EP0984923A1 - O-benzyloximetherderivate und ihre anwendung als pestizide - Google Patents

O-benzyloximetherderivate und ihre anwendung als pestizide

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Publication number
EP0984923A1
EP0984923A1 EP98932081A EP98932081A EP0984923A1 EP 0984923 A1 EP0984923 A1 EP 0984923A1 EP 98932081 A EP98932081 A EP 98932081A EP 98932081 A EP98932081 A EP 98932081A EP 0984923 A1 EP0984923 A1 EP 0984923A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
formula
compound
halo
aryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP98932081A
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English (en)
French (fr)
Inventor
Stephan Trah
Henry Szczepanski
Ottmar Franz HÜTER
Roger Graham Hall
Saleem Farooq
Alfons Pascual
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Novartis Erfindungen Verwaltungs GmbH
Novartis AG
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Application filed by Novartis Erfindungen Verwaltungs GmbH, Novartis AG filed Critical Novartis Erfindungen Verwaltungs GmbH
Publication of EP0984923A1 publication Critical patent/EP0984923A1/de
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/32—Esters thereof
    • C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/3229—Esters of aromatic acids (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)

Definitions

  • the invention relates to compounds of formula
  • X is CH or N
  • Y is OR.
  • Z is O, or
  • Rt is hydrogen or C . -C 4 alkyl; Re is hydrogen or C ⁇ -C alkyl; R 2 is H, C C 4 alkyl, halo-C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, CrC 4 alkoxymethyl, C ⁇ -C 4 alkoxy, halo-C 1 -C alkoxy, d-C alkylthio, halo-C ⁇ -C 4 alkylthio or CN;
  • n is 0, 1 , 2, 3 or, if either a or b is 0, 4;
  • R 9 is methyl, fluoromethyl or difluoromethyl
  • R 7 is a radical R 10 ;
  • R 10 is H, C . -C 6 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl or C 3 -C 6 cycloalkyl, or d-C 6 alkyl, C 2 -C 8 - alkenyl, C 2 -C 8 alkynyl or C 3 -C 6 cycloalkyl each mono- or poly-substituted by substitu- ents from the group consisting of halogen; -Si(C C 4 alkyl) 3 , the alkyl groups being the same or different; d-Cealkoxycarbonyl or an aryl or heterocyclyl group that is unsubstituted or mono- or poly-substituted by substituents selected from the group consisting of halogen, d-C alkyl and halo-C ⁇ -C 4 alkyl; and
  • G is d-C 8 alkylene
  • R 6 is d-dalkyl, aryl or heteroaryl; or aryl or heteroaryl each of which - depending on the substitution possibilities on the ring structure - is mono- to penta-substituted by substituents selected independently of one another from the group consisting of (R 5 ) s ; s is, depending on the substitution possibilities on the ring, 0, 1 , 2, 3, 4 or 5, the substituents R 5 being independent of one another when s is greater than 1 ;
  • a T and R are as defined above for A and R 7 ; a is 0 or 1 ;
  • L is U-R. ⁇ , P(O) v RnR 12 , P(S) w RnR ⁇ 2 or N(aryl)R 13 , the aryl radical being either unsubstituted or mono- to penta-substituted by substituents selected independently of one another from the group consisting of R 5 ; v and w are 0 or 1 ;
  • p is from 0 to 4.
  • Rn and R 12 are each independently of the other C ⁇ -C 6 alkyl, halo-C ⁇ -C 6 alkyl, C 3 -C 6 cyclo- alkyl, halo-C 3 -C 6 cycloalkyl, C C 6 alkoxy, halo-C C 6 alkoxy, d-C ⁇ alkylthio, halo- C r C 6 alkylthio, aryl, heteroaryl, aryloxy, arylthio, heteroaryioxy or heteroarylthio; or aryl, heteroaryl, aryloxy, arylthio, heteroaryioxy or heteroarylthio each mono- to penta- substituted by R 5 , the substituents R 5 being independent of one another; b is 0 or 1 , but a and b are not simultaneously 0;
  • R- I3 is hydrogen, C . -C 6 alkyl, halo-d-C 6 alkyl, C 3 -C 6 cycloalkyl, halo-C 3 -C 6 cycloalkyl,
  • halo-d-C ⁇ alkoxydicarbonyl C ⁇ -C 6 alkylaminodicarbonyl, di(C ⁇ -C 6 alkyl)aminodicarbonyl, the alkyl groups being the same or different; C C 6 alkylaminodithiocarbonyl, d d-Cealky aminodithiocarbonyl, the alkyl groups being the same or different; aryl, arylsulfinyl, aryl-C 1 -C 6 alkylsulfinyl, arylsulfonyl, aryl- C C 6 alkyl-sulfonyl, aryloxy-d-C ⁇ alkyl, arylthio-C C 6 alkyl, aryl-C C 6 alkylsulfinyl- C C 6 alkyl, aryl-d-C ⁇ alkylsulfonyl-Ci-Cealkyl, arylcarbonyl,
  • R i4 and R i5 are each independently of the other d-C alkyl
  • R ⁇ e and R 7 are each independently of the other hydrogen, C ⁇ -C 4 alkyl or halogen and
  • the compounds may occur in the E and Z isomeric forms.
  • Atropisomers of the compounds may also occur.
  • the corresponding formulae are intended to include all those possible isomeric forms and also mixtures thereof, for example racemates or mixtures of E Z isomers, and also, where applicable, salts thereof, even if this is not specifically mentioned every time.
  • 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, alkylsulfinyl, 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. isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.
  • Alkenyl as a group perse 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 isopro- penyl.
  • 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 perse 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 -CH 2 CH 2 CH 2 CH 2 -, 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 )-.
  • Preference is given to - CH 2 CH 2 -, -CH(CH 3 )-, -CH(C 2 H 5 )-, and -CH 2 CH 2 CH 2 -.
