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USRE32676E - 7-aminozolo[1,5-a]pyrimidines and fungicides containing these - Google Patents

7-aminozolo[1,5-a]pyrimidines and fungicides containing these Download PDF

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USRE32676E
USRE32676E US07/059,254 US5925487A USRE32676E US RE32676 E USRE32676 E US RE32676E US 5925487 A US5925487 A US 5925487A US RE32676 E USRE32676 E US RE32676E
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alkyl
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Karl Eicken
Hermann Graf
Walter Gramlich
Hubert Sauter
Costin Rentzea
Ernst-Heinrich Pommer
Eberhard Ammermann
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BASF SE
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BASF SE
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles

Definitions

  • the present invention relates to novel 7-aminoazolo[1,5-a]pyrimidines, processes for their preparation and fungicides containing these compounds.
  • R 1 is alkyl which is unsubstituted or substituted by alkoxy or halogen or is aralkyl which is unsubstituted or substituted in the aryl moiety by alkyl, alkoxy or halogen,
  • R 2 and R 3 are each hydrogen or alkyl
  • A is nitrogen or CR 4 , where
  • R 4 is hydrogen, alkyl or halogen, have a good fungicidal action, in particular against phycomycetes.
  • R 1 is, for example, C 4 -C 18 -alkyl, eg. C 4 -C 8 -alkyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, or C 1 -C 18 -alkoxy, or is aralkyl where alkyl is of 1 to 12 carbon atoms, eg. benzyl, p-butylbenzyl or 3-phenylpropyl, which can be substituted in the aryl moiety by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, fluorine, chlorine or bromine.
  • R 2 , R 3 and R 4 are each, for example, hydrogen or C 1 -C 4 -alkyl, eg. methyl, and R 4 may furthermore be, for example, chlorine or bromine.
  • Alkyl, or the alkyl moiety of an alkoxy group is, depending on the stated number of carbon atoms, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl or an isomer of one of these.
  • the ⁇ -keto esters can be prepared as described in Organic Synthesis Coll. Vol. 1, page 248.
  • the reaction of the substituted ⁇ -keto esters of the formula II with the aminoazoles of the formula III can be carried out in the presence or absence of a solvent. It is advantageous to use a solvent which is substantially inert towards the starting materials and in which the latter are partially or completely soluble.
  • Particularly suitable solvents are alcohols, such as ethanol, propanols, butanols, glycols, glycol monoethers or diethylene glycols or their monoethers, amides, such as dimethyl formamide, diethyl formamide, dibutyl formamide or N,N-dimethylacetamide, lower alkanoic acids, such as formic acid, acetic acid or propionic acid, and mixtures of these solvents with water.
  • the reaction temperatures are from 50° to 300° C., preferably from 50° to 150° C., when the reaction is carried out in solution.
  • the condensates of the formula V which are obtained in this manner are precipitated from the reaction solutions in general in pure form, and are washed with the same solvent or with water, dried, and then halogenated with halogenating agents, in particular chlorinating agents, eg. phosphorus chlorides, preferably phosphorus oxytrichloride, at from 50° to 150° C., preferably in excess phosphorus oxytrichloride under reflux. After the excess phosphorus oxytrichloride has been evaporated, the residue is treated with ice water, with or without the addition of a water-immiscible solvent.
  • chlorinating agents eg. phosphorus chlorides, preferably phosphorus oxytrichloride
  • the chlorination product which is isolated from the dry organic phase, if necessary after evaporation of the inert solvent, is generally very pure; it is then reacted with ammonia in an inert solvent at from 100° to 200° C. to give the novel 7-aminoazolo-[1,5-a]pyrimidine.
  • the reaction is preferably carried out under from 1 to 100 bar, using a 1-10 molar excess of ammonia.
  • novel 7-aminoazolo[1,5-a]pyrimidines are isolated as crystalline compounds which are generally very pure, by evaporating the solvent if necessary and then making a paste with water.
  • the reaction can be carried out in the presence or absence of a solvent. It is advantageous to use a solvent which is substantially inert toward the starting materials and in which the latter are partially or completely soluble.
  • a solvent which is substantially inert toward the starting materials and in which the latter are partially or completely soluble.
  • Particularly suitable solvents are alcohols, such as ethanol, propanols, butanols, glycols, glycol monoethers or diethylene glycols or their monoethers, amides, such as dimethylformamide, diethylformamide, dibutylformamide or N,N-dimethylacetamide, lower alkanoic acids, such as formic acid, acetic acid or propionic acid, and mixtures of these solvents with water.
  • the reaction temperatures are from 50° to 300° C., preferably from 50° to 150° C., when the reaction is carried out in solution.
  • novel 7-aminoazolo[1,5-a]pyrimidines are isolated as crystalline compounds, which are generally very pure, if necessary after evaporation of the solvent or dilution with water. Where lower alkanoic acids are used as solvents, it is advantageous to neutralize the remainder of the alkanoic acid by adding an aqueous alkali, if necessary after partial evaporation of the alkanoic acid; the novel 7-aminoazolo[1,5-a]pyrimidines generally crystallize out in very pure form.
  • substituted alkyl cyanides of the formula ##STR8## which are required for the preparation of the 7-aminoazolo[1,5-a]pyrimidines are known; those which are unknown can be prepared by conventional methods, from an alkyl cyanide and a carboxylate with a strong base, eg. an alkali metal hydride, an alkali metal amide or a metalalkyl (J. Amer. Chem. Soc. 73, (1951), 3766).
  • the ether phase is separated off, the aqueous phase is extracted twice with ether, the combined organic phases are dried and evaporated down, and the remaining oil (40 g; 96% crude yield) is distilled under reduced pressure.
  • the fraction passing over at 52° C./0.4 mbar has a purity higher than 98% according to gas chromatography.
  • the novel active ingredients have a strong fungitoxic action on phytopathogenic fungi, especially from the Phycomycetes class.
  • the novel compounds are therefore suitable for instance for combating Phytophthora infestans in tomatoes and potatoes, Phytophthora parasitica in strawberries, Phytophthora cactorum in apples, Pseudoperonospora cubensis in cucumbers, Pseudoperonospora humuli in hops, Peronospora destructor in onions, Peronospora sparsa in roses, Peronospora tabacina in tobacco, Plasmopara viticola in graphes, Plasmopara halstedii in sunflowers, Sclerospora macrospora in Indian corn, Bremia lactucae in lettuce, Mucor mucedo in fruit, Rhizopus nigricans in beets, Erysiphe graminis in cereals, Uncinula necator in grapes, Podo
  • the active ingredients are excellently tolerated by plants. Some of the active ingredients also have curative properties, i.e., the agents may be applied after infection of the plants by the pathogen and success is still ensured.
  • the fungicidal agents contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient.
  • the application rates depend on the type of effect desired, and range from 0.1 to 5 kg of active ingredient per hectare.
  • novel active ingredients may also be mixed and applied with other active ingredients, e.g., herbicides, insecticides, growth regulators, other fungicides and fertilizers.
  • active ingredients e.g., herbicides, insecticides, growth regulators, other fungicides and fertilizers.
  • other active ingredients e.g., herbicides, insecticides, growth regulators, other fungicides and fertilizers.
  • the spectrum of fungicidal action is in many cases increased; with a number of these fungicidal compositions, synergistic effects also occur, i.e., the fungicidal action of the combination product is greater than the effect of the individual components added together.
  • Examples of fungicides which can be combined with the novel compounds are as follows:
  • heterocyclic structures such as
  • novel active ingredients are applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering.
  • the forms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution of the novel active ingredients as possible.
  • emulsions, pastes and oil dispersions to be used direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons carbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, and N-methylpyrrolidone, and water are suitable.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, further coal-tar oils, and oils of vegetable or animal origin
  • Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water.
  • emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers.
  • Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.
  • surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulf
  • Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.
  • Granules e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers.
  • solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.
  • mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomace
  • V. 20 parts by weight of the compound of Example 1 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 17 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in water, a spray liquor is obtained.
  • Leaves of potted vines of the Muller-Thurgau variety were sprayed with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. To assess the duration of action, the plants were set up, after the sprayed-on layer had dried, for 10 days in the greenhouse. Then the leaves were infected with a zoospore suspension of Plasmopara viticola. The plants were first placed for 16 hours in a water vapor-saturated chamber at 24° C. and then in a greenhouse for 8 days at from 20° to 30° C. To accelerate and intensify the sporangiophore discharge, the plants were then again placed in the moist chamber for 16 hours. The extent of fungus attack was then assessed on the undersides of the leaves.
  • Leaves of potted tomatoes of the "Groe Fleischtomate" variety were sprayed with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the leaves were infected with a zoospore suspension of Phytophthora infestans. The plants were then placed for 5 days in a steam-saturated chamber kept at 16° to 18° C. After this period, the disease had spread on the untreated control plants to such an extent that the fungicidal action of the compounds was able to be assessed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

7-Aminoazolo[1,5-a]pyrimidines of the formula <IMAGE> I where R1 is alkyl or aralkyl, R2 and R3 are each hydrogen or alkyl, and A is nitrogen or CR4, where R4 is hydrogen, alkyl or halogen, and fungicides containing these compounds.

Description

The present invention relates to novel 7-aminoazolo[1,5-a]pyrimidines, processes for their preparation and fungicides containing these compounds.
It has been disclosed that 7-aminoazolo[1,5-a]pyrimidines possess pharmacological properties (French Pat. No. 2,448,542, East German Pat. Nos. 99,794 and 55,956, and J. pharm. Soc. Japan 84 (1964), 1113-1118).
We have found that novel 7-aminoazolo[1,5-a]pyrimidines of the formula ##STR2## where
R1 is alkyl which is unsubstituted or substituted by alkoxy or halogen or is aralkyl which is unsubstituted or substituted in the aryl moiety by alkyl, alkoxy or halogen,
R2 and R3 are each hydrogen or alkyl, and
A is nitrogen or CR4, where
R4 is hydrogen, alkyl or halogen, have a good fungicidal action, in particular against phycomycetes.
R1 is, for example, C4 -C18 -alkyl, eg. C4 -C8 -alkyl, which is unsubstituted or substituted by fluorine, chlorine, bromine, or C1 -C18 -alkoxy, or is aralkyl where alkyl is of 1 to 12 carbon atoms, eg. benzyl, p-butylbenzyl or 3-phenylpropyl, which can be substituted in the aryl moiety by C1 -C4 -alkyl, C1 -C4 -alkoxy, fluorine, chlorine or bromine.
R2, R3 and R4 are each, for example, hydrogen or C1 -C4 -alkyl, eg. methyl, and R4 may furthermore be, for example, chlorine or bromine.
Alkyl, or the alkyl moiety of an alkoxy group is, depending on the stated number of carbon atoms, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl or an isomer of one of these.
We have furthermore found that 7-aminoazolo[1,5-a]pyrimidines of the formula I are obtained if a substituted , β-keto ester of the formula II ##STR3## where R1 and R2 have the above meanings and R5 is a lower alkyl radical, is reacted with an aminoazole of the formula III ##STR4## where A, R3 and R4 have the above meanings, to give a condensate of the formula V ##STR5## where R1, R2, R3 and A have the above meanings, this condensate is subjected to a halogenation reaction in which the hydroxyl group is replaced by halogen, and the product is reacted with ammonia.
The β-keto esters can be prepared as described in Organic Synthesis Coll. Vol. 1, page 248.
The reaction of the substituted β-keto esters of the formula II with the aminoazoles of the formula III can be carried out in the presence or absence of a solvent. It is advantageous to use a solvent which is substantially inert towards the starting materials and in which the latter are partially or completely soluble. Particularly suitable solvents are alcohols, such as ethanol, propanols, butanols, glycols, glycol monoethers or diethylene glycols or their monoethers, amides, such as dimethyl formamide, diethyl formamide, dibutyl formamide or N,N-dimethylacetamide, lower alkanoic acids, such as formic acid, acetic acid or propionic acid, and mixtures of these solvents with water. The reaction temperatures are from 50° to 300° C., preferably from 50° to 150° C., when the reaction is carried out in solution.
The condensates of the formula V which are obtained in this manner are precipitated from the reaction solutions in general in pure form, and are washed with the same solvent or with water, dried, and then halogenated with halogenating agents, in particular chlorinating agents, eg. phosphorus chlorides, preferably phosphorus oxytrichloride, at from 50° to 150° C., preferably in excess phosphorus oxytrichloride under reflux. After the excess phosphorus oxytrichloride has been evaporated, the residue is treated with ice water, with or without the addition of a water-immiscible solvent. The chlorination product which is isolated from the dry organic phase, if necessary after evaporation of the inert solvent, is generally very pure; it is then reacted with ammonia in an inert solvent at from 100° to 200° C. to give the novel 7-aminoazolo-[1,5-a]pyrimidine. The reaction is preferably carried out under from 1 to 100 bar, using a 1-10 molar excess of ammonia.
