PESTICIDES

Abstract: Compounds of formula (I) in which where X is CH or N; Y is O; S, S=O or NR5; Z is OR2, SR2, N(R3)R4; or Y and Z together form 5- to 7-membered ring which contains, 2 or 3 hetero atoms O and/or N and which is unsubstituted or substituted by C1-C4 alkyl, halo-C1-C4alkyl, halogen, =O or cyclopropyl; V is a direct bond or C1-C6alkylene, which is unsubstituted or substituted by C1-C3alkyl, C2-C3alkylidene or C3-C6cycloalkylidene; U is O, S, NR7, SO or SO2; W is substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl; R1 is cyclopropyl; C1-C6alkyl or halo-C1-C6alkyl; R2 and R3 independently of one another are C1-C6alkyl or halo-C1-C6alkyl; R4 and R5 independently of one another are hydrogen, C1-C6alkyl or C1-C6alkoxy; R7 is hydrogen, C1-C6alkyl, benzyl, C1-C6alkylcarbonyl, halo-C1-C6alkylcarbonyl, halo-C2-C6alkenylcarbonyl; R21 and R22 independently of one another are hydrogen, halogen, C1-C8alkyl or C1-C8alkoxy or C1-C8alkylthio; R23, R24, R25, R26 independently of one another are hydrogen, halogen, C1-C8alkyl or C1-C8alkoxy; are pesticidally active. They can be used for pest control, in particular as fungicides, acaricides and insecticides in crop protection.

Description: Pesticides The invention relates to a novel pesticidally active compound of the formula I where X is CH or N, or Y and Z together form a 5- to 7-membered ring which contains 2 or 3 hetero atoms O and/or N and which is unsubstituted or substituted by C 1 -C 4 alkyl, halo-C,-C 4 alkyl, halogen, =0 or cyclopropyl, Y is a direct bond or C^Cealkylene which is unsubstituted or substituted by C t -C 3 alkyl, C 2 -C 3 alkylιdene or C 3 -C 6 cycloalkyiιdene, U is O, S, NR 7 , SO or S0 2l W is substituted or unsubstituted aryl or subsituted or unsubstituted hetaryl, R, is cyclopropyl, C,-C 6 alkyl or halo-C^Cealkyl, R 2 and R 3 independently of one another are or halo- R„ and R 5 independently of one another are hydrogen, C Cgalkyl or C,-C 6 alkoxy, R 7 is hydrogen, C,-C β alkyl, benzyl, C Cgalkylcarbonyl, halo-C^Cealkylcarbonyl, halo-C 2 - C 6 alkenylcarbonyl, R 21 und R 22 independently of one another are hydrogen, halogen, C,-C 8 alkyl or C,-C 8 alkoxy or C r C a alkylthιo, R 23 . R 2 . R 25 . R 26 independently of one another are hydrogen, halogen, C^Coalkyl or CrCβ¬ alkoxy The formula I embraces all stereoisomeric forms and mixtures of these, such as racemic and diasteromeπc mixtures, for example E/Z mixtures The compounds according to the invention have fungicidal, acaπcidal and insecticidal properties and are suitable as active ingredients for use in agriculture, in horticulture and in the hygiene sector The invention furthermore relates to the preparation of these compounds, to agrochemical compositions which comprise, as active ingredients, at least one of these compounds, and to the use of the active ingredients or of the compositions for protecting plants against attack by harmful microorganisms, and for controlling insects 2-alkoxιmιno-2-phenylacetιc acid derivatives and 2-alkoxymethylene-2-phenylacetιc acid derivatives as pesticides are disclosed, for example, in EP-A-253 213 and EP-A-178 826 Corresponding pesticide compounds which have a cyclohexenyl group instead of the phenyl group are described in EP-A- 21 102, those in which the phenyl group is replaced by a cyclohexyl group in EP-A-438 726 The phytofungicidal activity of 1 ,4-cyclohexadιene-1-alanιne is furthermore described in J of Antibiotics, Vol XXIII, No 1 1 , pp 537-541 (1970) The general terms used hereinabove and hereinbelow have the meanings given hereafter unless otherwise defined Aryl is phenyl, naphthyl, phenanthryl or fluorenyl, in particular phenyl Hetaryl are 5- or 6-membered aromatic rings which have hetero atoms N, O and/or S, and which can be benzo-fused Examples are furane, pyrrole, pyridine, pyπmidine, pyrazine, thiazole, oxazole, isoxazole, isothiazole, tnazine, quinolme, isoquino ne, pyπdazine, pyrazole, imidazole, quinazolme, quinoxaline, benzimidazole, benzofuran, indole, isoindole, benzothiazole, benzoxazole Heterocyclyl denotes 5- to 7-membered non-aromatic rings which contain 1-3 identical or different hetero atoms N, O, S Examples are Λ 2 -oxazolιne, Δ 2 - thiazohne, 5,6-dιhydro-4H-1 ,3-thιazιne, 5,6-dιhydro-4H-1 ,3-oxazιne, pyrrolidine, indolme, pipeπdine morpho ne, 4-alkylpιperιdιne, azepine Alkyl groups are straight-chain or branched, depending on the number of the carbon atoms, for example methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, sec- amyl, tert-amyl, 1-hexyl or 3-hexyl Unsaturated hydrocarbon radicals are alkenyl, alkynyl or alkenynyl groups having not more than 3 multiple bonds, for example butadienyl, hexatπenyl, 2-penten-4-ynyl Alkenyl is to be understood as meaning straight-chain or branched alkenyl, for example allyl, methallyl, 1-methylvιnyl or but-2-en-1-yl Preferred alkenyl radicals are those which have a chain length of 3 to 4 carbon atoms Alkynyl can also be straight-chain or branched, depending on the number of the carbon atoms, for example ethynyl, propargyl, but-1-yn-1-yl, but-1-yn-3-yl Propargyl is preferred Halogen or halo are fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine Haloalkyl can contain identical or different halogen atoms, for example fluoromethyl, difluoromethyl, difluorochloromethyl, tπfluoromethyl, chloromethyl, dichloromethyl, tnchloromethyl, 2,2,2-trιfluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2,2,2-tπchloroethyl, 3,3,3- tnfluoropropyl Alkoxy is, for example, methoxy, ethoxy, propyloxy, i-propyloxy, n-butyloxy, iso-butyloxy, sec-butyloxy and tert-butyloxy, preferably methoxy and ethoxy Haloalkoxy is, for example, difluoromethoxy, tπfluoromethoxy, 2,2,2-trιfluoroethoxy, 1 ,1 ,2,2- tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2-dιfluoroethoxy Cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl Alkanoyl is either straight-chain or branched, examples are formyl, acetyl, propionyl, butyryl, pivaloyl or octanoyl All the alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkoxy and alkanoyl groups mentioned hereinabove and hereinbelow can be substituted by aryl, hetaryl, aryloxy, hetaryloxy, arylsulfenyl, arylsulfinyl, arylsulfonyl, heterarylsulfenyl, hetarylsulfinyl or heterarylsulfonyl, each of which is unsubstituted or additionally substituted All the aryl and hetaryl groups mentioned hereinabove and hereinbelow can be mono- or polysubstituted, for example by halogen, C C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C^alkoxy, C r C 4 alkylthιo, C r C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 haloalkoxy, halogen, cyano, cyano-C,-C 2 alkyl, cyano-CrCzalkoxy, OH, N0 2 , SCN, thiocyanomethyl, Sι(CH 3 ) 3 , NH 2 , NH(C 1 -C 4 alkyl), N(C,-C 4 alkyl) 2 , C Calkoxymethyl, C,-C 4 haloalkylcarbonyl, C,-C 4 haloalkyloxycarbonyl, C 1 -C 4 alkylcarbonyl, C^C^ alkoxycarbonyl, aminocarbonyl, C,-C 4 alkylamιnocarbonyl, bιs(C 1 -C 4 alkylamιno)carbonyl, arylaminocarbonyl, arylaminothiocarbonyl, C r C 4 alkoxιmιnomethyl, -CSNH 2l -SH, C,- C 4 alkylthιomethyl, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 2 -C 4 haloalkenyloxy, C,- C 4 alkylsulfιnylmethyl, C C 4 alkylsulfonylmethyl, phenylsulfinylmethyl, phenylsulfonylmethyl, trifluoromethylsulfonyl, C 3 -C 6 cycloalkyl, C,-C 4 haloalkylcarbonyloxy, C 1 -C 4 alkylcarbonyloxy, C r C 4 alkoxycarbonyloxy, haloalkoxycarbonyloxy, aminocarbonyloxy, C 1 -C 4 alkylamιnocarbonyloxy, bιs(C 1 -C 4 alkylamιno)carbonyloxy, arylammocarbonyloxy, arylaminothiocarbonyloxy All the abovementioned enumerations are by way of example and not by limitation Preferred are the following groups (1) Compounds of the formula I in which W is a group a) — (. , in which D are identical or different substituents halogen, cyano, nitro, CrC^alkyl, halo-C,-C 6 alkyl, C 2 -C 12 alkenyl, halo-C 2 -C, 2 alkenyl, C 2 -C 12 alkynyl, halo-C 2 -C 12 alkynyl, free or halogenated C 3 - C 6 cycloalkyl, free or halogenated C 3 -C 6 cycloalkylmethyl, free or halogenated C 3 - C 6 cycloalkylmethyloxy, C 1 -C 4 alkoxy, halo-C^Calkoxy, C 2 -C 6 alkenyloxy, halo-C 2 - C 6 alkenyloxy, C 2 -C 6 alkynyloxy, halo-C 2 -C 6 alkynyloxy, C 2 -C 12 alkoxyalkyl, C r C 4 alkoxycarbonyl, C,-C 6 alkylcarbonyl, it being possible for all the abovementioned alkyl, alkenyl or alkynyl groups to be substituted by aryl or hetaryl, aryloxy or hetaryloxy, arylsulfenyl, arylsulfinyl, arylsulfonyl, hetarylsulfenyl, hetarylsulfinyl or hetarylsulfonyl radicals, each of which can be additionally substituted or unsubstituted; furthermore substituted or unsubstituted aryl, substituted or unsubstituted hetaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxy, substituted or unsubstituted benzyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted cyclohexenylalkoxy, substituted or unsubstituted cyclohexenylalkylthio, substituted or unsubstituted cyclohexadienyl, substituted or unsubstituted cyclohexadienylalkoxy, substituted or unsubstituted cyclohexadienylalkylthio, substituted or unsubstituted fused ring having up to 14 C atoms, or in which D is once the group I n in which R 13 is hydrogen, cyano, C Cgalkyl, C 3 -C 6 cycloalkyl, CrCealkoxycarbonyl, C^acy!, C,-C 2 - alkoximino-C Csalkyl, aryl, hetaryl, heterocyclyl, naphthyl, C r C 6 alkoxy, aryloxy, hetaryloxy, C,-C 6 alkylamιno, bιs(C 1 -C 6 -alkyl)amιno, arylamino, hetarylamino, in which all the abovementioned radicals (with the exception of cyano) can be unsubstituted or substituted by alkyl, alkoxy, haloalkyl, haloalkoxy, alkylthio, alkylsulfenyl, alkylsulfmyl, halogen, nitro, cyano, aryl, aryloxy, hetaryl, hetaryloxy, or R 13 is the group in which R 15 is hydrogen, CrCealkyl, halo-C^Cealkyl, C,-C 6 alkoxy, halo-C,-C 6 alkoxy, halogen, C 3 - C 6 cycloalkyl which is unsubstituted or substituted by 1 to 5 halogen atoms, C 2 -C 6 alkenyl, halo-C 2 -C 6 alkenyl, substituted or unsubstituted C 2 -C 6 alkynyl, aryl, hetaryl or heterocyclyl, al three of which independently of one another are unsubstituted or monosubstituted to pentasubstituted by C,-C 6 alkyl, halo-C,-C 6 alkyl, halogen, C,-C 6 alkoxy or halo-C Cgalkoxy, tπ(C 1 -C 4 -alkyl)sιlyl, dι(C r C 4 -alkyl)phenylsιlyl, where, if m is greater than 1 , the radicals R 15 can be identical or different, Q is a direct bond, C r C 8 alkylene, C 2 -C 6 alkenylene, C 6 -C 6 alkynylene, O, 0(C,-C 6 alkylene), (C C 6 alkylene)0, S(=0) p , S(=O) p (C,-C β alkylene) or (C,-C 6 alkylene)S(=0) p , n is O, 1 , 2, 3, 4 or 5, m is 0, 1 , 2, 3, 4 or 5, p is 0, 1 or 2, and R 14 is hydrogen, C r C 6 alkyl, C^Cehaloalkyl having 1 to15 halogen atoms, C,-C 4 alkoxy-C 1 - C 2 alkyl, C 2 -C 4 alkenyl-C 1 -C 2 alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms, C 2 -C 4 alkynyl-C,-C 2 alkyl, C 3 -C 6 cycloalkyl which is unsubstituted or substituted by 1 to 4 halogen atoms, C 3 -C β cycloalkyl-C 1 -C 4 alkyl which is unsubstituted or substituted by 1 to 4 halogen atoms, cyano-C r C 4 alkyl, C 1 -C 4 alkoxycarbonyl-C 1 -C 4 alkyl, phenyl-C,-C 3 alkyl which is unsubstituted or substituted by halogen, C r C 3 alkyl, C r C 4 alkoxy, C 1 -C 4 haloalkyl, cyano, nitro, C 1 -C 4 alkylenedιoxy, it being possible for the phenyl group to be substituted by 1 to 3 identical or different substitutents, phenyl which is unsubstituted or monosubstituted or disubstituted by independent substituents from the series consisting of C,-C 4 alkyl, C 1 -C 4 alkoxy, halogen, C r C 2 haloalkyl having 1 to 3 halogen atoms, nitro or cyano, pyndyl which is unsubstituted or monosubstituted or disubstituted by independent substituents from the series consisting of C^Calkyl, C,-C 4 alkoxy, halogen, C,-C 2 haloalkyl having 1 to 3 halogen atoms, nitro or cyano (2) Compounds of the formula I in which R, is methyl, R 2 , R 3 und R 5 independently of one another are C,-C 2 alkyl, preferably methyl, R 4 is hydrogen (3) Compounds of the formula I in which X is N, Y is O, S, or S=O, preferably O, Z is OR 2 , SR 2 , N(R 3 )H, preferably OR 2 , SR 2 , R 2 and R 3 are C 1 -C 2 alkyl, preferably methyl (4) Compounds of the formula I in which Y is O, S, or S=0, preferably O, Z is OR 2 , R 2 is C r C 2 -Alkyl, preferably methyl (5) Compounds of the formula I in which Y and Z together are a group and in which A is alkanediyl having 1 to 3 carbon atoms which is unsubstituted or substituted by methyl, preferably dimethylene (ethane-1 ,2-dιyl), R 6 is hydrogen, C,-C 3 alkyl, cyclopropyl or CF 3 , (6) Compounds of the formula I in which V is -CH 2 -, -CH(CH 3 )-, -CH(CH 3 ) 2 -, -(CH 2 ) 2 -, -(CH 2 ) 3 -, U is O, R 21 and R 22 independently of one another are hydrogen, chlorine, bromine, C C 4 alkyl or C,- C 4 alkoxy, in particular methyl, R23. R2 . R25. R26 are hydrogen (7) Compounds of the formula I in which X is CH or , Y is O, V is -CH 2 -, U is O, W is substituted or unsubstituted phenyl, R 21 and R 22 independently of one another are hydrogen, chlorine or methyl, in