  • Aryl is phenyi or naphthyl, especially phenyi.
  • 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 a nitrogen atom as hetero atom and optionally a further hetero atom, preferably nitrogen or sulfur, especially nitrogen.
  • Preferred heteroaryl moieties are pyrazinyl, 3'-pyridyl, 2'-pyridyl, 4'-pyridyl, 2'-pyrimidinyl, 4'-pyrimidinyl, 5'-pyrim- idinyl, 2'-thiazolyl, 2'-oxazolyl, 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 2 , CF 2 CHCIF, CF 2 CHBrF or CCIFCHCIF; propyl or isopropyl that is 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
  • a number of compounds of formula (I), and of the formulae (III) to (XXIV) given hereinafter, may, as is known to the person skilled in the art, be present in the form of tautomers, especially when R 7 is H.
  • any reference to these compounds should therefore 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) to (XXIV) 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-dalkanecarboxylic 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, hy- droxycarboxyiic 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, C ⁇ -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 mo ⁇ holine, 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 tri-ethanolamine. It may also be 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 mo ⁇ holine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine,
  • agrochemically advantageous salts also included, however, are salts which cannot be agrochemically used, 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 compounds of formula (I) in free form is to be under-stood as including also the salts of compounds of formula (I), and any reference to the salts is to be understood as including also the corresponding free compounds of formula (I), as appropriate and expedient.
  • tautomers of compounds of formulae (I) and (III) to (XXIV) and salts thereof In each case the free form is generally preferred.
  • R 2 is H, d-C 4 alkyl, halo-d-C 4 alkyl or C 3 -C 6 cycloalkyl, preferably d-dalkyl or halo-C ⁇ -C 4 alkyl, especially C 1 -C 2 alkyl, more especially methyl;
  • R 3 is H, d-dalkyl, d-C 4 alkoxy, OH, CN, NO 2 , halogen, halo-d-C 4 alkyl or halo- d-dalkoxy, preferably H, d-dalkyl, d-C 4 alkoxy or halogen, especially H, methyl, methoxy, chlorine or fluorine, more especially H; (6) a compound of formula (I) wherein
  • R 4 is H, d-dalkyl, d-C alkoxy, OH, CN, NO 2 , halogen, halo-C ⁇ -C alkyl or halo- Ci-dalkoxy, preferably H, C C alkyl, d-C 4 alkoxy or halogen, especially H, methyl, methoxy, chlorine or fluorine, more especially H;
  • R 8 is H or C ⁇ -C 2 alkyl, preferably C ⁇ -C 2 alkyl, especially methyl;
  • A is a direct bond, Ci-Cioalkylene or halo-d-C ⁇ 0 alkylene, preferably a direct bond or C dalkylene, especially a direct bond or methylene, and R 7 is a radical R 10 ;
  • Rn and R ⁇ 2 are each independently of the other C C 6 alkoxy, halo-C C 6 alkoxy, d-C 6 alkylthio, halo-C.-C 6 alkylthio, aryl, aryloxy or arylthio; or aryl, heteroaryl, aryloxy, arylthio, heteroaryioxy or heteroarylthio each mono- to tri- substituted by R 5 , the substituents R 5 being independent of one another;
  • R 6 being especially phenyi that is unsubstituted or mono- or di-substituted, especially mono- substituted, by halogen, d-C 4 alkyl, halo-C ⁇ -C alkyl or by halo-C ⁇ -C 4 alkoxy, especially mono-substituted by fluorine, chlorine, d-dalkyl, trifluoromethyl or by trifluoromethoxy.
  • 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, in each case in free form or in salt form, which process comprises, for example, either a1) reacting a compound of formula (I) and, where applicable, their E Z isomers, mixtures of E Z isomers and/or tautomers, in each case in free form or in salt form, which process comprises, for example, either a1) reacting a compound of formula (I) and, where applicable, their E Z isomers, mixtures of E Z isomers and/or tautomers, in each case in free form or in salt form, which process comprises, for example, either a1) reacting a compound of formula (I) and, where applicable, their E Z isomers, mixtures of E Z isomers and/or tautomers, in each case in free form or in salt form, which process comprises, for example, either a1) reacting a
  • 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, for example,
  • R ⁇ ONH, (VII) which is known or can be prepared according to methods known perse and wherein A and R 7 are as defined for formula (I) and, in each case, if desired, converting a compound of formula (III) obtainable according to the process or by a different method, or an E/Z isomer or tautomer thereof, in each case in free form or in salt form, into a different compound of formula (III) or an E/Z isomer or tautomer thereof, in each case in free form or in salt form, separating a mixture of E/Z isomers obtainable according to the process and isolating the desired isomer and/or converting a free compound of formula (III) obtainable according to the process or by a different method, or an E/Z isomer or tautomer thereof, into a salt, or converting a salt of a compound of formula (III), or of an E/Z isomer or tautomer thereof, obtainable according to the process or by a different method into the free
  • the invention relates also to a process for the preparation of a compound of formula
  • Hal is a halogen atom, preferably fluorine, with a compound of formula
  • T in the case where, in a compound of formula (Vlll), T is -C ⁇ C-, reacting a compound of formula wherein R 2 , R 5 , L, D, G, n and b are as defined above for formula (I), with a compound of the formula Hal-Re, which is known or can be prepared in accordance with methods known perse, and wherein Hal is halogen, preferably bromine or iodine, especially iodine, and R ⁇ 8 is as defined for formula (I); or
  • H-N(aryl)R 13 (XXI), which are known or can be prepared in accordance with methods known per se, and wherein v, w, Rn, R ⁇ 2 , R 1 3 and aryl are as defined for fomnula (I), preferably in the presence of a base and a catalyst, especially a transition metal catalyst, more especially a palladium catalyst or a ferrocene derivative;
  • R 2 , R 5 , R 6 , L, D, G, T, a, b and n are as defined in formula (I), in each case in free form or in salt form, which process comprises reacting a compound of the formula (Vlll) with a nitrite;
  • R 5 , R 6 , L, D, G, T, a, b and n are as defined in formula (I), with a nitroalkane;
  • 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 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, and, if required, in a closed vessel, under pressure, in an inert gas atmosphere and/or under anhydrous conditions.
