EP1368351A2 - 7-(r)-amino-triazolopyrimidine, deren herstellung und verwendung zur bekämpfung von pflanzenpathogenen pilzen - Google Patents

7-(r)-amino-triazolopyrimidine, deren herstellung und verwendung zur bekämpfung von pflanzenpathogenen pilzen

Info

Publication number
EP1368351A2
EP1368351A2 EP01993385A EP01993385A EP1368351A2 EP 1368351 A2 EP1368351 A2 EP 1368351A2 EP 01993385 A EP01993385 A EP 01993385A EP 01993385 A EP01993385 A EP 01993385A EP 1368351 A2 EP1368351 A2 EP 1368351A2
Authority
EP
European Patent Office
Prior art keywords
methyl
formula
compounds
alkyl
weight
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.)
Withdrawn
Application number
EP01993385A
Other languages
German (de)
English (en)
French (fr)
Inventor
Jordi Tormo I Blasco
Klaus Ditrich
Hubert Sauter
Oliver Cullmann
Markus Gewehr
Wassilios Grammenos
Bernd Müller
Thomas Grote
Andreas Gypser
Joachim Rheinheimer
Ingo Rose
Peter Schäfer
Frank Schieweck
Eberhard Ammermann
Siegfried Strathmann
Gisela Lorenz
Reinhard Stierl
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP1368351A2 publication Critical patent/EP1368351A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the invention relates to 7- (R) -amino-triazolopyrimidines of the formula I.
  • R 3 is C 2 -C 10 alkyl, C 1 -C 4 alkoxymethyl, C 3 -C 10 cycloalkyl;
  • R4 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy;
  • n is a number from 1 to .5;
  • the invention further relates to a process for the preparation of the compounds of the formula I, agents for combating phytopathogenic fungi which contain the compounds I •, and the use of the compounds I for combating phytopathogenic fungi.
  • WO-A 98/46608 discloses racemic 5-halo-7- (fluoroalkyl) amino- ⁇ -phenyl-1,2,4-triazolo [1,5- ⁇ ] pyrimidene, the ⁇ -C- Atom of the 7- (fluoroalkyl) amino part is chiral and bears a CF 3 group. This document teaches that the respective S enantiomers would have particularly interesting fungicidal properties.
  • the present invention is based on the object of providing compounds with improved activity and / or widened activity spectrum.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl saturated, straight-chain or branched hydrocarbon radicals with 1 to 4, 6, 8 or 10 carbon atoms, e.g. '. -C 6 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methyl-butyl, 2-methylbutyl, 3rd -Methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-wench hylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1- Dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl,
  • Alkoxy straight-chain or branched alkyl groups with 1 to 4 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (-0-);
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 4, 6, 8 or 10 carbon atoms and a double bond in any position, for example C 2 -C 5 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1- Methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-l-propenyl, 2-methyl-l-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3- Pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl 2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, l-dimethyl-2
  • Alkynyl straight-chain or branched hydrocarbon groups with 2 to 4, 6, 8 or 10 carbon atoms and a triple bond in any position, e.g. C -Cg-alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4- Pentinyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3 ⁇ methyl-l-butynyl, 1, l-dimethyl-2-propynyl, l-ethyl-2- propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexy
  • Cycloalkyl monocyclic, saturated hydrocarbon groups with 3 to 10 carbon ring members, for example C 3 -C 8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl,
  • the compounds I can preferably be obtained by reacting a 7-halotriazolopyrimidine of the general formula II, in which the substituents R 4 and Y and the index n have the meaning given in claim 1, with (R) -configured amines of the formula 5 III.
  • reaction of the compound II with (R) -configured amines of the formula III takes place, for example, in an inert solution or
