4-Acylaminophenyl-3-phenylpropargyl and-3-phenylallyl ether derivatives having herbicidal activity are described, for example, in Japan Kokai Tokkyo Koho (1996), JP-A-08 157 435 (CAN 125: 195200 AN 1996: 531728 CAPLUS).

Novel phenoxy- (E)-propenylphenyl derivatives having herbicidal and growth-inhibiting properties have now been found.

The present invention accordingly relates to compounds of formula I wherein Roi is hydrogen, C1-C8alkyl, C3-C8alkenyl or Cs-Csatkyny) ; or Roi is phenyl or phenyl-C,-C6alkyl, it being possible for the phenyl rings in turn to be mono- to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C4alkyl, C,-C4halo- alkyl, C,-C4alkoxy,-CN,-N02, C,-Cealkylthio, C,-C8alkylsulfinyl or C,-Caalkylsulfonyl ; or Roi is C,-C8alkyl mono-to penta-substituted by halogen or mono-, di-or tri-substituted by -CN, C,-C6alkylamino, di (C1-C6alkyl) amino or C,-C4alkoxy ; n is 0, 1,2, 3 or 4 ; each R, independently is halogen,-CN,-SCN,-SF5,-N02,-NH2,-C02R7,-CONR8R9, -C (S) NH2, -C(R10)=NOR11, -COR12, -OR13, -SR14, -SOR15, -SO2R16, -OSO2R17, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl or C3-C6cycloalkyl ; or C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by-CN,-N02, - NR18R19, -CO2R20, -CONR21R22, -COR23, -C (R24) =NOR25, -C (S) NR26R27, -C(C1-C4alkylthio)=NR28, -OR29, -SR30, -SOR31, -SO2R32 or Cg-Cecydoatky) ; and/or each R, independently is C3-C6cycloalkyl mono-to penta-substituted by halogen and/or mono-, di- or tri-substituted by -CN, -NO2, -NR18R19, -CO2R20, -CONR21R22, -COR23, - C (R24) =NOR25,-C (S) NR26R27, -C(C1-C4alkylthio)=NR28, -SR30, -SOR31, -SO2R32 or C3- C6cycloalkyl ; and/or each R, independently is phenyl, which in turn can be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; and/or two adjacent R, together form a C,-C7alkylene bridge, which can be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which can be mono-to penta- substituted by halogen and/or mono-, di-or tri-substituted by d-Ceaiky) or C,-C6alkoxy, the total number of ring atoms being at least 5 and at most 9; and/or two adjacent R, together form a C2-C7alkenylene bridge, which can be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which can be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C6alkyl or C,-C6- alkoxy, the total number of ring atoms being at least 5 and at most 9; R3 and R4 are each independently of the other hydrogen, halogen,-CN, C1-C4alkyl or C,-C4alkoxy ; or R3 and R4 together are C2-C5alkylene ; R7 is hydrogen, C1-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or C1-C8alkyl, C3-C8alkenyl or Cs-Ceatkyny) mono-to penta-substituted by halogen or mono-, di-or tri-substituted by C1-C4alkoxy or phenyl, it being possible for phenyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; R8 is hydrogen or C,-C8alkyl ; Rg is hydrogen or C,-C8alkyl, or C,-C8alkyl mono-, di-or tri-substituted by-COOH, C1-C8alkoxycarbonyl or-CN, or Rg is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C4alkyl, C,-C4haloalkyl, C,-C4alkoxy,-CN,-N02, C,-C4alkylthio, C,-C4alkylsulfinyl or C1-C4alkylsulfonyl ; or RB and Rg together are C2-C5alkylene ; Rio is hydrogen, C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl ; R"is hydrogen, C1-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C1-C4haloalkyl or C3-C6haloalkenyl ; R, 2 is hydrogen, C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl ; R, 3 is hydrogen, C1-C8alkyl, C3-C8alkenyl or C3-C8alkynyl ; or R, 3 is phenyl or phenyl-C,-C6alkyl, it being possible for the phenyl rings in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C4alkyl, C1-C4halo- alkyl, C1-C4alkoxy, -CN, -NO2, C1-C8alkylthio, C1-C8alkylsulfinyl or C1-C8alkylsulfonyl, or R13 is C1-C8alkyl mono-to penta-substituted by halogen or mono-, di-or tri-substituted by - CN, C,-C6alkylamino, di (C,-C6alkyl) amino or C,-C4alkoxy ; R, 4 is hydrogen, C1-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or Ci-Cgatky) mono-to penta- substituted by halogen or mono-, di-or tri-substituted by-CN or C1-C4alkoxy ; R15 R16 and R17 are each independently of the others C1-C8alkyl, C3-C8alkenyl or C3-C8- alkynyl, or C,-C8alkyl mono-to penta-substituted by halogen or mono-, di-or tri-substituted by-CN or C,-C4alkoxy ; Ris is hydrogen or C1-C8alkyl ; Rig is hydrogen, C1-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C4alkyl, C,-C4haloalkyl, C,-C4alkoxy,-CN,-NO2, C,-C4alkylthio, C1-C4- alkylsulfinyl or C1-C4alkylsulfonyl ; or Rig and R19 together are a C2-Csalkylene chain, which can be interrupted by an oxygen or a sulfur atom; R20is hydrogen, C1-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4- alkylsulfinyl or C1-C4alkylsulfonyl ; R2, is hydrogen or C1-C8alkyl ; R22 is hydrogen or C,-CBalkyl, or C,-Csalkyl mono-, di-or tri-substituted by-COOH, C,-C8- alkoxycarbonyl or-CN, or R22 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C,-C4haloalkyl, C,-C4alkoxy,-CN,-NO2, C,-C4alkylthio, C,-C4alkylsulfinyl or C,-C4alkylsulfonyl ; or R2, and R22 together are C2-C5alkylene ; R23 is hydrogen, C,-C4alkyl, C,-C4haloalkyl or C3-C6cycloalkyl ; R24 is hydrogen, C,-C4alkyl, C,-C4haloalkyl or C3-C6cycloalkyl ; Rzs is hydrogen, C,-CBalkyl, C3-C8alkenyl, C3-Csalkynyl, C,-C4haloalkyl or C3-C6haloalkenyl ; R26 is hydrogen or C,-C8alkyl ; R27 is hydrogen or C,-CBalkyl, or C,-C8alkyl mono-, di-or tri-substituted by-COOH, C1-C8- alkoxycarbonyl or-CN, or R27 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C4alkyl, C,-C4haloalkyl, C,-C4alkoxy,-CN,-NO2, C,-C4alkylthio, C,-C4alkylsulfinyl or C,-C4alkylsulfonyl ; or R26 and R27 together are C2-C5alkylene ; R28 is hydrogen or C,-C8alkyl ; R29 and R30 are each independently of the other hydrogen, C1-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or Ci-Cgaiky) mono-to penta-substituted by halogen or mono-, di-or tri- substituted by-CN or C1-C4alkoxy; R3, and R32 are each independently of the other C1-C8alkyl, C3-C8alkenyl, C3-C8alkenyl or C3-C8alkynyl, or C,-C8alkyl mono-to penta-substituted by halogen or mono-, di-or tri-substituted by-CN or C,-C4alkoxy ; mis1, 2, 3, 4 or 5 ; each R2 independently is halogen,-CN,-SCN,-OCN,-N3,-SF5,-NO2,-NR33R34,-CO2R35, -CON36R37, -C(R38)=NOR39, -COR40, -OR41, -SR42, -SOR43, -SO2R44, -OSO2R45, -N([CO]pR46)COR47, -N(OR54)COR55, -N(R56)SO2R57, -N(SO2R58)SO2R59, -N=C(OR60)R61, -CR62 (OR63) OR64,-OC (O) NR65R66,-SC (O) NR67R68, -OC(S)NR69R70 or -N-phthalimide ; and/or R2 is a 5-to 7-membered heterocyclic ring system which can be aromatic or partially or fully saturated and which can contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, it being possible for such a heterocyclic ring system in turn to be mono-to penta- substituted by halogen and/or mono-, di-or tri-substituted by C,-C4alkyl, C,-C4haloalkyl, hydroxy-C,-C4alkyl, C,-C4alkoxy, C,-C4haloalkoxy, C,-C4alkoxy-C,-C4alkyl,-CN,-NO2, C,-C6alkylthio, C1-C6alkylsulfinyl or C,-C6alkylsulfonyl ; R33 is hydrogen or C1-C8alkyl ; and R34 is hydrogen, C,-C8alkyl, C3-C8alkenyl, C3-Cealkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; or R33 and R34 together are a C2-Csalkylene chain, which can be interrupted by an oxygen or a sulfur atom; R35 is hydrogen, Ci-Ceatkyt, C3-C8alkenyl or C3-C8alkynyl, or C,-C8alkyl, C3-Cealkenyl or C3-C8alkynyl mono-to penta-substituted by halogen or mono-, di-or tri-substituted by C,-C4alkoxy or phenyl, it being possible for phenyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, - CN,-NO2, C,-C4alkylthio, C,-C4alkylsulfinyl or C,-C4alkylsulfonyl ; R36 is hydrogen or C1-C8alkyl ; R37 is hydrogen or C,-C8alkyl, or C,-C8alkyl mono-, di-or tri-substituted by-COOH, C,-C8alkoxycarbonyl or-CN, or R37 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, -C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; or R36 and R37 together are C3-C5alkylene ; R38 is hydrogen, C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl ; R39 is hydrogen, C1-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C1-C4haloalkyl or C3-C6haloalkenyl ; R40 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C8alkylthio, -C(O)-C(O)OC1-C4alkyl or C3-C6cycloalkyl ; R4, is hydrogen, C1-C8alkyl, C1-C8haloalkyl, C3-C8alkenyl, C3-C8alkynyl, C1-C6alkoxy-C1-C6- alkyl, C,-C8alkylcarbonyl, C,-C8alkoxycarbonyl, C3-CBalkenyloxycarbonyl, C,-C6alkoxy- C1-C6alkoxycarbonyl, C1-C6alkylthio-C1-C6alkyl, C1-C6alkylsulfinyl-C1-C6alkyl or C1-C6alkyl- sulfonyl-C1-C6alkyl ; or R4, is phenyl or phenyl-C1-C6alkyl, it being possible for the phenyl rings in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C4alkyl, C,-C4halo- alkyl, C1-C4alkoxy, -CN, -NO2 or -S(O)2C1-C8alkyl, or R4, is C,-C8alkyl mono-, di-or tri-substituted by-COOH, C1-C8alkoxycarbonyl, C1-C6alkyl- amino, di (C,-C6alkyl) amino or-CN; R42 is hydrogen, C,-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or C1-C8alkyl mono-to penta- substituted by halogen or mono-, di-or tri-substituted by-CN or C,-C4alkoxy ; R43 and R44 are each independently of the other C1-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or C,-C8alkyl mono-to penta-substituted by halogen or mono-, di-or tri-substituted by-CN or C1-C4alkoxy ; R45 is C,-C8alkyl, or C1-C8alkyl mono-to penta-substituted by halogen or mono-, di-or tri- substituted by-CN or C,-C4alkoxy, C3-C8alkenyl or C3-C8alkynyl, or R45 is phenyl, it being possible for the phenyl ring to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C4alkyl, C,-C4haloalkyl, C,-C4alkoxy,-CN, NO2, C1-C8alkylthio, C1-C8alkylsulfinyl or C1-C8alkylsulfonyl ; R46 is hydrogen, C,-C8alkyl, C3-Cealkenyl, C3-C8alkynyl or C,-C4haloalkyl ; R47 is hydrogen, C1-C8alkyl, C1-C4alkoxy, C3-C8alkenyl or C3-C8alkynyl, or C1-C8alkyl mono- to penta-substituted by halogen or mono-, di-or tri-substituted by-CN, C1-C4alkoxy, C1-C8- alkoxycarbonyl,-NH2, C,-C4alkylamino, di (C,-C4alkyl) amino,-NR48COR4g,-NRsoSOzRs, or -NRs2CO2Rs39 or R47 is phenyl or benzyl, each of which can in turn be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C,-C4alkylsulfonyl ; p is 0 or 1 ; R48, R49, R50, R5,, R52 and R53 are each independently of the others hydrogen, C-C8alkyl, phenyl, benzyl or naphthyl, it being possible for the three last-mentioned aromatic radicals in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C8alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylamino, di (C,-C4alkyl) amino,-NH2,-CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C,-C4alkylsulfonyl ; R54 and R55 are each independently of the other hydrogen, C1-C8alkyl, or phenyl which in turn can be mono-to penta-substituted by halogen and/or mono-, di-or tri-substiluted by C,-C4- alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C8alkylthio, C1-C8alkylsulfinyl or C,-C8alkyl- sulfonyl ; R56 is hydrogen, C1-C8alkyl, C1-C4haloalkyl, C1-C4alkoxy, C3-C8alkenyl, C3-C8alkynyl or benzyl, it being possible for benzyl in turn to be mono-to penta-substituted by halogen or mono-, di-or tri-substituted by C,-C4alkyl, C1-4haloalkyl, C1-C4alkoxy, -CN, -NO2, C,-C8alkylthio, C1-C8alkylsulfinyl or C,-C8alkylsulfonyl ; R57 is C1-C8alkyl, C,-C4haloalkyl, phenyl, benzyl or naphthyl, it being possible for the latter three aromatic rings to be mono-to penta-substituted by halogen and/or mono-, di-or tri- substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4alkylamino, di (C,-C4alkyl) amino, -NH2, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C,-C4alkylsulfonyl ; R58 and R59 are each independently of the other C1-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl, benzyl or naphthyl, it being possible for the latter three aromatic rings to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4halo- alkyl, C,-C4alkoxy, C,-C4alkylamino, di (C,-C4alkyl) amino,-NH2,-CN,-N02, C,-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; R60 and R6, are each independently of the other hydrogen or C,-C6alkyl ; R62, R63 and R64 are each independently of the others hydrogen or C,-C8alkyl, or R63 and R64 together form a C2-C5alkylene bridge; R65; Rus, R67, R68 R69 and R70 are each independently of the others hydrogen or C1-C8alkyl, or R65 and R66 together or R67 and R68 together or R69 and R70 together form a C2-C5alkylene bridge; and/or each R2 independently is C,-CBalkyl, or C,-C8alkyl mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by -CN, -N3, -SCN, -NO2, -NR71R72, -CO2R73, -CONR74R75, -COR76, -C(R77)-NOR78, -C (S) NR79R80, -C(C1-C4alkylthio)=NR81, -OH, -OR82, -SR83, -SOR84, -SO2R85, -O(SO2)R86, -N(R87)CO2R88, -N(R89)COR90, -S+(R91)2, -N+(R92)3, -Si(R93)3 or C3-C6cycloalkyl ; and/or each R2 independently is C,-C8alkyl substituted by a 5-to 7-membered heterocyclic ring system which can be aromatic or partially or fully saturated and which can contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, it being possible for such a heterocyclic ring system in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, hydroxy-C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkoxy-C1-C4alkyl, -CN, -NO2, -C1-C6alkylthio, C1-C6lkylsulfinyl or C,-C6alkylsulfonyl ; and/or each R2 independently is C2-C8alkenyl, or C2-C8alkenyl mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by-CN,-N02,-C02R94,-CONR95R96,-COR97, -C(R98) =NOR99, -C (S) NR100R101, -C(C1-C4alkylthio)=NR102, -OR103 -Si(R104) 3 or C3-C6cyclo- alkyl ; and/or each R2 independently is C2-C8alkynyl, or C2-C8alkynyl mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by-CN,-C02R, o5,-CONR, o6R, 07,-COR, o8, -C(R109)=NOR110, -C (S) NR111R112, -C(C1-C4alkylthio)=NR113, -OR114, -Si(R115) 3 or C3-C6cyclo- alkyl ; and/or each R2 independently is C3-C6cycloalkyl, or C3-C6cycloalkyl mono-to penta-substituted by halogen and/or mono-, di- or tri-substituted by -CN, -CO2R116, -CONR117R118, -COR119, -C (R, 20) =NOR121,-C (S) NRi22Ri23 or-C (C1-C4lkylthio)=NR124 ; and/or two adjacent R2 together form a C,-C7alkylene bridge, which can be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which can be mono-to penta- substituted by halogen and/or mono-, di-or tri-substituted by C,-C6alkyl or d-Cgaikoxy, the total number of ring atoms being at least 5 and at most 9; and/or two adjacent R2 together form a C2-C7alkenylene bridge, which can be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which can be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C6alkyl or C,-C6- alkoxy, the total number of ring atoms being at least 5 and at most 9; R71 is hydrogen or C,-C8alkyl ; R72 is hydrogen, C1-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C,-C4alkylsulfinyl or C,-C4alkylsulfonyl ; or Ryi and R72 together are a C2-C5alkylene chain, which can be interrupted by an oxygen or a sulfur atom; R73 is hydrogen, C1-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or C1-C8alkyl, C3-C8alkenyl or C3-C8alkynyl mono-to penta-substituted by halogen or mono-, di-or tri-substituted by C1-C4alkoxy or phenyl, it being possible for phenyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; R74 is hydrogen or C1-C8alkyl ; R75 is hydrogen, C1-C8alkyl or C3-C7cycloalkyl, or C1-C8alkyl mono-, di-or tri-substituted by -COOH, C1-C8alkoxycarbonyl, C1-C6alkoxy or -CN ; or R75 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C,-C4alkylsulfonyl ; or R74 and R75 together form a C2-C5alkylene chain, which can be interrupted by an oxygen or sulfur atom; R76 is hydrogen, C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl ; R77 is hydrogen, C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl ; R78 is hydrogen, C1-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C1-C4haloalkyl or C3-C6haloalkenyl ; and R79 is hydrogen or C1-C8alkyl ; R80 is hydrogen or C1-C8alkyl, or Ci-Cgatky) mono-, di-or tri-substituted by-COOH, C1-C8alkoxycarbonyl or-CN; or Rso is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; or R79 and R80 together are C2-Csalkylene ; R81 is hydrogen or C,-Csalkyl ; R82 is-Si (C1-C6alkyl) 3, C,-Csalkyl, C3-C8alkenyl, C3-C8alkynyl, or C1-C8alkyl which is mono- to penta-substituted by halogen or mono-, di-or tri-substituted by-CN,-NH2, C,- C6alkylamino, di (C,-C6alkyl) amino or C,-C4alkoxy ; R83 is hydrogen, C1-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, or d-Cga) ky) which is mono-to penta-substituted by halogen or mono-, di-or tri-substituted by-CN,-NH2, C,-C6alkylamino, di (C1-C6alkyl) amino or C1-C4alkoxy ; R84, R85 and R86 are each independently of the others C1-C8alkyl C3-C8alkenyl or C3-C8- alkynyl, or C1-C8alkyl which is mono-to penta-substituted by halogen or mono-, di-or tri- substituted by-CN or C1-C4alkoxy ; R87 and R89 are each independently of the other hydrogen, C1-C8alkyl or C1-C8alkoxy ; R88 is Cl-C8alkyl ; Rgo is hydrogen or C1-C8alkyl ; R91 is Cl-C4alkyl ; R92 and R93 are each independently of the other C1-C6alkyl ; R94 is hydrogen, or C,-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, each of which can be mono-to penta-substituted by halogen or mono-, di-or tri-substituted by C1-C4alkoxy or phenyl, it being possible for phenyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C,-C4alkylsulfinyl or C1-C4alkylsulfonyl ; R95 is hydrogen or C,-C8alkyl ; R96 is hydrogen or C1-C8alkyl, or C,-CBalkyl mono-to penta-substituted by halogen or mono-, di-or tri-substituted by-COOH, C,-C8alkoxycarbonyl or-CN ; or R96 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; or R95 and R96 together are C2-C5alkylene ; R97 and R98are each independently of the other hydrogen, C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl ; Rgg is hydrogen, C1-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C1-C4haloalkyl or C3-C6haloalkenyl ; Rloo is hydrogen or C,-C8alkyl ; Rlol is hydrogen or C1-C8alkyl, or C1-C8alkyl mono-, di-or tri-substituted by-COOH, C1-C8alkoxycarbonyl or-CN; or Rlol is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; or Rloo and R101 together are C2-C5alkylene ; Rio2 is hydrogen or C1-C8alkyl ; Rions is hydrogen, C1-C8alkyl, -Si (C,-C6alkyl) 3, C3-C8alkenyl or C3-C8alkynyl ; R104 is C,-C6alkyl ; Rio5 is hydrogen, or C1-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, each of which can be mono-to penta-substituted by halogen or mono-, di-or tri-substituted by C1-C4alkoxy or phenyl, it being possible for phenyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; Rice is hydrogen or C1-C8alkyl ; R, 07 is hydrogen or C1-C8alkyl, or C,-Csalkyl mono-, di-or tri-substituted by-COOH, C1-C8alkoxycarbonyl or-CN, or Rio7 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; or Rice and R107 together are C2-C5alkylene ; Rice is hydrogen, C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl ; R109 is hydrogen, C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl ; R110 is hydrogen, C1-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C1-C4haloalkyl or C3-C6haloalkenyl ; roll is hydrogen or C1-C8alkyl; R, 12 is hydrogen or C1-C8alkyl, or C1-C8alkyl mono-, di-or tri-substituted by-COOH, C,-C8alkoxycarbonyl or-CN; or R112 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; or Rill and R"2 together are C2-C5alkylene ; R, 13 is hydrogen or C1-C8alkyl ; R114 is hydrogen, C1-C8alkyl, -Si (C1-C6alkyl) 3, C3-C8alkenyl or C3-C8alkynyl ; Rus is Cl-C6alkyl ; Rue is hydrogen, or C1-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, each of which can be mono-to penta-substituted by halogen or mono-, di-or tri-substituted by C1-C4alkoxy or phenyl, it being possible for phenyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C,-C4alkylsulfinyl or C1-C4alkylsulfonyl ; R, 17 is hydrogen or C1-C8alkyl ; Rng is hydrogen or C,-Csalkyl, or C1-C8alkyl mono-, di-or tri-substituted by-COOH, C,-C8alkoxycarbonyl or-CN; or Rns is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; or R, and R118 together are C2-C5alkylene ; Rug is hydrogen, C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl ; R120 is hydrogen, C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl ; R121 is hydrogen, C1-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C1-C4haloalkyl or C3-C6haloalkenyl ; R112 is hydrogen or C1-C8alkyl ; R, 23 is hydrogen or C1-C8alkyl, or C,-C8alkyl mono-, di-or tri-substituted by-COOH, C1-C8alkoxycarbonyl or-CN; or R, 23 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl ; or R122 and R123 together are C2-C5alkylene ; and R124 is hydrogen or C1-C8alkyl ; X, and X2 are each independently of the other hydrogen, or C1-C8alkyl, C2-C8alkenyl or C2-CBalkynyl, each of which can be mono-to penta-substituted by halogen or mono-, di-or tri-substituted by-CN, C1-C4alkoxy, -OH, -OC(O) CH3, -OC (O) C6H5,-OCH2C6H5 or -OCH2CH=CH2 ; or X, and X2 are each independently of the other halogen, -CN, -NO2, -COOR125, -CH0, -COR126, -CH (OH) R127, -CH(OR128)R129 acetoxy, C1-C8alkoxy, C,-C8haloalkoxy, C3-C8alkenyloxy, C3-C8alkynyloxy, C1-C8alkylthio, C1-C8haloalkylthio, C3-C8alkenylthio, C3-C8alkynylthio, C1-C8alkylsulfinyl, C1-C8haloalkylsulfinyl, C3-C8alkenylsulfinyl, C3- CBalkynylsulfinyl, C,-C8alkylsulfonyl, C,-C8haloalkylsulfonyl, C3-C8alkenylsulfonyl, C3- CBalkynylsulfonyl, benzoyloxy, benzyloxy, benzylthio, phenoxy, phenylthio, phenylsulfinyl, benzylsulfinyl, phenylsulfonyl, benzylsulfonyl or phenyl, it being possible for the last- mentioned 10 aromatic rings in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by-CN, C1-C4alkoxy, C1-C4alkyl or C1-C4haloalkyl, or X, and X2 are each independently of the other-C (O) N (R130)R131 ; R125 is hydrogen, or C1-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, each of which can be mono-to penta-substituted by halogen or mono-, di-or tri-substituted by-CN or C1-C4alkoxy, or is benzyl, which in turn can be mono-to penta-substituted by halogen and/or mono-, di-or tri- substituted by-CN, C,-C4alkyl, C,-C4haloalkyl or C1-C4alkoxy ; R126, R127 and R129 are each independently of the others C1-C8alkyl, C2-C8alkenyl or C2-C8alkynyl, each of which can be mono-to penta-substituted by halogen or mono-, di-or tri-substituted by-CN or C1-C4alkoxy ; R128 is C1-C8alkyl, C3-C8alkenyl or C3-CBalkynyl, each of which can be mono-to penta- substituted by halogen or mono-, di-or tri-substituted by-CN or C1-C4alkoxy, or is benzyl, which in turn can be mono-to penta-substituted by halogen and/or mono-, di-or tri- substituted by-CN, Chalky), C,-C4haloalkyl or C,-C4alkoxy ; Rn30 and R, 3, are each independently of the other hydrogen, or C1-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, each of which can be mono-to penta-substituted by halogen or mono-, di-or tri-substituted by-CN or C,-C4alkoxy, or is phenyl, which in turn can be mono-to penta- substituted by halogen and/or mono-, di-or tri-substituted by-CN, C,-C4alkyl, C,-C4haloalkyl or C1-C4alkoxy ; or R130 and R13l together with the nitrogen atom to which they are bonded form a three-to eight-membered saturated, partially unsaturated or fully unsaturated heterocyclic ring, and to the agrochemically acceptable salts, N-oxides and all stereoisomers and tautomers of the compounds of formula 1.

