N-phenylcarbamates having a microbicide insecticide and acaricide effect

Abstract

The invention relates to novel compounds of the formula I 1

Description

[0001] The present invention relates to novel N-phenylcarbamates having microbicidal, insecticidal and acaricidal activity, to processes for preparing them, to novel intermediates for preparing them, to agrochemical compositions which comprise these active substances, and to their use in agriculture and in the hygiene field for controlling acarids and insects and for preventing the infestation of crop plants by phytopathogenic fungi.

[0002] The novel N-phenylcarbamates come under the formula (I) 2

[0003] in which

[0004] A is —CH2O— or —CH═N—;

[0005] R1 is C1-C4-alkyl or cyclopropyl;

[0006] R2 is C1-C6-alkyl, C2-C6-alkenyl, or C2-C6-alkynyl or is C1-C6-alkyl substituted by from 1 to 5 fluorine atoms;

[0007] R3 is C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkynyl, C2-C6-alkynyloxy, C1-C6-alkoxycarbonyl or CN, it being possible for the abovementioned: groups except for CN to be substituted by one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, C1-C6-alkoxycarbonyl, C1-C6-alkoxy, C1-C6-alkylthio, aminocarbonyl, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl, C2-C6-alkenyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, heteroaryl and heteroaryloxy, it being possible for the cyclic radicals to be substituted in turn by one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, optionally substituted benzyl, optionally substituted benzyloxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl and optionally substituted heteroaryloxy; or

[0008] R3 is aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, it being possible for the abovementioned groups to be substituted by one or more identical or different substituents selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, halo-C1-C6-alkyl, C1-C6-alkylthio, halo-C1-C6-alkylthio, C1-C6-alkylsulphinyl, halo-C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, halo-C1-C6-alkylsulphonyl, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkynyl, C3-C6-alkynyloxy, C1-C6-alkylcarbonyl, halo-C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, halo-C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, di-(C1-C6-alkyl)-aminocarbonyl, the alkyl groups being identical or different, C1-C6-alkylaminothiocarbonyl, di-(C1-C6-alkyl)-aminothiocarbonyl, the alkyl groups being identical or different, C1-C6-alkylamino, di-(C1-C6-alkyl)-amino, NO2, a C1-C4-alkylenedioxy group which is unsubstituted or substituted from one to four times by C1-C4-alkyl and/or halogen; CN, SF5, OH and QR4;

[0009] Q is a direct bond, oxygen, —O(C1-C6-alkylene)-, —(C1-C6-alkylene)O—, S(═O)p, —S(═O)p(C1-C6-alkylene)-, (C1-C6-alkylene)S(═O)p, C1-C8-alkylene, C2-C6-alkenylene or C2-C6-alkynylene;

[0010] R4 is a C2-C6-alkenyl or C2-C6-alkynyl group which is unsubstituted or substituted by from 1 to 3 halogen atoms; a (C1-C4-alkyl)3Si group, the alkyl groups being identical or different, CN, an unsubstituted or mono- to pentasubstituted C3-C6-cycloalkyl, aryl, heteroaryl or heterocyclyl group, the substituents being selected from the group consisting of halogen, C1-C6-alkyl, halo-C1-C67alkyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, phenoxy, CN, SF5, NO2, C1-C6-alkylsulphinyl, halo-C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, halo-C1-C6-alkylsulphonyl and a C1-C4-alkylenedioxy which is unsubstituted or substituted from one to four times by C1-C4-alkyl and/or halogen;

[0011] p is 0, 1 or 2;

[0012] R5 is hydrogen, C1-C4-alkyl, C1-C2-alkoxymethyl, C1-C2-alkylthiomethyl, C1-C3-haloalkylmethyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C3-alkylcarbonyl or C1-C2-alkoxycarbonyl, and

[0013] R6 is C1-C4-alkyl.

[0014] The formula I is intended to embrace all possible isomeric forms and also mixtures thereof, e.g. racemic mixtures and E/Z mixtures.

[0015] Alkyl as a group per se and also as a structural element of another group, such as of haloalkyl, alkoxy, haloalkoxy, alkylamino, alkylthio, haloalkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl or groups derived therefrom is either straight-chain such as, for example, methyl, ethyl, propyl, butyl, pentyl or hexyl, or branched such as, for example, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.

[0016] Alkenyl as a group per se and also as a structural element of another group such as of haloalkenyl is either straight-chain, such as vinyl, allyl, 1-propenyl, 1-butenyl, 2-buten-1-yl, 3-buten-1-yl, 1-pentenyl or 2-hexenyl, or branched, such as 1-methylvinyl, isopropenyl, isobutenyl or isoamyl.

[0017] Alkynyl as a group per se and also as a structural element of another group, such as of haloalkynyl, is either straight-chain, such as propargyl, 2-butyn-1-yl, 3-butyn-1-yl or 5-hexyn-1-yl, or branched, such as 2-ethynylpropyl or 2-propargylisopropyl.

[0018] Alkylenedioxy is —O(alkylene)O—.

[0019] Alkylene as a group per se and also as a structural element of other groups, such as of O(alkylene), (alkylene)O, S(═O)p(alkylene), (alkylene)S(═O)p or alkylenedioxy, is either straight-chain, such as —CH2CH2—, —CH2CH2CH2— or —CH2CH2CH2CH2— or branched, such as —CH(CH3)—, —CH(C2H5)—, —C(CH3)2—, —CH(CH3)CH2— or —CH(CH3)CH(CH3)—.

[0020] Alkenylene is either straight-chain, such as vin-1,2-ylene, all-1,3-ylene, but-1-en-1,4-ylene or hex-2-en-1,6-ylene, or branched such as 1-methylvin-1,2-ylene.

[0021] Alkynylene is either straight-chain, such as propargylene, 2-butynylene or 5-hexynylene, or branched, such as 2-ethynylpropylene or 2-propargylisopropylene.

[0022] Halogen stands for fluorine, chlorine, bromine or iodine, preferably for fluorine, chlorine or bromine.

[0023] Haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulphinyl or haloalkylsulphonyl may contain identical or different halogen atoms.

[0024] Haloalkylmethyl stands for a haloalkyl, such as 2-chloroethyl, 2-chloropropyl, 2-fluoroethyl, 2-chloro-2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,3,3,3-pentafluoropropyl or 3-bromopropyl, which is attached via a methylene group.

[0025] Aryl is a cyclic aromatic hydrocarbon group such as phenyl, naphthyl or anthracenyl, but preferably phenyl.

[0026] Heteroaryl is a cyclic aromatic group having from 5 to 9 ring members in one or two rings, of which from 1 to 3 members are heteroatoms selected from the group consisting of oxygen, nitrogen and sulphur. One or two benzo rings may be fused onto the heterocycle, attachment to the remainder of the molecule being via either the heterocycle moiety or the benzo moiety. Examples are benzimidazolyl, benzisoxazolyl, benzisothiazolyl, benzocoumarinyl, benzofryl, benzothiadiazolyl, benzothiazolyl, benzothienyl, benzoxazolyl, benzoxadiazolyl, quinazolinyl, quinolyl, quinoxalinyl, carbazolyl, dihydrobenzofuryl, furyl, imidazolyl, indazolyl, indolyl, isoquinolinyl, isothiazolyl, isoxazolyl, methylenedioxyphenyl, ethylenedioxyphenyl, naphthyridinyl, oxazolyl, phenanthridinyl, phthalazinyl, pteridinyl, purinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyrazolo[3,4-b]pyridyl, pyridyl, pyrimidinyl, pyrrolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, thiazolyl, thienyl, triazinyl and triazolyl.

[0027] Preference is given to pyridyl, pyrazinyl, pyrimidinyl, thiazolyl, quinolinyl and thienyl.

[0028] Heterocyclyl is a 5- to 7-membered nonaromatic ring having from 1 to 3 heteroatoms selected from the group consisting of N, O and S. Preference is given to nonaromatic 5-membered and 6-membered rings containing a nitrogen heteroatom and optionally a further heteroatom. Preferred examples are pyrazolinyl, thiazolinyl and oxazolinyl.

[0029] Among the compounds of the formula I, preference is given to those groups in which

[0030] a) R1 is methyl, ethyl or cyclopropyl; or

[0031] b) R1 is methyl; or

[0032] c) R2 is methyl, ethyl, fluoroethyl or trifluoroethyl; or

[0033] d) R2 is methyl; or

[0034] e) R3 is C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkynyl, C3-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy or C1-C6-alkoxycarbonyl, it being possible for the aforementioned groups to be partially or fully halogenated; and also CN, OCN or halogen; or

[0035] f) R3 is phenyl which is unsubstituted or substituted from 1 to 3 times by identical or different substituents selected from halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkynyl, C3-C6-alkynyloxy, C1-C6-alkoxycarbonyl CN, OCN, optionally substituted benzyl, optionally substituted phenyl, or optionally substituted phenoxy, it being possible for the above-mentioned aromatic groups to be substituted by one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino and C2-C6-alkenyl; or

[0036] g) R3 is QR4-substituted phenyl, in which Q is a direct bond, oxygen, OCH2, CH2O, sulphur, CH2—CH2, CH═CH or C≡C and R4 is phenyl which is unsubstituted or substituted 1, or 2: times by identical or different substituents selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkenyloxy, C2-C4-alkynyl, C3-C4-alkynyloxy, C1-C4-alkoxycarbonyl or CN, with QR4 preferably occupying position 4 of the phenyl ring; or

[0037] h) R3 is pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl or pyrazolyl, each unsubstituted or substituted from 1 to 3 times by identical or different radicals from the group consisting of halogen, cyano, nitro, aminocarbonyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkylsulphonyl, C1-C6-alkylsulphinyl, C3-C6-cycloalkyl, optionally substituted arylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl or C2-C6-alkenyl; or

[0038] i) R5 is hydrogen, methyl, ethyl, methoxymethyl, allyl, propargyl, 2,2,2-trifluoroethyl, methylcarbonyl, ethylcarbonyl or methoxycarbonyl; or

[0039] j) R6 is methyl or ethyl; or

[0040] k) R6 is preferably methyl; or

[0041] l) A is —CH2O— or —CH═N—.

[0042] Further preferred subgroups of the formula I are

[0043] (1) compounds of the formula I in which

[0044] R1 is methyl or ethyl, preferably methyl;

[0045] R2 is methyl, ethyl, fluoromethyl or trifluoroethyl, preferably methyl;

[0046] R3 is C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkynyl, C3-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy or C1-C6-alkoxycarbonyl, it being possible for the abovementioned groups to be partly or fully halogenated; and also CN, OCN or halogen; or

[0047] R3 is phenyl which is unsubstituted or substituted from 1 to 3 times by identical or different constituents selected from halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkynyl, C3-C6-alkynyloxy, C1-C6-alkoxycarbonyl, CN, OCN, optionally substituted benzyl, optionally substituted phenyl, or optionally substituted phenoxy, it being possible for the above-mentioned aromatic groups to be substituted by one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino and C2-C6-alkenyl; or

[0048] R3 is pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, which are unsubstituted or substituted from 1 to 3 times by identical or different substituents selected from halogen, cyano, nitro, aminocarbonyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkylsulphonyl, C1-C6-alkylsulphoxyl, C3-C6-cycloalkyl, optionally substituted arylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkyl aminocarbonyl or C2-C6-alkenyl;

[0049] R5 is hydrogen, methyl, ethyl, methoxymethyl, allyl, propargyl, 2,2,2-trifluoroethyl, methylcarbonyl, ethylcarbonyl or methoxycarbonyl, preferably methyl, ethyl, methoxymethyl, allyl or propargyl; and

[0050] A is —CH2O— or —CH═N—;

[0051] (1a) compounds of group (1), in which

[0052] R2 is C1-C6-alkyl, fluoromethyl, difluoromethyl or 2,2,2-trifluoroethyl;

[0053] R3 is C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, CN, C3-C6-cycloalkyl, phenyl which is unsubstituted or substituted from 1 to 3 times by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkenyloxy, C2-C6-alkynyl, C3-C6-alkynyloxy, CN, OCN, benzyl, phenyl, or phenoxy, in which the aromatic groups are unsubstituted or substituted 1 or 2 times by halogen, C1-C2-alkyl, C1-C2-haloalkyl or C1-C2-alkoxy; and

[0054] A is-CH2O—;

[0055] (1b) compounds of group (1a) in which

[0056] R3 is C1-C4-alkyl, C1-C4-alkoxy, or C1-C6-alkoxycarbonyl, or is phenyl which is unsubstituted or substituted 1 or 2 times by halogen, C1-C2-alkyl, C1-C2-haloalkyl or C1-C2-alkoxy;

[0057] (2) compounds of the formula I in which

[0058] R1 is methyl, ethyl or cyclopropyl, preferably methyl;

[0059] R2 is C1-C6-alkyl, preferably methyl or ethyl;

[0060] R3 is C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-alkoxycarbonyl, CN, C3-C6-cycloalkyl, aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, it being possible for the hydrocarbon radicals and the cyclic radicals to be substituted as mentioned previously;

[0061] R5 is hydrogen, methyl, ethyl, methoxymethyl, allyl, propargyl, 2,2,2-trifluoroethyl, methylcarbonyl, ethylcarbonyl or methoxycarbonyl, preferably methyl, ethyl, methoxymethyl, allyl or propargyl; and

[0062] A is —CH2O— or —CH═N—;

[0063] (2a) compounds of group (2) in which

[0064] R3 is C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-alkoxycarbonyl or C3-C6-cycloalkyl; and

[0065] A is —CH2O—;

[0066] (2b) compounds of group (2a) in which

[0067] R3 is phenyl which is unsubstituted or substituted 1 or 2 times by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkenyloxy, benzyl, phenyl or phenoxy, in which these aromatic groups are unsubstituted or substituted 1 or 2 times by halogen, C1-C2-alkyl, C1-C2-haloalkyl or C1-C2-alkoxy; and

[0068] A is —CH2O— or —CH═N—;

[0069] (3) compounds of the formula I in which

[0070] R1 is methyl, ethyl or cyclopropyl;

[0071] R2 is C1-C6-alkyl, preferably methyl or ethyl, C2-C6-alkenyl, preferably allyl or C2-C6-alkynyl, preferably propargyl;

[0072] R3 is phenyl substituted by QR4;

[0073] R5 is hydrogen, methyl, ethyl, methoxymethyl, allyl, propargyl, 2,2,2-trifluoroethyl, methylcarbonyl, ethylcarbonyl or methoxycarbonyl, preferably methyl, ethyl, methoxymethyl, allyl or propargyl; and

[0074] A is —CH2O— or —CH═N—.

