Classifications

• • 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
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/647—Triazoles; Hydrogenated triazoles
  • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • 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
  • 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

Definitions

• 6- (2-tolyl) -triazolopy ⁇ m ⁇ d ⁇ nen as fungicides
• new 6- (2-tolyl) -triazolopyrimidines processes for their preparation and their use for controlling harmful fungi and agents containing them
• the present invention relates to the use of substituted triazolopyrimidines of the formula I.
• R 2 is hydrogen or one of the groups mentioned for R 1 ;
• R 1 and / or R 2 can carry one to four identical or different groups R a :
• R a chlorine, bromine, iodine, cyano, nitro, hydroxy, dC ⁇ -alkyl, d-Ce-haloalkyl, d-Ce-alkylcarbonyl, C 3 -C 6 -cycloalkyl, CrC 6 -alkoxy, dC 6 -haloalkoxy, dC 6 -alkoxycarbonyl, dC 6 -alkylthio, d-Ce-alkylamino, di-C ⁇ -C 6 -alkylamino, C 2 -C 8 -alkenyl, C 2 -C 8 -halogenalkenyl, C 3 -C 8 -cycloalkenyl, C 2 -C 6 alkenyloxy, C 3 -C 6 haloalkenyloxy, C 2 -C 6 alkynyl, C ⁇ -Ce haloalkynyl, C 3 -C 6 alkyn
• the invention also relates to new 6- (2-tolyl) -triazolopyrimidines, processes for the preparation of these compounds, compositions containing them and their use for controlling phytopathogenic harmful fungi.
• 5-Chloro-6- (2-tolyl) -7-aminotriazolopyrimidines are generally known from EP-A 71 792 and EP-A 550 113.
• WO 98/46608 discloses 6- (2-tolyl) -7-aminotriazolopyrimidines with special 7-amino groups.
• WO 03/008417 proposes 6- (2-tolyl) -7-aminotriazolopyrimidines whose phenyl group bears an additional substituent. These compounds are known for combating harmful fungi.
• the compounds according to the invention differ from the compounds mentioned in the abovementioned publications by the configuration of the substituents of the 7-amino group or by the less complex substitution of the 6-phenyl ring.
• the present invention has the object based on providing compounds with improved activity and / or broadened spectrum of activity.
• the new compounds according to the invention can be obtained in various ways.
• This reaction usually takes place at temperatures from 80 ° C. to 250 ° C., preferably 120 ° C. to 180 ° C., without solvent or in an inert organic solvent in the presence of a base [cf. EP-A 770 615] or in the presence of acetic acid among those from Adv. Het. Chem. Vol. 57, pp. 81ff. (1993) known conditions.
• Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, ethers, nitriles, ketones, alcohols, and also N-methylpyrrolidone, dimethyl sulfoxide, dimethylformamide and dimethylacetamide.
• the reaction is particularly preferably carried out without a solvent or in chlorobenzene, xylene, dimethyl sulfoxide, N-methylpyrrolidone. Mixtures of the solvents mentioned can also be used.
• Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal oxides, alkali metal and alkaline earth metal, alkali metal amides, alkali metal and alkaline earth metal and Al kalimetallhydrogencarbonate, organometallic compounds, particularly alkali tallalkyle, alkyl magnesium halides and alkali metal and alkaline earth metal and Dimethoxymagnesium, also organic bases, for example tertiary amines such as trimethylamine, methylamine, tri-isopropylethylamine, tributylamine and N-methylpiperidine, N-methylmorpholine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethyl aminopyridine and bicyclic amines. Tertiary amines such as tri-isopropylethylamine, tributylamine, N-methylmorpholine or N-methylpiperidine are
• the bases are generally used in catalytic amounts, but they can also be used in equimolar amounts, in excess or, if appropriate, as a solvent.
• the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use the base and the malonate III in an excess based on the triazole.
• Phenylmalonates of the formula IM are advantageously obtained from the reaction of appropriately substituted bromobenzenes with dialkylmalonates with Cu (I) catalysis [cf. Chemistry Letters, pp. 367-370, 1981; EP-A 10 02 788].
• the dihydroxytriazolopyrimidines of the formula IV are converted under the conditions known from WO-A 94/20501 into the dihalopyrimidines of the formula V in which shark means a halogen atom, preferably a bromine or a chlorine atom, in particular a chlorine atom.
• a halogenating agent [HAL] is advantageously a chlorinating agent or a brominating agent, such as phosphorus oxybromide or phosphorus oxychloride, optionally in the presence of a solvent.
• This reaction is usually carried out at 0 ° C. to 150 ° C., preferably at 80 ° C. to 125 ° C. [cf. EP-A 770 615].
