Classifications

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

Definitions

• the present invention relates to 7-alkenylamine triazolopyrimidines of the formula I.
• R 2 is hydrogen, -C 3 alkyl or C ⁇ -C 3 haloalkyl
• R 3 C 2 -C 10 alkenyl, which can be unsubstituted or partially or completely halogenated or can carry one to three groups R a :
• R a halogen, cyano, nitro, hydroxy, C r C 6 alkylcarbonyl, C 3 -C 6 cycloalkyl, CC 6 alkoxy, Ci-Ce haloalkoxy, C r C 6 alkoxycarbonyl, CrC 6 alkylthio, CC 6 Alkylamino, di-CrC 6 -alkylamino, C -C 6 alkenyl, C 2 -C 6 alkenyloxy, C 3 - C 6 alkynyloxy or C 3 -C 6 cycloalkyl,
• R b halogen, cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, alkyl, haloalkyl, alkenyl, alkenyloxy, alkynyloxy, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamino, Formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylamino thiocarbonyl, dialkylaminothiocarbonyl, the alkyl groups in these radicals containing 1 to 6 carbon atoms and the alkenyl or alkynyl groups mentioned in these radicals containing 2 to 8 carbon atoms ;
• R 4 is hydrogen or d-Cz-alkyl
• R 3 and R 4 together with the nitrogen atom to which they are attached can also form a five- or six-membered unsaturated ring which can carry one or more substituents R a .
• the invention also relates to processes for the preparation of these compounds, compositions containing them and their use for controlling phytopathogenic harmful fungi.
• 6-Phenyl-7-aminotriazolopyrimidines are generally known from EP-A 71 792 and EP-A 550 113.
• the compounds described in the cited documents are known for combating harmful fungi.
• the present invention is based on the object of providing compounds with improved activity and / or broadened activity spectrum.
• the compounds of the formula I differ from those from the abovementioned publications by the configuration of the alkenyl group in the 7-position of the triazolopyrimidine skeleton which has a branch on the ⁇ -C atom.
• the compounds of the formula I have an increased activity against harmful fungi compared to the known compounds.
• the compounds according to the invention can be obtained in various ways. They are advantageous by reacting dihalotriazolopyrimidines of the formula II in which the shark represents a halogen atom, such as bromine or, in particular chlorine Amines of the formula III obtained under conditions generally known from WO 98/46608.
• reaction of II with amines III is advantageously carried out at 0 ° C to 70 ° C, preferably 10 ° C to 35 ° C, preferably in the presence of an inert solvent such as ether, e.g. B. dioxane, diethyl ether or in particular tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene.
• ether e.g. B. dioxane, diethyl ether or in particular tetrahydrofuran
• halogenated hydrocarbons such as dichloromethane
• aromatic hydrocarbons such as toluene.
• a base such as tertiary amines, for example triethylamine or inorganic bases, such as potassium carbonate, is preferred; Excess amine of formula III can also serve as a base.
• Amines of the formula III are known in some cases or can be prepared by known methods, for example from the corresponding alcohols via the tosylates and phthalimides [cf. J. Am. Chem. Soc, Vol. 117, p. 7025 (1995); WO 93/20804], by reducing the corresponding nitriles [cf. Heterocycles, vol. 35, p. 2 (1993); Synthetic Commun. 25: 413 (1995); Tetrahedron Lett., P. 2933 (1995)], or reductive amination of ketones [cf. J. Am. Chem. Soc, Vol. 122, p. 9556 (2000); Org. Lett. P. 731 (2001); J. Med.
• the reaction temperature is usually from 0 to 120 ° C., preferably from 10 to 40 ° C. [cf. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].
• Suitable solvents include ethers such as dioxane, diethyl ether and, preferably tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene.
• X stands for CC 4 alkyl and M for a metal ion of the valence Y, such as B, Zn or Sn.
• This reaction can be carried out, for example, analogously to the following methods: J. Chem. Soc. Perkin Trans. 1 , 1187 (1994), ibid. 1, 2345 (1996); WO 99/41255; Aust. J. Chem., Vol. 43, S.733 (1990); J. Org. Chem., Vol. 43, S. 358 (1978); J. Chem. Soc. Chem. Commun. S.866 (1979); Tetrahedron Lett., Vol. 34, S.8267 (1993); ibid., Vol. 33, P.413 (1992).
