Classifications

• • 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
  • C07D239/34—One oxygen 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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
• • 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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
  • C07C271/60—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups having oxygen atoms of carbamate groups bound to nitrogen atoms

Definitions

• the present invention relates to iminooxymethylene anilides of the formula I.
• n 0, 1, 2, 3 or 4, where the subsituents R can be different if n is greater than 1;
• Bridge which contains three to four members from the group of 3 or 4 carbon atoms, 2 or 3 carbon atoms and 1 or 2 nitrogen, oxygen and / or sulfur atoms, this bridge together with the ring to which it is attached one can form partially unsaturated or aromatic radical;
• X is a direct bond or CH 2 , 0 or NR a ;
• R a is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl;
• R 1 is hydrogen
• R alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, or, if X is R a , additionally hydrogen;
• R is hydrogen, cyano, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or cycloalkyl;
• R 4 is a 6- to 10-membered mono- or bicyclic, heteroaromatic ring system which is substituted by conventional groups,
• Anilides with fungicidal activity are known from WO-A 93 / 15,046.
• the present invention was based on active substances with improved effectiveness as an object.
• the compounds I can be obtained by various methods. Compounds I in which R 1 is not hydrogen are obtained particularly advantageously by reacting a methylene anilide of the formula II with an oxime of the formula III or its salt.
• L 1 in formula II stands for a leaving group, ie a nucleophilically exchangeable group such as halogen (eg chlorine, bromine and iodine), or an alkyl or aryl sulfonate (eg methyl sulfonate, trifluoromethyl sulfonate, phenyl sulfonate and 4-methylphenyl sulfonate).
• halogen eg chlorine, bromine and iodine
• alkyl or aryl sulfonate eg methyl sulfonate, trifluoromethyl sulfonate, phenyl sulfonate and 4-methylphenyl sulfonate.
• the oxides III can also be in the form of their salts, e.g. with inorganic acids such as hydrochloride, hydrobromide, hydrosulfate and hydrophosponate can be used.
• the reaction of the compounds II and III is usually carried out at temperatures from 0 ° C. to 80 ° C., preferably 20 ° C. to 60 ° C., in an inert solvent in the presence of a base.
• Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as dieethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and Propionitrile, alcohols such as methanol, ethanol, n-propanol, i-propanol, n-butanol and tert-butanol, ketones such as acetone and methyl ethyl ketone and dimethyl sul
• inorganic compounds such as alkali metal and alkaline earth metal hydroxides (for example lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide), alkali metal and alkaline earth metal oxides (for example lithium oxide, sodium oxide, calcium oxide and magnesium oxide), alkali metal and alkaline earth metal hydrides (for example lithium hydride) are generally used , Sodium hydride, potassium hydride and calcium hydride), alkali metal amides (for example lithium amide, sodium amide and potassium amide), alkali metal and alkaline earth metal carbonates (for example lithium carbonate and calcium carbonate) and alkali metal / hydrogen carbonates (for example sodium hydrogen carbonate), organometallic compounds, in particular alkali metal alkyls (for example methyl lithium) , Butyllithium and phenyllithium), alkylmagnesium halides (e.g.
• methylmagnesium chloride as well as alkali metal and alkaline earth metal alcoholates (e.g. sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butoxide and dimethoxy-magnesium), and also organic bases, e.g. Tertiary amines such as trimethylamine, triethylamine, tri-isopropylethyl in and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine, and bicyclic amines.
• alkali metal and alkaline earth metal alcoholates e.g. sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butoxide and dimethoxy-magnesium
• organic bases e.g. Tertiary amines such as trimethylamine, triethylamine, tri-isopropylethyl in and N-methylpiperidine, pyridine, substituted
• the bases are generally used in equimolar amounts, in excess or, if appropriate, as a solvent.
• reaction may be advantageous for the reaction to add a catalytic amount of a crown ether (e.g. 18-crown-6 or 15-crown-5).
• a catalytic amount of a crown ether e.g. 18-crown-6 or 15-crown-5.