particular methyl, R 23 . R 25 , R 26 are hydrogen (8) Amongst (7) in particular compounds of the formula I in which W is phenyl which is substituted by C,-C 8 alkyl, halo-Chalky!, C 2 -C 4 alkenyl, halo-C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, halo-C 2 -C 4 alkynyl, C r C 4 alkoxy, halo-C,-C 4 alkoxy, C 2 -C 6 alkenyloxy, halo-C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, halo-C 2 -C 4 alkynyloxy, C,-C 4 alkoxycarbonyl, C Cealkylcarbonyl, the abovementioned alkyl, alkenyl and alkynyl groups being unsubstituted or further substituted by aryl, hetaryl, aryloxy, hetaryloxy, arylsulfenyl, arylsulfinyl, arylsulfonyl, hetarylsulfenyl, hetarylsulfinyl or hetarylsulfonyl, each of which is unsubstituted or additionally substituted, furthermore aryl, hetaryl, heterocyclyl, arylcarbonyl, aryloxy, benzyl, cycloalkyl, cyclohexenyl, cyclohexenylalkoxy, cyclohexenylalkylthio, cyclohexadienyl, cyclohexadienylalkoxy, cyclohexadienylalkylthio, all the abovementioned cyclic groups being unsubstituted or mono- or polysubstituted by halogen, d-C^lkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C,-C 4 alkoxy, C,- C 4 alkylthιo, C 1 -C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, C,-C haloalkoxy, halogen, cyano, cyano-C 1 -C 2 alkyl, cyano-C,-C 2 alkoxy, OH, N0 2 , SCN, thiocyanomethyl, Sι(CH 3 ) 3 , NH 2 , NH(C C 4 alkyl), N(C 1 -C 4 alkyl) 2 , C r C 4 alkoxymethyl, d-Chaloalkylcarbonyl, C,- C 4 haloalkyloxycarbonyl, C,-C 4 alkylcarbonyl, C,-C 4 alkoxycarbonyl, aminocarbonyl, d-C,- alkylaminocarbonyl, bιs(C,-C 4 alkylamιno)carbonyl, arylaminocarbonyl, arylaminothiocarbonyl, C 1 -C 4 alkoxιmιnomethyl, -CSNH 2 , -SH, C 1 -C 4 alkylthιomethyl, C 2 -C 4 - alkenyloxy, C 2 -C 4 alkynyloxy, C 2 -C 4 haloalkenyloxy, C r C 4 alkylsulfιnylmethyl, C,-C 4 alkyl- sulfonylmethyl, phenylsulfinylmethyl, phenylsulfonylmethyl, tnfluoromethylsulfonyl, C 3 -C 6 - cycloalkyl, C r C 4 haloalkylcarbonyloxy, C 1 -C 4 alkylcarbonyloxy, C,-C 4 alkoxycarbonyloxy, haloalkoxycarbonyloxy, aminocarbonyloxy, C 1 -C 4 alkylamιnocarbonyloxy, bιs(C,-C 4 - alkylamιno)carbonyloxy, arylaminocarbonyloxy or arylaminothiocarbonyloxy (9) Compounds of the formula I in which V is -CH 2 -, -CH(CH 3 )-, -CH(CH 3 ) 2 -, -(CH 2 ) 2 -, -(CH 2 ) 3 -, U ιs S or NR 7 , R 21 and R 22 independently of one another are halogen, chlorine, bromine, C,-C 4 alkyl or C,- C 4 alkoxy, in particular methyl, R23. 2 4 . 25. 26 are hydrogen (10) Compounds of the formula I in which D is halogen, C,-C 4 alkyl, halo-C,-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, free or chlorinated cyclopropylmethyl, C r C 4 alkoxy halo-C,-C 4 alkoxy, C 6 -C 12 alkoxyalkyl, CrC 4 acyl, Cι-C 4 alkoxycarbonyl, free or chlorinated cyclopropylmethyloxy, or substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted benzyl, wherein the substituents on aryl, aryloxy and benzyl are selected from the series consisting of halogen, nitro, CrC 2 -alkyl, halo-Cι-C 2 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, d- C 2 alkoxy, halo-CrC 2 alkoxy, C 2 -C 12 alkoxyalkyl; n is 0, 1 , 2 or 3. (11 ) Amongst (10), those in which: D is halogen, C 1 -C 4 alkyl, halo-Cι-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, free or chlorinated cyclopropylmethyl, CrC 4 alkoxy, halo-d-dalkoxy, Cι-C 4 acyl, Cι-C 4 -alkoxycarbonyl, free or chlorinated cyclopropylmethyloxy, n is 0, 1 or 2. (12) Compounds of the formula I in which: D is the group in which R 13 is hydrogen, cyano, CrC alkyl, cyclopropyl, C C 4 alkoxycarbonyl, Cι-C acyl, CrC 2 alkoximino-CrC 6 alkyl, or the group in which R^ is d-Cealkyl, halo-CrC 6 alkyl, d-C 6 alkoxy, halo-d-C 6 alkoxy, halogen, C 3 -C 6 cycloalkyl which is unsubstituted or substituted by 1 to 5 halogen atoms, C 2 -C 6 alkenyl; halo-C 2 - C 6 alkenyl, substituted or unsubstituted C 2 -C 6 alkynyl; aryl, hetaryl or heterocyclyl, all three of which independently of one another are unsubstituted or monosubstituted to pentasubstituted by CrC 6 alkyl, halo-Cι-C 6 alkyl, halogen, C C 6 alkoxy or halo-d-Cealkoxy; tri(C,-C 4 alkyl)silyl, di(Cι-C 4 alkyl)phenylsilyl; where, if m is greater than 1 , it is possible for the radicals Rι 5 to be identical or different; Q is a direct bond, C C β alkylene, C 2 -C 6 alkenyiene, C 2 -C 6 alkinylene, O, O(Cι-C 6 alkylene), (Cι-C 6 alkylene)O, S(=O) p , S(=O) p (d-C 6 alkylene) or (C 1 -C β alkylene)S(=O) p ; n is 0, 1 , 2, or 3; m isO, 1 , 2, or 3, p is 0, 1 or 2, and R )4 is hydrogen, C,-C 4 alkyl, C 1 -C 4 haloalkyl having 1 to 6 halogen atoms, C 2 -C 4 alkenyl, C 2 - dhaloalkenyl having 1 to 3 halogen atoms (14) Amongst (13), those in which R 15 is d-C 6 alkyl, halo-C,-dalkyl, cyclopropyl which is unsubstituted or substituted by 1 to 5 chlorine atoms, C 2 -C 6 alkenyl which is unsubstituted or substituted by 1 to 3 halogen atoms, or unsubstituted or substituted C 2 -C 6 alkynyl, furthermore phenyl which is unsubstituted or monosubstituted to pentasubstituted by C,-C 6 alkyl, halo-C r C 6 alkyl, halogen, C r C 6 alkoxy or halo-d-C 6 -alkoxy, or pyndyl which is unsubstituted or monosubstituted to pentasubstituted by d-C 6 alkyl, halo-C,-C 6 -alkyl, halo, d-C 6 alkoxy or halo-C,-C 6 alkoxy, Q is a direct bond, C 1 -C 4 alkylene, O, O(C,-C 4 alkylene), (d-d-alkylene)O, m is O, 1 , 2 (14) Amongst (11 ), those in which R 13 is hetaryl or heterocyclyl which, independently of one another, are unsubstituted or monosubstituted to pentasubstituted by d-C 6 alkyl, halo-C,-C 6 alkyl, halogen, d-C 6 -alkoxy or halo-C r C 6 -alkoxy (15) Compounds of the formula I in which W is substituted or unsubstituted pyndyl, pynmidinyl, imidazolyl, thiazolyl, 1 ,3,4-thιadιazolyl, tnazolyl, thienyl, furanyl, pyrrolyl, quinolyl, isoquinolyl, benzoxazolyl, quinoxalinyl, benzothiazolyl, benzimidazolyl, or indolyl (16) Compounds of the formula I in which W is pyndyl or pynmidinyl, each of which is unsubstituted or substituted by C r C 4 alkyl, halo- C r C 4 alkyl, C 2 -C 6 alkenyl, halo-C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, halo-C 2 -C 6 alkynyl, C r C 4 alkoxy, halo-C,-C 4 alkoxy, C 2 -C 12 alkoxyalkyl, C^Csacyl, C,-C 4 alkoxycarbonyl, substituted or unsubstituted phenyl, substituted or unsubstituted phenoxy, or substituted or unsubstituted benzyl (17) Compounds of the formula I in which V is a direct bond or -CH 2 -, U is O, W is pyndyl or pynmidinyl, each of which is unsubstituted or substituted by d-C 4 alkyl, halo- C 1 -C 4 alkyl, phenyl, phenoxy or benzyl and in which phenyl, phenoxy and benzyl are unsubstituted or monosubstituted to trisubstituted by halogen, C,-C 4 alkyl, C 2 -C 4 alkenyl, halo- C r C 4 alkyl, halo-C 2 -C 4 alkenyl, C,-C 4 alkoxy, halo-d-C 6 alkoxy or cyano Compounds of the formula I can be prepared as shown in reaction scheme 1 and 2, as follows Scheme 1 K) CICOOR V. - • N(R 3 3 1 1)'R , Λ 32 < ΗN(R 31 )R 3 . <^ v* ) IX J) T-Hal (VII) T-Hal (VII) HU-W (V) ~N(R 31 )R 3 N) V. V ^ u' W XI VIII VI F) dιene (ll) E) diene (II) D) T-Hal (VII) W a diene (II) L leaving group Hal- halogen, in particular chlorine and bromine Scheme 2 1) etalation V w ^u ^ w U 2) T r Hal or T r O(C C 6 alkyl) / P) VI 0) XIII E) diene (II) S) HNR 3 R 4 R. , O The individual reaction steps can be carried out as follows A), E), F) under conditions known from, and applicable to, Diels-Alder reactions, in the presence or absence of solvents, and in the presence or absence of a catalyst, at -40 to 250°C, preferably -20 to 200°C, in particular 100-200°C B), G) reaction in a solvent under alkaline conditions C), K) reaction with a chloroformic ester in the presence or absence of solvents under anhydrous conditions D), H), J) under conditions known for, and applicable to, Heck reactions, in the presence of a Pd catalyst (for example F A Carey and R J Sundberg, Advanced Organic Chemistry, pages 418-420, Plenum Press 1990) M) exchange of the leaving group for an ammo group under alkaline conditions N) Reaction with a chloroformic ester in the presence or absence of solvents, under anhydrous conditions, to give a compound of the formula VIII in which L is chlorine, if desired followed by exchange of the chlorine atom for another leaving group such as bromine, tosylate or mesylate O) 1 ) Metalation with suitable reagents, for example methylmagnesium chloride, sodium hydride, alkyllithium, potassium tertiary-butylate and, if desired, transmetalation with copper iodide or similar salts and 2) subsequent acylation of the metal acety de with an oxalic acid derivative TCI, in particular with T,-CI or T 1 -0(C 1 -C 3 alkyl) in a solvent Q) Wittig reaction, for example with methoxymethyltriphenylphosphonium chloride and base in an inert solvent R) oxime formation either (a) with a hydroxylamine derivative of the formula H 2 NOR, in a neutral or alkaline solvent, if appropriate with the addition of a base or (b) with hydroxylamine H 2 NOH or a salt thereof followed by alkylation with an alkylating agent R L, in which L is a leaving group S) Conversion of an ester into an amide by treating the ester with an amine HNR 3 R 4 in a suitable solvent Typical reaction conditions can be seen from the examples The cyclohexadiene derivatives of the formulae I, IV XII and XIV can be converted by known methods, either by dehydrogenation to the corresponding aromatic compounds or by hydrogenation into the corresponding cyclohexene or cyclohexane derivatives Examples of suitable bases are alkali metal or alkaline earth metal hydroxides, hydrides, amides, alkoxides, carbonates, dialkylamides or alkylsilylamides, alkylamines, alkylenediamines, free or N-alkylated saturated or unsaturated cycloalkylamines, basic heterocycles, ammonium hydroxides and carbocyclic amines Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium carbonate, potassium tert-butoxide, potassium carbonate, lithium dnsopropylamide, potassium bιs(trιmethylsιlyl)amιde, calcium hydride, triethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dιmethylamιne, N,N-dιethylanιlιne, pyridine, 4-(N,N- dιmethylamιno)pyrιdιne, N-methylmorpholme, benzyltπmethylammonium hydroxide and 1 ,8- dιazabιcyclo[5 4 0]undec-5-ene (DBU) Examples of leaving groups are chlorine, bromine, iodine, d-C 8 alkylthιo such as methylthio, ethylthio or propylthio, d-C β alkanoyloxy such as acetoxy, (halo)d-C 8 alkanesulfonyloxy such as methanesulfonyloxy, ethanesulfonyloxy or tπfluoromethanesulfonyloxy, or substituted or unsubstituted phenylsulfonyloxy such as benzenesulfonyloxy or p-toluenesulfonyloxy, imidazolyl or hydroxyl, preferably chlorine, bromine, iodine, tπfluoromethanesulfonyloxy and p-toluenesulfonyloxy The reactants can be reacted with each other as such, i e without addition of a solvent or diluent, for example, in the melt In most cases, however, the addition of an inert solvent or diluent or of a mixture of these is advantageous Examples of such solvents or diluents which may be mentioned are aromatic, aliphatic and alicyclic hydrocarbons and halohydrocarbons such as benzene, toluene, xylene, chlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, tπchloromethane, dichloroethane or tπchloroethane, ethers such as diethyl ether, tert-butyl methyl ether, tetrahydrofuran or dioxane, ketones such as acetone or methyl ethyl ketone, alcohols such as methanol, ethanol, propanol, butanol, ethylene glycol or glycerol, esters such as ethyl acetate or butyl acetate, amides such as N,N-dιmethylformamιde, N,N-dtmethylacetamιde, N- methylpyrro done or hexamethylphosphoπc triamide, nitrites such as acetonitrile, and sulfoxides such as dimethyl sulfoxide Bases employed in an excess, such as triethylamine, pyridine, N-methylmorpho ne or N,N-dιethylanιlιne, can also act as solvents or diluents The reaction can also be carried out with phase transfer catalysis in an organic solvent, for example methylene chloride or toluene, in the presence of an aqueous alkaline solution, for example sodium hydroxide solution, and of a phase transfer catalyst, for example tetrabutylammonium hydrogen sulfate The invention also relates to novel starting materials and intermediates used for the preparation of the compounds of the formula I, their use and processes for their preparation The following processes are of particular importance (1) The process for the preparation of the compound of the formula I which comprises reacting a compound of the formula II with the compound of the formula III M III in which X, Y, Z, R,, V, U, W and R 21 to R 26 have the meanings given for formula I (2) Process for the preparation of a compound of the formula I, which comprises reacting a compound of the formula IV with a compound of the formula V IV in which X, Y, Z, R,, V, U, R 21 to R 26 and W have the meanings given for formula I and in which L is a leaving group in a solvent under alkaline conditions. (3) Process for the preparation of a compound of the formula XIV which comprises reacting a compound of the