  • Especially advantageous reaction conditions may be found in the Examples.
  • the reactants may be reacted with one another 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 products are isolated in accordance with customary methods, for example by filtration, crystallisation, distillation or chromatography, or any suitable combination of those methods.
  • Suitable leaving groups Xi in the compounds of formula (II) are, for example, hydroxy, d-C 8 alkoxy, haio-d-C 8 alkoxy, C ⁇ -C 8 alkanoyloxy, mercapto, d-C 8 alkylthio, halo-C ⁇ -C 8 alkylthio, d-C 8 alkanesulfonyloxy, halo-C ⁇ -C 8 alkanesulfonyloxy, benzene- sulfonyloxy, toluenesulfonyloxy and halogen, preferably toluenesulfonyloxy, trifluoro- methanesulfonyloxy 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 al- kylsilylamides, alkylamines, alkylenediamines, unsubstituted or N-alkylated, saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines.
  • solvents or diluents include: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chloro- benzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene and tetrachloroethene; 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, dimethoxydiethy
  • bases used in excess such as triethylamine, pyridine, N-methylmo ⁇ holine 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.
  • reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours.
  • a compound of formula (II) is reacted with a compound of formula (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.
  • Variant b) examples 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.
  • solvents or diluents 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, trichloro- ethene and tetrachloroethene; 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 ether, tetra
  • the reaction is carried out advantageously in a temperature range from approximately 0°C to approximately +120°C, preferably from approximately 80°C to approximately +120°C.
  • 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 peracids, such as perbenzoic acid or peracetic acid, or mixtures of organic acids and hydrogen peroxide, for example acetic acid/hydrogen peroxide.
  • solvents or diluents include: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chloro- benzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene and tetrachloroethene; 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, dimethoxydiethy
  • reaction is carried out in the presence of an organic acid or peracid
  • acids used in excess for example strong organic carboxylic acids, such as unsubstituted or substituted, for example halo-substituted, d-C alkanecarboxylic 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, preferably from approximately 0°C to approximately +40°C.
  • 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 variant a1/a2).
  • solvents or diluents examples 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.
  • reaction duration of from approximately 0.1 to approximately 24 hours, especially from approximately 0.5 to approximately 2 hours.
  • Example P3 e Especially preferred conditions may be found in Example P3 e).
  • Variant f Suitable bases for facilitating the reaction are, for example, those mentioned in variant a1/a2).
  • solvents or diluents examples 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.
  • a compound of formula (VI) is reacted with a co m- pound of formula (VII) 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.
  • Especially preferred conditions may be found in Example P1-1c) and also in the analogous reaction described in Example P3 e).
  • Especially preferred conditions for process variants g), h), i), k), I) and m) may be found in the Examples.
  • the conditions for the process according to variant g) may be found in Examples P9-1 and P9-2; according to variant h) in Example P6-1 ; according to variant i) in Example P1-1a); according to variant k) in Examples P3b) and P5b); according to variant I) in Example P7-1; and according to variant m) in Examples P10-1 and P12-1 or applied analogously to those processes.
  • Some of the compounds of formulae (I) and (III) to (XXIV) 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.
  • enantiomers such as racemates
  • optical antipodes can be separated into the optical antipodes by known methods, for example by recrystaliisation from an optically active solvent, by chromatography on chiral adsorbents, for example high-pressure liquid chromatography (HPLC) on acetyl cellulose, with the aid of suitable microorganisms, by cleav- age with specific immobilised enzymes, and via the formation of inclusion compounds, for example using chiral crown ethers, in which case only one enantiomer is complexed.
  • HPLC high-pressure liquid chromatography
  • Some of the compounds (I) and (III) to (XXIV) 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 especially to the preparation processes described in Examples P1 to P12.
  • the invention relates also to starting materials and intermediates used according to the i n- vention in the preparation of compounds of formula (I), especially the compounds of form u- lae (III), (IV), (VI), (Vlll), (IX), (XII), (XIII), (XV), (XVII), (XVIII), (XXII), (XXIII) and (XXIV), which are novel, to their use and to processes for the preparation thereof.
  • the compounds of formulae (III) and (VI) can be prepared analogously to Examples P1 c) and P1 b), 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-736 252. Accordingly, 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 the Fungi imperfecti, for example,
  • Botrytis spp. Pyricularia spp., Helminthosporium spp., Fusarium spp., Septoria spp., Cerco- spora spp. and Alternaria spp.; of the class of the Basidiomycetes, for example,
  • Rhizoctonia spp. Hemileia spp. and Puccinia spp.; of the class of the Ascomycetes, for example,
  • Venturia spp. Erysiphe spp., Podosphaera spp., Monilinia spp. and Uncinula spp.; and of the class of the Oomycetes, for example,
  • 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 emulsifiabie 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 emulsifiabie 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 used are, e.g., solid carriers, solvents, stabilisers, "slow release” adjuvants, colorants and optionally surface-active substances (surfactants).
  • Suitable carriers and adjuvants include any 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 include, for example, the same substances as those described in EP-A-736252. Accordingly, the said adjuvants mentioned in EP-A-736252 are included by reference in the subject matter of the present invention.
  • 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.
