Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/32—Oximes
  • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
  • C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups

Definitions

• the invention relates to a compound of formula
• X is CH or N
• Y is ORj and 2 is O, of
• R is C ⁇ -C 4 alkyl
• R 2 is C 2 -C 4 alkyl or C 3 -C 6 cycloalkyl
• R 8 is H or C C 4 alkyl
• R 9 is methyl, fluoromethyl or difluoromethyl; m is 0, 1 or 2;
• R 7 is a radical R ⁇ 0 ;
• G is O, S or -O-CH 2 -, wherein the -CH 2 group is bonded to the ring denoted by K;
• R 5 and R 6 are C C 6 alkyl, halo-d-Cealkyl, C 3 -C 6 cycloalkyl, halo-C 3 -C 6 cycloalkyl, d-C-e- alkoxy, halo-CrC 6 alkoxy, C ⁇ -C 6 alkylthio, halo-CrC 6 alkylthio, C ⁇ -C 6 alkylsulfynyl, halo- CrC 6 alkylsulfynyl, d-C 6 aikylsulfonyl, halo-C ⁇ -C 6 alkylsulfonyl, C ⁇ -C 6 alkylsulfonyloxy, halo-C ⁇ -C 6 alkylsulfonyloxy, d-Cealkoxy-d-Cealkyl, halo-d-Cealkoxy-Ci-Cealkyl, d-Cealky
• a number of compounds of formula (I), and of the formulae (III), (IV), (VI), (VIII) and (X) to (XIII) given hereinafter, contain asymmetrical carbon atoms, as a result of which the compounds may occur in optically active form. By virtue of the presence of the C X and oximino double bonds, the compounds may occur in the E and Z isomeric forms. Atropisomers of the compounds may also occur.
• the formulae (I), (III), (IV), (VI), (VIII) and (X) to (XIII) are to include all those possible isomeric forms and also mixtures thereof, for example racemates or mixtures of E/Z isomers, and also, optionally, salts thereof, even if these are not specifically mentioned every time.
• the E-isomer as indicated with E in the respective formulae is preferred.
• Carbon-containing groups and compounds each contain from 1 up to and including 8, especially from 1 up to and including 6, more especially from 1 up to and including 4, very especially 1 or 2, carbon atoms.
• Alkyl as a group perse and also as a structural unit of other groups and compounds, such as of haloalkyl, alkoxy, alkylthio, alkylsulfynyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, alkylamino, alkoxyiminomethyl, alkylaminocarbonyl and alkylaminothiocarbonyl, is, in each individual case giving due consideration to the number of carbon atoms contained in the group or compound in question, either straight-chain, that is to say methyl, ethyl, propyl, butyl, pentyl or hexyl, or branched, e.g.
• Alkenyl as a group per se and also as a structural unit of other groups and compounds, such as of haloalkenyl, is, in each individual case giving due consideration to the number of carbon atoms contained in the group or compound in question, either straight-chain, for example, vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl, or branched, for example isopropenyl.
• Alkynyl as a group perse and also as a structural unit of other groups and compounds, such as of haloalkynyl, is, in each individual case giving due consideration to the number of carbon atoms contained in the group or compound in question, either straight-chain, for example propargyl, 2-butynyl or 5-hexynyl, or branched, for example 2-ethynylpropyl or 2-propargylisopropyl.
• Cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
• Alkylene as a group per se and also as a structural unit of other groups and compounds, such as of haloalkylene, is, in each individual case giving due consideration to the number of carbon atoms contained in the group or compound in question, either straight-chain, for example -CH 2 CH 2 -, -CH 2 CH 2 CH 2 - or -CH2CH2CH2CH2-, or branched, for example -CH(CH 3 )-, -CH(C 2 H 5 )-, -C(CH 3 ) 2 -, - CH(CH 3 )CH 2 - or -CH(CH 3 )CH(CH 3 )-.
• Aryl is phenyl or naphthyl, especially phenyl.
• Heterocyclyl is a 5- to 7-membered aromatic or nonaromatic ring having from one to three hetero atoms selected from the group consisting of N, O and S. Preference is given to aromatic 5- and 6-membered rings having one nitrogen atom as hetero atom and optionally a further hetero atom, preferably nitrogen or sulfur, especially nitrogen.
• Preferred heteroaryl radicals are pyrazinyl, 3'-pyridyl, 2'-pyridyl, 4'-pyridyl, 2'-pyrimidinyl, 4'-pyrimidinyl, 5'- pyrimidinyl, 2'-thiazolyl, 2'-oxazolyl, 2'-furanyl, 3'-furanyl, 3'-tetrahydrofuranyl, 2'-thienyl, 3'- thienyl and 2'-thiazolyl.
• Halogen as a group perse and also as a structural unit of other groups and compounds, such as of haloalkyl, haloalkenyl and haloalkynyl, is fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, more especially fluorine or chlorine, very especially fluorine.
• Halo-substituted carbon-containing groups and compounds, such as haloalkyl, haloalkenyl or haloalkynyl may be partially halogenated or per-halogenated, it being possible in the case of poly-halogenation for the halogen substituents to be the same or different.
