EP1343785A2 - Verwendung von substituierten imidazoazinen, neue imidazoazine, verfahren zu deren herstellung, sowie sie enthaltende mittel - Google Patents
Verwendung von substituierten imidazoazinen, neue imidazoazine, verfahren zu deren herstellung, sowie sie enthaltende mittelInfo
- Publication number
- EP1343785A2 EP1343785A2 EP01994779A EP01994779A EP1343785A2 EP 1343785 A2 EP1343785 A2 EP 1343785A2 EP 01994779 A EP01994779 A EP 01994779A EP 01994779 A EP01994779 A EP 01994779A EP 1343785 A2 EP1343785 A2 EP 1343785A2
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- EP
- European Patent Office
- Prior art keywords
- formula
- compounds
- alkyl
- atoms
- radicals
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
- the present invention relates to the use of substituted imidazoazines of the formula I,
- hydrocarbon radicals are unsubstituted or partially or fully halogenated or can carry one to five identical or different groups R a
- R a halogen, cyano, nitro, hydroxy, Ci-Cö-alkyl, Ci-C ß -halo-alkyl, Ci-C ⁇ -alkylcarbonyl, C 3 -C 6 cycloalkyl, Ci-C ⁇ -alkoxy, C ⁇ - C6-haloalkoxy, C -C ⁇ alkoxycarbonyl, Ci-C ⁇ -alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, C 2 -Cg -alkenyl, C 3 -C 6 -alkenyloxy , C 3 -Cg-alkynyloxy or C ⁇ -C 4 -alkylene dioxy, which can be halogenated,
- 5- or 6-membered hetaryl or 5- or 6-membered heterocyclyl containing one to three N atoms and / or one 0 or S atom or one or two 0 and / or S atoms, or
- R b wherein the ring systems are unsubstituted or substituted by one to three radicals R b : R b cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, hydroxy, Ci-C ß- alkyl, Ci-Cg-haloalkyl, CC 6 -alkenyl, C -C 6 -halogenalkenyl, C -C 6 -alkynyl, C - C 6 ⁇ haloalkynyl, C ⁇ -C 6 -alkylcarbonyl, Ci-C ⁇ -alkyl-sulfonyl, C ⁇ -C 6 -alkylsulfoxyl, C -C 6 -cycloalkyl,
- R c cyano, nitro, halogen, hydroxy, amino, aminocarbonyl, aminothiocarbonyl, Ci-C ß- alkyl, Ci-C ⁇ -haloalkyl, C -C 6 alkylsulfonyl, C ⁇ -C 6 alkylsulfoxyl, C 3 -C 6 cyclo - Alkyl, Ci-Cg-Al oy, Ci-C ß -haloalkoxy, Ci-C ⁇ -alkoxycarbonyl, -C-C 6 -alkylthio, C ⁇ -C 6 -alkylamino, di-C ⁇ -C 6 -alkylamino, Ci -C ⁇ -alkylaminocarbonyl, di-Ci-Cö-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, CC 6 ⁇ A1- keny
- R 2 , R 3 independently of one another are hydrogen, -CC-alkyl
- R 2 , R 3 together with the bridging N atom is a 5- or
- Form 6-membered heterocyclic or heteroaromatic ring which can be interrupted by one to three N atoms and / or one 0 or S atom or one or two 0 and / or S atoms which is interrupted by one or two groups R b can be substituted; wherein the cyclic radicals R 2 and / or R 3 can be substituted by one to four groups R c ;
- A, B independently of one another N or CR 4 ;
- R 4, R 5, R 6 are independently hydrogen, halogen, cyano, nitro, hydroxy, C ⁇ -C 6 -alkyl, C 6 haloalkyl, C 3 -C 6 cloalkyl -Cy-, Ci-Cg-alkoxy, C ⁇ -C 6 -haloalkoxy, Ci-C ⁇ -alkylthio, amino, Ci-Cg-alkylamino, di-Ci-C ß -alkylamino, C -C 6 -alkenyl, C 3 -C 6 -alkenyloxy, C 2 -C 6 alkynyl or
- the invention also relates to new imidazoazines and processes for their production.
- Substituted imidazoazines with herbicidal activity are known from WO-A 94/18198, EP-A 166 609 and DE-A 41 20 108.