  • Emulsifiable concentrates active ingredient: 1 to 90 %, preferably 5 to 20 % surfactant: 1 to 30 %, preferably 10 to 20 % solvent: 5 to 98 %, preferably 70 to 85 %
  • Dusts active ingredient: 0.1 to 10 %, preferably 0.1 to 1 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %
  • Suspension concentrates active ingredient: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surfactant: 1 to 40 %, preferably 2 to 30 %
  • Wettable powders active ingredient: 0.5 to 90 %, preferably 1 to 80 % surfactant: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 99 %, preferably 15 to 98 %
  • Granules active ingredient: 0.5 to 30 %, preferably 3 to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 %
  • compositions according to the invention can be substantially broadened and adapted to prevailing circumstances by the addition of other insecticidal, acaricidal and/or f ungicidal active ingredients.
  • suitable additional active ingredients include representatives of the following classes of compounds: organophosphorus compounds, nitrophenols and derivatives, formamidines, ureas, carbamates, pyrethroids, chlorinated hydrocarbons 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, or 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 processes 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.
  • 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 inco ⁇ orated 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 P1-1 2-[[[(1 -Methyl-2-(4-(1 - ⁇ 4-chlorophenyl ⁇ -ethoxy)-phenyl)-[ethoxyimino]- ethylidene)amino]oxy]methyl]- ⁇ -(methoxymethylene)-phenylacetic acid methyl ester a) 1 -[4-(1 - ⁇ 4-Chlorophenyl ⁇ -ethoxy)-phenyl]-propan-1 -one
  • Dry HCI gas is introduced into 200 ml of diethyl ether over a period of 0.5 minutes and 43.2 g of 1-[4-(1- ⁇ 4-chlorophenyl ⁇ -ethoxy)-phenyl]-propan-1-one are then added. 21.0 g of isopentyl nitrite are then added dropwise and the reaction mixture is then stirred for 3 hours at room temperature. The reaction mixture is concentrated by evaporation in vacuo and the crude product is purified by chromatography on silica gel using ethyl acetate/hexane (1:3), yielding the title compound having a melting point of 88-90°C.
  • Example P1-2 2-[[[(1 -Methyl-2-(4-(1 - ⁇ 4-chlorophenyl ⁇ -ethoxy)-phenyl)-[ethoxyimino]ethyl- idene)amino]oxy]methyl]- ⁇ -(methoxyimino)-phenylacetic acid methyl ester
  • 1 -[4-(1 - ⁇ 4-chlorophenyl ⁇ - ethoxy)-phenyl]-1 ,2-propanedione-[ethyloxime]-2-oxime and 2-(bromomethyl)- ⁇ -(methoxy- imino)-phenylacetic acid methyl ester yield the title compound having a melting point of 111 -113°C (compound 2.4-2).
  • Example P1-3 2-[[[(1 -Methyl-2-(4-(1 - ⁇ 4-chlorophenyl ⁇ -ethoxy)-phenyl)-[ethoxyimino]ethyl- idene)amino]oxy]methyl]- ⁇ -(methoxyimino)-phenylacetic acid methylamide
  • Example P2 It is also possible to prepare the other compounds listed in Tables 1.1 to 3.26 in a manner analogous to that described in Example P1; c.propyl denotes cyclopropyl.
  • Table 1 -2 Compounds of general formula (1.1) wherein (R 5 ) s is 3-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 5 ) s is 2-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 5 )s is 4-CI 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 5 ) s is 3-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 5 )s is 2-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 5 ) s is 4-Br 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 5 )s is 3-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 5 ) s is 2-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 5 ) s is 4-F 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 5 ) s is 3-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 5 ) s is 2-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 5 ) s is 2,4-CI 2 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 5 ) s is 3,4-CI 2 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 5 ) s 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 5 ) s is 4-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 5 ) s is 4-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 5 ) s is 4-n-C 3 H 7 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 1-19 Compounds of general formula (1.1) wherein (R 5 ) s is 4-iso-C 3 H 7 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 5 ) s is 4-n-C H 9 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 5 ) s is 4-isobutyl 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 5 )s is 4-sec-butyl 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 5 )s is 4-tert-butyl 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 5 ) s is 4-CN 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 5 ) s is 4-O-CH 3 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 5 ) s is 2,4-F 2 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-2 Compounds of general formula (I.2) wherein (R 5 ) s is 3-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-3 Compounds of general formula (I.2) wherein (R 5 ) s is 2-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-4 Compounds of general formula (I.2) wherein (R 5 ) s is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-5 Compounds of general formula (I.2) wherein (R 5 ) s is 3-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-6 Compounds of general formula (1.2) wherein (R 5 ) s is 2-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-7 Compounds of general formula (1.2) wherein (R 5 ) s is 4-Br and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-8 Compounds of general formula (1.2) wherein (R 5 ) s is 3-Br and the substituent A-R corresponds in each case to a line of Table A.
  • Table 2-9 Compounds of general formula (1.2) wherein (R 5 ) s is 2-Br and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-10 Compounds of general formula (I.2) wherein (R 5 ) s is 4-F and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-11 Compounds of general formula (I.2) wherein (R 5 ) s is 3-F and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-12 Compounds of general formula (I.2) wherein (R 5 ) s is 2-F and the substituent A-R corresponds in each case to a line of Table A.
  • Table 2-13 Compounds of general formula (I.2) wherein (R 5 ) s is 2,4-CI 2 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-14 Compounds of general formula (I.2) wherein (R 5 ) s is 3,4-CI 2 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-15 Compounds of general formula (I.2) wherein (R 5 ) s is 4-O-CF 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-16 Compounds of general formula (I.2) wherein (R 5 ) s is 4-CH 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-17 Compounds of general formula (I.2) wherein (R 5 ) s is 4-C 2 H 5 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-18 Compounds of general formula (I.2) wherein (R 5 ) s is 4-n-C 3 H 7 and the substituent A-R corresponds in each case to a line of Table A.