[0075] Preferred specific compounds of the formula I are:

[0076] methyl N-methyl-[2-({2-ethoxyimino-1-methyl-2-[4-(4-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0077] methyl N-ethyl-[2-({2-ethoxyimino-1-methyl-2-[4-(4-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0078] methyl N-ethyl-[2-({2-ethoxyimino-1-ethyl-2-[4-(4-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0079] methyl N-methyl-[2-({2-ethoxyimino-1-ethyl-2-[4-(4-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0080] methyl N-methoxymethyl-[2-({2-ethoxyimino-1-methyl-2-[4-(4-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0081] methyl N-propargyl-[2-({2-methoxyimino-1-methyl-2-[4-(4-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0082] methyl N-propargyl-[2-({2-ethoxyimino-1-methyl-2-[4-(4-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0083] methyl N-propargyl-[2-({2-ethoxyimino-1-ethyl-2-[4-(4-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0084] methyl N-propargyl-[2-({2-ethoxyimino-1-ethyl-2-[4-(4-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0085] methyl N-methyl-[2-({2-methoxyimino-1-methyl-2-(4-chlorophenyl)ethylidene}-hydrazonomethyl)phenyl]carbamate,

[0086] methyl N-methyl-[2-({2-methoxyimino-1-methyl-2-(4-fluorophenyl)ethylidene}-hydrazonomethyl)phenyl]carbamate,

[0087] methyl N-methoxyethyl-[2-({2-methoxyimino-1-methyl-2-(4-chlorophenyl)ethylidene}hydrazonomethyl)phenyl]carbamate,

[0088] methyl N-methoxyethyl-[2-({2-methoxyimino-1-methyl-2-(4-fluorophenyl)ethylidene}hydrazonomethyl)phenyl]carbamate,

[0089] methyl N-methyl-[2-({2-methoxyimino-1-methyl-2-[4-(3-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0090] methyl N-methyl-[2-(.{2-ethoxyimino-1-ethyl-2-[4-(3-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0091] methyl N-methyl-[2-({2-ethoxyimino-1-ethyl-2-[4-(3-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0092] methyl N-methyl-[2-({2-methoxyimino-1-methyl-2-[4-(4-chloromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0093] methyl N-methyl-[2-({2-ethoxyimino-1-methyl-2-[4-(4-chloromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate,

[0094] methyl N-methyl-{2-[2-(4-fluorophenyl)-2-methoxyimino-1-methyl-ethylideneaminooxymethyl]phenyl}carbamate,

[0095] methyl N-ethyl-{2-[2-methyl-2-methoxyimino-1-methyl-ethylideneaminooxymethyl]phenyl}carbamate,

[0096] methyl N-ethyl-{2-[2-(4-fluorophenyl)-2-methoxyimino-1-methyl-ethylideneaminooxymethyl]phenyl}carbamate,

[0097] methyl N-methoxymethyl-{2-[2-methyl-2-methoxyimino-1-methyl-ethylideneaminooxymethyl]phenyl}carbamate, and

[0098] methyl N-methyl-{2-[2-(4-(4-trifluoromethylphenoxy)phenyl)-2-ethoxyimino-1-methylethylideneaminooxymethyl]phenyl}carbamate.

[0099] Compounds of the formula I may be prepared as follows:

[0100] A) A compound of the formula I in which A is —CH═N— may be prepared by reacting a hydrazone of the general formula II 3

[0101]  in which R1, R2 and R3 have the meanings indicated under formula I with an aldehyde of the general formula III or one of its acetal or imino derivatives of the general formulae IVa and IVb 4

[0102]  in which R is C1-C6-alkyl or the two Rs together with the two oxygen atoms and the carbon to which they are attached are a cyclic acetal.

[0103] The compounds of the general formulae II and III are known from the literature (e.g. P. Y. Chong; S. Z. Janicki; P. A. Petillo; J. Org. Chem. (1998), 63(23), 8515-8521, J. M. Muchowski; M. C. Venuti;. J. Org. Chem. (1980), 45(23), 4798-801, S. Witek; J. Bielawski; A. Bielawska; PL-98698, CA 91:91384; Müller, B. et al.; WO 93/15046 (BASF)) or may be prepared by known methods. The compounds of the general formulae IVa and WVb may be obtained in analogy to the methods described under C) and D) or directly from the carbonyl derivatives of the formula III.

[0104] B) A compound of the formula I in which A is CH2O may be prepared by reacting an oxime of the general formula V 5

[0105]  in which R1, R2 and R3 have the meanings indicated under formula I with a benzyl derivative of the general formula VI, 6

[0106]  in which R5 and R6 have the meanings indicated under formula I and U is a leaving group (e.g. chlorine, bromine, tosyloxy, mesyloxy).

[0107] The compounds of the general formulae V and VI are known (e.g. H. Ziegler et al; WO 95/18789 (Novartis), Y. Shiokawa et al; EP-A-268989 (Fujisawa Pharm.)) or may be prepared by known methods.

[0108] C) A compound of the formula I in which R5 is C1-C4-alkyl, C1-C2-alkoxymethyl, C1-C2-alkylthiomethyl, C1-C3-haloalkylmethyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C3-alkylcarbonyl or C1-C2-alkoxycarbonyl may be prepared by reacting a compound of the formula Ia 7

[0109]  in which A, R1, R2, R3 and R6 have the meanings indicated under formula I with a compound of the general formula VII,

R5a-Hal  VII

[0110]  in which R5a with the exception of hydrogen has the meanings indicated for R5 and Hal stands for chlorine, bromine or iodine.

[0111] D) A compound of the formula I may be prepared by reacting an aniline derivative of the general formula VIII 8

[0112]  in which R1, R2, R3 and R5 have the meanings indicated under formula I with a chloroformate of the general formula IX

Cl—COOR6  IX

[0113] The compounds of the formula VIII are novel, and may be prepared by

[0114] a) condensing a hydrazone of the formula II with an aldehyde of the formula X or one of its acetal or imino derivatives 9

[0115]  in which R5 has the meanings indicated under formula I and R has the meanings indicated under formula TV. The compounds of the formulae X, XIa and XIb are known (e.g. T. Sugasawa; H. Hamana; T. Toyota; M. Adachi, JP-55002626 or T. Sugasawa; H. Hamana; T. Toyoda; M. Adachi; Synthesis (1979), (2), 99-100 or W. Heinzelmann; Helv. Chim. Acta (1978), 61(2), 618-25) or may be prepared by known methods, or

[0116] b) condensing a ketone of the formula XII 10

[0117]  in which R1-R3 have the meanings described under formula I with a hydrazone of the formula XIII 11

[0118]  in which R5 has the meanings indicated under formula I. The compounds of the formula XIII are known (e.g. Adger et al; J. Chem. Soc. Perkin Trans.1; 1975; pp. 31, 33, 36, 37) and may be prepared by condensing the aldehydes X with hydrazine;

[0119] c) reacting a benzyl derivative of the general formula XIV 12

[0120]  in which R5 has the meanings indicated under formula I and U is a leaving group (e.g. chlorine, bromine, tosyloxy, mesyloxy) with an oxime of the general formula V. 13

[0121] The compounds of the formula XIV are known (cf. e.g. M. Uehara; T. Shimizu; N. Abe; A. Seo; JP-10298156 or J. Liu; R. H. Dodd; J. Heterocycl. Chem. (1995), 32(2), 523-8 or B. Mueller; H. Sauter; F. Roehl; R. Doetzer; G. Lorenz; E. Ammermann; WO 93/15046).

[0122] E) A compound of the formula I may be prepared by etherifying an oxime of the general formula XV 14

[0123]  in which R1, R3, R5 and R6 have the meanings indicated under formula I.

[0124] The compounds of the formula XV are novel and may be obtained by

[0125] a) reacting a ketone of the general formula XVI 15

[0126]  in which R1, R3, R5 and R6 have the meanings indicated under formula I with hydroxylamine or one of its salts, or

[0127] b) reacting a compound of the general formula XVII 16

[0128]  in which R1, R3, R5 and R6 have the meanings indicated under formula I with nitrous acid or an alkyl nitrite in the presence of an acid or base, or

[0129] c) reacting a hydrazone of the general formula XVIII 17

[0130]  in which R1 and R3 have the meanings indicated under formula I with an aldehyde or ketone of the general formula III or an acetal or imine of the general formulae IVa or IVb, respectively, as described under A).

[0131] The compounds of the formulae XVI and XVII in which A is —CH═N— are novel and may be obtained in analogy to the preparation of the compounds of the formula I. The compounds of the formulae XVI and XVII in which A is —CH2—O— are known (e.g. T. Komyoji; I. Shigehara; N. Matsuo; H. Shimoharada; T. Ohshima; T. Akagi; S. Mitani; EP-A-498396 or N. Matsuo; H. Shimoharada; T. Ooshima; S. Mitani; K. Myashita; JP-06056756) or may be obtained by the methods described herein.

[0132] The compounds of the formula XVIII are known (e.g. Barany et al., J. Chem. Soc.1951, 1929; Neber; Hartung, Ruopp, Chem. Ber., 58, 1925, 1240; H. Gnichtel;, B. Toepper Liebigs Ann. Chem., GE, 1989, 1071-1074; H. Rapoport; W. Nilsson, J. Amer. Chem. Soc., 83, 1961, 4262-4267).

[0133] F) A compound of the formula I may be prepared by reacting a ketone of the general formula XVI with an alkoxyamine of the general formula XIX

R2—ONH2  XIX

[0134]  in which R2 has the meanings indicated under formula I or with one of its salts.

[0135] All of the reactions described above are known per se. The novel, abovementioned intermediates have been developed specifically for the present invention and likewise form a subject of this invention; of particular significance are those of the formulae VIII, XV, XVIa and XVIIa. 18

[0136] The compounds of the formula I may be employed preventively and/or curatively in the agricultural sector and related fields as active substance in the control of plant pests. The active substances of the formula I according to the invention are distinguished by good activity, even when applied at low concentrations, and by good plant tolerance and environment-friendliness. They possess very advantageous, especially systemic, properties and may be used to protect a large number of crop plants. Using the active substances of the formula I it is possible to contain or destroy the pests which occur on plants or parts of plants (fruits, flowers, foliage,; stalks, tubers, roots) of various crops, with even plant parts which grow at a later point in time remaining unharmed by, for example, phytopathogenic microorganisms.

[0137] The compounds I may further be used as dressing agents for treating seed (fruits, tubers, kernels) and plant cuttings for protecting against fungal infections and against soil-borne phytopathogenic fungi.

[0138] The compounds I are effective, for example, against the following classes of phytopathogenic fungi: Fungi imperfecti (e.g. Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria); Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia); Ascomycetes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and Oomycetes (e.g. Phytophthora, Pythium, Plasmopara).

[0139] Target crops for use in plant protection in the context of the invention are, for example, the following plant species: cereals (wheat, barley, rye, oats, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pome fruit, stone fruit, and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); legumes (beans, lentils, peas, soya); oil crops (oilseed rape, mustard, poppies, olives, sunflowers, coconut, castor, cocoa, peanuts); cucurbits (pumpkin, cucumbers, melons); fiber crops (cotton, flax, hemp, jute); citrus fruits (oranges, lemons, grapefruit, tangerines); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, bell peppers); the laurel family (avocado, Cinnamonium, camphor) and plants such as tobacco, nuts, coffee, aubergines, sugarcane, tea, pepper, grapevines, hops, the plantain family, latex plants, and ornamentals.

[0140] Further, the compounds of the formula I according to the invention combine good tolerance by warm-blooded species, fish and plants with valuable activity against insects and pests from the order Acarina, such as occur on crop plants and ornamentals in agriculture, in horticulture and in forestry. The compounds of the formula I are particularly suitable for controlling pests in cotton, vegetable, fruit and rice crops, such as spider mites, aphids, caterpillars of lepidopterans and rice leafhoppers. Primary among the pests which can be controlled are spider mites such as Panonychus ulmi, aphids such as Aphis craccivora, lepidopteran caterpillars such as those of Heliothis virescens, and rice leafhoppers such as Nilaparvata lugens or Nephotettix cincticeps.

[0141] The good pesticidal activity of the compounds I according to the invention corresponds to a mortality of at least 50-60% of the pests mentioned.

[0142] Further fields of use of the active substances according to the invention are in the protection of stored products and of materials, where the product in storage is protected against rotting and moulding and also against animal pests (e.g. grain weevils, mites, maggots, etc.). In the hygiene sector, compounds of the formula I effect successful control of animal parasites such as ticks, mites, warble flies, etc. on domestic animals and productive livestock. The compounds I are effective against all or individual development stages of both normally sensitive and resistant species of pests. Their activity may be manifested, for example, in killing of the pests, either Immediately or only after a certain time has elapsed, during ecdysis for example, or in reduced oviposition and/or hatching rate.

[0143] The compounds I are used in unmodified form or, preferably, together with the auxiliaries customary in the art of formulation. For this purpose they are appropriately processed to, for example, emulsifiable concentrates, spreadable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts or granules, by means, for example, of encapsulation in, for example, polymeric substances, in a known manner. The application techniques, such as spraying, misting, dusting, broadcasting, brushing on or pouring, like the nature of the compositions, are chosen in accordance with the desired objectives and the prevailing circumstances.

[0144] Suitable carriers and additives may be soluble or liquid and are substances which are appropriate in the art of formulation, examples being natural or regenerated minerals, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers.

[0145] The compounds of the formula I may be mixed with further active substances, examples being fertilizers, trace element providers or other crop protection agents, particularly further fungicides. In this context, unexpected synergistic effects may anse.