- Fungicidal imidazoazines are known from EP-A 404 190.
- the object of the present invention was therefore to find compounds with improved activity.
- substituted imidazoazines of the formula I has been found as a fungicide.
- new imidazoazines, agents containing them and processes for their preparation have been found.
- the compounds of formula I can be obtained in various synthetic routes.
- the imidazoazines of the formula I can be obtained from halogen derivatives of the formula V by reaction with an amine of the formula VI.
- Amino compounds of the formula II are reacted with aldehydes of the formula III and isonitriles of the formula IV to give imidazoazines of the formula I.
- This reaction usually takes place at temperatures from -10 ° C. to 200 ° C., preferably 15 ° C. to 30 ° C., in an inert organic solvent in the presence of a catalyst [cf. Tetrahedron Lett. 1998, p. 3635].
- Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.
- Inorganic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids such as boron trifluoride, aluminum trichloride, iron-III-chloride, tin-IV-chloride, titanium-IV-chloride and zinc are found as acids and acidic catalysts II chloride, and organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, toluenesulfonic acid, Use of benzenesulfonic acid, camphorsulfonic acid, citric acid and trifluoroacetic acid.
- the acids are generally used in catalytic amounts, but they can also be used in equimolar amounts, in excess or, if appropriate, as a solvent.
- Transition metal salts preferably from subgroup 3, are particularly suitable as catalysts.
- Lanthanum (III) compounds and scandium (III) salts are preferred. Since the catalytically active species is the transition metal cation, the choice of the anion is of little importance. For practical reasons, halides or organic radicals such as triflate, mesylate or acetate are preferred.
- the starting materials are generally reacted with one another in equimolar amounts. It can be advantageous for the yield to use III and IV in an excess based on II.
- the isonitriles of the formula IV can be synthesized, for example, from amines of the formula VI.
- the amines are prepared using known methods using alkyl formates VII, advantageously with acid catalysis [cf. Heterocycles 1990, p. 1287], to formamides of the formula VIII, which are then dehydrated with P0C1 3 with the addition of a base such as pyridine, to isonitriles IV [cf. Org. Syth. Coll. Vol. V, 300].
- isomer mixtures are obtained in the synthesis, however, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the action of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.
- Halogen fluorine, chlorine, bromine and iodine
- Alkyl saturated, straight-chain or branched hydrocarbon radicals with 1 to 4, 6, 8 or 10 carbon atoms, for example C 1 -C 6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl,
- Haloalkyl straight-chain or branched alkyl groups with 1 to 10 carbon atoms (as mentioned above), it being possible for part or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl , Fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-di-fluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2 -fluoroethyl, 2-chlorine- 2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trich
- Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 4, 6, 8 or 10 carbon atoms and a double bond in any position, for example C -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, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, l-di
- Halogenalk ⁇ nyl unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 10 carbon atoms and a double bond in any position (as mentioned above), the hydrogen atoms in these groups being partially or completely against halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, can be replaced;
- Alkynyl straight-chain or branched hydrocarbon groups with 2 to 4, 6, 8 or 10 carbon atoms and a triple bond in any position, for example C 2 -C 6 -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- Butynyl, 3-butynyl, l-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-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, l
- Haloalkynyl unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 10 carbon atoms and a triple bond in any position (as mentioned above), the hydrogen atoms in these groups being partially or completely against halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, can be replaced;
- Cycloalkyl monocyclic, saturated hydrocarbon groups with 3 to 6, 7, 8, 10 or 12 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, in addition to carbon ring members, one to three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, e.g. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-5-isothiaziazole nyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-0xazolidinyl, 4-0xazolidinyl, 5-0xazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl,
- Condensed 8 to 12-membered heterocyclyl containing one to four nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms: saturated or partially unsaturated 5- or 6-ring heterocyclyl groups, which in addition to carbon atoms can contain one to four nitrogen atoms or one to three nitrogen atoms and a 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-1,4-diyl group, which can be interrupted by one or two nitrogen atoms;
- Aryl a mono- to trinuclear aromatic ring system containing 6 to 14 carbon ring members, e.g. Phenyl, naphthyl and anthracenyl;
- 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, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members can, e.g.