• haloalkyl as a group perse and also as a structural unit of other groups and compounds, such as of haloalkenyl, are methyl that is mono- to tri-substituted by fluorine, chlorine and/or by bromine, such as CHF 2 or CF 3 ; ethyl that is mono- to penta-substituted by fluorine, chlorine and/or by bromine, such as CH 2 CF 3 , CF 2 CF 3 , CF 2 CCI 3 , CF 2 CHCI 2) CF 2 CHF 2 , CF 2 CFCI 2 , CF 2 CHBr 2l CF2CHCIF, CF 2 CHBrF or CCIFCHCIF; propyl or isopropyi each mono- to hepta-substituted by fluorine, chlorine and/or by bromine, such as CH 2 CHBrCH 2 Br, CF 2 CHFCF 3 , CH 2 CF 2 CF 3 or CH(
• Haloalkynyl is, for example, CH 2 C ⁇ CF, CH 2 C ⁇ CCH 2 CI or CF 2 CF 2 C---CCH 2 F.
• a number of compounds of formula (I), and of the formulae (III), (IV), (VI), (VIII) and (X) to (XIII) given hereinafter, may, as is known to the person skilled in the art, be present in the form of tautomers, for example when A-R 7 is H.
• any reference to compounds of formulae (I), (III), (IV), (VI), (VIII) and (X) to (XIII) should be understood as including also corresponding tautomers, even when the latter are not specifically mentioned in each case.
• Compounds of formula (I), and of the formulae (III), (IV), (VI), (VIII) and (X) to (XIII) given hereinafter, that have at least one basic centre may, for example, form acid addition salts.
• Such salts are formed, for example, with strong inorganic acids, such as mineral acids, e.g. perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted or substituted, for example halo- substituted, d-C alkanecarboxylic acids, e.g. acetic acid, saturated or unsaturated dicarboxylic acids, e.g.
• oxalic acid malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, hydroxycarboxylic acids, e.g. ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or benzoic acid, or with organic sulfonic acids, such as unsubstituted or substituted, for example halo-substituted, d-C alkane- or aryl-sulfonic acids, e.g. methane- or p-toluene-sulfonic acid.
• compounds of formula (I) having at least one acid group may form salts with bases.
• Suitable salts with bases are, for example, metal salts, such as alkali metal or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethyl-, diethyl-, triethyl- or dimethyl-propyl-amine, or a mono-, di- or tri-hydroxy-lower alkylamine, e.g. mono-, di- or triethanolamine. It is also possible for corresponding internal salts to be formed.
• metal salts such as alkali metal or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, e.
• agrochemically advantageous salts also included, however, are salts which mith not be advantageous for agrochemical uses, which are used however, for example, for isolating and/or purifying free compounds of formula (I) or agrochemically acceptable salts thereof.
• any reference to the free compounds of formula (I) is to be understood as including also the corresponding salts of formula (I)
• any reference to the salts of the compounds of formula (I) is to be understood as including also the corresponding free compounds of the formula (I).
• tautomers of compounds of formulae (I), (III), (IV), (VI), (VIII) and (X) to (XIII) and salts thereof In each case the free form is generally preferred.
• R 2 is ethyl, propyl, butyl, isopropyl, isobutyl, sec.butyl or tert-butyl, especially ethyl or propyl, more especially ethyl;
• R 3 is H, d-dalkyl, C ⁇ -C 4 alkoxy, OH, CN, NO 2 , halogen, halo-C C 4 alkyl or halo-C C 4 - alkoxy, preferably H, d-C 4 alkyl, d-C 4 alkoxy or halogen, especially H, methyl, methoxy, chlorine or fluorine, more especially H;
• R 4 is H, d-dalkyl, C ⁇ -C 4 alkoxy, OH, CN, NO 2 , halogen, halo-C C 4 alkyl or halo-d-C 4 - alkoxy, preferably H, d-C alkyI, d-C alkoxy or halogen; especially H, methyl, methoxy, chlorine or fluorine; more especially H;
• R 8 is H or d-C 2 alkyl, preferably C C 2 alkyl, especially methyl;
• R 6 is halogen, C C 4 alkyl, halo-C C 4 alkyl, halo-C C alkoxy, C 3 -C 6 cycloalkyl. halo-C 3 -
• A is a direct bond, d-Cioalkylene, or halo-d-Cioalkylene; preferably a direct bond or C ⁇ -C 4 alkylene; especially a direct bond or methylene; (15) a compound of formula (I) wherein A is a direct bond and
• R 7 is d-d-alkyl.
• CH 2 -CH CH 2 or CH 2 -C ⁇ CH, especially methyl or ethyl, more especially ethyl;
• the invention relates also to a process for the preparation of the compounds of formula (I) and, where applicable, their E/Z isomers, mixtures of E/Z isomers and or tautomers, wherein n, q, A, G, X, Y, Z, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 9 are as defined above for formula (I) and wherein the provisos mentioned above for the compounds of formula (I) apply, in each case in free form or in salt form, which process comprises a1 ) reacting a compound of formula
• n, q, A, G, R 2 , R 5 , Re and R 7 are as defined for formula (I), optionally in the presence of a base, with a compound of formula
• n, q, G, X, Y, Z, R 2 , R 3 , R 4 , R 5 , R 6 and R 9 are as defined above for formula (I) and wherein the provisos mentioned above for the compounds of formula (I) apply, with a compound of formula X A-R 7 (VII), wherein A and R 7 are as defined above for formula (I) and X , is a leaving group as for formula (II);
• the invention relates also to a process for the preparation of compounds of formula (III), in each case in free form or in salt form, which process comprises e) reacting a compound of formula (IV) wherein n, q, A, G, R 2) R 5 , R 6 and R 7 are as defined for formula (I), optionally in the presence of a base, with H 2 NOH or with a salt thereof; or
• the invention relates also to a process for the preparation of compounds of formula (VI), in each case in free form or in salt form, which process comprises g) reacting a compound of formula (VI), in each case in free form or in salt form, which process comprises g) reacting a compound of formula (VI), in each case in free form or in salt form, which process comprises g) reacting a compound of formula (VI), in each case in free form or in salt form, which process comprises g) reacting a compound of formula (VI), in each case in free form or in salt form, which process comprises g) reacting a compound of formula (VI), in each case in free form or in salt form, which process comprises g) reacting a compound of formula (VI), in each case in free form or in salt form, which process comprises g) reacting a compound of formula (VI), in each case in free form or in salt form, which process comprises g) reacting a compound of formula (VI), in each case in free form or in salt form, which process comprises g) reacting
• n, q, G, X, Y, Z, R 2 , R 3 , R 4 , R 5 , R 6 and R 9 are as defined above for formula (I), with hydroxylamine.
