PHENYL-METHOXYIMINO-ACETIC ACID DERIVATIVES AS PESTICIDES

Abstract: Compounds of formula (I) wherein: A is a group CH2O or CH2ON=C(R1); X1 and X2 independently of one another, are C1-C4-alkyl; Y is OH, O(C1-C4-alkyl), NH2 or NHCH3; R1 is C1-C4-alkyl, cyclopropyl, cyano, trifluoromethyl or C1-C4-alkoxy; R is aryl, hetaryl or heterocyclyl, whereby the above-mentioned groups may be substituted by identical or different substituents, have microbicidal activity and may be used for the control and prevention of plant-pathogenic fungi in agriculture, horticulture and in the field of hygiene.

Description: Phenyl-methoxyimino-acetic acid derivatives as pesticides The present invention relates to new phenyl-methoxyimino-acetic acid derivatives having microbicidal activity, a process for their preparation, agrochemical compositions containing these active ingredients, as well as the use thereof in the control and prevention of plant- pathogenic fungi in agriculture and in horticulture. The new compounds fall within formula I, wherein: A is a group CH 2 0 or CH 2 ON=C(R 1 ); Xi and X 2 independently of one another, are d-d-alkyl; Y is OH, O(Cι-C 4 -alkyl), NH 2 or NHCH 3 ; Ri is Cι-C -alkyl, cyclopropyl, cyano, trifluoromethyl or d-C 4 -alkoxy; R is aryl, hetaryl or heterocyclyl, whereby the above-mentioned groups may be substituted by one or more identical or different substituents, selected from the group comprising halogen; Cι-C 6 -alkyl; aryl which is optionally mono- to trisubstituted by identical or different substituents from Cι-C -alkyl, halogen, d-C 4 -alkoxy, CrC 4 -halogenalkyl or cyano; C C 6 -alkoxy; halogen-d-C 6 -alkoxy; aryloxy which is optionally mono- to trisubstituted by identical or different substituents from d-d-alkyl, halogen, Cι-C 4 -alkoxy, C C 4 - halogenalkyl or cyano; halogen-C r C 6 -alkyl; C C 6 -alkylthio; halogen-d-C 6 -alkylthio; CrC 6 -alkylsulfinyl; halogen-CrC 6 -alkylsulfinyl; Cι-C 6 -alkylsulfonyl; halogen-d-Ce-alkylsulfonyl; C 2 -C 6 -alkenyl; C 2 -C 6 -alkenyloxy; C 2 -C 6 -alkynyl; C 3 -C 6 - alkynyloxy; halogen-C -C 6 -alkenyl; halogen-C 2 -C 6 -alkenyloxy; halogen-C 2 -C 6 -alkynyl; halogen-C 3 -C 6 -alkynyloxy; C C 6 -alkylcarbonyl; halogen-C C 6 -alkylcarbonyl; d-Cβ-alkoxycarbonyl; halogen-C C 6 -alkoxycarbonyl; d-C 6 -alkylaminocarbonyl; di-(d-C 6 -alkyl)-aminocarbonyl, whereby the alkyl groups may be identical or different; - Ci-Ce-alkylaminothiocarbonyl; di-(Cι-C 6 -alkyl)-aminothiocarbonyl, whereby the alkyl groups may be identical or different; d-C 6 -alkylamino; di-(C C 6 -alkyl)-amino; N0 2 ; an unsubstituted d-C 4 -alkylendioxy group or one which is mono- to tetrasubstituted by d-d-alkyl and/or halogen; CN; SF 5 ; OCN or C(=NOR 2 )-Z-R 3 ; R 2 and R 3 independently of one another, are hydrogen or C C 6 -alkyl; Z is a direct bond, O, S, NH or N(d-C 6 -alkyl). Formula I is to include all possible isomeric forms and mixtures thereof, e.g. racemic mixtures and any [E/Z] mixtures. Alkyl is either straight-chained, e.g. methyl, ethyl, propyl, butyl, pentyl or hexyl, or branched, e.g. isopropyl, isobutyl, sec. -butyl, tert.-butyl, isopentyl, neopentyl or isohexyl. Alkenyl is either straight-chained, e.g. vinyl, 1 -methylvinyl, allyl, 1 -butenyl or 2-hexenyl, or branched, e.g. isopropenyl. Alkynyl is either straight-chained, e.g. propargyl, 2-butinyl or 5-hexinyl, or branched, e.g. 2-ethinylpropyl or 2-propargylisopropyl. Alkylenedioxy is -0(alkylene)0-. Alkylene is either straight-chained, e.g. -CH 2 CH 2 -, -CH 2 CH 2 CH 2 - or -CH 2 CH 2 CH 2 CH 2 -, or branched, e.g. -CH(CH 3 )-, -CH(C 2 H 5 )-, -C(CH 3 ) 2 -, - CH(CH 3 )CH 2 - or -CH(CH 3 )CH(CH 3 )-. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. Halogenalkyl may contain identical or different halogen atoms. Aryl signifies phenyl or naphthyl, preferably phenyl. Heteroaryl signifies a cyclic aromatic group with 5 to 9 ring members in one or two rings, of which 1 to 3 members are hetero atoms selected from the group oxygen, sulphur and nitrogen. 1 to 2 benzene rings may be condensed on the heterocycie, the binding to the residual molecule taking place either through the hetero or the benzene moiety. Examples are benzimidazolyl, benzisoxazolyl, benzisothiazolyl, benzocumarinyl, benzofuryl, benzothiadiazolyl, benzothiazolyl, benzothienyl, benzoxazolyl, benzoxdiazolyl, quinazolinyl, quinolyl, quinoxalinyl, carbazolyl, dihydrobenzofuryl, furyl, imidazolyl, indazolyl, indolyl, isoquinolinyl, isothiazolyl, isoxazolyl, methylenedioxyphenyl, ethylenedioxyphenyl, naphthyridinyl, oxazolyl, phenanthridinyl, phthalazinyl, pteridinyl, purinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyrazoio[3,4-b]pyridyl, pyridyl, pyrimidinyl, pyrrolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, thiazolyl, thienyl, triazinyl and triazolyl. Preference is given to pyridyl, pyrazinyl, pyrimidinyl, thiazolyl, quinolinyl and thienyl. Heterocyclyl signifies a 5- to 7-membered, non-aromatic ring with one to three hetero atoms selected from the group comprising N, O and S. Preference is given to non-aromatic 5- and 6-rings that have one nitrogen atom as a hetero atom and optionally one further hetero atom. Piperidinyl, morpholinyl, pyrrolidinyl, pyrazolinyl, thiazolinyl and oxazolinyl are preferred. Of the compounds of formula I, those groups are preferred, wherein: (1 ) a) A is the group CH 2 0; or b) A is the group CH 2 ON=C(R 1 ), wherein Rι is CH 3 ; or c) X and X 2 are methyl; or d) Y is OCH 3 or NHCH 3 . In addition, in