- 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, for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl , 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3, 5-triazin-2-yl and 1,2, 4-triazin-3-yl;
- Condensed 8 to 12-membered heteroaryl containing one to four nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms: 5- or 6-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one can contain up to three nitrogen atoms and one sulfur or oxygen atom as ring members, and in which two adjacent carbon ring members or one nitrogen and one adjacent carbon ring member can be bridged by a buta-1, 3-diene-1,4-diyl group, which can be bridged by a or two nitrogen atoms can be interrupted;
- Alkylene divalent unbranched chains from 3 to 5 CH groups, for example CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 and CH 2 CH 2 CH 2 CH 2 CH 2 ;
- R 1 is phenyl substituted by one to five groups R b .
- compounds I are particularly preferred in which A and B are nitrogen or CH.
- R 1 is phenyl, benzyl and naphthyl are particularly preferred, it being possible for these groups to carry one to five substituents which are selected from the following group: halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C -alkoxy, C -Al- alkylthio, C ⁇ -C4 haloalkyl, C ⁇ -C4-haloalkoxy, C] .- C -Halogenal- alkylthio, C ⁇ -C 4 alkylcarbonyl, C ⁇ -C 4 -alkoxycarbonyl , Di- (C ⁇ -C-alkyl) amino, phenyl, phenoxy, benzyloxy, where the cyclic substituents can optionally be substituted by halogen, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl.
- R 1 is unsubstituted or 5- or 6-membered heteroaryl which is substituted by up to three R groups and contains one to three N atoms and / or one 0 or S atom or one or two 0 and / or S atoms.
- R 1 is 6-membered heteroaryl which is unsubstituted or substituted by up to three radicals R b and contains one to three N atoms and / or a 0 or S atom or one or two 0 and / or S atoms.
- R 1 is unsubstituted or substituted by up to three radicals R b, condensed heteroaryl containing an N atom.
- R 1 is unsubstituted or substituted by up to three R b phenyl, naphthyl, quinolinyl, isoquinolinyl, pyrimidinyl, pyridinyl, thiophenyl, pyrazolyl, pyrrolyl and furyl are also particularly preferred.
- R 2 is C 6 -C 6 -alkyl and Cs-Cg-cycloalkyl.
- R b is halogen, cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylamino , C 1 -C 4 alkylamino and C 1 -C 4 alkylthio.
- Table 79 Compounds of the formula I.2 in which A and B are CH, R 2 is hydrogen and R 3 is (S) -1, 1, 1-trifluoroprop-2-yl and the combination of the radicals R a is in each case a compound corresponds to one row of table A.
- Table 86 Compounds of the formula 1.2, in which A is N, B is CH, R 2 is hydrogen and R 3 is (S) -2, 2-dimethylbut-3-yl and the combination of the radicals R for each compound is one Row of table A corresponds
- Naphth-1-yl, R 5 and R 6 for hydrogen and the combination of the radicals R 2 and R 3 for a compound corresponds in each case to one line of Table B.
- the compounds I are suitable as fungicides. They are characterized by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides.
- Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines, Corynespora cassiicola on cucumbers, Colletotrichum species on fruits and vegetables, Diplocarpon rosae on roses, Elsinoe fawcetti and Diaporthe citri on citrus fruits, Sphaerotheca species on pumpkin plants, strawberries and roses, Cercospora species on peanuts, sugar beets and eggplants, Erysiphe cichoracearum on pumpkin plants, Leveillula taurica on bell peppers, tomatoes and aubergines, Myanelle and eggplant varieties Japanese apricot, Phyllactinia kakicola, Gloesporium kaki, on Japanese apricot, Gymnosporangium yamadae, Leptothyrium pomi, Podosphaera leucotricha and Gloedes pomigena on apples,
- Rhizoctonia species on cotton, rice and lawn Stagonospora nodorum and Septoria tritici on wheat, Uncinula necator on vines, • Ustilago species on cereals and sugar cane, and Venturia species (scab) on apples and pears.
- the compounds I are also suitable for combating harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
- harmful fungi such as Paecilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
- the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds.
- the application can take place both before and after the infection of the materials, plants or seeds by the fungi.
