Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/32—One oxygen, sulfur or nitrogen atom
  • C07D239/42—One nitrogen atom
• • 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
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
• • 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
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
• • 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
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
• • 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
• • 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
  • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
• • 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
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
  • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
  • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D473/00—Heterocyclic compounds containing purine ring systems
  • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
  • C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
  • C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
• • 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

• R 1 five- to ten-membered saturated, partially unsaturated or aromatic mono- or bicyclic heterocycle, containing one to four heteroatoms from the group 0, N or S, with the exception of pyridyl, where
• R 1 can be substituted by one to three identical or different groups R a ,
• R halogen, hydroxy, cyano, oxo, nitro, amino / mercapto, -CC 6 alkyl, Cx-Cg haloalkyl, C 2 -C 6 alkenyl,
• Ci-C ⁇ -alkylamino di- (Ci-Ce-alkyl) a ino, Ci-Cg-alkylthio, Ci-C ⁇ -alkylsulfinyl, Ci-Cg-alkylsulfonyl, hydroxysulfonyl, aminosulfonyl, C ⁇ -C 6 -alkylamino- sulfonyl, di- (-C 6 alkyl) aminosulfonyl;
• R 2 is hydrogen, halogen, cyano, Ci-Cg-alkyl, Ci-C ⁇ -halo-alkyl, Ci-C ⁇ -alkoxy, -C-C 4 -haloalkoxy or C 3 -C 6 -alkenyloxy;
• R 3 , R 4 independently of one another are hydrogen, C ⁇ -C 6 -alkyl
• C] .- C 6 -haloalkyl and oxy-C ⁇ -C 3 -alkyleneoxy can wear or in which two adjacent C atoms or an N and an adjacent C atoms can be connected by a C 1 -C 4 alkylene chain;
• R 5 , R 6 independently of one another are hydrogen, halogen, Ci-C ß- alkyl, _ Ci-Cg-haloalkyl or Ci-C ⁇ - alkoxy;
• R 7 , R 8 independently of one another are hydrogen, halogen, Ci-C ß- alkyl or Ci-Cg-haloalkyl; -
• R 9 is hydrogen, halogen, Ci-Cg-alkyl, -C-C 6 alkoxy,
• the invention also relates to processes and intermediates for the preparation of these compounds and their use for
• 2-pyridyl-4-aminopyrimidine derivatives with fungicidal activity are known from EP-A 407 899
• pyridylpyrimidine derivatives are known from DE-A 39 37 284, DE-A 39 37 285, DE-A 40 29 649, DE- A 40 34 762, DE-A 42 27 811, EP-A 481 405 and WO-A 92/10490.
• This reaction is usually carried out at 0 to 150 ° C, preferably 'from 20 to 120 ° C [cf. J. Chem. Res. S (7), pp. 286-287 (1995), Liebigs Ann. Chem., Pp. 1703-1705 (19.95)] in an inert solvent, optionally in the presence of an auxiliary base.
• Protic solvents such as alcohols, for example ethanol, or aprotic solvents, such as aromatic hydrocarbons or ethers, for example toluene, o-, m- and p-xylene, diethyl ether, diisopropyl ether, are used as solvents.
• aprotic solvents such as aromatic hydrocarbons or ethers, for example toluene, o-, m- and p-xylene, diethyl ether, diisopropyl ether
• solvents for example toluene, o-, m- and p-xylene, diethyl ether, diisopropyl ether
• auxiliary bases are those mentioned below: NaHC0 3 , Na 2 C0 3 , Na 2 HP0 4 , NaB0 7 , diethylaniline or ethyldiisopropylamine.
• the components are usually used in an approximately stoichiometric ratio. However, it may be advantageous to use the amine in excess.
• the amines of the formula VII are commercially available or known from the literature or can be prepared by known methods.
• the thio compounds VIII are oxidized to the sulfones of the formula IX.
• the reaction is usually carried out at 0 to 100 ° C., preferably at 10 to 50 ° C. in the presence of protic or aproptical solvents [cf. B. Cor. Chem. Soc.,. Vol. 16, pp. 489-492 (1995); Z. Chem., Vol. 17, p. 63 (1977)].