combination with one of the above-mentioned groups (1 )a to (1 )d, the groups of compounds are preferred in which R has the following significances: (2) phenyl which is unsubstituted or mono- to tri-substituted by identical or different substituents from halogen, Cι-C 6 -alkyl, Cι-C 6 -halogenalkyl, d-C 6 -alkoxy, C C 6 - haloalkoxy, C -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkynyl, C 3 -C 6 -alkynyloxy, d-C 6 - alkoxycarbonyl, cyano or OCN; especially phenyl which is mono- to disubstituted by identical or different substituents from halogen, d-C -alkyl, d-C 2 -haloalkyl, C 1 -C 2 -alkoxy or d-C 2 -haloalkoxy. (3) phenyl which is substituted by C(=NOR 2 )-Z-R 3 ; wherein R 2 and R 3 , independently of each other, signify hydrogen or d-d-alkyl and Z signifies a direct bond. (4) pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, pyrazolinyl, which are unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, cyano, nitro, aminocarbonyl, d-d-alkyl, C C 4 - halogenalkyl, d-d-alkylcarbonyl, d-C 4 -alkylsulfonyl, d-C 6 -alkylsulfoxyl, C 3 -C 6 - cycloalkyl, d-d-alkoxy, d-d-halogenalkoxy, d-C 6 -alkoxycarbonyl, d-C 6 -alkylthio, d-C 6 -alkylamino, di-C C 6 -alkylamino, d-C 6 -alkylaminocarbonyl, di-C C 6 - alkylaminocarbonyl, C 2 -C 6 -alkenyl, C(=NOR 2 )-Z-R 3 or by aryl that is optionally mono- to tπsubstituted by identical or different substituents from d-d-alkyl, halogen, C C 4 - ' alkoxy, d-d-halogenalkyl or cyano; especially pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, pyrazolinyl, which are unsubstituted or mono- to disubstituted by identical or different substituents from halogen, cyano, nitro, methyl, ethyl, halomethyl, haloethyl, methoxy, ethoxy, halomethoxy, haloethoxy, or by phenyl that is optionally mono- to disubstituted by identical or different substituents from d-C 2 -alkyl, halogen, d-C - alkoxy, d-C 2 -halogenalkyl or cyano. Compounds of formula I may be produced as follows: A) A compound of formula I is produced whereby a compound of the general formula II wherein A, R, X X 2 and Y have the significances given for formula I, is reacted with an oxidation agent, such as a quinone, preferably chloranil or DDQ (2,3-dichloro-5,6-dιcyano- 1 ,4-benzoquιnone), atmospheric oxygen, manganese dioxide, selenium dioxide, N,N,N',N'- tetramethyl ethylenediamine/base or tπphenylmethanol in trifluoroacetic acid. The compounds of the general formula II are known (WO 97/47592 and WO 97/49672) or may be produced by the methods described therein. B) A compound of formula I, wherein Y is OH, NH 2 or NHCH 3 and A, R, Xi and X 2 have the significances given for formula I, are produced whereby a compound of formula la wherein Y signifies 0(C C 4 alkyl) and A, R, X^ and X 2 have the significances given for formula I, is reacted with an aqueous acid or base, or with NH or with NH CH 3 . C) A compound of formula I, wherein Y signifies O(d-d-alkyl) or NHCH 3 , is produced whereby a compound of formula III, wherein U is a leaving group, for example chlorine, bromine, iodine, OH, mesyloxy, benzenesulphonyloxy or tosyloxy, preferably chlorine or bromine, and the remaining substituents have the above-mentioned significances, is reacted with an alcohol of the general formula IV, or with an oxime of the general formula V, R-OH IV R(R,)C=NOH V wherein R and R, have the significances given for formula D) A compound of formula I is produced whereby a compound of formula VI, wherein the substituents have the significances given for formula I, is reacted with a methylation agent, e.g. methyl iodide or dimethyl sulphate. A compound of formula VI is produced, whereby either a) a compound of formula VII, wherein the substituents have the significances given for formula I, is reacted with hydroxylamine or with one of its salts, or F) a compound of formula VIII, wherein the substituents have the significances given for formula I, is reacted with nitrous acid or with an alkyl nitrite. G) A compound of formula I, wherein A is the group CH 2 ON=CRι and the remaining substituents have the significances given for formula I, is produced whereby a compound of formula IX, is reacted with a compound of formula R CO-R, wherein the substituents have the significances given for formula I All the above-described reactions are known perse. The process for the production of the compounds of formula I, as well as the new intermediates of formulae III, VI, VII, VIII and IX likewise form objects of the invention. The said intermediates may be produced by reacting the corresponding (analogous to formula II) 1 ,4-cyciohexadιene derivative with an oxidation agent, such as a quinone, preferably chloranil or DDQ (2,3-dιchloro-5,6-dιcyano-1 ,4-benzoquιnone), atmospheric oxygen, manganese dioxide, selenium dioxide, N,N,N',N'-tetramethyl ethylenediamine/base or tπphenylmethanol in tnfluoroacetic acid. The corresponding 1 ,4-cyclohexadιene derivatives are known (WO 97/47592 and WO 97/49672) or may be produced by the methods described therein. The compounds of formula I are of preventive and/or curative merit as active ingredients for the control of plant pests and may be used in the agricultural sector and related fields The active ingredients of formula I according to the invention are notable for their good activity even at low concentrations, for their good plant tolerance and for their environmental acceptability. They possess very advantageous, especially systemic properties, and may be used for the protection of numerous cultivated