Process for the preparation of herbicidal derivatives

Abstract

A process for the preparation of compounds of formula I wherein R 0 is, each independently of any other, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, cyano-C 1 -C 6 alkyl, C 2 -C 6 haloalkenyl, cyano-C 2 -C 6 alkenyl, C 2 -C 6 haloalkynyl, cyano-C 2 -C 6 alkynyl, hydroxy, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, nitro, amino, C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 alkylaminosulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkenyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkenyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkynyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkynyl, C 1 -C 6 alkoxycarbonyl, cyano, carboxyl, phenyl or an aromatic ring that contains 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the latter two aromatic rings may be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro; or R 0 , together with the adjacent substituents R 1 , R 2 and R 3 , forms a saturated or unsaturated C 3 -C 6 hydrocarbon bridge that may be interrupted by 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur and/or may be substituted by C 1 -C 4 alkyl; R 1 , R 2 and R 3 are each independently of the others hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkenyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkenyl, cyano-C 2 -C 6 alkenyl, nitro-C 2 -C 6 -alkenyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkynyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 -alkynyl, cyano-C 2 -C 6 alkynyl, nitro-C 2 -C 6 alkynyl, C 3 -C 6 halocycloalkyl, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkylthio-C 1 -C 6 alkyl, cyano, C 1 -C 4 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, hydroxy, C 1 -C 10 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 haloalkoxy, C 3 -C 6 -haloalkenyloxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, mercapto, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, nitro, amino, C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino or phenoxy in which the phenyl ring may be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 -alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro; R 2 also may be phenyl, naphthyl or a 5- or 6-membered aromatic ring that may contain 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by halogen, C 3 -C 8 cycloalkyl, hydroxy, mercapto, amino, cyano, nitro or by formyl; and/or the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, mono-C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylcarbonyl-(C 1 -C 6 alkyl)amino, C 2 -C 6 alkenyl, C 3 -C 6 alkenyloxy, hydroxy-C 3 -C 6 alkenyl, C 1 -C 6 alkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 alkoxy-C 3 -C 6 alkenyloxy, C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, mono- or di-(C 2 -C 6 alkenyl)amino, C 1 -C 6 alkyl(C 3 -C 6 alkenyl)-amino, C 2 -C 6 alkenylcarbonylamino, C 2 -C 6 alkenylcarbonyl(C 1 -C 6 alkyl)amino, C 2 -C 6 alkynyl, C 3 -C 6 alkynyloxy, hydroxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 4 -C 6 alkynyloxy, C 2 -C 6 alkynylcarbonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 -C 6 alkynylsulfonyl, mono- or di-(C 3 -C 6 alkynyl)amino, C 1 -C 6 alkyl(C 3 -C 6 alkynyl)amino, C 2 -C 6 alkynylcarbonylamino or by C 2 -C 6 alkynylcarbonyl(C 1 -C 6 alkyl)amino; and/or the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by halo-substituted C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, mono-C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylcarbonyl(C 1 -C 6 alkyl)amino, C 2 -C 6 alkenyl, C 3 -C 6 alkenyloxy, hydroxy-C 3 -C 6 alkenyl, C 1 -C 6 alkoxy-C 2 -C 6 alkenyl, C 1 -C 6 alkoxy-C 3 -C 6 alkenyloxy, C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, mono- or di-(C 2 -C 6 alkenyl)amino, C 1 -C 6 alkyl-(C 3 -C 6 alkenyl)amino, C 2 -C 6 alkenylcarbonylamino, C 2 -C 6 alkenylcarbonyl(C 1 -C 6 alkyl)amino, C 2 -C 6 alkynyl, C 3 -C 6 alkynyloxy, hydroxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 4 -C 6 alkynyloxy, C 2 -C 6 alkynylcarbonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 -C 6 alkynylsulfonyl, mono- or di-(C 3 -C 6 alkynyl)amino, C 1 -C 6 alkyl(C 3 -C 6 alkynyl)amino, C 2 -C 6 alkynylcarbonylamino or C 2 -C 6 alkynylcarbonyl(C 1 -C 6 alkyl)amino; and/or the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by a radical of the formula COOR 50 , CONR 51 , SO 2 NR 53 R 54 or SO 2 OR 55 wherein R 50 , R 51 , R 52 , R 53 , R 54 and R 55 are each independently of the others C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl or halo-, hydroxy-, alkoxy-, mercapto-, amino-, cyano-, nitro-, alkylthio-, alkylsulfinyl- or alkylsulfonyl-substituted C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl; n is 0, 1 or 2; and R 4 , R 5 and G are each as defined in claim 1, which process comprises reacting a compound of formula II wherein R 0 , R 1 , R 2 , R 3 and n are as defined hereinbefore; R 6 is R 8 R 9 N—; R 7 is R 10 R 11 N— or R 12 O—; and R 8 , R 9 , R 10 , R 11 and R 12 are each independently of the others hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl or benzyl, wherein the phenyl ring of the benzyl group may be substituted by C 1 -C 4 alkyl, halogen, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or by nitro, in an inert organic solvent, optionally in the presence of a base, with a compound of formula IV, IVa or IVb wherein R 4 and R 5 are as defined hereinbefore and H.Hal is a hydrogen halide, and optionally converting the resulting compound of formula I wherein G is a metal ion equivalent or an ammonium cation, by salt conversion into the corresponding salt of formula I wherein G is a sulfonium or phosphonium cation, or by treatment with a Brönsted acid into the corresponding compound of formula I wherein G is hydrogen, and ‘in situ’ conversion of compounds of formula I with an electrophile of formula XII or XIId G 0 -L  (XII) or R 32 —N═C═X 3   (XIId), wherein G 0 , R 32 and X 3 are as defined hereinbefore except that R 32 is not hydrogen, and L is a leaving group, optionally in the presence of an acid-binding agent or a catalyst, to the compounds of formula Ia wherein R 0 , R 1 , R 2 , R 3 , R 4 , R 5 and n are as defined for formula I; G 0 is a group —C(O)—R 30 , —C(X 1 )—X 2 —R 31 , —C(X 3 )—N(R 32 )—R 33 , —SO 2 —R 34 or —P(X 4 )(R 35 )—R 36 ; and X 1 , X 2 , X 3 , X 4 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 and R 36 are as defined hereinbefore.