• This reaction is advantageously carried out at 0 ° C to 70 ° C, preferably 10 ° C to 35 ° C, preferably in the presence of an inert solvent such as ether, e.g. B. dioxane, diethyl ether or in particular tetrahydrofuran, halogenated hydrocarbon fe, such as dichloromethane and aromatic hydrocarbons, such as toluene [cf. WO-A 98/46608].
• ether e.g. B. dioxane, diethyl ether or in particular tetrahydrofuran
• halogenated hydrocarbon fe such as dichloromethane
• aromatic hydrocarbons such as toluene [cf. WO-A 98/46608].
• a base such as tertiary amines, for example triethylamine or inorganic amines, such as potassium carbonate, is preferred; Excess amine of the formula VI can also serve as the base.
• the reaction mixtures are worked up in a conventional manner, e.g. by mixing with water, separation of the phases and, if necessary, chromatographic purification of the crude products.
• the intermediate and end products fall in part. in the form of colorless or slightly brownish, viscous oils, which are freed from volatile components or purified under reduced pressure and at a moderately elevated temperature. If the intermediate and end products are obtained as solids, they can also be purified by recrystallization or digesting.
• isomer mixtures occur during the synthesis, however, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the action of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus to be controlled.
• Halogen fluorine, chlorine, bromine and iodine, especially chlorine
• Alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 8 carbon atoms, for example dC 6 alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1- Dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2- Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1- Ethylbutyl, 2-ethylbutyl,
• C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1 -Butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl , 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl , 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1 -propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-propenyl, 1-ethy
• Alkynyl straight-chain or branched hydrocarbon groups with 2 to 4, 6 or 8 carbon atoms and one or two triple bonds in any position, for example C 2 -C 6 -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl , 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2nd -Methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5 -Hexyl, 1-methyl-2
• Cycloalkyl mono- or bicyclic, saturated hydrocarbon groups with 3 to 6 or 8 carbon ring members, for example C 3 -C 8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
• 5- or 6-membered heterocyclyl containing one to three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2 -Pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl , 5-oxazolidinyl, 5-oxazolidinyl, 5-oxazolidinyl, 5-oxazolidinyl, 5-oxazolidinyl
• 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom
• 5-ring heteroaryl groups which in addition to carbon atoms can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, eg 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, and 1, 3,4-triazol-2-yl;
• 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl;
• the scope of the present invention includes the (R) and (S) isomers and the racemates of compounds of the formula I which have chiral centers.
• R 1 is C 4 -C 8 alkyl or C 4 -C 8 alkenyl.
• R represents C 3 -C 6 cycloalkyl, which may be substituted by dC 4 alkyl.
• R 1 and / or R 2 contain haloalkyl or haloalkenyl groups with a chiral center, the (S) isomers are preferred for these groups.
• the (R) -configured isomers are preferred.
• a preferred embodiment of the invention relates to the use of compounds of the formula 1.1:
• GC 2 -C 6 alkyl especially ethyl, n- and i-propyl, n-, sec-, tert-butyl, and -CC alkoxymethyl, especially ethoxymethyl, or C 3 -C 6 cycloalkyl, especially cyclopentyl or Cyclohexyl mean.
• R 1 is C 3 -C 8 -cycloalkyl, C 3 -C 8 -halogenocycloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -halogenalkenyl, C 3 -C 6 are preferred -Cycloalkenyl, C 3 -C 6 halo-cycloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl or naphthyl, or a five or six-membered saturated, partially unsaturated or aromatic heterocycle containing one to four heteroatoms from the group O, N or S, which can be substituted as defined in the introduction.
• X and R 2 are defined according to claim 1 and G represents ethyl, n- and iso-propyl, n- and sec-butyl.
• the compounds I are suitable as fungicides in crop protection. They are characterized by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as foliar, stain and soil fungicides.
• the compounds I are also suitable for combating harmful fungi such as Pacilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
• harmful fungi such as Pacilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
• the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds.
• the application can take place both before and after the infection of the materials, plants or seeds by the fungi.
• the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
• the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
• active compound of 1 to 1000 g / 100 kg of seed, preferably 1 to 200 g / 100 kg, in particular 5 to 100 g / 100 kg, are generally used.
• the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.
• the compounds I can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules.
• the form of application depends on the respective purpose; it should be in everyone Case ensure a fine and uniform distribution of the compound of the invention.
• the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants.
• solvents and auxiliaries The following are essentially considered as solvents / auxiliaries:
• aromatic solvents e.g. Solvesso products, xylene
• paraffins e.g. petroleum fractions
• alcohols e.g. methanol, butanol, pentanol, benzyl alcohol
• ketones e.g. cyclohexanone, gamma-butryolactone
• pyrrolidones NMP, NOP
• Acetates glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
• solvent mixtures can also be used
• Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
• natural stone powder e.g. kaolins, clays, talc, chalk
• synthetic stone powder e.g. highly disperse silica, silicates
• Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
• mineral oil fractions from medium to high boiling points such as kerosene or diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, e.g. Dimethyl sulfoxide, N-methylpyrrolidone or water into consideration.