[0146] Preferred co-components are:

[0147] azoles, such as azaconazole, bitertanole, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafole, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazol, pyrifenox, prochloraz, propiconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole;

[0148] pyrimidinyl-carbinols, such as ancymidbl, fenarimol, nuarimol;

[0149] 2-aminopyrimidines, such as bupirimate, dimethirimol, ethirimol;

[0150] morpholines, such as dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph;

[0151] anilinopyrimidines, such as cyprodinil, mepanipyrim, pyrimethanil;

[0152] pyrroles, such as fenpiclonil, fludioxonl;

[0153] phenylamides, such as benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace, oxadixyl;

[0154] benzimidazoles, such as benomyl, carbendazim, debacarb, fuberidazole, thiabendazole;

[0155] dicarboximides, such as chlozolinate, dichlozoline, iprodione, myclozolin, procymidon, vinclozolin;

[0156] carboxamides, such as carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, thifluzamide;

[0157] guanidines, such as guazatine, dodine, iminoctadine;

[0158] strobilurins, such as azoxystrobin, kresoxim-methyl, metominostrobin, SSF-126, SSF-129, trifloxystrobin;

[0159] dithiocarbamates, such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, ziram;

[0160] N-halomethylthiophthalimides, such as captafol, captan, dichlofluanid, fluoromide, folpet, tolyfluanid;

[0161] Cu compounds, such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulphate, cuprous oxide, mancopper, oxine-copper;

[0162] nitrophenol derivatives, such as dinocap, nitrothal-isopropyl;

[0163] organophosphorus derivatives, such as edifenphos, iprobenphos, isoprothiolane, phosdiphen, pyrazophos, tolclofos-methyl;

[0164] miscellaneous, such as AC 382042, acibenzolar S-methyl, anilazine, blasticidin S, chinomethionat, chloroneb, chlorothalonil, cymoxanil, dichlone, diclomezine, dicloran, diethofencarb, dimethomorph, dithianon, etridiazole, famoxadone, fenamidone, fenhexamid, fentin, ferimzone, fluazinam, flusulphamide, fenhexamid, fosetyl-aluminium, hymexazol, IKF-916, iprovalicarb, kasugamycin, methasulphocarb, MON 65500, pencycuron, phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxyfen, quintozene, RH-7281, sulphur, triazoxide, tricyclazole, triforine, validamycin.

[0165] One preferred method of applying an active substance of the formula I or an agrochemical composition comprising at least one of these active substances is application to foliage (foliar application). Frequency and rate of application depend on the risk of infestation by the pathogen in question. Alternatively, the active substances I may reach the plant through the soil by the root system (systemic action), by drenching the locus of the plant with a liquid preparation or by incorporating the substances in solid form into the soil, in the form for example of granules (soil application). In the case of paddy rice crops, such granules may be metered into the flooded paddy field. Alternatively, the compounds I may be applied to seed kernels for the purpose of seed treatment (coating), either by soaking the kernels or tubers in a liquid preparation of the active substance or by coating them with a solid preparation.

[0166] The compositions are prepared conventionally, for example by intimately mixing and/or grinding the active substance with extenders, such as solvents, solid carriers and, if desired, surface-active compounds (surfactants).

[0167] The agrochemical compositions generally contain from 0.1 to 99 percent by weight, in particular from 0.1 to 95 percent by weight, of active substance of the formula I, from 99.9 to 1 percent by weight, in particular from 99.8 to 5 percent by weight, of a solid or liquid additive and from 0 to 25 percent by weight, in particular from 0.1 to 25 percent by weight, of a surfactant.

[0168] Favourable application rates are generally from 1 g to 2 kg of active substance (AS) per hectare (ha), preferably from 10 g to 1 kg AS/ha, in particular from 20 g to 600 g AS/ha.

[0169] In the case of use as a seed dressing agent, amounts used with advantage are from 10 mg to 1 g of active substance per kg of seed.

[0170] While concentrated compositions tend to be preferred as commercial product, the end user generally uses diluted compositions.

[0171] The compositions may also comprise further additives, such as stabilizers, defoamers, viscosity regulators, binders or adhesives, and also fertilizers or other active substances for obtaining specific effects.

PREPARATION EXAMPLES

[0172] Scheme 1 shows in overview the synthesis pathways and intermediates used for preparing the compounds of the formula I in which A is the —CH2O— bridge. 19

[0173] Physical data are reported in the subsequent tables

[0174] m.p. in ° Celsius; * isomers; Chem. shift in 1H-NMR in ppm; t=triplet; q=quartet; s=singlet; br=broad

Example Z1

Methyl (2-formylphenyl)methylcarbamate

[0175] 20

[0176] A solution of 2.6 g of methyl (2-formylphenyl)carbamate (J. Org. Chem. 1998, 63(23), 8515) in 10 ml of dimethylformamide is added dropwise at room temperature to a suspension of 0.64 g of sodium hydride (55% in oil) in 15 ml of dimethylformamide and the mixture is subsequently stirred at room temperature for 15 minutes. Then 2.2 g of methyl iodide are added and the reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is worked up by being acidified with acetic acid and concentrated under a high vacuum. The residue is taken up in ethyl acetate, washed twice with water and twice with saturated sodium chloride solution, dried over sodium sulphate and concentrated by evaporation under vacuum. The crude product is purified by column chromatography (silica gel; ethyl acetate:hexane=1:3). This gives the desired methyl (2-formylphenyl)methylcarbamate as an oil.

[0177] 1 H-NMR(CDCl3): inter alia 3.46 (s); 10.1 (s).

[0178] The following compounds as well are prepared analogously:

21
R5	Phys. data	1H-NMR(CDCl3)
C2H5	Oil	i.a. 1.18 (t); 3.78 (q); 10.2 (s)
HC≡C—CH2—	Oil	i.a. 2.28 (t); 4.48 (br); 10.13 (s)
H3C—O—CH2—	Oil	i.a. 3.52 (br); 4.96 (br); 10.0 (s)

Example Z2

Methyl {2-[2-(4-fluorophenyl)-1-methyl-2-oxo-(E)-ethylideneaminooxymethyl]phenyl}carbamate

[0179] 22

[0180] 9.0 g of 1-(4-fluorophenyl)propane-1,2-dione 2-(E)-oxime and 6.9 g of potassium carbonate are introduced in 150 ml of acetonitrile. After 15 minutes, 10.0 g of methyl (2-chloromethylphenyl)carbamate (Fujisawa Pharm., EP-A-268989) are added with stirring. After two hours, the mixture is evaporated to dryness, the residue is partitioned between water and ethyl acetate and the residue from the evaporated organic phase is purified on silica gel using ethyl acetate/hexane (1:4 volume fractions) as eluent. This gives 1 g of methyl {2-[2-(4-fluorophenyl)-1-methyl-2-oxo-(E)-ethylideneaminooxymethyl]phenyl}carbamate in the form of colourless crystals (m.p. 71-73° C.).

Example Z3

Methyl {2-[2-(4-fluorophenyl)-1-methyl-2-oxo-(E)-ethylideneaminooxymethyl]phenyl}methylcarbamate

[0181] 23

[0182] 1.72 g of methyl {2-[2-(4-fluorophenyl)-1-methyl-2-oxo-(E)-ethylideneaminooxymethyl]phenyl}carbamate are added in portions with stirring to a suspension of 0.2 g of sodium hydride (approximately 60% in mineral oil) in 5 ml of dimethylformamide. After the end of evolution of hydrogen, the mixture is cooled in an ice-water bath and 0.31 ml of methyl iodide is added dropwise. After the mixture has been stirred at room temperature for two hours, ice-water is added and the product is extracted with ethyl acetate. The residue of the evaporated organic phase is purified on silica gel using ethyl acetate/hexane (1:5 volume fractions) as eluent. This gives methyl {2-[2-(4-fluorophenyl)-1-methyl-2-oxo-(E)-ethylideneaminooxymethyl]phenyl}methylcarbamate as a colourless oil.

[0183] 1 H-NMR(CDCl3): inter alia 3.59 (s) and 3.76 (s): NCH3 (rotamers 3:1).

Example Z4

2-[2-(2-Methoxyimino-1-methylpropylideneaminooxymethyl)]aniline

[0184] 24

[0185] A suspension of 23.29 g of iron powder, 30 ml of water, 0.5 ml of concentrated hydrochloric acid and 150 ml of ethanol is heated to boiling temperature. After the heating source has been removed, 34.57 g of 2-[2-(2-methoxyimino-1-methylpropylideneaminooxymethyl)]nitrobenzene are added in portions with stirring and under nitrogen in such a way that the reaction solution remains at boiling temperature. After subsequently stirring at room temperature for 1.5 hours, the reaction mixture is filtered over Celite and the filtrate is concentrated by evaporation. Recrystallization of the residue from tert-butanol gives the desired 2-[2-(2-methoxyimino-1-methylpropylideneaminooxymethyl)]aniline as pale yellow crystals (m.p. 90-91° C.).

Example Z5

Methyl N-ethyl-[2-(2-hydroxyimino-1-methylpropylideneaminooxymethyl)phenyl]carbamate

[0186] 25

[0187] A solution of 710 mg of methyl ethyl[2-(1-methyl-2-oxo-propylideneaminooxymethyl)phenyl]carbamate, 280 mg of hydroxylamine hydro chloride and 0.3 ml of pyridine in 10 ml of ethanol is stirred at room temperature for 22 hours. The mixture is partitioned between ethyl acetate and half-saturated sodium chloride solution and the oil which remains after evaporating off the organic solvent is purified on silica gel using ethyl acetate/hexane (1:4 volume fractions) as eluent. The chromatographed oil can be crystallized from toluene/heptane (1:1 volume fractions). This gives methyl N-ethyl-[2-(2-hydroxyimino-1-methylpropylidene aminooxymethyl)phenyl]carbamatein isomerically pure form as pale yellow crystals (m.p. 84-85° C.).

Example H1

Methyl N-methyl-[2-({2-ethoxyimino-1-methyl-2-[4-(4-trifluoromethylphenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate

[0188] 26

[0189] A mixture of 1.32 g of 2-hydrazono-1-[4-(4-trifluoromethylphenoxy)phenyl]propan-1-one O-ethyl oxime and 0.7 g of methyl N-methyl-(2-formylphenyl)carbamate in 6 ml of methanol is stirred at room temperature for 45 minutes. The reaction mixture is worked up by being concentrated under vacuum and the crude product is purified by column chromatography (silica gel; ethyl acetate:hexane=1:3). This gives the desired methyl N-methyl-[2-(f{2-ethoxyimino-1-methyl-2-[4-(4-trifluoromethyl phenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate as a resin.

[0190] The following compounds as well are prepared analogously:

TABLE a
27
					Phys.	1H-NMR of R1
No.	R5	R1	R2	R′	Data	(CDCl3)
1	CH3	CH3	C2H5	4-CF3—C6H4—O—	Resin	2.29 (s)1
2	C2H5	CH3	C2H5	4-CF3—C6H4—O—	Resin	2.27 (s)1
3	C2H5	C2H5	C2H5	4-CF3—C6H4—O—	Resin	1.01(t); 2.28(q)1
4	CH3	C2H5	C2H5	4-CF3—C6H4—O—	Resin	1.11(t); 2.81(q)1
5	H3C—O—CH2—	CH3	C2H5	4-CF3—C6H4—O—	Resin	2.28 (s)1
6	HC≡C—CH2—	CH3	CH3	4-CF3—C6H4—O—	Resin	2.31 (s)
7	HC≡C—CH2—	CH3	C2H5	4-CF3—C6H4—O—	Resin	2.32 (s)
8	HC≡C—CH2—	C2H5	CH3	4-CF3—C6H4—O—	Resin*	1.16(t); 2.88(q)
						1.24(t); 2.51(q)
9	HC≡C-CH2—	C2H5	C2H5	4-CF3—C6H4—O—	Resin	1.17(t); 2.91(q)
10	CH3	CH3	CH3	Cl	116-118°
11	CH3	CH3	CH3	F	129-131°
12	H3C—O—CH2—	CH3	CH3	Cl	106-131°
13	H3C—O—CH2—	CH3	CH3	F	142-144°
14	CH3	CH3	CH3	3-CF3O—C6H4—O—	Resin	2.32 (s)
15	CH3	C2H5	CH3	3-CF3O—C6H4—O—	Resin	1.26(t); 2.89(q)
16	CH3	C2H5	C2H5	43CF3O—C6H4—O—	Resin	1.26(t); 2.91(q)
17	CH3	CH3	CH3	4-Cl—C6H4—O—	Resin	2.32 (s)
18	CH3	CH3	C2H5	4-Cl—C6H4—O—	Resin	2.33 (s)
1) in DMSO-d6

Example H2

Methyl [2-(2-(E)-methoxyimino-1-methyl-(E)-propylideneaminooxymethyl)phenyl]carbamate

[0191] 28

[0192] A solution of 9.41 g of 2-[2-(2-methoxyimino-1-methylpropylideneaminooxymethyl)]aniline and 3.54 ml of pyridine in 30 ml of dichloromethane is admixed with 3.1 ml of methyl chloroformate over 20 minutes with stirring and in the absence of oxygen. The temperature is maintained at +40° C. for 1.5 hours and then the product is washed with ice-water and the crystal cake which remains after the solvent has been evaporated off is recrystallized from tert-butanol. This gives methyl [2-(2-(E)-methoxyimino-1-methyl-(E)-propylideneaminooxymethyl)phenyl]carbamate in the form of colourless crystals (m.p. 96.5-97.5° C.).

Example H3

Methyl N-methoxymethyl-[2-(2-(E)-methoxyimino-1-methyl-(E)-propylideneaminooxymethyl)phenyl]carbamate

[0193] 29

[0194] A solution of 2.93 g of methyl [2-(2-(E)-methoxyimino-1-methyl-(E)-propylideneaminooxymethyl)phenyl]carbamate in 5 ml of dimethylformamide is added dropwise with stirring and under nitrogen to a suspension of 300 mg of sodium hydride (as an 80% dispersion in white oil) in. 5 ml of dimethylformamide. After the end of evolution of hydrogen, the reaction solution is admixed with 0.84 ml of chloromethyl methyl ether, with ice cooling. After two hours, the reaction mixture is poured onto ice-water and extracted with ethyl acetate. Following the removal of the solvent by evaporation, the extract is purified on silica gel using ethyl acetate/hexane (1:4 volume fractions) as eluent. This gives methyl N-methoxytnethyl-[2-(2-(E)-methoxyimino-1-methyl-(E)-propylideneaminooxymethyl)phenyl]carbamate in the form of colourless crystals (m.p. 103-104° C.).