In the nomenclature used for the present herbidically active phenoxy- (E)-propenylphenyl derivatives, the"- (E)-" is intended to refer explicitly to the trans double-bond isomers in accordance with the geometry of the propenyloxy bridging members shown below : The trans-geometry shown above is intended to apply irrespective of the choice of double- bond substituents X, and X2 within the scope of the given definition. For example, there are also included those isomeric compounds of formula I wherein the substituents X, and X2 are different from one another and X, and/or X2 are other than hydrogen, and are termed cis double-bond isomers in accordance with the Cahn-Ingold-Prelog system. The Cahn-Ingold- Prelog system weights two groups of different substituents at sp2-hybridised carbon atoms, e. g. X, and-O-C (R3) R4-, and X2 and phenyl in accordance with a defined, predetermined set of sequence rules (cf. Angew. Chem. Int. Ed. Engl. 5,385-415 (1966) ).

Thus in certain cases wherein X, is, for example,-NO2 and X2 is hydrogen, or X, is hydrogen and X2 is, for example,-COOR12st cis double-bond isomers can also be included within the scope of the present compounds of formula I designated"- (E)-".

In brief, those cis double-bond isomers which, by virtue of the choice of X, and/or X2 within the scope of the given definition and in accordance with the Cahn-lngold-Prelog system, have the two highest weighted substituents arranged on the same side of the double bond are likewise be included herein.

Two examples illustrate this situation: (see also Jerry March in"Advanced Organic Chemistry, Reactions, Mechanisms, and Structure", second edition, 1977, Mc Graw-Hill Book Company, pages 113-117).

When n is 0, all the free valencies on the phenoxy ring of the compounds of formula I are occupied by hydrogen. When m is 1,2, 3,4 or 5, the 5 potential valencies on the phenyl- alkene ring of the compounds of formula I are occupied independently of one another once, twice, three times, four times or five times by the substituents indicated under R2. Accord- ingly in the phenylalkene ring at least one valency is occupied by a substituent defined under R2 Examples of substituents that are formed when Rs and R6 together or R18 and R, g together or R36 and R37 together or R74 and R7s together are a C2-Csalkylene chain which can be interrupted by an oxygen or a sulfur atom are piperidine, morpholine, thiomorpholine and pyrrolidine.

Examples of heterocyclic ring systems which can be aromatic or partially or fully saturated in the definition of R2 are: The alkyl groups appearing in the definitions of substituents can be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, and also the isomers of pentyl, hexyl, heptyl and octyl.

Alkenyl and alkynyl groups can likewise be straight-chain or branched, this applying also to the alkyl, alkenyl and alkynyl moiety of hydroxyalkyl, cyanoalkyl, alkylcarbonyl, alkyl- carbonylalkyl, alkoxycarbonyl, alkenyloxyalkyl, alkynyloxyalkyl, alkylthioalkyl, alkoxyalkyl, alkylamino, dialkylamino, phenylalkyl and e. g. the groups-C (Rao) =NOR11 and -CR62 (OR63) OR64.

Halogen is fluorine, chlorine, bromine and iodine, preferably fluorine and chlorine.

Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2, 2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, penta- fluoroethyl, 1, 1-difluoro-2, 2, 2-trichloroethyl, 2,2, 3, 3-tetrafluoroethyl and 2,2, 2-trichloroethyl ; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichloro- fluoromethyl.

As haloalkenyl there come into consideration, for example, alkenyl groups mono-or poly- substituted by halogen, halogen being in particular bromine, iodine and especially fluorine and chlorine, for example 2-and 3-fluoropropenyl, 2-and 3-chloropropenyl, 2-and 3-bromo- propenyl, 2,3, 3-trifluoropropenyl, 2,3, 3-trichloropropenyl, 4,4, 4-trifluoro-but-2-en-1-yl and 4,4, 4-trichloro-but-2-en-1-yl. Of the alkenyl radicals mono-to penta-substituted by halogen special preference is given to those having a chain length of 3 or 4 carbon atoms. The alkenyl groups can be substituted by halogen at saturated or unsaturated carbon atoms.