• phase Transfer catalysts include, for example, ammonium halides and tetrafluoroborates (for example benzyltriethylammonium chloride, benzyltributylammonium bromide, tetrabutylammonium chloride, hexadecyltrimethylammonium bromide or tetrabutylammonium tetrafluoroborate) and phosphonium halylphosphonium (eg phosphonium halylphosphonium) and phosphonium halylphosphate (eg, phosphonium halomethyl) and phosphonium halomethonyl (eg phosphonium halomyl) and phosphonium halomyl chloride (eg.
• ammonium halides and tetrafluoroborates for example benzyltriethylammonium chloride, benzyltributylammonium bromide, tetrabutylam
• the starting materials II required for the preparation of the compounds I are known from WO-A 93 / 15,046 or can be prepared by the methods described therein.
• reaction may be advantageous for the reaction to first convert the oxime III or its salt with the base into the corresponding base, which is then reacted with the benzyl derivative II.
• the compounds I can contain acidic or basic centers and accordingly form acid addition products or base addition products or salts.
• Acids for acid addition products include Mineral acids (for example hydrohalic acids such as hydrochloric acid and hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid), organic acids (for example formic acid, acetic acid, oxalic acid, malonic acid, lactic acid, malic acid, succinic acid, tartaric acid, citric acid, pentic acid, pesticide) -Toluenesulfonic acid, dodecylbenzenesulfonic acid) or other proton acidic compounds (eg saccharin).
• Mineral acids for example hydrohalic acids such as hydrochloric acid and hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid
• organic acids for example formic acid, acetic acid, oxalic acid, malonic acid, lactic acid, malic acid, succinic acid, tartaric acid, citric acid, pentic acid, pesticide
• -Toluenesulfonic acid dodecylbenzenesul
• the compounds I in which R 1 is hydrogen can be obtained by converting a nitrobenzene IV with an oxime III into the corresponding oxime ether V, reducing V to hydroxylamine VI in a manner known per se and then VI with an acylating agent VIIa or with an isocyanate VIIb or with a cyanate VIIc to form I.
• L 2 in formula IV stands for a leaving group, ie for a nucleophilically exchangeable group such as halogen (eg chlorine, bromine and iodine), or an alkyl or aryl sulfonate (eg methyl sulfonate, trifluoromethyl sulfonate, phenyl sulfonate and 4-methylphenyl sulfonate).
• halogen eg chlorine, bromine and iodine
• alkyl or aryl sulfonate eg methyl sulfonate, trifluoromethyl sulfonate, phenyl sulfonate and 4-methylphenyl sulfonate.
• L 3 in the formula VIIa means halogen (for example chlorine, bromine and iodine), phenoxy or the group R 2 XCÜ 2 .
• M * in formula VIIc represents an equivalent of a metal ion (e.g. an alkali metal or alkaline earth metal ion such as sodium, potassium and calcium).
• a metal ion e.g. an alkali metal or alkaline earth metal ion such as sodium, potassium and calcium.
• the reaction of the benzyl compounds IV with the oxime III takes place in general and in particular according to the methods of the reaction of the benzyl compound II with the oximes III (see above).
• the nitroaromatics V are reduced to the hydroxylamines VI either with zinc (analogously to Bamberger et al., Am. Chem. 316 (1901), 278) or with hydrogen in the presence of suitable catalysts such as platinum (analogously to EP 85 890).
• the reaction of the hydroxylme VI with the carbonyl compounds VIII or VIIIb or the cyanate VIIc is preferably carried out under alkaline conditions at -40 to 60 ° C., preferably
• the compounds I in which R 1 is not hydrogen are prepared by reacting a compound of the formula I in which R 1 is hydrogen n in a manner known per se with a compound VIII.
• Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as dieethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and Propionitrile, alcohols such as methanol, ethanol, n-propanol, l-propanol, n-butanol and tert-butanol, ketones such as acetone and methyl ethyl ketone and also dimethyl sulfoxide, dimethylformamide, dimethylacetamide, 1,3-dim-methyl-dimazolide-2-one and 1 , 2-D ⁇ methyltetrahydro-2 (1H) - pyrimidm, preferably
• Inert solvents such as e.g. Toluene, methylene chloride, methyl t-butyl ether, autonitrile, cyclohexane, acetone, tetrahydrofuran, dimethylformamdi or N-methylpyrrolidone.