The novel 7-aminoazolo[1,5-a]pyrimidines are isolated as crystalline compounds which are generally very pure, by evaporating the solvent if necessary and then making a paste with water.
We have furthermore found that 7-aminoazolo[1,5-a]pyrimidines of the formula I are obtained if a substituted benzyl cyanide of the formula ##STR6## where R1 and R2 have the above meanings, is reacted with an aminoazole of the formula III ##STR7## where A, R3 and R4 have the above meanings.
The reaction can be carried out in the presence or absence of a solvent. It is advantageous to use a solvent which is substantially inert toward the starting materials and in which the latter are partially or completely soluble. Particularly suitable solvents are alcohols, such as ethanol, propanols, butanols, glycols, glycol monoethers or diethylene glycols or their monoethers, amides, such as dimethylformamide, diethylformamide, dibutylformamide or N,N-dimethylacetamide, lower alkanoic acids, such as formic acid, acetic acid or propionic acid, and mixtures of these solvents with water. The reaction temperatures are from 50° to 300° C., preferably from 50° to 150° C., when the reaction is carried out in solution.
The novel 7-aminoazolo[1,5-a]pyrimidines are isolated as crystalline compounds, which are generally very pure, if necessary after evaporation of the solvent or dilution with water. Where lower alkanoic acids are used as solvents, it is advantageous to neutralize the remainder of the alkanoic acid by adding an aqueous alkali, if necessary after partial evaporation of the alkanoic acid; the novel 7-aminoazolo[1,5-a]pyrimidines generally crystallize out in very pure form.
Some of the substituted alkyl cyanides of the formula ##STR8## which are required for the preparation of the 7-aminoazolo[1,5-a]pyrimidines are known; those which are unknown can be prepared by conventional methods, from an alkyl cyanide and a carboxylate with a strong base, eg. an alkali metal hydride, an alkali metal amide or a metalalkyl (J. Amer. Chem. Soc. 73, (1951), 3766).
General methods of preparation for the substituted alkyl cyanides of the formula VI
1.5 moles of sodium hydride are introduced into 1 liter of toluene, and 1.0 mole of an alkyl cyanide followed by 2.0 moles of a carboxylate are then added dropwise to the stirred mixture, the temperature increasing to 40°-50° C. Stirring is continued for 2 hours at from 75° to 80° C., after which the mixture is cooled and 2 liters of water are added. The aqueous phase is washed twice with 0.2 liters of toluene and acidified with semiconcentrated (about 50% strength by weight) sulfuric acid to pH 2, and the substituted alkyl cyanide of the formula VI is then isolated from the aqueous phase.
EXAMPLES 1. Preparation of 7-amino-2,5-dimethyl-6-n-octylpyrazolo [1,5-a]pyrimidine (Compound 2) (a) 7-hydroxy-2,5-dimethyl-6-n-octylpyrazolo[1,5-a]pyrimidine
200 g of methyl 2-n-octylacetoacetate and 94 g of 3(5)-amino-5(3)-methylpyrazole in 400 ml of n-butanol are refluxed for 5 hours. The mixture is cooled, and the product is filtered off under suction, washed with cold methanol and dried under reduced pressure at 60° C. to give 191 g of 7-hydroxy-2,5-dimethyl-6-n-octylpyrazolo[1,5-a]pyrimidine of melting point 199° C.
(b) 7-chloro-2,5-dimethyl-6-n-octylpyrazolo[1,5-a]-pyrimidine
190 g of the condensate obtained from (a), in 550 ml of phosphorus oxytrichloride, are refluxed for 1.5 hours, after which the excess phosphorus oxytrichloride is evaporated under reduced pressure and the residue is stirred with 500 ml of CH2 Cl2 and 500 ml of ice water. The organic phase is separated off, washed with three times 100 ml of ice water, dried over sodium sulfate and filtered, the solvent is evaporated under reduced pressure, and 179 g of 7-chloro-2,5-dimethyl-6-n-octylpyrazolo-[1,5-a]pyrimidine are isolated as a viscous mass.
(c) 7-amino-2,5-dimethyl-6-n-octylpyrazolo[1,5-a]-pyrimidine
179 g of the chloride obtained in b) and 1300 ml of ethanol are introduced into a 2.5 liter autoclave, 85 g of ammonia are forced in, and the mixture is stirred at 150° C. and under 30 bar for 8 hours. The reacted mixture is concentrated under reduced pressure, the residue is made into a paste with 1000 ml of water, and the product is filtered off under suction and dried under reduced pressure at 70° C. to give 133 g of 7-amino-2,5-dimethyl-6-n-octylpyrazolo-[1,5-a]pyrimidine of melting point 169° C. (Compound 2).
2. Preparation of 7-amino-6-n-butyl-5-methyl-1,2,4-triazolo[1,5-a]pyrimidine (Compound 34) (a) 2-acetyl-n-capronitrile
11.7 g (300 millimoles) of powdered sodium amide are introduced into 500 ml of liquid ammonia at -60° C., and a mixture of 29.1 g (300 millimoles) of n-capronitrile and 26.4 g (300 millimoles) of ethyl acetate is then added slowly. Stirring is continued for 2 hours at -60° C., 200 ml of diethyl ether are added, and the mixture is left overnight to warm up to room temperature, gaseous ammonia escaping. First water and then 50% strength sulfuric acid are added, while cooling with ice, until the pH reaches 5. The ether phase is separated off, the aqueous phase is extracted twice with ether, the combined organic phases are dried and evaporated down, and the remaining oil (40 g; 96% crude yield) is distilled under reduced pressure. The fraction passing over at 52° C./0.4 mbar has a purity higher than 98% according to gas chromatography.
(b) 9.0 g (65 millimoles) of the nitrile from Example 2a and 5.5 g (65 millimoles) of 3-amino-1,2,4-triazole in 200 ml of propionic acid are refluxed for 12 hours, after which the solution is allowed to cool and is then evaporated down to one third of its initial volume. After some time, a precipitate is formed; this is filtered off, washed with a little 2N NaOH and water, and recrystallized from ethanol. Yield: 8.6 g (65%), m.p.: 246° C. (Compound 34).
3. Preparation of 7-amino-6-n-butyl-2-methyl-5-n-propylpyrazolo[1,5-a]pyrimidine (Compound 24) (a) 2-n-butyryl-n-capronitrile
29.1 g (300 millimoles) of n-capronitrile are reacted with 34.8 g (300 millimoles) of ethyl n-butyrate, as described in Example 2a. Crude yield: 98%, yield of pure compound: 50%, bp.: 94°-95° C./0.2 mbar.
(b) 10.1 g (60.5 millimoles) of the nitrile obtained in 3a and 5.80 g (300 millimoles) of 3(5)-amino-5(3)-methylpyrazole are reacted as described in Example 2b. Yield: 5.0 g (34%), mp. (from ethanol): 167° C. (Compound 24).
4. Preparation of 7-amino-5-methyl-6-[3-(n-nonyloxy)propyl]-1,2,4-triazolo[1,5-a]pyrimidine (Compound 44) (a) 2-acetyl-5-(n-nonyloxy)-valeronitrile
35.0 g (156 millimoles) of 5-(n-nonyloxy)-valeronitrile in 500 ml of absolute tetrahydrofuran are initially taken, in the absence of water and under an inert gas atmosphere, and the mixture is cooled to -60° C. 162 millimoles of n-butyl-lithium in n-hexane are slowly added to the stirred mixture, which is then left for 4 hours at -60° C. A solution of 13.1 g (155 millimoles) of dry ethyl acetate in tetrahydrofuran is then added dropwise, stirring is continued for 3 hours at -60° C., and the mixture is allowed to warm up slowly to room temperature. First water and then 2N hydrochloric acid are added while cooling with ice, until the pH of the solution reaches 4. The organic phase which separates out is isolated, washed with water, dried and evaporated down. The oil which remains (41 g; 99%) is more than 90% pure according to gas chromatography, and can be reacted without further purification.
(b) 20.0 g (75 millimoles) of the nitrile from Example 4a are reacted with 6.30 g (75 millimoles) of 3-amino-1,2,4-triazole in 300 ml of boiling propionic acid for 16 hours. The mixture is cooled, the solution is separated off from the precipitate, the filtrate is evaporated down, the residue is taken up in water, the solution is extracted several times with dichloromethane, the combined organic phases are dried and evaporated down, and the oily residue is triturated with diethyl ether to give 9.0 g (36%) of a crystalline compound of melting point 167° C. (Compound 44).
5. Preparation of 7-amino-5-methyl-6-[3-(neopentyloxy)-propyl] 1,2,4-triazolo[1,5-a]pyrimidine (Compound 38) (a) 7-hydroxy-5-methyl-6-[3-(neopentyloxy)-propyl]-1,2,4-triazolo[1,5-a]pyrimidine
22.0 g (90 millimoles) of methyl 2-[3-(neopentyloxy)-propyl]-acetoacetate and 7.14 g (84.9 millimoles) of 3-amino-1,2,4-triazole in 300 ml of boiling propionic acid are allowed to react for 21 hours. The mixture is cooled and then evaporated down, the residue is stirred into ice water, the solution is neutralized with 2N NaOH, and the product is filtered off under suction to give 13.5 g (57%) of colorless crystals of melting point 155°-159° C., which are reacted without further purification.
(b) 7-chloro-5-methyl-6-[3-(neopentyloxy)-propyl]-1,2,4-triazolo[1,5-a]pyrimidine
11.5 g (41.4 millimoles) of the product from 5a, in 330 ml of phosphorus oxytrichloride, are refluxed for 8 hours, after which volatile components are distilled off, the oily residue which remains is taken up in dichloromethane, and the solution is washed with saturated sodium bicarbonate solution, dried and evaporated down to give 10 g (82%) of a yellowish oil which is pure according to thin layer chromatography.
(c) 10.0 g (33.7 millimoles) of the product from 5b are dissolved in 100 ml of dioxane, and then reacted with 6.3 g (370 millimoles) of ammonia in an autoclave at 130° C. for 60 hours. After the mixture has been cooled and the pressure let down, the resulting precipitate is filtered off under suction and taken up in dichloromethane, and the solution is washed three times with water, dried and evaporated down to give 5.5 g (58%) of a colorless powder (compound 38) of melting point 202° C. A further 2.5 g of product can be obtained by evaporating down the filtrate from the dioxane solution.
For example, the following 7-aminoazolo[1,5-a]pyrimidines can be prepared by the methods described above:
__________________________________________________________________________
 ##STR9##                                                                 
No.                                                                       
   R.sup.1                  R.sup.2                                       
                                R.sup.3                                   
                                    R.sup.4                               
                                      A  M.p. (°C.)                