As haloalkynyl there come into consideration, for example, alkynyl groups mono-to penta- substituted by halogen, halogen being bromine, iodine and especially fluorine and chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3, 3-trifluoropropynyl and 4,4, 4-trifluoro-but-2-yn-1-yl. Of the alkynyl radicals mono-to penta-substituted by halogen special preference is given to those having a chain length of from 3 to 5 carbon atoms.

Alkylcarbonyl is especially acetyl and propionyl.

Cyanoalkyl is, for example, cyanomethyl, cyanoethyl, cyanoeth-1-yl and cyanopropyl.

Hydroxyalkyl is, for example, 2-hydroxyethyl, 3-hydroxypropyl and 2, 3-dihydroxypropyl.

Alkoxy groups have preferably a chain length of from 1 to 6, especially from 1 to 4, carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy, and also the pentyloxy and hexyloxy isomers; preferably methoxy and ethoxy.

Alkoxy, alkenyl, alkynyl, alkoxyalkyl, alkylthio, alkylthioalkyl, alkylsulfonyl, alkylsulfonylalkyl, alkylsulfinyl, alkylsulfinylalkyl, alkoxycarbonyl, alkenylthio, alkenylsulfonyl, alkenylsulfinyl, alkynylsulfonyl, alkynylthio and alkynylsulfinyl groups are derived from the mentioned alkyl radicals. The alkenyl and alkynyl groups can be mono-or poly-unsaturated. Alkenyl is to be understood as being, for example, vinyl, allyl, methallyl, 1-methylvinyl or but-2-en-1-yl.

Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, 2-methylbutyn-2-yl or but-3-yn-2-yl.

Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2, 2- trifluoroethoxy, 1,1, 2, 2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2, 2- trichloroethoxy.

Alkylthio groups have preferably a chain length of from 1 to 4 carbon atoms. Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butyl- thio or tert-butylthio, preferably methylthio or ethylthio. Alkylsulfinyl is, for example, methyl- sulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec- butylsulfinyl or tert-butylsulfinyl ; preferably methylsulfinyl or ethylsulfinyl. Alkylsulfonyl is, for example, methytsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl ; preferably methylsulfonyl or ethyl- sulfonyl.

Haloalkylsulfonyl is, for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoro- methylsulfonyl, chloromethylsulfonyl, trichloromethylsulfonyl, 2-fluoroethylsulfonyl, 2,2, 2- trifluoroethylsulfonyl or 2,2, 2-trichloroethylsulfonyl.

Alkoxyalkyl groups have preferably from 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl.

Alkylamino is, for example, methylamino, ethylamin and the propyl-and butyl-amino isomers.

Dialkylamino is, for example, dimethylamino, diethylamino and the dipropyl-and dibutyl- amino isomers.

Cycloalkyl radicals that come into consideration as substituents are, for example, cyclo- propyl, cyclobutyl, cyclopentyl and cyclohexyl.

Corresponding meanings can also be assigned to the substituents in combined definitions, for example alkoxyalkoxycarbonyl, alkoxycarbonylalkyl, alkenyloxycarbonyl, R, 30-, alkyl- sulfinylalkyl,-C (R24) =NOR2s,-C (C,-C4alkylthio) =NR28,-N=C (OR60) R6"-CR62 (OR63) OR64 and - ( [CO] pR, 16) COR47.

Substituents wherein two adjacent R, together form a C,-C7alkylene bridge which can be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which can be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C6alkyl or C,-C6alkoxy, the total number of ring atoms being at least 5 and at most 9, and/or two adjacent R, together form a C2-C7alkenylene bridge which can be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which can be mono- to penta-substituted by halogen and/or mono-, di-or tri-substituted by Ci-Cgatkyi or Ci-Ce- alkoxy, the total number of ring atoms being at least 5 and at most 9, have, for example, the following structures: Substituents wherein two adjacent R2 together form a C,-C7alkylene bridge which can be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which can be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by Cl-C6- alkyl or C,-C6alkoxy, the total number of ring atoms being at least 5 and at most 9, and/or two adjacent R2 together form a C2-C7alkenylene bridge which can be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which can be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C6alkyl or C,-C6- alkoxy, the total number of ring atoms being at least 5 and at most 9, have, for example, the following structures: The invention relates also to the salts which the compounds of formula I are able to form especially with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases. Suitable salt-formers are described, for example, in WO 98/41089.

Among the alkali metal and alkaline earth metal hydroxides as salt formers, special mention should be made of the hydroxides of lithium, sodium, potassium, magnesium and calcium, but especially the hydroxides of sodium and potassium.

Examples of amines suitable for ammonium salt formation include ammonia as well as primary, secondary and tertiary C,-C, 8alkylamines, C,-C4hydroxyalkylamines and C2-C4- alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four butylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine, octyl- amine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octa- <BR> <BR> <BR> decylamine, methylethylamine, methylisopropylamine, methylhexylamine, methyinonylamine,<BR> <BR> <BR> <BR> <BR> <BR> methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyl- octylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propyl- amine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, N, N- diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2, 3-dimethylbutenyl-2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n- butylamine, triisobutylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine ; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morph- oline, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o-, m-and p-toluidines, phenylen- diamines, benzidines, naphthylamines and o-, m-and p-chloroanilines ; but especially triethylamine, isopropylamine and diisopropylamine.

Preferred quaternary ammonium bases suitable for salt formation correspond e. g. to the formula [N (RaRbRcRd)] OH wherein Ra, Rb, Rc and Rd are each independently of the others C1-C4alkyl. Other suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.

Preferred compounds of formula I are those wherein R82 is-Si (C,-C6alkyl) 3, C3-C8alkenyl, C3- C8alkynyl, or C,-C8alkyl which is mono-to penta-substituted by halogen or mono-, di-or tri- substituted by-CN,-NH2, C,-C6alkylamino, di (C,-C6alkyl) amino or C,-C4alkoxy ; Also preferred compounds of formula I are those wherein R2 is a 5-to 7-membered heterocyclic ring system which can be aromatic or partially or fully saturated and which can contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, it being possible for such a heterocyclic ring system in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C4alkyl, C,-C4haloalkyl, hydroxy-C,-C4alkyl, C,- C4alkoxy, C,-C4alkoxy-C,-C4alkyl,-CN,-NO2, C,-C6alkylthio, C,-C6alkylsulfinyl or C,-C6alkylsulfonyl ; and/or each R2 independently is C,-C8alkyl substituted by a 5-to 7-membered heterocyclic ring system which can be aromatic or partially or fully saturated and which can contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, it being possible for such a heterocyclic ring system in turn to be mono-to penta-substituted by halogen and/or mono-, di-or tri-substituted by C,-C4alkyl, C,-C4haloalkyl, hydroxy-C,-C4alkyl, C,-C4alkoxy, C,-C4alkoxy-C,-C4alkyl,-CN,-N02, C,-C6alkylthio, C,-C6alkylsulfinyl or C,-C6alkylsulfonyl.

Preference is also given to compounds of formula I wherein n = 0, or each Ri independently is halogen,-CN,-N02,-C (R10)=NOR11, -OR13, -SO2R16, -OSO2R17, C1-C8alkyl or C2-C8- alkenyl, and/or C,-C8alkyl mono-, di-or tri-substituted by halogen or-CN; Rio is hydrogen or C1-C4alky ; and R"is C,-C8alkyl, wherein R, 3, R, 6 and R17 are as defined for formula 1.

Preference is likewise given to compounds of formula I wherein Roi is hydrogen, C1-C8alkyl, or C1-C8alkyl mono-to penta-substituted by halogen or mono-, di-or tri-substituted by-CN.

Of those compounds, special preference is given to those wherein Roi is C1-C4alkyl, or C1-C4alkyl mono-, di-or tri-substituted by halogen or mono-substituted by-CN.

Preference is also given to those compounds of formula I wherein m = 0, or each R2 independently is halogen,-CN,-SCN,-OCN,-N3,-CONR36R37,-C (R38) =NOR39, -COR40, -OR41, -SO2R45, -N([CO]R46)COR47, -N(R56)SO2R57, -N(SO2R58)SO2R59, -N=C(OR60)R61 or C1-C6alkyl, and/or C1-C8alkyl mono-, di-or tri-substituted by halogen,-CN,-N3,-SCN, -CONR74R75, -COR76, -C(R77)=NOR78, -C (S) NR79R8o,-OR82,-SOR84,-S02R85 or - N (R89) COR90, wherein R36 to R41, R45 to R47, R56 to Rei, R74 to R8o, R82, R84, R85, R89, Ago and the suffix p are as defined for formula 1.

Important compounds of formula I are those wherein n = 0, or each R, independently is halogen,-CN,-N02,-C (R10)=NOR11, -OR13, -SO2R16, -OSO2R17, C1-C8alkyl or C2-C8alkenyl, and/or C,-C8alkyl mono-, di-or tri-substituted by halogen or-CN; m = 0, or each R2 independently is halogen,-CN,-SCN,-OCN,-N3,-CONR36R37,-C (R38) =NOR39,-COR4o, -OR41, -OSO2R45, -N([CO]pR46)COR47, -N(R56)SO2R57, -N(SO2R58)SO2R59, -N=C(OR60)R61 or C,-CBalkyl, and/or C,-C8alkyl mono-, di-or tri-substituted by halogen,-CN,-N3,-SCN, -CONR74R75, -COR76, -C(R77)-NOR78, -C (S) NR79Rao,-OR82,-SOR84,-S02Rs5 or -N(R89)COR90 ; Rio is hydrogen or C1-C4alkyl ; and R11 is C1-C8alkyl, wherein R13, R16, R17, R36 to R41, R45 to R47, R56 to R61, R74 to R80, R82, R84, R85, R89, R9o and the suffix p are as defined for formula 1.

Also important are compounds of formula I wherein Roi is hydrogen, C,-Caalkyl, or C1-C8alkyl mono-to penta-substituted by halogen or mono-, di-or tri-substituted by-CN; m = 0, or each R2 independently is halogen,-CN,-SCN,-OCN,-N3,-CONR36R37,-C (R38) =NOR39,-COR4o, -OR41, -OSO2R45, -N([CO]pR46)COR47, -(R56)SO2R57, -N(SO2R58)SO2R59, -N=C(OR60)R61 or C,-C8alkyl, and/or C,-C8alkyl mono-, di-or tri-substituted by halogen,-CN,-N3,-SCN, -CONR74R75, -COR76, -C(R77)=NOR78, -C (S) NR79R8o,-OR82,-SOR84,-S02R85 or -N(R89)COR90, wherein R36 to R41, R45 to R47, R56 to R6,, R74 to R80, R82, R84, R85, R89, R90 and the suffix p are as defined for formula 1.

The compounds of formula I can be prepared analogously to known compounds, for example bv reactina a compound of formula II wherein Roi, R1 and n are as defined for formula 1, either a) according to Route A) with a compound of formula III wherein R2, R3, R4, m, X, and X2 are as defined for formula I and L is a leaving group, for example halogen, e. g. chlorine, bromine or iodine,-OS (0) 2CH3 (mesylate),-OS (0) 2C6H4-4- CH3 (tosylate),-OS (0) 2C6H5 or-OS (0) 2CF3 (triflate), in the presence of a base in an inert solvent, or under phase transfer catalytic conditions, or b) according to Route B) with a compound of formula III wherein R R3, R4, m, X1 and X2 are as defined and L is an acyloxy group, for example - OC (O) CH3,-OC (O) CsHs or-OC (O) OC2H5, in the presence of transition metal catalysts in inert solvents, or c) according to Route C) with a compound of formula III wherein R2, R3, R4, m, Xi and X2 are as defined and L is an OH function, in accordance with the Mitsunobu reaction.

Those processes for the preparation of compounds of formula I are illustrated in Reaction Scheme 1. Reaction scheme 1 For L = leaving group e. g. halogen, mesylate, tosylat or triflate : Route A : base e. g. K2C03, solvent e. g. THF, or (RtOH + Xg phase transfer conditions , 6 1 1 OH + c For L = acyloxy : ., (Rz) Route B) : transition metal cat. e. g. R3 R4 X2 m Pd (OAc) 2/C6HsCN, solvent e. g. THF 2 For L = OH : II lil Route C) : Mitsunobu reaction According to Reaction Scheme 1, Route A), the compounds of formula I can be obtained, for example, by alkylation of the phenol of formula 11 with a compound of formula III under typical alkylation conditions in the presence of a base in an inert organic solvent either with cooling of the reaction mixture to temperatures < 15°C, at room temperature (15-25°C) or with heating to the reflux temperature of the solvent used.

Suitable bases are, for example, carbonates, e. g. potassium carbonate or sodium hydrogen carbonate, alkali metal or alkaline earth metal hydroxides, for example sodium or potassium hydroxide, alcoholates, for example sodium methanolate or sodium tert-butanolate, amines, for example triethylamine, pyridine or Hunig's base.

Solvents that come into consideration include ethers, for example tetrahydrofuran (THF), dioxane or dimethoxyethane, ketones, for example acetone or methyl ethyl ketone, nitriles, for example acetonitrile, amides, for example N, N-dimethylformamide (DMF) or dimethyl- acetamide, sulfoxides, for example dimethyl sulfoxide (DMSO), or 1-methyl-2-pyrrolidone, and also aromatic hydrocarbons, for example totuene or xylenes, and halogenated hydrocarbons, for example 1, 2-dichloroethane. Alcohols, for example ethanol or tert-butanol, are preferably used together with the corresponding alkali metal alcoholates.

Suitable leaving groups for Route A) in Reaction Scheme 1 are, for example, halogen, e. g. chlorine, bromine or iodine, and also-OS (O) 2CH3,-OS (O) 2C6Hs,-OS (O) 2-C6H4-4-CH3 or -OS (0) 2CF3 Such base-catalysed alkylations are described, for example, in Synthesis 2001,1959 ; Organic Letters 2001 (3), 1649 ; J. Org. Chem. 2000 (65), 3085; ibid. 1993 (58), 2068; Anticancer Research 1999 (19), 3757; Bioorganic & Medicinal Chemistry Letters 1999 (9), 3439; Chem. Communic. 1998,1639 ; and Tetrahedron Lett. 1997 (38), 7337.

The alkylation under phase transfer catalytic conditions in accordance with Route A) in Reaction Scheme 1 is described, for example, in Tetrahedron Lett. 2000 (41), 6893; and EP-A-0 636 367, the base being used in solid form or in aqueous phase together with an inert, lipophilic solvent, e. g. aromatic or halogenated hydrocarbons, for example toluene, benzene or dichloromethane, and a phase transfer catalyst. Examples of phase transfer catalysts are tetrabutylammonium salts, for example tetrabutylammonium chloride, bromide, hydroxide or tetrafluoroborate or tetrabutylammonium hydrogen sulfate.

