 3 , R 4 , R 10 , R 11 , R 12 and R 13 , each independently of each other and independently of anyone of m, n, j and t, are hydrogen or methyl;
  • R 5 and R 6 are hydrogen
  • R 7 is 2,4,6-trifluorophenyl or 2-chloro-6-fluorophenyl
  • R 8 is chloro
  • R 9 is hydrogen; X is oxygen.
  • Preferred individual compounds are: 5-chloro-7-(5-methyl-2-aza-bicyclo[2.1.1]hex-2-yl)-6-(2,4,6-trifluoro-phenyl)- [1 ,2,4]triazolo[1 ,5-a]pyrimidine (Compound No.l.d.081), 5-chloro-6-(2-chloro-6-fluoro-phe ⁇ y!)-7-(5-methyl-2-aza-bicyclo[2.1.1 ]hex-2-yl)-
  • 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 , R 10 , R 11 , R 12 , R 13 , X, m, n, j, t and w 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,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 cyclic amines with compounds of formula Il is already described in WO 98/46607, US 6297251 and US 6117876.
  • 7-aza-bicyclo[2.2.1]heptanes (7-azanorbornanes) of formula (IHb) can also be obtained from different 4-acetamidophenols of formula (IX), following a route described in Can J. Chem. 1970, 48, 2065 - 2074 and J. Am. Chem. Soc. 1989, 111 , 1776 - 1781.
  • 2-aza-bicyclo[2.2.2]octanes of formula (Wc) may be obtained from 4- amino-benzoic acids of formula (XII, following a route described in Synth. Commun. 2002, 32, 1985 - 1995.
  • 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 protecting 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.).
  • Fungi imperfecti e.g. Botrytis spp., Alternaria spp.
  • Basidiomycetes e.g. Rhizoctonia spp., Hemileia spp., Puccinia spp., Phakopsora spp.
  • Ascomycetes e.g. Venturia spp., Blumeria spp., Podosphaera leucotricha, Monilinia spp., Fusarium spp., Uncinula spp., Mycosphaerella spp., Pyrenophora spp., Rhynchosporium secalis, Magnaporthe spp., Colletotrichum spp.
  • Oomycetes e.g. Phytophthora spp., Pythium spp., Plasmopara spp.
  • Outstanding activity has been observed against powdery mildews (e.g.
  • Uncinula necator Uncinula necator
  • rusts e.g. Puccinia spp.
  • leaf spots e.g. Septoria tritici
  • novel compounds of formula I are effective against phytopathogenic bacteria and viruses (e.g. against Xanthomonas spp, Pseudomonas spp, Erwinia amylovora as well as against the tobacco mosaic virus).
  • 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 tackifiers 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, tackifiers, 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:
  • Azotes 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 carbinoles, 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, procymi- done, 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;
  • 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-halomethylthiotetrahydrophtha ⁇ mides such as captafol, captan, dichlofluanid, fluoromides, folpet, tolyfluanid;
  • Cu-compounds such as Bordeaux mixture, copper hydroxide, copper oxychloride, 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 of non-living 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 1 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.i./ha.
  • convenient dosages are from 10mg to 1g of active substance per kg of seeds.
  • Example 1 This example illustrates the preparation of 5-chloro-7-(3-chloro-8-aza- bicyclo[3.2.1]oct-8-yl)-6-(2,4,6-thfluoro-phenyI)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine (Compound No.l.q.081) a) Preparation of 8-[5-chloro-6-(2,4,6-trifluoro-phenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidin-7- yl]-8-aza-bicyclo[3.2.1]octan-3-ol (Compound No. I.O.081)
  • Table 1 provides 144 compounds of formula (l.a):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • R ->7 , r R-,8 and I D R9 are as defined in Table 1.
  • R ⁇ 7, R 08 a _ _nd_! R r-)9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.e):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.f):
  • R ⁇ J , ⁇ R U 8 a __nd j i R->9 are as defined in Table 1.
  • Table 1 provides 144 compound ' s of formula (l.h):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (U):
  • R , R and R are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (I.I):
  • R 7 , R 8 and R 9 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 (Lo):
  • 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.r):
  • R -.7 , R Q 8 and j o R8 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.s):
  • R 3 7 , D RS are as defined in Table 1.
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • R , R :>8 and j R are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.x):
  • R 7 , R 8 and R 9 are as defined in Table 1.
  • Table 1 provides 144 compounds of formula (l.y):
  • R 5 7 , D R8 and R are as defined in Table 1.
  • Table 2 shows selected melting point and selected NMR data, all with CDCI 3 as the solvent (unless otherwise stated, no attempt is made to list all characterising data in all cases) for compounds of Table 1.
  • Table 2 Melting point and selected NMR data for compounds of Table 1
  • Alternaria solani/ tomato / preventive (Action against Altemaria 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.
  • plants After an incubation period of 1 day at 2Oo C and 95% r. h. plants are kept for 10 days 20° C / 18° C (day/night) and 60% r.h. in a greenhouse. The disease incidence is assessed 11 days after inoculation.
  • Mapnaporthe ⁇ risea (Pyricularia orvzae) I rice / preventive (Action against rice blast) 3 weeks old rice plants cv. Koshihikari are treated with the formulated test compound in a spray chamber. Two days after application rice plants are inoculated by spraying a spore suspension (1 x 10 5 conidia/ml) on the test plants. After an incubation period of 6 days at 25° C and 95% r. h. the disease incidence is assessed.
  • plants After an incubation period of 1 day at 22°C/21 0 C and 95% r. h. plants are kept at 22°C/21°C and 70% r.h. in a greenhouse. The disease incidence is assessed 16 - 18 days after inoculation.
  • 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. After an incubation period of 7 days at 24/22° C and 70% r. h. under a light regime of 14/10 h (light/dark) the disease incidence is assessed.