Example H4

Methyl N-ethyl-[2-(2-(E)-methoxyimino-1-methyl-(E)-propylideneaminooxymethyl)phenyl]carbamate

[0195] 30

[0196] A solution of 3.1 g of methyl (2-bromomethylphenyl)ethylcarbamate (approximately 50% strength) and 911 mg of butane-2,3-dione (E)-O-methyloxime (E)-oxime in 10 ml of dimethylformamide is added with stirring and under nitrogen, and with ice cooling, to a suspension of 369 mg of sodium hydnrde (as an 80% dispersion in white oil) and one spatula tip of potassium iodide in 10 ml of dimethylformamide. After subsequent stirring at room temperature for 18 hours, the reaction mixture is partitioned between water and ethyl acetate. The residue obtained after the organic solvent has been distilled off is purified on silica gel using ethyl acetate/hexane (1:9 volume fractions) as eluent, with subsequent recrystallization from hexane. This gives methyl N-ethyl-[2-(2-(E)-methoxyimino-1-methyl-(E)-propylideneaminooxymethyl)phenyl]carbamate in the form of colourless crystals (m.p. 101-102° C.).

Example H5

Methyl N-methyl-{2-[2-(4-fluorophenyl)-2-(E/Z)-methoxyimino-1-methyl-(E)-ethylideneaminooxymethyl]phenyl}carbamate

[0197] 31

[0198] 0.8 g of methyl N-methyl-{2-[2-(4-fluorophenyl)-1-methyl-2-oxo-(E)-ethylideneaminooxymethyl]phenyl}carbamate, 0.42 g of O-methylhydroxylamine hydrochloride and 5 ml of pyridine are stirred at +60° C. for 4 hours. After cooling, ice-water is added and the product is extracted with ethyl acetate. The extract concentrated by evaporation is purified on silica gel using ethyl acetate/hexane (1:2 volume fractions) as eluent. This gives methyl N-methyl-{2-[2-(4-fluorophenyl)-2-(E/Z)-methoxyimino-1-methyl-(E)-ethylidencaminooxymethyl]phenyl}carbamate as an isomer mixture in the form of a yellowish resin.

[0199] 1 H-NMR(CDCl3): inter alia 3.06 (s) and 3.20 (s): NCH3.

Example H6

Methyl {2-[2-(4-fluorophenyl)-2-(E)-methoxyimino-1-methyl-(Z)-ethylideneaminooxymethyl]phenyl}carbamate

[0200] 32

[0201] A mixture of 3.0 g of methyl (2-chloromethylphenyl)carbamate (Fujisawa Pharm., EP-A-268989), 3.0 g of 1-(4-fluorophenyl)propane-1,2-dione 1-(E)-O-methyloxime 2-(Z)-oxime and 2.1 g of potassium carbonate in 50 ml of acetonitrile is stirred at room temperature for 20 hours. After the solvent has been evaporated off, the residue is partitioned between water and ethyl acetate and the residue of the organic phase is purified on silica gel using ethyl acetate/bexane (from 1:4 to 1:2 volume fractions) as eluent. This gives methyl {2-[2-(4-fluorophenyl)-2-(E)-methoxyimino-1-methyl-(Z)-ethylideneaminooxymethyl]phenyl}carbamate in the form of colourless crystals (m.p. 143-144° C.).

Example H7

Methyl {2-[2-(4-fluorophenyl)-2-(E/Z)-methoxyimino-1-methyl-(E)-ethylideneaminooxymethyl]phenyl}carbamate

[0202] 33

[0203] 6.9 g of methyl {2-[2-(4-fluorophenyl)-1-methyl-2-oxo-(E)-ethylideneaminooxymethyl]phenyl}carbamate, 2.5 g of O-methylhydroxylamine hydrochloride and 25 ml of pyridine are held at +70° C. for 4 hours with stirring. After cooling, the mixture is poured onto ice-water and extracted with ethyl acetate. Distillative removal of ethyl acetate and pyridine residues gives methyl {2-[2-(4-fluorophenyl)-2-(E/Z)-methoxyimino-1-methyl-(E)-ethylideneaminooxymethyl]phenyl}carbamate as an isomer mixture in the form of a yellowish resin.

[0204] 1 H-NMR(CDCl3): inter alia 4.98 (s) and 5.06 (s): OCH2phenyl.

Example H8

Methyl N-ethyl-{2-[2-(4-fluorophenyl)-2-(E/Z)-methoxyimino-1-methyl-(E)-ethylideneaminooxymethyl]phenyl}carbamate

[0205] 34

[0206] 100 mg of sodium hydride (as an approximately 60% dispersion in mineral oil) are added with stirring in the absence of oxygen to a solution of 750 mg of methyl {2-[2-(4-fluorophenyl)-2-(E/Z)-methoxyimino-1-methyl-(E)-ethylideneaminooxymethyl]-phenyl}carbamate in 5 ml of dimethylformamide. After the end of evolution of hydrogen, ethyl bromide is added dropwise at room temperature, the reaction mixture is stirred for 2 hours, ice-water is added and the mixture is extracted with ethyl acetate. The extract concentrated by evaporation is purified on silica gel using ethyl acetate/hexane (1:2 volume fractions) as eluent. This gives methyl N-ethyl-{2-[2-(4-fluorophenyl)-2-(E/Z)-methoxyimino-1-methyl-(E)-ethylideneaminooxymethyl]-phenyl}carbamate as a mixture of two isomers in the form of a yellowish resin.

[0207] 1 H-NMR(CDCl3): inter alia 4.95 (q) and 5.12 (q): OCH2phenyl.

[0208] The following compounds as well are prepared analogously:

TABLE b
35
No.	R5	R1	R2	R3	R6	Phys. Data
1	H	CH3	CH3	CH3	CH3	96.5-97.5°
2	H	CH3	CH3	C6H5	CH3	Resin
3	H	CH3	CH3	4-F—C6H4—	CH3	143-144°
						(Z, E isomer)
4	H	CH3	CH3	4-F—C6H4—	CH3	Resin*
						(E, E/E, Z
						mixture)
5	H	CH3	CH3	CH3	C4H9-t	Resin*
6	CH3	CH3	CH3	4-F—C6H4—	CH3	Resin*
7	C2H5	CH3	CH3	CH3	CH3	101-102°
8	C2H5	CH3	CH3	4-F—C6H4—	CH3	Resin*
9	CH3—O—CH2—	CH3	CH3	CH3	CH3	103-104°
10	H	CH3	C2H5	4-CF3—C6H4-4-	CH3	150-152°
				O—C6H4—
11	CH3	CH3	C2H5	4-CF3—C6H4-4-	CH3	Resin
				O—C6H4—

[0209] The compounds of the following tables may be prepared analogously.

[0210] Table 1

[0211] Compounds of the general formula I.1 in which R2, R5 and R6 are methyl and R3 corresponds in each case to one line of table A. 36

[0212] Table 2

[0213] Compounds of the general formula I.1 in which R2 is ethyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0214] Table 3

[0215] Compounds of the general formula I.1 in which R2 is difluoromethyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0216] Table 4

[0217] Compounds of the general formula I.1 in which R2 is 2,2,2-trifluoroethyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0218] Table 5

[0219] Compounds of the general formula I.1 in which R2 and R6 are methyl and R5 is ethyl and R3 corresponds in each case to one line of table A.

[0220] Table 6

[0221] Compounds of the general formula I.1 in which R2 and R6 are ethyl and R5 is methyl and R3 corresponds in each case to one line of table A.

[0222] Table 7

[0223] Compounds of the general formula I.1 in which R2 and R5 are ethyl and R6 is methyl and R3 corresponds in each case to one line of table A.

[0224] Table 8

[0225] Compounds of the general formula I.1 in which R2 is methyl and R5 and R6 are ethyl and R3 corresponds in each case to one line of table A.

[0226] Table 9

[0227] Compounds of the general formula I.1 in which R2, R5 and R6 are ethyl and R3 corresponds in each case to one line of table A.

[0228] Table 10

[0229] Compounds of the general formula I.1 in which R2 is n-propyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0230] Table 11

[0231] Compounds of the general formula I.1 in which R2 and R6 are methyl and R5 is methoxymethyl and R3 corresponds in each case to one line of table A.

[0232] Table 12

[0233] Compounds of the general formula I.2 in which R2, R5 and R6 are methyl and R3 corresponds in each case to one line of table A. 37

[0234] Table 13

[0235] Compounds of the general formula I.2 in which R2 is ethyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0236] Table 14

[0237] Compounds of the general formula I.2 in which R2 is difluoromethyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0238] Table 15

[0239] Compounds of the general formula I.2 in which R2 is 2,2,2-trifluoroethyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0240] Table 16

[0241] Compounds of the general formula I.2 in which R2 and R6 are methyl and R5 is ethyl and R3 corresponds in each case to one line of table A.

[0242] Table 17

[0243] Compounds of the general formula I.2 in which R2 and R5 are ethyl and R6 is methyl and R3 corresponds in each case to one line of table A.

[0244] Table 18

[0245] Compounds of the general formula I.2 in which R2 and R6 are ethyl and R5 is methyl and R3 corresponds in each case to one line of table A.

[0246] Table 19

[0247] Compounds of the general formula I.2 in which R2 is methyl and R5 and R6 are ethyl and R3 corresponds in each case to one line of table A.

[0248] Table 20

[0249] Compounds of the general formula I.2 in which R2, R5 and R6 are ethyl and R3 corresponds in each case to one line of table A.

[0250] Table 21

[0251] Compounds of the general formula I.2 in which R2 is n-propyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0252] Table 22

[0253] Compounds of the general formula I.2 in which R2 and R6 are methyl and R5 is methoxymethyl and R3 corresponds in each case to one line of table A.

[0254] Table 23

[0255] Compounds of the general formula I.3 in which R2, R5 and R6 are methyl and R3 corresponds in each case to one line of table A. 38

[0256] Table 24

[0257] Compounds of the general formula I.3 in which R2 is ethyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0258] Table 25

[0259] Compounds of the general formula I.3 in which R2 is difluoromethyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0260] Table 26

[0261] Compounds of the general formula I.3 in which R2 is 2,2,2-trifluoroethyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0262] Table 27

[0263] Compounds of the general formula I.3 in which R2 and R6 are methyl and R5 is ethyl and R3 corresponds in each case to one line of table A.

[0264] Table 28

[0265] Compounds of the general formula I.3 in which R2 and R5 are ethyl and R6 is methyl and R3 corresponds in each case to one line of table A.

[0266] Table 29

[0267] Compounds of the general formula I.3 in which R2 and R6 are ethyl and R5 is methyl and R3 corresponds in each case to one line of table A.

[0268] Table 30

[0269] Compounds of the general formula I.3 in which R2 is methyl and R5 and R6 are ethyl and R3 corresponds in each case to one line of table A.

[0270] Table 31

[0271] Compounds of the general formula I.3 in which R2, R5 and R6 are ethyl and R3 corresponds in each case to one line of table A.

[0272] Table 32

[0273] Compounds of the general formula I.3 in which R2 is n-propyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0274] Table 33

[0275] Compounds of the general formula I.3 in which R2 and R6 are methyl and R5 is methoxymethyl and R3 corresponds in each case to one line of table A.

[0276] Table 34

[0277] Compounds of the general formula I.4 in which R2, R5 and R6 are methyl and R3 corresponds in each case to one line of table A. 39

[0278] Table 35

[0279] Compounds of the general formula I.4 in which R2 is ethyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0280] Table 36

[0281] Compounds of the general formula I.4 in which R2 is difluoromethyl and R5 and R are methyl and R3 corresponds in each case to one line of table A.

[0282] Table 37

[0283] Compounds of the general formula I.4 in which R2 is 2,2,2-trifluoroethyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0284] Table 38

[0285] Compounds of the general formula I.4 in which R2 and R6 are methyl and R5 is ethyl and R3 corresponds in each case to one line of table A.

[0286] Table 39

[0287] Compounds of the general formula I.4 in which R2 and R5 are ethyl and R6 is methyl and R3 corresponds in each case to one line of table A.

[0288] Table 40

[0289] Compounds of the general formula I.4 in which R2 and R6 are ethyl and R5 is methyl and R3 corresponds in each case to one line of table A.

[0290] Table 41

[0291] Compounds of the general formula I.4 in which R2 is methyl and R5 and R6 are ethyl and R3 corresponds in each case to one line of table A.

[0292] Table 42

[0293] Compounds of the general formula I.4 in which R2, R5 and R6 are ethyl and R3 corresponds in each case to one line of table A.

[0294] Table 43

[0295] Compounds of the general formula I.4 in which R2 is n-propyl and R5 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0296] Table 44

[0297] Compounds of the general formula I.4 in which R2 and R6 are methyl and R5 is methoxymethyl and R3 corresponds in each case to one line of table A.

[0298] Table 45

[0299] Compounds of the general formula I.5 in which R1, R2 and R6 are methyl and R3 corresponds in each case to one line of table A. 40

[0300] Table 46

[0301] Compounds of the general formula I.5 in which R1 is ethyl and R2 and R6 are methyl and; R3 corresponds in each case to one line of table A.

[0302] Table 47

[0303] Compounds of the general formula I.5 in which R1 and R2 are methyl and R6 is ethyl and R3 corresponds in each case to one line of table A.

[0304] Table 48

[0305] Compounds of the general formula I.5 in which R1 and R2 are ethyl and R6 is methyl and R3 corresponds in each case to one line of table A.

[0306] Table 49

[0307] Compounds of the general formula I.5 in which R1 and R6 are ethyl and R2 is methyl and R3 corresponds in each case to one line of table A.

[0308] Table 50

[0309] Compounds of the general formula I.5 in which R1 is methyl and R2 and R6 are ethyl and R3 corresponds in each case to one line of table A.

[0310] Table 51

[0311] Compounds of the general formula I.5 in which R1, R2 and R6 are ethyl and R3 corresponds in each case to one line of table A.

[0312] Table 52

[0313] Compounds of the general formula I.5 in which R2 is n-propyl and R1 and R6 are methyl and R3 corresponds in each, case to one line of table A.

[0314] Table 53

[0315] Compounds of the general, formula I.5 in which R2 is n-propyl, R1 is ethyl and R6 is methyl and R3 corresponds in each case to one line of table A.

[0316] Table 54

[0317] Compounds of the general formula I.6 in which R1, R2 and R6 are methyl and R3 corresponds in each case to one line of table A. 41

[0318] Table 55

[0319] Compounds of the general formula I.6 in which R1 is ethyl and R2 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0320] Table 56

[0321] Compounds of the general formula I.6 in which R1 and R2 are methyl and R6 is ethyl and R3 corresponds in each case to one line of table A.

[0322] Table 57

[0323] Compounds of the general formula I.6 in which R1 and R2 are ethyl and 6 is methyl and R3 corresponds in each case to one line of table A.

[0324] Table 58

[0325] Compounds of the general formula I.6 in which R1 and R6, are ethyl and R2 is methyl and R3 corresponds in each case to one line of table A.