  • Table 2-19 Compounds of general formula (I.2) wherein (R 5 ) s is 4-iso-C 3 H 7 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-20 Compounds of general formula (1.2) wherein (R 5 ) s is 4-n-C H 9 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-21 Compounds of general formula (I.2) wherein (R 5 )s is 4-isobutyl and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-22 Compounds of general formula (I.2) wherein (R 5 ) s is 4-sec-butyl and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-23 Compounds of general formula (I.2) wherein (R 5 ) s is 4-tert-butyl 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 5 ) s is 4-CN and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-25 Compounds of general formula (I.2) wherein (R 5 ) s is 4-O-CH 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 2-26 Compounds of general formula (I.2) wherein (R 5 ) s is 2,4-F 2 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 5 ) s is 3-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 5 ) s is 2-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 5 ) s is 4-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 3-5 Compounds of general formula (1.3) wherein (R 5 )s is 3-CI and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 3-6 Compounds of general formula (1.3) wherein (R 5 )s is 2-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 5 ) s is 4-Br 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 5 ) s is 3-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 5 ) s is 2-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 5 ) s is 4-F 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 5 ) s is 3-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 5 ) s is 2-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 5 ) s is 2,4-CI 2 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 5 ) s is 3,4-CI 2 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 5 ) s 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 (I.3) wherein (R 5 )s is 4-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 (I.3) wherein (R 5 ) s is 4-C 2 H 5 and the substituent A-R corresponds in each case to a line of Table A.
  • Table 3-18 Compounds of general formula (I.3) wherein (R 5 ) s is 4-n-C 3 H 7 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 s ) s is 4-iso-C 3 H 7 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 5 ) s is 4-n-C 4 H 9 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 5 ) s is 4-isobutyl and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 3-22 Compounds of general formula (I.3) wherein (R 5 ) s is 4-sec-butyl 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 5 ) s is 4-tert-butyl and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 3-24 Compounds of general formula (I.3) wherein (R 5 )s is 4-CN and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 3-25 Compounds of general formula (I.3) wherein (R 5 ) s is 4-O-CH 3 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • Table 3-26 Compounds of general formula (I.3) wherein (R 5 ) s is 2,4-F 2 and the substituent A-R 7 corresponds in each case to a line of Table A.
  • 35 g of a compound obtainable according to process P3b) are placed in 200 ml of methanol and 18 ml of isopentyl nitrite. At 0°C, 30 ml of a 30 % solution of sodium methanolate in methanol are added dropwise and the mixture is stirred for 2 hours at room temperature. The solvent is evaporated off, and 200 ml of ethyl acetate and 200 ml of water are added; the aqueous phase is separated off and the organic phase is then washed several times with water. Evaporating off the solvent and recrystallisation of the residue from di- chloromethane/hexane yield the title product having a melting point of 131-133°C.
  • Example P4 It is also possible to prepare the other compounds listed in Table 4 in a manner analogous to that described in Example P3.
  • the figures given in the column "Phys. data” denote melting points in °C.
  • Table 4-1 Compounds of general formula
  • Example P5-1 2-ITf (1 -Methvl-2-(4-f(dimethyl-(4-f luorophenvh-silvllmethoxvlphenvl ⁇ - [ethoxyimino]ethylidene)amino]oxy]methyl]- ⁇ -(methoxyimino)-phenylacetic acid methyl ester and 2-[[[(1-methyl-2-(4-[ ⁇ dimethyl-(4-fluorophenyl)-silyl ⁇ methoxy]phenyl)-[ethoxyimino]ethyl- idene)amino]oxy]methyl]- ⁇ -(methoxyimino)-phenylacetic acid methylamide a) Chloromethyl-dimethyl-(4-fluorophenyl)-silane
  • reaction mixture is poured onto 200 ml of ice, and 300 ml of diethyl ether are added; the mixture is washed with water and saturated sodium chloride solution and dried over sodium sulfate; the solvent is evaporated off in vacuo. Distillation of the residue at 97- 105°C (21 mbar) yields the title product.
  • Example P5-2 It is also possible to prepare the other compounds listed in Table 5 in a manner analogous to that described in Example P5-1.
  • the figures given in the column "Phys. data” denote melting points in °C.
  • Example P6-2 It is also possible to prepare the other compounds listed in Table 6 in a manner analogous to that described in Example P6-1.
  • the figures given in the column "Phys. data” denote melting points in °C.
  • Example P7-2 It is also possible to prepare the other compounds listed in Table 7 in a manner analogous to that described in Example P7-1.
  • the figures given in the column "Phys. data” denote melting points in °C.
  • Example P8-1 2-[[[(1-Meth yl-2-(4- ⁇ 3-(3-trifl ⁇ loromethylph
  • Example P8-2 It is also possible to prepare the other compounds listed in Table 8 in a manner analogous to that described in Example P8-1.
  • Example P9-3 It is also possible to prepare the other compounds listed in Tables 9-1 and 9-2 in a manner analogous to that described in Examples P9-1 and P9-2.
  • the figures given in the column "Phys. data” denote melting points in °C.
  • reaction mixture is cooled, filtered over silica gel and diluted with ethyl acetate; the organic phase is extracted by shaking with water and saturated NaCl solution. After drying over MgSO 4 and evaporating off the solvent, a sticky residue is obtained, which is purified by means of column chromatography (ethyl acetate/hexane 1 :5), yielding the title compound having a melting point of 109-110°C.
  • Isopentyl nitrite (3.0 g) is slowly added dropwise at 20°C to 7.2 g of 6-chloro-3-(4'-(2-oxo- propyl)phenyl)benzisoxazole in methanol (37 ml). After the addition of 30 % sodium methanolate (5.7 g), stirring is carried out overnight at room temperature. The reaction mixture is concentrated by evaporation at 50°C; the residue is dissolved in water and rendered acidic with 10 % hydrochloric acid at 10°C. Ethyl acetate is added, the water phase separated and the organic phase washed with water. Drying over MgSO 4 and concentration by evaporation yield a solid, which is stirred together with hexane, filtered off with suction and dried in air to yield the title compound having a melting point of 224-226°C.