For L as an acyloxy group in a compound of formula 111, for example-OC (O) CH3, -OC (O) C6H5 or-OC (O) OCZHS, the alkylation reaction can be carried out in accordance with Reaction Scheme 1, Route B), using transition metal catalysts, e. g. palladium (lI) acetate/ phenylcyanide (Pd (OAc) 2/C6H5CN), 1, 5-diphenyl-1, 4-pentadien-3-one palladium/triphenyl- phosphine (Pd (dba) 2/P (C6Hs) 3) or tetrakis (triphenylphosphine) palladium (Pd [ (P (C6H5) 314), preferably in an ether, for example tetrahydrofuran (THF), as solvent.

Such alkylation reactions are described, for example, in Topics in Catalysis 2000 (13), 311; Synthetic Communic. 2000 (30), 3955; J. Am. Chem. Soc. 2000 (122), 3534; and Synlett 1998,741.

A further method by which the compounds of formula I can be prepared is carried out with the aid of the Mitsunobu reaction analogously to that described in J. Chem. Soc. , Perkin Trans I 2000, 4265; WO 00/63153; Chem. Communic. 2000, 475; or Chem. Lett. 1986, 2097. That synthesis route is shown in diagrammatic form as Route C) in Reaction Scheme 1.

Accordingly, the mixture consisting of the phenol of formula 11, allyl alcohol of formula III wherein L is a OH function, and triphenylphosphine in an inert solvent is reacted with an aza- dicarboxylic acid derivative either with cooling (temperature < 15°C), at room temperature (15-25°C) or with heating up to the reflux temperature of the solvent used. Suitable inert solvents are e. g. aromatic hydrocarbons, for example toluene or the xylene isomers, ethers, for example THF, dioxane or 1,2-dimethoxyethane ; suitable azadicarboxylic acid derivatives are e. g. azadicarboxylic acid dimethyl ester, diethyl ester or diisopropyl ester.

The allyl alcohols of formula III wherein L is a OH function or a derivative thereof that are used can be prepared according to standard methods in a manner analogous to that described e. g. in Angew. Chem., Int. Ed. 2001 (40), 1439; Tetrahedron Lett. 2000 (41), 6893; ibid. 1996 (37), 2507; J. Org. Chem. 1996 (61), 7139; or J. Org. Chem. 1994 (59), 4143. Such coupling reactions have become known e. g. as Stille, Suzuki or Hiyama coupling. Reaction Scheme 2 shows such a coupling reaction in diagrammatic form.

Reaction Scheme 2 xI Z OC'C C, M + Y c c + y 30 R3 R 4 X2 2 M IV : M= e. g.-Sn (CH3) 3,-B (OH) 2, V : Y= Br, I,-OS (0) 2CF3 - B (OCH3) 2 or-Si (C6H5) 3 cat. e. g. PdC12 (CH3CN) 2. Xr inert solvent e. g. L THF, base e. g. K3P04 , C C C Rs Ra X2 RZ) m III : L=-O-Z, wherein Z= C6H5C (O)-, CH30CH2-, -Si (CH3) 2tert-butyl or is c. o In the above Reaction Scheme, R2, R3, R4, m, X, and X2 in the compounds of formulae IV and V are as defined for formula I and Z in the compound of formula IV is an oxygen- protecting group, e. g. benzoyl, methoxymethyl (MOM), tetrahydropyranyl or tert-butyl- dimethylsilyl (TBDMS,-Si (CH3) 2-tert-butyl), which can readily be introduced and removed again by customary standard methods.

M in the compound of formula IV is a trivalent Sn or Si radical or a divalent B radical, for example-Sn (CH3) 3,-Sn (n-butyl) 3,-Sn (C6H5) 3,-Si (CH2CH3) 3,-Si (C6H5) 3,-Si (CH3) CI2, BBN (9-borabicyclo [3. 3.1] nonane),-B (C6H") 2 or-B [CH (CH3) CH (CH3) 2] 2 Y in the compound of formula V is, for example, bromine, iodine or-OS (0) 2CF3. The coupling reaction according to Reaction Scheme 2 is preferably effected in an inert organic solvent, for example an ether, e. g. THF or dioxane, an amide, for example N, N-dimethyl- formamide (DMF), N, N-dimethylacetamide or N-methylpyrrolidone (NMP), or an aromatic hydrocarbon, for example toluene or benzene, at room temperature or with heating. Suitable catalysts are, for example, palladium/C charged with As (C6H5) 3, palladium (II) chloride diacetonitrile complex (PdCl2 (CH3CN) 2), tetrakis (triphenylphosphine) palladium (Pd [P (C6H5) 3] 4), palladium bis (triphenylphosphine) dichloride (PdClz [P (C6H5) 3] 2), 1, 5- diphenyl-1, 4-pentadien-3-one palladium complex/P (C6Hs) 3, [Pd2 (dba) 3] CHCI3P (2- furyl) 3/Cul, it generally being possible to use copper iodide as co-catalyst. In certain cases it is also possible to use lithium salts, for example lithium chloride (LiCI).

Suitable bases for such a coupling reaction are, for example, tripotassium phosphate (K3PO4) or alcoholates, for example sodium ethanolat or potassium tert-butanolate.

The compounds of formula IV wherein R3, R4, X, and X2 are as defined for formula 1, Z is an oxygen-protecting group, e. g. benzoyl, methoxymethyl (MOM), tetrahydropyranyl or tert-butyl-dimethylsilyl (TBDMS, -Si (CH3) 2-tert-butyl), and M is a trivalent Sn or Si radical or a divalent B radical such as e. g.

-Sn (CH3) 3,-Si (C6H5) 3 or-B (OCH3) 2 can be prepared in accordance with known methods, as described e. g. in J. Org. Chem. 1967 (32), 2634; ibid. 1990 (55), 1857; ibid. 1980 (45), 4264; ibid. 1987 (52), 4421; ibid 1992 (57), 5250 ; Synlett 1992,489 ; ibid. 1998,1255 ; Chem.

Communic. 1994,1777 ; Org. Synth. 75,78 (1998); J. Chem. Soc., Perkin Trans 11997 (7), 997; ibid. 1998,2865 ; M. Pereyre et a/.,"Tin in Organic Synthesis", Butterworths, London, 1987 ; Tetrahedron 1989 (45), 363.

Reaction Scheme 3 shows by way of illustration three synthesis routes for the preparation of compounds of formula IV.

Reaction Scheme 3 Route D) : y X solvent e. g. THF, Z-O C C cat. e. g. H. PtC,. 6H. O C C'+ H-Si (CH3) CIZ 2 C w. C R3 R4 R3 R4 X2 X : Z=H or protecting group IV : M=-Si (CH3) C'2 ; e. g.-Si (CH3) 2-tert-C4Hg ; X, =H X2= e. g. H, alkyl, haloalkyl, cyanoalkyl, alkoxyalkyl Route E) : 2 \ C'solvent e. g. THF z-p I C + H-Sn (C4H9) s R R 3R4/\ 1 X : Z=H or protecting group e. g.-Si (CH3) 2-tert-C4H9 ; IV : M=-Sn (C4H9) 3 ; X2=H X, =H Route F) : X X, Z-O % C solvent e. g. THF xc, C + H-B (OCH3) z C. CC, M R34 Ra 3 Y 2 X : Z=H or protecting group IV : M=-B (OCH3) 2 or e. g.-Si (CH3) 3 X2= e. g. H, alkyl, haloalkyl, X, =H alkoxyalkyl According to Reaction Scheme 3, Route D), a compound of formula X wherein R3 and R4 are as defined for formula 1, X2 is hydrogen, C,-C8alkyl, or C,-C8alkyl substituted by halogen,-CN or C,-C4alkoxy, and Z is hydrogen or an 0-protecting group, e. g. -Si(CH3)2-tert-buty, -Si(C2H5) 3, benzoyl, benzyl, allyl or methoxymethyl (MOM), is reacted e. g. with methyl- dichlorosilane in an inert solvent, for example toluene, xylene, dichloromethane, 1, 2-dichloro- ethane, THF, dioxane or acetone either with cooling, at room temperature or with heating in the presence of a catalyst, e. g. Rh (cod) 2BF4/2-P (C6H5) 3, Pt (CH2=CH2) 2 (PCy3) or H2PtC16@6H2O, to form the desired target compound of formula IV wherein M is-Si (CH3) CI2, and X, is hydrogen.

According to Route E) in Reaction Scheme 3, a compound of formula X wherein R3, R4, X2 and Z are as defined can also be reacted with a trialkyltin hydride (=hydrostannylation), e. g.

H-Sn (C4H9) 3, in an inert solvent as indicated above under Route D) to form the desired target compound of formula IV wherein M is-Sn (C4H9) 3 and X, is hydrogen.

Finally, according to Route F) in Reaction Scheme 3, a compound of formula X wherein R3, R4, X2 and Z are as defined can be reacted by means of hydroborination with a borane derivative, e. g. H-B (OCH3) 2,9-BBN-H (9-borabicyclo [3.3. 1] nonane), Mes2B-H (dimesityl- borane), Sia2B-H (disiamylborane), Chx2B-H (dicyclohexylborane), pinacolborane or catecholborane, to form the desired alkylen boron compound of formula IV wherein M is e. g. -B (OCH3) 2 or-B (OH) 2 and X, is hydrogen. That reaction can be carried out without a solvent or in an inert solvent as indicated above, at room temperature or with heating, without or in the presence of a catalyst. A suitable catalyst is, for example, BH3-Et2NC6H5.

The allyl alcohols of formula III wherein R2, m, X, and Xz are as defined for formula I and R3 and R4 are hydrogen can also be readily obtained by means of reduction of the correspond- ing cinnamic acid derivatives of formula VI wherein R2, m, X, and X2 are as defined and R is hydrogen, C,-C4alkyl, allyl, unsubstituted or substituted benzyl,-Si (CH3) 3,-Si (iso-C3H7) 3 or -Si (CH3) 2-tert-butyl, in a manner analogous to that described e. g. in Org. Lett. 2001 (3), 739; ibid. 2000 (2), 3521; J. Org. Chem. 2000 (65), 7690; Tetr. Asymm. 2000 (11), 2801; or Helv.

Chim. Acta 2000 (83), 972. Reaction Scheme 4 shows such a reductive preparation method in diagrammatic form.

Reaction Scheme 4 reduction e. g. ROOC-C R2 HO C M LiAIH4, ether 11c X2 R3 Ra X2 vu III : R3, R4 = hydrogen halogenation or acylation sulfonylation L C/R2 C/Rz) \ m C \ m / C/\ C r \ Y \ T 4 X2 4 X 2 III : L= Cl, Br, I, tosylate, mesylate III : L= acyloxy e. g.-OC (O) CH3 or -OC (O) OC2H5 Suitable reducing agents are, for example, hydrides, e. g. lithium aluminium hydride or diisobutylaluminium hydride, in inert organic solvents, such as ethers, e. g. diethyl ether, THF or dioxane, aromatic or halogenated hydrocarbons, for example toluene or dichloromethane.

The halogenation of an alcohol of formula III can be carried out analogously to known standard halogenations. For example, bromination can be carried out with carbon tetra- bromide in the presence of triphenylphosphine (Synthesis 1998,1015-1018) in methylene chloride. Chlorination is carried out with mineral acids, for example with concentrated hydrochloric acid (J. Org. Chem. 1955 (20), 95) or with para-toluenesulfonic acid chloride (tosyl chloride, p-TsCI) in the presence of an amine, for example triethylamine, in a solvent, for example methylene chloride (Tetrahedron Lett. 1984 (25), 2295).

Sulfonylation of an alcohol of formula III is likewise a standard reaction in organic chemistry and can be carried out, for example, with a sulfonic acid chloride, for example mesyl chloride, methanesulfonic anhydride or para-toluenesulfonic acid chloride (p-TsCI) in the presence of a tertiary amine, for example triethylamine, or an aromatic amine, for example pyridine, in a solvent, for example a chlorinated hydrocarbon, for example carbon tetra- chloride or methylene chloride, or an amine, for example pyridine. Such reactions are generally known and are described, for example, in J. Org. Chem. 1997 (62), 8987; J. Het.

Chem. 1995 (32), 875-882; and Tetrahedron Lett. 1997 (38), 8671-8674.

The acylation of an alcohol of formula III can be carried out analogously to known standard acylations, for example with the corresponding acyl halides or anhydrides.

A large number of customary standard methods are known for the preparation of the sub- stituted cinnamic acid derivatives of formula Vl that are used. Some of those methods are shown in diagrammatic form by way of example in Reaction Scheme 5.

Reaction Scheme 5 introduction and conversion of functional groups according to standard processes e. g. electrophilic/nucleophilic aromatic substitution, H oxidation, reductionetc. X,, < ROOC-C ROOC-C RZ) m c c H X2 V) a V) Via Vl Heck reaction Wittig reaction (C6Hs) ap-C-COOR ex xi Xi1 I OHM onc Rz m R2) m VII V : Y= Br, I,-OS (O) ZCF3 VIII Vll V : Y= Br, I,-OS (0) 2CF3 Vlil For example, starting from compounds of formulae V and Vil wherein R is hydrogen, C,-C4alkyl, allyl ; benzyl unsubstituted or substituted on the aromatic ring;-Si (CH3) 3,-Si (iso- C3H7) or-Si (CH3) 2-tert-butyl, and Y is bromine, iodine or-OS (0) 2CF3, the Heck reaction is suitable as a method of synthesising compounds of formula VI.

Starting from the benzaldehyde of formula VIII, the Wittig reaction with the so-called Wittig reagent of formula IX is a further suitable method for synthesising compounds of formula VI, there generally being obtained (E)/ (Z) isomeric mixtures of the cinnamic acid derivatives of formula VI which can be separated into the pure (E) and (Z) isomers by known methods, e. g. by means of silica gel column chromatography, fractional crystallisation or distillation.

In such a method the substituents R2, m, X, and X2 in the starting compounds of formulae V, VII, VIII and IX are to be so selected within the scope of the meanings given for formula I that the substitution pattern or the reactivity of the starting compounds is compatible with the reaction to be carried out.

Finally, the functionalised cinnamic acid derivatives of formula Vl can be obtained from the known cinnamic acid derivatives of formula Vla, some of which are commercially available, for example by introduction and conversion of functional groups e. g. by means of electro- philic and/or nucleophilic aromatic substitution, substitution, oxidation and reduction.

All those methods of synthesis are standard in organic chemistry and are described, for example, in M. B. Smith, J. March in"March's Advanced Organic Chemistry", John Wiley, New York, 2001; R. C. Larock in"Comprehensive Organic Transformations", VCH, New York, Weinheim 1989; B. M. Trost & I. Fleming, Editors, "Comprehensive Organic Synthesis", Pergamon Press, Oxford 1991, Volumes 1-9; and B. S. Furniss et a/."Vogel's Textbook of Practical Organic Chemistry", Longman Scientific & Technical, 1989, Harlow.