- the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
- the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
- active ingredient 0.001 to 0.1 g, preferably 0.01 to 0.05 g, per kg of seed are generally required.
- the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably
- the compounds I can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
- the form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the compound according to the invention.
- the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, where, in the case of water as the diluent, other organic solvents can also be used as auxiliary solvents.
- auxiliaries solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g.
- Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
- Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, silicates)
- Emulsifiers such as non-ionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
- Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid sulfates, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids and their alkali and alkaline earth metal salts, salts of sulfated fatty alcohol glycol ethers, condensates of sulfonated Naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol
- Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
- Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
- Solid carriers are e.g. Mineral soils, such as silicas, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
- Mineral soils such as silicas, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastic
- the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient.
- the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum). Examples of formulations are:
- V. 80 parts by weight of a compound according to the invention are mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel well mixed and ground in a hammer mill (active ingredient content 80% by weight).
- VIII.20 parts by weight of a compound according to the invention are pulverized 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. deformed silica gel well mixed and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
- the active ingredients as such in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring.
- 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.
- concentrates composed of an active substance, wetting agents, adhesives, dispersants or emulsifiers and possibly solvents or oil, which are suitable for dilution with water.
- the active substance concentrations in the ready-to-use preparations can be varied over a wide range. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
- the active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
- UUV ultra-low-volume process
- Oils of various types, herbicides, fungicides, other pesticides, bactericides can be added to the active ingredients, if appropriate also only immediately before use (tank mix). be set. These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
- the agents according to the invention can also be present in the use form as fungicides together with other active ingredients, which e.g. with herbicides, insecticides, growth regulators, fungicides or even with fertilizers. Mixing the compounds I or the compositions containing them in the use form as fungicides with other fungicides results in an enlargement of the fungicidal spectrum of action in many cases.
- Sulfur, dithiocarbamates and their derivatives such as ferridimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese zinc ethylenediamine bis dithiocarbamate, tetramethylthiurondarbamethyne damidulfide, , Ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate), zinc (N, N'-propylene-bis-dithiocarbamate), N, N'-polypropylene-bis- (thiocarbamoyl) disulfide;
- Nitroderivate such as dinitro- (1-methylheptyl) phenylcrotonate, 2-sec-butyl-4, 6-dinitrophenyl-3, 3-dimethylacrylate, 2-sec-butyl-4, 6-dinitrophenyl-isopropyl carbonate, 5- Nitro-isophthalic acid-di-isopropyl ester;
- Heterocyclic substances such as 2-heptadecyl-2-imidazoline acetate, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, 0,0-diethyl-phthalimidophosphonothioate, 5-amino-l- [ bis- (dimethylamino) phosphinyl] -3-phenyl-l, 2, 4-triazole, 2, 3-dicyano-l, 4-di-thioanthraquinone, 2-thio-l, 3-dithiolo [4, 5 -b] Quinoxaline, 1- (butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester, 2-methoxycarbonylamino-benzimidazole, 2- (furyl- (2)) -benzimidazole, 2- (thiazolyl- (4)) -benzimidazole, N. - (1, 1, 2, 2-tetrachloro
- Strobilurins such as methyl-E-methoxyimino- [ ⁇ - (o-tolyloxy) -o-tolyl] acetate, methyl-E-2- ⁇ 2- [6- (2-cyanophenoxy) pyrimidin-4-yl- oxy] -phenyl ⁇ -3-methoxyacrylate, methyl-E-methoxyimino- [ ⁇ - (2-phenoxyphenyl)] acetamide, methyl-E-methoxyimino- [ ⁇ - (2,5-dimethylphenoxy) -o-tolyl ] -acetamide, methyl-E-2- ⁇ 2- [2-trifluoromethyl-pyridyl-6-] oxymethyl] phenyl ⁇ 3-methoxyacrylate, (E, E) -methoximino- ⁇ 2- [1- (3rd -trifluoromethylphenyl) -ethylideneaminooxy-methyl] -phenyl ⁇
- Anilinopyrimidines such as N- (4, 6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- [4-Me- thyl-6-cyclopropyl-pyrimidin-2-yl] aniline, phenylpyrroles such as 4- (2, 2-difluoro-l, 3-benzodioxol-4-yl) pyrrole-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,
- the active ingredients were separated or together as a 10% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight .-% Wettol® EM (non-ionic emulsifier based on ethoxylated castor oil) prepared and diluted with water according to the desired concentration.