__________________________________________________________________________
1  n-C.sub.4 H.sub.9        CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         186                              
2  n-C.sub.8 H.sub.17       CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         169                              
3  n-C.sub.4 H.sub.9CH(C.sub.2 H.sub.5)CH.sub.2                           
                            CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         159                              
4  n-C.sub.8 H.sub.17       CH.sub.3                                      
                                H   --                                    
                                      N  217                              
5  n-C.sub.4 H.sub.9CH(C.sub.2 H.sub.5)CH.sub.2                           
                            CH.sub.3                                      
                                H   --                                    
                                      N  228                              
6  C.sub.6 H.sub.5CH.sub.2  CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         235                              
7  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2                             
                            CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         214                              
8  4-t-C.sub.4 H.sub.9 C.sub.6 H.sub.4CH.sub.2                            
                            CH.sub.3                                      
                                H   --                                    
                                      N  >280                             
9  C.sub.6 H.sub.5(CH.sub.2).sub.3                                        
                            CH.sub.3                                      
                                H   --                                    
                                      N  244                              
10 n-C.sub.5 H.sub.11       CH.sub.3                                      
                                H   --                                    
                                      N  251                              
11 n-C.sub.6 H.sub.13       CH.sub.3                                      
                                H   --                                    
                                      N  237                              
12 n-C.sub.7 H.sub.15       CH.sub.3                                      
                                H   --                                    
                                      N  209                              
13 n-C.sub.5 H.sub.11       CH.sub.3                                      
                                CH.sub.3                                  
                                    --                                    
                                      N  193                              
14 n-C.sub.6 H.sub.13       CH.sub.3                                      
                                CH.sub.3                                  
                                    --                                    
                                      N  200                              
15 n-C.sub.8 H.sub.17       CH.sub.3                                      
                                CH.sub.3                                  
                                    --                                    
                                      N  198                              
16 n-C.sub.4 H.sub.9        n-C.sub.4 H.sub.9                             
                                H   --                                    
                                      N  187                              
17 n-C.sub.4 H.sub.9        n-C.sub.4 H.sub.9                             
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         145                              
18                                                                        
    ##STR10##               CH.sub.3                                      
                                H   --                                    
                                      N  209                              
19                                                                        
    ##STR11##               CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         176                              
20 (H.sub.5 C.sub.2).sub.2CHCH.sub.2                                      
                            CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         178                              
21 n-C.sub.10 H.sub.21      n-C.sub.3 H.sub.7                             
                                H   --                                    
                                      N  152                              
22 n-C.sub.10 H.sub.21      n-C.sub.3 H.sub.7                             
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         114                              
23 NC.sub.10 H.sub.21       n-C.sub.4 H.sub.9                             
                                H   --                                    
                                      N  151                              
24 n-C.sub.5 H.sub.9        n-C.sub.3 H.sub.7                             
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         167                              
25 n-C.sub.4 H.sub.9        n-C.sub.3 H.sub.7                             
                                H   --                                    
                                      N  186                              
26 n-C.sub.12 H.sub.25      CH.sub.3                                      
                                CH.sub.3                                  
                                    --                                    
                                      CR.sup.4                            
                                         127                              
27 n-C.sub.12 H.sub.25      CH.sub.3                                      
                                H   --                                    
                                      N  209                              
28 n-C.sub.10 H.sub.21      CH.sub.3                                      
                                H   --                                    
                                      N  207                              
29 n-C.sub.9 H.sub.19       CH.sub.3                                      
                                H   --                                    
                                      N  215                              
30 n-C.sub.6 H.sub.13       CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         177                              
31 n-C.sub.9 H.sub.19       CH.sub.3                                      
                                CH.sub.3                                  
                                    --                                    
                                      N  159                              
32 n-C.sub.10 H.sub.21      CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         146                              
33 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4CH.sub.2CH(CH.sub.3)                 
                            CH.sub.3                                      
                                H   --                                    
                                      N  256                              
34 n-C.sub.4 H.sub.9        CH.sub.3                                      
                                H   --                                    
                                      N  246                              
35 (n-C.sub.3 H.sub.7 )(C.sub.2 H.sub.5)CHCH.sub.2O(CH.sub.2).sub.3       
                            CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         108                              
36 (n-C.sub.3 H.sub.7)(C.sub.2 H.sub.5)CHCH.sub.2O(CH.sub.2).sub.3        
                            CH.sub.3                                      
                                H   --                                    
                                      N  149                              
37 t-C.sub.4 H.sub.9 CH.sub.2O(CH.sub.2).sub.3                            
                            CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         134                              
38 t-C.sub.4 H.sub.9CH.sub.2O(CH.sub.2).sub.3                             
                            CH.sub.3                                      
                                H   --                                    
                                      N  202                              
39 t-C.sub.4 H.sub.9O(CH.sub.2).sub.4                                     
                            CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         61  (decomposes)                 
40 (t-C.sub.4 H.sub.9CH.sub.2)(CH.sub.3)CH(CH.sub.2).sub.2O(CH.sub.2).sub.
   5                        CH.sub.3                                      
                                H   --                                    
                                      N  161                              
41 (i-C.sub.4 H.sub.9)(C.sub.2 H.sub.5)CHO(CH.sub.2).sub.3                
                            CH.sub.3                                      
                                H   --                                    
                                      N  156                              
42 n-C.sub.8 H.sub.17O(CH.sub.2).sub.3                                    
                            n-C.sub.3 H.sub.7                             
                                H   --                                    
                                      N  97                               
43 i-C.sub.3 H.sub.7(CH.sub.2).sub.3CH(CH.sub.3)(CH.sub.2).sub.2O(CH.sub.2
   ).sub.3                  CH.sub.3                                      
                                H   --                                    
                                      N  156                              
44 n-C.sub.9 H.sub.19O (CH.sub.2).sub.3                                   
                            CH.sub.3                                      
                                H   --                                    
                                      N  167                              
45 n-C.sub.4 H.sub.9O(CH.sub.2).sub.3                                     
                            CH.sub.3                                      
                                H   --                                    
                                      N  180                              
46 n-C.sub.6 H.sub.13O(CH.sub.2).sub.3                                    
                            CH.sub.3                                      
                                H   --                                    
                                      N  176                              
47 n-C.sub.9 H.sub.19O(CH.sub.2).sub.3                                    
                            CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         94                               
48 n-C.sub.6 H.sub.13O(CH.sub.2).sub.3                                    
                            n-C.sub.3 H.sub.7                             
                                H   --                                    
                                      N  109                              
49 (n-C.sub.4 H.sub.9)(C.sub.2 H.sub.5)CHCH.sub.2O(CH.sub.2).sub.5        
                            CH.sub.3                                      
                                H   --                                    
                                      N  resin                            
50 t-C.sub.4 H.sub.9CH.sub.2CH(CH.sub.3)(CH.sub.2).sub.2O(CH.sub.2).sub.3 
                            CH.sub.3                                      
                                H   --                                    
                                      N  154                              
51 n-C.sub.4 H.sub.9O(CH.sub.2).sub.3                                     
                            CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         145                              
52 t-C.sub.4 H.sub.9CH.sub.2CH(CH.sub.3)(CH.sub.2).sub.2O(CH.sub.2).sub.3 
                            CH.sub.3                                      
                                CH.sub.3                                  
                                    H CR.sup.4                            
                                         122                              
__________________________________________________________________________
The novel active ingredients have a strong fungitoxic action on phytopathogenic fungi, especially from the Phycomycetes class. The novel compounds are therefore suitable for instance for combating Phytophthora infestans in tomatoes and potatoes, Phytophthora parasitica in strawberries, Phytophthora cactorum in apples, Pseudoperonospora cubensis in cucumbers, Pseudoperonospora humuli in hops, Peronospora destructor in onions, Peronospora sparsa in roses, Peronospora tabacina in tobacco, Plasmopara viticola in graphes, Plasmopara halstedii in sunflowers, Sclerospora macrospora in Indian corn, Bremia lactucae in lettuce, Mucor mucedo in fruit, Rhizopus nigricans in beets, Erysiphe graminis in cereals, Uncinula necator in grapes, Podosphaera leucotricha in apples, Sphaerotheca fuliginea in roses, and Erysiphe cichoriacearum in cucumbers.
The active ingredients are excellently tolerated by plants. Some of the active ingredients also have curative properties, i.e., the agents may be applied after infection of the plants by the pathogen and success is still ensured.
The fungicidal agents contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient. The application rates depend on the type of effect desired, and range from 0.1 to 5 kg of active ingredient per hectare.
The novel active ingredients may also be mixed and applied with other active ingredients, e.g., herbicides, insecticides, growth regulators, other fungicides and fertilizers. When mixed with other fungicides, the spectrum of fungicidal action is in many cases increased; with a number of these fungicidal compositions, synergistic effects also occur, i.e., the fungicidal action of the combination product is greater than the effect of the individual components added together. Examples of fungicides which can be combined with the novel compounds are as follows:
sulfur
dithiocarbamates and derivatives thereof, such as
ferric dimethyldithiocarbamate
zinc dimethyldithiocarbamate
zinc ethylenebisthiocarbamate
tetramethylthiuram disulfide
manganese-zinc ethylenediamine-bisdithiocarbamate
ammonia complex of zinc-(N,N'-ethylene)-bisdithiocarbamate
and
N,N'-polyethylene-bis-(thiocarbamoyl)-disulfide
ammonia complex of zinc-(N,N'-propylene-bisdithiocarbamate)
and
N,N'-polypropylene-bis-(thiocarbamoyl)-disulfide
nitro derivatives, such as
dinitro-(1-methylheptyl)-phenylcrotonate
2-sec-butyl-4,6-dinitrophenyl-3,5-dimethylacrylate
2-sec-butyl-4,6-dinitrophenylisopropylcarbonate
diisopropyl 5-nitroisophthalate
heterocyclic structures, such as
2-heptadecyl-2-imidazoline acetate
2,4-dichloro-6-(o-chloroanilino)-s-triazine
0,0-diethylphthalimidophosphorothionate
5-amino-1-[bis-(dimethylamino)-phosphynyl]-3-phenyl-1,2,4-triazole
2,3-dicyano-1,4-dithiaanthraquinone
2-thio-1,3-dithio-(4,5-b)-quinoxaline
methyl 1-(butylcarbamoyl)-2-benzimidazole carbamate
2-methoxycarbonylaminobenzimidazole
2-[furyl-(2)]-benzimidazole
2-[thiazolyl-(4)]-benzimidazole
N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide
N-trichloromethylthiotetrahydrophthalimide
N-trichloromethylphthalimide
N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfuric acid diamide
5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole
2-thiocyanomethylthiobenzthiazole
1,4-dichloro-2,5-dimethoxybenzene
4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone
pyridine-2-thio-1-oxide
8-hydroxyquinoline and its copper salt
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin
2-methyl-5,6-dihydro-4-H-pyran-3-carboxanilide
2-methyl-furan-3-carboxanilide
2,5-dimethyl-furan-3-carboxanilide
2,4,5-trimethyl-furan-3-carboxanilide
2,5-dimethyl-furan-3-carboxylic acid cyclohexylamide
N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxamide
2-methyl-benzoic acid anilide
2-iodobenzoic anilide
N-formyl-N-morpholine-2,2,2-trichloroethylacetal
piperazine-1,4-diylbis-(1-(2,2,2-trichloroethyl)-formamide
1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichlorethane
2,6-dimethyl-N-tridecyl-morpholine and its salts
2,6-dimethyl-N-cyclododecyl-morpholine and its salts
N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine
N-[3-(p-tert.-butylphenyl)-2-methylpropyl]-piperidine
1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-ethyl]-1-H-1,2,4-triazole -1,2,4-triazole
-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-yl-ethyl]-1-H-1,2,4-triazole
N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazol-ylurea
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol
alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethanol
5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine
bis-(p-chlorophenyl)-3-pyridinemethanol
1,2-bis-(3-ethoxycarbonyl-2-thioureido)-benzene
1,2-bis-(3-methoxycarbonyl)-2-thioureido)-benzene
2-cyano-N-(ethylaminocarbonyl)-2-(methoximino)acetamide
and various fungicides, such as
dodecylguanidine acetate
3-[2-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide
hexachlorobenzene
D,L-methyl-N-(2,6-dimethylphenyl)-N-(2-furoyl)-alanate
methyl D,L-N-(2,6-dimethylphenyl)-N-(2-methoxyacetyl)-alanate
N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone
methyl DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)-alanate 5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine
3-(3,5-dichlorophenyl)-5-methyl-5-methoxymethyl-1,3-oxazolidine2,4-dione
3-(3,5-dichlorophenyl)-1-isopropyl-carbamoylhydantoin
N-(3,5-dichlorophenyl)-1,2-dimethyl-cyclopropane-1,2-dicarboximide.
The novel active ingredients are applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution of the novel active ingredients as possible.
For the preparation of solutions, emulsions, pastes and oil dispersions to be used direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons carbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, and N-methylpyrrolidone, and water are suitable.
Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.
Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.
Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.
Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.
Examples of such formulations follow.
I. 90 parts by weight of the compound of Example 1 is mixed with 10 parts by weight of N-methyl-alphapyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.
II. 20 parts by weight of the compound of Example 2 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.
III. 20 parts by weight of the compound of Example 1 is dissolved in a mixture consisting of 30 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and finely distributing it therein, an aqueous dispersion is obtained.
IV. 20 parts by weight of the compound of Example 2 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.
V. 20 parts by weight of the compound of Example 1 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 17 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in water, a spray liquor is obtained.
VI. 5 parts by weight of the compound of Example 2 is intimately mixed with 95 parts by weight of particulate kaolin. A dust is obtained containing 5% by weight of the active ingredient.
VII. 30 parts by weight of the compound of Example 1 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.
VIII. 40 parts by weight of the compound of Example 2 is intimately mixed with 30 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water to give a stable aqueous dispersion.
IX. 20 parts of the compound of Example 1 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.
The following experiments demonstrate the biological action of the novel compounds.