For all four Reaction Schemes 1,2, 4 and 5 it is generally the case that the various substituents R, and R2 in compounds of formulae 11, III, V, VI and Vlil are either already present at the outset or can be introduced in succession only at a later stage of the reaction sequence e. g. by nucleophilic or electrophilic aromatic substitution and by suitable con- version of functional groups.

The following comments apply to the individual reaction steps in Reaction Schemes 1 to 5: The reactions to form compounds of formula I are advantageously performed in aprotic, inert organic solvents. Such solvents are hydrocarbons, such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons, such as dichloromethane, trichloromethane, tetra- chloromethane and chlorobenzene, ethers, such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran and dioxane, nitrites, such as aceto- nitrile and propionitrile, and amides, such as N, N-dimethylformamide, diethylformamide and N-methylpyrrolidinone. The reaction temperatures are preferably from-20°C to +120°C. The reactions generally proceed slightly exothermically and can generally be carried out at room temperature. In order to shorten the reaction time or to initiate the reaction, brief heating, up to the boiling point of the reaction mixture, can be carried out. The reaction times can like- wise be shortened by the addition of a few drops of base as reaction catalyst. Suitable bases are especially tertiary amines, such as trimethylamine, triethylamine, quinuclidine, 1,4-diaza- bicyclo [2.2. 2octane, 1, 5-diazabicyclo [4.3. 0] non-5-ene and 1, 5-diazabicyclo [5.4. 0] undec-7- ene, but it is also possible to use inorganic bases, such as hydrides, e. g. sodium or calcium hydride, hydroxides, such as sodium or potassium hydroxide, carbonates, such as sodium or potassium carbonate, or hydrogen carbonates, such as potassium or sodium hydrogen carbonate.

The compounds of formula I can be isolated in customary manner by concentration and/or evaporation of the solvent and can be purified by recrystallisation or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydro- carbons or chlorinated hydrocarbons.

Most of the starting compounds of formula 11 used in Reaction Scheme 1 for the preparation of compounds of formula I are known or they can be prepared analogously to known proc- esses.

The starting compounds of formulae IV, V, VIl, VIII, IX and X used in Reaction Schemes 2,3 and 5 are likewise known, some of them are commercially available or they can be prepared analogously to known processes.

For the use according to the invention of the compounds of formula 1, or of compositions comprising them, there come into consideration all methods of application customary in agriculture, for example pre-emergence application, post-emergence application and seed dressing, and also various methods and techniques such as, for example, the controlled release of active ingredient. For that purpose a solution of the active ingredient is applied to mineral granule carriers or polymerised granules (urea/formaldehyde) and dried. If required, it is also possible to apply a coating (coated granules), which allows the active ingredient to be released in metered amounts over a specific period of time.

The compounds of formula I can be used as herbicides in their unmodified form, that is to say as obtained in the synthesis, but they are preferably formulated in customary manner together with the adjuvants conventionally employed in formulation technology, for example into emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. Such formulations are described, for example, on pages 9 to 13 of WO 97/34485. As with the nature of the comp- ositions, the methods of application, such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circum- stances.

The formulations, that is to say the compositions, preparations or mixtures comprising the compound (active ingredient) of formula I or at least one compound of formula I and, usually, one or more solid or liquid formulation adjuvants, are prepared in known manner, e. g. by homogeneously mixing and/or grinding the active ingredients with the formulation adjuvants, for example solvents or solid carriers. Surface-active compounds (surfactants) can also be used in addition in the preparation of the formulations. Examples of solvents and solid carriers are given, for example, on page 6 of WO 97/34485.

Depending upon the nature of the compound of formula I to be formulated, suitable surface- active compounds are non-ionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties. Examples of suitable anionic, non-ionic and cationic surfactants are listed, for example, on pages 7 and 8 of WO 97/34485. In addition, the surfactants conventionally employed in formulation technology, which are described, inter alia, in"McCutcheon's Detergents and Emulsifiers Annual"MC Publishing Corp. , Ridgewood New Jersey, 1981, Stache, H.,"Tensid-Taschen- buch", Carl HanserVerlag, MunichNienna 1981, and M. and J. Ash,"Encyclopedia of Surfactants", Vol. 1-111, Chemical Publishing Co. , New York, 1980-81, are also suitable for the preparation of the herbicidal compositions according to the invention.

The herbicidal formulations generally contain from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of herbicide, from 1 to 99.9 % by weight, especially from 5 to 99.8 % by weight, of a solid or liquid formulation adjuvant, and from 0 to 25 % by weight, especially from 0.1 to 25 % by weight, of a surfactant. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations. The compositions can also comprise further ingredients, such as stabilisers, for example vege- table oils or epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), anti-foams, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers, and also fertilisers or other active ingredients.

The compounds of formula I are generally applied to plants or the locus thereof at rates of application of from 0.001 to 4 kg/ha, especially from 0.005 to 2 kg/ha. The concentration required to achieve the desired effect can be determined by experiment. It is dependent on the nature of the action, the stage of development of the cultivated plant and of the weed and on the application (place, time, method) and can vary within wide limits as a function of those parameters.

The compounds of formula I are distinguished by herbicidal and growth-inhibiting properties, allowing them to be used in crops of useful plants, especially cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, and also for non-selective weed control. The term"crops"is to be understood as including also crops that have been made tolerant to herbicides or classes of herbicides as a result of conventional methods of breeding or genetic techniques. The weeds to be controlled can be either monocotyledonous or dicotyledonous weeds, such as, for example, Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Panicum, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Euphorbia, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.

The following Examples further illustrate but do not limit the invention.

Preparation Examples Example P1 : Preparation of 3- [2- (cvanomethvl) phenyll-2- ror) enoic acid ter-butyl ester 10.0 g of 3-bromophenylacetonitrile, 8.5 ml of acrylic acid ter-butyl ester and 7.74 ml of triethylamine are introduced into 60 ml of dry N, N-dimethylformamide (DMF) under an argon atmosphere. With stirring, the mixture is heated to 80°C, 60 mg of palladium (II) acetate and 160 mg of tri-o-tolylphosphine are added and after one hour subsequent operations are carried out without protective argon gas. The reaction mixture is heated to 120°C and then stirred for 4 hours. Thin-layer analysis of a sample shows that the starting compounds are no longer present. 1 M aqueous hydrochloric acid and diethyl ether are added to the mixture.

After extraction by shaking and separation of the phases, the organic phase is washed with brine, dried over sodium sulfate, filtered, and completely evaporated in vacuo, yielding as crude product 12.7 g of a yellow liquid which, after purification by column chromatography over silica gel (eluant : hexane/ethyl acetate 2/1), yields 9.82 g of a yellow liquid. According to NMR it is a mixture of 4 parts of the desired target compound and 1 part of the bromide used.

'H-NMR (TMS, Ceci3) : 1.54 ppm (s, 9H); 3.77 ppm (s, 2H); 6.40 ppm (d, 1H); 7.27- 7.50 ppm (m, 4H); 7.56 ppm (d, 1H).

Example P2: Preparation of 3-f2- (cvanomethyl) phenvll-2-propenoic acid 3.02 g of the crude product described in Example P1 are introduced into 40 ml of a 1/1 mixture of dichloromethane (CH2CI2) and trifluoroacetic acid and stirred at 20°C for 2.5 hours. The mixture is then poured into 300 ml of ice-water, and the organic solvent is removed in vacuo. The aqueous phase is stirred, the precipitate is filtered off, washed with water and dried at 50°C in vacuo. 2.30 g of the desired title compound are obtained in the form of a beige solid.

'H-NMR (TMS, DMSO-D6) : 4.60 ppm (s, 2H); 6.53 ppm (d, 1 H) ; 7.39-7. 70 ppm (m, 5H); 12.47 ppm (broad signal, 1 H).

Example P3: Preparation of 3- (3-hydroxv-1-phenyl-1- (E)-propenyl)-benzeneacetonitrile 2.30 g of the acid from Example P2 are suspended in 20 ml of dry tetrahydrofuran (THF).

With stirring, 6.50 ml of triethyl borate are added and then, at 20°C, 1.35 ml of borane dimethyl sulfide complex are slowly added dropwise using a syringe. The temperature is maintained at below 22°C by cooling with a water bath. After subsequently stirring for three hours, thin-layer analysis of a sample (silica gel ; eluant : hexane/ethyl acetate 1/1) shows that the starting compound is no longer present. With stirring, 6.50 ml of methanol are slowly added dropwise. After subsequently being stirred for 15 minutes, the mixture is poured into ice-water and extracted with ether; the ether phase is dried over sodium sulfate, filtered, and completely concentrated by evaporation in vacuo. The crude product is purified by means of column chromatography over silica gel (eluant : hexane/ethyl acetate 1/1). The desired title compound is obtained in the form of a colourless resin in a yield of 0.63 g. 'H-NMR (TMS, Ceci3) : 1.50 ppm (broad signal, 1 H) ; 3.75 ppm (s, 2H); 4.36 ppm (d, 2H); 6.36-6. 45 ppm (m, 1H) ; 6.60 and 6.65 ppm (m, 1H) ; 7.17-7. 37 ppm (m, 4 H).

Example P4: Preparation of f3-f (E)-3- (4-fluoro-2-methoxy-phenoxv)-propenpheny]- acetonitrile (Comp. No. 1.072) 0.52 g of 4-fluoro-2-methoxy-phenol is dissolved in 20 ml of dry THF, and then 0.63 g of the alcohol prepared in Example P3 and 1.03 g of triphenylphosphine are added. Then, with stirring, 0.63 ml of azadicarboxylic acid ethyl ester is slowly added dropwise using a syringe and the mixture is then stirred overnight at 20°C. The next day, the mixture is partitioned between 1 M hydrochloric acid and diethyl ether. After extraction by shaking and separation of the phases, the organic phase is dried over sodium sulfate, filtered, and completely con- centrated in vacuo. The resulting crude product is purified by means of column chromato- graphy over silica gel (eluant : hexane/ethyl acetate 3/1). 0.67 g of the target compound is obtained in the form of a yellow oil.

Rf value 0.27 (silica gel 60F254; eluant : hexane/ethyl acetate 3/1).

Example P5: Preparation of 3-r3- (4-fluoro-2-methoxv-phenoxy)-1- (E)-propenyll-chloro- benzene (Comp. No. 1.253) 2.40 g of 4-fluoro-2-methoxy-phenol are introduced into dry THF and then 3.11 g of 3- (3- hydroxy-1-phenyl-1-(E)-propenyl-chlorobenzene and 4.76 g of triphenylphosphine are added. With stirring, at 20°C, 2.88 ml of azadicarboxylic acid diethyl ester are added dropwise and the mixture is then stirred overnight. The reaction mixture is then partitioned between diethyl ether and 1 M hydrochloric acid solution. After extraction by shaking and separation of the phases, the organic phase is dried over sodium sulfate, filtered, and completely concentrated in vacuo, yielding 1.54 g of a resin which is purified by column chromatography twice over silica gel (eluants : hexane/ethyl acetate 15/1 and toluene/hexane 3/1). 0.59 g of the desired target compound is obtained in a purity of 90%.

Rf value 0.55 (silica gel 60F254 ; eluant : toluene/hexane 3/1).

Exampfe P6: Preparation of [2-f (E)-3- (4-fluoro-2-methoxv-phenoxy)-propenyll-phenv acetonitrile (Comp. No. 1.187) 0.23 g of the allyl alcohol described in Example P9,0. 17 g of 4-fluoro-2-methoxy-phenol and 0.33 g of phosphine are introduced into 5 mi of absolute THF. With stirring, 0.20 ml of azadicarboxylic acid diethyl ester is slowly added and the mixture is stirred overnight at 20°C. The reaction mixture is then partitioned between diethyl ether and 1 M hydrochloric acid. After extraction by shaking and separation of the phases, the organic phase is washed with brine, dried over sodium sulfate, filtered, and completely concentrated by evaporation in vacuo. The crude product is purified by means of column chromatography over silica gel (eluant : at first hexane, then hexane/ethyl acetate 8/1), yielding 0.10 g of the desired title compound in the form of a brown-yellow resin.

'H-NMR (TMS, CDCI3) : 3.71 ppm (s, 2 H); 3.88 ppm (s, 3 H); 4.76 ppm (d x d, 2 H); 6.32- 6.37 ppm (m, 1 H); 6.55-6. 69 ppm (m, 2 H); 6.81-6. 91 ppm (m, 2 H); 7.29-7. 50 ppm (m, 4 H).

Example P7: Preparation of r4-f (E)-3- (4-fluoro-2-methoxy-phenoxy)-propenyll-phenvll- acetonitrile (Comp. No. 1.197) 0.23 g of 4- (3-hydroxy-1-phenyl-1- (E)-propenyl)-benzeneacetonitrile, 0.20 g of 4-fluoro-2- methoxy-phenol and 0.39 g of triphenylphosphine are introduced into 5.0 ml of absolute THF. With stirring, at 20°C, 0.24 ml of azadicarboxylic acid diethyl ester is slowly added dropwise and the mixture is stirred overnight at 20°C. The mixture is then partitioned between diethyl ether and 1 M hydrochloric acid. After extraction by shaking and separation of the phases, the organic phase is washed with brine, dried over sodium sulfate, filtered, and completely concentrated by evaporation in vacuo. The crude product is purified by means of column chromatography over silica gel (eluant (gradient) ): at first hexane, then hexane/ethyl acetate 8/1), yielding 0.22 g of the desired target compound in the form of a pale yellow solid.

'H-NMR (TMS, CDCI3) : 3.74 ppm (s, 2 H); 3.87 ppm (s, 3 H); 4.72 ppm (d x d, 2 H); 6.40- 6.72 ppm (m, 4 H) ; 6.84-6. 89 ppm (m, 1 H) ; 7.26-7. 42 ppm (m, 4 H). Example P8: Preparation of r2-f (E)-3- (tetrahvdro-2H-pvran-2-yioxy)-propenyll-pheny acetonitrile 5.53 g of tetrahydro-2- (2-propynyloxy)-2H-pyran are introduced into a round-bottomed flask under an argon atmosphere. Then 8.67 mi of 4, 4,5, 5-tetramethyl-1, 3, 2-dioxaborolane are added and the mixture is stirred at an oil bath temperature of 100°C for 4 hours. The oil bath temperature is then adjusted to 130°C and stirring is continued for 24 hours, followed by cooling to 20°C. The resulting intermediate can be used directly for the next step.

4.0 g of the intermediate obtained above are dissolved in benzene and then, with stirring, 3.62 g of 2-iodo-benzeneacetonitrile are added. With stirring, 13.9 ml of a 21% sodium ethanolat solution in ethanol are added dropwise, vigorous evolution of gas being observed initially. The reaction mixture is degassed with the aid of argon gas passed through the mixture and then 0.26 g of tetrakis (triphenylphosphine) palladium (Pd (PPh3) 4) is added.