• Suitable solvents are alkyl carboxylic acids such as acetic acid or alcohols such as methanol, water or halogenated hydrocarbons such as dichloromethane or chloroform. Mixtures of these solvents can also be used. Acetic acid and a methanol / water mixture are preferred.
• Suitable oxidizing agents are, for example, hydrogen peroxide, tungstic acid, peracetic acid, 3-chloroperbenzoic acid, perphthalic acid, chlorine, oxygen and oxones (KHSO 5 ). The oxidizing agent is usually used in an approximately stoichiometric ratio. However, it can be advantageous to work with excess oxidant.
• the reaction is usually carried out in the presence of a base which can be used in equimolar amounts or in excess.
• bases come alkali metal carbonates and hydrogen carbonates, for example Na 2 CO 3 and NaHCO, nitrogen bases such as triethylamine, tributylamine and pyridine, alkali metal alcoholates such as sodium ethylate or potassium tert. butylate, alkali metal amides such as NaNH or alkali metal hydrides such as LiH or NaH.
• the reaction will usually be carried out at 50 to 250 ° C, preferably at 100 to 200 ° C in the presence of an inert solvent [see: Austr. J. Chem., Vol. 32, pp. 669-679 (1979); J. Org. Chem., Vol. 58, pp. 3785-3786 (1993); Poor. Xi. ZH, vol. 38, Nil, 718-719 (1985)].
• Suitable solvents are: protic solvents, such as alcohols, preferably methanol or ethanol, or aprotic solvents, such as tributylamine or ethylene glycol dimethyl ether.
• the components are usually used in approximately stoichiometric amounts. However, it can also be advantageous to use one of the components in excess.
• Haloalkyl straight-chain or branched alkyl groups with 1 to 8 carbon atoms (as mentioned above), where in these groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, for example C ⁇ -C 2 -haloalkyl such as chloromethyl, bromomethyl ,.
• Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 4, 6 or 8 carbon atoms and a double bond in any position, for example C 2 -Cg-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl , 2-butenyl, 3-butenyl, ' 1-methyl-l-propenyl, 2-methyl-l-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-l-butenyl, 2-methyl-l-butenyl, 3-methyl-l-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3- Methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-buten
• Alkynyl straight-chain or branched hydrocarbon groups with 2 to 4, 6 or 8 carbon atoms and a triple bond in any position, e.g. C-Cg-alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-l-butynyl, 1, l-dimethyl-2-propynyl, l-ethyl- 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl
• Cycloalkyl monocyclic, saturated hydrocarbon groups with 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;
• Sulfur atoms for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolididinyl, 3-isothiazolidinyl -Isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-0xazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4 -Imidazolidinyl, l, 2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin
• 5-ring heteroaryl groups which, in addition to carbon dioxide atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member can be bridged by a buta-1, 3-diene-1, - diyl group in which one or two carbon atoms have been replaced by nitrogen atoms can;
• 5-ring heteroaryl groups which in addition to carbon atoms can contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member by one
• R 1 is a five- or six-membered, in particular a five-membered, heterocycle.
• R 1 is a heterocycle which is bonded to the pyrimidine ring via nitrogen.
• R 1 represents the following groups: pyrrole, pyrazole, imidazole, 1, 2, 4-triazole, 1,2,3-triazole, tetrazole, 1,2, 3-triazine, 1,2 , 4-triazine, oxazole, isoxazole, 1, 3, 4-0xadiazol, furan, thiophene, thiazole, isothiazole, where the heterocycle can be bonded to the pyrimidine ring via C or N.
• cycle R 1 is pyridazine, pyrimidine or pyrazine, in particular 2-pyrimidine.
• R 1 is pyrazole, pyrrole, imidazole, 1, 2, 3-triazole, 1,2, 4-triazole, tetrazole, 2, optionally substituted by up to three groups R a or R a ' -Pyridine, 2-pyrimidine, pyrazine or 3-pyridazine.
• R 1 is pyrazole, 1, 2, 3-triazole or 1, 2, -triazole, in particular 1-pyrazole, are particularly preferred.
• compounds I are particularly preferred, in which R 2 represents halogen, C ⁇ -Cg-alkyl or C ⁇ -Cg-alkoxy, in particular halogen.
• R 3 and R 4 independently of one another are C ⁇ -Cg-alkyl, C ⁇ -Cg-haloalkyl, C 3 -C 6 cycloalkyl, C 2 -C 3 alkenyl.