What is claimed is:  
     
         1 . A process for the preparation of a compound of formula I  
       
         
           
           
               
               
           
         
       
       wherein 
 R 0  is, each independently of any other, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, cyano-C 1 -C 6 alkyl, C 2 —C 6 haloalkenyl, cyano-C 2 -C 6 alkenyl, C 2 -C 6 haloalkynyl, cyano-C 2 -C 6 alkynyl, hydroxy, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, nitro, amino, C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 alkylaminosulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkenyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkenyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkynyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkynyl, C 1 -C 6 alkoxycarbonyl, cyano, carboxyl, phenyl or an aromatic ring that contains 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the latter two aromatic rings may be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro; or  
 R 0 , together with the adjacent substituents R 1 , R 2  and R 3 , forms a saturated or unsaturated C 3 -C 6 hydrocarbon bridge that may be interrupted by 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur and/or may be substituted by C 1 -C 4 alkyl;  
 R 1 , R 2  and R 3  are each independently of the others hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkenyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkenyl, cyano-C 2 -C 6 alkenyl, nitro-C 2 -C 6 -alkenyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkynyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 -alkynyl, cyano-C 2 -C 6 alkynyl, nitro-C 2 -C 6 alkynyl, C 3 -C 6 halocycloalkyl, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkylthio-C 1 -C 6 alkyl, cyano, C 1 -C 4 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, hydroxy, C 1 -C 10 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 haloalkoxy, C 3 -C 6 -haloalkenyloxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, mercapto, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, nitro, amino, C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino or phenoxy in which the phenyl ring may be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 -alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro;  
 R 2  also may be phenyl, naphthyl or a 5- or 6-membered aromatic ring that may contain 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by halogen, C 3 -C 8 cycloalkyl, hydroxy, mercapto, amino, cyano, nitro or by formyl; and/or  
 the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, mono-C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylcarbonyl-(C 1 -C 6 alkyl)amino, C 2 -C 6 alkenyl, C 3 -C 6 alkenyloxy, hydroxy-C 3 -C 6 alkenyl, C 1 -C 6 alkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 alkoxy-C 3 -C 6 alkenyloxy, C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, mono- or di-(C 2 -C 6 alkenyl)amino, C 1 -C 6 alkyl(C 3 -C 6 alkenyl)-amino, C 2 -C 6 alkenylcarbonylamino, C 2 -C 6 alkenylcarbonyl(C 1 -C 6 alkyl)amino, C 2 -C 6 alkynyl, C 3 -C 6 alkynyloxy, hydroxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 4 -C 6 alkynyloxy, C 2 -C 6 alkynylcarbonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 -C 6 alkynylsulfonyl, mono- or di-(C 3 -C 6 alkynyl)amino, C 1 -C 6 alkyl(C 3 -C 6 alkynyl)amino, C 2 -C 6 alkynylcarbonylamino or by C 2 -C 6 alkynylcarbonyl(C 1 -C 6 alkyl)amino; and/or  