EXAMPLE 1 Action on Plasmopara viticola
Leaves of potted vines of the Muller-Thurgau variety were sprayed with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. To assess the duration of action, the plants were set up, after the sprayed-on layer had dried, for 10 days in the greenhouse. Then the leaves were infected with a zoospore suspension of Plasmopara viticola. The plants were first placed for 16 hours in a water vapor-saturated chamber at 24° C. and then in a greenhouse for 8 days at from 20° to 30° C. To accelerate and intensify the sporangiophore discharge, the plants were then again placed in the moist chamber for 16 hours. The extent of fungus attack was then assessed on the undersides of the leaves.
The results of the experiment show that for instance compounds nos. 1, 2, 3, 4, 5, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 25, 26, 28, 29, 30, 31 and 32, applied as 0.05 and 0.025% spray liquors, had a better fungicidal action (e.g., 97%) than the prior art active ingredients 7-amino-6-phenyl-(1,2,4-triazolo)-[1,5-a]pyrimidine (A) and 7-amino-2-methyl-6-phenyl-pyrazolo-[1,5-a]pyrimidine (B) (e.g., 30%).
EXAMPLE 2 Action of Phytophthora infestans in tomatoes
Leaves of potted tomatoes of the "Groe Fleischtomate" variety were sprayed with aqueous liquors containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the leaves were infected with a zoospore suspension of Phytophthora infestans. The plants were then placed for 5 days in a steam-saturated chamber kept at 16° to 18° C. After this period, the disease had spread on the untreated control plants to such an extent that the fungicidal action of the compounds was able to be assessed.
The results of this experiment show that for example compounds nos. 4, 5, 10, 11, 13, 14, 15, 16, 18, 19, 20, 21, 25, 29, 33, 36, 40, 41, 48 and 49, applied as 0.025% spray liquors, had a better fungicidal action (e.g., 90%) than the prior art active ingredients A and N-trichloromethylthio-tetrahydrophthalimide (e.g., 60%).

Claims (7)

We claim:
1. ##STR12## where R1 is a .[.C6 -C18 -alkyl.]. .Iadd.C7 -C18 -alkyl .Iaddend.which is unsubstituted or a C3 -C18 alkyl which is mono substituted by a C1 -C18 -alkoxy or halogen and
R2 and R3 are each hydrogen or a C1 -C4 -alkyl, and
A is nitrogen or CR4, where
R4 is hydrogen, a C1 -C4 alkyl or halogen.
2. A process for combatting fungi, wherein the fungi or the materials, plants, soils or seeds to be protected against fungus attack are treated with a fungicidally effective amount of an aminoazolopyrimidine of the formula ##STR13## where R1 is a C4 -C18 -alkyl which is unsubstituted or mono substituted by a C1 -C18 -alkoxy or halogen or is aralkyl where the alkyl is of 1-12 carbons which is unsubstituted or substituted in the aryl moiety by C1 -C4 -alkyl, C1 -C4 -alkoxy or halogen,
R2 and R3 are each hydrogen or a C1 -C4 -alkyl, and
A is nitrogen or CR4, where
R4 is hydrogen, a C1 -C4 -alkyl or halogen.
3. The compound of claim 1 wherein R1 is n-C8 H17, R2 is CH3, R3 is CH3, R4 is H and A is CR4.
4. The compound of claim 1 wherein R1 is n-C8 H17, R2 is CH3, R3 is H and A is N.
5. The compound of claim 1 wherein R1 is n-C9 H19, R2 is CH3, R3 is H and A is N.
6. The compound of claim 1 wherein R1 is n-C9 H19, R2 is CH3, R3 is CH3 and A is N.
7. The compound of claim 1 wherein R1 is an unsubstituted alkyl of 7 to 10 carbon atoms.
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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5612345A (en) * 1993-03-04 1997-03-18 Shell Internationale Research Maatschappij B.V. Dihalotriazolopyrimidine derivatives as fungicides
US20070173408A1 (en) * 2004-03-10 2007-07-26 Blasco Jordi T I 5,6-Dialkyl-7-aminotriazolopyrimidines, their preparation and their use for controlling harmful fungi, and compositions comprising these compounds
US20080125445A1 (en) * 2005-03-01 2008-05-29 Basf Aktiengesellschaft 5,6-Dialkyl-7-Amino-Azolopyrimidines, Method For Their Production, Their Use For Controlling Pathogenic Fungi and Agents Containing Said Compounds
US20080139581A1 (en) * 2005-03-02 2008-06-12 Basf Aktiengesellschaft 2-Substituted 7-Aminoazolopyrimidines, Processes For Their Preparation And Their Use For Controlling Harmful Fungi, And Compositions Comprising These Compounds
US20080146839A1 (en) * 2005-03-18 2008-06-19 Basf Aktiengesellschaft Method for Producing 5-Halo-2,4,6-Trifluoroisophthalic Acid
US20080176744A1 (en) * 2005-03-10 2008-07-24 Basf Aktiengesellschaft Use of 4-Aminopyrimidines for Controlling Harmful Fungi, Novel 4-Aminopyrimidines, Processes for Their Preparation and Compositions Comprising Them
US20080188493A1 (en) * 2005-03-01 2008-08-07 Basf Aktiengesellschaft 5,6-Dialkyl-7-Aminoazolopyrimidines, Their Preparation and Their Use For Controlling Harmful Fungi, and Compositions Comprising These Compounds
US20080207455A1 (en) * 2005-03-01 2008-08-28 Basf Aktingesellschaft 5,6-Dialkyl-7-Aminoazolopyrimidines, Their Preparation and Their Use for Controlling Harmful Fungi, and Compositions Comprising These Compounds
US20080221130A1 (en) * 2005-07-27 2008-09-11 Basf Aktiengesellschaft Fungicidal 5-Methyl-6-Phenylpyrazolopyrimidin-7-Ylamines
US20080262000A1 (en) * 2005-02-16 2008-10-23 Basf Aktiengesellschaft 5-Alkoxyalkyl-6-alkyl-7-Aminoazolopyrimidines, Process for Their Preparation, Their Use for Controlling Harmful Fungi, and Compositions Comprising Them
US20080312078A1 (en) * 2005-07-27 2008-12-18 Basf Aktiengesellschaft 6-Phenyl-Pyrazolopyrimidine-7-Ylamine Fungicides
US20090156398A1 (en) * 2005-07-27 2009-06-18 Basf Aktiengesellschaft Fungicidal 5-alkyl-6-phenylpyrazolopyrimidin-7-ylamines
US20100087640A1 (en) * 2007-01-11 2010-04-08 Basf Se Method for production of aryl-substituted annelated pyrimidines
US20100105903A1 (en) * 2007-03-02 2010-04-29 Basf Se Method for the production of beta-ketonitriles
US20130252951A1 (en) * 2010-09-27 2013-09-26 Proximagen Limited 7-hydroxy-pyrazolo[1,5-a] pyrimidine compounds and their use as ccr2 receptor antagonists
US9288996B2 (en) 2010-03-18 2016-03-22 Basf Se Fungicidal compositions comprising a phosphate solubilizing microorganism and a fungicidally active compound
CN111683951A (en) * 2018-02-02 2020-09-18 勃林格殷格翰国际有限公司 Triazolopyrimidine derivatives useful as ghrelin O-acyltransferase (GOAT) inhibitors

Families Citing this family (416)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3533050A1 (en) * 1985-09-17 1987-03-26 Basf Ag 7-AMINO-AZOLO (1,5-A) PYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM, OR THEIR USE AS FUNGICIDES
DE3702322A1 (en) * 1987-01-27 1988-08-04 Hydrierwerk Rodleben Veb METHOD AND DEVICE FOR PRODUCING 5-METHYL-7-DIETHYLAMINO-S-TRIAZOLO (1,5-A) PYRIMIDINE
US4988812A (en) * 1989-11-06 1991-01-29 Dow Elanco Aqueous process for the preparation of 5-methyl-n-(aryl)-1,2,4-triazolo(1,5-A)pyrimidine-2-sulfonamides
US5478825A (en) * 1991-02-22 1995-12-26 Egis Gyogyszergyar 5-(substituted amino)-1,2,4-triazolo (1,5-A) pyrimidine derivatives
ATE174917T1 (en) * 1991-04-22 1999-01-15 Otsuka Pharma Co Ltd PYRAZOLO(1,5-A>PYRIMIDINE DERIVATIVES AND ANTI-INFLAMMATORY AGENTS CONTAINING SAME
US5593996A (en) * 1991-12-30 1997-01-14 American Cyanamid Company Triazolopyrimidine derivatives
IL108731A (en) * 1993-03-04 1997-03-18 Shell Int Research 6, N-DISUBSTITUTED-£1, 2, 4| TRIAZOLO-£1, 5-a| PYRIMIDINE- 7-AMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS FUNGICIDES
UA76486C2 (en) * 2001-07-26 2006-08-15 Basf Ag 7-amino triazolopyrimidines, a process of praparation, a fungicidal preparations based thereon and a method to control phytopathogenic fungi
CA2504192A1 (en) 2002-11-07 2004-05-21 Basf Aktiengesellschaft 5-alkyl-7-aminotriazolopyrimidines, methods and intermediary products necessary for the production thereof, agents containing said compounds and the use thereof for fighting against harmful mushrooms
EP1644003A1 (en) * 2003-06-04 2006-04-12 Vernalis (Cambridge) Limited Triazolo ´1,5-a!pyrimidines and their use in medicine
DE10357569A1 (en) * 2003-12-10 2005-07-07 Bayer Cropscience Ag pyrazolopyrimidine
DE102004008807A1 (en) 2004-02-20 2005-09-08 Bayer Cropscience Ag pyrazolopyrimidine
DE502005009861D1 (en) * 2004-03-10 2010-08-19 Basf Se 5,6-DIALKYL-7-AMINO-TRIAZOLOPYRIMIDINE, PROCESS FOR THE PRODUCTION THEREOF, AND ITS USE FOR CONTROLLING HARMFUL MUSHROOMS AND THE MEDIUM CONTAINING THE SAME
WO2005087771A2 (en) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
AU2005221805A1 (en) * 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dihydrocarbyl-7-amino-triazolopyrimidines, method for their production, their use for controlling pathogenic fungi and agents containing said compounds
PE20060020A1 (en) * 2004-03-30 2006-03-10 Basf Ag 5-6-CYCLOALKYL-7-AMINO-TRIAZOLOPYRIMIDINES TO COMBAT PHYTOPATOGENIC FUNGI AND PROCEDURES FOR THEIR OBTAINMENT
US20050265957A1 (en) * 2004-04-08 2005-12-01 Monahan Sean D Polymerized formamides for use in delivery of compounds to cells
BRPI0607502A2 (en) * 2005-03-01 2016-11-01 Basf Ag process compounds for the preparation thereof, agent, seed, and process for combating phytopathogenic harmful fungi
WO2006114405A2 (en) * 2005-04-25 2006-11-02 Basf Aktiengesellschaft Use of 5-alkyl-6-phenylalkyl-7-amino-azolopyrimidines, novel azolopyrimidines, methods for the production thereof, and agents containing the same
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BRPI1009642A2 (en) 2009-06-18 2015-08-18 Basf Se "triazole compounds of formulas ie ii, compounds of formula iv, agricultural composition, use of a compound of formula i, ii and / or iv, method for controlling harmful fungi, seed, pharmaceutical composition and method for treating cancer or viral infections, or to combat zoopathogenic or humanopathogenic fungi "
WO2010146116A1 (en) 2009-06-18 2010-12-23 Basf Se Triazole compounds carrying a sulfur substituent
EP2443098A1 (en) 2009-06-18 2012-04-25 Basf Se Antifungal 1, 2, 4-triazolyl derivatives
WO2010149758A1 (en) 2009-06-25 2010-12-29 Basf Se Antifungal 1, 2, 4-triazolyl derivatives
WO2011006886A2 (en) 2009-07-14 2011-01-20 Basf Se Azole compounds carrying a sulfur substituent xiv
EP2458981A2 (en) 2009-07-28 2012-06-06 Basf Se Pesticidal suspo-emulsion compositions
WO2011026796A1 (en) 2009-09-01 2011-03-10 Basf Se Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi
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EP2402344A1 (en) 2010-06-29 2012-01-04 Basf Se Pyrazole fused bicyclic compounds
EP2402343A1 (en) 2010-06-29 2012-01-04 Basf Se Pyrazole-fused bicyclic compounds
EP2402337A1 (en) 2010-06-29 2012-01-04 Basf Se Pyrazolopyridine compounds
EP2402338A1 (en) 2010-06-29 2012-01-04 Basf Se Pyrazolopyridine compounds
EP2402335A1 (en) 2010-06-29 2012-01-04 Basf Se Pyrazolopyridine compounds
EP2402336A1 (en) 2010-06-29 2012-01-04 Basf Se Pyrazolopyridine compounds
EP2402345A1 (en) 2010-06-29 2012-01-04 Basf Se Pyrazole fused bicyclic compounds
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EP2402340A1 (en) 2010-06-29 2012-01-04 Basf Se Pyrazolopyridine compounds
EP2402339A1 (en) 2010-06-29 2012-01-04 Basf Se Pyrazolopyridine compounds
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EP2447261A1 (en) 2010-10-29 2012-05-02 Basf Se Pyrrole, furane and thiophene derivatives and their use as fungicides
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MX2013006737A (en) 2010-12-20 2013-07-15 Basf Se Pesticidal active mixtures comprising pyrazole compounds.