  • diluents such as a chlorinated hydrocarbon (in particular dichloromethane, trichloromethane), acetone, acetonitrile, dimethyl sulfoxide, dimethylformamide, N-methylpyrrolidone, an aromatic hydrocarbon (in particular toluene or chlorobenzene) or an ether (in particular tetrahydrofuran, dirnethoxyethane
  • the reaction is carried out using a base (for example sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride or in particular one)
  • a base for example sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride or in particular one
  • tertiary amine such as triethylamine, ethyldiisopropylamine or diazabicycloundecene have proven to be particularly suitable.
  • the bases are generally used in equimolar amounts or in excess. It may also be advantageous to use a catalytic amount of a crown ether (e.g.
  • the reaction temperature is generally in the range of 0 to 100 ° C, preferably 10 to '- 35 ° C.
  • the reaction at room temperature ⁇ can be performed '. 35
  • the 7-halotriazolopyrimidines II required for the preparation of the compounds I are known from the literature or can be prepared by methods known from the literature [cf. WO-A 98/46607; EP-A 550 113]. They are usually prepared by reacting 3-amino-1,2,4,4-triazole with 2-phenylmalonic esters or 5 2-phenylacetoacetic esters of the formula IV,
  • R 4 and the index n have the meaning given for formula I and R represents C 1 -C 4 alkyl.
  • 2-phenylmalonic esters (IVa) 5,7-dihydroxy-6-phenyltriazolopyrimidines can be obtained in this way, and 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidines are obtained with the diketones IVb.
  • the preparation of the starting compounds IV is described in EP-A 10 02 788. ,
  • the 5, 7-dihydroxy-6-phenyltriazolopyrimidines and 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidines obtained in this way are reacted with halogenating agents to give the '7-halotriazolopyrimidines of the formula II.
  • Chlorination or brominating agents such as phosphorus oxybromide, phosphorus oxychloride, thionyl chloride, thionyl bromide or sulfuryl chloride are preferably used.
  • the reaction can be carried out in bulk or in the presence of a solvent. Usual reaction temperatures are from 0 to 150 ° C or preferably from 80 to 125 ° C.
  • 3-dimethylbut-2-ylamine is profiled enantioselectively acylated with an ester whose acid component bears a fluorine, nitrogen, oxygen or sulfur atom adjacent to 'the Carbonylkohlenstoffa- toms in the presence of a hydrolase,
  • Proteases and in particular lipases are preferably used as hydrolases.
  • Lipases from Pseudomonas for example Amano P or the lipase from Pseudomonas spec. Are particularly suitable.
  • Other particularly suitable hydrolases are those from Novo Nordisk (Enzyme Toolbox) available enzymes, especially the lipases SP 523, SP 524, SP 525, SP 526 and Novozym® 435.
  • the enzyme used can be used in native or in immobilized form.
  • Amines of the formula III are either commercially available or accessible via racemate resolution as outlined in Scheme I.
  • R 1 represents hydrogen or methyl, in particular hydrogen.
  • R 1 , R 3 and (R 4 ) n have the meaning given for formula I.
  • n has the value 2 or 3, in particular 3.
  • R 4 fluorine, chlorine, methyl or methoxy, especially fluorine
  • n is the number 2 or 3, especially the number 3;
  • Y fluorine chlorine, bromine, methyl or methoxy, especially chlorine
  • Table 8 10 compounds of the formula IA in which R 1 is hydrogen, R 3 is n-heptyl and the combination of the radicals (R) n for a compound corresponds in each case to one line of Table A.
  • Table 9 15 compounds of the formula IA, in which R 1 is hydrogen, R 3 is n-octyl and the combination of the radicals (R) n for each compound corresponds to one row of Table A.
  • Table 10 20 compounds of the formula IA, in which R 1 is hydrogen, R 3 is n-nonyl and the combination of the radicals (R 4 ) n for a compound corresponds in each case to one line of Table A.
  • Table 11 25 compounds of the formula IA, in which R 1 is hydrogen, R 3 iso-butyl and the combination of the radicals (R 4 ) n corresponds to one row of Table A for each compound