• Bases generally include inorganic compounds such as alkali metal and alkaline earth metal hydroxides (for example lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide), alkali metal and alkaline earth metal oxides (for example lithium oxide, sodium oxide, calcium oxide and magnesium oxide), alkali metal and alkaline earth metal hydrides (for example lithium hydride , Sodium hydride, potassium hydride and calcium hydride), alkali metal amides (e.g. lithium amide, sodium acid and potassium amide), alkali metal and alkaline earth metal carbonates (e.g. lithium carbonate and calcium carbonate) and alkali metal bicarbonates (e.g.
• alkali metal and alkaline earth metal hydroxides for example lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide
• alkali metal and alkaline earth metal oxides for example lithium oxide, sodium oxide, calcium oxide and magnesium oxide
• alkali metal and alkaline earth metal hydrides for example lithium
• organometallic compounds especially alkali metal alkyls (e.g. methyl lithium, butyllithium and phenyllithium), alkylmagnesium halides (e.g. methylmagnesium chloride) as well as alkali metal and alkaline earth metal alcoholates (e.g.
• Triethylamine, morpholine, ethyldiisopropylamine sodium hydroxide, potassium carbonate, potassium tert-butanoate, sodium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, potassium phosphate, dipotassium hydrogen phosphate or potassium dihydrogen phosphate are particularly preferred.
• the bases are generally used in equimolar amounts, in excess or, if appropriate, as a solvent.
• phase transcatalysts here are ammonium halides and tetrafluoroborates (e.g. benzyltriethylammonium chloride, benzyltributylammonium bromide, tetrabutylammonium chloride, hexadecyltrimethylammonium bromide or tetrabutylammonium tetrafluoroborate) and phosphonium phosphonium halide (e.g. phosphonium halonyl chloride) such as phosphonium halonyl chloride (e.g. phosphonium halide) and phosphonium halobutyl chloride.
• ammonium halides and tetrafluoroborates e.g. benzyltriethylammonium chloride, benzyltributylammonium bromide, tetrabutylammonium chloride, hexadecyltri
• L 4 in formula VIII stands for a leaving group, ie for a nucleophilically exchangeable group such as halogen (for example chlorine, bromine and iodine), phenoxy or an alkyl or aryl sulfonate (for example methyl sulfonate, trifluoromethyl sulfonate, phenyl sulfonate and 4-methylphenyl sulfonate ).
• halogen for example chlorine, bromine and iodine
• phenoxy or an alkyl or aryl sulfonate for example methyl sulfonate, trifluoromethyl sulfonate, phenyl sulfonate and 4-methylphenyl sulfonate ).
• the compounds I are also obtained by first converting a methylene anilide II into the benzyl ether X using N-hydroxyphthalimide (IX), X then hydrolyzing with ammonia, hydrazine or an amine or with acid catalysis to give the hydroxylamine ether XI and XI is then reacted with a carbonyl compound XII to I.
• N-hydroxyphthalimide IX
• X N-hydroxyphthalimide
• the conversion of the N-hydroxy-phthalimide ether XI to the benzyloxyamine XIa or its salts is carried out according to the methods described in EP 463 488.
• Mineral acids such as e.g. Hydrochloric acid, sulfuric acid, phosphoric acid or nitric acid, or also organic acids such as e.g. Formic acid, acetic acid, propionic acid, triethylamine hydrochloride, p-toluenesulfonic acid, methanesulfonic acid, citric acid or acidic ion exchanger.
• the compounds I in which X represents NR a are obtained , for example, by first converting a methylene anilide of the formula Ila with an oxime III into the corresponding oxime ether XIII and then reacting XIII to I with an amine XIV.
• L 1 in the formula Ila stands for a leaving group, ie for a nucleophilically exchangeable group such as halogen (for example chlorine, bromine and iodine), or an alkyl or aryl sulfonate (for example methyl sulfonate, trifluoromethyl sulfonate, phenyl sulfonate and 4-methylphenyl sulfonate).
• halogen for example chlorine, bromine and iodine
• alkyl or aryl sulfonate for example methyl sulfonate, trifluoromethyl sulfonate, phenyl sulfonate and 4-methylphenyl sulfonate.