formula II with a compound of the formula XIII XIV in which Y, Z, V, U, W and R 21 to R 26 have the meanings given for formula I according to claim 1. Especially important are the intermediates of the formulae III, XIII and XIV in which X, Y, Z, V, U, W, R,, R 21 to R Z6 have the meanings given for formula I The compounds of the formula T-Hal (VII) in which T has the abovementioned meanings and Hal is halogen can be prepared as described, for example, in WO/20569 The groups mentioned for X, Y and Z in formula I can be converted into each other by known methods, for example WO 94/26700 and WO 95/04728, both at the final level and at any suitable intermediate level The compounds of the formula I can be employed preventively and/or curatively in the agricultural sector and related fields as active ingredients in the control of plant pests The active ingredients of the formula I according to the invention are distinguished by a good activity, even at low rates of concentration, and by the fact that they are well tolerated by plants and are environmentally friendly They have very advantageous, in particular systemic, properties and can be employed for protection of a large number of crop plants Using the active ingredients of the formula I, it is possible to contain or destroy the pests which are found on plants or plant organs (fruits, flowers, foliage, stalks, tubers, roots) of a variety of useful plants, and even plant organs which grow at a later point in time remain unharmed, for example by phytopathogenic microorganisms Moreover, the compounds I can be employed as seed-dressing agents for the treatment of seeds (fruits, tubers, kernels) and plant cuttings as a protection against fungal infections and against soil-borne phytopathogenic fungi The compounds I act for example against the phytopathogenic fungi which belong to the following classes Fungi imperfecti (for example Botrytis, Pyriculaπa, Helminthospoπum Fusanum, Septona, Cercospora and Alternaria), Basidiomycetes (for example Rhizoctonia Hemileia, Puccinia), Ascomycetes (for example Ventuna and Erysiphe, Podosphaera, Moni nia, Uncinula) and Oomycetes (for example Phytophthora, Pythium, Plasmopara) Target crops for the application in crop protection are, within the scope of the invention, for example the following plant species cereals, (wheat, barley, rye, oats, rice, maize, sorghum and related species), beet (sugar and fodder beet); pome fruit, stone fruit, soft fruit (apples pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries), leguminous plants (beans, lentils, peas, soya), oil crops (oil seed rape, mustard, poppies olives, sunflowers, coconut, castor, cocoa, peanuts), cucurbits (pumpkin, cucumbers, melons), fibre crops (cotton, flax, hemp, jute), citrus fruit (oranges, lemons, grapefruit, tangerines), various 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, sugar cane, tea, pepper, grapevines hops, the plantain family, latex plants and ornamentals The compounds of the formula I according to the invention are furthermore valuable active ingredients against insects and pests from the order Acartna, as found on useful plants and ornamentals in agriculture, in horticulture and in forests, while being well tolerated by warm¬ blooded species, fish and plants 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 Pests which can be controlled are mainly spider mites such as Panonychus ulmi, aphids such as Aphis craccivora, caterpillars lepidopterans, such as those of He othis virescens, and rice leafhoppers such as Nilaparvata lugens or Nephotettix cincticeps The good pesticidal activity of the compounds I according to the invention corresponds to a mortality of at least 50-60 % of the abovementioned pests Further fields of application of the active ingredients according to the invention are the protection of stored products and of materials, in which case the stored material is protected against rotting and becoming mouldy and also against animal pests (for example grain weevil, mites, maggots and the like) In the hygiene sector, compounds of the formula I effect successful control of animal parasites such as ticks, mites, warble flies and the like on domestic animals and productive livestock The compounds I act against individual or all developmental stages of normally sensitive, but also resistant species of pests In the present context, their activity may become apparent for example in destruction of the pests, either immediately or only after some time has elapsed, for example during ecdysis, or in a reduced oviposition and/or hatching rate Active ingredients I are normally used in the form of compositions and can be applied to the plant or area to be treated simultaneously with other active ingredients, or in succession These other active ingredients can be, for example, fertilizers, trace element mediators or other preparations which affect plant growth In this context, selective herbicides, but also insecticides, fungicides, bacteπcides, nematicides, molluscicides or mixtures of a plurality of these together with, if desired, other carriers conventionally used in the art of formulation, surfactants of other application-enhancing additives may also be used Suitable carriers and additives can be solid or liquid and are substances expediently used in the art of formulation, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers A preferred process for applying an active ingredient of the formula I, or of an agrochemical composition which comprises at least one of these active ingredients, is application to the foliage (foliar application) Frequency and rate of application depend on the risk of infestation with the pathogen in question Alternatively, the active ingredients I can reach the plant through the soil via the root system (systemic action), by drenching the locus of the plant with a liquid preparation or by incorporating the substances into the soil in solid form, for example in the form of granules (soil application) In the case of paddy rice, such granules can be metered into the flooded paddy field Alternatively, the compounds I can be applied to seed kernels for the purposes of seed treatment (coating), either by soaking the kernels or tubers in a liquid preparation of the active ingredient or by coating them with a solid preparation The compounds I are employed as such or, preferably, together with the auxiliaries conventionally used in the art of formulation To this end, they are processed in a known manner, expediently to give, for example, emulsion concentrates, spreadable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts or granules, for example by encapsulation in, for example, polymeric substances The methods of application, such as spraying, atomizing, dusting, scattering, brushing on or pouring, and the type of composition are selected to suit the intended aims and prevailing circumstances Useful rates for application are, generally, 1 g to 2 kg of active substance (a s ) per hectare (ha), preferably 10 g to 1 kg of a s /ha, in particular 20 g to 600 g a s /ha When used as a seed-dressing agent, it is advantageous to use doses of from 10 mg to 1 g of active substance per kg of seed The formulations, i e the compositions, preparations or products comprising the active ingredient of the formula I and, if desired, a solid or liquid additive, prepared in the manner known per se, for example by intimately mixing and/or grinding the active ingredient with extenders, such as solvents, solid carriers and, if desired, surface-active compounds (surfactants) The following are suitable as solvents aromatic hydrocarbons, preferably the fractions C 8 to C 12 , such as xylene mixtures or substituted napthalenes, phthahc esters such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones such as cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolιdone, dimethyl sulfoxide or dimethylformamide, and free or epoxidized vegetable oils, such as epoxidized coconut oil or soya oil, and water Solid carriers which are used, for example, for dust and dispersible powders are, as a rule, ground natural minerals such as calcite, talc, kaolin, montmoπllonite or attapulgite To improve the physical properties, it is also possible to add highly disperse silica or highly disperse absorptive polymers Suitable particulate adsorptive carriers for granules are porous types, such as pumice, brick grit, sepiolite or bentonite, and suitable non-sorptive carrier materials are, for example, calcite or sand In addition, a large number of pregranulated materials of inorganic or organic nature, such as dolomite or comminuted plant residues, may be used Surface-active compounds are, depending on the nature of the active ingredient of the formula I to be formulated, non-ionic, cationic and/or anionic surfactants which have good emulsifying, dispersing and wetting properties Surfactants are also to be understood as meaning surfactant mixtures Suitable anionic surfactants can be both so-called water-soluble soaps and water-soluble synthetic surface-active compounds Examples of non-ionic surfactants which may be mentioned are nonylphenylpolyethoxyethanoles, castor oil polyglycol ethers, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethylenethanol, polyethylene glycol and octylphenoxypolyethoxyethanol Fatty acid esters of polyoxyethylenesorbitan, such as polyoxyethylenesorbitan tnoleate, are furthermore also suitable The cationic surfactants are mainly quaternary ammonium salts which have, as N- substituents, at least one alkyl radical having 8 to 22 C atoms and, as further substituents, lower, free or halogenated alkyl, benzyl or lower hydroxyalkyl radicals Other surfactants conventionally used in the art of formulation are known to those skilled in the art or can be found in the relevant specialist literature As a rule, the agrochemical preparations comprise 0,1 to 99 percent by weight, in particular 0 1 to 95 percent by weight, of active ingredient of the formula I, 99 9 to 1 percent by weight, in particular 99 8 to 5 percent by weight, of a solid or liquid additive and 0 to 25 percent by weight, in particular 0 1 to 25 percent by weight, of a surfactant While more concentrated compositions are preferred as commercially available goods, the end user uses, as a rule, dilute compositions The compositions may also comprise other additives such as stabilizers, antifoams, viscosity regulators, binders or tackifiers, and also fertilizers or other active ingredients for achieving specific effects Preparation examples Temperatures in "Celsius Abbreviations e = methyl, Et = ethyl, Pr = n-propyl i-Pr = isopropyl, Bu = butyl, i-Bu = isobutyl, Ph = phenyl, THF = tetrahydrofuran TPP = tπphenylphosphine H-1 1 -methyl-2-(prop-2-vnyloxy)benzene 245 g of potassium carbonate and 75 ml of propargyl chloride are added to a solutions of 96 g of o-cresol in 1500 ml of acetonitrile The mixture is now heated for 14 hours at 65°, cooled to room temperature, and filtered with suction, and the filtrate is evaporated The residue is taken up in 150 ml of ethyl acetate, the mixture is filtered with suction and the filtrate is evaporated This gives 134 g of the total compound as a pale brown oil H-2 methyl methoxyιmιno-5-o-tolyloxypent-3-vnoate (Comp 16 004) 60 g of 1-methyl-2-prop-2-ynyloxybenzene, 0 3 g of copper(l) iodide and 1 g of Pd (TPP) 2 Cl 2 are added to a solution of 39 5 g of monomethyl 2- methoxyiminomonochlorooxalate in 1000 ml of triethylamine and 80 ml of THF The mixture is now stirred for 14 hours at 80° The mixture is subsequently filtered with suction and the filtrate is evaporated The oily residue is chromatographed on silica gel (ether/hexane 1 2) and the combined fractions are evaporated This gives 44 g of the title compound H-3 methyl (4,5-dιmethyl-2-o-tolyloxymethylcvclohexa-1 ,4-dιenyl)methoxyιmιno acetate (Comp 2 002) 20 ml of 2,3-dιmethylbuta-1 ,3-dιene are added to a solution of 7 5 g of methyl 2- methoxyιmιno-5-o-tolyloxypent-3-ynoate in 5 ml of toluene The reaction mixture is heated for 14 hours at 130° in an autoclave It is subsequently evaporated and the residue is chromatographed on silica gel 8 g of the title compound are obtained as a resin H-4 N-methyl-2-(4.5-dιmethyl-2-o-tolyloxymethylcvclohexa-1 ,4-dιenyl)-2- methoxyiminoacetamide (Comp 3 002) 10 ml of triethylamine solution (5N in methanol) are added to a solution of 2 g of methyl (4,5- dιmethyl-2-o-tolyloxymethylcyclohexa-1 ,4-dιenyl)methoxyιmιnoacetate in 10 ml of methanol The mixture is stirred for 6 hours at approximately 40° It is subsequently evaporated and the residue is chromatographed on silica gel 1 8 g of the title compound are obtained as colourless crystals of m p 96-98° H-5 methyl (2,6-dιmethylmorpholιn-4-yl)-2-methoxyιmιnopent-3-vnoate (cis and trans) 9 g of methyl 2-methoxyιmιnochlorooxalate, 0 1 g of copper(l) iodide