• R 7 and R 8 are identical or different and are hydrogen or halogen.
• Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines
• Blumeria graminis (powdery mildew) on cereals, Fusarium and Verticillium species on various plants, Helminthosporium species on 'cereals, Mycosphaerella species on bananas and peanuts, Phytophthora infestans on potatoes and tomatoes, Plas opara viticola on grapevines, Podosphaera leucotricha on apples,
• the compounds I are also suitable for combating harmful fungi such as Paecilomyces variotii in the protection of materials (for example 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 fungicidal amount of the active compounds.
• the application can be both before and. also after the infection of the materials, plants or seeds by the fungi.
• the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
• active ingredient 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.
• the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.
• the formulations are prepared in a known manner, for example by stretching the active ingredient.
• Solvents and / or carriers if desired using emulsifiers and dispersants, where in the case of water as a diluent other organic solvents can also be used as auxiliary solvents.
• auxiliary substances for essentially considered: solvents such as aro aten (eg xylene) .
• chlorinated aromatics eg chlorobenzenes
• paraffins eg petroleum fractions
• alcohols eg methanol, butanol
• ketones eg cyclohexanone
• amine eg ethanolamine, dimethylformamide
• Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates);
• Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
• surfactants are alkali metal, Ammorii- salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic sulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, - fatty alcohol sulfates and fatty acids and alkali and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ethers, condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether,
• Coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polar solvents, e.g. Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water.
• Benzene toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives
• methanol ethanol
• propanol butanol
• chloroform carbon tetrachloride
• a compound of the invention are in. a mixture dissolved from 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mol of oleic acid-N-monoethanolamide, 2 parts by weight of calcium salt 'of dodecylbenzenesulfonic acid and 2 parts by weight of Addition product of 40 moles of ethylene oxide with 1 mole of castor oil (active ingredient content 9% by weight).
• VIII.20 parts by weight of a compound according to the invention are mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene- ⁇ -sulfonic acid, 17 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel well mixed and ground in a hammer mill.
• a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
• 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 existing concentrates are produced, which are suitable for dilution with water.
• the active substance concentrations in the ready-to-use preparations can be varied in larger ranges. 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, for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
• other active compounds for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
• Mixing the compounds I or the compositions comprising them in the use form 'as a fun gizide with other fungicides are obtained in many cases in an expansion of the fungicidal spectrum of action.
• Nitroderivate such as dinitro- (1-methylheptyl) phenylcrotonate, 2-sec-butyl-4, 6-dinitrophenyl-3, 3-dimethylacrylate, 2-sec-butyl-4, 6-dinitrophenyl-isopropyl carbonate, 5- Nitro-isophthalic acid-di-isopropyl ester;
• Phenylpyrroles such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyr-5-rol-3-carbonitrile,.
• Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3, 4-dimethoxyphenyl) acrylic morpholide,
• fungicides such as dodecylguanidine acetate, 3- [3- (3, 5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide,
• Example 1 from 64.8 g of the product from stage a after chromatography ah silica gel with cyclohexane, 43 g of white crystals of mp. 75 ° C. were obtained.
• stage e Analogously to Example 1 (stage e), from 89.8 mg of imidazole and 249.5 mg of the sulfone from Example 1, stage d, 0.22 g (91% of theory) of the title compound in the form of colorless crystals of mp . 172-173 ° C.
• the lipophilicity parameters logP ow (Table I) were determined in accordance with the OECD test guideline using the RP-HPLC runtime method.
• a logk '/ logP ow correlation curve was created based on ten reference substances and validated with the aid of the lipophilicity parameters of eight comparison substances determined by the extraction method.
• Example of use 4 Activity against Botrytis cinerea on paprika leaves
• aqueous active ingredient preparation which was prepared from a stock solution consisting of 10% active ingredient, 85% cyclohexanone and 5% emulsifier. 20 hours after the spray coating had dried on, the plants were inoculated with an aqueous spore suspension of cucumber mildew (Sphaerotheca fuliginea). The plants were then cultivated in a greenhouse at temperatures between 20 and 24 ° C. and 60 to 80% relative atmospheric humidity for 7 days. The extent of mildew development would then be determined visually in% of the cotyledon area.

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

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