• 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidines VIII are obtained.
• R represents a C r C 4 alkyl group, in particular methyl or ethyl.
• Chlorination or bromination 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.
• the reaction of IX with amines III is advantageously carried out at 0 ° C. to 70 ° C., preferably 10 ° C. to 35 ° C., preferably in the presence of an inert solvent, such as ether, e.g. B. dioxane, diethyl ether or in particular tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene [cf. WO 98/46608].
• ether e.g. B. dioxane, diethyl ether or in particular tetrahydrofuran
• halogenated hydrocarbons such as dichloromethane
• aromatic hydrocarbons such as toluene [cf. WO 98/46608].
• a base such as tertiary amines, for example triethylamine or inorganic bases, such as potassium carbonate, is preferred; Excess amine of formula III can also serve as a base.
• the malonates XI are known in the literature [J. At the. Chem. Soc, Vol. 64, 2714 (1942); J. Org. Chem., Vol. 39, 2172 (1974); Helv. Chim. Acta, Vol. 61, 1565 (1978)] or can be prepared according to the literature cited.
• the subsequent saponification of the ester XII takes place under generally customary conditions, depending on the various structural elements, the alkaline or acid saponification of the compounds XII can be advantageous. Under the conditions of ester hydrolysis, the decarboxylation to I.C can already take place in whole or in part.
• the decarboxylation is usually carried out at from 20 ° C. to 180 ° C., preferably from 50 ° C. to 120 ° C., in an inert solvent, if appropriate in the presence of an acid.
• Suitable acids are hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, p-toluenesulfonic acid.
• Suitable solvents are water, aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.
• the reaction mixtures are usually worked up, for example by mixing with water, separating the phases and, if appropriate, purifying the crude products chromatographically.
• the intermediate and end products are obtained in the form of colorless or slightly brownish, viscous oils, which are freed or purified from volatile components under reduced pressure and at a moderately elevated temperature. If the intermediate and end products are obtained as solids, they can also be purified by recrystallization or digesting. If individual compounds I are not accessible in the ways described above, they can be prepared by derivatizing other compounds I.
• isomer mixtures are obtained in the synthesis, however, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the action of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus to be controlled.
• Halogen fluorine, chlorine, bromine and iodine
• Alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 8 carbon atoms, for example G 1 -C 6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyI, 4-methylpentyl, 1,1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3- Dimethylbutyl, 1-ethylbutyl, 2-ethylbuty
• Haloalkyl straight-chain or branched alkyl groups with 1 to 2, 4 or 6 carbon atoms (as mentioned above), in which case the hydrogen atoms in these groups can be partially or completely replaced by halogen atoms as mentioned above: in particular CC 2 haloalkyl such as chloromethyl, bromomethyl, dichloro - methyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2nd -Chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trich
• Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 4, 6, 8 or 10 carbon atoms and one or two double bonds in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl , 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2 -Pentenyl, 3-pentenyl, 4-pentenyl, 1-Me- thyl-1-butenyl, 2-methyl) -1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl -3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,
• Alkenylene unsaturated, straight-chain hydrocarbon radicals with 3 or 4 carbon atoms and one double bond in any position.
• R 1 is methyl or halomethyl, such as trifluoromethyl.
• Another preferred subject are compounds I in which R 2 is hydrogen.
• Preferred compounds I are those in which R 3 is straight-chain or branched C 2 -C 10 -alkenyl which can be unsubstituted or partially or completely halogenated and / or can carry one to three C-rCa alkoxy groups.
• a particularly preferred object are compounds I in which R 3 represents straight-chain or branched C 2 -C 10 alkenyl which is unsubstituted.
• Equally preferred are compounds I in which R 3 and R 4 together form a C 3 -C 4 alkenylene chain which can be substituted by one or two methyl or halomethyl groups.
• L m is fluorine, chlorine, methyl, C haloalkyl, methoxy, amino, NHR or NR 2 , in which R is methyl or acetyl.