and 0 3 g of Pd (TPP) 2 Cl 2 are added to a solution of 7 65 g of 2,6-dιmethyl-4-prop-2-ynylmorpholιne (cis/trans mixture) in 200 ml of triethylamine and 50 ml of THF The mixture is now stirred for 14 hours at 80° It is subsequently filtered with suction and the residue is evaporated The oily residue is chromatographed on silica gel (ether/hexane 1 2) This gives 2 1 g of oil of the title compound (trans) and 4 2 g of oil of the title compound (cis) H-6 methyl f2-(2,6-dιmethylmorpholιn-4-ylmethyl)-4,5-dιmethylcvclohexa-1 ,4-dιenyll- methoxyiminoacetate 7 5 ml of 2,3-dιmethylbuta-1 ,3-dιene are added to a solution of 3 3 g of methyl 5-(2,6- dιmethylmorpholιn-4-yl)-2-methoxyιmιno-pent-3-ynoate (cis) in 5 ml of toluene The reaction mixture is heated for 14 hours at 130° in an autoclave It is subsequently evaporated and the residue is chromatographed on silica gel 2 6 g of the title compound are obtained as resin H-7 methyl 2-methoxyιmιno-5-morpholιn-4-yl-pent-3-vnoate 7 6 g of methyl 2-methoxyιmιnochlorooxylate and 0 1 g of copper(l) iodide and 0 3 g of Pd (TPP) 2 Cl 2 are added to a solution of 6 25 g of 4-prop-2-ynylmorpholιne in 250 ml of triethylamine and 30 ml of THF The mixture is now stirred for 14 hours at 80° It is subsequently filtered off with suction and filtrate is evaporated The oily residue is chromatographed on silica gel (ethyl acetate/hexane 4 1 ) This gives 6 65 g of crystals of the title compound of melting point 43-45° H-8 methyl (4,5-dιmethyl-2-morpholιn-4-ylmethylcvclohexa-1 ,4-dιenyl)methoxyιmιnoacetate 10 ml of 2,3-dιmethylbuta-1 ,3-dιene are added to the solution of 4 8 g of methyl 2- methoxyιmιno-5-morpholιn-4-yl-pent-3-ynoate in 10 ml toluene The reaction mixture is heated for 24 hours at 130° in an autoclave It is subsequently evaporated and the residue is chromatographed on silica gel (ethyl acetate/hexane 1 2) This gives 3 g of crystals of the title compound of melting point 64-66° H-9 Methyl (2-chloromethyl-4,5-dιmethylcyclohexa-1 ,4-dιenyl)methoxyιmιnoacetate 1 4 ml of ethyl chloroformate are added to a solution of 2.3 g methyl (4,5-dιmethyl-2- morpholιn-4-ylmethylcyclohexa-1 ,4-dιenyl)methoxyιmιnoacetate in 25 ml of THF The mixture is now heated for 20 hours at 70° After the mixture has been evaporated, the residue is chromatographed on silica gel (ether/hexane 1 2) This gives 1 5 g of crystals of the title compound of melting point 65-68° H-10 Methyl (2-chloromethyl-4.5-dιmethylcvclohexa-1,4-dιenyl)methoxyιmιnoacetate 1 4 ml of ethyl chloroformate are added to a solution of 2 1 g of methyl [2-(2,6- dιmethylmorpholιn-4-ylmethyl)-4,5-dιmethylcyclohexa-1 ,4-dιenyl]methoxyιmιnoacetate in 25 ml of THF The mixture is now heated for 20 hours at 70° After the mixture has been evaporated, the residue is chromatographed on silica gel (ether/hexane 1 2) This gives 1 2 g of crystals of the title compound of melting point 65-68° H-11 Methyl (4,5-dιmethyl-2-o-tolyloxymethylcvclohexa-1 ,4-dιenyl)methoxyιmιnoacetate 20 g of o-cresol and 40 g of potassium carbonate are added to a solution of 27 5 g of methyl (2-chloromethyl-4,5-dιmethylcyclohexa-1 ,4-dιenyl)methoxyιmιnoacetate The mixture is now heated for 14 hours at 65°, cooled to room temperature and filtered with suction, and the filtrate is evaporated The residue is taken up in 150 ml of ethyl acetate, the mixture is washed with potassium carbonate solution and filtered with suction, and the filtrate is evaporated In this manner, 34 g of the title compound are obtained as a pale brown oil H-12 Methyl 5-chloro-2-methoxyιmιnopent-3-vnoate 1 4 ml of ethyl chloroformate are added to a solution of 12 1 g of methyl 2-methoxyιmιno-5- morpholιn-4-ylpent-3-ynoate in 25 ml of THF The mixture is now heated for 20 hours at 70° After evaporation, the residue is chromatographed on silica gel (ether/hexane 1 2) This gives 8 2 g of colourless crystals of the title compound of melting point 64-67° H-13 methyl 2-methoxyιmιno-5-o-tolyloxypent-3-ynoate 20 g of the sodium salt of o-cresol are added to a solution of 27 5 g of methyl 5-chloro-2- methoxyιmιnopent-3-ynoate in 5 ml of acetonitrile The mixture is now heated for 14 hours at 75°, cooled to room temperature and filtered with suction, and the filtrate is evaporated The residue is taken up in 150 ml of ethyl acetate, the mixture is washed with potassium carbonate solution and filtered with suction, and the filtrate is evaporated This gives 32 g of the title compound as a pale brown oil H-14 methyl (4,5-dιmethyl-2-(2 l ,3'-dιmethyl-4'-(2"-ethoxyethyl)phenyloxymethyl)- cyclohexa-1 ,4-dιenyl)methoxyιmιnoacetate (Comp 6 160) 1 2 g of 2,3-dιmethyl-4-(2-ethoxyethyl)phenol and 1 7 g of potassium carbonate are added to solution of 1 7 g of methyl (2-chloromethyl-4,5-dιmethyl-cyclohexa-1 4-dιenyl)- methoxyiminoacetate in 30 ml acetonitrile and 5 ml of dimethylformamide The mixture is now heated for 14 hours at 90°, cooled to room temperature and filtered with suction, and the filtrate is evaporated The residue is taken up in 150 ml ethyl acetate, the mixture is washed with potassium carbonate solution and filtered with suction, and the filtrate is evaporated After evaporation, the product is chromatographed on silica gel This gives 0 65 g of the title compound as a pale brown oil H-15 Preparation of Compound 6 158 700 mg of potassium carbonate and 900 mg of 4-nιtrophenol are added to a solution of 1 g of methyl (2-chloromethyl-4,5-dιmethylcyclohexa-1 ,4-dιenyl)methoxyιmιnoacetate The mixture is then stirred for 4 hours at 80°, cooled and chromatographed on silica gel (ether/hexane 1 2) This gives 900 mg of crystals of the title compound of m p 128-130° H-16 Preparation of Compound 6 156 17700 mg of potassium carbonate and 22.4 g of 3-iodophenol are added to a solution of 23 1 g of methyl (2-chloromethyl-4,5-dimethylcyclohexa-1 ,4-dienyl)methoxyiminoacetate in 80 ml of DMSO The mixture is then stirred for 4 hours at 80°, cooled and chromatographed on silica gel (ether/hexane 1.2). This gives 34.3 g of crystals of the title compound of m p 92-94° H-17 Preparation of Compound 6.150 700 mg of potassium carbonate and 900 mg of 4-bromo-2-chlorophenol are added to a solution of 1 g of methyl (2-chloromethyl-4,5-dimethylcyclohexa-1 ,4-dιenyl)methoxyιmιno- acetate in 3.5 ml of DMSO. The mixture is then stirred for 4 hours at 80°, cooled and chromatographed on silica gel (ether/hexane 1 :2). This gives 850 mg of crystals of the title compound of m.p 122-127° H-18 Preparation of Compound 28 103 1 4 g of potassium carbonate, 0.83 g of 3-chloro-4-fluorophenylborιc acid and 0.46 g of Pd (PPh) 4 are added to a solution of 1.9 g of compound 6.156 in 16 ml dimethoxyethane, 12 ml of tetrahydrofuran and 16 ml of water under argon The mixture is now stirred for 5 hours at 75°. The reaction mixture is treated with 150 ml of ethyl acetate and the aqueous phase is separated off The ethyl acetate phase is washed twice with water, dried and evaporated, and the residue is chromatographed on silica gel (ether/hexane 1:2). This gives 1.6 g of crystals of the title compound H-19 Preparation of Compound 22.002 700 mg of potassium carbonate and 900 mg of 3-benzyloxyphenol are added to a solution of 1 g of methyl (2-chloromethyl-4,5-dιmethylcyclohexa-1 ,4-dιenyl)methoxyιmιnoacetate in 3 5 ml of DMSO. The mixture is then stirred for 4 hours at 80°, cooled and chromatographed on silica gel (ether/hexane 1.2). This gives 850 mg of crystals of the title compound. H-20 Preparation of Compound 24 003 700 mg of potassium carbonate and 900 mg of 4-phenoxyphenol are added to a solution of 1 g of methyl (2-chloromethyl-4,5-dιmethylcyclohexa-1 ,4-dιenyl)methoxyιmιnoacetate The mixture is then stirred for 4 hours at 80°, cooled and chromatographed on silica gel (ether/hexane 1 2) This gives 850 mg of resinous oil of the title compound H-21 Preparation of Compound 6.168 700 mg of potassium carbonate and 900 mg of 4-phenylphenol are added to a solution of 1 g of methyl (2-chloromethyl-4,5-dιmethyicyclohexa-1 ,4-dιenyl)methoxyιmιnoacetate The mixture is then stirred for 4 hours at 80°, cooled and chromatographed on silica gel (ether/hexane 1 2) This gives 750 mg of resinous oil of the title compound H-22 Preparation of Compound 6 178 0 1 g of Pd (TPP) 2 Cl 2 and 0.3 ml of triethylamine are added to a solution of 1 g starting material in 3 ml of methanol The reaction mixture is now stirred for 6 hours at 60° and poured into 40 ml of water, and this mixture is extracted with twice 20 ml of ether/THF 4 1 After evaporation, the residue is chromatographed on silica gel (ether/hexane 3 1) This gives 0 5 g of product as resinous oil H-23 Preparation of Compound 6 179 0 1 g of Pd/C 10% is added to a solution of 5 g of starting material in 30 ml of tetrahydrofuran The mixture is now hydrogenated until the theoretic amount of hydrogen has been consumed Thereupon, the mixture is filtered with suction, the filtrate is evaporated and the residue is chromatographed on silica gel (ethyl acetate/hexane 1 2) This gives 3 5 g of product as an oil H-24 Preparation of Compound 23 017 700 mg of potassium carbonate and 900 mg of 4-chloronιtrobenzene are added to a solution of 1 g of Compound 6 178 in 3 5 ml of DMSO The mixture is then stirred for 4 hours at 80°, cooled and chromatographed on silica gel (ether/hexane 1 2) This gives 700 mg of resinous oil of the title compound H-25: Preparation of Compound 22.005 700 mg of potassium carbonate and 900 mg of 3-chloromethylbenzotrifluoride are added to a solution of 1 g of Compound 6.178 in 3.5 ml of DMSO. The mixture is then stirred for 4 hours at 80°, cooled and chromatographed on silica gel (ether/hexane 1 :2). This gives 800 mg of resinous oil of the title compound. H-26: Preparation of Compound 19.002 620 mg of phenylacetylene at 0.15 g of Pd (TPP) 2 Cl 2 are added to a solution of 1820 mg of starting material in 1 ml of triethylamine and 7 ml of DMSO. The mixture is now stirred for 3 hours at 65° and filtered with suction, the filtrate is evaporated and the residue is chromatographed on silica gel (ether/hexane 1:2). This gives 1540 mg of product as crystals of melting point 98-101 °. H-27- Preparation of Compound 20.002 100 mg of Pd/C (5%) are added to a solution of 1.8 g of Compound 19.002 in 30 ml of tetrahydrofuran. The mixture is now hydrogenated until the theoretic amount of hydrogen has been consumed and then filtered with suction, the filtrate is evaporated and the residue is chromatographed on silica gel (ethyl acetate/hexane 1 :2). This gives 1.5 g of product as an oil. H-28: Preparation of Compound 21.002 100 mg of Pd/C (5%) are added to a solution of 1.5 g of Compound 19.002 in 30 ml of tetrahydrofuran. The mixture is now hydrogenated until the theoretic amount of hydrogen has been consumed and then filtered with suction, the filtrate is evaporated and the residue is chromatographed on silica gel (ethyl acetate/hexane 1 :2). This gives 1.2 g of product as an oil H-29 Preparation of Compound 23.009 700 mg of potassium carbonate and 900 mg of 2-nitro-5-fluorobenzonitrile are added to a solution of 1 g of Compound 6.178 in 3.5 ml of DMSO. The mixture is then stirred for 4 hours at 80°, cooled and chromatographed on silica gel (ether/hexane 1 :2). This gives 900 mg of resinous oil of the title compound. Table 1 H H H H H H H H H H 4-Me 4-Et H H H H H 1 67 CH, CH, H H H 4- H Comp. R 2 , R 22 R 8 R 9 D, D 2 D 3 Physical No. data 1.68 CH, CH, H H H 1.71 CH 3 CH 3 H H H ^ C 6 H s -4-CI H NOCH 3 1 .72 CH 3 CH 3 H H H 4- C 6 H,-4-phenoxy NOCH, 1.73 CH 3 CH 3 H H H 4- H C 6 H 4 -4-(4-chlorop enoxy) -^^NOCH j 1.74 CH 3 CH 3 H H H 4- H C 6 H 4 -4-(4-chloropheπoxy) -^^NOC j H j 1.75 H CH, H H 3-CH, H H 3- NOCH, 1.117 H H H H H 1.118 H H H H H 1 121 Cl CH, H H H C 6 H 5 -4-CI H NOCH, 1 122 CH, Cl H H H H 1 123 CH, Cl H H H H C 6 H 4 - -(4-chlorophenoxy) ~ NOCH, 1 124 Me Me H H H 4- H -4-0CH j -C 6 H,-3-CF 3 C 6 H 4 ,θ . N 1 125 Me Me H H H 4- H - -OCH r -C 6 H 4 -4-CF., C 6 H 4 N 1 126 Me Me H H H 4- H -4-OCH 2 -C 6 H 4 -2-CF 3 C 6 H 4 ,θ . N 1 127 Me Me H H 2-CH=CH2 3-CH=CH- H 1 128 Me Me H H 2-Me 3-CH ? -CH=CH, 4-OMe Table 2 Compounds of the formula in which R 21 r R 22 , R 8l R 9 , D,, D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Physical data of exemplary compounds" Comp R 21 R 22 R R D, D, D 3 Physical data No 2.02 CH, CH, H H 2-CH, H H oil Table 3 Compounds of the formula in which R 21 , R 22 , D,, D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Physical data of exemplary compounds Comp R 21 R 22 R 8 R q D, D, D 3 Physical data No 3 02 CH, CH, H H 2-CH, H H 96-98° Table 4 Compounds of the formula in which R 21 , R 22 , D 1 f D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Table 5 Compounds of the formula in which R 21 , R 22 , D,, D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Table 6 Compounds of the formula in which R 21 , R 22 , R B , R 9 , D,, D 2 und D 3 have the meanings of the corresponding compounds of Table 1 Physical data of exemplary compounds No 6 10 CH 3 CH 3 H H 2-ι-prop 5-CH 3 6 14 CH 3 CH 3 H H 2-CI H 6.18 CH, CH, H H 2-CH 3 4-CI Table 7 Compounds of the formula in which R 21 , R 22 , R B , R 9 , D,, D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Physical data of exemplary compounds Comp R 21 R 22 Rπ R 9 D, D 2 No 7 16 CH 3 CH 3 H H 4-CI H Table 8 Compounds of the formula in which R 21 , R 22 , D,, D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Table 9 Compounds of the formula in which R 2) , R 22 , D,, D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Table 10 Compounds of the formula in which R 21 , R 22 , D,, D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Table 11 Compounds of the formula in which R 2) , R 22 , R a , R 9l D,, D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Physical data of exemplary compounds' Comp R 2 , \ 22 R 8 R, D, D, D 3 Physical data No 1 1 140 H CH, H H H 2-CH, H oi! Table 12 Compounds of the formula in which R 21 , R 22 , R 8 , R 9 , D l f D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Table 13 Compounds of the formula in which R 21 , R 22 , D,, D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Table 14 Compounds of the formula in which R 2 ,, R 22 , D,, D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Table 15 Compounds of the formula in which R 21 , R 22l D,, D 2 and D 3 have the meanings of the corresponding compounds of Table 1 Table 16 (intermediates) Comp D, D, Physical No data H H H H resin H H H H H H H 4-Me 4-Et H H H H H H H H H H NOCH, 16.71. CH O OCH3 H 4- e H 5 -4-CI NOCH, 16 72 CH O OCH3 4_ 16 73 N O OCH3 H H C 6 H 4 -4-(4-chlorophenoxy) - NOCH, 16 74 N O OCH3 H H C β H 4 -4-(4-chlorophenoxy) -^^NOC j H j -I6 75 CH S OCH3 ,-4-OCH.