• the invention relates also to a process for the preparation of compounds of formula (X), in each case in free form or in salt form, which process comprises h) reacting a compound of formula (VIII) with a compound of formula (II).
• the invention relates also to a process for the preparation of compounds of formula (VIM), in each case in free form or in salt form, which process comprises i) reacting a compound of formula (VIM), in each case in free form or in salt form, which process comprises i) reacting a compound of formula (VIM), in each case in free form or in salt form, which process comprises i) reacting a compound of formula (VIM), in each case in free form or in salt form, which process comprises i) reacting a compound of formula (VIM), in each case in free form or in salt form, which process comprises i) reacting a compound of formula (VIM), in each case in free form or in salt form, which process comprises i) reacting a compound of formula (VIM), in each case in free form or in salt form, which process comprises i) reacting a compound of formula (VIM), in each case in free form or in salt form, which process comprises i) reacting a compound of formula (VIM), in each case in free form or in salt form
• n, q, G, R 2 , R5 and R 6 are as defined for formula (I), and which is known or can be prepared in accordance with methods known perse, with a nitrite.
• the invention also relates to the following novel intermediates (XII) and (XIII) and the methods for the preparation of the compounds of the formulae (III), (II) and (XIII) known per se:
• the reactions described hereinbefore and hereinafter are carried out in a manner known per se, for example in the absence or usually in the presence of a suitable solvent or diluent or of a mixture thereof, the reactions being carried out, as required, with cooling, at room temperature or with heating, for example in a temperature range of from approximately 0°C to the boiling temperature of the reaction medium, preferably from approximately 20°C to approximately +120°C, especially from 60°C to 80°C.
• a suitable solvent or diluent or of a mixture thereof the reactions being carried out, as required, with cooling, at room temperature or with heating, for example in a temperature range of from approximately 0°C to the boiling temperature of the reaction medium, preferably from approximately 20°C to approximately +120°C, especially from 60°C to 80°C.
• Especially advantageous reaction conditions may be found in the Examples.
• the reactants may be reacted with one another as they are, that is to say without the addition of a solvent or diluent, for example in molten form.
• a solvent or diluent for example in molten form.
• the addition of an inert solvent or diluent or a mixture thereof is advantageous.
• the reactions are, if required, carried out in a closed vessel, under pressure, and under a protective gas atmosphere, for example nitrogen or argon, especially nitrogen; and/or under anhydrous conditions; preferably in an inert gas atmosphere and under normal pressure.
• a protective gas atmosphere for example nitrogen or argon, especially nitrogen; and/or under anhydrous conditions; preferably in an inert gas atmosphere and under normal pressure.
• the products are usually isolated in accordance with customary methods, for example by filtration, crystallisation, distillation or chromatography, or any suitable combination of those methods.
• the starting materials given hereinbefore and hereinafter that are used to prepare the compounds of formula (I) and, where applicable, their E/Z isomers and tautomers are known or can be prepared in accordance with methods known perse, for example according to the details given hereinafter.
• Suitable leaving groups Xi in the compounds (II) and (VII) are, for example, hydroxy, d-C 8 alkoxy, halo-d-C 8 alkoxy, d-C 8 alkanoyloxy, mercapto, d-C 8 alkylthio, halo-d-C 8 alkyl- thio, C C 8 alkanesulfonyloxy, halo-C ⁇ -C 8 alkanesulfonyloxy, benzenesulfonyloxy, toluene- sulfonyloxy and halogen, preferably toluenesulfonyloxy, trifluoromethanesulfonyloxy and halogen, especially halogen.
• Suitable bases for facilitating the reaction are, for example, alkali metal or alkaline earth metal hydroxides, hydrides, amides, alkanolates, acetates, carbonates, dialkylamides or alkylsilylamides, alkylamines, alkylenediamines, unsubstituted or N-alkylated, saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines.
• DBU ,5-diaza- bicyclo[5.4.0]undec-5-ene
• Examples of usefule solvent for carrying out the reaction include: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene and tetrachloro-ethene; esters, such as ethyl acetate; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl
• bases used in excess such as triethylamine, pyridine, N-methylmorpholine or N,N-diethylaniline, may also serve as solvents or diluents.
• the reaction is carried out advantageously in a temperature range from approximately 0°C to approximately 180°C, especially from approximately 10°C to approximately 80°C, in many cases in the range from room temperature to the reflux temperature of the reaction mixture. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours.