 the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by halo-substituted C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, mono-C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylcarbonyl(C 1 -C 6 alkyl)amino, C 2 -C 6 alkenyl, C 3 -C 6 alkenyloxy, hydroxy-C 3 -C 6 alkenyl, C 1 -C 6 alkoxy-C 2 -C 6 alkenyl, C 1 -C 6 alkoxy-C 3 -C 6 alkenyloxy, C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, mono- or di-(C 2 -C 6 alkenyl)amino, C 1 -C 6 alkyl-(C 3 -C 6 alkenyl)amino, C 2 -C 6 alkenylcarbonylamino, C 2 -C 6 alkenylcarbonyl(C 1 -C 6 alkyl)amino, C 2 -C 6 alkynyl, C 3 -C 6 alkynyloxy, hydroxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 4 -C 6 alkynyloxy, C 2 -C 6 alkynylcarbonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 -C 6 alkynylsulfonyl, mono- or di-(C 3 -C 6 alkynyl)amino, C 1 -C 6 alkyl(C 3 -C 6 alkynyl)amino, C 2 -C 6 alkynylcarbonylamino or C 2 -C 6 alkynylcarbonyl(C 1 -C 6 alkyl)amino; and/or  
 the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by a radical of the formula COOR 50 , CONR 51 , SO 2 NR 53 R 54  or SO 2 OR 55  wherein R 50 , R 51 , R 52 , R 53 , R 54  and R 55  are each independently of the others C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl or halo-, hydroxy-, alkoxy-, mercapto-, amino-, cyano-, nitro-, alkylthio-, alkylsulfinyl- or alkylsulfonyl-substituted C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl;  
 n is 0, 1 or 2;  
 R 4  and R 5  are each independently of the other hydrogen, C 1 -C 12 alkyl, C 1 -C 1-2 haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 alkynyl, C 1 -C 10 alkoxy-C 1 -C 8 alkyl, poly-C 1 -C 10 alkoxy-C 1 -C 8 alkyl, C 1 -C 10 alkylthio-C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 3 -C 8 halocycloalkyl, 4- to 8-membered heterocyclyl, phenyl, α- or β-naphthyl, phenyl-C 1 -C 6 alkyl, α- or β-naphthyl-C 1 -C 6 alkyl, 5- or 6-membered heteroaryl or  5 - or 6-membered heteroaryl-C 1 -C 6 alkyl, wherein those aromatic and heteroaromatic rings may be substituted by halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, nitro or by cyano; or  
 R 4  and R 5 , together with the nitrogen atoms to which they are bonded, form a saturated or unsaturated 5- to 8-membered heterocyclic ring that 1) may be interrupted by oxygen, sulfur or by —NR 14 — and/or may be substituted by halogen, C 1 -C 10 alkyl, C 1 -C 10 haloalkyl, hydroxy, C 1 -C 6 alkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, mercapto, C 1 -C 6 alkylthio, C 3 -C 7 -cycloalkyl, heteroaryl, heteroaryl-C 1 -C 6 alkyl, phenyl, phenyl-C 1 -C 6 alkyl or by benzyloxy, wherein the phenyl rings of the last three substituents may in turn be substituted by halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or by nitro, and/or 2) may contain a fused or spiro-bound alkylene or alkenylene chain having from 2 to 6 carbon atoms that is optionally interrupted by oxygen or by sulfur, or at least one ring atom of the saturated or unsaturated heterocyclic ring bridges that alkylene or alkenylene chain; R 14  is hydrogen, C 1 -C 4 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylsulfonyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; and G is hydrogen, a metal ion equivalent or an ammonium, sulfonium or phosphonium cation, which process comprises reacting a compound of formula II  
                     
 wherein R 0 , R 1 , R 2 , R 3  and n are as defined hereinbefore; R 6  is R 8 R 9 N—; R 7  is R 10 R 11 N— or R 12 O—; and R 8 , R 9 , R 10 , R 11  and R 12  are each independently of the others hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl or benzyl, wherein the phenyl ring of the benzyl group may be substituted by C 1 -C 4 alkyl, halogen, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or by nitro, in an inert organic solvent, optionally in the presence of a base, with a compound of formula IV, IVa or IVb  
                     
 wherein R 4  and R 5  are as defined hereinbefore and H.Hal is a hydrogen halide, and optionally converting the resulting compound of formula I wherein G is a metal ion equivalent or an ammonium cation, by salt conversion into the corresponding salt of formula I wherein G is a sulfonium or phosphonium cation, or by treatment with a Brönsted acid into the corresponding compound of formula I wherein G is hydrogen.  
 