-C,H 4 -3-CF, H N 16 76 N O OCH3 -4-OCH 2 -C 6 H 4 -4-CF 3 H / O. / ■ N 16 77 N SO OCH3 / ^-OCH 2 -C 6 H 4 -2-CF 3 H 4- C 6 H 4 O. ^ N 17 71 O OCH3 O H 4 A - 17 72 O OCH3 4- 17 73 O OCH3 H C 6 H 4 -4-(4-c lorophenoxy) NOCH j 17 74 O OCH3 NHCH, H C 6 H 4 -4-(4-chlorop enoxy) H / ^NOC 2 H 5 17 75 S OCH3 NHBz H / -4-OCH 2 -C 6 H 4 -3-CF 3 17 76 0 OCH3 NHB 17 77 SO OCH3 o 17.78 O OCH3 o 17.81 SO OCH3 s Table 18 (intermediates) 3- 18.67 CH 3 CH, SCH3 H H 3- 4- Table 19 Comp W Physical data No 3-C 6 H 4 -C=C-C 6 H 3 Cl2(2',4') 3-C6H 4 -C≡C-C6iT5 98-101 ' 3-C 6 H 4 -C-.C-C 6 H 4 (OCH 3 )(4') 3-C 6 H 4 -C ≡ C-C 6 H 3 (CF 3 )(3' ? 5') 3-C 6 H 4 -C ≡ C-C 6 H 4 (CF 3 )(3') 3-C 6 H 4 -C 3 C-CO-C 6 H 4 (CF 3 )(3') 3-C 6 H 4 -C≡C-CO-C 6 H 5 3-C 6 H 4 -C≡C-CO-C 6 H 4 (CI)(3') 3-C 6 H 4 -C≡C-C≡C-C 3 H 7 (ι) 3-C 6 H 4 -C≡C-C≡C-C(CH3) 2 -OH 3-C 6 H 4 -(C≡C) 2 -C(CH 3 ) 2 -OCOCH3 3-C 6 H 4 -C≡C-C(CH 3 ) 2 -OH 3-C 6 H 4 -C≡C-pyrazιnyl(2') 3-C 6 H 4 -C≡C-pyridyl(3') 3-C 6 H 4 -C≡C-CO-pyπdyl(3') 3-C 6 H 4 -C≡C-pyridyl(2') 3-C 6 H 4 -C≡C-pyridyl(4') 3-C 6 H 4 -C ≡ C-C 6 H 4 (CF 3 )(4') 3-C 6 H 4 -C≡C-C 6 H 4 (CI)(4') 3-C 6 H 4 -C≡C-CH 2 -OH 3-C 6 H 4 -C=C-pyπmιdιnyl(2') 3-C 6 H 4 -CsC-pyπmιdιnyl(4') 3-C 6 H 4 -C≡C-pyπmιdιnyl(5') 3-C 6 H 4 -CsC-l 3-CgH 4 -C=C-CH3 3-C 6 H 4 -C≡C-Br 3-C 6 H 4 -C ≡ C-C 6 H 4 (Br)(4') 3-C 6 H 4 -C S C-C 6 H 3 (OCH3)3(3 , ,4',5') 3-C 6 H 4 -C≡C-thιazolyl(2') 3-C 6 H 4 -C≡C-oxazolyl(2') 3-C 6 H 4 -C≡C-thιenyl(2') 3-C 6 H 4 -C≡C-thιenyl(3') 3-C 6 H 4 -C=C-Et 4-C 6 H 4 -C≡C-H 2-C 6 H 4 -C≡C-H 4-C 6 H 4 -C=C-CH 3 2-C 6 H 4 -C≡C-Br 2-C 6 H 4 -C≡C-C(CH 3 ) 2 -OH 4-C 6 H 4 -C--C-C(CH3)2-OH 3-C 6 H 4 -C≡C-CF 3 3-C 6 H 4 -C≡C-COOEt 3-C 6 H 4 -C≡C-COOMe 2-C 6 H 4 -C≡C-C(CH 3 ) 2 -OH 3-C 6 H 4 -C≡C-C(CH 3 )2-0-CH 3 4-C 6 H 4 -C≡C-C(CH 3 )2-0-CH 3 3-C 6 H 4 -C≡C-CH 2 -OMe 3-C 6 H 4 -C≡C-C 4 H 9 (n) 3-C 6 H 4 -C≡C-C 3 H 7 (n) 3-C 6 H 4 -C≡C-C 8 H 17 (n) 3-C 6 H 4 -C ≡ C-C 6 H 3 CI 2 (2',4') 3-CβH 4 -C≡C-C6H5 3-C 6 H 4 -C ≡ C-C 6 H 4 (OCH 3 )(4') 3-C 6 H 4 -C ≡ C-C 6 H3(CF 3 )(3 , ,5') 3-C 6 H 4 -C ≡ C-C 6 H 4 (CF 3 )(3') 3-C 6 H 4 -C≡C-C0-C 6 H 4 (CF 3 )(3') 3-C 6 H 4 -CE=C-CO-C 6 H 5 oil oil oil Table 19a Compounds of the formula in which Z and W have the meanings of the corresponding compounds of Table 19 Table 20 Comp W Physical data No 20 001 OMe 3-C 6 H 4 -CH= CH-C 6 H 3 Cl2(2',4 , ) 20 002 OMe 3-C 6 H 4 -CH= CH-CgHs 20 003 OMe 3-CgH 4 -CH : CH-C 6 H 4 (0CH3)(4') 20 004 OMe 3-CgH -CH : CH-C 6 H 3 (CF3)(3 , ,5') 20 005 OMe 3-CgH 4 -CH : CH-C 6 H 4 (CF 3 )(3') 20 006 OMe 3-CgH 4 -CH : CH-CO-C 6 H 4 (CF3)(3') 20 007 OMe 3-CgH -CH : CH-CO-C 6 H 5 20.008 OMe 3-CgH 4 -CH : CH-CO-C 6 H 4 (CI)(3') 20 009 OMe 3-CgH -CH : CH-C(CH 3 ) 2 -OH 20 010 OMe 3-CgH 4 -CH : OH-pyrazιnyl(2') 20 011 OMe 3-CgH 4 -CH : H-pyπdyl(3') 20 012 OMe 3-CgH 4 -CH : : CH-CO-pyrιdyl(3') 20 013 OMe 3-CgH 4 -CH : =CH-pyπdyl(2') 20 014 OMe 3-CgH -CH : =CH-pyπdyl(4') 20 015 OMe 3-CgH 4 -CH : : CH-C 6 H 4 (CF 3 )(4') 20 016 OMe 3-CgH -CH : :CH-C 6 H 4 (CI)(4 , ) 20 017 OMe 3-CgH -CH : =CH-CH 2 -OH 20 018 OMe 3-CgH 4 -CH : : CH-pyrιmιdιnyl(2') 20 019 OMe 3-CgH 4 -CH =CH-pyrιmιdιnyl(4') 20 020 OMe 3-CgH -CH =CH-pyπmιdιnyl(5') 20 021 OMe 3-CgH 4 -CH =CH-I 20 022 OMe 3-CgH 4 -CH =CH-CH 3 20 023 OMe 3-C 6 H 4 -CH=CH-Br 20 024 OMe 3-C 6 H 4 -CH=CH-C 6 H 4 (Br)(4') 20 025 OMe 3-C 6 H 4 -CH=CH-C 6 H 2 (OCH 3 ) 3 (3 , ,4',5') 20 026 OMe 3-C 6 H 4 -CH=CH-C 6 H 3 (CH 3 ) 2 (3 , ,5') 20 027 OMe 3-C 6 H 4 -CH=CH-thιazolyl(2') 20 028 OMe 3-C 6 H -CH=CH-oxazolyl(2') 20 029 OMe 3-C 6 H 4 -CH=CH-thιenyl(2') 20 030 OMe 3-C 6 H 4 -CH=CH-thιenyl(3') 20 031 OMe 3-C 6 H 4 -CH=CH-Et 20 032 OMe 4-C 6 H 4 -CH=CH2 20 033 OMe 2-C 6 H 4 -CH=CH2 20 034 OMe 4-C 6 H 4 -CH=CH-CH 3 20 035 OMe 2-C 6 H 4 -CH=CH-Br 20 036 OMe 2-C 6 H 4 -CH=CH-C(CH 3 ) 2 -OH 20 037 OMe 4-C 6 H 4 -CH=CH-(CH 3 ) 2 -OH 20 038 OMe 3-C 6 H 4 -CH=CH-CF 3 20 039 OMe 3-C 6 H 4 -CH=CH-COOEt 20 040 OMe 3-C 6 H 4 -CH=CH-COOMe 20 041 OMe 2-C 6 H 4 -CH=CH-C(CH 3 ) 2 -OH 20 042 OMe 3-CgH 4 -CH=CH-C(CH 3 ) 2 -0-CH 3 20 043 OMe 4-C 6 H 4 -CH=CH-C(CH 3 ) 2 -0-CH 3 20 044 OMe 3-C 6 H 4 -CH=CH-CH 2 -OMe 20 045 OMe 3-C 6 H 4 -CH=CH-C 4 H 9 (n) 20 046 OMe 3-C 6 H 4 -CH=CH-C 3 H 7 (n) 20 047 OMe 3-C 6 H 4 -CH=CH-C 8 H 17 (n) 20 048 NHMe 3-C 6 H 4 -CH=CH-C 6 H 3 Cl 2 (2 , 1 ') 20 049 NHMe 3-C 6 H 4 -CH=CH-C 6 H 5 20 050 NHMe 3-C 6 H 4 -CH=CH-C 6 H 4 (OCH 3 )(4') 20 051 NHMe 3-C 6 H 4 -CH=CH-C 6 H 3 (CF 3 ) 2 (3 , ,5') 20 052 NHMe 3-C 6 H 4 -CH=CH-C 6 H 4 (CF 3 )(3') 20 053 NHMe 3-C 6 H 4 -CH=CH-CO-C 6 H 4 (CF 3 )(3') 20 054 NHMe 3-C 6 H 4 -CH=CH-CO-C 6 H 5 20 055 NHMe 3-C 6 H 4 -CH=CH-CO-C 6 H 4 (CI)(3') 20 056 NHMe 3-C 6 H 4 -CH=CH-C(CH 3 ) 2 -OH 20 057 NHMe 3-C 6 H 4 -CH=CH-pyrazιnyl(2 , ) 20 058 NHMe 3-C 6 H 4 -CH=CH-pyπdyl(3') 20.059 NHMe 3-C 6 H 4 -CH=CH-CO-pyridyl(3') 20.060 NHMe 3-C 6 H 4 -CH=CH-pyhdyl(2') 20.061 NHMe 3-C 6 H 4 -CH=CH-pyridyl(4') 20 062 NHMe 3-C 6 H 4 -CH=CH-C 6 H 4 (CF 3 )(4') 20.063. NHMe 3-C 6 H 4 -CH=CH-C 6 H 4 (CI)(4') 20.064 NHMe 3-C 6 H 4 -CH=CH-CH 2 -OH 20.065. NHMe 3-C 6 H 4 -CH=CH-pyrimidinyl(2') 20.066 NHMe 3-C 6 H 4 -CH=CH-pyrimidinyl(4') 20.067 NHMe 3-C 6 H 4 -CH=CH-pyrimidιnyl(5') 20.068 NHMe 3-C 6 H 4 -CH=CH-l 20.069 NHMe 3-C 6 H 4 -CH=CH-CH 3 20.070 NHMe 3-C 6 H 4 -CH=CH-Br 20.071 NHMe 3-C 6 H 4 -CH=CH-C 6 H 4 (Br)(4') 20.072. NHMe 3-C 6 4 -Cr\=Cr -C 6 r\ 2 (OCr\ 2 (3' A' ,5') 20.074. NHMe 3-C 6 H 4 -CH=CH-thιazolyl(2') 20.075 NHMe 3-C 6 H 4 -CH=CH-oxazolyl(2') 20.076 NHMe 3-C 6 H 4 -CH=CH-thienyl(2') 20.077 NHMe 3-C 6 H 4 -CH=CH-thienyl(3') 20.078 NHMe 3-C 6 H 4 -CH=CH-Et 20.079. NHMe 4-C 6 H 4 -CH=CH2 20.080 NHMe 2-C 6 H 4 -CH=CH2 20.081 NHMe 4-C 6 H 4 -CH=CH-CH 3 20.082 NHMe 2-C 6 H 4 -CH=CH-Br 20.083. NHMe 2-C 6 H 4 -CH=CH-C(CH 3 ) 2 -OH 20.084 NHMe 4-C 6 H 4 -CH=CH-C(CH 3 ) 2 -OH 20.085. NHMe 3-C 6 H 4 -CH=CH-CF 3 20.086. NHMe 3-C 6 H 4 -CH=CH-COOEt 20.087 NHMe 3-C 6 H 4 -CH=CH-COOMe 20.088 NHMe 2-C 6 H 4 -CH=CH-C(CH 3 ) 2 -OH 20.089 NHMe 3-C 6 H 4 -CH=CH-C(CH 3 ) 2 -0-CH 3 20.090. NHMe 4-C 6 H 4 -CH=CH-C(CH 3 ) 2 -O-CH 3 20.091 NHMe 3-C 6 H 4 -CH=CH-CH 2 -OMe 20 092. NHMe 3-C 6 H 4 -CH=CH-C 4 H 9 (n) 20.093 NHMe 3-C 6 H 4 -CH=CH-C 3 H 7 (n) 20.094 NHMe 3-C 6 H 4 -CH=CH-C 8 H 17 (n) -C 6 H 4 (CH 3 )(3') ■ CH 2 -morpholιnyl(1 ) • CH 2 -pιpeπdιnyl(1 ) ■ CH 2 -CI •C 6 H 4 (CH 3 )(3') •CHs-O-CgH^CI;,)^^) • CH 2 -0-C 6 H 4 (CH3)(3') Compounds of the formula in which Z and W have the meanings of the corresponding compounds of Table 20 Table 21 Comp Z W Physical data No. 3-CgH 4 -CH2-CH2-C 6 H3Cl2(2',4') 3-C H 4 -CH2-CH2-C H5 3-C 6 H 4 -CH2-CH2-C 6 H 4 (OCH3)(4') 3-C 6 H 4 -CH2-CH2-CgH 3 (CF3)(3\5') 3-C 6 H 4 -CH 2 -CH2-C 6 H 4 (CF 3 )(3') 3-C 6 H 4 -CH 2 -CH2-CO-C 6 H 4 (CF3)(3') 3-C H 4 -CH2 _ CH2"CO-CgH5 3-C 6 H 4 -CH 2 -CH 2 -CO-C 6 H 4 (CI)(3') 3-C 6 H 4 -CH 2 -CH 2 -C(CH 3 ) 2 -OH 3-C 6 H 4 -CH 2 -CH 2 -pyrazιnyl(2') 3-C 6 H 4 -CH2-CH2-pyridyl(3') 3-C 6 H 4 -CH 2 -CH 2 -CO-pyridyl(3 ) 3-C 6 H 4 -CH2-CH 2 -pyridyl(2') 3-C 6 H 4 -CH 2 -CH 2 -pyrιdyl(4') 3-C 6 H 4 -CH 2 -CH 2 -C6H 4 (CF 3 )(4') 3-C 6 H 4 -CH2-CH2-C 6 H 4 (CI)(4 , ) 3-C6H 4 -CH 2 -CH 2 -CH 2 -OH 3-C 6 H 4 -CH 2 -CH 2 -pyrιmιdinyl(2') 3-C 6 H -CH 2 -CH 2 -pyrimιdιnyl(4') 3-C 6 H 4 -CH 2 -CH 2 -pyπmidιnyl(5') 3-CgH 4 -CH 2 -CH 2 -l 3-CgH 4 -CH -CH 2 -CH 3 3-C 6 H 4 -CH 2 -CH 2 -Br 3-C 6 H 4 -CH 2 -CH2-C 6 H 4 (Br)(4 , ) 21 025 OMe 3-CgH 4 - ■ CH 2 -CH 2 -C 6 H 2 (OCH 3 )3(3' 4 , ,5') 21 026 OMe 3-C 6 H 4 - •CH 2 -CH 2 -C 6 H 3 (CH 3 ) 2 (3\5') 21 027 OMe 3-CgH 4 - CH 2 -CH 2 -thιazolyl(2') 21 028 OMe 3-C 6 H 4 - CH 2 -CH 2 -oxazolyl(2') 21 029 OMe 3-CgH 4 - CH 2 -CH 2 -thιenyl(2') 21 030 OMe 3-CgH 4 - CH 2 -CH 2 -thιenyl(3') 21 031 OMe 3-C 6 H 4 - CH 2 -CH 2 -Et 21 032 OMe 4-C 6 H 4 - CH2"CH 3 21 033 OMe 2-C 6 H 4 - CH2"CH 3 21 034 OMe 4-C 6 H 4 - CH2-CH2~CH 3 21 035 OMe 2-C 6 H 4 - CH 2 -CH 2 -Br 21 036 OMe 2-C 6 H 4 - CH 2 -CH 2 -C(CH 3 ) 2 -OH 21 037 OMe 4-C 6 H 4 - CH 2 -CH 2 -(CH 3 ) 2 -OH 21 038 OMe 3-CgH 4 - CH -CH 2 -CF 3 21 039 OMe 3-C 6 H 4 - CH 2 -CH 2 -COOEt 21 040 OMe 3-CgH - CH 2 -CH 2 -COOMe 21 041 OMe 2-C 6 H 4 - CH 2 -CH 2 -C(CH 3 ) 2 -OH 21 042 OMe 3-CgH 4 - CH 2 -CH 2 -C(CH 3 ) 2 -0-CH 3 21 043 OMe 4-C 6 H 4 - CH2-CH 2 -C(CH 3 ) 2 -0-CH 3 21 044 OMe 3-CgH 4 - CH 2 -CH 2 -CH 2 -OMe 21 045 OMe 3-C 6 H 4 - CH 2 -CH 2 -C 4 H 9 (n) 21 046 OMe 3-CgH - CH 2 -CH 2 -C 3 H 7 (n) 21 047 OMe 3-CgH - CH2-CH 2 -C 8 H 17 (n) 21 048 NHMe 3-CgH 4 - CH2-CH 2 -C6H3Cl2(2 , ,4') 21 049 NHMe 3-CgH - CH2 _ CH 2 -CgH 5 21 050 NHMe 3-CgH 4 - CH 2 -CH 2 -C 6 H 4 (OCH3)(4') 21 051 NHMe 3-CgH 4 - CH 2 -CH2-C 6 H3(CF 3 ) 2 (3 , ,5') 21 052 NHMe 3-CgH 4 - CH 2 -CH 2 -CgH 4 (CF 3 )(3') 21 053 NHMe 3-CgH 4 - CH 2 -CH 2 -CO-C 6 H 4 (CF 3 )(3') 21 054 NHMe 3-CgH 4 - CH 2 -CH 2 -CO-CgH5 21 055 NHMe 3-CgH 4 - CH 2 -CH 2 -CO-C 6 H 4 (CI)(3') 21 056 NHMe 3-CgH 4 - CH 2 -CH 2 -C(CH 3 )2-OH 21 057 NHMe 3-CgH 4 - CH 2 -CH 2 -pyrazιnyl(2') 21 058 NHMe 3-CgH 4 - CH 2 -CH 2 -pyrιdyl(3') 21 059 NHMe 3-CgH 4 - CH 2 -CH 2 -CO-pyrιdyl(3') 21 060 NHMe 3-CgH 4 - CH 2 -CH 2 -pyrιdyl(2') 21 061 NHMe 3-C 6 H 4 -CH 2 -CH 2 -pyridyl(4') 21 062 NHMe 3-C 6 H 4 -CH 2 -CH 2 -C 6 H 4 (CF 3 )(4') 21 063 NHMe 3-C 6 H 4 -CH 2 -CH 2 -C 6 H 4 (CI)(4') 21 064 NHMe 3-C 6 H 4 -CH 2 -CH 2 -CH 2 -OH 21 065 NHMe 3-C 6 H 4 -CH 2 -CH 2 -pyrιmιdιnyl(2') 21 066 NHMe 3-CgH 4 -CH 2 -CH 2 -pyrιmιdιnyl(4') 21 067 NHMe 3-C 6 H 4 -CH 2 -CH 2 -pyrιmιdιnyl(5') 21 068 NHMe 3-C 6 H 4 -CH 2 -CH 2 -l 21 069 NHMe 3-C 6 H 4 -CH 2 -CH 2 -CH 3 21 070 NHMe 3-C 6 H 4 -CH 2 -CH 2 -Br 21 071 NHMe 3-C 6 H 4 -CH 2 -CH 2 -C 6 H 4 (Br)(4') 21 072 NHMe 3-C 6 H 4 -CH 2 -CH 2 -C 6 H 2 (OCH 3 ) 3 (3',4',5') 21 073 NHMe 3-C 6 H 4 -CH 2 -CH 2 -C 6 H 3 (CH 3 ) 2 (3',5') 21 074 NHMe 3-C 6 H 4 -CH 2 -CH 2 -thιazolyl(2') 21 075 NHMe 3-C 6 H 4 -CH 2 -CH 2 -oxazolyl(2') 21 076 NHMe 3-C 6 H 4 -CH 2 -CH 2 -thιenyl(2') 21 077 NHMe 3-C 6 H 4 -CH 2 -CH 2 -thιenyl(3') 21 078 NHMe 3-C 6 H 4 -CH 2 -CH 2 -Et 21 079 NHMe 4-C 6 H 4 -CH 2 -CH 3 21 080 NHMe 2-C 6 H 4 -CH 2 -CH 3 21 081 NHMe 4-C 6 H 4 -CH 2 -CH 2 -CH 3 21 082 NHMe 2-C 6 H 4 -CH 2 -CH 2 -Br 21 083 NHMe 2-CgH 4 -CH 2 -CH 2 -C(CH 3 ) 2 -OH 21 084 NHMe 4-C 6 H 4 -CH 2 -CH 2 -C(CH 3 ) 2 -OH 21 085 NHMe 3-C 6 H 4 -CH 2 -CH 2 -CF 3 21 086 NHMe 3-C 6 H 4 -CH 2 -CH 2 -COOEt 21 087 NHMe 3-C 6 H 4 -CH 2 -CH 2 -COOMe 21 088 NHMe 2-C 6 H 4 -CH 2 -CH 2 -C(CH 3 ) 2 -OH 21 089 NHMe 3-C 6 H 4 -CH 2 -CH 2 -C(CH 3 ) 2 -0-CH 3 21 090 NHMe 4-C 6 H 4 -CH 2 -CH 2 -C(CH 3 ) 2 -0-CH 3 21 091 NHMe 3-C 6 H 4 -CH 2 -CH 2 -CH 2 -OMe 21 092 NHMe 3-C 6 H 4 -CH 2 -CH 2 -C 4 H 9 (n) 21 093 NHMe 3-C 6 H 4 -CH 2 -CH 2 -C 3 H 7 (n) 21 094 NHMe 3-C 6 H 4 -CH 2 -CH 2 -C 8 H 17 (n) 21 095 NHMe 3-C 6 H 4 -CH 2 -CH 2 -C 6 H 4 (CH 3 )(3') 21 096 NHMe 3-C 6 H 4 -CH 2 -CH 2 -CH 2 -morpholιnyl(1 ) 3-C 6 H 4 -CH 2 -CH 2 -CH 2 -piperidinyl(1) 3-CgH 4 -CH 2 -CH -CH 2 -CI 3-C 6 H 4 -CH 2 -CH 2 -C 6 H 4 (CH 3 )(3 • ) 3-C 6 H 4 -CH 2 -CH 2 -CH 2 -0-C 6 H 3 (CI 2 )(2 , ,4') 3-C 6 H 4 -CH 2 -CH 2 -CH 2 -0-C 6 H 4 (CH 3 )(2') 3-C 6 H 4 -CH 2 -CH 2 -CH 2 -O-C 6 H 4 (CH 3 )(3') Compounds of the formula in which Z and W have the meanings of the corresponding compounds of Table 20. Table 22 CH, Comp W Physical data No. 3-C 6 H 4 -0-CH 2 -C 6 H 3 CI 2 (2',4') 3-CgH -0-CH 