[0326] Table 59

[0327] Compounds of the general formula I.6 in which R1 is methyl and R2 and R6 are ethyl and R3 corresponds in each case to one line of table A.

[0328] Table 60

[0329] Compounds of the general formula I.6 in which R1, R2 and R6 are ethyl and R3 corresponds in each case to one line of table A.

[0330] Table 61

[0331] Compounds of the general formula I.6 in which R2 is n-propyl and R1 and R6 are methyl and R3 corresponds in each case to one line of table A.

[0332] Table 62

[0333] Compounds of the general formula I.6 in which R2 is n-propyl, R1 is ethyl and R6 is methyl and R3 corresponds in each case to one line of table A.

TABLE A
No. R3
1   CH3
2   CH2CH3
3   (CH2)2CH3
4   (CH2)3CH3
5   (CH2)4CH3
6   (CH2)5CH3
7   CH(CH3)2
8   C(CH3)3
9   CH2CH(CH3)2
10  CH(CH3)CH2CH3
11  OCH3
12  OCH2CH3
13  O(CH2)2CH3
14  O(CH2)3CH3
15  O(CH2)4CH3
16  OCH(CH3)2
17  OCH(CH3)CH2CH3
18  OC(CH3)3
19  CH═CH2
20  CH═CHCH3
21  CH═C(CH3)2
22  CH2CH═CH2
23  CH2CH═CHCH3
24  OCH2CH═CH2
25  C≡CH
26  C≡CCH3
27  C≡CC(CH3)3
28  CH2C≡CH
29  CH2C≡CCH3
30  OCH2C≡CH3
31  OCH2C≡C—C(CH3)3
32  C(O)OCH3
33  C(O)OCH2CH3
34  C(O)O(CH2)2CH3
35  C(O)O(CH2)3CH3
36  C(O)O(CH2)4CH3
37  C(O)OCH(CH3)2
38  C(O)OC(CH3)3
39  CN
40  Cl
41  Br
42  CF3
43  CH2CF3
44  CH2CH2F
45  CH2CN
46  CH2OCH3
47  CH2OCH2CH3
48  (CH2)2COOCH3
49  (CH2)2CONH2
50  (CH2)2CONHCH3
51  (CH2)2CON(CH3)2
52  (CH2)2SCH3
53  CH2OCH2CH═CH2
54  42
55  43
56  CH═CF2
57  C≡C—Br
58  C≡C—OCH3
59  C3H5-cyclo
60  C4H7-cyclo
61  C5H9-cyclo
62  C6H11-cyclo
63  C6H5
64  44
65  45
66  2-F—C6H4
67  3-F—C6H4
68  4-F—C6H4
69  2,3-F2—C6H3
70  2,4-F2—C6H3
71  2,5-F2—C6H3
72  2,6-F2—C6H3
73  3,4-F2—C6H3
74  3,5-F2—C6H3
75  2-Cl—C6H4
76  3-Cl—C6H4
77  4-Cl—C6H4
78  2,3-Cl2—C6H3
79  2,4-Cl2—C6H3
80  2,5-Cl2—C6H3
81  2,6-Cl2—C6H3
82  3,4-Cl2—C6H3
83  3,5-Cl2—C6H3
84  2,3,4-Cl3—C6H2
85  2,3,5-Cl3—C6H2
86  2,3,6-Cl3—C6H2
87  2,4,5-Cl3—C6H2
88  2,4,6-Cl3—C6H2
89  3,4,5-Cl3—C6H2
90  2-Br—C6H4
91  3-Br—C6H4
92  4-Br—C6H4
93  2,3-Br2—C6H3
94  2,4-Br2—C6H3
95  2,5-Br2—C6H3
96  2,6-Br2—C6H3
97  3,4-Br2—C6H3
98  3,5-Br2—C6H3
99  2-F-3-Cl—C6H3
100 2-F-4-Cl—C6H3
101 2-F-5-Cl—C6H3
102 2-F-3-Br—C6H3
103 2-F-4-Br—C6H3
104 2-F-5-Br—C6H3
105 2-Cl-3-Br—C6H3
106 2-Cl-3-Br—C6H3
107 2-Cl-5-Br—C6H3
108 3-F-4-Cl—C6H3
109 3-F-5-Cl—C6H3
110 3-F-6-Cl—C6H3
111 3-F-4-Br—C6H3
112 3-F-5-Br—C6H3
113 3-F-6-Br—C6H3
114 3-Cl-4-Br—C6H3
115 3-Cl-5-Br—C6H3
116 3-Cl-6-Br—C6H3
117 4-F-5-Cl—C6H3
118 4-F-6-Cl—C6H3
119 4-F-5-Br—C6H3
120 4-F-6-Br—C6H3
121 4-Cl-5-Br—C6H3
122 5-F-6-Cl—C6H3
123 5-F-6-Br—C6H3
124 5-Cl-6-Br—C6H3
125 3-Br-4-Cl-5-Br—C6H2
126 2-CN—C6H4
127 3-CN—C6H4
128 4-CN—C6H4
129 3-OCN—C6H4
130 4-OCN—C6H4
131 2-CH3O—C6H4
132 3-CH3O—C6H4
133 4-CH3O—C6H4
134 2,3-(CH3O)2—C6H3
135 2,4-(CH3O)2—C6H3
136 2,5-(CH3O)2—C6H3
137 3,4-(CH3O)2—C6H3
138 3,5-(CH3O)2—C6H3
139 3,4,5-(CH3O)3—C6H2
140 2-C2H5O—C6H4
141 3-C2H5O—C6H4
142 4-C2H5O—C6H4
143 2-(n-C3H7O)—C6H4
144 3-(n-C3H7O)—C6H4
145 4-(n-C3H7O)—C6H4
146 2-(i-C3H7O)—C6H4
147 3-(i-C3H7O)—C6H4
148 4-(i-C3H7O)—C6H4
149 4-(n-C4H9O)—C6H4
150 3-(t-C4H9O)—C6H4
151 4-(t-C4H9O)—C6H4
152 2-(CH2═CH—CH2)—O—C6H4
153 3-(CH2═CH—CH2)—O—C6H4
154 4-(CH2═CH—CH2)—O—C6H4
155 2-CF3—C6H4
156 3-CF3—C6H4
157 4-CF3—C6H4
158 2-(CH3—CO)—C6H4
159 3-(CH3—CO)—C6H4
160 4-(CH3—CO)—C6H4
161 2-(CH3—O—CO)—C6H4
162 3-(CH3—O—CO)—C6H4
163 4-(CH3—O—CO)—C6H4
164 2-(H2N—CO)—C6H4
165 3-(H2N—CO)—C6H4
166 4-(H2N—CO)—C6H4
167 2-[(CH3)2N—CO]—C6H4
168 3-[(CH3)2N—CO]—C6H4
169 4-[(CH3)2N—CO]—C6H4
170 2-(CH3—NH—CO)—C6H4
171 3-(CH3—NH—CO)—C6H4
172 4-(CH3—NH—CO)—C6H4
173 2-CH3S—C6H4
174 3-CH3S—C6H4
175 4-CH3S—C6H4
176 2-CH3SO2—C6H4
177 3-CH3SO2—C6H4
178 4-CH3SO2—C6H4
179 2-CF3O—C6H4
180 3-CF3O—C6H4
181 4-CF3O—C6H4
182 2-CHF2O—C6H4
183 3-CHF2O—C6H4
184 4-CHF2O—C6H4
185 3-CF3-4-CF3O—C6H3
186 2-CH3NH—C6H4
187 3-CH3NH—C6H4
188 4-CH3NH—C6H4
189 2-(CH3)2N—C6H4
190 3-(CH3)2N—C6H4
191 4-(CH3)2N—C6H4
192 2-(C2H5—O—CO)—C6H4
193 3-(C2H5—O—CO)—C6H4
194 4-(C2H5—O—CO)—C6H4
195 2-CH2FCH2—C6H4
196 3-CH2FCH2—C6H4
197 4-CH2FCH2—C6H4
198 2-CF3CH2—C6H4
199 3-CF3CH2—C6H4
200 4-CF3CH2—C6H4
201 2-CHF2CF2—C6H4
202 3-CHF2CF2—C6H4
203 4-CHF2CF2—C6H4
204 2-CHF2—C6H4
205 3-CHF2—C6H4
206 4-CHF2—C6H4
207 2-NO2—C6H4
208 3-NO2—C6H4
209 4-NO2—C6H4
210 2-CH3—C6H4
211 3-CH3—C6H4
212 4-CH3—C6H4
213 2,3-(CH3)2—C6H3
214 2,4-(CH3)2—C6H3
215 2,5-(CH3)2—C6H3
216 2,6-(CH3)2—C6H3
217 3,4-(CH3)2—C6H3
218 3,5-(CH3)2—C6H3
219 2-C2H5—C6H4
220 3-C2H5—C6H4
221 4-C2H5—C6H4
222 2-i-C3H7—C6H4
223 3-i-C3H7—C6H4
224 4-i-C3H7—C6H4
225 3-t-C4H9—C6H4
226 4-t-C4H9—C6H4
227 2-(CH2═CH)—C6H4
228 3-(CH2═CH)—C6H4
229 4-(CH2═CH)—C6H4
230 2-(CH2═CH—CH2)C6H4
231 3-(CH2═CH—CH2)—C6H4
232 4-(CH2═CH—CH2)—C6H4
233 2-(CH≡C—CH2)—C6H4
234 2-(CH≡C)—C6H4
235 3-(CH≡C—CH2)—O—C6H4
236 4-(CH≡C—CH2CH2)—O—C6H4
237 2-C6H5—C6H4
238 3-C6H5—C6H4
239 3-CH3-5-t-C4H9—C6H3
240 2-F-4-CH3—C6H3
241 2-F-5-CH3—C6H3
242 2-CH3-4-F—C6H3
243 2-CH3-5-F—C6H3
244 2-CH3-4-Cl—C6H3
245 2-F-4-CH3—O—C6H3
246 2-F-4-CH3CH2O—C6H3
247 2-F-4-i-C3H7—C6H3
248 46
249 47
250 48
251 49
252 50
253 51
254 52
255 53
256 54
257 55
258 56
259 57
260 58
261 59
262 60
263 61
264 62
265 63
266 64
267 65
268 66
269 67
270 68
271 69
272 70
273 71
274 72
275 73
276 74
277 75
278 76
279 77
280 78
281 79
282 80
283 81
284 82
285 83
286 84
287 85
288 86
289 87
290 88
291 89
292 90
293 91
294 92
295 93
296 94
297 95
298 96
299 97
300 98
301 99
302 100
303 101
304 1-Methylprop-2-yl
305 1-Methylprop-3-yl
306 102
307 103
308 104
309 105
310 106
311 107
312 108
313 109
314 110
315 111
316 112
317 113
318 114
319 115
320 116
321 117
322 118
323 119
324 120
325 121
326 122
327 123
328 124
329 125
330 126
331 127
332 128
333 129
334 130
335 131
336 132
337 133
338 134
339 135
340 136
341 137
342 138
343 139
344 140
345 141
346 142
347 143
348 144
349 145
350 146
351 147
352 148
353 149
354 150
355 151
356 152
357 153
358 154
359 155
360 156
361 157
362 158
363 159
364 160
365 161
366 162
367 163
368 164
369 165
370 166
371 167
372 168
373 169
374 170
375 171
376 172
377 173
378 174
379 175
380 176
381 177
382 178
383 179
384 180
385 181
386 182
387 183
388 184
389 185
390 186
391 187
392 188
393 189
394 190
395 191
396 192
397 193
398 194
399 195
400 196
401 197
402 198
403 199
404 200
405 201
406 202
407 203
408 204
409 205
410 206
411 207
412 208
413 209
414 210
415 211
416 212
417 213
418 214
419 215
420 216
421 217
422 218
423 219
424 220
425 221
426 222
427 223
428 224
429 225
430 C3H5-cycl-O—
431 C4H7-cycl-O—
432 C5H9-cycl-O—
433 C6H11-cycl-O—
434 C6H5-O—
435 226
436 227
437 2-F—C6H4O
438 3-F—C6H4O
439 4-F—C6H4O
440 2,3-F2—C6H3O
441 2,4-F2—C6H3O
442 2,5-F2—C6H3O
443 2,6-F2—C6H3O
444 3,4-F2—C6H3O
445 3,5-F2—C6H3O
446 2-Cl—C6H4O
447 3-Cl—C6H4O
448 4-Cl—C6H4O
449 2,3-Cl2—C6H3O
450 2,4-Cl2—C6H3O
451 2,5-Cl2—C6H3O
452 2,6-Cl2—C6H3O
453 3,4-Cl2—C6H3O
454 3,5-Cl2—C6H3O
455 2,3,4-Cl3—C6H2O
456 2,3,5-Cl3—C6H2O
457 2,3,6-Cl3—C6H2O
458 2,4,5-Cl3—C6H2O
459 2,4,6-Cl3—C6H2O
460 3,4,5-Cl3—C6H2O
461 2-Br—C6H4O
462 3-Br—C6H4O
463 4-Br—C6H4O
464 2,3-Br2—C6H3O
465 2,4-Br2—C6H3O
466 2,5-Br2—C6H3O
467 2,6-Br2—C6H3O
468 3,4-Br2—C6H3O
469 3,5-Br2—C6H3O
470 2-F-3-Cl—C6H3O
471 2-F-4-Cl—C6H3O
472 2-F-5-Cl—C6H3O
473 2-F-3-Br—C6H3O
474 2-F-4-Br—C6H3O
475 2-F-5-Br—C6H3O
476 2-Cl-3-Br—C6H3O
477 2-Cl-4-Br—C6H3O
478 2-Cl-5-Br—C6H3O
479 3-F-4-Cl—C6H3O
480 3-F-5-Cl—C6H3O
481 3-F-6-Cl—C6H3O
482 3-F-4-Br—C6H3O
483 3-F-5-Br—C6H3O
484 3-F-6-Br—C6H3O
485 3-Cl-4-Br—C6H3O
486 3-Cl-5-Br—C6H3O
487 3-Cl-6-Br—C6H3O
488 4-F-5-Cl—C6H3O
489 4-F-6-Cl—C6H3O
490 4-F-5-Br—C6H3O
491 4-F-6-Br—C6H3O
492 4-Cl-5-Br—C6H3O
493 5-F-6-Cl—C6H3O
494 5-F-6-Br—C6H3O
495 5-Cl-6-Br—C6H3O
496 3-Br-4-Cl-5-Br—C6H2O
497 2-CN—C6H4O
498 3-CN—C6H4O
499 4-CN—C6H4O
500 4-[(CH3)2N—CO]—C6H4O
501 2-(CH3—NH—CO)—C6H4O
502 3-(CH3—NH—CO)—C6H4O
503 4-(CH3—NH—CO)—C6H4O
504 2-CH3S—C6H4O
505 3-CH3S—C6H4O
506 4-CH3S—C6H4O
507 2-CH3SO2—C6H4O
508 3-CH3SO2—C6H4O
509 4-CH3SO2—C6H4O
510 2-CF3O—C6H4O
511 3-CF3O—C6H4O
512 4-CF3O—C6H4O
513 2-CHF2O—C6H4O
514 4-CHF2O—C6H4O
515 4-CHF2O—C6H4O
516 3-CF3-4-CF3O—C6H3O
517 2-CH3NH—C6H4O
518 3-CH3NH—C6H4O
519 4-CH3NH—C6H4O
520 2-(CH3)2N—C6H4O
521 3-(CH3)2N—C6H4O
522 4-(CH3)2N—C6H4O
523 2-(C2H5—O—CO)—C6H4O
524 3-(C2H5—O—CO)—C6H4O
525 4-(C2H5—O—CO)—C6H4O
526 2-CH2FCH2—C6H4O
527 3-CH2FCH2—C6H4O
528 4-CH2FCH2—C6H4O
529 2-CF3CH2—C6H4O
530 3-CF3CH2—C6H4O
531 4-CF3CH2—C6H4O
532 2-CHF2CF2—C6H4O
533 3-CHF2CF2—C6H4O
534 4-CHF2CF2—C6H4O
535 2-CHF2—C6H4O
536 3-CHF2—C6H4O
537 4-CHF2—C6H4O
538 2-CH3O—C6H4O
539 3-CH3O—C6H4O
540 4-CH3O—C6H4O
541 2,3-(CH3O)2—C6H3O
542 2,4-(CH3O)2—C6H3O
543 2,5-(CH3O)2—C6H3O
544 3,4-(CH3O)2—C6H3O
545 3,5-(CH3O)2—C6H3O
546 3,4,5-(CH3O)3—C6H2O
547 2-C2H5O—C6H4O
548 3-C2H5O—C6H4O
549 4-C2H5O—C6H4O
550 2-(n-C3H7O)—C6H4O
551 3-(n-C3H7O)—C6H4O
552 4-(n-C3H7O)—C6H4O
553 2-(i-C3H7O)—C6H4O
554 3-(i-C3H7O)—C6H4O
555 4-(i-C3H7O)—C6H4O
556 4-(n-C4H9O)—C6H4O
557 3-(t-C4H9O)—C6H4O
558 4-(t-C4H9O)—C6H4O
559 2-(CH═CH—CH2—O)—C6H4O
560 3-(CH═CH—CH2—O)—C6H4O
561 4-(CH═CH—CH2—O)—C6H4O
562 2-CF3—C6H4O
563 3-CF3—C6H4O
564 4-CF3—C6H4O
565 2-(CH3—CO)—C6H4O
566 3-(CH3—CO)—C6H4O
567 4-(CH3—CO)—C6H4O
568 2-(CH3—O—CO)—C6H4O
569 3-(CH3—O—CO)—C6H4O
570 4-(CH3—O—CO)—C6H4O
571 2-(H2N—CO)—C6H4O
572 3-(H2N—CO)—C6H4O
573 4-(H2N—CO)—C6H4O
574 2-[(CH3)2N—CO]—C6H4O
575 3-[(CH3)2N—CO]—C6H4O
576 2-NO2—C6H4O
577 3-NO2—C6H4O
578 4-NO2—C6H4O
579 2-CH3—C6H4O
580 3-CH3—C6H4O
581 4-CH3—C6H4O
582 2,3-(CH3)2—C6H3O
583 2,4-(CH3)2—C6H3O
584 2,5-(CH3)2—C6H3O
585 2,6-(CH3)2—C6H3O
586 3,4-(CH3)2—C6H3O
587 3,5-(CH3)2—C6H3O
588 2-C2H5—C4H4O
589 3-C2H5—C6H4O
590 4-C2H5—C6H4O
591 2-i-C3H7—C6H4O
592 3-i-C3H7—C6H4O
593 4-i-C3H7—C6H4O
594 3-t-C4H9—C6H4O
595 4-t-C4H9—C6H4O
596 2-H2C═CH—C6H4O
597 3-H2C═CH—C6H4O
598 4-H2C═CH—C6H4O
599 2-(H2C═CH—CH2)—C6H4O
600 3-(H2C═CH—CH2)—C6H4O
601 4-(H2C═CH—CH2)—C6H4O
602 2-C6H5—C6H4O
603 3-C6H5—C6H4O
604 4-C6H5—C6H4O
605 3-CH3-5-t-C4H9—C6H3O
606 2-F-4-CH3—C6H3O
607 2-F-5-CH3—C6H3O
608 2-CH3-4-F—C6H3O
609 2-CH3-5-F—C6H3O
610 2-CH3-4-Cl—C6H3O
611 228
612 229
613 230
614 231
615 232
616 233
617 234
618 235