• mineral oil fractions from medium to high boiling points such as kerosene or diesel oil
• coal tar oils as well as oils of vegetable or animal origin
• aliphatic, cyclic and aromatic hydrocarbons e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated
• Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
• Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
• Solid carriers are, for example, mineral earths, such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate , Ammonium nitrate, ureas and vegetable products, such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
• mineral earths such as silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate , Ammonium nitrate, ureas and vegetable products
• the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient.
• the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
• formulations are: 1. Products for dilution in water
• a compound according to the invention 10 parts by weight of a compound according to the invention are dissolved in water or a water-soluble solvent. Alternatively, wetting agents or other aids are added. The active ingredient dissolves when diluted in water.
• a compound according to the invention 20 parts by weight of a compound according to the invention are dissolved in cyclohexanone with the addition of a dispersant e.g. Dissolved polyvinyl pyrrolidone. When diluted in water, a dispersion results.
• a dispersant e.g. Dissolved polyvinyl pyrrolidone.
• a compound according to the invention 20 parts by weight of a compound according to the invention are comminuted in a stirred ball mill to form a fine active ingredient suspension with the addition of dispersing and wetting agents and water or an organic solvent. Dilution in water results in a stable suspension of the active ingredient.
• a compound according to the invention 50 parts by weight of a compound according to the invention are finely ground with the addition of dispersing and wetting agents and produced as technical equipment (e.g. extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
• technical equipment e.g. extrusion, spray tower, fluidized bed
• WP, SP Water-dispersible and water-soluble powders 75 parts by weight of a compound according to the invention are ground in a rotor-strator mill with the addition of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
• a compound according to the invention 0.5 part by weight is ground finely and combined with 95.5% carriers.
• Common processes are extrusion, spray drying or fluidized bed. This gives granules for direct application.
• the active ingredients as such in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents, granules by spraying, atomizing, dusting, scattering or Pouring can be applied.
• the application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
• Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
• emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
• wetting agents, adhesives, dispersants or emulsifiers, and possibly solvents or oil can also be prepared from active substance and are suitable for dilution with water.
• the active ingredient concentrations in the ready-to-use preparations can be varied over a wide range. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
• the active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
• UUV ultra-low-volume process
• compositions according to the invention can also be present together with other active compounds which, e.g. with herbicides, insecticides, growth regulators, fungicides or also with fertilizers. Mixing the compounds I or the compositions containing them in the use form as fungicides with other fungicides results in an enlargement of the fungicidal spectrum of action in many cases.
• Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl, • Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine, tridemorph
• Anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl,
• Antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin,
• Azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, enilconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, pencon , Triticonazole,
• Dicarboximides such as iprodione, myclozolin, procymidone, vinclozolin,
• Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propineb, Polycarbamat, Thiram, Ziram, Zineb,
• Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadone, fenamidon, fenarimol, isoprothiolan, mandipropamide, probinolone, probinilone Pyrifenox, pyroquilon, quinoxyfen, silthiofam, SYP-Z048, thiabendazole, thifluzamide, thiophanate-methyl, tiadinil, tricyclazole, triforine, • copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate,
• Nitrophenyl derivatives such as binapacryl, dinocap, dinobuton, nitrophthal-isopropyl
• Phenylpyrroles such as fenpiclonil or fludioxonil
• Strobilurins such as azoxystrobin, dimoxystrobin, enestroburin (SYP-Z071), fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin,
• Sulfenic acid derivatives such as Captafol, Captan, dichlofluanid, Folpet, Tolylfluanid • Cinnamic acid amides and analogues such as Dimethomorph, Flumetover or Flumorph.
• the active ingredients were prepared as a stock solution with 0.25% by weight of active ingredient in acetone or DMSO. 1% by weight of emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration.
• emulsifier Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
• Example of use 1 - Efficacy against the drought stain disease of the tomato caused by Altemaria solani Leaves of potted plants of the "Golden Princess" variety were sprayed to runoff point with an aqueous suspension in the active compound concentration given below. The following day, the leaves were infected with an aqueous spore suspension of Altemaria solani in 2% biomalt solution with a density of 0.17 x 10 6 spores / ml. The plants were then placed in a water vapor-saturated chamber at temperatures between 20 and 22 ° C. After 5 days the disease had developed so strongly on the untreated but infected control plants that the infestation could be determined visually in%.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Dentistry (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Agronomy & Crop Science (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)
• Plural Heterocyclic Compounds (AREA)

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