- Nekanil® LN Litensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
- .-% Wettol® EM non-ionic emulsifier based on ethoxylated castor oil
- Leaves of potted plants of the "large meat tomato St. Pierre" were sprayed to runoff point with an aqueous suspension which was prepared from a stock solution of 10% active ingredient, 63% cyclohexanone and 27% emulsifier. The following day, the leaves were infected with an aqueous zoo spore suspension of Alternaria solani in 2% biomalt solution with a density of 0.17 x 10 6 spores / ml. The plants were then placed in a steam-saturated chamber at temperatures between 20 and 22 ° C. After 5 days, the blight on the untreated but infected control plants had developed so strongly that the infestation could be determined visually in%.
- Leaves of potted vines of the "Müller-Thurgau" variety were sprayed to runoff point with aqueous preparation of active compound, which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier.
- aqueous preparation of active compound which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier.
- the following day, the undersides of the leaves were inoculated with an aqueous zoospore suspension of Plasmopara viticola.
- the vines were then placed for 48 hours in a steam-saturated chamber at 24 ° C and then for 5 days in a greenhouse at temperatures between 20 and 30 ° C. After this time, the plants were again placed in a moist chamber for 16 hours in order to accelerate the sporangium carrier outbreak. Then was the extent of the development of the infestation on the undersides of the leaves was determined visually.
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10061983 | 2000-12-13 | ||
DE10061983 | 2000-12-13 | ||
PCT/EP2001/014577 WO2002048146A2 (de) | 2000-12-13 | 2001-12-12 | Verwendung von substituierten imidazoazinen, neue imidazoazine, verfahren zu deren herstellung, sowie sie enthaltende mittel |
Publications (1)
Publication Number | Publication Date |
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EP1343785A2 true EP1343785A2 (de) | 2003-09-17 |
Family
ID=7666908
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01994779A Withdrawn EP1343785A2 (de) | 2000-12-13 | 2001-12-12 | Verwendung von substituierten imidazoazinen, neue imidazoazine, verfahren zu deren herstellung, sowie sie enthaltende mittel |
Country Status (4)
Country | Link |
---|---|
US (1) | US20040058938A1 (de) |
EP (1) | EP1343785A2 (de) |
AU (1) | AU2002224927A1 (de) |
WO (1) | WO2002048146A2 (de) |
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WO2010032195A1 (en) * | 2008-09-16 | 2010-03-25 | Csir | Imidazopyridines and imidazopyrimidines as hiv-i reverse transcriptase inhibitors |
CA2778949C (en) | 2009-10-30 | 2018-02-27 | Janssen Pharmaceutica Nv | Imidazo[1,2-b]pyridazine derivatives and their use as pde10 inhibitors |
AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
CN103619846B (zh) | 2011-06-27 | 2016-08-17 | 詹森药业有限公司 | 1-芳基-4-甲基-[1,2,4]三唑[4,3-a]喹喔啉衍生物 |
JP6426603B2 (ja) | 2012-06-26 | 2018-11-21 | ヤンセン ファーマシューティカ エヌ.ベー. | 神経障害または代謝障害の治療に使用するための、1−アリール−4−メチル−[1,2,4]トリアゾロ[4,3−a]−キノキサリン化合物などのPDE2阻害剤とPDE10阻害剤との組合せ |
EP2869822B1 (de) | 2012-07-09 | 2016-09-14 | Janssen Pharmaceutica, N.V. | Hemmer des phosphodiesterase-10-enzyms |
BR112015010469A2 (pt) * | 2012-11-14 | 2017-07-11 | Hoffmann La Roche | derivados de imidazopiridina |
WO2015123437A1 (en) | 2014-02-13 | 2015-08-20 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
MX2016010395A (es) | 2014-02-13 | 2017-02-28 | Incyte Corp | Ciclopropilamina como inhibidor de la desmetilasa 1 especifica de lisinas (lsd1). |
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TW201613860A (en) | 2014-02-13 | 2016-04-16 | Incyte Corp | Cyclopropylamines as LSD1 inhibitors |