EP2481284A3 (en) 2011-01-27 2012-10-17 Basf Se Pesticidal mixtures
EP2688405B1 (en) 2011-03-23 2017-11-22 Basf Se Compositions containing polymeric, ionic compounds comprising imidazolium groups
BR112013026433A2 (en) 2011-04-15 2018-06-26 Basf Se use of compounds, method of combating harmful fungi, seed coated with at least one compound, compound and agrochemical composition
US9137997B2 (en) 2011-04-15 2015-09-22 Basf Se Use of substituted dithiine-dicarboximides for combating phytopathogenic fungi
EP2699090A1 (en) 2011-04-21 2014-02-26 Basf Se 3,4-disubstituted pyrrole 2,5-diones and their use as fungicides
CN103607890A (en) 2011-06-17 2014-02-26 巴斯夫欧洲公司 Compositions comprising fungicidal substituted dithiines and further actives
BR112014000625B1 (en) 2011-07-13 2019-03-19 BASF Agro B.V. COMPOUNDS, PROCESSES FOR PREPARING COMPOUNDS, AGRICULTURAL COMPOSITIONS, USES OF COMPOUNDS AND METHOD FOR COMBATING PHYTOPATHOGENIC FUNGI
WO2013010885A1 (en) 2011-07-15 2013-01-24 Basf Se Fungicidal alkyl- and aryl-substituted 2-[2-chloro-4-(dihalo-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
BR112014000821A2 (en) 2011-07-15 2016-08-23 Basf Se compounds, process, agrochemical compositions, use of compounds of formula I, method for combating harmful fungi and seed
PH12014500081A1 (en) 2011-07-15 2019-07-03 Basf Se Fungicidal alkyl-substituted 2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
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JP2014525407A (en) 2011-08-15 2014-09-29 ビーエーエスエフ ソシエタス・ヨーロピア Bactericidal substituted 1- {2- [2-halo-4- (4-halogen-phenoxy) -phenyl] -2-alkoxy-2-alkynyl / alkenyl-ethyl} -1H- [1,2,4] triazole compounds
EP2559688A1 (en) 2011-08-15 2013-02-20 Basf Se Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-butoxy-ethyl}-1h [1,2,4]triazole compounds
CN103717579B (en) 2011-08-15 2016-10-12 巴斯夫欧洲公司 Fungicidal substituted 1-{2-[2-halo-4-(4-halophenoxy)phenyl]-2-alkoxy-2-cyclylethyl}-1H-[1, 2,4] Triazole Compounds
BR112014002922A2 (en) 2011-08-15 2017-02-21 Basf Se compounds of formula i, process of preparing compounds of formula i, compounds of formula xii, viii and xi, agrochemical compositions, use and seed
AU2012296885A1 (en) 2011-08-15 2014-03-06 Basf Se Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl-2-alkynyloxy-ethyl}-1H-[1,2,4]triazole compounds
WO2013024082A1 (en) 2011-08-15 2013-02-21 Basf Se Fungicidal substituted 1-{2-cyclyloxy-2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-ethyl}-1h-[1,2,4]triazole compounds
AR087535A1 (en) 2011-08-15 2014-04-03 Basf Se FUNGICIDE COMPOUNDS OF 1- {2- [2-HALO-4- (4-HALOGEN-Phenoxy) -Phenyl] -2-ETOXI-ETIL} -1H- [1,2,4] SUBSTITUTED TRIAZOL
US20140200136A1 (en) 2011-09-02 2014-07-17 Basf Se Agricultural mixtures comprising arylquinazolinone compounds
TWI582095B (en) 2011-11-11 2017-05-11 基利阿波羅有限責任公司 ACC inhibitors and their use
PE20141431A1 (en) 2011-12-21 2014-10-29 Basf Se USE OF STROBILURIN-TYPE COMPOUNDS TO COMBAT PHYTOPATHOGENIC FUNGI RESISTANT TO Qo INHIBITORS
WO2013113719A1 (en) 2012-02-03 2013-08-08 Basf Se Fungicidal pyrimidine compounds ii
AU2013214353A1 (en) 2012-02-03 2014-08-21 Basf Se Fungicidal pyrimidine compounds
WO2013113791A1 (en) 2012-02-03 2013-08-08 Basf Se Fungicidal pyrimidine compounds
WO2013113716A1 (en) 2012-02-03 2013-08-08 Basf Se Fungicidal pyrimidine compounds
WO2013113778A1 (en) 2012-02-03 2013-08-08 Basf Se Fungicidal pyrimidine compounds
WO2013113781A1 (en) 2012-02-03 2013-08-08 Basf Se Fungicidal pyrimidine compounds i
WO2013113782A1 (en) 2012-02-03 2013-08-08 Basf Se Fungicidal pyrimidine compounds
WO2013113720A1 (en) 2012-02-03 2013-08-08 Basf Se Fungicidal pyrimidine compounds
WO2013113776A1 (en) 2012-02-03 2013-08-08 Basf Se Fungicidal pyrimidine compounds
EA201491472A1 (en) 2012-02-03 2015-01-30 Басф Се FUNGICIDE PYRIMIDINE COMPOUNDS
WO2013113773A1 (en) 2012-02-03 2013-08-08 Basf Se Fungicidal pyrimidine compounds
WO2013124250A2 (en) 2012-02-20 2013-08-29 Basf Se Fungicidal substituted thiophenes
WO2013135672A1 (en) 2012-03-13 2013-09-19 Basf Se Fungicidal pyrimidine compounds
EA201491667A1 (en) 2012-03-13 2015-03-31 Басф Се FUNGICIDE PYRIMIDINE COMPOUNDS
WO2013144213A1 (en) 2012-03-30 2013-10-03 Basf Se N-substituted pyridinylidene compounds and derivatives for combating animal pests
WO2013144223A1 (en) 2012-03-30 2013-10-03 Basf Se N-substituted pyrimidinylidene compounds and derivatives for combating animal pests
US20150065343A1 (en) 2012-04-02 2015-03-05 Basf Se Acrylamide compounds for combating invertebrate pests
MX2014011995A (en) 2012-04-03 2015-09-04 Basf Se N- substituted hetero - bicyclic furanone derivatives for combating animal.
WO2013150115A1 (en) 2012-04-05 2013-10-10 Basf Se N- substituted hetero - bicyclic compounds and derivatives for combating animal pests
CA2868385A1 (en) 2012-05-04 2013-11-07 Basf Se Substituted pyrazole-containing compounds and their use as pesticides
ES2656543T3 (en) 2012-05-24 2018-02-27 Basf Se N-thio-anthranilamide compounds and their use as pesticides
MX2014015265A (en) 2012-06-14 2015-08-12 Basf Se Pesticidal methods using substituted 3-pyridyl thiazole compounds and derivatives for combating animal pests.
BR122019015104B1 (en) 2012-06-20 2020-04-07 Basf Se pesticide mixture, composition, agricultural composition, methods for combating or controlling invertebrate pests, for the protection of growing plants or plant propagation material, for the protection of plant propagation material and the use of a pesticide mixture
EP2871960A1 (en) 2012-07-13 2015-05-20 Basf Se Substituted thiadiazoles and their use as fungicides
WO2014009293A1 (en) 2012-07-13 2014-01-16 Basf Se New substituted thiadiazoles and their use as fungicides
US20150237858A1 (en) 2012-10-01 2015-08-27 Basf Se Method of controlling ryanodine-modulator insecticide resistant insects
AR093771A1 (en) 2012-10-01 2015-06-24 Basf Se METHOD TO CONTROL INSECTICIDE RESISTANT INSECTS
WO2014053407A1 (en) 2012-10-01 2014-04-10 Basf Se N-thio-anthranilamide compounds and their use as pesticides
EP2903442A1 (en) 2012-10-01 2015-08-12 Basf Se Pesticidally active mixtures comprising anthranilamide compounds
WO2014053401A2 (en) 2012-10-01 2014-04-10 Basf Se Method of improving plant health
CN104768378A (en) 2012-10-01 2015-07-08 巴斯夫欧洲公司 Use of N-thio-anthranilamide compounds on cultivated plants
EP2903438A1 (en) 2012-10-01 2015-08-12 Basf Se Pesticidally active mixtures comprising anthranilamide compounds
US20150257383A1 (en) 2012-10-12 2015-09-17 Basf Se Method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material
WO2014079820A1 (en) 2012-11-22 2014-05-30 Basf Se Use of anthranilamide compounds for reducing insect-vectored viral infections
US20150313229A1 (en) 2012-11-27 2015-11-05 Basf Se Substituted [1,2,4] Triazole Compounds
WO2014082879A1 (en) 2012-11-27 2014-06-05 Basf Se Substituted [1,2,4]triazole compounds
WO2014082871A1 (en) 2012-11-27 2014-06-05 Basf Se Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides
WO2014082881A1 (en) 2012-11-27 2014-06-05 Basf Se Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides
JP2016501206A (en) 2012-12-04 2016-01-18 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Novel substituted 1,4-dithiin derivatives and their use as fungicides
WO2014086850A1 (en) 2012-12-04 2014-06-12 Basf Agro B.V., Arnhem (Nl) Compositions comprising a quillay extract and a fungicidal inhibitor of respiratory complex ii
WO2014086856A1 (en) 2012-12-04 2014-06-12 Basf Agro B.V., Arnhem (Nl) Compositions comprising a quillay extract and a biopesticide
WO2014086854A1 (en) 2012-12-04 2014-06-12 Basf Agro B.V., Arnhem (Nl) Compositions comprising a quillay extract and a plant growth regulator
WO2014095381A1 (en) 2012-12-19 2014-06-26 Basf Se Fungicidal imidazolyl and triazolyl compounds
EP2746263A1 (en) 2012-12-19 2014-06-25 Basf Se Alpha-substituted triazoles and imidazoles
EP2746264A1 (en) 2012-12-19 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
CN106632107A (en) 2012-12-19 2017-05-10 巴斯夫欧洲公司 Substituted [1,2,4]triazole and their use as fungicides
WO2014095555A1 (en) 2012-12-19 2014-06-26 Basf Se New substituted triazoles and imidazoles and their use as fungicides
EP2746255A1 (en) 2012-12-19 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
EP2746275A1 (en) 2012-12-19 2014-06-25 Basf Se New substituted triazoles and imidazoles and their use as fungicides
EP2746279A1 (en) 2012-12-19 2014-06-25 Basf Se Fungicidal imidazolyl and triazolyl compounds
EP2746278A1 (en) 2012-12-19 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
EP2746256A1 (en) 2012-12-19 2014-06-25 Basf Se Fungicidal imidazolyl and triazolyl compounds
EP2745691A1 (en) 2012-12-19 2014-06-25 Basf Se Substituted imidazole compounds and their use as fungicides
EP2746266A1 (en) 2012-12-19 2014-06-25 Basf Se New substituted triazoles and imidazoles and their use as fungicides
EP2746274A1 (en) 2012-12-19 2014-06-25 Basf Se Substituted [1,2,4]triazole compounds
EP2746276A1 (en) 2012-12-19 2014-06-25 Basf Se New substituted triazoles and imidazoles and their use as fungicides
EP2746262A1 (en) 2012-12-19 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds for combating phytopathogenic fungi
BR112015014579A2 (en) 2012-12-19 2017-07-11 Basf Se compounds of formula i, use of a compound of formula i, method for combating harmful fungi and seeds.