  • Ethyl iodide (5.45 g) is added to 6-chloro-3-(4'-(1-hydroxyimino-2-oxo)propyl)benzisoxazole (7.01 g), acetonitrile (44 ml) and potassium carbonate (4.3 g).
  • the batch is heated for 3 hours under reflux, cooled to room temperature and filtered, the filter being rinsed with acetonitrile.
  • the filtrate is concentrated by evaporation using a rotary evaporator; the residue is taken up in ethyl acetate and washed with water and brine. Drying of the organic phase over Na 2 SO and concentration by evaporation yield the title compound having a melting point of 106-107°C.
  • compounds 9-3.1 to 9-3.3 can be prepared analogously to the process variants a1), a2) and b).
  • Example P9-5 It is also possible to prepare the intermediates required for the other compounds listed in Table 9-3 in a manner analogous to that described in Example P9-4.
  • the figures given in the column "Phys. data” denote melting points in °C.
  • Example P11 It is also possible to prepare the other compounds listed in Tables 10 and 11 in a manner analogous to that described in Example P10-1.
  • Table B Compounds of general formula
  • Table 10-1 Compounds of general formula (1.10) wherein AR 7 is CH 3 and the combination of substituents X, Y, (W) w , Rn and R. 2 for each compound corresponds to a line of Table B.
  • Table 10-2 Compounds of formula (1.10) wherein AR 7 is CH 2 CH 3 and the combination of substituents X, Y, (W) w , Rn and R ⁇ 2 for each compound corresponds to a line of Table B.
  • Table 10-4 Compounds of formula (1.10) wherein AR 7 is CH 2 C ⁇ CH and the combination of substituents X, Y, (W) w , Rn and R-
  • Table 10-5 Compounds of formula (1.10) wherein AR 7 is CH 2 CH 2 CH 3 and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 10-6 Compounds of formula (1.10) wherein AR 7 is CH(CH 3 ) 2 and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 10-7 Compounds of formula (1.10) wherein AR 7 is CH 2 CH 2 CH 2 CH 3 and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 10-8 Compounds of formula (1.10) wherein AR 7 is CH(CH 3 )(CH 2 CH 3 ) and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 10-9 Compounds of formula (1.10) wherein AR 7 is C(CH 3 ) 3 and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 10-10 Compounds of formula (1.10) wherein AR 7 is CH 2 CF 3 and the combination of substituents X, Y, (W) w , R and R 12 for each compound corresponds to a line of Table B.
  • Table 10-13 Compounds of formula (1.10) wherein AR 7 is CH 2 Si(CH 3 ) 3 and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 10-14 Compounds of formula (1.10) wherein AR 7 is CH 2 -c.propyl-2,2-CI 2 and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 10-15 Compounds of formula (1.10) wherein AR 7 is CH 2 CN and the combination of substituents X, Y, (W) WI Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 10-16 Compounds of formula (1.10) wherein AR 7 is CH 2 COOCH 3 and the combination of substituents X, Y, (W) w , Rn and R-
  • Table 10-17 Compounds of formula (1.10) wherein AR 7 is CH 2 COO-iso-C 3 H 7 and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 10-21 Compounds of formula (1.10) wherein AR is CH 2 C 6 H 5 and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 10-22 Compounds of formula (1.10) wherein AR 7 is CH 2 C 6 H 4 -2-F and the combination of substituents X, Y and (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 10-23 Compounds of formula (1.10) wherein AR 7 is CH 2 C 6 H 4 -3-CI and the combination of substituents X, Y, (W) w , Rn and R 2 for each compound corresponds to a line of Table B.
  • Table 10-24 Compounds of formula (1.10) wherein AR 7 is CH 2 C 6 H 4 -4-Br and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 10-25 Compounds of formula (1.10) wherein AR 7 is CH 2 C 6 H 4 -3-CF 3 and the combination of substituents X, Y, (W) w , Rn and R ⁇ 2 for each compound corresponds to a line of Table B.
  • Table 10-26 Compounds of formula (1.10) wherein AR is CH 2 C 6 H 4 -4-CF 3 and the combination of substituents X, Y, (W) w , Rn and R ⁇ 2 for each compound corresponds to a line of Table B.
  • Table 11-1 Compounds of formula
  • AR 7 is CH 3 and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 11 -2 Compounds of formula (1.11) wherein AR 7 is CH 2 CH 3 and the combination of substituents X, Y, (W) w , Rn and R-
  • Table 11-5 Compounds of formula (1.11 ) wherein AR is CH 2 CH 2 CH 3 and the combination of substituents X, Y, (W) w , Rn and R ⁇ 2 for each compound corresponds to a line of Table B.
  • Table 11 -6 Compounds of formula (1.11) wherein AR 7 is CH(CH 3 ) 2 and the combination of substituents X, Y, (W) w , Rn and R- ⁇ 2 for each compound corresponds to a line of Table B.
  • Table 11 -7 Compounds of formula (1.11) wherein AR 7 is CH 2 CH 2 CH 2 CH 3 and the combination of substituents X, Y, (W) w , Rn and R-
  • Table 11 -8 Compounds of formula (1.11) wherein AR 7 is CH(CH 3 )(CH 2 CH 3 ) and the combination of substituents X, Y, (W) w , Rn and R-
  • Table 11-9 Compounds of formula (1.11) wherein AR 7 is C(CH 3 ) 3 and the combination of substituents X, Y, (W) w , Rn and R-
  • Table 11-10 Compounds of formula (1.11) wherein AR 7 is CH 2 CF 3 and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 11-13 Compounds of formula (1.11 ) wherein AR 7 is CH 2 Si(CH 3 ) 3 and the combination of substituents X, Y, (W) w , Rn and R ⁇ 2 for each compound corresponds to a line of Table B.