     
     
         2 . A process for the preparation of a compound of formula I according to  claim 1 , wherein R 0  is, each independently of any other, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, hydroxy, C 1 -C 6 -alkoxy, nitro, amino, C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 alkylaminosulfonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl or carboxy; and 
 R 1 , R 2  and R 3  are each independently of the others hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkylthio-C 1 -C 6 alkyl, cyano, C 1 -C 4 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, hydroxy, C 1 -C 10 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 haloalkoxy, C 3 -C 6 haloalkenyloxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, mercapto, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, nitro, amino, C 1 -C 4 alkylamino or di(C 1 -C 4 alkyl)amino.    
     
     
         3 . A process for the preparation of a compound of formula Ia  
       
         
           
           
               
               
           
         
       
       wherein R 0 , R 1 , R 2 , R 3 , R 4 , R 5  and n are as defined in  claim 1;  
 G 0  is a group —C(O)—R 30 , —C(X 1 )—X 2 —R 31 , —C(X 3 )—N(R 32 )—R 33 , —SO 2 —R 34  or —P(X 4 )(R 35 )—R 36 ;  
 X 1 , X 2 , X 3  and X 4  are each independently of the others oxygen or sulfur;  
 R 30  is unsubstituted or halo-substituted C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, C 1 -C 8 alkylthio-C 1 -C 8 alkyl, poly-C 1 -C 8 alkoxy-C 1 -C 8 alkyl or unsubstituted or halo-, C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted C 3 -C 8 cycloalkyl in which optionally at least one ring member has been replaced by oxygen and/or by sulfur, C 3 -C 6 cycloalkyl-C 1 -C 6 alkyl, heterocyclyl-C 1 -C 6 -alkyl, heteroaryl-C 1 -C 6 alkyl, unsubstituted or halo-, cyano-, nitro-, C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-, C 1 -C 6 haloalkyl-, C 1 -C 6 haloalkoxy-, C 1 -C 6 alkylthio- or C 1 -C 6 alkylsulfonyl-substituted phenyl, unsubstituted or halo-, nitro-, cyano-, C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-, C 1 -C 6 haloalkyl- or C 1 -C 6 haloalkoxy-substituted phenyl-C 1 -C 6 alkyl, unsubstituted or halo- or C 1 -C 6 alkyl-substituted heteroaryl, unsubstituted or halo- or C 1 -C 6 alkyl-substituted phenoxy-C 1 -C 6 alkyl, or unsubstituted or halo-, amino- or C 1 -C 6 alkyl-substituted heteroaryloxy-C 1 -C 6 alkyl;  
 R 31  is unsubstituted or halo-substituted C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 1 -C 8 alkoxy-C 2 -C 8 alkyl, poly-C 1 -C 8 alkoxy-C 2 -C 8 alkyl, unsubstituted or halo-, C 1 -C 6 alkyl- or C 1 -C 6 alkoxy-substituted C 3 -C 8 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 6 alkyl, heterocyclyl-C 1 -C 6 alkyl, heteroaryl-C 1 -C 6 alkyl, unsubstituted or halo-, cyano-, nitro-, C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-, C 1 -C 6 haloalkyl- or C 1 -C 6 -haloalkoxy-substituted phenyl or benzyl;  
 R 32  and R 33  are each independently of the other hydrogen, unsubstituted or halo-substituted C 1 -C 8 alkyl, C 3 -C 8 cycloalkyl, C 1 -C 8 alkoxy, C 3 -C 8 alkenyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, unsubstituted or halo-, C 1 -C 8 haloalkyl-, C 1 -C 8 alkyl- or C 1 -C 8 alkoxy-substituted phenyl or benzyl; or  
 R 32  and R 33  together form a C 3 -C 6 alkylene chain in which a carbon atom has optionally been replaced by oxygen or by sulfur;  
 R 34  is unsubstituted or halo-substituted C 1 -C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 haloalkenyl, C 3 -C 8 -alkynyl, C 3 -C 8 haloalkynyl, or unsubstituted or halo-, C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-, C 1 -C 4 haloalkyl-, C 1 -C 4 haloalkoxy-, cyano- or nitro-substituted phenyl or benzyl;  
 R 35  and R 36  are each independently of the other unsubstituted or halo-substituted C 1 -C 8 alkyl, C 1 -C 8 alkoxy, C 1 -C 8 alkylamino, di(C 1 -C 8 alkyl)amino, C 1 -C 8 alkylthio, C 2 -C 8 alkenylthio, C 3 -C 7 -cycloalkylthio, or unsubstituted or halo-, nitro-, cyano-, C 1 -C 4 alkoxy-, C 1 -C 4 haloalkoxy-, C 1 -C 4 alkylthio-, C 1 -C 4 haloalkylthio-, C 1 -C 4 alkyl- or C 1 -C 4 haloalkyl-substituted phenyl, phenoxy or phenylthio,  
 which process comprises reacting a compound of formula I prepared in accordance with  claim 1 , directly in the reaction solution in a one-pot reaction without isolation, optionally in the presence of an acid-binding agent or a catalyst, with an electrophile of formula XII or XIId  
 G 0-L   (XII) or R 32 —N═C═X 3   (XIId),  
 wherein G 0 , R 32  and X 3  are as defined hereinbefore except that R 32  is not hydrogen, and L is a leaving group.  
 