BR112015014303A2 (en) 2012-12-19 2017-07-11 Basf Se compounds of formula I, process for the preparation of compounds of formula I, agrochemical compositions, use of a compound of formula I, method for combating fungi, seed and intermediate compounds xx3
WO2014095534A1 (en) 2012-12-19 2014-06-26 Basf Se New substituted triazoles and imidazoles and their use as fungicides
EP2746277A1 (en) 2012-12-19 2014-06-25 Basf Se Fungicidal imidazolyl and triazolyl compounds
CN105050406B (en) 2012-12-20 2017-09-15 巴斯夫农业公司 Compositions comprising triazole compounds
EP2746259A1 (en) 2012-12-21 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
EP2746260A1 (en) 2012-12-21 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
EP2746258A1 (en) 2012-12-21 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
EP2746257A1 (en) 2012-12-21 2014-06-25 Basf Se Substituted [1,2,4]triazole and imidazole compounds
US20150368236A1 (en) 2012-12-27 2015-12-24 Basf Se 2-(pyridin-3-yl)-5-hetaryl-thiazole compounds carrying an imine or imine-derived substituent for combating invertebrate pests
WO2014118099A1 (en) 2013-01-30 2014-08-07 Basf Se Fungicidal naphthoquinones and derivatives
WO2014124850A1 (en) 2013-02-14 2014-08-21 Basf Se Substituted [1,2,4]triazole and imidazole compounds
CA2899627C (en) 2013-03-20 2022-09-13 Basf Corporation Synergistic compositions comprising a bacillus subtilis strain and a pesticide
US20160278384A1 (en) 2013-03-20 2016-09-29 Basf Corporation Synergistic compositions comprising a bacillus subtilis strain and a biopesticide
EP2783569A1 (en) 2013-03-28 2014-10-01 Basf Se Compositions comprising a triazole compound
BR112015026357A2 (en) 2013-04-19 2017-07-25 Basf Se compost, agricultural or veterinary composition, methods for the control or control of pests, the protection of plants, the protection of propagating material and the treatment of animals and the use of a compost
KR20160005364A (en) 2013-05-10 2016-01-14 님버스 아폴로, 인코포레이티드 Acc inhibitors and uses thereof
EP2813499A1 (en) 2013-06-12 2014-12-17 Basf Se Substituted [1,2,4]triazole and imidazole compounds
EP2815647A1 (en) 2013-06-18 2014-12-24 Basf Se Novel strobilurin-type compounds for combating phytopathogenic fungi
EP2815649A1 (en) 2013-06-18 2014-12-24 Basf Se Fungicidal mixtures II comprising strobilurin-type fungicides
US20160145222A1 (en) 2013-06-21 2016-05-26 Basf Se Methods for Controlling Pests in Soybean
US9497970B2 (en) 2013-07-15 2016-11-22 Basf Se Pesticide compounds
WO2015011615A1 (en) 2013-07-22 2015-01-29 Basf Corporation Mixtures comprising a trichoderma strain and a pesticide
EP2835052A1 (en) 2013-08-07 2015-02-11 Basf Se Fungicidal mixtures comprising pyrimidine fungicides
EP2839745A1 (en) 2013-08-21 2015-02-25 Basf Se Agrochemical formulations comprising a 2-ethyl-hexanol alkoxylate
US20160221964A1 (en) 2013-09-16 2016-08-04 Basf Se Fungicidal pyrimidine compounds
WO2015036059A1 (en) 2013-09-16 2015-03-19 Basf Se Fungicidal pyrimidine compounds
CR20160180A (en) 2013-09-19 2016-10-03 Basf Se N-ACILIMINE HETEROCYCLIC COMPOUNDS
BR122021013202B1 (en) 2013-10-18 2022-03-08 Basf Agrochemical Products B.V. USE OF THE PESTICIDE ACTIVE CARBOXAMIDE COMPOUND AND METHOD OF PROTECTION OF VEGETABLE PROPAGATION MATERIAL
EP3080092B1 (en) 2013-12-12 2019-02-06 Basf Se Substituted [1,2,4]triazole and imidazole compounds
WO2015091645A1 (en) 2013-12-18 2015-06-25 Basf Se Azole compounds carrying an imine-derived substituent
US20160326153A1 (en) 2013-12-18 2016-11-10 Basf Se N-substituted imino heterocyclic compounds
WO2015104422A1 (en) 2014-01-13 2015-07-16 Basf Se Dihydrothiophene compounds for controlling invertebrate pests
EA201691913A1 (en) 2014-03-26 2017-02-28 Басф Се SUBSTITUTED [1,2,4] TRIAZOL AND IMIDAZOL COMPOUNDS AS FUNGICIDES
EP2924027A1 (en) 2014-03-28 2015-09-30 Basf Se Substituted [1,2,4]triazole and imidazole fungicidal compounds
EP2949216A1 (en) 2014-05-30 2015-12-02 Basf Se Fungicidal substituted alkynyl [1,2,4]triazole and imidazole compounds
EP2949649A1 (en) 2014-05-30 2015-12-02 Basf Se Fungicide substituted [1,2,4]triazole and imidazole compounds
AR100743A1 (en) 2014-06-06 2016-10-26 Basf Se COMPOUNDS OF [1,2,4] SUBSTITUTED TRIAZOL
EP2952507A1 (en) 2014-06-06 2015-12-09 Basf Se Substituted [1,2,4]triazole compounds
EP2952506A1 (en) 2014-06-06 2015-12-09 Basf Se Substituted [1,2,4]triazole and imidazole compounds
EP2952512A1 (en) 2014-06-06 2015-12-09 Basf Se Substituted [1,2,4]triazole compounds
UA121116C2 (en) 2014-06-06 2020-04-10 Басф Се Use of substituted oxadiazoles for combating phytopathogenic fungi
WO2016001110A1 (en) 2014-06-30 2016-01-07 Basf Se Process for producing 2-propionylalkanonitriles
EP2979549A1 (en) 2014-07-31 2016-02-03 Basf Se Method for improving the health of a plant
US10149477B2 (en) 2014-10-06 2018-12-11 Basf Se Substituted pyrimidinium compounds for combating animal pests
EP3209818B1 (en) 2014-10-24 2019-12-11 Basf Se Organic pesticid particles
BR112017009513A2 (en) 2014-11-06 2018-02-06 Basf Se use of a heterobicyclic compound, use of compounds i, compounds, agricultural or veterinary composition, method for pest control or control, method for crop and seed protection
EP3028573A1 (en) 2014-12-05 2016-06-08 Basf Se Use of a triazole fungicide on transgenic plants
AU2016214305B2 (en) 2015-02-06 2020-10-08 Basf Se Pyrazole compounds as nitrification inhibitors
WO2016128240A1 (en) 2015-02-11 2016-08-18 Basf Se Pesticidal mixture comprising a pyrazole compound and two fungicides
AU2016218096B2 (en) 2015-02-11 2020-02-20 Basf Se Pesticidal mixture comprising a pyrazole compound, an insecticide and a fungicide
US11064696B2 (en) 2015-04-07 2021-07-20 Basf Agrochemical Products B.V. Use of an insecticidal carboxamide compound against pests on cultivated plants
AU2016260805A1 (en) 2015-05-12 2017-11-23 Basf Se Thioether compounds as nitrification inhibitors
WO2016198611A1 (en) 2015-06-11 2016-12-15 Basf Se N-(thio)acylimino heterocyclic compounds
WO2016198613A1 (en) 2015-06-11 2016-12-15 Basf Se N-(thio)acylimino compounds
WO2017016883A1 (en) 2015-07-24 2017-02-02 Basf Se Process for preparation of cyclopentene compounds
CA2999378A1 (en) 2015-10-02 2017-04-06 Basf Se Imino compounds with a 2-chloropyrimidin-5-yl substituent as pest-control agents
WO2017060148A1 (en) 2015-10-05 2017-04-13 Basf Se Pyridine derivatives for combating phytopathogenic fungi
WO2017076757A1 (en) 2015-11-02 2017-05-11 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
EP3165094A1 (en) 2015-11-03 2017-05-10 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
EP3370525A1 (en) 2015-11-04 2018-09-12 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
EP3165093A1 (en) 2015-11-05 2017-05-10 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
EP3167716A1 (en) 2015-11-10 2017-05-17 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2017081312A1 (en) 2015-11-13 2017-05-18 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
EP3373732A1 (en) 2015-11-13 2018-09-19 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
CA3003949A1 (en) 2015-11-19 2017-05-26 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
JP2019502661A (en) 2015-11-19 2019-01-31 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ Substituted oxadiazoles for controlling plant pathogens
CA3004796C (en) 2015-11-25 2023-11-14 Gilead Apollo, Llc Pyrazole acc inhibitors and uses thereof
PL3380479T3 (en) 2015-11-25 2023-05-08 Gilead Apollo, Llc Triazole acc inhibitors and uses thereof
CA3004798C (en) 2015-11-25 2023-10-31 Gilead Apollo, Llc Ester acc inhibitors and uses thereof
CN113303339A (en) 2015-11-30 2021-08-27 巴斯夫欧洲公司 Mixture of cis-jasmone and bacillus amyloliquefaciens
EP3383849B1 (en) 2015-12-01 2020-01-08 Basf Se Pyridine compounds as fungicides
US10696634B2 (en) 2015-12-01 2020-06-30 Basf Se Pyridine compounds as fungicides
EP3205208A1 (en) 2016-02-09 2017-08-16 Basf Se Mixtures and compositions comprising paenibacillus strains or fusaricidins and chemical pesticides
EP3426660A1 (en) 2016-03-09 2019-01-16 Basf Se Spirocyclic derivatives
BR112018017034A2 (en) 2016-03-10 2018-12-26 Basf Se mixtures and their use, agrochemical composition, method of controlling phytopathogenic weeds and plant propagation material
CA3015131A1 (en) 2016-03-11 2017-09-14 Basf Se Method for controlling pests of plants
PL3436457T3 (en) 2016-04-01 2022-11-28 Basf Se Bicyclic compounds
US10986839B2 (en) 2016-04-11 2021-04-27 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
RU2018143590A (en) 2016-05-18 2020-06-18 Басф Се CAPSULES CONTAINING SIMPLE BENZYL PROPARGYL ETHERS INTENDED FOR USE AS NITRIFICATION INHIBITORS
WO2018050421A1 (en) 2016-09-13 2018-03-22 Basf Se Fungicidal mixtures i comprising quinoline fungicides
WO2018054723A1 (en) 2016-09-26 2018-03-29 Basf Se Pyridine compounds for controlling phytopathogenic harmful fungi
WO2018054711A1 (en) 2016-09-26 2018-03-29 Basf Se Pyridine compounds for controlling phytopathogenic harmful fungi
WO2018054721A1 (en) 2016-09-26 2018-03-29 Basf Se Pyridine compounds for controlling phytopathogenic harmful fungi
WO2018065182A1 (en) 2016-10-04 2018-04-12 Basf Se Reduced quinoline compounds as antifuni agents
WO2018073110A1 (en) 2016-10-20 2018-04-26 Basf Se Quinoline compounds as fungicides
KR20190092539A (en) 2016-12-16 2019-08-07 바스프 에스이 Insecticide compound
EP3555056A1 (en) 2016-12-19 2019-10-23 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
EP3339297A1 (en) 2016-12-20 2018-06-27 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
EP3338552A1 (en) 2016-12-21 2018-06-27 Basf Se Use of a tetrazolinone fungicide on transgenic plants
BR112019014061A2 (en) 2017-01-23 2020-02-04 Basf Se compounds of formula i, intermediates b, intermediates c, intermediates ii and intermediates d, composition, use, method to combat phytopathogenic fungi, seed and process for the synthesis of the compounds of formula i
WO2018149754A1 (en) 2017-02-16 2018-08-23 Basf Se Pyridine compounds
BR112019015338B1 (en) 2017-02-21 2023-03-14 Basf Se COMPOUNDS OF FORMULA I, AGROCHEMICAL COMPOSITION, COATED SEED, USE OF THE COMPOUNDS AND METHOD TO COMBAT HARMFUL PHYTOPATHOGENIC FUNGI
WO2018162312A1 (en) 2017-03-10 2018-09-13 Basf Se Spirocyclic derivatives
WO2018166855A1 (en) 2017-03-16 2018-09-20 Basf Se Heterobicyclic substituted dihydroisoxazoles
AU2018241406B2 (en) 2017-03-28 2021-11-11 Basf Se Pesticidal compounds