2 -CgH5 3-C 6 H 4 -0-CH 2 -C 6 H 4 (OCH 3 )(4') 3-C 6 H 4 -0-CH2-CgH3(CF 3 )(3' 1 5') 3-C 6 H 4 -0-CH 2 -C6H 4 (CF3)(3') 3-C 6 H 4 -0-CH2-CO-C 6 H 4 (CF3)(3') 3-C 6 H 4 -0-CH 2 -CO-C 6 H 5 3-C 6 H 4 -0-CH 2 -CO-C 6 H 4 (CI)(3') 3-C 6 H 4 -0-CH 2 -C(CH 3 ) 2 -OH 3-C 6 H 4 -0-CH 2 -pyrazιnyl(2') 3-C 6 H 4 -0-CH 2 -pyridyl(3') 3-C 6 H 4 -0-CH 2 -CO-pyridyl(3') 3-C6H 4 -0-CH 2 -ρyridyl(2') 3-C 6 H 4 -0-CH 2 -pyridyl(4') 3-C 6 H 4 -0-CH 2 -C 6 H 4 (CF 3 )(4') 3-C 6 H 4 -0-CH2-C 6 H 4 (CI)(4') 3-C 6 H 4 -0-CH 2 -CH 2 -OH 3-C 6 H 4 -0-CH 2 -pyrimidιnyl(2') 3-C 6 H 4 -0-CH2-pyrimιdιnyl(4') 3-C 6 H -0-CH 2 -pyrimιdιnyl(5') 3-C 6 H 4 -0-CH 2 -l 3-C 6 H 4 -0-CH 2 -CH 3 3-C 6 H 4 -0-CH 2 -Br 3-C 6 H 4 -0-CH 2 -C 6 H 4 (Br)(4') 3-C 6 H 4 -0-CH 2 -pyndyl(4') 3-CgH 4 -0-CH 2 -C 6 H 4 (CF 3 )(4') 3-CgH 4 -0-CH 2 -C 6 H 4 (CI)(4') 3-C 6 H 4 -0-CH 2 -CH 2 -OH 3-C 6 H -0-CH 2 -pyπmιdιnyl(2') 3-C 6 H 4 -0-CH 2 -pyrιmιdιnyl(4') 3-CgH 4 -0-CH 2 -pyrιmιdιnyl(5') 3-C 6 H 4 -0-CH 2 -l 3-C 6 H 4 -0-CH 2 -CH 3 3-C 6 H 4 -0-CH 2 -Br 3-C 6 H 4 -0-CH 2 -CgH 4 (Br)(4') 3-CgH 4 -0-CH 2 -C 6 H 2 (OCH 3 ) 3 (3',4\5') 3-C 6 H 4 -0-CH 2 -thιazolyl(2') 3-C 6 H 4 -0-CH 2 -oxazolyl(2') 3-C 6 H 4 -0-CH 2 -thienyl(2') 3-C 6 H 4 -0-CH 2 -thienyl(3') 3-C 6 H 4 -0-CH 2 -Et 4-C 6 H 4 -0-CH 3 2-C 6 H 4 -0-CH 3 4-C 6 H 4 -0-CH 2 -CH 3 2-C 6 H 4 -0-CH 2 -Br 2-C 6 H 4 -0-CH 2 -C(CH 3 ) 2 -OH 4-C 6 H 4 -O-CH 2 -C(CH 3 ) 2 -OH 3-C 6 H 4 -0-CH 2 -CF 3 3-C 6 H 4 -0-CH 2 -COOEt 3-C 6 H 4 -0-CH 2 -COOMe 2-CgH 4 -0-CH 2 -C(CH 3 ) 2 -OH 3-C 6 H 4 -0-CH 2 -C(CH 3 ) 2 -0-CH 3 4-C 6 H 4 -0-CH 2 -C(CH 3 ) 2 -0-CH 3 3-C 6 H 4 -0-CH 2 -CH 2 -OMe 3-C 6 H 4 -0-CH 2 -C 4 H 9 (n) 3-C 6 H 4 -0-CH 2 -C 3 H 7 (n) 3-C 6 H 4 -0-CH 2 -C 8 H 17 (n) 3-C 6 H 4 -0-CH 2 -CH 2 -morpholιnyl(1 ) •0-CH 2 -CH 2 -pιpeπdιnyl( 1 ) ■0-CH 2 -CH 2 -CI •0-CH 2 -C 6 H 4 (CH3)(3') ■ 0-CH2-CH2-0-C 6 H3(Cl2)(2 , ,4') ■ 0-CH2-CH2-0-C 6 H 4 (CH3)(2') ■ 0-CH2-CH2-0-CgH4(CH3)(3') 0-C 6 H 2 CN(2')(CH 3 )2(4',5') resin -CH 2 -CsC-C H5 oil ■ 0-CH 2 -C 3 C-C 6 H 4 (CH 3 )(3') oil ■ 0-CH2-CH2-CH2 _ C H5 oil resin ■ 0-CH2-pyrιdιn-5'-yl(CI)(2') ■ 0-CH 2 -thιazol-5'-yl(CI)(2') ■0-CH 2 -thiazol-5'-yl ■ O-CH 2 -thiadιazol-5'-yl ■0-CH 2 -C6H 4 N02(2') ■0-CH 2 -C 6 H 4 N0 2 (4') ■0-CH 2 -C 6 H 4 CI{2') •0-CH 2 -C6H 3 (CH 3 ) 2 (3',4 * ) ■ 0-CH 2 -C 6 H 4 CF 3 (2') ■ O-CH2-(3',4'-dιmethylcyclohexa-1 ,4-dιenyl) resin Compounds of the formula CH- in which Z and W have the meanings of the corresponding compounds of Table 22 Table 23 - W CH, Comp W Physical data No 3-C 6 H 4 -0-CgH 5 3-C 6 H 4 -0-C 6 H 4 (OCH 3 )(4') 3-C 6 H 4 -0-CgH 4 (CF 3 )(3') 3-C 6 H 4 -0-C0-C 6 H 4 (CF 3 )(3') 3-C 6 H 4 -0-CO-C 6 H 5 3-C 6 H 4 -0-CO-C 6 H 4 (CI)(3') 3-C 6 H 4 -0-C 6 H 3 (CN)(3')(N0 2 )(4') 3-C 6 H 4 -0-pyrazιnyl(2') 3-C 6 H 4 -0-pyπdyl(3') 3-C 6 H 4 -0-C0-pyridyl(3') 3-C 6 H 4 -0-pyrιdyl(2') 3-C 6 H 4 -0-C 6 H 4 (CF 3 )(4') 3-C 6 H 4 -0-C 6 H 4 (CI)(4') 3-C 6 H 4 -0-C 6 H 4 (N0 2 )(4') 3-CgH 4 -0-pyπmιdιnyl(2') 3-C 6 H 4 -0-pyrιmιdιnyl(4') 3-C 6 H 4 -0-pyrιmιdιnyl(5') 3-C 6 H 4 -0-CO-NH-C 6 H 4 (OMe)(4') 3-C 6 H 4 -0-CH 3 3-C 6 H 4 -0-CO-NH-C 6 H 4 (CF 3 )(3') 3-C 6 H 4 -0-C 6 H 4 (Br)(4') 3-C 6 H 4 -0-pyridyl(4') 3-C 6 H 4 -0-C 6 H 4 (CF 3 )(4') 3-CgH 4 -0-C 6 H 4 (CI)(4') 3-C 6 H 4 -0-C0-NH-C 6 H 3 -(Me)(2')(Et)(6') 3-C 6 H 4 -0-pyrιmidinyl(2') 3-C 6 H4-O-pyrimidinyl(4') 3-C 6 H 4 -0-pyrιmιdinyl(5') 3-C 6 H 4 -0-C0-NH-C 6 H 3 -(Me) 2 (2\4') 3-C 6 H 4 -0-CH 3 3-C 6 H 4 -0-C0-NH-C6H 4 -(CI)(3') 3-C 6 H 4 -0-C 6 H 4 (Br)(4") 3-C 6 H 4 -0-C 6 H 2 (OCH 3 ) 3 (3',4',5') 3-C 6 H 4 -0-thιazolyl(2') 3-C 6 H 4 -0-oxazolyl(2') 3-C 6 H 4 -0-thιenyl(2') 3-C 6 H 4 -0-thιenyl(3") 3-C 6 H 4 -0-Et 3-C 6 H 4 -O-CH 3 3-C 6 H 4 -0-CH 3 3-C 6 H 4 -0-CH 3 3-C 6 H 4 -0-C0-NH-C 6 H 4 -(CI)(2') 3-C 6 H 4 -O-CO-NH-C 6 H3-(CI)2(3 , ,5') 3-C 6 H 4 -0-CO-NH-C 6 H3-(CF 3 )2(3',5') 3-C 6 H 4 -0-CF 3 3-C 6 H 4 -0-C00Et 3-C 6 H 4 -0-COOMe 3-CgH 4 -0-CO-NH-C 6 H 4 -(CF 3 )(4') 3-C 6 H 4 -0-CO-NH-C 6 H 4 -(OCH 3 )(4') 3-CgH 4 -0-CO-NH-C 6 H 4 -(OCF 3 )(4') 3-C 6 H 4 -0-CH 2 -OMe 3-C 6 H 4 -0-C 4 H 9 (n) 3-C 6 H 4 -0-C 3 H 7 (n) 3-C 6 H 4 -0-C 8 H 17 (n) 3-C 6 H 4 -0-C 6 H 4 (CH 3 )(3') 3-C 6 H 4 -0-CH 2 -morpholinyl(1 ) 3-CgH 4 -0-CH 2 -pιpeπdιnyl(1 ) 3-C 6 H 4 -0-CH 2 -CI 3-C 6 H 4 -0-C 6 H 4 (CH 3 )(3') 3-C 6 H 4 -0-CH 2 -0-C 6 H 3 (CI 2 )(2\ , ) 3-C 6 H 4 -0-CH 2 -0-C 6 H 4 (CH 3 )(2') 3-C 6 H 4 -0-CH 2 -0-C 6 H 4 (CH 3 )(3') Table 24 Compounds 24.001 - 24.102, in which Z and W have the meanings of the corresponding compounds of Table 23, W being substituted in the 4-posιtιon Physical data of selected compounds 3-C 6 H 4 -0-CO-pyridyl(3') 3-C 6 H 4 -0-pyridyl(2') 3-C 6 H 4 -0-pyridyl(4') 3-C 6 H 4 -0-C 6 H 4 (CF 3 )(4') 3-C 6 H 4 -O-C 6 H 4 (CI)(4') 3-C 6 H 4 -0-CO-NH-C 6 H 3 -(Me)(2')(Et)(6') 3-C 6 H 4 -0-pyrimidinyl(2') 3-C 6 H -0-pyrimidinyl(4') 3-C 6 H 4 -0-pyhmidinyl(5') 3-C 6 H 4 -O-CH 3 3-C 6 H 4 -0-CO-NH-C 6 H 4 -(CI)(3') 3-C 6 H 4 -0-C 6 H 4 (Br)(4') 3-C 6 H 4 -0-C 6 H 2 (OCH 3 ) 3 (3' ) 4',5') a-Cβ- O-CβhtøCHafcO'.δ') 3-C 6 H 4 -0-thiazolyl(2') 3-C 6 H 4 -0-oxazolyl(2') 3-C 6 H 4 -0-thienyl(2') 3-CgH 4 -0-thienyl(3') 3-C 6 H 4 -0-Et 4-C 6 H 4 -0-CH 3 2-C 6 H 4 -0-CH 3 4-C 6 H 4 -0-CH 3 3-C 6 H 4 -O-CO-NH-C 6 H 4 -(CI)(2') 3-C 6 H 4 -0-CO-NH-C 6 H 3 -(CF 3 ) 2 (3 , ,5') 3-C 6 H 4 -0-CF 3 3-C 6 H 4 -0-C00Et 3-C 6 H 4 -0-C00Me 3-C 6 H 4 -0-C0-NH-C 6 H 4 -(CF 3 )(4') 3-C 6 H 4 -0-CO-NH-C 6 H 4 -(OCH 3 )(4') 3-C 6 H 4 -0-CO-NH-C 6 H 4 -(OCF 3 )(4') 3-C 6 H 4 -0-CH 2 -OMe 3-C 6 H 4 -0-C 4 H 9 (n) 3-C 6 H 4 -O-C 3 H 7 (n) 3-C 6 H 4 -0-C 8 H 17 (n) 3-C 6 H 4 -0-C 6 H 4 (CH 3 )(3') 3-C 6 H 4 -0-CH 2 -morpholιnyl(1 ) 3-C 6 H 4 -0-CH 2 -piperidιnyl(1 ) 3-C 6 H 4 -0-CH 2 -CI 3-C 6 H 4 -0-C 6 H 4 (CH 3 )(3') 3-C 6 H 4 -0-CH 2 -C 6 H 3 (CI 2 )(2',4') 3-C 6 H 4 -O-CH 2 -C 6 H 4 (CH 3 )(2') 3-C 6 H 4 -0-CH 2 -C 6 H 4 (CH 3 )(3 , ) Compounds of the formula in which Z and W have the meanings of the corresponding compounds of Table 25. Table 26 CH- Physical data 3-C 6 H 4 -CO-CH 2 -CI 3-C 6 H 4 -CO-C 6 H 4 (CH 3 )(3') 3-C 6 H 4 -CO-CH 2 -0-C 6 H 3 (CI 2 )(2 , ,4') 3-C 6 H 4 -CO-CH 2 -0-C 6 H 4 (CH 3 )(3') 4-C 6 H 4 -CO-C 6 H 4 (F)(4') 117-119° 4-C 6 H 4 -CO-C 6 H 4 (-C ≡ C-C 6 H 5 )(4 , ) 125-127° 4-C 6 H 4 -CO-C 6 H 4 (-CH 2 -CH 2 -C 6 H 5 )(4') 80-82° Compounds of the formula CH 3 in which Z and W have the meanings of the corresponding compounds of Table 26 Table 28 Comp W Physical data No 28 023 OMe 3-C 6 H 4 -0-S0 2 -NEt 2 28 024 OMe 3-C 6 H 4 -CgH 4 (Br)(4') 28 026 OMe 3-C 6 H 4 -C 6 H 3 (CH 3 ) 2 (3',5') 28 027 OMe 3-C 6 H 4 -thιazolyl(2') 28 028 OMe 3-C 6 H 4 -oxazolyl(2') 28 029 OMe 3-C 6 H 4 -thιenyl(2') 28 030 OMe 3-C 6 H 4 -thιenyl(3') 28 031 OMe 3-C 6 H 4 -S-C 6 H 5 28 032 OMe 3-C 6 H 4 -C 6 H 3 (CH 3 ) 2 (3',5') 28 033 OMe 2-C 6 H 4 -CH 2 -H 28 034 OMe 4-C 6 H 4 -CH 2 -CH 3 28 035 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 4 (CI)(4') 28 036 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 3 (Cl 2 )(2 , ,4 • ) 28 037 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 4 (N0 2 )(4') 28 038 OMe 3-C 6 H 4 -CH 2 -CF 3 28 039 OMe 3-C 6 H 4 -CH 2 -COOEt 28 040 OMe 3-C 6 H 4 -CH 2 -COOMe 28 041 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 4 -(Br)(4') 28 042 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 4 -(l)(4') 28 043 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 4 -(CH 3 )(2') 28 044 OMe 3-C 6 H 4 -CH 2 -CH 2 -OMe 28 045 OMe 3-C 6 H 4 -CH 2 -C 4 H 9 (n) 28 046 OMe 3-C 6 H 4 -CH2-C 3 H 7 (n) 28 047 OMe 3-C 6 H 4 -CH 2 -C 8 H 17 (n) 28 048 NHMe 3-C 6 4 -C 6 H 3 C\ 2 (2' A') 28 049 NHMe 3-C 6 H 4 -C 6 H 5 28 050 NHMe 3-C 6 H 4 -C 6 H 4 (OCH 3 )(4') 28 051 NHMe 3-CgH 4 -C 6 H 3 (CF 3 ) 2 (3 , ,5') 28 052 NHMe 3-CgH 4 -C 6 H 4 (CF 3 )(3') 28 053 NHMe 3-C 6 H 4 Η 2 -CO-C 6 H (CF 3 )(3') 28 054 NHMe 3-C 6 H 4 -CH 2 -CO-C 6 H 5 28 055 NHMe 3-C 6 H 4 -CH 2 -CO-C 6 H 4 (CI)(3') 28 056 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 3 -(CH 3 ) 2 (2',6') 28 057 NHMe 3-C 6 H 4 -pyrazιnyl(2') 28 058 NHMe 3-C 6 H 4 -pyrιdyl(3') 28 060 NHMe 3-C 6 H 4 -pyrιdyl(2') 28 061 NHMe 3-C 6 H 4 -pyrιdyl(4') 28 062 NHMe 3-C 6 H 4 -C 6 H 4 (CF 3 )(4') 28 063 NHMe 3-C 6 4 -C 6 H 4 (C\)(A') 28 064 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 3 -(Me)(2')(Et)(6') 28 065 NHMe 3-C 6 H 4 -pyrιmιdιnyl(2') 28 066 NHMe 3-C 6 H 4 -pyπmιdιnyl(4') 28 067 NHMe 3-CgH 4 -pyπmιdιnyl(5') 28 068 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 3 -(Me) 2 (2',4') 28 069 NHMe 3-C 6 H 4 -CH 2 -CH 3 28 070 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 4 -(CI)(3') 28 071 NHMe 3-C 6 H 4 -C 6 H 4 (Br)(4') 28 073 NHMe 3-C 6 H 4 -C 6 H 3 (CH 3 ) 2 (3',5') 28 074 NHMe 3-C 6 H 4 -thιazolyl(2') 28 075 NHMe 3-C 6 H 4 -oxazolyl(2') 28 076 NHMe 3-C 6 H 4 -thιenyl(2') 28 077 NHMe 3-C 6 H 4 -thιenyl(3') 28 078 NHMe 3-C 6 H 4 -CH 2 -Et 28 079 NHMe 4-C 6 H 4 -CH 2 -CH 3 28 080 NHMe 2-C 6 H 4 -CH 2 -CH 3 28 081 NHMe 4-C 6 H 4 -CH 2 -CH 3 28 082 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 4 -(CI)(2') 28 083 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 3 -(CI) 2 (3',5') 28 084 OMe 3-CgH 4 -CH 2 -CO-NH-C 6 H 3 -(CF 3 ) 2 (3',5') 28 085 NHMe 3-C 6 H 4 -CH 2 -CF 3 28 086 NHMe 3-C 6 H 4 -CH 2 -COOEt 28 087 NHMe 3-C 6 H 4 -CH 2 -COOMe 28 088 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 4 -(CF 3 )(4') 28 089 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 4 -(OCH 3 )(4') 28 090 OMe 3-C 6 H 4 -CH 2 -CO-NH-C 6 H 4 -(OCF 3 )(4 ) 28 091 NHMe 3-C 6 H 4 -CH 2 -CH 2 -OMe 28 092 NHMe 3-C 6 H 4 -CH 2 -C 4 H 9 (n) 28 093 NHMe 3-C 6 H 4 -CH 2 -C 3 H 7 (n) 28 094 NHMe 3-C 6 H 4 -CH 2 -C 8 H 17 (n) 28 095 NHMe 3-C 6 H 4 -C 6 H 4 (CH 3 )(3') 3-C 6 H 4 -CH 2 -CH 2 -morpholιnyl(1 ) 3-CgH 4 -CH 2 -CH 2 -pιperιdιnyl(1 ) 3-CgH 4 -CH 2 _ CH 2 "CI 3-C 6 H 4 -CH 2 -CH 2 -0-C 6 H 3 (Cl 2 )(2 , ,4') 3-C 6 H 4 -CH 2 -CH 2 -0-CgH 4 (CH 3 )(2') 3-C 6 H 4 -C 6 H 4 (F){2 , (CI){3 • ) Compounds of the formula CH, in which Z and W have the meanings of the corresponding compounds of Table 28 2 Formulation examples for active ingredients of the tables (% = per cent by weight) 2 1 Wettable powders Active ingredient from the tables Sodium ligninosulfonate Sodium lauryl sulfate Sodium dnsobutylnaphthalenesulfonate Octylphenyl polyethylene glycol ether (7-8 mol of ethylene oxide) Highly disperse silica Kaolin The active ingredient is mixed with the additives and the mixture is ground in a suitable mill until homogeneous. This gives wettable powders which can be diluted with water to give suspensions of any desired concentration Emulsions of any desired dilution can be prepared from this concentrate by diluting it with water Ready-to-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture in a suitable mill 2 4 Extruder granules Active ingredient from the tables 10% Sodium lignosulfonate 2% Carboxymethylcellulose 1 % Kaolin 87% The active ingredient is mixed with the additives, and the mixture is ground and moistened with water This mixture is extruded and subsequently dried in a stream of air 2 5 Coated granules Active ingredient from the tables 3% Polyethylene glycol (MW 200) 3% Kaolin 94% (MW = molecular weight) ln a mixer, the finely ground active ingredient is applied uniformly to the kaolin which has been moistened with polyethylene glycol This gives dust-free coated granules 2 6 Suspension concentrate Active ingredient from the tables 40% Ethylene glycol 10% Nonylphenyl polyethylene glycol ether 6% (15 mol of ethylene oxide) Sodium lignosulfonate 10% Carboxymethylcellulose 1% 37% aqueous formaldehyde solution 0 2% Silicone oil as 75% aqueous emulsion 0 8% Water 32% The finely ground active ingredient is mixed intimately with the additives. This gives a suspension concentrate from which suspensions of any desired dilution can be prepared by diluting it with water Biological examples A Microbicidal actions Example B-1 Action against Puccmia gramims on wheat a) Residual-protective action Wheat plants are sown and, 6 days thereafter, sprayed to drip point with an aqueous spray mixture prepared with a wettable powder of the active ingredient (0 02% active substance) and, 24 hours later, infected with a uredospore suspension of the fungus After an incubation time of 48 hours (conditions 95 to 100 per cent relative atmospheric humidity at 20°), the plants are placed in a greenhouse at 22°. The fungus infestation is assessed 12 days after the infection b) Systemic action An aqueous spray mixture prepared with a wettable powder of the active ingredient is poured next to wheat plants 5 days after they have been sown (0 006% active substance based on the soil volume). Care is taken that the spray mixture does not come into contact with aerial plant organs 48 hours later, the plants are infected with a uredospore suspension of the fungus After an incubation time of 48 hours (conditions 95 to 100 per cent relative atmospheπc humidity at 20°), the plants are placed in a greenhouse at 22° The fungus infestation is assessed 