• a compound (II) is reacted with a compound (III) at from 0°C to 80°C, preferably from 10°C to 30°C , in an inert solvent, preferably an amide, especially N,N-dimethylformamide, in the presence of a metal hydride, preferably sodium hydride.
• Examples of useful solvents for carrying out the reaction or diluents include those mentioned in variants a1/a2/a3 and h).
• the reaction is carried out advantageously in a temperature range from approximately 0°C to approximately 180°C, especially from approximately 10°C to approximately 80°C, in many cases in the range from room temperature to the reflux temperature of the reaction mixture. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours.
• solvents or diluents for carrying out the reaction include: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chlorobenzene, dichlorobenzene, bromo benzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachlorome- thane, dichloroethane, trichloroethene and tetrachloro-ethene; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert -butyl methyl ether, ethylene glycol mono- methyl ether, ethylene glycol mono ethyl ether, ethylene glycol dimethyl ether, dimethoxydie
• the reaction is carried out advantageously in a temperature range from approximately 0°C to approximately +120°C, especially from approximately 80°C to approximately +120°C. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours.
• Suitable oxidising agents are, for example, inorganic peroxides, such as sodium perborate, or hydrogen peroxide, or organic per-acids, such as perbenzoic acid or peracetic acid, or mixtures of organic acids and hydrogen peroxide, for example acetic acid/hydrogen peroxide.
• solvents or diluents for carrying out the reaction include: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chlorobenzene, dichlorobenzene, bromo benzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachlorome- thane, dichloroethane, trichloroethene and tetrachloro-ethene; esters, such as ethyl acetate; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert -butyl methyl ether, ethylene glycol mono methyl ether, ethylene glycol mono ethyl ether, ethylene glycol dimethyl
• acids used in excess for example strong organic carboxylic acids, such as unsubstituted or substituted, for example halo-substituted, C,-C 4 alkane-carboxylic acids, e.g. formic acid, acetic acid or propionic acid, may also serve as solvent or diluent.
• strong organic carboxylic acids such as unsubstituted or substituted, for example halo-substituted, C,-C 4 alkane-carboxylic acids, e.g. formic acid, acetic acid or propionic acid, may also serve as solvent or diluent.
• the reaction is carried out advantageously in a temperature range from approximately 0°C to approximately +120°C, especially from approximately 0°C to approximately +40°C. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours.
• Suitable bases for facilitating the reaction are, for example, those mentioned in variants a1/a2/a3/h.
• useful solvents or diluents for carrying out the reaction include those mentioned in variants a1/a2/a3/h).
• the reaction is carried out advantageously in a temperature range from approximately 0°C to approximately 180°C, especially from approximately 10°C to approximately 80°C, in many cases in the range from room temperature to the reflux temperature of the reaction mixture. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours.
• Suitable bases for facilitating the reaction are, for example, those mentioned in variants a1/a2/a3/h.
• useful solvents or diluents for carrying out the reaction include those mentioned in variant a1/a2.
• the reaction is carried out advantageously in a temperature range from approximately 0°C to approximately 180°C, especially from approximately 10°C to approximately 80°C, in many cases in the range from room temperature to the reflux temperature of the reaction mixture. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours.
• a compound of formula (VIM) is reacted with a compound of formula (IX) at from 0°C to 120°C, preferably from 60 °C to 120°C, in an inert solvent, preferably an amine, especially pyridine.
• an inert solvent preferably an amine, especially pyridine.
• Suitable reactants are especially alkyl nitrites, preferably isopentyl nitrite.
• Suitable acids for facilitating the reaction are, for example, hydrohalic acids and nitric acid, especially gaseous hydrogen chloride.
• Suitable solvents are especially those mentioned under variant d), especially ethers, such as diethyl ether, di-n-butyl ether and methyl isobutyl ether; or alcohols, for example ethanol and methanol.
• ethers such as diethyl ether, di-n-butyl ether and methyl isobutyl ether
• alcohols for example ethanol and methanol.
• the reaction is carried out advantageously in a temperature range from approximately 0°C to approximately 180°C, preferably from approximately 0°C to 80°C, especially at room temperature. Preference is given to a reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours.
• the compounds of formulae (I) to (XIII) may be in the form of one of the possible isomers or in the form of a mixture thereof, for example according to the number of asymmetric carbon atoms and the absolute and relative configuration thereof in the form of pure isomers, such as antipodes and/or diastereoisomers, or in the form of mixtures of isomers, such as mixtures of enantiomers, for example racemates, mixtures of diastereoisomers or mixtures of racemates; the invention relates both to the pure isomers and to all possible mixtures of isomers and this is to be understood accordingly hereinbefore and hereinafter, even if stereochemical details are not specifically mentioned in each case.
• the compounds of formulae (I), (III), (IV), (VI), (VI ) and (X) to (XIII) can also be obtained in the form of their hydrates and/or may include other solvents, for example solvents that may have been used for the crystallisation of compounds in solid form.
• the invention relates to all those embodiments of the process according to which a compound obtainable as starting material or intermediate at any stage of the process is used as starting material and all or some of the remaining steps are carried out, or a starting material is used in the form of a derivative or a salt and/or its racemates or antipodes, or, especially, is formed under the reaction conditions.
• the invention relates also to starting materials and intermediates used according to the invention in the preparation of compounds of formula (I), especially the compounds of formulae (III), (IV), (VI), (VIM) and (X) to (XIII), which are novel, to their use and to processes for the preparation thereof.