[0334] Table 63

[0335] Compounds of the general formula I.7 in which R1, R2 and R5 are methyl, Q is O and Z corresponds in each case to one line of table B. 236

[0336] Table 64

[0337] Compounds of the general formula I.7 in which R1, R2 and R5 are methyl, Q is OCH2 and Z corresponds in each case to one line of table B.>

[0338] Table 65

[0339] Compounds of the general formula I.7 in which R1, R2 and R5 are methyl, Q is CH2O and Z corresponds in each case to one line of table B.

[0340] Table 66

[0341] Compounds of the general formula I.7 in which R1, R2 and R5 are methyl, Q is S and Z corresponds in each case to one line of table B.

[0342] Table 67

[0343] Compounds of the general formula I.7 in which R1, R2 and R5 are methyl, Q is —C≡C— and Z corresponds in each case to one line of table B.

[0344] Table 68

[0345] Compounds of the general formula I.7 in which R1, R2 and R5 are methyl, Q is —CH═CH— and Z corresponds in each case to one line of table B.

[0346] Table 69

[0347] Compounds of the general formula I.7 in which R1, R2 and R5 are methyl, Q is —CH2—CH2— and Z corresponds in each case to one line of table B.

[0348] Table 70

[0349] Compounds of the general formula I.7 in which R1, R2 and R5 are methyl, Q is a direct bond and Z corresponds in each case to one line of table B.

[0350] Table 71

[0351] Compounds of the general formula I.7 in which R1 and R5 are methyl, R2 is ethyl, Q is O and Z corresponds in each case to one line of table B.

[0352] Table 72

[0353] Compounds of the general formula I.7 in which R1 and R5 are methyl, R2 is ethyl, Q is OCH2 and Z corresponds in each case to one line of table B.

[0354] Table 73

[0355] Compounds of the general formula I.7 in which R1 and R5 are methyl, R2 is ethyl, Q is CH2O and Z corresponds in each case to one line of table B.

[0356] Table 74

[0357] Compounds of the general formula I.7 in which R1 and R5 are methyl, R2 is ethyl, Q is S and Z corresponds in each case to one line of table B.

[0358] Table 75

[0359] Compounds of the general formula I.7 in which R1 and R5 are methyl, R2 is ethyl, Q is —C≡C— and Z corresponds in each case to one line of table B.

[0360] Table 76

[0361] Compounds of the general formula I.7 in which R1 and R5 are, methyl, R2 is ethyl, Q is —CH═CH— and Z corresponds in each case to one line of table B.

[0362] Table 77

[0363] Compounds of the general formula I.7 in which R1 and R5 are methyl, R2 is ethyl, Q is —CH2—CH2— and Z corresponds in each case to one line of table B.

[0364] Table 78

[0365] Compounds of the general formula I.7 in which R1 and R5 are methyl, R2 is ethyl, Q is a direct bond and Z corresponds in each case to one line of table B.

[0366] Table 79

[0367] Compounds of the general formula I.7 in which R1 is ethyl, R2 and R5 are methyl, Q is O and Z corresponds in each case to one line of table B.

[0368] Table 80

[0369] Compounds of the general formula I.7 in which R1 is ethyl, R2 and R5 are methyl, Q is OCH2 and Z corresponds in each case to one line of table B.

[0370] Table 81

[0371] Compounds of the general formula I.7 in which R1 is ethyl, R2 and R5 are methyl, Q is CH2O and Z corresponds in each case to one line of table B.

[0372] Table 82

[0373] Compounds of the general formula I.7 in which R1 is ethyl, R2 and R5 are methyl, Q is S and Z corresponds in each case to one line of table B.

[0374] Table 83

[0375] Compounds of the general formula I.7 in which R1 is ethyl, R2 and R5 are methyl, Q is —C≡C— and Z corresponds in each case to one line of table B.

[0376] Table 84

[0377] Compounds of the general formula I.7 in which R1 is ethyl, R2 and R5 are methyl, Q is —CH═CH— and Z corresponds in each case to one line of table B.

[0378] Table 85

[0379] Compounds of the general formula I.7 in which R1 is ethyl, R2 and R5 are methyl, Q is —CH2—CH2— and Z corresponds in each case to one line of table B.

[0380] Table 86

[0381] Compounds of the general formula I.7 in which R1 is ethyl, R2 and R5 are methyl, Q is a direct bond and Z corresponds in each case to one line of table B.

[0382] Table 87

[0383] Compounds of the general formula I.7 in which R1 and R2 are ethyl, R5 is methyl, Q is O and Z corresponds in each case to one line of table B.

[0384] Table 88

[0385] Compounds of the general formula I.7 in which R1 and R2 are ethyl, R5 is methyl, Q is OCH2 and Z corresponds in each case to one line of table B.

[0386] Table 89

[0387] Compounds of the general formula I.7 in which R1 and R2 are ethyl, R5 is methyl, Q is CH2O and Z corresponds in each case to one line of table B.

[0388] Table 90

[0389] Compounds of the general formula I.7 in which R1 and R2 are ethyl, R5 is methyl, Q is S and Z corresponds in each case to one line of table B.

[0390] Table 91

[0391] Compounds of the general formula I.7 in which R1 and R2 are ethyl, R5 is methyl, Q is —C≡C— and Z corresponds in each case to one line of table B.

[0392] Table 92

[0393] Compounds of the general formula I.7 in which R1 and R2 are ethyl, R5 is methyl, Q is —CH═CH— and Z corresponds in each case to one line of table B.

[0394] Table 93

[0395] Compounds of the general formula I.7 in which R1 and R2 are ethyl, R5 is methyl, Q is —CH2—CH2— and Z corresponds in each case to one line of table B.

[0396] Table 94

[0397] Compounds of the general formula I.7 in which R1 and R2 are-ethyl, R5 is methyl, Q is a direct bond: and Z corresponds in each case to one line of table B.

[0398] Table 95

[0399] Compounds of the general formula I.7 in which R1 and R5 are methyl, R2 is propargyl, Q is O and Z corresponds in each case to one line of table B.

[0400] Table 96

[0401] Compounds of the general formula I.7 in which R1 is ethyl, R5 is methyl and R2 is propargyl, Q is O and Z corresponds in each case to one line of table B.

[0402] Table 97

[0403] Compounds of the general formula I.7 in which R1 and R5 are methyl, R2 is allyl, Q is O and Z corresponds in each case to one line of table B.

[0404] Table 98

[0405] Compounds of the general formula I.7 in which R1 is ethyl, R5 is methyl, R2 is allyl, Q is O and Z corresponds in each case to one line of table B.

[0406] Table 99

[0407] Compounds of the general formula I.7 in which R1 and R5 are methyl, R2 is n-propyl, Q is O and Z corresponds in each case to one line of table B.

[0408] Table 100

[0409] Compounds of the general formula I.7 in which R1 is ethyl, R5 is methyl-, R2 is n-propyl, Q is O and Z corresponds in each case to one line of table B.

[0410] Table 101

[0411] Compounds of the general formula I.7 in which R1 and R5 are methyl, R2 is i-propyl, Q is O and Z corresponds in each case to one line of table B.

[0412] Table 102

[0413] Compounds of the general formula I.7 in which R1 is ethyl, R5 is methyl, R2 is i-propyl, Q is O and Z corresponds in each case to one line of table B.

[0414] Table 103

[0415] Compounds of the general formula I.7 in which R1 and R2 are methyl, R5 is ethyl, Q is O and Z corresponds in each case to one line of table B.

[0416] Table 104

[0417] Compounds of the general formula I.7 in which R1 and R2 are methyl, R5 is allyl, Q is O and Z corresponds in each case to one line of table B.

[0418] Table 105

[0419] Compounds of the general formula I.7 in which R1 and R2 are methyl, R5 is propargyl, Q is O and Z corresponds in each case to one line of table B.

[0420] Table 106

[0421] Compounds of the general formula I.7 in which R1 and R2 are methyl, R5 is methoxymethyl, Q is O and Z corresponds in each case to one line of table B.

[0422] Table 107

[0423] Compounds of the general formula I.7 in which R1 is methyl, R2 and R5 are ethyl, Q is O and Z corresponds in each case to one line of table B.

[0424] Table 108

[0425] Compounds of the general formula I.7 in which R2 is methyl, R1 and R5 are ethyl, Q is O and Z corresponds in each case to one line of table B.

[0426] Table 109

[0427] Compounds of the general formula I.7 in which R1, R2 and R5 are ethyl, Q is O and Z corresponds in each case to one line of table B.

[0428] Table 110

[0429] Compounds of the general formula I.7 in which R1 is methyl, R2 is ethyl, R5 is propargyl, Q is O and Z corresponds in each case to one line of table B.

[0430] Table 111

[0431] Compounds of the general formula I.7 in which R1 and R2 are ethyl, R5 is propargyl, Q is O and Z corresponds in each case to one line of table B.

[0432] Table 112

[0433] Compounds of the general formula I.7 in which R1 is methyl, R2 is ethyl, R5 is methoxymethyl, Q is O and Z corresponds in each case to one line of table B.

[0434] Table 113

[0435] Compounds of the general formula I.7 in which R1 and R2 is ethyl, R5 is methoxymethyl, Q is O and Z corresponds in each case to one line of table B.