plants. Using the active ingredients of formula I, pests appearing on plants or plant parts (fruits, flowers, foliage, stems, tubers, roots) of various crops can be checked or destroyed, whereby parts of the plant which grow later are also protected e.g. from phytopathogenic micro-organisms The compounds of formula I may also be be employed as a dressing for seeds (fruits, tubers, grain) and plant cuttings to protect against fungal infections, and to protect against phytopathogenic fungi appearing in the soil Compounds I are effective for example against the phytopathogenic fungi belonging to the following classes Fungi imperfecti (e g. Botrytis, Pyπcularia, Helminthospoπum, Fusarium, Septoπa, Cercospora and Alternana), Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia), Ascomycetes (e.g Ventuna and Erysiphe, Podosphaera, Monilinia, Uncinula) and Oomycetes (e g Phytophthora, Pythium, Plasmopara) Target cultivations for the plant-protecting usage in the context of the invention are, for example, the following species of plant cereals, (wheat, barley, rye, oats, rice, corn, sorghum and related species), beet (sugar beet and fodder beet), pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries), leguminous plants (beans, lentils, peas, soybean); oleaginous fruits (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (squashes, cucumbers, melons); fibrous plants (cotton, flax, hemp, jute); citrus fruits (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika), Lauraceae (avocado, cinnamon, camphor), and plants such as tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, banana plants, natural rubber plants and ornamentals. Further fields of application for the active ingredients according to the invention are the protection of stock and material, where the goods stored are protected against rotting and mildew Compounds I are used in this instance in unmodified form or preferably together with the excipients that are usual in formulation technology To this end, they are suitably processed in known manner e g into emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dusts or granules, e g by encapsulation in e.g. polymeric substances. As with the type of compositions, the methods of application, such as spraying, atomizing, dusting, scattering, coating or pouring, are selected in accordance with the intended objectives and the prevailing circumstances Suitable carriers and additives may be solid or liquid and are substances that are appropriate in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binding agents or fertilisers The compounds of formula I may be mixed with further active ingredients, e g. fertilisers, trace element intermediates or other plant-protecting compositions, especially with further fungicides Unexpected synergistic effects may thus occur Preferred mixture components are azoles, such as azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutπafol, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, pyπfenox, prochloraz, propiconazole, tebuconazole, tetraconazole, tπadimefon, tnadimenol, tπflumizole, tπticonazole, pyrimidinyl carbinols, such as ancymidol, fenaπmol, nuaπmol, 2-amιnopyrιmιdιnes, such as bupiπmate, dimethiπmol, ethiπmol; morphoiines, such as dodemorph, fenpropidin, fenpropimorph, spiroxamin, tndemorph; anilinopyπmidines, such as cyprodinil, mepanipyπm, pyπmethanil; pyrroles, such as fenpiclonil, fludioxonil, phenylamides, such as benalaxyl, furalaxyl, metalaxyl, R-metataxyl, ofurace, oxadixyl, benzimidazoles, such as benomyl, carbendazim, debacarb, fubeπdazole, thiabendazole, dicarboximides, such as chlozolinate, dichlozoime, iprodione, myclozohne, procymidone, vinclozolin, carboxamides, such as carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, thifluzamide; guanidines, such as guazatine, dodme, iminoctadine, strobiluπnes, such as azoxystrobin, kresoxim-methyl, SSF-126 (metominostrobin or fenominostrobin, SSF-129 ( -methoxιmιno-N-methyl-2-[(2,5-dιmethylphenoxy)methyl]- benzeneacetamide), trifloxystrobin (2-[α-{[(α-methyl-3-tπfluoromethyl-benzyl)ιmιno]-oxy}-o- tolyl] -glyoxylic acid methylester-O-methyloxime), dithiocarbamates, such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zmeb,- ziram, N-halomethylthio, such as captafol, captan, dichlofluanid, fluoromide, folpet, tolyfluanide; Cu compounds, such as Bordeaux mixture, copper hydroxide, copper oxychloπde, copper sulphate, cuprous oxide, mancopper, oxine-copper; nitrophenol derivatives, such as dinocap, nitrothal-isopropyl; organo-P derivatives, such as edifenphos, iprobenphos, isoprothiolane, phosdiphen, pyrazophos, tolclofos-methyl, miscellaneous, such as acibenzolar-S-methyl, anilazine, blasticidin-S, quinomethionat, chloroneb, chlorothalonil, cymoxanil, dichlone, diclomezine, dicloran, diethofencarb, dimethomorph, dithianon, etπdiazole, famoxadone, fentin, feπmzone.fluazinam, flusulfamide, fenhexamid, fosetyl-aluminium, hymexazol, kasugamycin, methasulfocarb, pencycuron, phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxyfen, quintozene, sulphur, tπazoxide, tπcyclazole, trifonne, validamycin One preferred method of applying an active ingredient of formula I or an agrochemical composition containing at least one of these active ingredients is application to the foliage (leaf application) The frequency and rate of application depend on the severity of infestation by the invader in question. However, the active ingredients I can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plants