• the preferred meanings of R 2 , R 5 , R 6 , R 7 , A, G, q und n in these compounds of the of formulae (III), (IV), (VI), (VI ) and (X) to (XIII) are the same as given for the compounds of the formula (I).
• the compounds of formulae (III) and (VIII) can be prepared analogously to Examples P1d) and P1c), respectively.
• the compounds of formula (I) according to the invention are valuable preventive and/or curative active ingredients having a very advantageous biocidal spectrum even at low rates of concentration, while being well tolerated by warm-blooded animals, fish and plants.
• the compounds of the invention are effective against all or individual development stages of normally sensitive animal pests, but also of resistant animal pests, such as insects and representatives of the order Acarina, and phytopathogenic fungi.
• the insecticidal, ovicidal and/or acaricidal action of the compounds of the invention may manifest itself directly, i.e. in the mortality of the pests, which occurs immediately or only after some time, for example during moulting, or of their eggs, or indirectly, for example in reduced oviposition and/or hatching rate, good activity corresponding to a mortality of at least 50 to 60 %.
• the mentioned animal pests include, for example, those mentioned in European Patent Application EP-A-736252.
• the said pests mentioned in EP-A-736 252 are included by reference in the subject matter of the present invention.
• the mentioned phytopathogenic fungi include, for example: of the class of Fungi imperfecti, for example, Botrytis spp., Pyricularia spp., Helmintho- sporium spp., Fusarium spp., Septoria spp., Cercospora spp. and Alternaria spp.; of the class of Basidiomycetes, for example, Rhizoctonia spp., Hemileia spp. and Puccinia spp.; of the class of Ascomycetes, for example, Venturia spp., Erysiphe spp., Podosphaera spp., Monilinia spp. and Uncinula spp.; and of the class of Oomycetes, for example, Phytophthora spp., Pythium spp. and Plasmopara spp..
• Target crops are especially cereals, such as wheat, barley, rye, oats, rice, maize and sorghum; beet, such as sugar beet and fodder beet; fruit, such as pomes, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries, or berries, for example strawberries, raspberries and blackberries; leguminous plants, such as beans, lentils, peas and soybeans; oil plants, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and groundnuts; cucurbitaceae, such as marrows, cucumber and melons; fibre plants, such as cotton, flax, hemp and jute; citrus fruit, such as oranges, lemons, grapefruit and mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and paprika; lauraceae, such as avocados, cinnamon and camphor; and tobacco, nuts, coffee
• the compounds according to the invention are especially suitable for controlling insects and representatives of the order Acarina, especially plant-destructive feeding insects, such as Anthonomus grandis, Diabrotica balteata, Heliothis virescens larvae, Plutella xylostella and Spodoptera littoralis larvae, and spider mites, such as Tetranychus spp., in cotton, fruit, maize, soybean, rape and vegetable crops.
• plant-destructive feeding insects such as Anthonomus grandis, Diabrotica balteata, Heliothis virescens larvae, Plutella xylostella and Spodoptera littoralis larvae
• spider mites such as Tetranychus spp., in cotton, fruit, maize, soybean, rape and vegetable crops.
• the invention therefore relates also to pesticides, such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, coatable pastes, dilute emulsions, wettable powders, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymer substances, comprising - at least - one of the compounds of the invention, the type of formulation being chosen in accordance with the intended objectives and prevailing circumstances.
• pesticides such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, coatable pastes, dilute emulsions, wettable powders, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymer substances, comprising - at least - one of the compounds of the invention, the type of formulation being chosen in accordance with the intended objectives and prevailing circumstances.
• the active ingredient is used in those compositions in pure form: a solid active ingredient, for example, in a specific particle size, or preferably together with - at least - one of the adjuvants customary in formulation technology, such as extenders, for example solvents or solid carriers, or surface-active compounds (surfactants).
• a solid active ingredient for example, in a specific particle size, or preferably together with - at least - one of the adjuvants customary in formulation technology, such as extenders, for example solvents or solid carriers, or surface-active compounds (surfactants).
• formulation adjuvants for example, solid carriers, solvents, stabilisors, "slow release” adjuvants, colorants and optionally surface-active substances (surfactants).
• carriers and adjuvants all substances customarily used in plant protection compositions, especially in compositions for controlling slugs and snails.
• Suitable adjuvants, such as solvents, solid carriers, surface-active compounds, non-ionic surfactants, cationic surfactants, anionic surfactants and other adjuvants in the compositions used according to the invention are, for example, trie same substances as described in EP-A-736 252.
• the said adjuvants mentioned in EP-A-736 252 are included by reference in the subject matter of the present invention.
• compositions for controlling pests can be formulated, for example, in the form of wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates or aerosols.
• the compositions are of the same type as those described, for example, in EP-A-736 252.
• compositions usually comprise 0.1 to 99%, preferably 0.1 to 95%, of active ingredient, and 1 to 99.9%, preferably 5 to 99.9%, of - at least - one solid or liquid adjuvant, it generally being possible for 0 to 25%, preferably 0.1 to 20%, of the composition to be surfactants (in each case percentages are by weight).
• surfactants in each case percentages are by weight.
• Preferred formulations have especially the composition described in EP-A-736 252, Examples F1 to F8.
• compositions according to the invention can be substantially broadened and adapted to prevailing circumstances by the addition of other insecticidal, acaricidal and/or fungicidal active ingredients.
• suitable additional active ingredients include representatives of the following classes of compounds: organophosphorus compounds, nitrophenol derivatives, formamidines, ureas, benzoylureas, carbamates, pyrethroids, chlorinated hydrocarbons, neonicotinoids, macrolides and Bacillus thuringiensis preparations.