     
     
         4 . A process according to  claim 2 , wherein R 1 , R 2  and R 3  are each independently of the others hydrogen, halogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 1 -C 4 haloalkyl, C 3 - or C 4 -haloalkenyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, hydroxy, C 1 -C 4 alkoxy, C 3 - or C 4 -alkenyloxy, C 3 - or C 4 -alkynyloxy, C 1 -C 4 haloalkoxy, nitro or amino.  
     
     
         5 . A process according to  claim 1 , wherein R 4  and R 5 , together with the nitrogen atoms to which they are bonded, form a saturated or unsaturated, 6- or 7-membered heterocyclic ring that 1) may be interrupted once by oxygen or by sulfur and/or 2) may contain a fused or spiro-bound alkylene chain having from 2 to 5 carbon atoms that is optionally interrupted once or twice by oxygen or by sulfur, or at least one ring atom of the saturated or unsaturated heterocyclic ring bridges that alkylene chain.  
     
     
         6 . A process according to  claim 1 , which comprises using a compound of formula II wherein R 8 , R 9 , R 10 , R 11  and R 12  are hydrogen, C 1 -C 6 alkyl or benzyl.  
     
     
         7 . A process according to  claim 1 , wherein the compound of formula IV, IVa or IVb is used in an equimolar amount or, preferably, in an excess of from 5 to 50 mol %, based on the compound of formula II.  
     
     
         8 . A process according to  claim 1 , wherein the reaction is carried out at a reaction temperature of from 0° to 200° C.  
     
     
         9 . A process according to  claim 1 , which comprises using as the inert organic solvent for the reaction an aromatic, aliphatic or cycloaliphatic hydrocarbon, halogenated hydrocarbon, an ether, nitrile, dialkyl sulfoxide, amide or lactam, an alcohol, glycol or polyalcohol, a carboxylic acid, or a mixture of such solvents.  
     
     
         10 . A process according to  claim 9 , which comprises using as the solvent toluene, one of the xylene isomers ortho-, meta- and para-xylene, methylcyclohexane, chlorobenzene or one of the dichlorobenzene isomers 1,2-, 1,3- and 1,4-dichlorobenzene.  
     
     
         11 . A process according to  claim 1 , which comprises carrying out the condensation reaction in an inert gas atmosphere.  
     
     
         12 . A process according to  claim 1 , which comprises carrying out the reaction of a compound of formula II with a compound of formula IV with or without the addition of a base.  
     
     
         13 . A process according to  claim 1 , which comprises carrying out the reaction of a compound of formula II with a compound of formula IVa or IVb in the presence of a base.  
     
     
         14 . A process according to  claim 13 , which comprises using as base a tertiary amine, pyridine, alkali metal alcoholate, or alkali metal or alkaline earth metal hydride, hydroxide, carbonate or hydrogen carbonate.  
     
     
         15 . A process according to  claim 14 , which comprises using the base in catalytic amounts or in a molar excess of up to 5, based on the compound of formula II.  
     