  • Table 12 30 compounds of the formula IA, in which R 1 is hydrogen, R 3 is cyclopropyl and the combination of the radicals (R 4 ) n for each compound corresponds to one row of Table A.
  • Table 13 35 compounds of the formula IA, in which R 1 is hydrogen, R 3 is cyclohexyl and the combination of the radicals (R) n for each compound corresponds to one row of Table A.
  • Table 14 40 compounds of the formula IA, in which R 1 is hydrogen, R 3 is methoxymethyl and the combination of the radicals (R 4 ) n for each compound corresponds to one row of Table A.
  • Table 15 45 Compounds of the formula IA, in which R 1 is methyl, R 3 is ethyl ' and the combination of the radicals (R 4 ) n for each compound because it corresponds to one row of table A.
  • the new compounds I are notable for excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes. and Basidio - mycetes, from and can be used as leaf and soil fungicides. Some of them have remarkably high systemic mobility and effectiveness after soil application and especially after leaf application.
  • Alternaria species Podosphaera species, Sclerotinia species, Physallospora canker on vegetables and fruits, Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines,
  • Phaeoisariopsis vitis and Sphaceioma ampelina on grapefruit, • Pseudocercosporella herpotrichoides on wheat and barley,
  • Rhizoctonia species on cotton, rice and lawn • Stagonospora nodorum and Septoria tritici on wheat,
  • Venturia species scab on apples and pears.
  • the compounds I are also suitable for combating harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds.
  • the application can take place both before and after the infection of the materials, plants or seeds by the fungi.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
  • active ingredient 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.
  • the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably
  • the compounds I can be converted into the customary formulations, for example solutions, emulsions, 'suspensions, dusts, powders, pastes and granules.
  • the form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compound according to the invention.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, where, in the case of water as the diluent, other organic solvents can also be used as auxiliary solvents.
  • auxiliaries solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g.
  • Ethanolamine, dimethylformamide) and water such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
  • Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfit
  • Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid sulfates, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, 'fatty alcohol sulfates and fatty acids and their alkali and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ethers, condensates of sulfonated Naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or.
  • naphthalene sulfonic acid with phenol and formaldehyde polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octyphenol, nonylphenol, alkylphenol - polyglycol ether, tributylphenylpolyglycol ether, alkylarylpolyether alcohols, isotridecyl alcohol, fatty alcohol ethoxylated alcohol, ethoxylated alcohol, ethoxylated alcohol, ethoxylated alcohol, ethoxylated ethoxylated soxyl ether bitester, lignin sulfate and methyl cellulose.
  • emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or "animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, -xylene, Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, for example dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil
  • coal tar oils and oils of vegetable or "animal origin aliphatic, cyclic and aromatic hydrocarbon
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Solid carriers are, for example, mineral earths, such as silica gel, silicas, silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess " , clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess " , clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, am
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum). Examples of formulations are:
  • V. 80 parts by weight of a compound according to the invention are powdered with 3 parts by weight of the sodium salt of diisobutylnaphthalene-al-'-phasulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight Mix the silica gel well and grind it in a hammer mill (active ingredient content 80% by weight).
  • VIII.20 parts by weight of a compound according to the invention are mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene- ⁇ -sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel well mixed and ground in a hammer mill.
  • a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
  • IX 10 parts by weight of the compound according to the invention are dissolved in 63 parts by weight of cyclohexanone, 27 parts by weight of dispersant (for example a mixture of 50 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 50 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil).
  • dispersant for example a mixture of 50 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 50 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil.
  • the stock solution is then diluted to the desired concentration by distribution in water, e.g. to a concentration in the range of 1 to 100 ppm.
  • the active ingredients as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes; Dusts, sprinkles, granules by spraying, atomizing, dusting, scattering or pouring can be used.
  • the application forms depend entirely on the intended use; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders ('wettable powders, oil dispersions) by adding water.
  • emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • wetting, adhesive wetting, adhesive,
  • Dispersants or emulsifiers and possibly solvents or oil existing concentrates are prepared which are suitable for dilution with water.
  • the active substance concentrations in the ready-to-use preparations can be varied over a wide range. Generally they are between 0.0001 and 10%. Often enough Small amounts of active ingredient compound I are already present in the ready-to-use preparation, for example 2 to 200 ppm. Ready-to-use preparations with active ingredient concentrations in the range from 0.01 to 1% are also preferred.
  • the active ingredients can also be used with great success - in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume process
  • Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
  • compositions according to the invention can also be present together with other active compounds which, e.g. with herbicides, insecticides, growth regulators, fungicides or even with fertilizers. Mixing the compounds I or the compositions containing them in the use form as fungicides with other fungicides results in an enlargement of the fungicidal spectrum of action in many cases.
  • Sulfur, dithiocarbamates and their derivatives such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese zinc ethylenediamine bis dithiocarbamate, tetramethylthiaminodithate dithi disamide di ), Ammonia complex of zinc (N, N '-propylene-bis-dithiocarbamate), zinc (N, N' -propylene-bis-dithiocarbamate), N, N '-polypropylene-bis- (thiocarbamoyl) disulfide;
  • Nitroderivate such as dinitro- (1-methylheptyl) phenylcrotonate, 2-sec-butyl-4, 6-dinitrophenyl-3, 3-dimethylacrylate, 2-sec-butyl-4, 6-dinitrophenyl-isopropyl carbonate, 5- Nitro-isophthalic acid-di-isopropyl ester; Heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate, 2-chloro-N- (4'-chlorobiphenyl-2-yl) -nicotinamide, 2,4-di-chloro-6- (o -chloranilino) -s-triazine, 0, O-diethyl-phthalimidophosphonothioate, 5-amino-l- [bis- (dimethylamino) -phosphinyl] -3-phenyl-l, 2, 4-triazole, 2, 3-dicyano-l, -di
  • Strobilurins such as methyl-E-methoxyimino- [ ⁇ - (o-tolyloxy) -o ⁇ to- lyl] ace ' tat, methyl-E-2- ⁇ 2- [6- (2-cyanophenoxy) pyrimidine-4- yl - oxy] -phenyl ⁇ -3-methoxyacrylate, methyl-E-methoxyimino- [ ⁇ - (2-phenoxyphenyl)] -acetamide, methyl-E-methoxyimino- [ ⁇ - (2, 5-dimethyl-phenoxy) -o -tolyl] -acetamide, methyl-E-2- ⁇ 2- [2-trif luorme - thylpyridyl-6-] oxymethyl] -phenyl ⁇ 3 -methoxyacrylate, (E, E) ⁇ metho - ximino- ⁇ 2- [1 - (3-trifluoromethylphenyl
  • Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acrylic acid morpholide, 3- (4-fluorophenyl) -3- (3,4-dimethoxyphenyl) acrylic acid morpholide,
  • fungicides such as dodecylguanidine acetate, 1- (3-bromo-6-methoxy-2-methylphenyl) -1- (2,3,4-trimethoxy-6-methylphenyl) methanone, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, hexachlorobenzene, DL-methyl-N- (2,6-dimethylphenyl) -N-furoyl (2) alaninate,
  • the low volatility swamp consisted of R-DMBAmid and unreacted acylation medium, iso-propyl methoxyacetate. This low-volatility mixture was again passed through the thin-film evaporator. Now a jacket temperature of 140 ° C and a head pressure of 35 mbar was set. The unconverted acyly-
  • R-DMBAmid 10 190 g (1.1 mol) of R-DMBAmid was diluted with 100 g of triethanolamine and heated to 120 ° C. with stirring. At this temperature, 150 g of 50% sodium hydroxide solution and then 100 g of water were added within two hours.
  • the active compounds separately or jointly 'as a 10% emulsion in a mixture of 70 wt .-% of cyclohexanone, 20 wt .-% Nekanil® LN (Lutensol® AP6, wetting agent having emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight Wettol® EM (non-ionic emulsifier based on ethoxylated castor oil) prepared and diluted with water according to the desired concentration.
  • Nekanil® LN Litensol® AP6, wetting agent having emulsifying and dispersing action based on ethoxylated alkylphenols
  • Wettol® EM non-ionic emulsifier based on ethoxylated castor oil
  • WO-A 98/46607 describes some of the compounds listed below as a racemate. Furthermore, on page 7, paragraphs 1 and 2, in particular with regard to compounds with a haloalkylamine substitution in the 7-position, the preference for the S-enantiomers is emphasized. The present compounds have a non-halogenated alkylamine part in the 7-position. By analogy, one would also have an increased effectiveness of the S- Enantiomers expected. In the following experiments the R-enantiomer and the S-enantiomer are compared.
  • Example of use 1 Curative activity against wheat brown rust caused by Puccinia recondi ta
  • aqueous active compound preparation which was prepared from a stock solution consisting of 10% active compound, 85% cyclohexanone and 5% emulsifier
  • Example of use 3 Protective activity against the Septoria leaf spot disease of the wheat caused by Septoria tri tici
  • aqueous preparation of active compound which was prepared from a stock solution consisting of 10% active compound, 85% cyclohexanone and 5% emulsifier. 24 hours after the spray coating had dried on, they were inoculated with an aqueous spore suspension of Septoria tri tici. The suspension contained 2.0 x 106 spores / ml. The test plants were then placed in a greenhouse at temperatures between 18 and 22 ° C and a relative humidity close to 100%. After 2 weeks, the extent of the development of the disease was determined visually in% of the total leaf area.
  • Example of use 4 Efficacy against wheat flour caused by Blumeria graminis forma specialis tri tici
  • aqueous active compound preparation which was prepared from a stock solution consisting of 10% active compound, 85% cyclohexanone and 5% emulsifier, and 24 hours after the spray coating had dried on, with spores of wheat powdery mildew (Blumeria graminis forma specialis tri tici) pollinated.
  • the test plants were then placed in a greenhouse at temperatures between 20 and 24 ° C and 60 to 90% relative atmospheric humidity. After 7 days, the extent of mildew development was determined visually in% infestation of the entire leaf area.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP01993385A 2000-11-13 2001-11-09 7-(r)-amino-triazolopyrimidine, deren herstellung und verwendung zur bekämpfung von pflanzenpathogenen pilzen Withdrawn EP1368351A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10056101 2000-11-13
DE10056101 2000-11-13
PCT/EP2001/012977 WO2002038565A2 (de) 2000-11-13 2001-11-09 7-(r)-amino-triazolopyrimidine, deren herstellung und verwendung zur bekämpfung von pflanzenpathogenen pilzen