• the reaction of the benzyl compounds Ila with the oximes III takes place in general and in particular according to the methods of the reaction of the benzyl compounds II with the oximes III.
• the reaction of the compounds XIII with the amines of the formula HNR a R 2 takes place at temperatures from 0 ° C. to 100 ° C. in an inert solvent or in a solvent mixture.
• Particularly suitable solvents are water, tert. Butyl methyl ether and toluene or mixtures thereof. It may be advantageous to add one of the following solvents (as solubilizer) to improve the solubility of the starting materials: tetrahydrofuran, methanol, dimethylformamide and ethylene glycol ether.
• the amines XIV are usually used in an excess of up to 100% based on the compounds XIII or can be used as solvents. With regard to the yield, it can be advantageous to carry out the reaction under pressure.
• Bases for base addition products include Oxides, hydroxides, carbonates or hydrogen carbonates of alkali metals or alkaline earth metals (e.g. potassium or sodium hydroxide or carbonate) or ammonium compounds (e.g. ammonium hydroxide).
• Acids for acid addition products include Mineral acids (eg hydrohalic acids such as hydrochloric acid and hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid), organic acids (eg formic acid, acetic acid, oxalic acid, malonic acid, lactic acid, malic acid, succinic acid, tartaric acid, hydrochloric acid, citric acid) -Toluenesulfonic acid, dodecylbenzenesulfonic acid) or other proton acidic compounds (eg saccharin).
• Mineral acids eg hydrohalic acids such as hydrochloric acid and hydrobromic acid, phosphoric acid, sulfuric acid, nitric acid
• organic acids eg formic acid, acetic acid, oxalic acid, malonic acid, lactic acid, malic acid, succinic acid, tartaric acid, hydrochloric acid, citric acid
• -Toluenesulfonic acid eg dodecylbenzen
• Halogen fluorine, chlorine, bromine and iodine
• Alkyl saturated, straight-chain or branched hydrocarbon radicals with preferably 1 to 10 carbon atoms, e.g. Methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1, 1-dimethylethyl;
• Haloalkyl straight-chain or branched alkyl groups with preferably 1 to 10 carbon atoms (as mentioned above), it being possible for some 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, Dichloroethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, Chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
• Alkylcarbonyl straight-chain or branched alkyl groups with preferably 1 to 10 carbon atoms (as mentioned above) which are bonded to the skeleton via a carbonyl group (-CO-);
• Alkoxy straight-chain or branched alkyl groups with preferably 1 to 10 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (-0-);
• Haloalkoxy straight-chain or branched haloalkyl groups with preferably 1 to 10 carbon atoms (as mentioned above), which are bonded to the skeleton via an oxygen atom (-0-);
• Alkoxycarbonyl straight-chain or branched alkoxy groups with preferably 1 to 10 carbon atoms (as mentioned above) which are bonded to the skeleton via a carbonyl group (-CO-);
• Alkylthio straight-chain or branched alkyl groups with preferably 1 to 10 carbon atoms (as mentioned above), which are bonded to the structure via a sulfur atom.
• Haloalkylthio straight-chain or branched haloalkyl groups with preferably 1 to 4 carbon atoms (as mentioned above), which are bonded to the skeleton via a sulfur atom (-S-);
• Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals with preferably 2 to 10 carbon atoms and a double bond in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl , 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3rd -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-dimethyl
• 3-methyl-1-pentenyl 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl yl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3 -Methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2 -Dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2 , 2-Di- mmeetthnyyl
• Alkenyloxy straight-chain or branched alkenyl groups with preferably 3 to 10 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (-0-);
• Alkynyl straight-chain or branched hydrocarbon groups with preferably 2 to 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, 3rd -Butinyl, l-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-hexyn
• Alkynyloxy straight-chain or branched alkynyl groups having front ⁇ preferably 3 to 10 carbon atoms (as mentioned above) which are bonded via an oxygen atom (-0-) to the backbone;
• Cycloalkyl mono- or bicyclic hydrocarbon residues with preferably 3 to 10 carbon atoms, for example C 3 -C 10 - (Bi) cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, bornanyl, norbornanyl, dicyclohexyl, bicyclo [3, 3, 0] octyl,
• Bicyclo [3, 3, l] nonyl Cycloalkenyl: mono- or bicyclic hydrocarbon radicals with preferably 5 to 10 carbon atoms and a double bond in any ring position, for example C 5 -C 10 - (Bi) cycloalkenyl such as cyclopentenyl, cyclohexenyl, cycloheptenyl, bornenyl, norbornenyl, dicyclohexenyl and bicyclo [3, 3 , 0loctenyl;
• a bridge bonded to two adjacent ring atoms which has three to four members from the group of 3 or 4 carbon atoms, 2 or 3 carbon atoms and 1 or 2 nitrogen, oxygen and / or sulfur atoms, this bridge together with the ring to which they are attached is bound, can form a partially unsaturated or aromatic radical: for example Bridges which, for example, form one of the following systems with the ring to which they are bound: quinolinyl, benzofuranyl and naphthyl;
• the heteroaromatic or heterocyclic radical can be attached via a carbon atom or a nitrogen atom of the heteroaromatic or heterocyclic radical.