RU2765370C2 (en) 2017-03-31 2022-01-28 Басф Се Pyrimidinium compounds and mixtures thereof for suppressing vermin
CN110475772A (en) 2017-04-06 2019-11-19 巴斯夫欧洲公司 pyridine compound
RU2019136993A (en) 2017-04-20 2021-05-20 Пи Индастриз Лтд. NEW PHENYLAMINE COMPOUNDS
WO2018192793A1 (en) 2017-04-20 2018-10-25 Basf Se Substituted rhodanine derivatives
EP3618629A1 (en) 2017-05-02 2020-03-11 Basf Se Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles
BR112019022206A2 (en) 2017-05-05 2020-05-12 Basf Se FUNGICIDAL MIXTURES, AGRICULTURAL COMPOSITION, USE OF THE MIXTURE, METHODS FOR CONTROLLING PHYTOPATHOGENIC HARMFUL FUNGI AND PROTECTION OF PLANT PROPAGATION MATERIAL AND PLANT PROPAGATION MATERIAL
EP3625215B1 (en) 2017-05-18 2023-09-13 PI Industries Ltd Formimidamidine compounds useful against phytopathogenic microorganisms
WO2018219797A1 (en) 2017-06-02 2018-12-06 Basf Se Substituted oxadiazoles for combating phytopathogenic fungi
WO2018229202A1 (en) 2017-06-16 2018-12-20 Basf Se Mesoionic imidazolium compounds and derivatives for combating animal pests
BR112019025191B1 (en) 2017-06-19 2023-11-28 Basf Se SUBSTITUTED PYRIMIDINIUM COMPOUNDS, COMPOSITION, METHOD FOR PROTECTING CROPS, COATED SEED, USE OF THE COMPOUNDS AND USE OF A COMPOUND
EP3642187A1 (en) 2017-06-19 2020-04-29 Basf Se 2-[[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryloxy](thio)acetamides for combating phytopathogenic fungi
WO2018234488A1 (en) 2017-06-23 2018-12-27 Basf Se SUBSTITUTED CYCLOPROPYL DERIVATIVES
WO2019002158A1 (en) 2017-06-30 2019-01-03 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019025250A1 (en) 2017-08-04 2019-02-07 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019038042A1 (en) 2017-08-21 2019-02-28 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019042800A1 (en) 2017-08-29 2019-03-07 Basf Se Pesticidal mixtures
WO2019042932A1 (en) 2017-08-31 2019-03-07 Basf Se Method of controlling rice pests in rice
EP3453706A1 (en) 2017-09-08 2019-03-13 Basf Se Pesticidal imidazole compounds
US11076596B2 (en) 2017-09-18 2021-08-03 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019057660A1 (en) 2017-09-25 2019-03-28 Basf Se Indole and azaindole compounds with substituted 6-membered aryl and heteroaryl rings as agrochemical fungicides
EP3694852A1 (en) 2017-10-13 2020-08-19 Basf Se Imidazolidine pyrimidinium compounds for combating animal pests
US11147275B2 (en) 2017-11-23 2021-10-19 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
WO2019115511A1 (en) 2017-12-14 2019-06-20 Basf Se Fungicidal mixture comprising substituted 3-phenyl-5-(trifluoromethyl)-1,2,4-oxadiazoles
CA3084405A1 (en) 2017-12-15 2019-06-20 Basf Se Fungicidal mixture comprising substituted pyridines
WO2019123196A1 (en) 2017-12-20 2019-06-27 Pi Industries Ltd. Fluoralkenyl compounds, process for preparation and use thereof
WO2019121143A1 (en) 2017-12-20 2019-06-27 Basf Se Substituted cyclopropyl derivatives
BR112020012566B1 (en) 2017-12-21 2024-03-05 Basf Se COMPOUND OF FORMULA I, COMPOSITION, METHOD OF COMBAT OR CONTROL OF INVERTEBRATE PESTS, METHOD OF PROTECTING GROWING PLANTS AGAINST ATTACK OR INFESTATION BY INVERTEBRATE PESTS, COATED SEED, AND USES OF A COMPOUND OF FORMULA I
CA3087313A1 (en) 2018-01-09 2019-08-01 Basf Se Silylethynyl hetaryl compounds as nitrification inhibitors
WO2019137995A1 (en) 2018-01-11 2019-07-18 Basf Se Novel pyridazine compounds for controlling invertebrate pests
JP7538041B2 (en) 2018-01-30 2024-08-21 ピーアイ インダストリーズ リミテッド New oxadiazoles
WO2019150311A1 (en) 2018-02-02 2019-08-08 Pi Industries Ltd. 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms
US20200354321A1 (en) 2018-02-07 2020-11-12 Basf Se New pyridine carboxamides
WO2019154665A1 (en) 2018-02-07 2019-08-15 Basf Se New pyridine carboxamides
EP3530118A1 (en) 2018-02-26 2019-08-28 Basf Se Fungicidal mixtures
EP3530116A1 (en) 2018-02-27 2019-08-28 Basf Se Fungicidal mixtures comprising xemium
WO2019166252A1 (en) 2018-02-28 2019-09-06 Basf Se Fungicidal mixtures comprising fenpropidin
CA3093781A1 (en) 2018-02-28 2019-09-06 Basf Se Use of n-functionalized alkoxy pyrazole compounds as nitrification inhibitors
BR112020016425A2 (en) 2018-02-28 2020-12-15 Basf Se USE OF ALCOXIPYRAZOL COMPOUND, COMPOSITION FOR USE IN REDUCING NITRIFICATION, AGRICULTURAL MIXTURE AND METHODS OF REDUCING NITRIFICATION AND TREATMENT OF FERTILIZER OR COMPOSITION
CN111683528B (en) 2018-02-28 2022-12-13 巴斯夫欧洲公司 Use of pyrazolidinopropyl ethers as nitrification inhibitors
CN111801014B (en) 2018-03-01 2022-05-27 巴斯夫农业公司 Fungicidal compositions of cloroxen
EP3533333A1 (en) 2018-03-02 2019-09-04 Basf Se Fungicidal mixtures comprising pydiflumetofen
EP3533331A1 (en) 2018-03-02 2019-09-04 Basf Se Fungicidal mixtures comprising pydiflumetofen
EP3536150A1 (en) 2018-03-06 2019-09-11 Basf Se Fungicidal mixtures comprising fluxapyroxad
EP3762367A1 (en) 2018-03-09 2021-01-13 PI Industries Ltd. Heterocyclic compounds as fungicides
WO2019175713A1 (en) 2018-03-14 2019-09-19 Basf Corporation New catechol molecules and their use as inhibitors to p450 related metabolic pathways
WO2019175712A1 (en) 2018-03-14 2019-09-19 Basf Corporation New uses for catechol molecules as inhibitors to glutathione s-transferase metabolic pathways
WO2019185413A1 (en) 2018-03-27 2019-10-03 Basf Se Pesticidal substituted cyclopropyl derivatives
WO2019202459A1 (en) 2018-04-16 2019-10-24 Pi Industries Ltd. Use of 4-substituted phenylamidine compounds for controlling disease rust diseases in plants
WO2019219464A1 (en) 2018-05-15 2019-11-21 Basf Se Substituted trifluoromethyloxadiazoles for combating phytopathogenic fungi
KR102727205B1 (en) 2018-05-15 2024-11-06 바스프 에스이 Mixtures containing benzpyrimoxane and oxazosulpirin, uses thereof and methods of application thereof
WO2019224092A1 (en) 2018-05-22 2019-11-28 Basf Se Pesticidally active c15-derivatives of ginkgolides
WO2020002472A1 (en) 2018-06-28 2020-01-02 Basf Se Use of alkynylthiophenes as nitrification inhibitors
WO2020020777A1 (en) 2018-07-23 2020-01-30 Basf Se Use of substituted 2-thiazolines as nitrification inhibitors
DK3826982T3 (en) 2018-07-23 2024-01-22 Basf Se USE OF A SUBSTITUTED THIAZOLIDE COMPOUND AS A NITRIFICATION INHIBITOR
TW202009235A (en) 2018-08-17 2020-03-01 印度商皮埃企業有限公司 1,2-dithiolone compounds and use thereof
EP3613736A1 (en) 2018-08-22 2020-02-26 Basf Se Substituted glutarimide derivatives
EP3628158A1 (en) 2018-09-28 2020-04-01 Basf Se Pesticidal mixture comprising a mesoionic compound and a biopesticide
EP3628157A1 (en) 2018-09-28 2020-04-01 Basf Se Method of controlling insecticide resistant insects and virus transmission to plants
CA3112042A1 (en) 2018-09-28 2020-04-02 Basf Se Method of controlling pests by seed treatment application of a mesoionic compound or mixture thereof
EP3628156A1 (en) 2018-09-28 2020-04-01 Basf Se Method for controlling pests of sugarcane, citrus, rapeseed, and potato plants
JP2022501410A (en) 2018-10-01 2022-01-06 ピーアイ インダストリーズ リミテッドPi Industries Ltd New oxadiazole
AR116557A1 (en) 2018-10-01 2021-05-19 Pi Industries Ltd OXADIAZOLES
EP3643705A1 (en) 2018-10-24 2020-04-29 Basf Se Pesticidal compounds
WO2020095161A1 (en) 2018-11-05 2020-05-14 Pi Industries Ltd. Nitrone compounds and use thereof
CN113166063B (en) 2018-11-28 2025-02-25 巴斯夫欧洲公司 Insecticidal compounds
EP3670501A1 (en) 2018-12-17 2020-06-24 Basf Se Substituted [1,2,4]triazole compounds as fungicides
US20230031024A1 (en) 2018-12-18 2023-02-02 Basf Se Substituted pyrimidinium compounds for combating animal pests
EP3696177A1 (en) 2019-02-12 2020-08-19 Basf Se Heterocyclic compounds for the control of invertebrate pests
KR20210150405A (en) 2019-04-08 2021-12-10 피아이 인더스트리스 엘티디. Novel oxadiazole compounds for controlling or preventing phytopathogenic fungi
US20220151234A1 (en) 2019-04-08 2022-05-19 Pi Industries Ltd. Novel oxadiazole compounds for controlling or preventing phytopathogenic fungi
KR20210148174A (en) 2019-04-08 2021-12-07 피아이 인더스트리스 엘티디. Novel oxadiazole compounds for controlling or preventing phytopathogenic fungi
EP3730489A1 (en) 2019-04-25 2020-10-28 Basf Se Heteroaryl compounds as agrochemical fungicides
CN113923987B (en) 2019-05-29 2024-10-01 巴斯夫欧洲公司 Mesoionic imidazolium compounds and derivatives for controlling animal pests
EP3769623A1 (en) 2019-07-22 2021-01-27 Basf Se Mesoionic imidazolium compounds and derivatives for combating animal pests
KR20220017940A (en) 2019-06-06 2022-02-14 바스프 에스이 fungicidal N-(pyrid-3-yl)carboxamide
WO2020244970A1 (en) 2019-06-06 2020-12-10 Basf Se New carbocyclic pyridine carboxamides
WO2020244969A1 (en) 2019-06-06 2020-12-10 Basf Se Pyridine derivatives and their use as fungicides
EP3766879A1 (en) 2019-07-19 2021-01-20 Basf Se Pesticidal pyrazole derivatives
AR119774A1 (en) 2019-08-19 2022-01-12 Pi Industries Ltd OXADIAZOLE COMPOUNDS CONTAINING A 5-MEMBER HETEROAROMATIC RING TO CONTROL OR PREVENT PHYTOPATHOGENIC FUNGI
WO2021063735A1 (en) 2019-10-02 2021-04-08 Basf Se New bicyclic pyridine derivatives
WO2021063736A1 (en) 2019-10-02 2021-04-08 Basf Se Bicyclic pyridine derivatives
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WO2021175669A1 (en) 2020-03-04 2021-09-10 Basf Se Use of substituted 1,2,4-oxadiazoles for combating phytopathogenic fungi
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EP3909950A1 (en) 2020-05-13 2021-11-17 Basf Se Heterocyclic compounds for the control of invertebrate pests
WO2021249800A1 (en) 2020-06-10 2021-12-16 Basf Se Substituted [1,2,4]triazole compounds as fungicides
EP3945089A1 (en) 2020-07-31 2022-02-02 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors v
EP3960727A1 (en) 2020-08-28 2022-03-02 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors vi
EP3939961A1 (en) 2020-07-16 2022-01-19 Basf Se Strobilurin type compounds and their use for combating phytopathogenic fungi
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EP3970494A1 (en) 2020-09-21 2022-03-23 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors viii
WO2022038500A1 (en) 2020-08-18 2022-02-24 Pi Industries Limited Novel heterocyclic compounds for combating phytopathogenic fungi
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TW202229241A (en) 2020-09-26 2022-08-01 印度商皮埃企業有限公司 Nematocidal compounds and use thereof
EP4236691A1 (en) 2020-10-27 2023-09-06 BASF Agro B.V. Compositions comprising mefentrifluconazole
WO2022090069A1 (en) 2020-11-02 2022-05-05 Basf Se Compositions comprising mefenpyr-diethyl