Publications (1)

Publication Number Publication Date
EP1368351A2 true EP1368351A2 (de) 2003-12-10

Family

ID=7663068

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01993385A Withdrawn EP1368351A2 (de) 2000-11-13 2001-11-09 7-(r)-amino-triazolopyrimidine, deren herstellung und verwendung zur bekämpfung von pflanzenpathogenen pilzen

Country Status (5)

Country Link
US (2) US6855718B2 (enExample)
EP (1) EP1368351A2 (enExample)
JP (1) JP2004513170A (enExample)
AU (1) AU2002221831A1 (enExample)
WO (1) WO2002038565A2 (enExample)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6255309B1 (en) * 1999-03-19 2001-07-03 American Cyanomid Co. Fungicidal trifluoromethylalkylamino-triazolopyrimidines
DE10124208A1 (de) * 2001-05-18 2002-11-21 Bayer Ag Verwendung von Triazolopyrimidin-Derivaten als Mikrobizide
IL159606A0 (en) * 2001-07-18 2004-06-01 Basf Ag Substituted 6-(2-tolyl)-triazolopyrimidines as fungicides
UA80304C2 (en) * 2002-11-07 2007-09-10 Basf Ag Substituted 6-(2-halogenphenyl)triazolopyrimidines
US7419982B2 (en) 2003-09-24 2008-09-02 Wyeth Holdings Corporation Crystalline forms of 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine salts
AU2004276240A1 (en) 2003-09-24 2005-04-07 Wyeth Holdings Corporation 6-[(substituted)phenyl]triazolopyrimidines as anticancer agents
DE10347090A1 (de) * 2003-10-10 2005-05-04 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
DE10349501A1 (de) * 2003-10-23 2005-05-25 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
PE20050594A1 (es) * 2003-12-17 2005-10-18 Basf Ag 6-(2-fluoro-4-alcoxifenil)-triazolopirimidinas y procedimientos para su preparacion
CN1894254A (zh) * 2003-12-17 2007-01-10 巴斯福股份公司 用于防治病原性真菌的6－(2,3,6－三氟苯基)三唑并嘧啶
EP1697364A1 (de) * 2003-12-17 2006-09-06 Basf Aktiengesellschaft 6-pentafluorphenyl-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bek mpfung von schadpilzen sowi e sie enthaltende mittel
EP1697373A1 (de) * 2003-12-17 2006-09-06 Basf Aktiengesellschaft 6-(2,4,6-trihalogenphenyl)-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bek mpfung von schadpil zen sowie sie enthaltende mittel
WO2005058906A1 (de) * 2003-12-17 2005-06-30 Basf Aktiengesellschaft 6-(2-chlor-4-alkoxy-phenyl)-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel
DE10359445A1 (de) * 2003-12-17 2005-07-28 Enginion Ag Wasserstoff-Verbrennungsmotor
US20070208038A1 (en) * 2004-03-30 2007-09-06 Basf Aktiengesellschaft 6-(2-Fluorophenyl)-Triazolopyrimidines, Method for Producing Them, Their use for Controlling Parasitic Fungi and Agents Containing the Same
KR20070029257A (ko) * 2004-06-22 2007-03-13 바스프 악티엔게젤샤프트 6-(2-톨릴)-트리아졸로피리미딘의 살진균제로서의 용도,신규 6-(2-톨릴)-트리아졸로피리미딘, 이의 제조 방법,유해 진균류 방제를 위한 이의 용도, 및 이를 함유하는제제
KR20070104516A (ko) * 2004-09-08 2007-10-26 바스프 악티엔게젤샤프트 6-페닐-7-아미노-트리아졸로피리미딘, 이의 제조 방법,병원성 진균을 방제하기 위한 상기 화합물의 용도, 및 상기화합물을 포함하는 제제
DE102005015677A1 (de) 2005-04-06 2006-10-12 Bayer Cropscience Ag Synergistische fungizide Wirkstoffkombinationen
DE102005026255A1 (de) * 2005-06-08 2006-12-21 Bayer Cropscience Ag Fungizide Wirkstoffkombinationen
DE102005026577A1 (de) * 2005-06-08 2006-12-14 Bayer Cropscience Ag Verwendung von Triazolopyrimidinen zur Kontrolle von Pflanzenkrankheiten an Hülsenfrüchten
DE102005026482A1 (de) 2005-06-09 2006-12-14 Bayer Cropscience Ag Wirkstoffkombinationen
EP2255645A3 (de) 2005-06-09 2011-03-16 Bayer CropScience AG Wirkstoffkombinationen
WO2007101810A1 (de) * 2006-03-08 2007-09-13 Basf Se Substituierte triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel
DE102006023263A1 (de) * 2006-05-18 2007-11-22 Bayer Cropscience Ag Synergistische Wirkstoffkombinationen
EP1952691A3 (en) * 2007-01-31 2008-09-17 Basf Se Method for improving plant health by application of a triazolopyrimidine derivative
DE102007045920B4 (de) 2007-09-26 2018-07-05 Bayer Intellectual Property Gmbh Synergistische Wirkstoffkombinationen
WO2010108507A2 (de) 2009-03-25 2010-09-30 Bayer Cropscience Ag Synergistische wirkstoffkombinationen
CN103548836A (zh) * 2009-07-16 2014-02-05 拜尔农作物科学股份公司 含苯基三唑的协同活性物质结合物
CN102665414B (zh) 2009-12-22 2015-11-25 三井化学Agro株式会社 植物病害防除组合物及施用其的植物病害的防除方法
EP2910126A1 (en) 2015-05-05 2015-08-26 Bayer CropScience AG Active compound combinations having insecticidal properties