• 6-membered heteroaromatics which can additionally be benzo-condensed or fused to another 5- or 6-membered heteroaromatic ring system, e.g.
• 5- ⁇ lower heteroarvl. containing one to three nitrogen atoms 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, e.g. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-triazol-3-yl, 1,2, 3-triazolyl and 1, 3, 4-triazol-2-yl;
• 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 one Carbon ring member can be bridged by a buta-1, 3-diene-1,4-diyl group, these rings being bonded to the framework via one of the nitrogen ring members;
• banzo- or hatarokondenaiartaa 6-gliadrigaa heteroarvl. and containing one bia three or one to four Stickatoffatome and / or a Sauersto f or Sehwafalatomi 6-membered ring heteroaryl groups which, besides carbon atoms one to three Stick ⁇ atoms as ring members, may contain, and in which two adjacent carbon ring members or one Nitrogen and an adjacent carbon ring member by a buta-1,3-diene-l, 4-diyl group or a 3 to 4-membered unsaturated chain which, in addition to carbon members, for example nitrogen atoms and / or an oxygen or sulfur may contain atom, may be bridged, for example indolyl, quinolinyl, isoquinolinyl and purinyl.
• alkyl, alkenyl and alkynyl groups is intended to express that these groups can be partially or completely halogenated, ie that the hydrogen atoms of these groups are partially or completely replaced by identical or different halogen atoms such as above (preferably fluorine, chlorine or bromine) can be replaced and / or can carry one to three (preferably one) of the following radicals:
• Cyano, nitro, hydroxy, amino, formyl, carboxyl, aminocarbonyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alkoxycarbonylamino, alkylcarbonyl-carbonyl-N-carbonyl N-alkylamino, and CR- * 11 N0R 1V , where R 1 * - 1 is hydrogen, alkanyl, alkenyl, alkynyl or cycloalkyl and R 1V is alkyl, alkenyl, alkynyl or arylalkyl and the alkyl groups mentioned are preferably 1 up to 6 carbon atoms, in particular 1 to 4 carbon atoms, and the alkanyl or alky
• cycloalkyl unsubstituted or substituted by conventional groups cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino or heterocyclyl-N-alkylamino
• the cyclic systems preferably having 3 to 2 ring members, 3 to 2 ring members , in particular contain 3 to 6 ring members and the alkyl groups in these radicals preferably contain 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms;
• cyclic (saturated, unsaturated or aromatic) groups can be partially or completely halogenated, i.e. that the hydrogen atoms of these groups can be partially or completely replaced by identical or different halogen atoms as mentioned above (preferably fluorine, chlorine or bromine, in particular fluorine or chlorine), and / or one to four (in particular one to three) of the following radicals
• Cyano nitro, hydroxy, amino, carboxyl, aminocarbonyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkynyl, haloalkynyl, alkynyloxy, haloalkynyloxy, alkoxy,
• alkyl groups in these radicals preferably contain 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms and the alkenyl or alkynyl groups mentioned contain 2 to 8, preferably 2 to 6, in particular 2 to 4, carbon atoms in these radicals;
• cycloalkyl unsubstituted or substituted by conventional groups cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino or heterocyclyl-N-alkylamino
• the cyclic systems preferably 3 to 12 ring members, 3 to 12 ring members , in particular contain 3 to 6 ring members and the alkyl groups in these radicals preferably contain 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms;
• the aryl radicals preferably having 6 to 10 ring contain members, in particular 6 ring members (phenyl), the hetaryl residues in particular contain 5 or 6 ring members and the alkyl groups in these residues preferably contain 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms,
• C 3 -C alkylene, C 3 -C 5 alkenylene, oxy-C -C 4 alkylene, oxy-C ⁇ -C- ⁇ -alkyleneoxy, oxy-C 2 -C 4 -alkenylene, ⁇ xy-C: -C 4 -alkenyleneoxy or butadienediyl group, where these bridges can in turn be partially or completely halogenated and / or one to three , especially one or two can carry the following radicals: C 4 -alkyl, C haloalkyl, C, -C 4 alkoxy, C 4 haloalkoxy, and C *, - C 4 alkylthio.