[0436] Table 114

[0437] Compounds of the general formula I.8 in which R1, R2 and R5 are methyl, Q is O and Z corresponds in each case to one line of table B. 237

[0438] Compounds of the general formula I.8 in which R1, R2 and R5 are methyl, Q is OCH2 and Z corresponds in each case to one line of table B.

[0439] Table 116

[0440] Compounds of the general formula I.8 in which R1, R2— and R5 are methyl, Q is CH2O and Z corresponds in each case to one line of table B.

[0441] Table 117

[0442] Compounds of the general formula I.8 in which R1, R2 and R5 are methyl, Q is S and Z corresponds in each case to one line of table B.

[0443] Table 118

[0444] Compounds of the general formula I.8 in which R1, R2 and R5 are methyl, Q is —C≡C— and Z corresponds in each case to one line of table B.

[0445] Table 119

[0446] Compounds of the general formula I.8 in which R1, R2 and R5 are methyl, Q is —CH═CH— and Z corresponds in each case to one line of table B.

[0447] Table 120

[0448] Compounds of the general formula I.8 in which R1, R2 and R5 are methyl, Q is —CH2—CH2— and Z corresponds in each case to one line of table B.

[0449] Table 121

[0450] Compounds of the general formula I.8 in which R1, R2 and R5 are methyl, Q is a direct bond and Z corresponds in each case to one line of table B.

[0451] Table 122

[0452] Compounds of the general formula I.8 in which R1 and R5 are methyl, R2 is ethyl, Q is O and Z corresponds in each case to one line of table B.

[0453] Table 123

[0454] Compounds of the general formula I.8 in which R1 and R5 are methyl, R2 is ethyl, Q is OCH2 and Z corresponds in each case to one line of table B.

[0455] Table 124

[0456] Compounds of the general formula I.8 in which R1 and R5 are methyl, R2 is ethyl, Q is CH2O and Z corresponds in each case to one line of table B.

[0457] Table 125

[0458] Compounds of the general formula I.8 in which R1 and R5 are methyl, R2 is ethyl, Q is S and Z corresponds in each case to one line of table B.

[0459] Table 126

[0460] Compounds of the general formula I.8 in which R1 and R5 are methyl, R2 is ethyl, Q is —C≡C— and Z corresponds in each case to one line of table B.

[0461] Table 127

[0462] Compounds of the general formula I.8 in which R1 and R5 are methyl, R2 is ethyl, Q is —CH═CH— and Z corresponds in each case to one line of table B.

[0463] Table 128

[0464] Compounds of the general formula I.8 in which R1 and R5 are methyl, R2 is ethyl, Q is —CH2—CH2— and Z corresponds in each case to one line of table B.

[0465] Table 129

[0466] Compounds of the general formula I.8 in which R1 and R5 are methyl, R2 is ethyl, Q is a direct bond and Z corresponds in each case to one line of table B.

[0467] Table 130

[0468] Compounds of the general formula I.8 in which R1 is ethyl, R2 and R5 are methyl, Q is O and Z corresponds in each case to one line of table B.

[0469] Table 131

[0470] Compounds of the general formula I.8 in which R1 is ethyl, R2 and R5 are methyl, Q is OCH2 and Z corresponds in each case to one line of table B.

[0471] Table 132

[0472] Compounds of the general formula I.8 in which R1 is ethyl, R2 and R5 are methyl, Q is CH2O and Z corresponds in each case to one line of table B.

[0473] Table 133

[0474] Compounds of the general formula I.8 in which R1 is ethyl, R2 and R5 are methyl, Q is S and Z corresponds in each case to one line of table B.

[0475] Table 134

[0476] Compounds of the general formula I.8 in which R1 is ethyl, R2 and R5 are methyl, Q is —C≡C— and Z corresponds in each case to one line of table B.

[0477] Table 135

[0478] Compounds of the general formula I.8 in which R1 is ethyl, R2 and R5 are methyl, Q is —CH═CH— and Z corresponds in each case to one line of table B.

[0479] Table 136

[0480] Compounds of the general formula I.8 in which R1 is ethyl, R2 and R5 are methyl, Q is —CH2—CH2— and Z corresponds in each case to one line of table B.

[0481] Table 137

[0482] Compounds of the general formula I.8 in which R1 is ethyl, R2 and R5 are methyl, Q is a direct bond and Z corresponds in each case to one line of table B.

[0483] Table 138

[0484] Compounds of the general formula I.8 in which R1 and R2 are ethyl, R5 is methyl, Q is O and Z corresponds in each case to one line of table B.

[0485] Table 139

[0486] Compounds of the general formula I.8 in which R1 and R2 are ethyl, R5 is methyl, Q is OCH2 and Z corresponds in each case to one line of table B.

[0487] Table 140

[0488] Compounds of the general formula I.8 in which R1 and R2 are ethyl, R5 is methyl, Q is CH2O and Z corresponds in each case to one line of table B.

[0489] Table 141

[0490] Compounds of the general formula I.8 in which R1 and R2 are ethyl, R5 is methyl, Q is S and Z corresponds in each case to one line of table B.

[0491] Table 142

[0492] Compounds of the general formula I.8 in which R1 and R2 are ethyl, R5 is methyl, Q is —C≡C— and Z corresponds in each case to one line of table B.

[0493] Table 143

[0494] Compounds of the general formula I.8 in which R1 and R2 are ethyl, R5 is methyl, Q is —CH═CH— and Z corresponds in each case to one line of table B.

[0495] Table 144

[0496] Compounds of the general formula I.8 in which R1 and R2 are ethyl, R5 is methyl, Q is —CH2—CH2— and Z corresponds in each case to one line of table B.

[0497] Table 145

[0498] Compounds of the general formula I.8 in which R1 and R2 are ethyl, R5 is methyl, Q is a direct bond and Z corresponds in each case to one line of table B.

[0499] Table 146

[0500] Compounds of the general formula I.8 in which R1 and R5 are methyl, R2 is propargyl, Q is O and Z corresponds in each case to one line of table B.

[0501] Table 147

[0502] Compounds of the general formula I.8 in which R1 is ethyl, R5 is methyl and R2 is propargyl, Q is O and Z corresponds in each case to one line of table B.

[0503] Table 148

[0504] Compounds of the general formula I.8 in which R1 and R5 are methyl, R2 is allyl, Q is O and Z corresponds in each case to one line of table B.

[0505] Table 149

[0506] Compounds of the general formula I.8 in which R1 is ethyl, R5 is methyl, R2 is allyl, Q is O and Z corresponds in each case to one line of table B.

[0507] Table 150

[0508] Compounds of the general formula I.8 in which R1 and R5 are methyl, R2 is n-propyl, Q is O and Z corresponds in each case to one line of table B.

[0509] Table 151

[0510] Compounds of the general formula I.8 in which R1 is ethyl, R5 is methyl, R2 is n-propyl, Q is O and Z corresponds in each case to one line of table B.

[0511] Table 152

[0512] Compounds of the general formula I.8 in which R1 and R5 are methyl, R2 is i-propyl, Q is O and Z corresponds in each case to one line of table B.

[0513] Table 153

[0514] Compounds of the general formula I.8 in which R1 is ethyl, R5 is methyl, R2 is i-propyl, Q is O and Z corresponds in each case to one line of table B.

[0515] Table 154

[0516] Compounds of the general formula I.8 in which R1 and R2 are methyl, R5 is ethyl, Q is O and Z corresponds in each case to one line of table B.

[0517] Table 155

[0518] Compounds of the general formula I.8 in which R1 and R2 are methyl, R5 is allyl, Q is O and Z corresponds in each case to one line of table B.

[0519] Table 156

[0520] Compounds of the general formula I.8 in which R1 and R2 are methyl, R5 is propargyl, Q is O and Z corresponds in each case to one line of table B.

[0521] Table 157

[0522] Compounds of the general formula I.8 in which R1 and R2 are methyl, R5 is methoxymethyl, Q is O and Z corresponds in each case to one line of table B.

[0523] Table 158

[0524] Compounds of the general formula I.8 in which R1 is methyl, R2 and R5 are ethyl, Q is O and Z corresponds in each case to one line of table B.

[0525] Table 159

[0526] Compounds of the general formula I.8 in which R2 is methyl, R1 and R5 are ethyl, Q is O and Z corresponds in each case to one line of table B.

[0527] Table 160

[0528] Compounds of the general formula I.8 in which R1, R2 and R5 are ethyl, Q is O and Z corresponds in each case to one line of table B.

[0529] Table 161

[0530] Compounds of the general formula I.8 in which R1 is methyl, R2 is ethyl, R5 is propargyl, Q is O and Z corresponds in each case to one line of table B.

[0531] Table 162

[0532] Compounds of the general formula I.8 in which R1 and R2 are ethyl, R5 is propargyl, Q is O and Z corresponds in each case to one line of table B.

[0533] Table 163

[0534] Compounds of the general formula I.8 in which R1 is methyl, R2 is ethyl, R5 is methoxymethyl, Q is O and Z corresponds in each case to one line of table B.

[0535] Table 164

[0536] Compounds of the general formula I.8 in which R1 and R2 are ethyl, R5 is methoxymethyl, Q is O and Z corresponds in each case to one line of table B.

TABLE B
No. Z
1   2-F
2   3-F
3   4-F
4   2-Cl
5   3-Cl
6   4-Cl
7   2-Br
8   3-Br
9   4-Br
10  2-CH3
11  3-CH3
12  4-CH3
13  2-CH2CH3
14  3-CH2CH3
15  4-CH2CH3
16  4-CH(CH3)2
17  4-C(CH3)3
18  2-CF3
19  3-CF3
20  4-CF3
21  2-OCF3
22  3-OCF3
23  4-OCF3
24  4-SCF3
25  4-S(═O)CF3
26  4-S(═O)2CF3
27  4-CN
28  2,3-Cl2
29  2,4-Cl2
30  2,5-Cl2
31  2,6-Cl2
32  3,4-Cl2
33  3,5-Cl2
34  3-Cl,4-CF3
35  4-Cl,3-CF3
36  3-F,4-CF3
37  4-F,3-CF3
38  3,4-(—OCH2—O—)
39  3,4-(—OCF2—O—)
40  3,4-(—OCF2CF2—O)
41  3,5-(CF3)2

[0537] Formulations may be prepared in analogy to those described in, for example, WO 97/33890.

BIOLOGICAL EXAMPLES

[0538] A. Fungicidal Activities

Example B-1

Activity Against Puccinia graminis in Wheat

[0539] 6 days after sowing, wheat plants are sprayed to runoff with an aqueous spray liquor (0.02% active substance) prepared from a wettable powder of the active substance and 24 hours later are infected with a uredospore suspension of the fungus. After an incubation time of 48 hours (conditions: 95 to 100% relative humidity at, 20° C.), the plants are placed in a greenhouse at 22° C. Fungal infestation is assessed 12 days after infection.

[0540] Compounds 1, 2 and 10 to 13 from table A and compounds 1 and 6 to 9 from table B exhibit an activity of more than 80% in this test.

Example B-2

Activity Against Phytophthora infestans in Tomatoes

[0541] After being grown for three weeks, tomato plants are sprayed to runoff with an aqueous spray liquor (0.02% active substance) prepared from a wettable powder of the active substance and 24 hours later are infected with a sporangia suspension of the fungus. Fungal infestation is assessed 5 days after infection, during which 90 to 100% relative humidity and a temperature of 20° C. are maintained.

[0542] Compounds 1 and 10 to 13 from table A exhibit an activity of more than 80% in this test.

Example B-3

Residual Protective Activity Against Cercospora arachidicola in Peanuts

[0543] Peanut plants 10 to 15 cm high are sprayed to runoff with an aqueous spray liquor (0.02% active substance) prepared from a wettable powder of the active substance and 48 hours later are infected with a conidia suspension of the fungus. The plants are incubated at 21° C. and high atmospheric humidity for 72 hours and then placed in a greenhouse until the typical leaf spots appear. The activity of the active substance is evaluated 12 days after infection, on the basis of the number and size of leaf spots.

[0544] Compound 7:from table b exhibits an activity of more than 80% in this test.

Example B-4

Activity Against Plasmovara viticola in Vines

[0545] Vine seedlings at the 4- to 5-leaf stage are sprayed to runoff with an aqueous spray liquor (0.02% active substance) prepared from a wettable powder of the active substance and 24 hours later are infected with a sporangia suspension of the fungus. Fungal infestation is assessed 6 days after infection, during which from 95 to 100% relative humidity and a temperature of 20° C. are maintained.

[0546] Compounds 10 to 13 from table a and compounds 8 and 9 from table b exhibit an activity of more than 80% in this test.

Example B-5

Residual Protective Activity Against Venturia inaequalis in Apples

[0547] Apple seedlings with fresh shoots 10 to 20 cm long are sprayed to runoff with an aqueous spray liquor (0.02% active substance) prepared from a wettable powder of the active substance and 24 hours later are infected with a conidia suspension of the fungus. The plants are incubated at from 90 to 100 percent relative atmospheric humidity for 5 days and placed in a greenhouse at from 20 to 24° C. for 10 days more. Fungal infestation is assessed 12 days after infection.

[0548] Compounds 1 and 10 to 13 from table a and compounds 1 to 4 and 6 to 9 from table b exhibit an activity of more than 80% in this test.

Example B-6

Activity Against Erysiphe praminis in Barley

[0549] Barley plants approximately 8 cm high are sprayed to runoff with an aqueous spray liquor (0.02% active substance) prepared from a wettable powder of the active substance and 3 to 4 hours later are dusted with conidia of the fungus. The infected plants are placed in a greenhouse at 22° C. Fungal infestation is assessed 12 days after infection.

[0550] Compounds 1, 5 and 10 to 13 from table a and compounds 1, 2 and 6 to 9 from table b exhibit an activity of more than 80% in this test.

Example B-7

Activity Against Podosphaera leucotricha on Apple Shoots

[0551] Apple seedlings with fresh shoots about 15 cm long are sprayed with a spray liquor (0.006% active substance). After 24 hours, the treated plants are infected with a conidia suspension of the fungus and placed in a controlled-climate chamber at 70% relative humidity and 20° C. Fungal infestation is assessed 12 days after infection.

[0552] Compounds 10 to 13 from table a and compounds 1, 2 and 9 from table b exhibit an activity of more than 80% in this test.

[0553] B. Insecticidal Activities

Example B-8

Activity Against Aphis craccivora

[0554] Pea seedlings are infected with Aphis craccivora and sprayed with a spray liquor containing 100 ppm active substance and incubated at 20° C. 3 and 6 days later, the percentage reduction in the population (% activity) is determined by comparing the number of dead aphids on the treated and untreated plants.