with a liquid preparation, or by applying the substances to the soil in solid form, for example in granular form (soil application) With paddy rice cultures, granules may be metered into the flooded paddy field. The compounds I may also be applied to seed gram for seed pretreatment (coating) by either drenching the grains or tubers in a liquid preparation of the active ingredient or coating them with a solid preparation The compositions are prepared in known manner, e.g. by intimately mixing and/or grinding the active ingredient with extenders, such as solvents, solid carriers and optionally surface- active compounds (surfactants) The agrochemical compositions normally contain 0.1 to 99 percent by weight, especially 0.1 to 95 percent by weight, of active ingredient of formula I, 99 9 to 1 percent by weight, especially 99.8 to 5 percent by weight, of a solid or liquid additive and 0 to 25 percent by weight, especially 0 1 to 25 percent by weight, of a surfactant. Favourable application rates generally lie between 1 g and 2 kg of active substance (AS) per hectare (ha), preferably between 10 g and 1 kg AS/ha, especially between 20 g and 600 g AS/ha For usage as a seed dressing, the dosages advantageously used are 10 mg to 1 g of active substance per kg seeds. The compositions may also contain further additives, such as stabilisers, anti-foaming agents, viscosity regulators, binding agents or tackifiers, as well as fertilizers or other active ingredients, in order to achieve special effects. Preparation examples P-1 ) (4,5-dιmethyl-2-f 1 -(3-trιfluoromethyl-phenyl)-ethylιdene-amιno-oxymethyll-phenyl)- methoxyimino-acetic acid methylester A solution of 3 15 g of {4,5-dιmethyl-2-[1 -(3-trιfluoromethyl-phenyl)-ethylιdene-amιno- oxymethyl]-cyclohexa-1 ,4-dιenyl}-methoxyιmιno-acetιc acid methylester (as an E/Z-mixture in respect of the ethylidene-aminooxy double bond) in 40 ml of toluene is mixed with 2.0 g of 2,3-dιchlor-5,6-dιcyano-1 ,4-benzoquιnone (DDQ), whereby a slight exothermic reaction is observed After stirring for 4 hours at room temperature, the reaction mixture is filtered through Hyflo and the solvent is distilled off on a rotary evaporator. After purifying with diethyl ether/hexane (1 :3) on silica gel, 2.6 g of the title compound are obtained as a yellowish oil P-2) 2-{4,5-dιmethyl-2-[1 -(3-trιfluoromethyl-phenyl)-ethylιdene-amιno-oxymethvn-phenyl)-2- methoxyimino-N-methyl-acetamide A solution of 2 1 g of the ester obtained in P-1 in 10 ml of ethanoiic methylamine (8.03 molar) is stirred over night at room temperature After distilling off the excess methylamine and the solvent, 2.0 g of the title compound are obtained in the form of a slightly yellow crystal powder having a melting range of 129-134°C (E/Z mixture). P-3) (4,5-dιmethyl-2-o-tolyloxymethyl-phenyl)-methoxyιmιno-acetιc acid methylester A solution of 1.3 g of (4,5-dιmethyl-2-o-tolyloxymethyl-cyclohexa-1 ,4-dιenyl)-methoxyιmιno- acetic acid methylester in 15 ml of toluene is mixed with 1.1 g of DDQ. After stirring for 5 hours at room temperature, the reaction mixture is purified using toluene/hexane/- dnsopropylether (10.10:3) on silica gel. After stirring in hexane, the title compound is obtained in the form of white crystals having the melting point 82-84°C The compounds of the following tables may be produced in analogous manner Table 1 Compounds of the general formula 1.1 , in which Y signifies methoxy and R corresponds in each case to one line of Table A. Table 2 Compounds of the general formula I 1 , in which Y signifies ethoxy and R corresponds in each case to one line of Table A. Table 3 Compounds of the general formula I 1 , in which Y signifies NHCH 3 and R corresponds in each case to one line of Table A Table 4 Compounds of the general formula I 2, in which Ri signifies methyl and Y signifies methoxy and R corresponds in each case to one line of Table A. Table 5 Compounds of the general formula 1.2, in which Rj signifies methyl and Y signifies ethoxy and R corresponds in each case to one line of Table A. Table 6 Compounds of the general formula I.2, in which R T signifies methyl and Y signifies NHCH 3 and R corresponds in each case to one line of Table A. Table 7 Compounds of the general formula 1.2, in which R T signifies ethyl and Y signifies methoxy and R corresponds in each case to one line of Table A. Table 8 Compounds of the general formula 1.2, in which R^ signifies ethyl and Y signifies ethoxy and R corresponds in each case to one line of Table A. Table 9 Compounds of the general formula 1.2, in which R T signifies ethyl and Y signifies NHCH 3 and R corresponds in each case to one line of Table A. Table 10 Compounds of the general formula 1.2, in which Ri signifies cyclopropyl and Y signifies methoxy and R corresponds in each case to one line of Table A. Table 11 Compounds of the general formula 1.2, in which Ri signifies cyclopropyl and Y signifies ethoxy and R corresponds in each case to one line of Table A. Table 12 Compounds of the general formula 1.2, in which Ri signifies cyclopropyl and Y signifies NHCH 3 and R corresponds in each case to one line of Table A. Table 13 Compounds of the general formula I.2, in which R, signifies methoxy and Y signifies methoxy and R corresponds in each case to one line of Table A. Table 14 Compounds of the general formula I.2, in which Ri signifies methoxy and Y signifies ethoxy and R corresponds in each case to one line of Table A. Table 15 Compounds of the general formula