Stirring is then continued for 31/2 hours with heating to reflux temperature. After being cooled to 20°C the mixture is partitioned between diethyl ether and cold 2M aqueous sodium hydroxide solution. After extraction by shaking and separation of the phases, the organic phase is washed with brine, dried over sodium sulfate, filtered, and completely concentrated by evaporation in vacuo. The resulting crude product is purified by means of column chromatography over silica gel (eluant : hexane/ethyl acetate 4/1), yielding 0.61 g of the desired title compound in the form of a yellow-brown oil.

Rf value 0.31 (silica gel 60F254 ; eluant : hexane/ethyl acetate 3/1).

Example P9: Preparation of 2- (3-hydroxv-1-phenvl-1- (E)-propenyl)-benzeneacetonitrile 0.61 g of the title compound according to Example P8 is introduced, with stirring, into 20 ml of a 1/1 mixture of THF and a 1 M hydrochloric acid solution and the mixture is then stirred at 20°C for 3 hours. The mixture is partitioned between diethyl ether and water. After extraction by shaking and separation of the phases, the organic phase is washed with brine, dried over sodium sulfate, filtered, and completely concentrated by evaporation in vacuo.

0.46 g of the desired title compound is obtained in the form of a brown-yellow oil which can be used directly without further purification.

Rf value 0.27 (silica gel 60F254 ; eluant : hexane/ethyl acetate 1/1).

In a manner analogous to that described in Examples P1 to P9 or in accordance with the methods as described in Reaction Schemes 1 to 5 and in the references indicated, it is also possible to obtain the preferred compounds listed in the following Tables. The temperatures given in the column headed"Phys. data"indicate the melting point (m. p. ) of the compounds in question.