  • Table 11-14 Compounds of formula (1.11) wherein AR 7 is CH 2 -c.propyl-2,2-CI 2 and the combination of substituents X, Y, (W) w , Rn and R-
  • Table 11-15 Compounds of formula (1.11) wherein AR 7 is CH 2 CN and the combination of substituents X, Y, (W) w , Rn and R-
  • Table 11-16 Compounds of formula (1.11) wherein AR 7 is CH 2 COOCH 3 and the combination of substituents X, Y, (W) w , Rn and R- ⁇ 2 for each compound corresponds to a line of Table B.
  • Table 11-17 Compounds of formula (1.11) wherein AR 7 is CH 2 COO-iso-C 3 H 7 and the combination of substituents X, Y, (W) w , Rn and R ⁇ 2 for each compound corresponds to a line of Table B.
  • Table 11-21 Compounds of formula (1.11) wherein AR 7 is CH 2 C 6 H 5 and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 11-22 Compounds of formula (1.11 ) wherein AR 7 is CH 2 C 6 H 4 -2-F and the combination of substituents X, Y and (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 11 -23 Compounds of formula (1.11) wherein AR 7 is CH 2 C 6 H 4 -4-Br and the combination of substituents X, Y, (W) w , Rn and R 12 for each compound corresponds to a line of Table B.
  • Table 11 -24 Compounds of formula (1.11) wherein AR 7 is CH 2 C 6 H 4 -3-CF 3 and the combination of substituents X, Y, (W) w , Rn and R ⁇ 2 for each compound corresponds to a line of Table B.
  • Table 11-25 Compounds of formula (1.11) wherein AR 7 is CH 2 C 6 H 4 -4-CF 3 and the combination of substituents X, Y, (W) w , R and R 12 for each compound corresponds to a line of Table B.
  • Table 12-2 Compounds of formula (1.12) wherein AR 7 is CH 2 CH 3 and the combination of substituents X, Y, (R 5 ) s , (RssJn and R-
  • Table 12-4 Compounds of formula (1.12) wherein AR 7 is CH 2 C ⁇ CH and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R 13 for each compound corresponds to a line of Table 2.
  • Table 12-5 Compounds of formula (1.12) wherein AR 7 is CH 2 CH 2 CH 3 and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R 13 for each compound corresponds to a line of Table 2.
  • Table 12-6 Compounds of formula (1.12) wherein AR 7 is CH(CH 3 ) 2 and the combination of substituents X, Y, (Rs) s . (Rss)n and R 13 for each compound corresponds to a line of Table C.
  • Table 12-7 Compounds of formula (1.12) wherein AR 7 is CH 2 CH 2 CH 2 CH 3 and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R 13 for each compound corresponds to a line of Table C.
  • Table 12-8 Compounds of formula (1.12) wherein AR 7 is CH(CH 3 )(CH 2 CH 3 ) and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R 13 for each compound corresponds to a line of Table C.
  • Table 12-9 Compounds of formula (1.12) wherein AR 7 is C(CH 3 ) 3 and the combination of substituents X, Y, (R 5 ) s , (Rss) n and R 13 for each compound corresponds to a line of Table C.
  • Table 12-10 Compounds of formula (1.12) wherein AR 7 is CH 2 CF 3 and the combination of substituents X, Y, (Rs) s , (RssJn and R 13 for each compound corresponds to a line of Table C.
  • Table 12-13 Compounds of formula (1.12) wherein AR 7 is CH 2 Si(CH 3 ) 3 and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R 13 for each compound corresponds to a line of Table C.
  • Table 12-14 Compounds of formula (1.12) wherein AR 7 is CH 2 -c.propyl-2,2-CI 2 and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R 13 for each compound corresponds to a line of Table C.
  • Table 12-15 Compounds of formula (1.12) wherein AR 7 is CH 2 CN and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R 13 for each compound corresponds to a line of Table C.
  • Table 12-16 Compounds of formula (1.12) wherein AR 7 is CH 2 COOCH 3 and the combination of substituents X, Y, (R 5 ) s , (Rssin and R-
  • Table 12-17 Compounds of formula (1.12) wherein AR 7 is CH 2 COO-iso-C 3 H 7 and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R-
  • Table 12-21 Compounds of formula (1.12) wherein AR is CH 2 C 6 H 5 and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R 13 for each compound corresponds to a line of Table C.
  • Table 12-22 Compounds of formula (1.12) wherein AR is CH 2 C 6 H 4 -2-F and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R 13 for each compound corresponds to a line of Table C.
  • Table 12-23 Compounds of formula (1.12) wherein AR 7 is CH 2 C 6 H 4 -3-CI and the combination of substituents X, Y, (Rs) s , (Rss) n and R 13 for each compound corresponds to a line of Table C.
  • Table 12-24 Compounds of formula (1.12) wherein AR 7 is CH 2 C 6 H 4 -4-Br and the combination of substituents X, Y, (R 5 ) s , (Rss) n and R 13 for each compound corresponds to a line of Table C.
  • Table 12-25 Compounds of formula (1.12) wherein AR 7 is CH 2 C 6 H 4 -3-CF 3 and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R 13 for each compound corresponds to a line of Table C.
  • Table 12-26 Compounds of formula (1.12) wherein AR 7 is CH 2 C 6 H 4 -4-CF 3 and the combination of substituents X, Y, (R 5 ) s , (R 5 s)n and R-
  • Table 13-1 Compounds of formula (1.13) wherein AR 7 is CH 3 and the combination of substituents X, Y, (Rs) s . (Rss)n and R13 for each compound corresponds to a line of Table C.