WO2016007731A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Imidazopyridines and imidazopyrazines as lsd1 inhibitors |
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WO2016007727A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
CR20170500A (es) | 2015-04-03 | 2018-02-02 | Incyte Corp | Compuestos heterocíclicos como inhibidores de lsd1 |
TWI765860B (zh) | 2015-08-12 | 2022-06-01 | 美商英塞特公司 | Lsd1抑制劑之鹽 |
WO2017070089A1 (en) | 2015-10-19 | 2017-04-27 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
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SG10202010414QA (en) | 2016-04-22 | 2020-11-27 | Incyte Corp | Formulations of an lsd1 inhibitor |
AR108396A1 (es) | 2016-05-06 | 2018-08-15 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
ES2905980T3 (es) | 2016-05-26 | 2022-04-12 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
LT3472167T (lt) | 2016-06-20 | 2022-11-10 | Incyte Corporation | Heterocikliniai junginiai kaip imunomoduliatoriai |
US20180016260A1 (en) | 2016-07-14 | 2018-01-18 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
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CR20190317A (es) | 2016-12-22 | 2019-09-13 | Incyte Corp | Compuestos inmunomodulares y métodos de uso |
US20180179179A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
EP3692052A4 (de) * | 2017-10-04 | 2021-03-17 | Dana Farber Cancer Institute, Inc. | Kleinmolekülhemmung von transkriptionsfaktors sall4 und verwendungen davon |
PT3774791T (pt) | 2018-03-30 | 2023-03-03 | Incyte Corp | Compostos heterocíclicos como imunomoduladores |
SI3790877T1 (sl) | 2018-05-11 | 2023-06-30 | Incyte Corporation | Tetrahidro-imidazo(4,5-c)piridinski derivati kot imunomodulatorji pd-l1 |
CN108794471B (zh) * | 2018-08-27 | 2020-04-28 | 青岛农业大学 | 苯并咪唑类化合物的合成方法及其农用生物活性 |
US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
CA3150434A1 (en) | 2019-08-09 | 2021-02-18 | Incyte Corporation | Salts of a pd-1/pd-l1 inhibitor |
PE20221038A1 (es) | 2019-09-30 | 2022-06-17 | Incyte Corp | Compuestos de pirido[3,2-d] pirimidina como inmunomoduladores |
AU2020385113A1 (en) | 2019-11-11 | 2022-05-19 | Incyte Corporation | Salts and crystalline forms of a PD-1/PD-L1 inhibitor |
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DE3533050A1 (de) * | 1985-09-17 | 1987-03-26 | Basf Ag | 7-amino-azolo(1,5-a)pyrimidine, verfahren zu ihrer herstellung und diese enthaltende fungizide, bzw. deren verwendung als fungizide |
DE19948434A1 (de) * | 1999-10-08 | 2001-06-07 | Gruenenthal Gmbh | Substanzbibliothek enthaltend bicyclische Imidazo-5-amine und/oder bicyclische Imidazo-3-amine |
PT1218382E (pt) * | 1999-10-08 | 2004-06-30 | Gruenenthal Gmbh | Derivados de imidazo-3-il-amina biciclica |
MXPA02003547A (es) * | 1999-10-08 | 2002-09-18 | Gr Nenthal Gmbh | Derivados biciclos de imidazo-3-il-amina substituidos en el sexto anillo. |
US6589952B2 (en) * | 2000-07-14 | 2003-07-08 | Bristol-Myers Squibb Pharma Company | Imidazo[1,2-a]pyrazines for the treatment of neurological disorders |
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2001
- 2001-12-12 WO PCT/EP2001/014577 patent/WO2002048146A2/de not_active Application Discontinuation
- 2001-12-12 EP EP01994779A patent/EP1343785A2/de not_active Withdrawn
- 2001-12-12 US US10/433,440 patent/US20040058938A1/en not_active Abandoned
- 2001-12-12 AU AU2002224927A patent/AU2002224927A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
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Also Published As
Publication number | Publication date |
---|---|
US20040058938A1 (en) | 2004-03-25 |
AU2002224927A1 (en) | 2002-06-24 |
WO2002048146A3 (de) | 2002-11-14 |
WO2002048146A2 (de) | 2002-06-20 |
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