• # is the point of attachment to the triazolopyrimidine backbone
• L 2 , L 4 independently of one another are hydrogen or fluorine
• L 3 is hydrogen, fluorine, chlorine, CH 3 , OCH 3 , amino, NHR or NR 2 ;
• L 5 is hydrogen, chlorine, fluorine or CH 3 .
• the compounds I are suitable as fungicides. They are characterized by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides.
• Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines
• the compounds I are also suitable for combating harmful fungi such as Pacilomyces 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 Pacilomyces 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 compound.
• the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
• amounts of active compound of 0.001 to 0.1 g, preferably 0.01 to 0.05 g, are generally required per kilogram of seed.
• 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 0.005 g to 1 kg, of active ingredient per cubic meter of treated material.
• the compounds I can be converted into the usual formulations, e.g. 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, and in the case of water as 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;
• 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 nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
• Suitable surfactants are alkali metal, alkaline earth metal salts, sulfonic acid ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, 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, octylphenol, nonylphenol, alky
• Mineral oil fractions with a 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 hydrocarbons, for example benzene, toluene, are used to produce directly sprayable solutions, emulsions, pastes or oil dispersions.
• 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 , into consideration.
• Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
• Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
• Solid carriers are e.g. Mineral earths, such as 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, e.g. 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 gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics,
• 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).
• V. 80 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, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel well mixed and ground in a hammer mill (active substance content 80% by weight).
• the active ingredients as such in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or Pouring can be applied.
• the application forms depend entirely on the application purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
• Aqueous application 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.
• concentrates composed of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
• the active ingredient concentrations in the ready-to-use preparations can be varied over a wide range. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
• 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 also 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.
• Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,
• Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidine, guazatine, iminoctadine, spiroxamine, tridemorph, • anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl, Antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,
• Azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propicon
• Dicarboximides such as iprodione, myclozolin, procymidone, vinclozolin,
• Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propineb, Polycarbamat, Thiram, Ziram, Zineb, • Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamidite, dazonometone , Famoxadone, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolan, mepronil, nuarimol, probenazole, proquinazide, pyrifenox, pyroquilone, quinoxyfen, silthiofam, thiabenzazole, thifluzamide, triifizolate, tiifcidilol, thiophanizolate, thiophanizolate, thiophanizolate, thiophanizolate, thiophan
• Nitrophenyl derivatives such as binapacryl, dinocap, dinobutone, nitrophthal-isopropyl,
• phenylpyrroles such as fenpiclonil or fludioxonil, ® sulfur, »other fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chlorothalonil, cyflufenamid, cymoxanil, dazomet, diclome ⁇ in, diclocymet, fenhofen, hexamide, ethabene, edifene Fentin acetate, fenoxanil, ferimzone, fluazinam, fosetyl, fosetyl aluminum, iprovalicarb, hexachlorobenzene, metrafenone, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintozene, zoxamide, or strobilurins such as a ⁇ oxystrobin, fluoxystrobin, fluoxystrobin, dimoxystrobin, .
• Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
• the active ingredients were prepared separately or together as a stock solution with 0.25% by weight of active ingredient in acetone or DMSO. 1% by weight of Uniperol® EL emulsifier (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration.
• Uniperol® EL emulsifier wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
• Leaves of potted plants of the "large meat tomato St. Pierre" were sprayed with an aqueous suspension in the active ingredient concentration given below until they dripped wet. The following day, the leaves were infected with an aqueous spore suspension of Alternaria solani in 2% biomalt solution with a density of 0.17 x 10 6 spores / ml. The plants were then placed in a water vapor-saturated chamber at temperatures between 20 and 22 ° C. After 5 days the leaf infestation on the untreated but infected control plants had developed so strongly that the infestation could be determined visually in%.
• Pepper seedlings of the "Neusiedler Ideal Elite" variety after 4-5 leaves had developed well, were sprayed to runoff point with an aqueous suspension in the active compound concentration given below. The next day, the treated plants were inoculated with a spore suspension of Botrytis cinerea, which contained 1.7 x 10 6 spores / ml in a 2% aqueous biomalt solution. The test plants were then placed in a climatic chamber at 22 to 24 ° C and high air humidity. After 5 days, the extent of the fungal attack on the leaves could be determined visually in%.

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• Organic Chemistry (AREA)
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• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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