• n 1
• R is one of the following groups: fluorine, chlorine, cyano, methyl and methoxy.
• compounds I are particularly preferred in which X is NH. Likewise, particular preference is given to compounds I in which x is CH 2 .
• R 1 is C 1 -C 4 -alkyl, in particular methyl.
• R 2 is C 1 -C 4 -alkyl, in particular methyl.
• R 3 is C 1 -C 4 -alkyl, in particular methyl.
• R 3 represents cyano, trifluoromethyl, halogen, methoxy and methylthio.
• R 4 represents substituted pyrimidin-2-yl.
• R 4 represents substituted pyrimidin-4-yl.
• R 4 represents substituted pyridyl, 1, 3, 5-triazinyl or isoquinolinyl.
• compounds I are preferred in which R 4 is substituted by pyridm-2-yl.
• compounds I are particularly preferred in which R 4 by cyano, halogen, C ⁇ -C 6 alkyl, C 2 -C 6 alkenyl, C -C ⁇ -Alk ⁇ nyl, C.-C haloalkyl, C 6 -C -Halogenalkenyl and C 2 -C 6 -Halogenalk yl is substituted.
• R 4 is Ci-C ⁇ alkoxy, C -C 5 -alkenyloxy, C 2 -Cs -alkionyloxy, C 2 -Ce haloalkenyloxy and C 2 -Ce haloalk yloxy is substituted.
• R 4 is substituted by phenyl, phenoxy, hetaryl or hetaryloxy, these groups in turn being able to be substituted by customary groups.
• Veromditch of formula I in which R n is 3-chlorine, R 1 is methyl, R 2 X is ethyl, R 3 is ethyl and R 4 for a compound corresponds in each case to one line of Table A.
• Table 319 Compounds of the formula I, in which R n is 3-chlorine, R 1 is hydrogen, R 2 X is ethoxy, R 3 is methylthio and R 4 for each compound corresponds to one row of Table A.
• Table 320 Compounds of the formula I, in which R n is 3-chlorine, R 1 is hydrogen, R 2 X is ethoxy, R 3 is methylthio and R 4 for each compound corresponds to one row of Table A.
• Table 320 Compounds of the formula I, in which R n is 3-chlorine, R 1 is hydrogen, R 2 X is ethoxy, R 3 is methylthio and R 4 for each compound corresponds to one row of Table A.
• Table 350 Compounds of the formula I in which R n is 3-chlorine, R 1 is hydrogen, R 2 X is methylamino, R 3 is ethylthio and R 4 for each compound corresponds to one row of Table A.
• Table 415 Compounds of the formula I, in which R n is 3-chlorine, R 1 is methyl, R 2 X is methylamino, R 3 is cyclopentyl and R 4 for each compound corresponds to one row of Table A.
• Table 416 Compounds of the formula I, in which R n is 3-chlorine, R 1 is methyl, R 2 X is methylamino, R 3 is cyclopentyl and R 4 for each compound corresponds to one row of Table A.
• Table 416 Compounds of the formula I, in which R n is 3-chlorine, R 1 is methyl, R 2 X is methylamino, R 3 is cyclopentyl and R 4 for each compound corresponds to one row of Table A.

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