[0555] Compound 5 from table a exhibits good activity in this test, i.e. a kill rate of more than 80%.

Example B-9

Activity Against Diabrotica balteata

[0556] Maize seedlings are sprayed with an aqueous emulsion spray liquor containing 400 ppm active substance and, after the spray coating is dried on, are populated with 10 second-stage larvae of Diabrotica balteata and placed in a plastic container. 6 days later, the percentage reduction in population (% activity) is determined by comparing the number of dead larvae between the treated and the untreated plants.

[0557] Compounds 1 to 5 from table a exhibit good activity in this test, i.e. a kill rate of more than 80%.

Example B-10

Activity Against Heliothis virescens

[0558] Young soya plants are sprayed with an aqueous emulsion spray liquor containing 1100 ppm active substance and, after the spray coating is dried on, are populated with 10 first-stage caterpillars of Heliothis virescens and placed in a plastic container. 6 days later, the percentage reduction in population and in feeding damage (% activity) is determined by comparing the number of dead caterpillars and the feeding damage between the treated and the untreated plants.

[0559] Compounds 1 to 5 from table a exhibit good activity in this test, i.e. a kill rate of more than 80%.

Example B-11

Activity Against Spodoptera littoralis

[0560] Young soya plants are sprayed with an aqueous emulsion spray liquor containing 100 ppm active substance and, after the spray coating is dried on, are populated with 10 third-stage caterpillars of Spodoptera littoralis and placed in a plastic container. 3 days later, the percentage reduction in population and in, feeding damage (% activity) is determined by comparing the number of dead caterpillars and the feeding damage between the treated and the untreated plants.

[0561] Compounds 1 to 5 from table a exhibit good activity in this test, i.e. a kill rate of more than 80%.

Example B-12

Activity Against Plutella xylostella Caterpillars

[0562] Young cabbage plants are sprayed with an aqueous emulsion spray liquor containing 100 ppm active substance and, after the spray coating is dried on, are populated with 10 third-stage caterpillars of Plutella xylostella and placed in a plastic container. 3 days later, the percentage reduction in population and in feeding damage (% activity) is determined by comparing the number of dead caterpillars and the feeding damage on the treated plants with those on the untreated plants.

[0563] Compounds 1 to 5 from table a exhibit good activity in this test, i.e. a kill rate of more than 80%.

Example B-13

Activity Against Musca domestica

[0564] A sugar cube is treated with a solution of the test substance such that the concentration of test substance after overnight drying is 250 ppm in sugar. This treated cube is placed together with a wet cottonwool pad and 10 adults of an OP-resistant strain of Musca domestica on an aluminium tray, covered with a glass beaker and incubated at 25° C. The mortality rate is determined after 24 hours.

[0565] C. Acaricidal Activities

Example B-14

Activity Against Tetranychus urticae

[0566] Young bean plants are populated with a mixed population of Tetranychus urticae and sprayed one day later with an aqueous emulsion spray liquor containing 400 ppm active substance. The plants are subsequently incubated at: 25° C. for 6 days and then evaluated. The percentage reduction in population (% activity) is determined by comparing the number of dead eggs, larvae and adults on the treated plants with those on the untreated plants.

[0567] Compounds 1 to 5 from table a exhibit good activity in this test, i.e. a kill rate of more than 80%.

Example B-15

Activity on a Mixed Population of Tetranychus cinnabarinus

[0568] Dilution Series.

[0569] Dwarf beans at the 2-leaf stage are populated with a mixed population (eggs, larvae/nymphs, adults) of an OP-tolerant Tetranychus cinnabarinus strain. 24 hours after infection, the products are applied to the plants at rates of 200, 100, and 50 mg AS/l in the automatic spray cabin. The substances are formulated and are diluted with water to the appropriate rates. The experiment is evaluated 2 and 7 days after application for percentage mortality against eggs, larvae/nymphs and adults.

Example B-16

Activity Against Boophilus microplus

[0570] Satiated female adult ticks are adhered to a PVC plate and covered with a cottonwool pad, and the pad is wetted with 10 ml of aqueous test solution containing 125 ppm active substance. The cottonwool pad is removed and the ticks are incubated for 4 weeks until oviposition. The activity is manifested either as mortality or sterility in the females or as ovicidal activity in the case of the eggs.

Claims

1. Compounds of the formula I

2. Compounds of the formula I according to claim 1, characterized in that R1 is methyl or ethyl, preferably methyl; R2 is methyl, ethyl, fluoromethyl or trifluoroethyl, preferably methyl; R3 is C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkynyl, C3-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy or C1-C6-alkoxycarbonyl, it being possible for the abovementioned groups to be partly or fully halogenated; and also CN, OCN or halogen; or R3 is phenyl which is unsubstituted or substituted from 1 to 3 times by identical or different substituents selected from halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkenyloxy, C2-C6-alkynyl, C3-C6-alkynyloxy, C1-C6-alkoxycarbonyl, CN, OCN, optionally substituted benzyl, optionally substituted phenyl, or optionally substituted phenoxy, it being possible for the above-mentioned aromatic groups to be substituted by one or more identical or different substituents selected from the group consisting of halogen, cyano, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino and C2-C6-alkenyl; or R3 is pyridyl, pyrimidinyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, which are unsubstituted or substituted from 1 to 3 times by identical or different substituents selected from halogen, cyano, nitro, aminocarbonyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkylsulfonyl, C1-C6-alkylsulfoxyl, C3-C6-cycloalkyl, optionally substituted arylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylthio, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylaminocarbonyl, di-C1-C6-alkylaminocarbonyl or C2-C6-alkenyl; R5 is hydrogen, methyl, ethyl, methoxymethyl, allyl, propargyl, 2,2,2-trifluoroethyl, methylcarbonyl, ethylcarbonyl or methoxycarbonyl, preferably methyl, ethyl, methoxymethyl, allyl or propargyl; and A is —CH2O— or —CH═N—.

3. Compounds of the formula I according to claim 2, characterized in that R2 is C1-C6-alkyl, fluoromethyl, difluoromethyl or 2,2,2-trifluoroethyl; R3 is C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, CN, C3-C6-cycloalkyl, phenyl which is unsubstituted or substituted from 1 to 3 times by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkenyloxy, C2-C6-alkynyl, C3-C6-alkynyloxy, CN, OCN, benzyl, phenyl, or phenoxy, in which the aromatic groups are unsubstituted or substituted 1 or 2 times by halogen, C1-C2-alkyl, C1-C2-haloalkyl or C1-C2-alkoxy; and A is —CH2O—.

4. Compounds of the formula I according to claim 3, characterized in that R3 is C1-C4-alkyl, C1-C4-alkoxy, or C1-C6-alkoxycarbonyl, or is phenyl which is unsubstituted or substituted 1 or 2 times by halogen, C1-C2-alkyl, C1-C2-haloalkyl or C1-C2-alkoxy.

5. Compounds of the formula I according to claim 1, characterized in that R1 is methyl, ethyl or cyclopropyl, preferably methyl; R2 is C1-C6-alkyl, preferably methyl or ethyl; R3 is C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-alkoxycarbonyl, CN, C3-C6-cycloalkyl; aryl, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy or heterocyclyloxy, it being possible for the hydrocarbon radicals and the cyclic radicals to be substituted as mentioned previously; R5 is hydrogen, methyl, ethyl, methoxymethyl, allyl, propargyl, 2,2,2-trifluoroethyl, methylcarbonyl, ethylcarbonyl or methoxycarbonyl, preferably methyl, ethyl, methoxymethyl, allyl or propargyl; and A is —CH2O— or —CH═N—.

6. Compounds of the formula I according to claim 5, characterized in that R3 is C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C1-C6-alkoxycarbonyl or C3-C6-cycloalkyl; and A is —CH2O—.

7. Compounds of the formula I according to claim 6, characterized in that R3 is phenyl which is unsubstituted or substituted 1 or 2 times by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkenyloxy, benzyl, phenyl or phenoxy, in which these aromatic groups are unsubstituted or substituted 1 or 2 times by halogen, C1-C2-alkyl, C1-C2-haloalkyl or C1-C2-alkoxy; and A is —CH2O— or —CH═N—.

8. Compounds of the formula I according to claim 1, characterized in that R1 is methyl, ethyl or cyclopropyl; R2 is C1-C6-alkyl, preferably methyl or ethyl, C2-C6-alkenyl, preferably allyl or C2-C6-alkynyl, preferably propargyl; R3 is phenyl substituted by QR4; R5 is hydrogen, methyl, ethyl, methoxymethyl, allyl, propargyl, 2,2,2-trifluoroethyl, methylcarbonyl, ethylcarbonyl or methoxycarbonyl, preferably methyl, ethyl, methoxymethyl, allyl or propargyl; and A is —CH2O— or —CH═N—.

9. Compounds according to claim 1 selected from the following group: methyl N-methyl-[2-({2-ethoxyimino-1-methyl-2-[4-(4-trifluoromethylphenoxy) phenyl]ethylidene}hydrazonomethyl)phenyl]-carbamate, methyl N-ethyl-[2-({2-ethoxyimino-1-methyl-2-[4-(4-trifluoromethylphenoxy)-phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-ethyl-[2-({2-ethoxyimino-1-ethyl-2-[4-(4-trifluoromethylphenoxy)-phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-methyl-[2-({2-ethoxyimino-1-ethyl-2-[4-(4-trifluoromethylphenoxy)-phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-methoxymethyl-[2-({2-ethoxyimino-1-methyl-2-[4-(4-trifluoromethyl-phenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]-carbamate, methyl N-propargyl-[2-({2-methoxyimino-1-methyl-2-[4-(4-trifluoromethyl-phenoxy)phenyl]ethylidene}hydrazonomethyl)phenyl]-carbamate, methyl N-propargyl-[2-({2-ethoxyimino-1-methyl-2-[4-(4-trnfluoromethylphenoxy)-phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-propargyl-[2-({2-ethoxyimino-1-ethyl-2-[4-(4-trifluoromethylphenoxy)-phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-propargyl-[2-({2-ethoxyimino-1-ethyl-2-[4-(4-trifluoromethylphenoxy)-phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-methyl-[2-({2-methoxyimino-1-methyl-2-(4-chlorophenyl)ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-methyl-[2-({2-methoxyimino-1-methyl-2-(4-fluorophenyl)ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-methoxyethyl-[2-({2-methoxyimino-1-methyl-2-(4-chlorophenyl)ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-methoxyethyl-[2-({2-methoxyimino-1-methyl-2-(4-fluorophenyl)ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-methyl-[2-({2-methoxyimino-1-methyl-2-[4-(3-trifluoromethylphenoxy)-phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-methyl-[2-({2-ethoxyimino-1-ethyl-2-[4-(3-trnfluoromethylphenoxy)-phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-methyl-[2-({2-ethoxyimino-1-ethyl-2-[4-(3-trifluoromethylphenoxy)-phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-methyl-[2-({2-methoxyimino-1-methyl-2-[4-(4-chloromethylphenoxy)-phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-methyl-[2-({2-ethoxyimino-1-methyl-2-[4-(4-chloromethylphenoxy)-phenyl]ethylidene}hydrazonomethyl)phenyl]carbamate, methyl N-methyl-{2-[2-(4-fluorophenyl)-2-methoxyimino-1-methylethylideneaminooxymethyl]phenyl}carbamate, methyl N-ethyl-{2-[2-methyl-2-methoxyimino-1-methylethylideneaminooxymethyl]phenyl}carbamate, methyl N-ethyl-{2-[2-(4-fluorophenyl)-2-methoxyimino-1-methylethylideneaminooxymethyl]phenyl}carbamate, methyl N-methoxymethyl-{2-[2-methyl-2-methoxyimino-1-methylethylideneaminooxymethyl]phenyl}carbamate, and methyl N-methyl-{2-[2-(4-(4-trifluoromethylphenoxy)phenyl)-2-ethoxyimino-1-methylethylideneaminooxymethyl]phenyl}carbamate.

10. Process for preparing the compounds of the formula I according to claim 1, characterized in that A) a compound of the formula I in which A is —CH═N— is-prepared by reacting a hydrazone of the general formula II 239 in which R1, R2 and R3 have the meanings indicated under formula I with an aldehyde of the general formula III or one of its acetal or imino derivatives of the general formulae IVa and IVb 240 in which R is C1-C6-alkyl or the two Rs together with the two oxygen atoms and the carbon to which they are attached are a cyclic acetal, or B) a compound of the formula I in which A is CH2O is prepared by reacting an oxime of the general formula V 241 in which R1, R2 and R3 have the meanings indicated under formula I: with a benzyl derivative of the general formula VI, 242 in which R5 and R6 have the meanings indicated under formula I and U is a leaving group, or C) a compound of the formula I in which R5 is C1-C4-alkyl, C1-C2-alkoxymethyl, C1-C2-alkylthiomethyl, C1-C3-haloalkylmethyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C3-alkylcarbonyl or C1-C2-alkoxycarbonyl is prepared by reacting a compound of the formula Ia 243 in which A, R1, R2, R3 and R6 have the meanings indicated under formula I with a compound of the general formula VII, R5a-Hal  VII  in which R5a with the exception of hydrogen has the meanings indicated for R5 and Hal stands for chlorine, bromine or iodine, or D) a compound of the formula I is prepared by reacting an aniline derivative of the general formula VIII 244 in which R1, R2, R3 and R5 have the meanings indicated under formula I with a chloroformate of the general formula IX Cl—COOR6  IX, or E) a compound of the formula I is prepared by etherifying an oxime of the general formula XV 245 in which R1, R3, R5 and R6 have the meanings indicated under formula I, or F) a compound of the formula I is prepared by reacting a ketone of the general formula XVI 246 in which R1, R3, R5 and R6 have the meanings indicated under formula I with an alkoxyamine of the general formula XIX R2—ONH2  XIX  in which R2 has the meanings indicated under formula I or with one of its salts.

11. Compositions comprising as active substance an effective amount of a compound of the formula I according to claim 1 together with a carrier material suitable for agriculture.

12. Method of controlling acarids and insects and for preventing the infestation of crop plants by phytopathogenic fungi, characterized in that a compound of the formula I according to claim 1 is applied to acarids, insects, crop plants or their habitat.

13. Use of the compounds of the formula I according to claim 1 for controlling acarids and insects and for preventing the infestation of crop plants by phytopathogenic fungi.