Table 1: Compounds of formula la Comp. Ro, R, R2 R3 R4 Phys. data No. (m.p. °C) 1.001 CH3 H 3-CH2OH H H 1.002 CH3 4-CN 3-CH2-OH H H 1.003 CH3 4-CN, 5-F 3-CH2OH H H 1.004 CH3 4-F 3-CH2OH H H 1.005 CH3 4-Cl 3-CH2OH H H 1.006 CH3 4-Br 3-CH2OH H H 1.007 CH3 4-I 3-CH2OH H H 1.008 CH3 4-CF3 3-CH2OH H H 1.009 CH3 4-CF3, 5-F 3-CH2OH H H 1.010 CH3 4-CHO 3-CH2OH H H 1.011 CH3 4-CH=CH2 3-CH2OH H H 1.012 CH3 4-CH3 3-CH2OH H H 1.013 CH3 4-CH=NOH 3-CH2OH H H 1.014 CH3 4-CH=NOCH3 3-CH2OH H H 1.015 CH3 4-COOH 3-CH2OH H H 1.016 CH3 4-C (O) OC2Hs 3-CH2OH H H 1.017 CH3 4-C (O) NH2 3-CH2OH H H 1.018 CH3 4-C (S) NH2 3-CH2OH H H 1.019 CH3 4-OH 3-CH2OH H H 1.020 CH3 4-NH2 3-CH2OH H H 1.021 CH3 4-NO2 3-CH2OH H H 1.022 CH3 4-NO2, 5-F 3-CH2OH H H 1.023 CH3 4-F, 5-NO2 3-CH2OH H H 1.024 CH3 4-CI, 5-NO2 3-CH2OH H H 1.025 CH3 4-OCH3, 5-NO2 3-CH2OH H H Comp. R01 R1 R2 R3 R4 Phys. data No. (m.p. °C) 1.026 CH3 4-OH, 5-NO2 3-CH2OH H H 1.027 H H 3-CH2OH H H 1.028 H 4-NO2 3-CH2OH H H 1.029 H 4-CN 3-CH2OH H H 1.030 H 4-F 3-CH2OH H H 1.031 H 4-CF3 3-CH2OH H H 1.032 H 4-CHO 3-CH2OH H H 1.033 H 4-Br 3-CH2OH H H 1.034 CH3 H 3-CHF2 H H 1.035 CH3 4-CN 3-CHF2 H H 1.036 CH3 4-CN, 5-F 3-CHF2 H H 1.037 CH3 4-3-CHF2 H H 1.038 CH3 4-Cl 3-CHF2 H H 1.039 CH3 4-CI 5-F 3-CHF2 H H 1.040 CH3 4-Br 3-CHF2 H H 1.041 CH3 4-I 3-CHF2 H H 1.042 CH3 4-CF3 3-CHF2 H H 1.043 CH3 4-CHO 3-CHF2 H H 1.044 CH3 4-CH=CH2 3-CHF2 H H 1.045 CH3 4-CH3 3-CHF2 H H 1.046 CH3 4-CH=NOH 3-CHF2 H H 1.047 CH3 4-CH=NOCH3 3-CHF2 H H 1.048 CH3 4-COOH 3-CHF2 H H 1.049 CH3 4-C (O) OC2H5 3-CHF2 H H 1.050 CH3 4-C (O) NH2 3-CHF2 H H 1.051 CH3 4-C (S) NH2 3-CHF2 H H 1.052 CH3 4-OH 3-CHF2 H H 1.053 CH3 4-NH2 3-CHF2 H H 1.054 CH3 4-NO2 3-CHF2 H H 1.055 CH3 4-F, 5-NO2 3-CHF2 H H 1.056 CH3 4-Cl, 5-NO2 3-CHF2 H H 1.057 CH3 H 3-CHO H H 1.058 CH3 4-CN 3-CHO H H Comp. Roi R, R2 R3 R4 Phys. data No. (m. p. °C) 1.059 CH3 4-F 3-CHO H H 1.060 CH3 4-Br 3-CHO H H 1.061 CH3 4-CF3 3-CHO H H 1.062 CH3 4-CF3, 5-F 3-CHO H H 1.063 CH3 4-CH=NOCH3 3-CHO H H 1.064 CH3 4-NO2 3-CHO H H 1.065 CH3 4-NO2, 5-F 3-CHO H H 1.066 CH3 4-COOC (CH3) 3 3-CHO H H 1.067 CH3 4-F, 5-NO2 3-CHO H H 1.068 CH3 4-CI 5-N02 3-CHO H H 1.069 CH3 H 3-CH2CN H H 1.070 CH3 4-CN 3-CH2CN H H 1.071 CH3 4-CN, 5-F 3-CH2CN H H 1.072 CH3 4-3-CH2CN H H oil 1.073 CH3 4-F, 5-F 3-CH2CN H H 1.074 CH3 4-Cl 3-CH2CN H H 1.075 CH3 4-Cl, 5-F 3-CH2CN H H 1.076 CH3 4-Br 3-CH2CN H H 1.077 CH3 4-I 3-CH2CN H H 1.078 CH3 4-CF3 3-CH2CN H H amorphous 1.079 CH3 4-CF3, 5-F 3-CH2CN H H 1.080 CH3 4-CHO 3-CH2CN H H 1.081 CH3 4-CH2OH 3-CH2CN H H 1.082 CH3 4-CH=CH2 3-CH2CN H H 1.083 CH3 4-CH3 3-CH2CN H H 1.084 CH3 4-CH=NOH 3-CH2CN H H 1.085 CH3 4-CH=NOCH3 3-CH2CN H H 1.086 CH3 4-COOH 3-CH2CN H H 1.087 CH3 4-C (O) OC2H5 3-CH2CN H H 1.088 CH3 4-C (O) NH2 3-CH2CN H H 1.089 CH3 4-C (S) NH2 3-CH2CN H H 1.090 CH3 4-OH 3-CH2CN H H 1.091 CH3 4-NH2 3-CH2CN H H Comp. R01 R1 R2 R3 R4 Phys. data No. (m. p. °C) 1.092 CH3 4-NO2 3-CH2CN H H 1.093 CH3 4-NO2, 5-F 3-CH2CN H H 1.094 CH3 4-F, 5-NO2 3-CH2CN H H 1.095 CH3 4-CI, 5-NO2 3-CH2CN H H 1.096 CH3 4-OCH3, 5-NO2 3-CH2CN H H 1.097 CH3 4-OH, 5-NO2 3-CH2CN H H 1.098 H H 3-CH2CN H H 1.099 H 4-NO2 3-CH2CN H H 1.100 H 4-CN 3-CH2CN H H 1.101 H 4-F 3-CH2CN H H 1.102 H 4-CF3 3-CH2CN H H 1.103 H 4-CHO 3-CH2CN H H 1.104 H 4-CH=NOCH3 3-CH2CN H H 1.105 H 4-Br 3-CH2CN H H 1.106 CH3 H 3-CH2C (O) NH2 H H 1.107 CH3 4-F 3-CH2C (O) NH2 H H 1.108 CH3 4-CI 3-CH2C (O) NH2 H H 1.109 CH3 4-Br 3-CH2C(O)NH2 H H 1.110 CH3 4-NO2 3-CH2C (O) NH2 H H 1.111 CH3 4-NO2, 5-F 3-CH2C(O)NH2 H H 1.112 CH3 4-CF3 3-CH2C (O) NH2 H H 1. 113 CH3 4-CN 3-CH2C (O) NH2 H H 1. 114 CH3 4-COOCH3 3-CH2C (O) NH2 H H 1. 115 CH3 4-CHO 3-CH2C (O) NH2 H H 1. 116 CH3 4-CH=NOCH3 3-CH2C(O)NH2 H H 1. 117 CH3 4-NH2 3-CH2C(O)NH2 H H 1.118 CH3 4-OH 3-CH2C (O) NH2 H H 1. 119 CH3 H 3-CH2COOH H H 1. 120 CH3 4-F 3-CH2COOH H H 1. 121 CH3 4-F, 5-F 3-CH2COOH H H 1. 122 CH3 4-Cl 3-CH2COOH H H 1.123 CH3 4-Br 3-CH2COOH H H 1.124 CH3 4-NO2 3-CH2COOH H H Comp. Roi R, R2 R3 R4 Phys. data No. (m.p. °C) 1.125 CH3 4-CF3 3-CH2COOH H H 1.126 CH3 4-CN 3-CH2COOH H H 1.127 CH3 4-CN, 5-F 3-CH2COOH H H 1.128 CH3 4-COOCH3 3-CH2COOH H H 1.129 CH3 4-CHO 3-CH2COOH H H 1.130 CH3 4-CH=NOCH3 3-CH2COOH H H 1.131 CH3 4-NH2 3-CH2COOH H H 1.132 CH3 4-OH 3-CH2COOH H H 1.133 CH3 H 3-CH2C (S) NH2 H H 1.134 CH3 4-F 3-CH2C (S) NH2 H H 1.135 CH3 4-F, 5-F 3-CH2C (S) NH2 H H 1.136 CH3 4-CI 3-CH2C (S) NH2 H H 1.137 CH3 4-Br 3-CH2C (S) NH2 H H 1.138 CH3 4-NO2 3-CH2C(S)NH2 H H 1.139 CH3 4-NO2 5-F 3-CH2C (S) NH2 H H 1.140 CH3 4-CF3 3-CH2C (S) NH2 H H 1.141 CH3 4-COOCH3 3-CH2C (S) NH2 H H 1.142 CH3 4-CN 3-CH2C (S) NH2 H H 1. 143 CH3 4-CN, 5-F 3-CH2C(S)NH2 H H 1.144 CH3 4-CHO 3-CH2C (S) NH2 H H 1.145 CH3 4-CH=NOCH3 3-CH2C (S) NH2 H H 1.146 CH3 4-CH=NOCH3, 5-F 3-CH2C (S) NH2 H H 1.147 CH3 4-NH2 3-CH2C(S)NH2 H H 1.148 CH3 4-OH 3-CH2C (S) NH2 H H 1.149 CH3 H 3-CH (CH3) CN H H 1.150 CH3 4-CN 3-CH (CH3) CN H H 1.151 CH3 4-CN, 5-F 3-CH (CH3) CN H H 1.152 CH3 4-F 3-CH (CH3) CN H H 1.153 CH3 4-F, 5-F 3-CH (CH3) CN H H 1.154 CH3 4-CI 3-CH (CH3) CN H H 1.155 CH3 4-Br 3-CH (CH3) CN H H 1. 156 CH3 4-1 3-CH (CH3) CN H H 1. 157 CH3 4-CF3 3-CH (CH3) CN H H Comp. Ro, R, R2 R3 R4 Phys. data No. (m. p. °C) 1.158 CH3 4-CHO 3-CH (CH3) CN H H 1.159 CH3 4-CH=CH2 3-CH (CH3) CN H H 1.160 CH3 4-CH3 3-CH (CH3) CN H H 1.161 CH3 4-CH=NOH 3-CH (CH3) CN H H 1.162 CH3 4-CH=NOCH3 3-CH (CH3) CN H H 1.163 CH3 4-CH=NOCH3,5-F 3-CH (CH3) CN H H 1.164 CH3 4-COOH 3-CH (CH3) CN H H 1.165 CH3 4-C (O) OC2H5 3-CH (CH3) CN H H 1.166 CH3 4-C (O) NH2 3-CH (CH3) CN H H 1.167 CH3 4-C (S) NH2 3-CH (CH3) CN H H 1.168 CH3 4-OH 3-CH (CH3) CN H H 1.169 CH3 4-NH2 3-CH (CH3) CN H H 1.170 CH3 4-NO2 3-CH (CH3) CN H H 1.171 CH3 4-F, 5-NO2 3-CH (CH3) CN H H 1.172 CH3 4-CI, 5-NO2 3-CH (CH3) CN H H 1.173 CH3 4-OCH3, 5-NO2 3-CH (CH3) CN H H 1.174 CH3 4-OH, 5-NO2 3-CH (CH3) CN H H 1.175 CH3 4-CH2CN 3-CH2OH H H 1.176 CH3 4-CH2CN 3-CH2CN H H 1.177 CH3 4-CH2CN 3-CH (CH3) CN H H 1.178 CH3 4-CH2CN 3-CH2C (O) NH2 H H 1.179 CH3 4-CH2CN 3-CH2C (S) NH2 H H 1.180 CH3 4-CH2CN 3-C(O)OC2H5 H H 1.181 CH3 4-CH2CN 3-Cl H H resin 1.182 CH3 4-CH2CN 3-Br H H 1.183 CH3 4-CH2CN 3-CI, 4-Cl H H RESIN 1.184 CH3 H 2-CH2CN H H 1.185 CH3 4-CN 2-CH2CN H H 1.186 CH3 4-CN, 5-F 2-CH2CN H H 1.187 CH3 4-F 2-CH2CN H H resin 1.188 CH3 4-F, 5-F 2-CH2CN H H 1.189 CH3 4-I 2-CH2CN H H 1.190 CH3 4-CF3 2-CH2CN H H solid Comp. R01 R1 R2 R3 R4 Phys. data No. (m.p. °C) 1.191 CH3 4-CH=NOCH3 2-CH2CN H H 1.192 CH3 4-CH=NOCH3,5-F 2-CH2CN H H 1.193 CH3 4-NO2 2-CH2CN H H 1.194 CH3 H 4-CH2CN H H 1.195 CH3 4-CN 4-CH2CN H H 1.196 CH3 4-CN, 5-F 4-CH2CN H H 1.197 CH3 4-F 4-CH2CN H H solid 1.198 CH3 4-F, 5-F 4-CH2CN H H 1.199 CH3 4-1 4-CH2CN H H 1.200 CH3 4-CF3 4-CH2CN H H resin 1.201 CH3 4-CH=NOCH3 4-CH2CN H H 1.202 CH3 4-CH=NOCH3, 5-F 4-CH2CN H H 1.203 CH3 4-NO2 4-CH2CN H H 1.204 CH3 H 3-CH2CN CH3 H 1.205 CH3 4-F 3-CH2CN CH3 H 1.206 CH3 4-Br 3-CH2CN CH3 H 1.207 CH3 4-CF3 3-CH2CN CH3 H 1.208 CH3 4-CN 3-CH2CN CH3 H 1.209 CH3 4-CN, 5-F 3-CH2CN CH3 H 1.210 CH3 4-CH=NOCH3 3-CH2CN CH3 H 1.211 CH3 4-F 3-CH (CH3) CN CH3 H 1.212 CH3 4-Br 3-CH (CH3) CN CH3 H 1.213 CH3 4-CF3 3-CH (CH3) CN CH3 H 1. 214 CH3 4-CN 3-CH (CH3) CN CH3 H 1.215 CH3 4-F, 5-F 3-CH (CH3) CN CH3 H 1.216 CH3 4-CH=NOCH3 3-CH (CH3) CN CH3 H 1.217 CH3 4-F 3-CHF2 CH3 H 1.218 CH3 4-Br 3-CHF2 CH3 H 1.219 CH3 4-CF3 3-CHF2 CH3 H 1.220 CH3 4-CN 3-CHF2 CH3 H 1.221 CH3 4-F, 5-F 3-CHF2 CH3 H 1.222 CH3 4-CH=NOCH3 3-CHF2 CH3 H 1.223 CH3 H 3-C(O)OC2H5 H H Comp. Roi R, R2 R3 R4 Phys. data No. (m. p. °C) 1.224 CH3 4-F 3-C (O) OC2H5 H H 1.225 CH3 4-Br 3-C (O) OC2H5 H H 1.226 CH3 4-NO2 3-C (O) OC2H5 H H 1.227 CH3 4-NH2 3-C (O) OC2H5 H H 1.228 CH3 4-CF3 3-C (O) OC2H5 H H 1.229 CH3 4-CN 3-C (O) OC2H5 H H 1.230 CH3 4-CHO 3-C (O) OC2H5 H H 1.231 CH3 4-CH=NOCH3 3-C (O) OC2H5 H H 1.232 CH3 H 3-COOH H H 1.233 CH3 4-F 3-COOH H H 1.234 CH3 4-Br 3-COOH H H 1.235 CH3 4-NO2 3-COOH H H 1.236 CH3 4-NH2 3-COOH H H 1.237 CH3 4-CF3 3-COOH H H 1.238 CH3 4-CN 3-COOH H H 1.239 CH3 4-CHO 3-COOH H H 1.240 CH3 4-CH=NOCH3 3-COOH H H 1.241 CH3 H 3-Br H H 1.242 CH3 4-F 3-Br H H 1.243 CH3 4-Br 3-Br H H 1.244 CH3 4-NO2 3-Br H H 1.245 CH3 4-NH2 3-Br H H 1.246 CH3 4-CF3 3-Br H H 1.247 CH3 4-CN 3-Br H H 1.248 CH3 4-CHO 3-Br H H 1.249 CH3 4-CH=NOCH3 3-Br H H 1.250 CH3 4-COOH 3-Br H H 1.251 CH3 4-C (O) OCH3 3-Br H H 1.252 CH3 H 3-CI H H 1.253 CH3 4-F 3-CI H H resin 1.254 CH3 4-CF3 3-CI H H 1.255 CH3 4-CN 3-CI H H 1.256 CH3 4-NO2 3-Cl H H Comp. Ro, R, R2 R3 R4 Phys. data No. (m. p. °C) 1.257 CH3 4-NH2 3-Cl H H 1.258 CH3 4-C (O) OCH3 3-CI H H 1.259 CH3 H 4-Cl H H 1.260 CH3 4-F 4-Cl H H 1.261 CH3 4-CF3 4-CI H H 1.262 CH3 4-CN 4-CI H H resin 1.263 CH3 4-NO2 4-Cl H H 1.264 CH3 4-NH2 4-Cl H H 1.265 CH3 4-C (O) OCH3 4-CI H H 1.266 CH3 H 3-CH2CI H H 1.267 CH3 4-F 3-CH2Cl H H 1.268 CH3 4-Br 3-CH2Cl H H 1.269 CH3 4-NO2 3-CH2CI H H 1.270 CH3 4-NH2 3-CH2Cl H H 1.271 CH3 4-CF3 3-CH2Cl H H 1.272 CH3 4-CN 3-CH2CI H H 1.273 CH3 4-CHO 3-CH2Cl H H 1.274 CH3 4-CH=NOCH3 3-CH2CI H H 1.275 CH3 4-COOH 3-CH2Cl H H 1.276 CH3 4-C (O) OCH3 3-CH2Cl H H 1.277 CH3 H 3-CH2Br H H 1.278 CH3 4-F 3-CH2Br H H 1.279 CH3 4-Br 3-CH2Br H H 1.280 CH3 4-NO2 3-CH2Br H H 1.281 CH3 4-NH2 3-CH2Br H H 1.282 CH3 4-CF3 3-CH2Br H H 1.283 CH3 4-CN 3-CH2Br H H 1.284 CH3 4-CHO 3-CH2Br H H 1.285 CH3 4-CH=NOCH3 3-CH2Br H H 1.286 CH3 4-COOH 3-CH2Br H H 1.287 CH3 4-C (O) OCH3 3-CH2Br H H 1.288 CH3 H 3-CHO CH3 H 1.289 CH3 4-F 3-CHO CH3 H Comp. Roi R, R2 R3 R4 Phys. data No. (m. p. °C) 1.290 CH3 4-Cl 3-CHO CH3 H 1.291 CH3 4-Br 3-CHO CH3 H 1.292 CH3 4-CF3 3-CHO CH3 H 1.293 CH3 4-CN 3-CHO CH3 H 1.294 CH3 4-NO2 3-CHO CH3 H 1.295 CH3 4-CH=NOCH3 3-CHO CH3 H 1.296 CH3 H 3-NO2 H H 1.297 CH3 4-F 3-NO2 H H 1.298 CH3 4-Cl 3-NO2 H H 1.299 CH3 4-Br 3-NO2 H H 1.300 CH3 4-CF3 3-NO2 H H 1.301 CH3 4-CN 3-NO2 H H 1.302 CH3 4-CHO 3-NO2 H H 1.303 CH3 4-CH=NOCH3 3-NO2 H H 1.304 CH3 H 3-NH2 H H 1.305 CH3 4-F 3-NH2 H H 1.306 CH3 4-Cl 3-NH2 H H 1.307 CH3 4-Br 3-NH2 H H 1.308 CH3 4-CF3 3-NH2 H H 1.309 CH3 4-CN 3-NH2 H H 1.310 CH3 4-CHO 3-NH2 H H 1.311 CH3 4-CH=NOCH3 3-NH2 H H 1.312 CH3 H 3-NH-C (O) CH3 H H 1.313 CH3 4-F 3-NH-C (O) CH3 H H 1.314 CH3 4-Cl 3-NH-C(O) CH3 H H 1.315 CH3 4-Br 3-NH-C (O) CH3 H H 1.316 CH3 4-CF3 3-NH-C (O) CH3 H H 1.317 CH3 4-CN 3-NH-C (O) CH3 H H 1.318 CH3 4-CHO 3-NH-C (O) CH3 H H 1.319 CH3 4-CH=NOCH3 3-NH-C (O) CH3 H H 1.320 CH3 H 3-N (CH2CCH)- H H C(O)CH3 Comp. R01 R1 R2 R3 R4 Phys. data No. (m.p. °C) 1.321 CH3 4-F 3-N (CH2CCH)- H H C (O) CH3 1.322 CH3 4-Cl 3-N (CH2CCH)- H H C (O) CH3 1.323 CH3 4-Br 3-N (CH2CCH)- H H C (O) CH3 1. 324 CH3 4-CF3 3-N (CH2CCH)- H H C (O) CH3 1.325 CH3 4-CN 3-N (CH2CCH)- H H C (O) CH3 1.326 CH3 4-CHO 3-N (CH2CCH)- H H C (O) CH3 1.327 CH3 4-CH=NOCH3 3-N (CH2CCH)- H H C (O) CH3 1.328 CH3 H 4-Br H H 1.329 CH3 4-F 4-Br H H 1.330 CH3 4-CF3 4-Br H H 1.331 CH3 4-CN 4-Br H H 1.332 CH3 4-NO2 4-Br H H 1.333 CH3 4-NH2 4-Br H H 1.334 CH3 4-C (O) OCH3 4-Br H H 1.335 CH3 H 2-Br H H 1.336 CH3 4-F 2-Br H H 1.337 CH3 4-CF3 2-Br H H 1.338 CH3 4-CN 2-Br H H 1.339 CH3 4-NO2 2-Br H H 1.340 CH3 4-NH2 2-Br H H 1.341 CH3 4-C (O) OCH3 2-Br H H 1.342 CH3 H 4-CHO H H 1.343 CH3 4-CN 4-CHO H H 1.344 CH3 4-F 4-CHO H H 1.345 CH3 4-Br 4-CHO H H 1.346 CH3 4-CF3 4-CHO H H Comp. Roi R, R2 R3 R4 Phys. data No. (m. p. °C) 1.347 CH3 4-CF3, 5-F 4-CHO H H 1.348 CH3 4-CH=NOCH3 4-CHO H H 1.349 CH3 4-NO2 4-CHO H H 1.350 CH3 4-NO2, 5-F 4-CHO H H 1.351 CH3 4-C (O) OC (CH3) 3 4-CHO H H 1.352 CH3 4-F, 5-NO2 4-CHO H H 1.353 CH3 4-CI, 5-NO2 4-CHO H H 1.354 CH3 H 2-CHO H H 1.355 CH3 4-CN 2-CHO H H 1.356 CH3 4-F 2-CHO H H 1.357 CH3 4-Br 2-CHO H H 1.358 CH3 4-CF3 2-CHO H H 1.359 CH3 4-CF3, 5-F 2-CHO H H 1.360 CH3 4-CH=NOCH3 2-CHO H H 1.361 CH3 4-NO2 2-CHO H H 1.362 CH3 4-NO2, 5-F 2-CHO H H 1.363 CH3 4-C (O) OC (CH3) 3 2-CHO H H 1.364 CH3 4-F, 5-NO2 2-CHO H H 1.365 CH3 4-CI, 5-NO2 2-CHO H H 1.366 CH3 H 3-CH2CN, 4-F H H 1.367 CH3 4-CN 3-CH2CN, 4-F H H 1.368 CH3 4-F 3-CH2CN, 4-F H H 1.369 CH3 4-Cl 3-CH2CN, 4-F H H 1.370 CH3 4-Br 3-CH2CN, 4-F H H 1.371 CH3 4-I 3-CH2CN, 4-F H H 1.372 CH3 4-CF3 3-CH2CN, 4-F H H 1.373 CH3 4-CHO 3-CH2CN, 4-F H H 1.374 CH3 4-CH3 3-CH2CN, 4-F H H 1.375 CH3 4-CH=NOH 3-CH2CN, 4-F H H 1.376 CH3 4-CH=NOCH3 3-CH2CN, 4-F H H 1.377 CH3 4-COOH 3-CH2CN, 4-F H H 1. 378 CH3 4-C (O) OC2H5 3-CH2CN, 4-F H H 1. 379 CH3 4-C (O) NH2 3-CH2CN, 4-F H H Comp. Roi R, R2 R3 R4 Phys. data No. (m. p. °C) 1.380 CH3 4-C (S) NH2 3-CH2CN, 4-F H H 1.381 CH3 4-NH2 3-CH2CN, 4-F H H 1.382 CH3 4-NO2 3-CH2CN, 4-F H H 1.383 CH3 H 3-CH2CN, 4-F, H H 6-F 1. 384 CH3 4-CN 3-CH2CN, 4-F, H H 6-F 1.385 CH3 4-F 3-CH2CN, 4-F, H H 6-F 1.386 CH3 4-Cl 3-CH2CN, 4-F, H H 6-F 1.387 CH3 4-Br 3-CH2CN, 4-F, H H 6-F 1.388 CH3 4-l 3-CH2CN, 4-F, H H 6-F 1.389 CH3 4-CF3 3-CH2CN, 4-F, H H 6-F 1. 390 CH3 4-CHO 3-CH2CN, 4-F, H H 6-F 1.391 CH3 4-CH3 3-CH2CN, 4-F, H H 6-F 1. 392 CH3 4-CH=NOH 3-CH2CN, 4-F, H H 6-F 1. 393 CH3 4-CH=NOCH3 3-CH2CN, 4-F, H H 6-F 1.394 CH3 4-COOH 3-CH2CN, 4-F, H H 6-F 1.395 CH3 4-C (O) OC2H5 3-CH2CN, 4-F, H H 6-F 1. 396 CH3 4-C (O) NH2 3-CH2CN, 4-F, H H 6-F 1. 397 CH3 4-C (S) NH2 3-CH2CN, 4-F, H H 6-F Comp. R01 R1 R2 R3 R4 Phys. data No. (m.p. °C) 1.398 CH3 4-NH2 3-CH2CN, 4-F, H H 6-F 1.399 CH3 4-NO2 3-CH2CN, 4-F, H H 6-F 1.400 CH3 H 3-CH2CN, 4-CI, H H 6-F 1.401 CH3 4-CF3 3-CH2CN, 4-Cl, H H 6-F 1.402 CH3 4-CHO 3-CH2CN, 4-CI, H H 6-F 1.403 CH3 4-CH3 3-CH2CN, 4-CI, H H 6-F 1.404 CH3 4-CH=NOH 3-CH2CN, 4-CI, H H 6-F 1.405 CH3 4-CH=NOCH3 3-CH2CN, 4-Cl, H H 6-F 1.406 CH3 4-COOH 3-CH2CN, 4-CI, H H 6-F 1.407 CH3 4-C (O) OC2Hs 3-CH2CN, 4-Cl, H H 6-F 1.408 CH3 4-C (O) NH2 3-CH2CN, 4-Cl, H H 6-F 1.409 CH3 4-C (S) NH2 3-CH2CN, 4-Cl, H H 6-F 1.410 CH3 4-NH2 3-CH2CN, 4-Cl, H H 6-F 1.411 CH3 4-NO2 3-CH2CN, 4-Cl, H H 6-F 1.412 CH3 H 3-CH2CN, 6-F H H 1.413 CH3 4-CN 3-CH2CN, 6-F H H 1.414 CH3 4-F 3-CH2CN, 6-F H H 1.415 CH3 4-Cl 3-CH2CN, 6-F H H 1.416 CH3 4-Br 3-CH2CN, 6-F H H Comp. Roi R, R2 R3 R4 Phys. data No. (m. p. °C) 1.417 CH3 4-1 3-CH2CN, 6-F H H 1.418 CH3 4-CF3 3-CH2CN, 6-F H H 1.419 CH3 4-CHO 3-CH2CN, 6-F H H 1.420 CH3 4-CH3 3-CH2CN, 6-F H H 1.421 CH3 4-CH=NOH 3-CH2CN, 6-F H H 1.422 CH3 4-CH=NOCH3 3-CH2CN, 6-F H H 1.423 CH3 4-COOH 3-CH2CN, 6-F H H 1.424 CH3 4-C (O) OC2H5 3-CH2CN, 6-F H H 1.425 CH3 4-C (O) NH2 3-CH2CN, 6-F H H 1.426 CH3 4-C (S) NH2 3-CH2CN, 6-F H H 1.427 CH3 4-NH2 3-CH2CN, 6-F H H 1.428 CH3 4-NO2 3-CH2CN, 6-F H H 1.429 CH3 H 3-CH2, 4-F H H 1.430 CH3 4-CN 3-CHF2, 4-F H H 1.431 CH3 4-F 3-CHF2, 4-F H H 1.432 CH3 4-Cl 3-CHF2, 4-F H H 1.433 CH3 4-Br 3-CHF2, 4-F H H 1.434 CH3 4-l 3-CHF2, 4-F H H 1.435 CH3 4-CF3 3-CHF2, 4-F H H 1.436 CH3 4-CHO 3-CHF2, 4-F H H 1.437 CH3 4-CH3 3-CHF2, 4-F H H 1.438 CH3 4-CH=NOH 3-CHF2, 4-F H H 1.439 CH3 4-CH=NOCH3 3-CHF2, 4-F H H 1.440 CH3 4-COOH 3-CHF2, 4-F H H 1.441 CH3 4-C (O) OC2H5 3-CHF2, 4-F H H 1.442 CH3 4-C (O) NH2 3-CHF2, 4-F H H 1.443 CH3 4-C (S) NH2 3-CHF2, 4-F H H 1.444 CH3 4-NH2 3-CHF2, 4-F H H 1.445 CH3 4-NO2 3-CHF2, 4-F H H 1.446 CH3 H 3-CHF2, 4-F, 6-F H H 1.447 CH3 4-CN 3-CHF2, 4-F, 6-F H H 1.448 CH3 4-F 3-CHF2, 4-F, 6-F H H 1.449 CH3 4-Cl 3-CHF2, 4-F, 6-F H H Comp. Ro, R, R2 R3 R4 Phys. data No. (m. p. °C) 1.450 CH3 4-Br 3-CHF2, 4-F, 6-F H H 1.451 CH3 4-I 3-CHF2, 4-F, 6-F H H 1.452 CH3 4-CF3 3-CHF2, 4-F, 6-F H H 1.453 CH3 4-CHO 3-CHF2, 4-F, 6-F H H 1.454 CH3 4-CH3 3-CHF2, 4-F, 6-F H H 1.455 CH3 4-CH=NOH 3-CHF2, 4-F, 6-F H H 1.456 CH3 4-CH=NOCH3 3-CHF2, 4-F, 6-F H H 1.457 CH3 4-COOH 3-CHF2, 4-F, 6-F H H 1.458 CH3 4-C (O) OC2H5 3-CHF2, 4-F, 6-F H H 1.459 CH3 4-C (O) NH2 3-CHF2, 4-F, 6-F H H 1.460 CH3 4-C (S) NH2 3-CHF2, 4-F, 6-F H H 1.461 CH3 4-NH2 3-CHF2, 4-F, 6-F H H 1.462 CH3 4-NO2 3-CHF2, 4-F, 6-F H H 1.463 CH3 H 3-CHF2, 4-CI, H H 6-F 1.464 CH3 4-CN 3-CHF2, 4-CI, H H 6-F 1.465 CH3 4-F 3-CHF2, 4-CI, H H 6-F 1.466 CH3 4-Cl 3-CHF2, 4-CI, H H 6-F 1.467 CH3 4-Br 3-CHF2, 4-CI, H H 6-F 1.468 CH3 4-I 3-CHF2, 4-CI, H H 6-F 1.469 CH3 4-CF3 3-CHF2, 4-CI, H H 6-F 1.470 CH3 4-CHO 3-CHF2, 4-Cl, H H 6-F 1.471 CH3 4-CH3 3-CHF2, 4-C, H H 6-F 1.472 CH3 4-CH=NOH 3-CHF2, 4-Cl, H H 6-F Comp. Ro, R, R2 R3 R4 Phys. data No. (m. p. °C) 1.473 CH3 4-CH=NOCH3 3-CHF2, 4-Cl, H H 6-F 1.474 CH3 4-COOH 3-CHF2, 4-Cl, H H 6-F 1.475 CH3 4-C (O) OC2H5 3-CHF2, 4-Cl, H H 6-F 1.476 CH3 4-C (O) NH2 3-CHF2, 4-CI, H H 6-F 1.477 CH3 4-C (S) NH2 3-CHF2, 4-CI, H H 6-F 1.478 CH3 4-NH2 3-CHF2, 4-CI, H H 6-F 1.479 CH3 4-NO2 3-CHF2, 4-CI, H H 6-F 1.480 CH3 H 3-CHF2, 6-F H H 1.481 CH3 4-CN 3-CHF2, 6-F H H 1.482 CH3 4-F 3-CHF2, 6-F H H 1.483 CH3 4-Cl 3-CHF2, 6-F H H 1.484 CH3 4-Br 3-CHF2, 6-F H H 1.485 CH3 4-1 3-CHF2, 6-F H H 1.486 CH3 4-CF3 3-CHF2, 6-F H H 1.487 CH3 4-CHO 3-CHF2, 6-F H H 1.488 CH3 4-CH3 3-CHF2, 6-F H H 1.489 CH3 4-CH=NOH 3-CHF2, 6-F H H 1.490 CH3 4-CH=NOCH3 3-CHF2, 6-F H H 1.491 CH3 4-COOH 3-CHF2, 6-F H H 1.492 CH3 4-C (O) OC2H5 3-CHF2, 6-F H H 1.493 CH3 4-C (O) NH2 3-CHF2. 6-F H H 1.494 CH3 4-C (S) NH2 3-CHF2, 6-F H H 1.495 CH3 4-NH2 3-CHF2, 6-F H H 1.496 CH3 4-NO2 3-CHF2, 6-F H H 1.497 CH3 H H H H 1. 498 CH3 4-CN H H H Comp. Roi R, R2 R3 R4 Phys. data No. (m. p. °C) 1. 499 CH3 4-F H H H 1.500 CH3 4-Cl H H H 1.501 CH3 4-Br H H H 1.502 CH3 4-I H H H 1.503 CH3 4-CF3 H H H 1.504 CH3 4-CHO H H H solid 1.505 CH3 4-CH3 H H H 1.506 CH3 4-CH=NOH H H H 1.507 CH3 4-CH=NOCH3 H H H 1.508 CH3 4-COOH H H H 1.509 CH3 4-C (O) OC2H5 H H H 1.510 CH3 4-C (O) NH2 H H H 1.511 CH3 4-C (S) NH2 H H H 1.512 CH3 4-NH2 H H H 1.513 CH3 4-NO2 H H H 1.514 CH3 H H CH3 H 1.515 CH3 4-F H CH3 H 1.516 CH3 4-CF3 H CH3 H 1.517 CH3 4-CN H CH3 H 1.518 CH3 4-CH=NOCH3 H CH3 H 1.519 CH3 4-CN 3-CH2CN, 4-F CH3 H 1.520 CH3 4-F 3-CH2CN, 4-F CH3 H 1.521 CH3 4-Cl 3-CH2CN, 4-F CH3 H 1.522 CH3 H 3-CH2CN, 4-F CH3 H 1.523 CH3 4-CF3 3-CH2CN, 4-F CH3 H 1.524 CH3 4-CH3 3-CH2CN, 4-F CH3 H 1.525 CH3 4-CH=NOCH3 3-CH2CN, 4-F CH3 H 1.526 CH3 4-CN 3-CH2CN, 4-F, CH3 H 6-F 1.527 CH3 4-F 3-CH2CN, 4-F, CH3 H 6-F 1.528 CH3 4-Cl 3-CH2CN, 4-F, CH3 H 6-F Comp. Ro, R, R2 R3 R4 Phys. data No. (m. p. °C) 1. 529 CH3 H 3-CH2CN, 4-F, CH3 H 6-F 1. 530 CH3 4-CF3 3-CH2CN, 4-F, CH3 H 6-F 1. 531 CH3 4-CH3 3-CH2CN, 4-F, CH3 H 6-F 1. 532 CH3 4-CH=NOCH3 3-CH2CN, 4-F, CH3 H 6-F 1.533 CH3 4-CN 3-CH2CN, 6-F CH3 H 1.534 CH3 4-F 3-CH2CN, 6-F CH3 H 1.535 CH3 4-Cl 3-CH2CN, 6-F CH3 H 1.536 CH3 H 3-CH2CN, 6-F CH3 H 1.537 CH3 4-CF3 3-CH2CN, 6-F CH3 H 1.538 CH3 4-CH3 3-CH2CN, 6-F CH3 H 1.539 CH3 4-CH=NOCH3 3-CH2CN, 6-F CH3 H 1.540 CH3 4-CN 3-CH2CN, 4-CI, CH3 H 6-F 1.541 CH3 4-F 3-CH2CN, 4-CI, CH3 H 6-F 1.542 CH3 4-Cl 3-CH2CN, 4-CI, CH3 H 6-F 1.543 CH3 H 3-CH2CN, 4-Cl, CH3 H 6-F 1.544 CH3 4-CF3 3-CH2CN, 4-CI, CH3 H 6-F 1.545 CH3 4-CH3 3-CH2CN, 4-Cl, CH3 H 6-F 1.546 CH3 4-CH=NOCH3 3-CH2CN, 4-CI, CH3 H 6-F 1.547 CH3 4-CN 3-CHF2, 4-F CH3 H 1.548 CH3 4-F 3-CHF2, 4-F CH3 H 1.549 CH3 4-CI 3-CHF2, 4-F CH3 H 1.550 CH3 H 3-CHF2, 4-F CH3 H Comp. Roi R, R2 R3 R4 Phys. data No. (m. p. °C) 1.551 CH3 4-CF3 3-CHF2, 4-F CH3 H 1.552 CH3 4-CH3 3-CHF2, 4-F CH3 H 1.553 CH3 4-CH=NOCH3 3-CHF2, 4-F CH3 H 1.554 CH3 4-CN 3-CHF2, 4-F, 6-F CH3 H 1.555 CH3 4-F 3-CHF2, 4-F, 6-F CH3 H 1.556 CH3 4-Cl 3-CHF2, 4-F, 6-F CH3 H 1.557 CH3 H 3-CHF2, 4-F, 6-F CH3 H 1.558 CH3 4-CF3 3-CHF2, 4-F, 6-F CH3 H 1.559 CH3 4-CH3 3-CHF2, 4-F, 6-F CH3 H 1.560 CH3 4-CH=NOCH3 3-CHF2, 4-F, 6-F CH3 H 1.561 CH3 4-CN 3-CHF2, 6-F CH3 H 1.562 CH3 4-F 3-CHF2, 6-F CH3 H 1.563 CH3 4-CI 3-CHF2, 6-F CH3 H 1.564 CH3 H 3-CHF2, 6-F CH3 H 1.565 CH3 4-CF3 3-CHF2, 6-F CH3 H 1.566 CH3 4-CH3 3-CHF2, 6-F CH3 H 1.567 CH3 4-CH=NOCH3 3-CHF2, 6-F CH3 H 1.568 CH3 4-CN 3-CHF2, 4-CI, CH3 H 6-F 1.569 CH3 4-F 3-CHF2, 4-CI, CH3 H 6-F 1.570 CH3 4-Cl 3-CHF2, 4-CI, CH3 H 6-F 1.571 CH3 H 3-CHF2, 4-CI, CH3 H 6-F 1.572 CH3 4-CF3 3-CHF2, 4-Cl, CH3 H 6-F 1.573 CH3 4-CH3 3-CHF2, 4-CI, CH3 H 6-F 1.574 CH3 4-CH=NOCH3 3-CHF2, 4-CI, CH3 H 6-F Biological Examples Example B1 : Herbicidal action prior to emergence of the plants (pre-emerqence action) Monocotyledonous and dicotyledonous test plants are sown in standard soil in pots.