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  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne de nouveaux dérivés de triazolopyrimidine de la formule (1) utilisés comme ingrédients actifs à activité microbiocide, en particulier fongicide, les substituants étant tels que définis dans la revendication 1.
PCT/EP2006/002590 2005-03-23 2006-03-21 Derives de triazolopyrimidine utilises comme microbiocides WO2006100037A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05006387 2005-03-23
EP05006387.4 2005-03-23

Publications (1)

Publication Number Publication Date
WO2006100037A1 true WO2006100037A1 (fr) 2006-09-28

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PCT/EP2006/002590 WO2006100037A1 (fr) 2005-03-23 2006-03-21 Derives de triazolopyrimidine utilises comme microbiocides

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Country Link
AR (1) AR053343A1 (fr)
GT (1) GT200600122A (fr)
TW (1) TW200700421A (fr)
WO (1) WO2006100037A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1980150A1 (fr) 2007-04-13 2008-10-15 Basf Se Mélanges fongicides basés sur des composés de triazolopyrimidines
WO2009007115A1 (fr) * 2007-07-12 2009-01-15 Syngenta Participations Ag Dérivés de tropane utiles comme pesticides
US8691727B2 (en) 2005-05-03 2014-04-08 Syngenta Crop Protection, Llc Pesticidal compositions
EP4136089A4 (fr) * 2020-04-14 2024-05-29 The Trustees of The University of Pennsylvania Composés de {1,2,4,} triazolo{1,5-a} pyrimidine substitués et leur utilisation dans la stabilisation de microtubules

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998046607A1 (fr) * 1997-04-14 1998-10-22 American Cyanamid Company Trifluorophenyl-triazolopyrimidines fongicides
WO2002088127A2 (fr) * 2001-04-27 2002-11-07 Bayer Cropscience Ag Triazolopyrimidines
WO2003091254A1 (fr) * 2002-04-26 2003-11-06 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines
WO2003093271A1 (fr) * 2002-05-03 2003-11-13 Basf Aktiengesellschaft Triazolopyrimidines fongicides, leurs procedes de production et leur utilisation pour la lutte contre des champignons nuisibles, et agents contenant ces composes

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998046607A1 (fr) * 1997-04-14 1998-10-22 American Cyanamid Company Trifluorophenyl-triazolopyrimidines fongicides
WO2002088127A2 (fr) * 2001-04-27 2002-11-07 Bayer Cropscience Ag Triazolopyrimidines
WO2003091254A1 (fr) * 2002-04-26 2003-11-06 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines
WO2003093271A1 (fr) * 2002-05-03 2003-11-13 Basf Aktiengesellschaft Triazolopyrimidines fongicides, leurs procedes de production et leur utilisation pour la lutte contre des champignons nuisibles, et agents contenant ces composes

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8691727B2 (en) 2005-05-03 2014-04-08 Syngenta Crop Protection, Llc Pesticidal compositions
EP1980150A1 (fr) 2007-04-13 2008-10-15 Basf Se Mélanges fongicides basés sur des composés de triazolopyrimidines
WO2009007115A1 (fr) * 2007-07-12 2009-01-15 Syngenta Participations Ag Dérivés de tropane utiles comme pesticides
JP2010532777A (ja) * 2007-07-12 2010-10-14 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 殺有害生物剤として有用なトロパン誘導体
CN101765599B (zh) * 2007-07-12 2012-08-22 先正达参股股份有限公司 用作农药的托烷衍生物
EP4136089A4 (fr) * 2020-04-14 2024-05-29 The Trustees of The University of Pennsylvania Composés de {1,2,4,} triazolo{1,5-a} pyrimidine substitués et leur utilisation dans la stabilisation de microtubules

Also Published As

Publication number Publication date
TW200700421A (en) 2007-01-01
GT200600122A (es) 2006-11-09
AR053343A1 (es) 2007-05-02

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