WO2022090071A1 (en) 2020-11-02 2022-05-05 Basf Se Use of mefenpyr-diethyl for controlling phytopathogenic fungi
WO2022106304A1 (en) 2020-11-23 2022-05-27 BASF Agro B.V. Compositions comprising mefentrifluconazole
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UY39780A (en) 2021-05-26 2022-11-30 Pi Industries Ltd FUNGICIDAL COMPOSITION CONTAINING OXADIAZOLE COMPOUNDS
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EP4358725A1 (en) 2021-06-21 2024-05-01 Basf Se Metal-organic frameworks with pyrazole-based building blocks
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KR20240042636A (en) 2021-08-02 2024-04-02 바스프 에스이 (3-pyridyl)-quinazoline
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EP4140995A1 (en) 2021-08-27 2023-03-01 Basf Se Pyrazine compounds for the control of invertebrate pests
EP4151631A1 (en) 2021-09-20 2023-03-22 Basf Se Heterocyclic compounds for the control of invertebrate pests
WO2023072671A1 (en) 2021-10-28 2023-05-04 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors ix
WO2023072670A1 (en) 2021-10-28 2023-05-04 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors x
EP4194453A1 (en) 2021-12-08 2023-06-14 Basf Se Pyrazine compounds for the control of invertebrate pests
EP4198033A1 (en) 2021-12-14 2023-06-21 Basf Se Heterocyclic compounds for the control of invertebrate pests
EP4198023A1 (en) 2021-12-16 2023-06-21 Basf Se Pesticidally active thiosemicarbazone compounds
AR127972A1 (en) 2021-12-17 2024-03-13 Pi Industries Ltd NOVEL FUSED SUBSTITUTED BICYCLIC CARBOXAMIDE PYRIDINE COMPOUNDS TO COMBAT PHYTOPATHOGENIC FUNGI
EP4238971A1 (en) 2022-03-02 2023-09-06 Basf Se Substituted isoxazoline derivatives
WO2023203066A1 (en) 2022-04-21 2023-10-26 Basf Se Synergistic action as nitrification inhibitors of dcd oligomers with alkoxypyrazole and its oligomers
CN119110681A (en) 2022-04-25 2024-12-10 巴斯夫欧洲公司 Emulsifiable concentrates with (substituted) benzaldehyde-based solvent systems
EP4565581A1 (en) 2022-08-02 2025-06-11 Basf Se Pyrazolo pesticidal compounds
EP4342885A1 (en) 2022-09-20 2024-03-27 Basf Se N-(3-(aminomethyl)-phenyl)-5-(4-phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-amine derivatives and similar compounds as pesticides
EP4361126A1 (en) 2022-10-24 2024-05-01 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors xv
WO2024104813A1 (en) 2022-11-14 2024-05-23 Basf Se Fungicidal mixture comprising substituted pyridines
CN120202196A (en) 2022-11-16 2025-06-24 巴斯夫欧洲公司 Substituted benzodiazepines as fungicides
WO2024104823A1 (en) 2022-11-16 2024-05-23 Basf Se New substituted tetrahydrobenzoxazepine
JP2025537793A (en) 2022-11-16 2025-11-20 ビーエーエスエフ ソシエタス・ヨーロピア Fungicidal mixtures containing substituted pyridines
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CN120202194A (en) 2022-11-16 2025-06-24 巴斯夫欧洲公司 Substituted tetrahydrobenzodiazepines as fungicides
EP4389210A1 (en) 2022-12-21 2024-06-26 Basf Se Heteroaryl compounds for the control of invertebrate pests
WO2024165343A1 (en) 2023-02-08 2024-08-15 Basf Se New substituted quinoline compounds for combatitng phytopathogenic fungi
AU2024238668A1 (en) 2023-03-17 2025-09-25 Basf Se Substituted pyridyl/pyrazidyl dihydrobenzothiazepine compounds for combatting phytopathogenic fungi
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WO2024223034A1 (en) 2023-04-26 2024-10-31 Basf Se Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors xvi
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EP4488270A1 (en) 2023-07-06 2025-01-08 Basf Se Triazole compounds for the control of invertebrate pests
EP4488269A1 (en) 2023-07-06 2025-01-08 Basf Se Triazole compounds for the control of invertebrate pests
EP4488273A1 (en) 2023-07-06 2025-01-08 Basf Se Triazole compounds for the control of invertebrate pests
WO2025031843A1 (en) 2023-08-09 2025-02-13 Basf Se New substituted benzoxazine picolinonitrile compounds for combatting phytopathogenic fungi
WO2025031842A1 (en) 2023-08-09 2025-02-13 Basf Se New substituted benzoxazepine picolinonitrile compounds for combatting phytopathogenic fungi
WO2025078181A1 (en) 2023-10-09 2025-04-17 Basf Se Fungicidal mixture comprising substituted pyridines
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WO2025223904A1 (en) 2024-04-24 2025-10-30 Basf Se Mixtures of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors with at least one further pesticide i
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WO2026012814A1 (en) 2024-07-10 2026-01-15 Basf Se Compositions and methods to enhance crop yield and plant health
WO2026021909A1 (en) 2024-07-23 2026-01-29 Basf Se New substituted benzothiazine pyridine compounds for combatting phytopathogenic fungi
WO2026021910A1 (en) 2024-07-23 2026-01-29 Basf Se New substituted benzothiazine pyridine compounds for combatting phytopathogenic fungi
WO2026021912A1 (en) 2024-07-23 2026-01-29 Basf Se New substituted benzothiazine pyridine compounds for combatting phytopathogenic fungi
WO2026021911A1 (en) 2024-07-23 2026-01-29 Basf Se New substituted benzothiazine pyridine compounds for combatting phytopathogenic fungi

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE564048A (en) *
US2444606A (en) * 1945-12-15 1948-07-06 Gen Aniline & Film Corp Stabilizers for photographic emulsions
US3157655A (en) * 1962-05-18 1964-11-17 Shionogi & Co Pyrazolopyrimidine derivative
GB1148629A (en) * 1966-10-03 1969-04-16 Hydrierwerk Rodleben Veb s-triazolo(1,5-a) pyrimidines substituted in the 7-position by a basic group
DD99794A1 (en) * 1966-09-27 1973-08-20
FR2448542A1 (en) * 1979-02-06 1980-09-05 Landerlan Sa Lab 7-Amino 1,2,4-triazolo 2,3-A pyrimidine(s) - are coronary vasodilators, hypoglycemics and anaphylaxis inhibitors
CA1180329A (en) * 1981-08-01 1985-01-02 Karl Eicken 7-aminoazolo[1,5-a]pyrimidines and fungicides containing these compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3533050A1 (en) * 1985-09-17 1987-03-26 Basf Ag 7-AMINO-AZOLO (1,5-A) PYRIMIDINE, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THEM, OR THEIR USE AS FUNGICIDES

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE564048A (en) *
US2444606A (en) * 1945-12-15 1948-07-06 Gen Aniline & Film Corp Stabilizers for photographic emulsions
US3157655A (en) * 1962-05-18 1964-11-17 Shionogi & Co Pyrazolopyrimidine derivative
DD99794A1 (en) * 1966-09-27 1973-08-20
GB1148629A (en) * 1966-10-03 1969-04-16 Hydrierwerk Rodleben Veb s-triazolo(1,5-a) pyrimidines substituted in the 7-position by a basic group
FR2448542A1 (en) * 1979-02-06 1980-09-05 Landerlan Sa Lab 7-Amino 1,2,4-triazolo 2,3-A pyrimidine(s) - are coronary vasodilators, hypoglycemics and anaphylaxis inhibitors
CA1180329A (en) * 1981-08-01 1985-01-02 Karl Eicken 7-aminoazolo[1,5-a]pyrimidines and fungicides containing these compounds

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5854252A (en) * 1993-03-04 1998-12-29 Shell Internationale Research Maatschappij B.V. Dihalotriazolopyrimidine derivatives
US5612345A (en) * 1993-03-04 1997-03-18 Shell Internationale Research Maatschappij B.V. Dihalotriazolopyrimidine derivatives as fungicides
US20070173408A1 (en) * 2004-03-10 2007-07-26 Blasco Jordi T I 5,6-Dialkyl-7-aminotriazolopyrimidines, their preparation and their use for controlling harmful fungi, and compositions comprising these compounds
US9487519B2 (en) * 2004-03-10 2016-11-08 Basf Se 5,6-Dialkyl-7-aminotriazolopyrimidines, their preparation and their use for controlling harmful fungi, and compositions comprising these compounds
US20080262000A1 (en) * 2005-02-16 2008-10-23 Basf Aktiengesellschaft 5-Alkoxyalkyl-6-alkyl-7-Aminoazolopyrimidines, Process for Their Preparation, Their Use for Controlling Harmful Fungi, and Compositions Comprising Them
US20080125445A1 (en) * 2005-03-01 2008-05-29 Basf Aktiengesellschaft 5,6-Dialkyl-7-Amino-Azolopyrimidines, Method For Their Production, Their Use For Controlling Pathogenic Fungi and Agents Containing Said Compounds
US20080188493A1 (en) * 2005-03-01 2008-08-07 Basf Aktiengesellschaft 5,6-Dialkyl-7-Aminoazolopyrimidines, Their Preparation and Their Use For Controlling Harmful Fungi, and Compositions Comprising These Compounds
US20080207455A1 (en) * 2005-03-01 2008-08-28 Basf Aktingesellschaft 5,6-Dialkyl-7-Aminoazolopyrimidines, Their Preparation and Their Use for Controlling Harmful Fungi, and Compositions Comprising These Compounds
US20080139581A1 (en) * 2005-03-02 2008-06-12 Basf Aktiengesellschaft 2-Substituted 7-Aminoazolopyrimidines, Processes For Their Preparation And Their Use For Controlling Harmful Fungi, And Compositions Comprising These Compounds
US20080176744A1 (en) * 2005-03-10 2008-07-24 Basf Aktiengesellschaft Use of 4-Aminopyrimidines for Controlling Harmful Fungi, Novel 4-Aminopyrimidines, Processes for Their Preparation and Compositions Comprising Them
US20080146839A1 (en) * 2005-03-18 2008-06-19 Basf Aktiengesellschaft Method for Producing 5-Halo-2,4,6-Trifluoroisophthalic Acid
US20080312078A1 (en) * 2005-07-27 2008-12-18 Basf Aktiengesellschaft 6-Phenyl-Pyrazolopyrimidine-7-Ylamine Fungicides
US20090156398A1 (en) * 2005-07-27 2009-06-18 Basf Aktiengesellschaft Fungicidal 5-alkyl-6-phenylpyrazolopyrimidin-7-ylamines
US20080221130A1 (en) * 2005-07-27 2008-09-11 Basf Aktiengesellschaft Fungicidal 5-Methyl-6-Phenylpyrazolopyrimidin-7-Ylamines
US20100087640A1 (en) * 2007-01-11 2010-04-08 Basf Se Method for production of aryl-substituted annelated pyrimidines
US20100105903A1 (en) * 2007-03-02 2010-04-29 Basf Se Method for the production of beta-ketonitriles
US8309751B2 (en) 2007-03-02 2012-11-13 Basf Se Method for the production of β-ketonitriles
US8501748B2 (en) 2007-03-02 2013-08-06 Basf Se Method for the production of β-ketonitriles
US9288996B2 (en) 2010-03-18 2016-03-22 Basf Se Fungicidal compositions comprising a phosphate solubilizing microorganism and a fungicidally active compound
US20130252951A1 (en) * 2010-09-27 2013-09-26 Proximagen Limited 7-hydroxy-pyrazolo[1,5-a] pyrimidine compounds and their use as ccr2 receptor antagonists
CN111683951A (en) * 2018-02-02 2020-09-18 勃林格殷格翰国际有限公司 Triazolopyrimidine derivatives useful as ghrelin O-acyltransferase (GOAT) inhibitors
CN111683951B (en) * 2018-02-02 2023-10-13 勃林格殷格翰国际有限公司 Triazolopyrimidine derivatives as ghrelin O-acyltransferase (GOAT) inhibitors

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US4617303A (en) 1986-10-14
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