• the compositions according to the invention may also comprise further solid or liquid adjuvants, such as stabilisers, for example vegetable oils or epoxidised vegetable oils (e.g.
• epoxidised coconut oil, rape oil or soybean oil epoxidised coconut oil, rape oil or soybean oil
• antifoams for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, as well as fertilisers or other active ingredients for obtaining special effects, for example bactericides, nematicides, molluscicides or selective herbicides.
• compositions according to the invention are prepared in known manner, in the absence of adjuvants, for example by grinding and/or sieving a solid active ingredient or mixture of active ingredients, for example to a specific particle size, and in the presence of at least one adjuvant, for example by intimately mixing and/or grinding the active ingredient or mixture of active ingredients with the adjuvant(s).
• the invention relates also to those methods for the preparation of the compositions according to the invention and to the use of the compounds of formula (I) in the preparation of those compositions.
• the invention relates also to the methods of application of the compositions, i.e. the methods of controlling pests of the mentioned type, such as spraying, atomising, dusting, coating, dressing, scattering or pouring, which are selected in accordance with the intended objectives and prevailing circumstances, and to the use of the compositions for controlling pests of the mentioned type.
• Typical rates of concentration are from 0.1 to 1000 ppm, preferably from 0.1 to 500 ppm, of active ingredient.
• the rates of application per hectare are generally from 1 to 2000 g of active ingredient per hectare, especially from 10 to 1000 g/ha, preferably from 20 to 600 g/ha.
• a preferred method of application in the area of plant protection is application to the foliage of the plants (foliar application), the number of applications and the rate of application depending on the risk of infestation by the pest in question.
• the active ingredient can also penetrate the plants through the roots (systemic action) if the locus of the plants is impregnated with a liquid formulation or if the active ingredient is incorporated in solid form into the locus of the plants, for example into the soil, e.g. in granular form (soil application). In paddy rice crops, such granules may be applied in metered amounts to the flooded rice field.
• compositions according to the invention are also suitable for protecting plant propagation material, e.g. seed, such as fruit, tubers or grains, or plant cuttings, from fungal infections and animal pests.
• the propagation material can be treated with the formulation before planting: seed, for example, can be dressed before being sown.
• the compounds of the invention can also be applied to grains (coating), either by impregnating the grains with a liquid formulation or by coating them with a solid formulation.
• the formulation can also be applied to the planting site when the propagation material is being planted, for example to the seed furrow during sowing.
• the invention relates also to those methods of treating plant propagation material and to the plant propagation material thus treated.
• Example P1 (2- ⁇ 2-[4-(3-Trifluoromethylphenoxy)-phenyl]-2-ethoxyimino-1-ethyl-ethylidene- aminooxymethyl ⁇ -phenyl)-3-methoxy-acrylic acid methyl ester (compound 1.1) a) 1 -(4-Fluorophenyl)-butan-1 -one
• HCl gas is introduced for one minute into 1 litre of diethyl ether and then 277 g of 1-[4-(3- trifluoromethylphenoxy)-phenyl]-butan-1-one are added. 126.2 g of isopentyl nitrite are added dropwise to that mixture, the reaction mixture is then stirred at room temperature for 5 hours, HCl gas is again introduced for one minute and the reaction mixture is left to stand at room temperature for 14 hours. The reaction mixture is filtered and the filtrate is concentrated by evaporation in vacuo. The residue is made into a slurry with hexane and filtered, and the filter residue is dried in vacuo to yield the title compound having a melting point of 74-76°C.
• Example P2 The other compounds listed in Tables 1 to 4 can also be prepared in a manner analogous to that described in Example P1.
• the temperatures given denote the melting point in °C of the compound in question.
• Table 1.2 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.3 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.4 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 2-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.5 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.6 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 3-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.7 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 2-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.8 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 4-Br and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.9 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 3-Br and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.10 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 2-Br and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.11 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 4-F and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.12 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 3-F and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.13 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 2-F and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.14 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.15 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 4-O-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.16 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 4-O-CH 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.17 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 4-O-C 2 H 5 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.18 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 4-O-n-butyl and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.20 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 4-C 2 H 5 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.21 Compounds of general formula (1.1) wherein R 2 is n-propyl, (R 6 ) n is 4-C 3 H 7 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.22 Compounds of general formula (1.1) wherein R 2 is n-propyl, (R 6 ) n is 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.23 Compounds of general formula (1.1) wherein R 2 is n-propyl, (R 6 ) choir is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.24 Compounds of general formula (1.1) wherein R 2 is n-propyl, (R 6 ) n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.25 Compounds of general formula (1.1) wherein R 2 is n-propyl, (R 6 ) n is 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.26 Compounds of general formula (1.1) wherein R 2 is n-propyl, (R 6 ) n is 4-O-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.28 Compounds of general formula (1.1) wherein R 2 is cyclopropyl, (R 6 ) n is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.29 Compounds of general formula (1.1) wherein R 2 is cyclopropyl, (R 6 ) n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.31 Compounds of general formula (1.1) wherein R 2 is cyclopropyl, (R 6 ) n is 4-OCF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.32 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 3-CI, 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 1.33 Compounds of general formula (1.1) wherein R 2 is ethyl, (R 6 ) n is 4-CI, 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 2.2 Compounds of general formula (1.2) wherein R T is methyl, R 2 is ethyl, (R 6 ) n is 4-
• Table 2.5 Compounds of general formula (I.2) wherein Ri is methyl, R 2 is ethyl, (R 6 ) n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 2.6 Compounds of general formula (I.2) wherein Ri is methyl, R 2 is ethyl, (R 6 ) n is 3-CI and the substituent A-R corresponds in each case to a line of Table A.