I.2, in which Ri signifies methoxy and Y signifies NHCH 3 and R corresponds in each case to one line of Table A. Table 16 Compounds of the general formula 1.2, in which Ri signifies cyano and Y signifies methoxy and R corresponds in each case to one line of Table A. Table 17 Compounds of the general formula 1.2, in which Ri signifies cyano and Y signifies ethoxy and R corresponds in each case to one line of Table A. Table 18 Compounds of the general formula 1.2, in which Ri signifies cyano and Y signifies NHCH 3 and R corresponds in each case to one line of Table A. Table 19 Compounds of the general formula 1.2, in which Ri signifies trifluoromethyl and Y signifies methoxy and R corresponds in each case to one line of Table A Table 20 Compounds of the general formula 1.2, in which Ri signifies trifluoromethyl and Y signifies ethoxy and R corresponds in each case to one line of Table A. Table 21 Compounds of the general formula 1.2, in which Ri signifies trifluoromethyl and Y signifies NHCH 3 and R corresponds in each case to one line of Table A. Table A No. R No. R 1 . Phenyl 27. 3,4,5-CI 3 -C 6 H 2 2. 1 -Naphthyl 28. 2-Br-C 6 H 4 3. 2-Naphthyl 29. 3-Br-C 6 H 4 4. 2-F-C 6 H 4 30. 4-Br-C 6 H 4 5. 3-F-CeH 4 31 . 2,3-Br 2 -C 6 H 3 6. 4-F-C 6 H 4 32. 2,4-Br 2 -C 6 H 3 7. 2,3-F 2 -C 6 H 3 33. 2,5-Br 2 -CeH 3 8. 2,4-F 2 -C 6 H 3 34. 2,6-Br 2 -C 6 H 3 9. 2,5-F 2 -C 6 H 3 35. 3,4-Br 2 -C 6 H 3 10. 2,6-F 2 -C 6 H 3 36. 3,5-Br 2 -CeH 3 1 1 . 3,4-F 2 -C 6 H 3 37. 2-F-3-CI-C 6 H 3 12. 3,5-F 2 -C 6 H 3 38. 2-F-4-CI-C 6 H 3 13. 2-CI-C 6 H 4 39. 2-F-5-CI-C 6 H 3 14. 3-CI-C 6 H 4 40. 2-F-3-Br-C 6 H 3 15. 4-CI-C 6 H 4 41 . 2-F-4-Br-C 6 H 3 16. 2,3-CI 2 -C 6 H 3 42. 2-F-5-Br-C 6 H 3 17. 2,4-CI 2 -C 6 H 3 43. 2-CI-3-Br-C 6 H 3 18. 2,5-Ci 2 -C 6 H 3 44. 2-CI-3-Br-C 6 H 3 19. 2,6-CI 2 -C 6 H 3 45. 2-CI-5-Br-C 6 H 3 20. 3,4-CI 2 -C 6 H 3 46. 3-F-4-CI-C 6 H 3 21 . 3,5-CI 2 -C 6 H 3 47. 3-F-5-CI-C 6 H 3 22. 2,3,4-CI 3 -C 6 H 2 48. 3-F-6-CI-C 6 H 3 23. 2,3,5-CI 3 -C 6 H 2 49. 3-F-4-Br-C 6 H 3 24. 2,3,6-CI 3 -C 6 H 2 50. 3-F-5-Br-C 6 H 3 25. 2,4,5-CI 3 -C 6 H 2 51 . 3-F-6-Br-C 6 H 3 26. 2,4,6-CI 3 -C 6 H 2 52. 3-CI-4-Br-C 6 H 3 No. R No. R 53. 3-CI-5-Br-C 6 H 3 85. 3-(i-C 3 H 7 0)-C 6 H 4 54. 3-CI-6-Br-C 6 H 3 86. 4-(i-C 3 H 7 0)-C 6 H 4 55. 4-F-5-CI-C 6 H 3 87. 4-(n-C 4 H 9 0)-C 6 H 4 56. 4-F-6-CI-C 6 H 3 88. 3-(t-C 4 H 9 0)-C 6 H 4 57. 4-F-5-Br-C 6 H 3 89. 4-(t-C 4 H 9 0)-C 6 H 4 58. 4-F-6-Br-C 6 H 3 90. 2 -Allyl-0-C 6 H 4 59. 4-CI-5-Br-C 6 H 3 91. 3-Allyl-0-C 6 H 4 60. 5-F-6-Cl-C 6 H 3 92. 4-Allyl-0-C 6 H 4 61 . 5-F-6-Br-C 6 H 3 93. 2-CF 3 -C 6 H 4 62. 5-CI-6-Br-C 6 H 3 94. 3-CF 3 -C 6 H 4 63. 3-Br-4-CI-5-Br-C 6 H 2 95. 4-CF 3 -C 6 H 4 64. 2-CN-C 6 H 4 96. 2-Acetyl-C 6 H 4 65. 3-CN-C 6 H 4 97. 3-Acetyl-C 6 H 4 66. 4-CN-C 6 H 4 98. 4-Acetyl-C 6 H 4 67. 3-OCN-C 6 H 4 99. 2-Methoxycarbonyl-C 6 H 4 68. 4-OCN-C 6 H 4 100. 3-Methoxycarbonyl-C 6 H 4 69. 2-CH 3 0-C 6 H 4 101 . 4-Methoxycarbonyl-C 6 H 4 70. 3-CH 3 0-C 6 H 4 102. 2-Aminocarbonyl-C 6 H 4 71 . 4-CH 3 0-C 6 H 4 103. 3-Aminocarbonyl-C 6 H 4 72. 2,3-(CH 3 0) 2 -C 6 H 3 104. 4-Aminocarbonyl-C 6 H 4 73. 2,4-(CH 3 0) 2 -C 6 H 3 105. 2-Dimethylaminocarbonyl-C 6 H 4 74. 2,5-(CH 3 0) 2 -C 6 H 3 106. 3-Dimethylaminocarbonyl-C 6 H 4 75. 3,4-(CH 3 0) 2 -C 6 H 3 107. 4-Dimethylaminocarbonyl-C 6 H 4 76. 3,5-(CH 3 0) 2 -C 6 H 3 108. 2-(Methylaminocarbonyl)-C 6 H 4 77. 3,4,5-(CH 3 0) 3 -C 6 H 2 109. 3-(Methylaminocarbonyl)-C 6 H 4 78. 2-C 2 H 5 0-C 6 H 4 1 10. 4-(Methylaminocarbonyl)-C 6 H 4 79. 3-C 2 H 5 0-C 6 H 4 111 . 2-CH 3 S-C 6 H 4 80. 4-C 2 H 5 0-C 6 H 4 112. 3-CH 3 S-C 6 H 4 81. 2- (n-C 3 H 7 0)-C 6 H 4 1 13. 4-CH 3 S-C 6 H 4 82. 3-(n-C 3 H 7 0)-C 6 H 4 114. 2-CH 3 S0 2 -C 6 H 4 83. 4-(n-C 3 H 7 0)-C 6 H 4 115. 3-CH 3 S0 2 -C 6 H 4 84. 2-(i-C 3 H 7 0)-C 6 H 4 116. 4-CH 3 S0 2 -C 6 H 4 No. R No. R 1 17. 2-CF 3 0-C 6 H 4 149. 3-CH 3 -C- 6 H 4 1 18. 3-CF 3 0-C 6 H 4 150. 4-CH 3 -C 6 H 4 1 19. 4-CF 3 0-C 6 H 4 151 . 2,3-(CH 3 ) 2 -CeH 3 120. 2-CHF 2 0-C 6 H 4 152. 2,4-(CH 3 ) 2 -C 6 H 3 121 . 3-CHF 2 0-C 6 H 4 153. 2,5-(CH 3 ) 2 -CeH 3 122. 4-CHF 2 0-C 6 H 4 154. 2,6-(CH 3 ) 2 -CeH 3 123. 3-CF 3 -4-CF 3 0-C 6 H 3 155. 3,4-(CH 3 ) 2 -C 6 H 3 124. 2-CH 3 NH-C 6 H 4 156. 3,5-(CH 3 ) 2 -C 6 H 3 125. 3-CH 3 NH-C 6 H 4 157. 2-C 2 H 5 -CβH 126. 4-CH 3 NH-C 6 H 4 158. 3-C 2 H 5 -CeH 127. 2-(CH 3 ) 2 N-C 6 H 4 159. 4-C2H5-C 6 H 4 128. 3-(CH 3 ) 2 N-C 6 H 4 160. 2-i-C 3 H 7 -CeH 4 129. 4-(CH 3 ) 2 N-C 6 H 4 161 . 3-i-C 3 H 7 -CeH 130. 2-Ethoxycarbonyl-C 6 H 162. 4-i-C 3 H 7 -C 6 H 4 131. 3-Ethoxycarbonyl-C 6 H 4 163. 3-tert.-C 4 H 9 -C 6 H 4 132. 4-Ethoxycarbonyl-C 6 H 4 164. 4-tert.-C 4 H 9 -C 6 H 4 133. 2-CH 2 FCH 2 -C 6 H 4 165. 2Ninyl-C 6 H 4 134. 3-CH2FCH 2 -C 6 H 4 166. 3 /inyl-C 6 H 4 135. 4-CH 2 FCH 2 -C 6 H4 167. 4-Vinyl-C 6 H 4 136. 2-CF 3 CH 2 -C 6 H 4 168. 2-Allyl-C 6 H 4 137. 3-CF 3 CH 2 -C 6 H 4 169. 3-Allyl-C 6 H 4 138. 4-CF 3 CH 2 -C 6 H 4 170. 4-Allyl-C 6 H 4 139. 2-CHF 2 CF 2 -CeH 4 171 . 2-Propargyl-C 6 H 4 140. 3-CHF 2 CF 2 -CeH 4 172. 2-Ethinyl-C 6 H 4 141 . 4-CHF 2 CF 2 -C 6 H 4 173. 3-Propargyloxy-C 6 H 4 142. 2-CHF 2 -C 6 H 4 174. 4-Butinyloxy-C 6 H 4 143. 3-CHr 2 -CeH 4 175. 2-C 6 H 5 -C 6 H 4 144. 4-CHF 2 -C 6 H 4 176. 3-C6H5-CΘH 4 145. 2-N0 2 -C 6 H 4 177. 4-C 6 H 5 -C 6 H 4 146. 3-N0 2 -C 6 H 4 178. 3-CH 3 -5-t-C 4 H 9 -C 6 H 3 147. 4-N0 2 -C 6 H 4 179. 2-F-4-CH 3 -C 6 H 3 148. 2-CH 3 -CeH 4 180. 2-F-5-CH 3 -C 6 H 3 No. R No. R 245. 5-Pyrimidinyl 277. 5-CH 3 -Oxazol-2-yl 246. 2-CH 3 -Pyrimidin-5-yl 278. 5-CI-Oxazol-2-yl 247. 2-CI-Pyrimidin-5-yl 279. 5-CN-Oxazol-2-yl 248. 