     
         16 . The use of a compound of formula I according to  claim 1  prepared in accordance with the invention, wherein G is hydrogen, a metal ion equivalent or an ammonium, sulfonium or phosphonium cation, for the ‘in situ’ preparation of a compound of formula Ia wherein G 0  is a group —C(O)—R 30 , —C(X 1 )—X 2 —R 31 , —C(X 3 )—N(R 32 )—R 33 , —SO 2 —R 34  or —P(X 4 )(R 35 )—R 36 ; and R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , X 1 , X 2 , X 3  and X 4  are as defined hereinbefore.  
     
     
         17 . A compound of formula I  
       
         
           
           
               
               
           
         
       
       wherein R 0  is, each independently of any other, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 haloalkyl, cyano-C 1 -C 6 alkyl, C 2 -C 6 haloalkenyl, cyano-C 2 -C 6 alkenyl, C 2 -C 6 haloalkynyl, cyano-C 2 -C 6 alkynyl, hydroxy, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, nitro, amino, C 1 -C 6 -alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 -alkylaminosulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkenyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkenyl, C 1 -C 6 -alkylcarbonyl-C 2 -C 6 alkynyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkynyl, C 1 -C 6 alkoxycarbonyl, cyano, carboxyl, phenyl or an aromatic ring that contains 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the latter two aromatic rings may be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro; or R 0 , together with the adjacent substituents R 1 , R 2  and R 3 , forms a saturated or unsaturated C 3 -C 6 hydrocarbon bridge that may be interrupted by 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur and/or may be substituted by C 1 -C 4 alkyl; R 1 , R 2  and R 3  are each independently of the others hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkenyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkenyl, cyano-C 2 -C 6 alkenyl, nitro-C 2 -C 6 alkenyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkynyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkynyl, cyano-C 2 -C 6 alkynyl, nitro-C 2 -C 6 alkynyl, C 3 -C 6 -halocycloalkyl, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkylthio-C 1 -C 6 alkyl, cyano, C 1 -C 4 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, hydroxy, C 1 -C 10 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 haloalkoxy, C 3 -C 6 haloalkenyloxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, mercapto, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, nitro, amino, C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)-amino or phenoxy in which the phenyl ring may be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro; 
 R 2  also may be phenyl, naphthyl or a 5- or 6-membered aromatic ring that may contain 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by halogen, C 3 -C 8 cycloalkyl, hydroxy, mercapto, amino, cyano, nitro or by formyl; and/or  
 the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, mono-C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylcarbonyl-(C 1 -C 6 alkyl)amino, C 2 -C 6 alkenyl, C 3 -C 6 alkenyloxy, hydroxy-C 3 -C 6 alkenyl, C 1 -C 6 alkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 alkoxy-C 3 -C 6 alkenyloxy, C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkenylthio, C 2 -C 6 -alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, mono- or di-(C 2 -C 6 alkenyl)amino, C 1 -C 6 alkyl(C 3 -C 6 -alkenyl)amino, C 2 -C 6 alkenylcarbonylamino, C 2 -C 6 alkenylcarbonyl(C 1 -C 6 alkyl)amino, C 2 -C 6 -alkynyl, C 3 -C 6 alkynyloxy, hydroxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 4 -C 6 alkynyloxy, C 2 -C 6 alkynylcarbonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 -C 6 alkynylsulfonyl, mono- or di-(C 3 -C 6 alkynyl)amino, C 1 -C 6 alkyl(C 3 -C 6 alkynyl)amino, C 2 -C 6 alkynylcarbonylamino or by C 2 -C 6 alkynylcarbonyl(C 1 -C 6 alkyl)amino; and/or  
 the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by halo-substituted C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, mono-C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylcarbonyl(C 1 -C 6 alkyl)amino, C 2 -C 6 alkenyl, C 3 -C 6 alkenyloxy, hydroxy-C 3 -C 6 alkenyl, C 1 -C 6 alkoxy-C 2 -C 6 alkenyl, C 1 -C 6 alkoxy-C 3 -C 6 alkenyloxy, C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, mono- or di-(C 2 -C 6 alkenyl)amino, C 1 -C 6 alkyl-(C 3 -C 6 alkenyl)amino, C 2 -C 6 alkenylcarbonylamino, C 2 -C 6 alkenylcarbonyl(C 1 -C 6 alkyl)amino, C 2 -C 6 alkynyl, C 3 -C 6 alkynyloxy, hydroxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 4 -C 6 alkynyloxy, C 2 -C 6 alkynylcarbonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 -C 6 alkynylsulfonyl, mono- or di-(C 3 -C 6 alkynyl)amino, C 1 -C 6 alkyl(C 3 -C 6 alkynyl)amino, C 2 -C 6 alkynylcarbonylamino or C 2 -C 6 alkynylcarbonyl(C 1 -C 6 alkyl)amino; and/or  
 the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by a radical of the formula COOR 50 , CONR 51 , SO 2 NR 53 R 54  or SO 2 OR 55  wherein R 50 , R 51 , R 52 , R 53 , R 54  and R 55  are each independently of the others C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl or halo-, hydroxy-, alkoxy-, mercapto-, amino-, cyano-, nitro-, alkylthio-, alkylsulfinyl- or alkylsulfonyl-substituted C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl;  
 n is 1 or 2; R 4  and R 5 , together with the nitrogen atoms to which they are bonded, form a saturated or unsaturated 5- to 8-membered heterocyclic ring that 1) is interrupted by oxygen, sulfur or by —NR 14 — and may be substituted by halogen, C 1 -C 10 alkyl, C 1 -C 10 haloalkyl, hydroxy, C 1 -C 6 alkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, mercapto, C 1 -C 6 alkylthio, C 3 -C 7 -cycloalkyl, heteroaryl, heteroaryl-C 1 -C 6 alkyl, phenyl, phenyl-C 1 -C 6 alkyl or by benzyloxy, wherein the phenyl rings of the last three substituents may in turn be substituted by halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or by nitro, and 2) may contain a fused or spiro-bound alkylene or alkenylene chain having from 2 to 6 carbon atoms that is optionally interrupted by oxygen or by sulfur, or at least one ring atom of the saturated or unsaturated heterocyclic ring bridges that alkylene or alkenylene chain; R 14  is hydrogen, C 1 -C 4 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylsulfonyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; and G is hydrogen or a metal ion equivalent or an ammonium, sulfonium or phosphonium cation.  
 