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5593996A (en) * 1991-12-30 1997-01-14 American Cyanamid Company Triazolopyrimidine derivatives
TWI252231B (en) * 1997-04-14 2006-04-01 American Cyanamid Co Fungicidal trifluorophenyl-triazolopyrimidines
TW460476B (en) 1997-04-14 2001-10-21 American Cyanamid Co Fungicidal trifluoromethylalkylamino-triazolopyrimidines
US6117876A (en) * 1997-04-14 2000-09-12 American Cyanamid Company Fungicidal trifluorophenyl-triazolopyrimidines
US5981534A (en) * 1998-09-25 1999-11-09 American Cyanamid Company Fungicidal 6-(2,6-difluoro-4-alkoxyphenyl)-triazolopyrimidines
US5985883A (en) 1998-09-25 1999-11-16 American Cyanamid Company Fungicidal trichlorophenyl-triazolopyrimidines
JP2000103790A (ja) * 1998-09-25 2000-04-11 American Cyanamid Co 殺菌・殺カビ性のトリハロフェニル―トリアゾロピリミジン類
US5986135A (en) * 1998-09-25 1999-11-16 American Cyanamid Company Fungicidal trifluoromethylalkylamino-triazolopyrimidines
BR0112038A (pt) * 2000-06-30 2003-04-01 Wyeth Corp Triazolopirimidinas substituìdas como agentes anticâncer
IL159606A0 (en) * 2001-07-18 2004-06-01 Basf Ag Substituted 6-(2-tolyl)-triazolopyrimidines as fungicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0238565A3 *

Also Published As

Publication number Publication date
US20060135538A1 (en) 2006-06-22
US6855718B2 (en) 2005-02-15
WO2002038565A2 (de) 2002-05-16
AU2002221831A1 (en) 2002-05-21
WO2002038565A3 (de) 2003-10-09
US20040110771A1 (en) 2004-06-10
JP2004513170A (ja) 2004-04-30

Similar Documents

Publication Publication Date Title
EP1368351A2 (de) 7-(r)-amino-triazolopyrimidine, deren herstellung und verwendung zur bekämpfung von pflanzenpathogenen pilzen
EP1414302A1 (de) 7-aminotriazolopyrimidine zur bekämpfung von schadpilzen
DE60202672T2 (de) 5-halogen-6-phenyl-7-fluoroalkylamino-triazolopyrimidine als fungizide
DE60201089T2 (de) 6-(2-chlor-6-fluor-phenyl)-triazolpyrimidine
EP0970044A1 (de) Cycloalkylalkancarbonsäureamide, deren herstellung und verwendung
EP1085807A1 (de) Verwendung von 2-(n-phenylamino)pyrimidinen als fungizide sowie neue 2-(n-phenylamino)pyrimidine
EP1504001A1 (de) 2-(2-pyridyl)-5-phenyl-6-aminopyrimidine, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen
EP1504009B1 (de) Fungizide triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bek mpfung von schadpilzen sowie sie ent haltende mittel
EP0778824A1 (de) Carbamoylcarbonsäureamide
EP0763014A1 (de) Carbamoylcarbonsäurehydrazide und ihre verwendung zur bekämpfung von schadpilzen
EP0847384A1 (de) Carbamoylcarbonsäureamide
EP1172355B1 (de) Salicylsäure-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende Mittel sowie ihre Verwendung zur Bekämpfung von Schadpilzen
EP0852579A1 (de) Fungizide chinoline
DE60104087T2 (de) Fungizide 5-Alkylamino-6-phenyl-7-halogen-Triazolopyrimidine
EP0653417B1 (de) P-Hydroxyanilinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen oder Schädlingen
EP1295877A1 (de) Xanthonderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Schadpilzen sowie sie enthaltende Mittel
EP1107946B1 (de) Cycloalkylcarbonsäureamide, deren herstellung und verwendung als fungizide im agrarbereich
WO1997046518A1 (de) Carbamoylcarbonsäureamidoxime
EP1017671A1 (de) Neue benzamidoxim-derivate, zwischenprodukte und verfahren zu deren herstellung und deren verwendung als fungizide
DE19531814A1 (de) Carbamoylcarbonsäureamide
WO2001014322A1 (de) Cycloalkylalkancarbonsäureamide, deren herstellung und verwendung
EP0912525A1 (de) Pyrimidin-4-carbonsäureamide
WO1996024249A1 (de) Fungizides mittel
EP1492768A1 (de) Phenethylacrylamide, verfahren zu deren herstellung sowie sie enthaltende mittel
EP0990642A1 (de) Cycloalkylcarbonsäureamide, deren Herstellung und Verwendung als Fungizide

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

17P Request for examination filed

Effective date: 20040413

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Effective date: 20070724