2-CH 3 0-Pyrimidin-5-yl 280. 4-Oxazolyl 249. 2-C 2 H 5 0-Pyrimidin-5-yl 281. 2-CH 3 -Oxazol-4-yl 250. 2-Furyl 282. 2-CI-Oxazol-4-yl 251. 4-C 2 H 5 -Fur-2-yl 283. 2-CN-Oxazol-4-yl 252. 4-CH 3 -Fur-2-yl 284. 5-Oxazolyl 253. 4-CI-Fur-2-yl 285. 2-CH 3 -Oxazol-5-yl 254. 4-CN-Fur-2-yl 286. 2-CI-Oxazol-5-yl 255. 5-CH 3 -Fur-2-yl 287. 2-CN-Oxazol-5-yl 256. 5-CI-Fur-2-yl 288. 3-lsoxazolyl 257. 5-CN-Fur-2-yl 289. 5-CH 3 -lsoxazol-3-yl 258. 3-Furyl 290. 5-CI-lsoxazol-3-yl 259. 5-CH 3 -Fur-3-yl 291 . 5-CN-lsoxazol-3-yl 260. 5-CI-Fur-3-yl 292. 5-lsoxazolyl 261. 5-CN-Fur-3-yl 293. 3-CH 3 -lsoxazol-5-yl 262. 2-Thienyl 294. 3-CI-lsoxazol-5-yl 263. 4-CH 3 -Thien-2-yl 295. 3-CN-lsoxazol-5-yl 264. 4-CI-Thien-2-yl 296. 2-Thiazolyl 265. 4-CN-Thιen-2-yl 297. 4-CH 3 -Thiazol-2-yl 266. 5-CH 3 -Thιen-2-yl 298. 4-CI-Thiazol-2-yl 267. 5-CI-Thien-2-yl 299. 4-CN-Thiazol-2-yl 268. 5-CN-Thien-2-yl 300. 5-CH 3 -Thiazol-2-yl 269. 3-Thienyl 301 . 5-CI-Thiazol-2-yl 270. 5-CH 3 -Thien-3-yl 302. 5-CN-Thiazol-2-yl 271. 5-CI-Thien-3-yl 303. 4-Thiazolyl 272. 5-CN-Thien-3-yl 304. 2-CH 3 -Thiazol-4-yl 273. 2-Oxazolyl 305. 2-CI-Thiazol-4-yl 274. 4-CH 3 -Oxazol-2-yl 306. 2-CN-Thiazol-4-yl 275. 4-CI-Oxazol-2-yl 307. 2-CH 3 S-Thiazol-4-yl 276. 4-CN-Oxazol-2-yl 308. 5-Thiazolyl No. R No. R 309. 2-CH 3 -Thiazol-5-yl 341 . 5-CN-Pyrazol-3-yl 310. 2-CI-Thiazol-5-yl 342. 1 -(4-Chlorphenyl)-pyrazol-3-yl 31 1 . 2-CN-Thiazol-5-yl 343. 1 -(4-Methylphenyl)-pyrazol-3-yl 312. 3-lsothiazolyl 344. 1 -CH 3 -Pyrazol-3-yl 313. 5-CH 3 -lsothiazol-3-yl 345. 1 -CH 3 -4-CI-Pyrazol-3-yl 314. 5-CI-lsothiazol-3-yl 346. 1 -CH 3 -5-CI-Pyrazol-3-yl 315. 5-CN-lsothiazol-3-yl 347. 1 ,5-(CH 3 ) 2 -Pyrazol-3-yl 316. 5-lsothiazolyl 348. 1 -CH 3 -Pyrazol-5-yl 317. 3-CH 3 -lsothiazol-5-yl 349. 1 -CH 3 -3-CI-Pyrazol-5-yl 318. 3-CI-lsothiazol-5-yl 350. 1 ,3-(CH 3 ) 2 -Pyrazol-5-yl 319. 3-CN-lsothiazol-5-yl 351 . 4-Pyrazolyl 320. 2-lmidazolyl 352. 3-CI-Pyrazol-4-yl 321 . 4-CH 3 -lmidazol-2-yl 353. 3-CH 3 -Pyrazol-4-yl 322. 4-CI-lmidazol-2-yl 354. 1 -CH 3 -Pyrazol-4-yl 323. 4-CN-imidazol-2-yl 355. 1 -CH 3 -3-CI-Pyrazol-4-yl 324. 1 -CH 3 -lmidazol-2-yl 356. 1 -(4-Chlorphenyl)-pyrazol-4-yl 325. 1 -CH 3 -4-CI-lmidazol-2-yl 357. 1 -(4-Methylphenyl)-pyrazol-4-yl 326. 1 ,4-(CH 3 ) 2 -lmidazol-2-yl 358. 1 ,3-(CH 3 ) 2 -Pyrazol-4-yl 327. 1 -CH 3 -5-CI-lmidazol-2-yl 359. 1 ,3,4-Oxadiazol-5-yl 328. 1 ,5-(CH 3 ) 2 -lmidazol-2-yl 360. 2-CH 3 -1 ,3,4-Oxadiazol-5-yl 329. 4-lmidazolyl 361 . 2-CI-1 ,3,4-Oxadiazol-5-yl 330. 2-CH 3 -lmidazol-4-yl 362. 2-CF 3 -1 ,3,4-Oxadiazol-5-yl 331. 2-Cl-lmidazol-4-yl 363. 2-i-C 3 H 7 -1 ,3,4-Oxadiazol-5-yl 332. 1 -CH 3 -lmidazol-4-yl 364. 2-CH 3 0-1 ,3,4-Oxadiazol-5-yl 333. 1 ,2-(CH 3 ) 2 -lmidazol-4-yl 365. 1 ,2,4-Oxadiazol-3-yl 334. 1 -CH 3 -2-CI-lmidazol-4-yl 366. 5-CH3-1 ,2,4-Oxadiazol-3-yl 335. 1 -CH 3 -lmidazol-5-yl 367. 5-i-C 3 H 7 -1 ,2,4-Oxadiazol-3-yl 336. 1 -CH 3 -3-CI-lmidazol-5-yl 368. 5-CI-1 ,2,4-Oxadiazol-3-yl 337. 1 ,2-(CH 3 ) 2 -lmidazol-5-yl 369. 5-CF 3 -1 ,2,4-Oxadiazol-3-yl 338. 3-Pyrazolyl 370. 1 ,2,4-Triazol-3-yl 339. 5-CH 3 -Pyrazol-3-yl 371 . 1 -CH 3 -1 ,2,4-Triazol-3-yl 340. 5-CI-Pyrazol-3-yl 372. 1 -Pyrrolyl No. R No. R 373. 3-CH 3 -Pyrrol-1-yl 401. 374. 1-Pyrazolyl 375. 3-CH 3 -Pyrazol-1-yl 376. 3-CF 3 -Pyrazol-1-yl 402. 377. 4-CH 3 -Pyrazol-1-yl 378. 4-CI-Pyrazol-1-yl 379. 4-Ethoxycarbonyl-Pyrazol-1 -yl 380. 3-CH 3 -4-Br-Pyrazol-1-yl 381. 1-lmidazolyl 403. 1 -(4-Chlorphenyl)- Δ -pyrazolin-3-yl 382. 4-CH 3 -lmidazol-1-yl 404. 1 -(4-Methylphenyl)- Δ 2 -pyrazolin-3-yl 383. 4,5-CI 2 -lmidazol-1-yl 405. 4-l-C 6 H 4 384. 2,4-(CH 3 )-lmidazol-1-yl 406. 3-Ethinyl-C 6 H 4 385. 1,2,4-Triazol-l-yl 407. 4-Br-2-CH 3 0-C 6 H 3 386. 1,3,4-Triazol-1-yl 408. 4-Ethinyl-2-CH 3 0-C 6 H 3 387. 3,5-(CH 3 )-1,2,4-Triazol-1-yl 388. 1 -(4-Chlorophenyl)-1 ,2,4-triazol-3-yl 389. 1 -(4-Methylphenyl)-1 ,2,4-triazol-3-yl 390. 1-Piperidinyl 391. 1-Pyrrolidinyl 392. 1-Morpholinyl 393. 2-Δ'-Thiazolinyl 394. 5-CH 3 -Δ 2 -Thiazolin-2-yl 395. 5,5-(CH 3 ) 2 -Δ 2 -Thiazolin-2-yl 396. 4,5-(CH 3 ) 2 -Δ-Thiazolin-2-yl 397. 2-Δ 2 -Oxazolinyl 398. 4-CH 3 -Δ 2 -Oxazolin-2-yl 399. 4,4-(CH 3 ) 2 -Δ 2 -Oxazolin-2-yl Details of the physical data in the following Tables: °C = m.p. in °Celsius; Number = chemical displacement of the CH 2 0 group in 1 H-NMR (.δ.in ppm); * isomers Table B: Compounds of formula No. Y R phys. data 1 .1 OCH 3 Phenyl 68-70° 1 .3 OCH3 2-Naphthyl 132-134° 1 .4 OCH 3 2-F-C 6 H 4 resin 1 .6 OCH 3 4-F-C 6 H 4 resin 1 .8 OCH3 2,4-F 2 -C 6 H 3 104-106° 1 .13 OCH3 2-CI-Phenyl 108-1 10°C 1 .17 OCH3 2,4-CI 2 -C 6 H 3 1 18-120° 1 .30 OCH3 4-Br- C 6 H 4 resin 1 .91 OCH3 3-Allyl-0-C 6 H 4 resin 1 .94 OCH 3 3-CF 3 -CeH 4 resin 1 .148 OCH3 2-CH 3 -Phenyl 82-84°C 1 .152 OCH 3 2,3-(CH 3 ) 2 -C 6 H 4 resin 1 .405 OCH 3 4-l-C 6 H 4 105-107° 1 .406 OCH 3 3-Ethinyl-C 6 H 4 resin 1 .407 OCH3 4-Br-2-CH 3 -0-C 6 H 3 resin 1.408 OCH3 4-Ethinyl-2-CH 3 - ■ 0-C 6 H 3 resin 3.13 NHCH 3 2-CI-Phenyl 148-150°C 3.407 NHCH 3 4-Br-2-CH 3 -0-C 6 H 3 134-135° 3.408 NHCH 3 4-Ethinyl-2-CH 3 - -0-C 6 H 3 160-170° Table C: Compounds of formula No. Y Ri R phys. data 4.94 OCH 3 CH 3 3-CF 3 -Phenyl 5.08/5.41 * (3:2) 6.94 NHCH 3 CH 3 3-CF 3 -Phenyl 129-134 °C * Table 22: Intermediates of formula No. Y R phys. data 22.1. OCH 3 Cl 22.2. OCH 3 Br 22.3. OCH 2 CH 3 Cl 22.4. NHCH 3 Cl Formulations may be prepared analogously to those described for example in WO 97/33890. Bioloqical Examples In the following patho-systems, compounds from the tables display good activity. Example B-1 Activity against Puccinia graminis on wheat a) Residual protective action 6 days after planting, wheat plants are sprayed to drip point with an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.02% active substance), and 24 hours later they are infected with a uredospore suspension of the fungus After an incubation period of 48 hours (conditions: 95 to 100 percent relative humidity at 20°), the plants are placed in a greenhouse at 22°. 