     
     
         18 . A compound of formula Ia  
       
         
           
           
               
               
           
         
       
       wherein R 0  is, each independently of the any other, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 haloalkyl, cyano-C 1 -C 6 alkyl, C 2 -C 6 haloalkenyl, cyano-C 2 -C 6 alkenyl, C 2 -C 6 haloalkynyl, cyano-C 2 -C 6 alkynyl, hydroxy, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, nitro, amino, C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylsulfonylamino, C 1 -C 6 alkylaminosulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl-C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkenyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 -alkenyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkynyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkynyl, C 1 -C 6 alkoxycarbonyl, cyano, carboxyl, phenyl or an aromatic ring that contains 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the latter two aromatic rings may be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro; or R 0 , together with the adjacent substituents R 1 , R 2  and R 3 , forms a saturated or unsaturated C 3 -C 6 hydrocarbon bridge that may be interrupted by 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur and/or may be substituted by C 1 -C 4 alkyl; R 1 , R 2  and R 3  are each independently of the others hydrogen, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkenyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkenyl, cyano-C 2 -C 6 alkenyl, nitro-C 2 -C 6 alkenyl, C 2 -C 6 haloalkynyl, C 1 -C 6 alkoxycarbonyl-C 2 -C 6 alkynyl, C 1 -C 6 alkylcarbonyl-C 2 -C 6 alkynyl, cyano-C 2 -C 6 alkynyl, nitro-C 2 -C 6 alkynyl, C 3 -C 6 halocycloalkyl, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkylthio-C 1 -C 6 alkyl, cyano, C 1 -C 4 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, hydroxy, C 1 -C 10 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 1 -C 6 haloalkoxy, C 3 -C 6 haloalkenyloxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, mercapto, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, nitro, amino, C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino or phenoxy in which the phenyl ring may be substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or by nitro; 
 R 2  also may be phenyl, naphthyl or a 5- or 6-membered aromatic ring that may contain 1 or 2 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, wherein the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by halogen, C 3 -C 8 cycloalkyl, hydroxy, mercapto, amino, cyano, nitro or by formyl; and/or  
 the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, mono-C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylcarbonyl-(C 1 -C 6 alkyl)amino, C 2 -C 6 alkenyl, C 3 -C 6 alkenyloxy, hydroxy-C 3 -C 6 alkenyl, C 1 -C 6 alkoxy-C 2 -C 6 -alkenyl, C 1 -C 6 alkoxy-C 3 -C 6 alkenyloxy, C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenyisulfonyl, mono- or di-(C 2 -C 6 alkenyl)amino, C 1 -C 6 alkyl(C 3 -C 6 alkenyl)-amino, C 2 -C 6 alkenylcarbonylamino, C 2 -C 6 alkenylcarbonyl(C 1 -C 6 alkyl)amino, C 2 -C 6 alkynyl, C 3 -C 6 alkynyloxy, hydroxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 4 -C 6 alkynyloxy, C 2 -C 6 alkynylcarbonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 -C 6 alkynylsulfonyl, mono- or di-(C 3 -C 6 alkynyl)amino, C 1 -C 6 alkyl(C 3 -C 6 alkynyl)amino, C 2 -C 6 alkynylcarbonylamino or by C 2 -C 6 alkynylcarbonyl(C 1 -C 6 alkyl)amino; and/or  