  • Table 13-2 Compounds of formula (1.13) wherein AR 7 is CH 2 CH 3 and the combination of substituents X, Y, (Rs) s , (Rss) n and R 13 for each compound corresponds to a line of Table C.
  • Table 13-4 Compounds of formula (1.13) wherein AR 7 is CH 2 C ⁇ CH and the combination of substituents X, Y, (R 5 ) s , (Rss) n and R 13 for each compound corresponds to a line of Table C.
  • Table 13-5 Compounds of formula (1.13) wherein AR 7 is CH 2 CH 2 CH 3 and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R-
  • Table 13-6 Compounds of formula (1.13) wherein AR 7 is CH(CH ) 2 and the combination of substituents X, Y, (Rs) s . (Rss)n and R1 3 for each compound corresponds to a line of Table C.
  • Table 13-7 Compounds of formula (1.13) wherein AR 7 is CH 2 CH 2 CH 2 CH 3 and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R 13 for each compound corresponds to a line of Table C.
  • Table 13-8 Compounds of formula (1.13) wherein AR 7 is CH(CH 3 )(CH 2 CH 3 ) and the combination of substituents X, Y, (R 5 ) s , (Rss)n and R 13 for each compound corresponds to a line of Table C.
  • Table 13-9 Compounds of formula (1.13) wherein AR 7 is C(CH 3 ) 3 and the combination of substituents X, Y, (Rs) s , (RssJn and R 13 for each compound corresponds to a line of Table C.
  • Table 14 Compounds of formula (1.13) wherein AR 7 is C(CH 3 ) 3 and the combination of substituents X, Y, (Rs) s , (RssJn and R 13 for each compound corresponds to a line of Table C.
  • Table 14 Compounds of formula (1.13) wherein AR 7 is C(CH 3 ) 3 and the combination of substituents X, Y, (Rs) s , (RssJn and R 13 for each compound corresponds to a line of Table C.
  • Table 14 Compounds of formula (1.13) wherein AR 7 is C(CH 3 ) 3 and the combination of substituents X, Y, (Rs) s , (RssJn and R 13
  • Formulations such as emulsifiable concentrates, solutions granules, dusts, wettable powders, emulsifiable concentrates, extruder granules, coated granules and suspension concentrates are of the same kind as mentioned in EP-A-736 252, examples F1 to F10. Accordingly, the said formulations mentioned in EP-A-736252 are included by reference in the subject matter of the present invention.
  • 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 containing 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 blotches 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 at a concentration of 60 ppm (based on the volume of soil) is used to water 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 blotches 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 DeToni) on vines 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 mixtures 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 of Tables 1 to 15 exhibit an infestation of 20 % or less.
  • the compounds 1-4.2, 3-4.2, 4-1.2, 6.3, 8.10 and 9-2.2 complete curative action is still obtained even at a concentration of 20 ppm of the test compound.
  • Example B3 Action against Puccinia graminis on wheat a) Residual-protective action
  • wheat plants are sprayed to drip point with an aqueous spray mixture (0.02 % active ingredient), and infected 24 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.
  • 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.
  • the compounds of Tables 1 to 15 bring about a distinct reduction in the fungus infestation, in some cases to from 10 to 0 %.
  • the compounds 3-4.2, 4.1-1 , 5.4, 8.10, 12-1.3, 10-1.16 and 12-1.4 the disease is suppressed completely (0-5 % infestation).
  • Example B4 Action against Pyricularia oryzae on rice plants a) Residual-protective action
  • rice plants are sprayed to drip point with an aqueous spray mixture (0.02 % active ingredient), and are infected 48 hours later with a conidia sus- pension of the fungus. Evaluation of fungus infestation is made 5 days after infection, du r- ing which period 95 to 100 % relative humidity and a temperature of 22°C are maintained.
  • 2-week-old rice plants are watered 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 plant above the soil.
  • the pots are then filled with water so that the lowermost parts of the stems of the rice plants stand in water. After 96 hours, the plants are infected with a conidia suspension of the fungus and kept for 5 days at 95 to 100 % relative humidity and a temperature of 24°C.
  • the compounds of Tables 1 to 15 largely prevent the disease from breaking out on the i n- fected plants.
  • Example B5 Action against Erysiphe graminis on barlev 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.
  • 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.
  • the compounds of Tables 1 to 15 in general are able to suppress infestation with the disease to less than 20 % and, in some cases, to suppress it completely.
  • Example B6 Action against Botrytis cinerea on apple fruits. Residual -protective action Artificially damaged apples are treated by applying drops of a spray mixture (0.02 % active ingredient) onto the damage sites. The treated fruits are then inoculated with a spore su s- pension of the fungus and incubated for one week at high humidity and about 20°C. The fungicidal action of the test compound is derived from the number of rotted damage sites. Compounds of Tables 1 to 15 are able to prevent the rot from spreading, in some cases completely.
  • Example B7 Action against Aphis craccivora
  • 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.
  • the compounds of Tables 1 to 15 exhibit good activity in this test. In particular, compounds 1-4.2, 2-4.2, 4-1.2, 4-1.8, 5.5, 9-2.2, 12-1.3, 10-1.16 and 12-1.4 are more than 80 % effective in this test.
  • Example B9 Action against Heliothis virescens
  • Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of the test compound. After the spray-coating has dried, the plants are populated with 10 Spodoptera littoralis caterpillars 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. The compounds of Tables 1 to 15 exhibit good activity in this test.
  • Example B11 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 the 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.
  • the compounds of Tables 1 to 15 generally exhibit good activity in this test. In particular, compounds 1-4.2, 2-4.2, 3-4.2, 4-1.1 , 5.5, 6.3, 8.10, 9-2.2, 12-1.3, 10-1.16 and 12-1.4 are more than 80 % effective in this test.

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