12 days after the infection Compounds from the tables exhibit good activity Example B-2 Action against Phytophthora infestans on tomatoes a) Residual-protective action Tomato plants are grown for three weeks and then sprayed to drip point with an aqueous spray mixture prepared with a wettable powder of the active ingredient (0 02% active substance) and, 24 hours later, infected with a sporangia suspension of the fungus The fungus infestation is assessed 5 days after the infection, during which a relative atmospheric humidity of 90 to 100 per cent and a temperature of 20° are maintained b) Systemic action An aqueous spray mixture prepared with a wettable powder of the active ingredient is poured next to tomato plants which have been grown for three weeks (0 006% active substance based on the soil volume) Care is taken that the spray mixture does not come into contact with aerial plant organs After 48 hours, the plants are infected with a sporangia suspension of the fungus The fungus infestation is assessed 5 days after the infection, during which a relative atmospheric humidity of 90 to 100 per cent at a temperature of 20° are maintained The compounds from the tables exhibit good activity Example B-3 Residual-protective action against Cercospora arachidicola on peanuts Peanut plants 10 to 15 cm in height are sprayed to drip point with an aqueous spray mixture prepared with a wettable powder of the active ingredient (0 02% active substance) and, 48 hours later, infected with a conidia suspension of the fungus The plants are incubated for 72 hours at 21° and high atmospheric humidity and subsequently placed in a greenhouse until the typical foliar lesions develop The activity of the active substance is assessed 12 days after the infection on the basis of number and size of the foliar lesions Compounds from the tables exhibit good activity Example B-4 Action against Plasmopara viticola on grapevines Grapevine seedlings in the 4-5-leaf stage are sprayed to drip point with an aqueous spray mixture prepared with a wettable powder of the active ingredient (0 02% active substance) and, 24 hours later, infected with a sporangia suspension of the fungus The fungus infestation is assessed 6 days after the infection, during which a relative atmospheric humidity of 95 to 100 per cent and a temperature of 20° are maintained Compounds from the tables exhibit good activity Example B-5 Action against Colletotnchum laqenanum on cucumbers Cucumber plants are grown for 2 weeks and then sprayed with a spray mixture prepared with a wettable powder of the active ingredient (concentration 0.002%) After 2 days, the plants are infected with a spore suspension (1 5 x 10 5 spores/ml) of the fungus and incubated for 36 hours at 23°C and high atmospheric humidity Incubation is then continued at normal atmospheric humidity and at approximately 22°C 8 days after the infection, the fungus infestation which has taken place is assessed Compounds from the tables exhibit good activity Example B-6 Residual protective action against Ventuna inaequalis on apples Apple cuttings with fresh shoots 10 to 20 cm in length are sprayed to drip point with an aqueous spray mixture prepared with a wettable powder of the active ingredient (0 02% active substance) and, 24 hours later, infected with a conidia suspension of the fungus The plants are incubated for 5 days at a relative atmospheric humidity of 90 to 100 per cent and placed for a further 10 days in a greenhouse at 20 to 24° The fungus infestation is assessed 12 days after the infection Compounds from the tables exhibit good activity Example B-7 Action against Ervsiphe graminis on barley a) Residual-protective action Barley plants approximately 8 cm in height are sprayed to drip point with an aqueous spray mixture prepared with a wettable powder of the active ingredient (0 02% active substance) and, 3 to 4 hours later, dusted with conidia of the fungus The infected plants are placed in a greenhouse at 22° The fungus infestation is assessed 12 days after the infection Compounds from the tables exhibit good activity b) Systemic action An aqueous spray mixture prepared with a wettable powder of the active ingredient is poured next to barley plants approximately 8 cm in height (0 002% active substance based on the soil volume) Care is taken that the spray mixture does not come into contact with aerial plant organs 48 hours later, the plants are dusted with conidia of the fungus The infected plants are placed in a greenhouse at 22° The fungus infestation is assessed 12 days after the infection Compounds from the tables exhibit good activity Example B-8 Action against Podosphaera leucotricha on apple shoots Apple cuttings with fresh shoots approximately 15 cm in length are sprayed with a spray mixture (0 06% active substance) After 24 hours, the treated plants are infected with a conidia suspension of the fungus and placed in a controlled-environment cabinet at a relative atmospheric humidity of 70% and at 20°C The fungus infestation is assessed 12 days after the infection Compounds from the tables exhibit good activity Biological examples B Insecticidal actions Example B-9 Action against Aphis craccivora Pea seedlings are infected with Aphis craccivora, subsequently sprayed with a spray mixture comprising 100 ppm of active ingredient and then incubated at 20° 3 and 6 days later, the per centage reduction in population (% activity) is determined by comparing the number of dead aphids on treated and untreated plants In this test, compounds of the tables exhibit good activity, i e a destruction rate of over 80% Example B-10 Action against Diabrotica balteata Maize seedlings are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient, then, after the spray coating has dried on, populated with 10 second instar larvae of Diabrotica balteata and subsequently introduced into a plastic container 6 days later, the per centage reduction in population (% activity) is determined by comparing the number of dead larvae between the treated and untreated plants In this test, compounds of the tables exhibit good activity Example B-11 Action against Heliothis virescens Young soya plants are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of active ingredient, then, after the spray coating has dried on, populated with 10 first instar caterpillars of Heliothis virescens and subsequently introduced into a plastic container 6 days later, the per centage reduction in population and the feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage between the treated and untreated plants In this test, compounds of the tables exhibit good activity Example B-12 Action against Spodoptera httoralis Young soya plants are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of active ingredient, then, after the spray coating has dried on, populated with 10 third instar caterpillars of Spodoptera littoralts and subsequently introduced into a plastic container 3 days later, the per centage reduction in population and the percentage reduction in feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage between the treated and untreated plants In this test, compounds of the tables exhibit good activity B-13 Action against Nilaparvata lugens Rice plants are treated with an aqueous emulsion spray mixture which comprises 100 ppm of the active ingredient After the spray coating has dried on, the rice plants are populated with 2nd and 3rd instar leaf hopper larvae The test is evaluated 21 days later The percentage reduction in population (% activity) is determined by comparing the number of surviving leafhoppers on the treated with those on the untreated plants The compounds of the tables exhibit an activity of over 90% B-14 Action against Plutella xylostella caterpillars Young cabbage plants are sprayed with an aqueous emulsion spray mixture which comprises 100 ppm of the active ingredient After the spray coating has dried on, the cabbage plants are populated with 10 third instar caterpillars of Plutella xylostella and introduced into a plastic container The test is evaluated 3 days later The per centage reduction in population or the per centage reduction in feeding damage (% activity) is determined by comparing the number of dead caterpillars and the feeding damage on the treated with those on the untreated plants Compounds from the tables exhibit good activity Example B-15 Action against Musca domestica A sugar lump is treated with a solution of the test substance in such a way that, after drying overnight, the concentration of test substance in the sugar is 250 ppm This treated lump is placed on an aluminium dish together with a wet cotton wool ball and 10 adult Musca domestica of an OP-resistant strain, covered with a glass beaker and incubated at 25°C The mortality rate is determined after 24 hours Compounds from the tables exhibit good activity Biological examples: C. Aca cidal actions B-16: Action against Tetranychus urticae Young bean plants are populated with a mixed population of Tetranychus urticae and, one day later, sprayed with an aqueous emulsion spray mixture which comprises 400 ppm of the active ingredient. The plants are subsequently incubated for 6 days at 25°C and then evaluated. The per centage reduction in population (% action) is determined by comparing the number of dead eggs, larvae and adults on the treated with those on the untreated plants. Compounds from the tables exhibit good activity. B-17: Action on mixed population of Tetranychus cinnabarmus Dilution series. Dwarf beans in the 2-leaf stage are populated with a mixed population (eggs, larvae/nymphs, adults) of an OP-tolerant strain of Tetranychus cinnabarinus. 24 hours after infection, the products are applied to the plants in an automatic spray cabin at the dosages 200, 100, 50 mg of a.s./l. The substances are formulated and are diluted with water to give the appropriate dosages. The test is evaluated 2 and 7 days after application for per centage mortality of eggs, larvae/nymphs and adults. Compounds of the tables exhibit mortality rates above 70% in dilutions of as little as 50 mg of a.s./litre. B-18: Action against Boophilus microplus Female adult ticks which have sucked themselves full are glued to a PVC pane and covered with a cotton wool ball, and 10 ml of aqueous test solution comprising 125 ppm of active ingredient are poured over. The cotton wool ball is removed and the ticks are incubated for 4 weeks for oviposition. The action manifests itself either in the case of the female as mortality or sterility or in the case of the eggs as ovicidal action

Claims: WHAT IS CLAIMED IS 1 A compound of the formula where X is CH or N, Z is OR 2 , SR 2 , N(R 3 )R,, or Y and Z together form a 5- to 7-membered ring which contains 2 or 3 hetero atoms O and/or N and which is unsubstituted or substituted by C,-C 4 alkyl, halo-C 1 -C 4 alkyl, halogen, =0 or cyclopropyl, Y is a direct bond or C r C 6 alkylene which is unsubstituted or substituted by C r C 3 alkyl, C 2 - C 3 alkylιdene or C 3 -C 6 cycloalkylιdene, U is O, S, NR 7 , SO or S0 2 , W is substituted or unsubstituted aryl or substituted or unsubstituted hetaryl, R, is cyclopropyl, C Cgalkyl or halo-C^Cealkyl, R 2 and R 3 independently of one another are C,-C 6 alkyl or halo-C,-C 6 alkyl, R 4 and R 5 independently of one another are hydrogen, C,-C 6 alkyl or CrCgalkoxy, R 7 is hydrogen, C,-C 6 alkyl, benzyl, halo-C,-C 6 alkylcarbonyl, halo-C 2 - C 6 alkenylcarbonyl, R 21 and R 22 independently of one another are hydrogen, halogen, C,-C 8 alkyl or C r C 8 alkoxy or C r C a alkylthιo, R 23 . R 24 . R 25 . R 26 independently of one another are hydrogen, halogen, C,-C 8 alkyl or C,- C B alkoxy 2 A compound of the formula I according to claim 1 in which W is a group a) ( ) n in which D are identical or different substituents halogen, cyano, nitro, C C^alkyl, halo-C,-C 6 alkyl, C 2 -C 12 alkenyl, halo-C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, halo-C 2 -C 12 alkynyl, free or halogenated C 3 - C 6 cycloalkyl, free or halogenated C 3 -C 6 cycloalkylmethyl, free or halogenated C 3 - C 6 cycloalkylmethyloxy, Cr^alkoxy, halo-C,-C 4 alkoxy, C 2 -C 6 alkenyloxy, halo-C 2 - C 6 alkenyloxy, C 2 -C 6 alkynyloxy, halo-C 2 -C 6 alkynyloxy, C 2 -C 12 alkoxyalkyl, C,-C 4 alkoxycarbonyl, C t -Cgalkylcarbonyl, it being possible for all the abovementioned alkyl, alkenyl or alkynyl groups to be substituted by aryl or hetaryl, aryloxy or hetaryloxy, arylsulfenyl, arylsuifinyl, arylsulfonyl, hetarylsulfenyl, hetarylsulfinyl or hetarylsulfonyl radicals, each of which can be additionally substituted or unsubstituted, furthermore substituted or unsubstituted aryl, substituted or unsubstituted hetaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted arylcarbonyl, substituted or unsubstituted aryloxy, substituted or unsubstituted benzyl, substituted or unsubstituted