12 days after infection, the fungal attack is evaluated b) Systemic action 5 days after planting, an aqueous spray mixture prepared from a wettable powder of the active ingredient (0 006% active substance, based on soil volume) is poured onto wheat plants Care is taken that the spray mixture does not come into contact with the parts of the plants that are above ground 48 hours later, the plants are infected with a uredospore suspension of the fungus. After an incubation period of 48 hours (conditions- 95 to 100 percent relative humidity at 20°), the plants are placed in a greenhouse at 22° 12 days after infection, the fungal attack is evaluated. Example B-2 Activity against Phytophthora infestans on tomatoes a) Residual protective action After cultivating for three weeks, tomato plants are sprayed to drip point with an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.02% active substance), and 24 hours later they are infected with a sporangia suspension of the fungus Evaluation of the fungal attack takes place 5 days after infection, during which time conditions of 90 to 100 percent relative humidity and a temperature of 20° are maintained. b) Systemic action After cultivating for three weeks, an aqueous spray mixture prepared from a wettable powder of the active ingredient (0 006% active substance, based on soil volume) is poured onto tomato plants. Care is taken that the spray mixture does not come into contact with the parts of the plants that are above ground. 48 hours later, the plants are infected with a sporangia suspension of the fungus. Evaluation of the fungal attack takes place 5 days * after infection, during which time conditions of 90 to 100 percent relative humidity and a temperature of 20° are maintained. Example B-3" Residual protective action against Cercospora arachidicola on peanuts Peanut plants of 10 to 15 cm height are sprayed to drip point with an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.02% active substance), and 48 hours later they are infected with a conidia suspension of the fungus The plants are incubated for 72 hours at 21 ° and at high humidity, and then placed in a greenhouse until the typical leaf spots appear Evaluation of the activity of the active substance is made 12 days after infection and is based on the number and size of leaf spots Example B-4 Activity against Plasmopara viticola on grapevines Vine seedlings at the 4 to 5 leaf stage are sprayed to drip point with an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.02% active substance), and 24 hours later they are infected with a sporangia suspension of the fungus. Evaluation of the fungal attack takes place 6 days after infection, during which time conditions of 95 to 100 percent relative humidity and a temperature of 20° are maintained. Example B-5 Activity against Colletotnchum lagenaπum on cucumbers After cultivating for 2 weeks, cucumber plants are sprayed with an aqueous spray mixture prepared from a wettable powder of the active ingredient (concentration 0.002%). After 2 days, the plants are infected with a spore suspension (1.5x10 5 spores/ml) of the fungus, and incubated for 36 hours at 23°C and at high humidity. Incubation then continues at normal humidity and at ca. 22°C. The fungal attack that has set in is evaluated 8 days after infection Example B-6 Residual protective action against Ventuna inaequalis on apples Apple cuttings with new shoots 10 to 20 cm in length are sprayed to drip point with an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.02% active substance), and 24 hours later they are infected with a conidia suspension of the fungus. The plants are incubated for 5 days at 90 to 100 percent relative humidity and placed in a greenhouse for a further 10 days at 20 to 24°. 12 days after infection, the fungal attack is evaluated. Example B-7- Activity against Erysiphe graminis on barley a) Residual protective action Barley plants of approximately 8 cm height are sprayed to drip point with an aqueous spray mixture prepared from a wettable powder of the active ingredient (0.02% active substance), and 3 to 4 hours later they are dusted with conidia of the fungus The infected plants are placed in a greenhouse at 22°. 12 days after infection, the fungal attack is evaluated. b) Systemic action An aqueous spray mixture prepared from a wettable powder of the active ingredient (0 002% active substance, based on soil volume) is poured onto barley plants of approximately 8 cm height. Care is taken that the spray mixture does not come into contact with the parts of the plants that are above ground. 48 hours later, the plants are dusted with conidia of the fungus The infected plants are placed in a greenhouse at 22°. 12 days after infection, the fungal attack is evaluated Example B-8- Activity against Podosphaera leucotncha on apple shoots Apple cuttings with new shoots of ca. 15 cm length are sprayed with a spray mixture (0.06% active substance) After 24 hours, the treated plants are infected with a conidia suspension of the fungus and placed in a plant-growth chamber at 70% relative humidity and at 20°C. 12 days after infection, the fungal attack is evaluated