• Table 2.7 Compounds of general formula (I.2) wherein R*. is methyl, R 2 is ethyl, (R 6 ) n is 2-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 2.8 Compounds of general formula (I.2) wherein Ri is methyl, R 2 is ethyl, (R 6 ) n is 4-Br and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 2.9 Compounds of general formula (I.2) wherein Ri is methyl, R 2 is ethyl, (R 6 ) n is 3-Br and the substituent A-R 7 corresponds in each case to a line of Table A.
• O-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• O-CH 3 and the substituent A-R corresponds in each case to a line of Table A.
• O-C 2 H 5 and the substituent A-R 7 corresponds in each case to a line of Table A.
• O-n-butyl and the substituent A-R 7 corresponds in each case to a line of Table A.
• 4-C 3 H 7 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 2.24 Compounds of general formula (I.2) wherein R 2 is n-propyl, (R 6 ) n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• (R 6 ) n is 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• (R 6 ) n is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• (R 6 ) n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• (R 6 ) n is 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 2.31 Compounds of general formula (I.2) wherein Ri is methyl, R 2 is cyclopropyl, (R 6 ) n is 4-OCF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 2.32 Compounds of general formula (I.2) wherein Ri is methyl, R 2 is ethyl, (R 6 ) n is 3- Cl, 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.2 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.3 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) endeavour is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.4 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 2-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.5 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.6 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 3-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.7 Compounds of general formula (1.3) wherein R 2 is ethyl, (R 6 ) n is 2-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.8 Compounds of general formula (1.3) wherein R 2 is ethyl, (R 6 ) n is 4-Br and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.9 Compounds of general formula (1.3) wherein R 2 is ethyl, (R 6 ) n is 3-Br and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.10 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 2-Br and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.11 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 4-F and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.12 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 3-F and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.13 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 2-F and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.14 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.15 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 4-O-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.16 Compounds of general formula (1.3) wherein R 2 is ethyl, (R 6 ) n is 4-O-CH 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.17 Compounds of general formula (1.3) wherein R 2 is ethyl, (R 6 ) n is 4-O-C 2 H 5 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.18 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 4-O-n-butyl and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.19 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 4-CH 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.20 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 4-C 2 H 5 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.21 Compounds of general formula (I.3) wherein R 2 is n-propyl, (R 6 ) n is 4-C 3 H 7 and the substituent A-R corresponds in each case to a line of Table A.
• Table 3.22 Compounds of general formula (I.3) wherein R 2 is n-propyl, (R 6 ) n is 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.23 Compounds of general formula (I.3) wherein R 2 is n-propyl, (R 6 ) n is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.24 Compounds of general formula (1.3) wherein R 2 is n-propyl, (R 6 ) n is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.25 Compounds of general formula (1.3) wherein R 2 is n-propyl, (R 6 ) n is 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.26 Compounds of general formula (1.3) wherein R 2 is n-propyl, (R 6 ) n is 4-O-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.27 Compounds of general formula (1.3) wherein R 2 is cyclopropyl, (R 6 ) n is 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.28 Compounds of general formula (1.3) wherein R 2 is cyclopropyl, (R 6 ) n is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.29 Compounds of general formula (1.3) wherein R 2 is cyclopropyl, (R 6 ) n is 4-Cl and the substituent A-R 7 corresponds in each case to a line of Table A.
• 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.31 Compounds of general formula (I.3) wherein R 2 is cyclopropyl, (R 6 ) n is 4-OCF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.32 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 3-CI, 4-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Table 3.33 Compounds of general formula (I.3) wherein R 2 is ethyl, (R 6 ) n is 4-CI, 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
• Example B1 Action against Phytophthora infestans on tomatoes a) Curative action
• tomato plants of the "Red Gnome" variety are sprayed with a zoospore suspension of the fungus and incubated in a humidity chamber at 18 to 20°C and saturated humidity. Humidifying is discontinued after 24 hours.
• the plants have dried off, they are sprayed with a mixture prepared from a wettable powder formulation of the test compound at a concentration of 200 ppm.
• the plants are again placed in the humidity chamber for 4 days. The number and size of the typical leaf specks that have appeared after that time serve as a measure for evaluating the effectiveness of the test compounds.
• a wettable powder formulation of the test compound is poured at a concentration of 60 ppm (based on the volume of soil) onto the surface of the soil in which three-week-old tomato plants of the "Red Gnome" variety have been potted. After a waiting period of three days, the undersides of the leaves of the plants are sprayed with a zoospore suspension of Phytophthora infestans. The treated plants are then placed in a spraying cabinet for 5 days at 18 to 20°C and saturated humidity. After that period, typical leaf specks appear, the number and size of which are used to evaluate the effectiveness of the test compounds.
• Example B2 Action against Plasmopara viticola (Bert, et Curt.) (Berl. et DeTonO on vines a) Residual-preventive action
• Vine cuttings of the "Chasselas" variety are cultivated in a greenhouse. At the 10-leaf stage, 3 plants are sprayed with a mixture comprising the active ingredient in a concentration of 200 ppm. After the spray-coating has dried, the plants are uniformly infected on the undersides of the leaves with a spore suspension of the fungus. The plants are then kept in a humidity chamber for 8 days. After that time, distinct disease symptoms appear in the control plants. The number and size of the infection sites on the treated plants serve as a measure for evaluating the effectiveness of the test compounds.