cyclohexenyl, substituted or unsubstituted cyclohexenylalkoxy, substituted or unsubstituted cyclohexenylalkylthio, substituted or unsubstituted cyclohexadienyl, substituted or unsubstituted cyclohexadienylalkoxy, substituted or unsubstituted cyclohexadienylalkylthio, a substituted or unsubstituted fused ring having up to 14 C atoms, or in which D is once the group m which R 13 is hydrogen, cyano, C^Cealkyl, C 3 -C 6 cycloalkyl, CrCealkoxycarbonyl, C Cgacyl, C C 2 - alkoxιmιno-C r C 6 alkyl, aryl, hetaryl, heterocyclyl, naphthyl; C,-C 6 alkoxy, aryloxy, hetaryloxy, CrCealkylamino, bιs(C 1 -C β alkyl)amιno, arylamino, hetarylammo, in which all the abovementioned radicals (with the exception of cyano) can be unsubstituted or substituted by alkyl, alkoxy, haloalkyl, haloalkoxy, alkylthio, alkylsulfenyl, alkylsulfinyl, halogen, nitro, cyano, aryl, aryloxy, hetaryl, hetaryloxy, or R, 3 is the group in which R 15 is hydrogen, C r C 6 alkyl, halo-CrCβalkyl, C,-C 6 alkoxy, halo-C,-C 6 alkoxy, halogen, C 3 - C 6 cycloalkyl which is unsubstituted or substituted by 1 to 5 halogen atoms, C 2 -C 6 alkenyl, halo-C 2 -C 6 alkenyl, substituted or unsubstituted C 2 -C 6 alkynyl, aryl, hetaryl or heterocyclyl, all three of which independently of one another are unsubstituted or monosubstituted to pentasubstituted by halo-C C 6 alkyl, halogen, or halo-C r C 6 alkoxy, tπ(C r C 4 -alkyl)sιlyl, d CrCalky phenylsilyl, where, if m is greater than 1 , the radicals R 15 can be identical or different, Q is a direct bond, C Cgalkylene, C 2 -C 6 alkenylene, C 2 -C 6 alkynylene, O, 0(C r C 8 alkylene), (C r C 6 alkylene)O, S(=O) p , S(=O) p (C 1 -C 6 alkylene) or (C 1 -C 6 alkylene)S(=O) p , n is O, 1 , 2, 3, 4 or 5, p is 0, 1 or 2, and R 14 is hydrogen, C,-C 6 alkyl, C Cehaloalkyl having 1 to15 halogen atoms, C 1 -C 4 alkoxy-C 1 - C 2 alkyl, C 2 -C 4 alkenyl-C r C 2 alkyl which is unsubstituted or substituted by 1 to 3 halogen atoms, C 2 -C 4 alkynyl-C C 2 alkyl, C 3 -C 6 cycloalkyl which is unsubstituted or substituted by 1 to 4 halogen atoms, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl which is unsubstituted or substituted by 1 to 4 halogen atoms, cyano-C Calkyl, C Calkoxycarbonyl-CrCalkyl, which is unsubstituted or substituted by halogen, C,-C 3 alkyl, C 1 -C 4 alkoxy, C,-C 4 haloalkyl, cyano, nitro, C r C 4 alkylene dioxy, it being possible for the phenyl group to be substituted by 1 to 3 identical or different substituents, phenyl which is unsubstituted or monosubstituted or disubstituted by independent substituents from the series consisting of C C 4 alkyl, C- C 4 alkoxy, halogen, C Cjhaloalkyl having 1 bis 3 halogen atoms, nitro or cyano, pyndyl which is unsubstituted or monosubstituted or disubstituted by independent substituents from the series consisting of C 1 -C 4 alkyl, C,-C 4 alkoxy, halogen, C 1 -C 2 haloalkyl having 1 to 3 halogen atoms, nitro or cyano 3 A compound according to claim 1 in which R, is methyl, R 2 , R 3 and R 5 independently of one another are C 1 -C 2 alkyl, preferably methyl, R 4 is hydrogen 4 A compound according to claim 1 in which Y is O, S, or S=0, preferably O, Z is OR 2 , SR 2 , N(R 3 )H, preferably OR 2 , SR 2 , R 2 and R 3 are C,-C 2 alkyl, preferably methyl 5 A compound according to claim 1 in which Y is O, S, or S=0, preferably O, R 2 is C,-C 2 alkyl, preferably methyl 6 A compound according to claim 1 , in which Y and Z together are a group a) and in which A is alkanediyl having 1 to 3 carbon atoms which is unsubstituted or substituted by methyl, preferably dimethylene, R 6 is hydrogen, C,-C 3 alkyl, cyclopropyl or CF 3 , 7 A compound according to claim 1 in which V is -CH , -CH(CH 3 )-, -CH(CH 3 ) 2 -, -(CH 2 ) 2 -, -(CH 2 ) 3 -, R 2 , and R 22 independently of one another are hydrogen, chlorine, bromine, C r C 4 alkyl or C r C 4 alkoxy, R 23 , R 24 , R 2 5, R 26 are hydrogen 8 A compound according to claim 1 in which Z is OCH 3 or NHCH 3 , W is substituted or unsubstituted phenyl, R 2 , and R 22 independently of one another are hydrogen, chlorine or methyl, R 2 3, 2 4, R 2 5, R 26 are hydrogen 9 A compound according to claim 1 in which W is phenyl which is unsubstituted or substituted by CrCealkyl, halo-C r C 6alky ,, C 2 -C 4 alkenyl, halo-C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, halo-C 2 -C 4 alkynyl, C,-C 4 alkoxy, halo-C r C 4 alkoxy, C 2 -C 6 alkenyloxy, halo-C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, halo-C 2 -C 4 alkynyloxy, C C 4 alkoxycarbonyl, C^Cealkylcarbonyl, the abovementioned alkyl, alkenyl and alkynyl groups being unsubstituted or further substituted by aryl, hetaryl, aryloxy, hetaryloxy, arylsulfenyl, arylsulfinyl, arylsulfonyl, hetarylsulfenyl, hetarylsulfinyl or hetarylsulfonyl, each of which is unsubstituted or additionally substituted, furthermore aryl, hetaryl, heterocyclyl, arylcarbonyl, aryloxy, benzyl, cycloalkyl, cyclohexenyl, cyclohexenylalkoxy, cyclohexenylalkylthio, cyclohexadienyl, cyclohexadienylalkoxy, cyclohexadienylalkylthio, all the abovementioned cyclic groups being unsubstituted or mono- or polysubstituted by halogen, C,-C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C,-C 4 alkoxy, C,- C 4 alkylthιo, C r C 4 haloalkyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyl, d^haloalkoxy, halogen, cyano, cyano-C,-C 2 alkyl, cyano-CrC^lkoxy, OH, N0 2 , SCN, thiocyanomethyl, Sι(CH 3 ) 3 , NH 2 , NH(C r C 4 alkyl), N(C,-C 4 alkyl) 2 , d-Calkoxymethyl, C,-C 4 haloalkylcarbonyl, C C 4 haloalkyloxycarbonyl, aminocarbonyl, C,-C 4 - alkylammocarbonyl, bιs(C,-C 4 alkylamιno)carbonyl, arylaminocarbonyl, arylaminothiocarbonyl, -CSNH 2 , -SH, C,-C 4 alkylthιomethyl, C 2 - C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 2 -C 4 haloalkenyloxy, C 1 -C 4 alkylsulfιnylmethyl, C,-C 4 -alkyl- sulfonylmethyl, phenylsulfinylmethyl, phenylsulfonylmethyl, tnfluoromethylsulfonyl, C 3 -C 6 - cycloalkyl, C 1 -C 4 haloalkylcarbonyloxy, C,-C 4 alkylcarbonyloxy, C 1 -C 4 alkoxycarbonyloxy, haloalkoxycarbonyloxy, ammocarbonyloxy, CrC^lkylaminocarbonyloxy, bιs(C r C 4 - alkylamιno)carbonyloxy, arylammocarbonyloxy or arylaminothiocarbonyloxy 10 A compound according to claim 1 in which V is -CH 2 - -CH(CH 3 )-, -CH(CH 3 ) 2 -, -(CH 2 ) 2 -, -(CH 2 ) 3 -, U is S or NR 7 R 21 and R 22 independently of one another are halogen, chlorine, bromine, C,-C 4 alkyl or C,- C 4 alkoxy, 2 3. R 2 4 2 5. R 2 e are hydrogen 1 1 A compound according to claim 2 in which D is halogen, C r C 4 alkyl, halo-C C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, free or chlorinated cyclopropylmethyl, C t ^alkoxy, halo-C,-C 4 alkoxy, C 2 -C 12 alkoxyalkyl, C,-C 4 acyl, C,-C 4 alkoxycarbonyl, free or chlorinated cyclopropylmethyloxy, or substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, or substituted or unsubstituted benzyl, where the substituents on phenyl, phenoxy and benzyl are selected from the series consisting of halogen, nitro, C,-C 2 alkyl, halo-C,-C 2 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C,-C 2 alkoxy, C 2 - C 1? alkoxyalkyl, 12 A compound according to claim 11 , in which D is halogen, C^Calkyl, halo-C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, free or chlorinated cyclopropylmethyl, C 1 -C 4 alkoxy, halo-C,-C 4 alkoxy, C,-C 4 acyl, C,- C 4 alkoxycarbonyl, free or chlorinated cyclopropylmethyloxy, n is 0, 1 or 2 13 A compound according to claim 2, in which D is the group in which R t3 is hydrogen, cyano, C,-C 4 alkyl, cyclopropyl, C r C 4 alkoxycarbonyl, C,-C 4 acyl, C 1 -C 2 alkoxιmιno-C,-C 6 alkyl, or the group in which R 15 is C,-C 6 alkyl, halo-C Cealkyl, halo-C r C 6 alkoxy, halogen, C 3 -C 6 cycloalkyl, which is unsubstituted or substituted by 1 to 5 halogen atoms, C 2 -C 6 alkenyl, halo-C 2 - C 6 alkenyl, substituted or unsubstituted C 2 -C 6 alkynyl, aryl, hetaryl or heterocyclyl, all three of which independently of one another are unsubstituted or monosubstituted to pentasubstituted by halo-C r C 6 alkyl, halogen, CrC-ealkoxy or halo-C r C 6 alkoxy, trι(C,-C 4 -alkyl)sιlyl, dι(C 1 -C 4 alkyl)phenylsιlyl, where, if m is greater than 1 , it is possible for the radicals R 15 to be identical or different, Q is a direct bond, C,-C e alkylene, C 2 -C 6 alkenylene, C 2 -C 6 alkynylene, O, 0(C 1 -C 6 alkylene), n is 0, 1 , 2, or 3, p is 0, 1 or 2, and R 14 is hydrogen, C r C 4 alkyl, C 1 -C 4 haloalkyl having 1 to 6 halogen atoms, C 2 -C 4 alkenyl, C 2 - C 4 haloalkenyl having 1 to 3 halogen atoms 14 A compound according to claim 13, in which R 15 is C,-C 6 alkyl, halo-^-Cealkyl, cyclopropyl which is unsubstituted or substituted by 1 to 5 chlorine atoms, C 2 -C 6 alkenyl which is unsubstituted or substituted by 1 to 3 halogen atoms, or unsubstituted or substituted C 2 -C 6 alkynyl, furthermore phenyl, which is unsubstituted or monosubstituted to pentasubstituted by C,-C 6 alkyl, halo-C,-C 6 alkyl, halogen, C,-C 6 alkoxy or halo-C r C 6 alkoxy, or pyndyl which is unsubstituted or monosubstituted to pentasubstituted by C,-C 6 alkyl, halo-C Cealkyl, halo, C 1 -C 6 alkoxy or halo-C^Csalkoxy, Q is a direct bond, C,-C 4 alkylene, O, O^-Calkylene), (C,-C 4 alkylene)0, m is O, 1 , 2 15 A compound according to claim 13, in which R 13 is hetaryl or heterocyclyl, which, independently of one another, are unsubstituted or monosubstituted to pentasubstituted by C.,-C β alkyl, halo-C r C 6 alkyl, halogen, CrCg-alkoxy or halo-C,-C 6 alkoxy 16 A compound of the formula I according to claim 1 , in which W is substituted or unsubstituted pyndyl, pynmidinyl, imidazolyl, thiazolyl, 1 ,3,4-thιadιazolyl, tnazolyl, thienyl, furanyl, pyrrolyl, quinolyl, isoquinolyl, benzoxazolyl, quinoxa nyl, benzothiazolyl, benzimidazolyl, or mdolyl 17 A compound of the formula I according to claim 16, in which W is pyndyl or pynmidinyl, each of which is unsubstituted or substituted by C C 4 alkyl, halo- C r C 4 alkyl, C 2 -C 6 alkenyl, halo-C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, halo-C 2 -C 6 alkynyl, C,-C 4 alkoxy, halo-C C 4 alkoxy, C 2 -C, 2 alkoxyalkyl, C,-C 6 acyl, C 1 -C 4 alkoxycarbonyl, substituted or unsubstituted phenyl, substituted or unsubstituted phenoxy, or substituted or unsubstituted benzyl 18 A compound of the formula I according to claim 17, in which V is a direct bond or -CH 2 -, W is pyndyl or pynmidinyl, each of which is unsubstituted or substituted by CrC 4 alkyl, halo- C,-C 4 alkyl, phenyl, phenoxy or benzyl and in which phenyl, phenoxy and benzyl are unsubstituted or monosubstituted to trisubstituted by halogen, C,-C 4 alkyl, C 2 -C 4 alkenyl, halo- C,-C 4 alkyl, halo-C 2 -C 4 alkenyl, C 1 -C 4 alkoxy, halo-C,-C 6 alkoxy or cyano 19 A process for the preparation of a compound of the formula I according to claim 1 , which comprises reacting a compound of the formula II with a compound of the formula III w π in in which X, Y, Z, R,, V, U, W and R 21 to R 26 have the meanings given for formula I 20 A process for the preparation of a compound of the formula I according to claim 1 , which comprises reacting a compound of the formula IV with a compound of the formula V IV in which X, Y, Z, R,, V, U, R 21 to R 26 and W have the meanings given for formula I and in which L is a leaving group, in a solvent under alkaline conditions 21 A process for the preparation of a compound of the formula XIV, which comprises reacting a compound of the formula II with a compound of the formula XIII XIV in which Y, Z, V, U, W and R 21 to R 26 have the meanings given for formula I according to claim 1 22 A compound of the formula III in which X, Y, Z, R,, V, U and W have the meanings given for formula I according to claim 1 23 A compound of the formula XIII u-w in which Y, Z, V, U, W have the meanings given for formula I according to claim 1 24 A compound of the formula XIV in which Y, Z, V, U, W and R 21 to R 26 have the meanings given for formula I according to claim 1 25 A composition for controlling pests which comprises, as active ingredient, an effective amount of a compound according to claim 1 together with a suitable carrier material 26 A method of controlling and preventing pests, which comprises applying a compound according to claim 1 to the pests or their environment 27 A method according to claim 26, the pests being phytopathogenic fungi 28 A method according to claim 26, the pests being insects or Acaπna 29 A method according to claim 26, in which seed is treated 30 Seed which has been treated according to claim 26

Inventors: HUETER OTTMAR FRANZ, SZCZEPANSKI HENRY, ZELLER MARTIN, HUETER, OTTMAR, FRANZ, SZCZEPANSKI, HENRY, ZELLER, MARTIN
Applicants: CIBA GEIGY AG, HUETER OTTMAR FRANZ, SZCZEPANSKI HENRY, ZELLER MARTIN, HUETER, OTTMAR, FRANZ, NOVARTIS AG, SZCZEPANSKI, HENRY, ZELLER, MARTIN
Application year: 1997
Main classification: C07C251
IPC codes: A01N37, A01N43, C07C69, C07C251, C07C255, C07C323, C07D213, C07D239, C07D241, C07D261, C07D263, C07D277, C07D317, C07D333