Immediately after sowing, the test compounds, in the form of an aqueous suspension (prepared from a wettable powder (Example F3, b) according to WO 97/34485) or in the form of an emulsion (prepared from an emulsifiable concentrate (Example F1, c) according to WO 97/34485), are applied by spraying in an optimum concentration (500 litres of water/ha). The test plants are then grown in a greenhouse under optimum conditions.

After a test duration of 4 weeks, the test is evaluated in accordance with a scale of nine ratings (1 = total damage, 9 = no action). Ratings of from 1 to 4 (especially from 1 to 3) indicate good to very good herbicidal action.

Test plants : Panicum, Digitaria, Euphorbia, Amaranthus Table B1 : Concentration 1000 a active inqredient/ha Test plant : Panicum Digitaria Euphorbia Amaranthus Comp. No. 1.078 1 3 1 1 The same results are obtained when the compounds of formula I are formulated in accordance with the other Examples analogously to WO 97/34485.

Example B2: Post-emergence herbicidal action Monocotyledonous and dicotyledonous test plants are sown in standard soil in pots. When the test plants are at the 2-to 3-leaf stage, the test compounds, in the form of an aqueous suspension (prepared from a wettable powder (Example F3, b) according to WO 97/34485) or in the form of an emulsion (prepared from an emulsifiable concentrate (Example F1, c) according to WO 97/34485), are applied by spraying in an optimum concentration (500 litres of water/ha). The test plants are then grown on in a greenhouse under optimum conditions.

After a test duration of 2 to 3 weeks, the test is evaluated in accordance with a scale of nine ratings (1 = total damage, 9 = no action). Ratings of from 1 to 4 (especially from 1 to 3) indicate good to very good herbicidal action. Test plants : Panicum (Pani), Scirpus, Euphorbia (Euph), Abutilon (Abut), Amaranthus (Amar), Stellaria, Veronica Table B2: Concentration 500 g active inaredient/ha Test plant : Pani Scirpus Euph Abut Amar Stellaria Veronica Comp. No. 1. 072 2 2 1 2 2 2 2 1. 078 3 2 2 2 2 3 2 The same results are obtained when the compounds of formula I are formulated in accordance with the other Examples analogously to WO 97/34485.