Claims: What we claim is 1. A compound of formula I wherein. A is a group CH 2 0 or CH 2 ON=C(R 1 ); Xi and X 2 independently of one another, are Cι-C 4 -alkyl; Y is OH, 0(d-C 4 -alkyl), NH 2 or NHCH 3 ; R, is d-C 4 -alkyl, cyclopropyl, cyano, trifluoromethyl or d-C 4 -alkoxy; R is aryl, hetaryl or heterocyclyl, whereby the above-mentioned groups may be substituted by one or more identical or different substituents, selected from the group comprising halogen, Cι-C 6 -alkyl, aryl which is optionally mono- to trisubstituted by identical or different substituents from d-d-alkyl, halogen, CrC 4 -alkoxy, CrC 4 -halogenalkyl or cyano; C r C 6 -alkoxy; halogen-CrC 6 -alkoxy; aryloxy which is optionally mono- to trisubstituted by identical or different substituents from Cι-C 4 -alkyl, halogen, Cι-C 4 -alkoxy, C C 4 - halogenalkyl or cyano, halogen-C C 6 -alkyl; Cι-C 6 -alkylthιo; halogen-C C 6 -alkylthιo; d-Cs-alkylsulfinyl; halogen-C C 6 -alkylsulfιnyl; d-C 6 -alkylsulfonyl; halogen-d-Ce-alkylsulfonyl; C 2 -C 6 -alkenyl; C 2 -C 6 -alkenyloxy; C -C 6 -alkynyl; C 3 -C 6 - alkynyloxy, halogen-C 2 -C 6 -alkenyl; halogen-C 2 -C 6 -alkenyloxy; halogen-C 2 -C 6 -alkynyl; halogen-C 3 -C 6 -alkynyloxy, d-C 6 -alkylcarbonyl; halogen-d-C 6 -alkylcarbonyl; CrC 6 -alkoxycarbonyl; halogen-C C 6 -alkoxycarbonyl; d-C 6 -alkylamιnocarbonyl, dι-(Cι-C 6 -alkyl)-amιnocarbonyl, whereby the alkyl groups may be identical or different; Cι- C 6 -alkylamιnothιocarbonyl; dι-(Cι-C 6 -alkyl)-amιnothιcarbonyl, whereby the alkyl groups may be identical or different; d-C 6 -alkylamιno; dι-(Cι-C 6 -alkyl)-amιno; N0 2 ; an unsubstituted Cι-C 4 -alkylendιoxy group or one which is mono- to tetrasubstituted by Cι-C 4 -alkyl and/or halogen, CN; SF 5 , OCN or C(=NOR 2 )-Z-R 3 ; R 2 and R 3 independently of one another, are hydrogen or d-C 6 -alkyl; Z is a direct bond, O, S, NH or N(d-C 6 -alkyl). 2. A compound according to claim 1 , wherein R is phenyl which is unsubstituted or mono- to tri-substituted by identical or different substituents from halogen, C C 6 -alkyl, C C 6 - halogenalkyl, C C 6 -alkoxy, Cι-C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 - aikynyl, C 3 -C 6 -alkynyloxy, d-C 6 -alkoxycarbonyl, cyano or OCN. 3. A compound according to claim 1 , wherein R is phenyl which is substituted by C(=NOR 2 )-Z-R , wherein R 2 and R 3 independently of one another signify hydrogen or Cι-C 4 -alkyl and Z signifies a direct bond. 4. A compound according to claim 1 , wherein R is pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl or pyrazolinyl, which are unsubstituted or mono- to trisubstituted by identical or different substituents from halogen, cyano, nitro, aminocarbonyl, d-C 4 -alkyl, Cι-C -halogenalkyl, d-C 4 -alkylcarbonyl, d-d-alkylsuifonyl, Cι-C 6 -alkylsulfoxyl, C 3 -C 6 -cycloalkyl, C C 4 -alkoxy, Cι-C 4 -halogenalkoxy, d-C 6 - alkoxycarbonyl, d-C 6 -alkylthio, d-Cβ-alkylamino, di-Cι-C 6 -alkylamino, d-C 6 - alkylaminocarbonyl, di-d-C 6 -alkylaminocarbonyl, C 2 -C 6 -alkenyl, C(=NOR 2 )-Z-R or by aryl that is optionally mono- to trisubstituted by identical or different substituents from Cι-C 4 - alkyl, halogen, Cι-C -alkoxy, C C 4 -halogenalkyl or cyano. 5. Process for the preparation of a compound of formula I characterised by the fact that A) a compound of formula II wherein A, R, Xi, X 2 and Y have the significances given for formula I, is reacted with an oxidation agent; or B) in order to produce a compound of formula I, wherein Y is OH, NH 2 or NHCH 3 and A, R, Xi and X 2 have the significances given for formula I, a compound of formula la wherein Y signifies 0(Cι-C 4 alkyl) and A, R, Xi and X 2 have the significances given for formula I, is reacted with an aqueous acid or base, or with NH 3 or with NH 2 CH 3 ; or C) in order to produce a compound of formula I, wherein Y is (Cι-C 4 -alkyl) or NHCH 3 , a compound of formula ill, wherein U is a leaving group and the remaining substituents have the above-mentioned significances, is reacted with an alcohol of the general formula IV or with an oxime of the general formula V, R-OH IV R(Rι)C=NOH V wherein R and Ri have the significances given for formula I; or D) a compound of formula VI, wherein the substituents have the significances given for formula I, is reacted with a methylation agent; or G) in order to produce a compound of formula I, wherein A is the group CH 2 ON=CRι and the remaining substituents have the significances given for formula I, a compound of formula IX, is reacted with a compound of formula R 1 -CO-R, wherein the substituents have the significances given for formula I. 6. A compound selected from the group wherein the substituents have the significances given in claim 1 and U is a leaving group. 7. Agrochemical composition containing as active ingredient an effective quantity of a compound of formula I according to claim 1 , together with an appropriate carrier. 8. Process for the protection of plants against harmful fungi, characterised in that a compound according to claim 1 is applied to the plants or to their locus.

Inventors: SZCZEPANSKI HENRY, ZELLER MARTIN, ZIEGLER HUGO, SZCZEPANSKI, HENRY, ZELLER, MARTIN, ZIEGLER, HUGO
Applicants: NOVARTIS AG, NOVARTIS ERFINDUNGEN, SZCZEPANSKI HENRY, ZELLER MARTIN, ZIEGLER HUGO, NOVARTIS-ERFINDUNGEN, SZCZEPANSKI, HENRY, ZELLER, MARTIN, ZIEGLER, HUGO
Application year: 1999
Main classification: C07C251
IPC codes: A01N37, C07C251