• Vine cuttings of the "Chasselas” variety are cultivated in a greenhouse and are infected at the 10-leaf stage, on the undersides of the leaves, with a spore suspension of Plasmopara viticola. After being kept in a humidity chamber for 24 hours, the plants are sprayed with a mixture comprising the active ingredient in concentrations of 200 ppm, 60 ppm and 20 ppm. The plants are then kept in the humidity chamber for a further 7 days. After that time, the disease symptoms appear in the control plants. The number and size of the infection sites on the treated plants serve as a measure for evaluating the effectiveness of the test compounds.
• the plants treated with compounds from Tables 1 to 4 exhibit an infestation of 20% or less.
• the compounds 1-1 to 1-6, 2-1 to 2-6 and 3-1 to 3-6 complete curative action is still obtained even at a concentration of the test compound of 20 ppm.
• Example B3 Action against Puccinia graminis on wheat a) Residual-protective action
• wheat plants are sprayed to drip point with an aqueous spray mixture
• Wheat plants are watered 5 days after sowing with an aqueous spray mixture (0.006% active ingredient, based on the volume of soil). Care is taken that the spray mixture does not come into contact with the parts of the plants above the soil.
• the treated plants are infected 48 hours later with a uredospore suspension of the fungus. After an incubation period of 48 hours (conditions: 95 to 100 % relative humidity at 20°C), the plants are placed in a greenhouse at 22°C. Evaluation of rust pustule development is made 12 days after infection.
• Example B4 Action against Ervsiphe graminis on barley a) Residual-protective action
• Barley plants about 8 cm in height are sprayed to drip point with an aqueous spray mixture (0.02% active ingredient) and dusted 3 to 4 hours later with conidia of the fungus.
• the infected plants are placed in a greenhouse at 22 C C.
• the fungus infestation is evaluated 10 days after infection.
• Barley plants about 8 cm in height are watered with an aqueous spray mixture (0.002% active ingredient, based on the volume of soil). Care is taken that the spray mixture does not come into contact with the parts of the plants above the soil.
• the treated plants are dusted 48 hours later with conidia of the fungus.
• the infected plants are placed in a greenhouse at 22°C. The fungus infestation is evaluated 10 days after infection.
• Compounds from Tables 1 to 4 in general are able to suppress infestation with the disease to less than 20 % and, in some cases, to suppress it completely.
• Example B5 Action against Septoria nodorum on wheat
• Wheat plants are sprayed at the 3-leaf stage with a spray mixture (60 ppm a.i.) prepared from a wettable powder formulation of the test compounds. 24 hours later, the treated plants are infected with a conidia suspension of the fungus. The plants are then incubated for 2 days at 90-100 % relative humidity and placed in a greenhouse at 20-24°C for a further 10 days. Fungal infestation is evaluated 13 days after infection. Less than 1 % of the wheat plants exhibit infestation.
• a spray mixture 60 ppm a.i.
• Example B6 Action against Aphis craccivora
• Pea seedlings are infested with Aphis craccivora, subsequently sprayed with a spray mixture comprising 100 ppm of the test compound and then incubated at 20°C. 3 and
• the percentage reduction in population is determined by comparing the number of dead aphids on the treated plants with that on untreated plants.
• Compounds from Tables 1 to 4 generally exhibit good activity in this test.
• compounds 1 -1 to 1 -6, 2-1 to 2-6 and 3-1 to 3-6 exhibit an activity of more than 80 % in this test.
• Maize seedlings are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of the test compound. After the spray-coating has dried, the maize seedlings are populated with 10 Diabrotica balteata larvae in the second stage and then placed in a plastics container. 6 days later, the percentage reduction in population (% activity) is determined by comparing the number of dead larvae on the treated plants with that on untreated plants.
• Example B8 Action against Heliothis virescens
• Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of test compound. After the spray-coating has dried, the plants are populated with 10 caterpillars of Heliothis virescens in the first stage and then placed in a plastics container. 6 days later, the percentage reduction in population and the percentage reduction in feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage on the treated plants with that on untreated plants. Most compounds from Tables 1 to 4 exhibit good activity in this test. In particular, compounds 1 -1 to 1 -6, 2-1 to 2-6 and 3-1 to 3-6 exhibit an activity of more than 80 % in this test.
• Example B9 Action against Spodoptera littoralis
• Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of test compound. After the spray-coating has dried, the plants are populated with 10 caterpillars of Spodoptera littoralis in the third stage and then placed in a plastics container. 3 days later, the percentage reduction in population and the percentage reduction in feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage on the treated plants with that on untreated plants.
• Example B10 Action against Tetranvchus urticae
• Young bean plants are populated with a mixed population of Tetranychus urticae and sprayed one day later with an aqueous emulsion spray mixture comprising 100 ppm of test compound. The plants are then incubated for 6 days at 25°C and subsequently evaluated. The percentage reduction in population (% activity) is determined by comparing the number of dead eggs, larvae and adults on the treated plants with that on untreated plants.
• Compounds from Tables 1 to 4 generally exhibit good activity in this test.
• compounds 1 -1 to 1 -6, 2-1 to 2-6 and 3-1 to 3-6 exhibit an activity of more than 80 % in this test.

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