 the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by halo-substituted C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, mono-C 1 -C 6 alkylamino, di(C 1 -C 6 alkyl)amino, C 1 -C 6 alkylcarbonylamino, C 1 -C 6 alkylcarbonyl(C 1 -C 6 alkyl)amino, C 2 -C 6 alkenyl, C 3 -C 6 alkenyloxy, hydroxy-C 3 -C 6 alkenyl, C 1 -C 6 alkoxy-C 2 -C 6 alkenyl, C 1 -C 6 alkoxy-C 3 -C 6 alkenyloxy, C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkenylthio, C 2 -C 6 alkenylsulfinyl, C 2 -C 6 alkenylsulfonyl, mono- or di-(C 2 -C 6 alkenyl)amino, C 1 -C 6 alkyl-(C 3 -C 6 alkenyl)amino, C 2 -C 6 alkenylcarbonylamino, C 2 -C 6 alkenylcarbonyl(C 1 -C 6 alkyl)amino, C 2 -C 6 alkynyl, C 3 -C 6 alkynyloxy, hydroxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 3 -C 6 alkynyl, C 1 -C 6 alkoxy-C 4 -C 6 alkynyloxy, C 2 -C 6 alkynylcarbonyl, C 2 -C 6 alkynylthio, C 2 -C 6 alkynylsulfinyl, C 2 -C 6 alkynylsulfonyl, mono- or di-(C 3 -C 6 alkynyl)amino, C 1 -C 6 alkyl(C 3 -C 6 alkynyl)amino, C 2 -C 6 alkynylcarbonylamino or C 2 -C 6 alkynylcarbonyl(C 1 -C 6 alkyl)amino; and/or  
 the phenyl ring, the naphthyl ring system and the 5- or 6-membered aromatic ring may be substituted by a radical of the formula COOR 50 , CONR 51 , SO 2 NR 5 R 54  or SO 20 R 5  wherein R 50 , R 51 , R 52 , R 53 , R 54  and R 55  are each independently of the others C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl or halo-, hydroxy-, alkoxy-, mercapto-, amino-, cyano-, nitro-, alkylthio-, alkylsulfinyl- or alkylsulfonyl-substituted C 1 -C 6 alkyl, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl;  
 n is 1 or 2; R 4  and R 5 , together with the nitrogen atoms to which they are bonded, form a saturated or unsaturated 5- to 8-membered heterocyclic ring that 1) is interrupted by oxygen, sulfur or by —NR 14 — and may be substituted by halogen, C 1 -C 10 alkyl, C 1 -C 10 haloalkyl, hydroxy, C 1 -C 6 alkoxy, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, mercapto, C 1 -C 6 alkylthio, C 3 -C 7 -cycloalkyl, heteroaryl, heteroaryl-C 1 -C 6 alkyl, phenyl, phenyl-C 1 -C 6 alkyl or by benzyloxy, wherein the phenyl rings of the last three substituents may in turn by substituted by halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or by nitro, and 2) may contain a fused or spiro-bound alkylene or alkenylene chain having from 2 to 6 carbon atoms that is optionally interrupted by oxygen or by sulfur, or at least one ring atom of the saturated or unsaturated heterocyclic ring bridges that alkylene or alkenylene chain; R 14  is hydrogen, C 1 -C 4 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylsulfonyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; and G 0  is a group —C(O)—R 30 , —C(X 1 )—X 2 —R 31  or —SO 2 —R 34 ;  
 X 1 , X 2 , X 3  and X 4  are each independently of the others oxygen or sulfur;  
 R 30  is unsubstituted or halo-substituted C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 1 -C 8 alkoxy-C 1 -C 8 alkyl, C 1 -C 8 alkylthio-C 1 -C 8 alkyl, poly-C 1 -C 8 alkoxy-C 1 -C 8 alkyl or unsubstituted or halo-substituted C 3 -C 8 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 6 alkyl, heterocyclyl-C 1 -C 6 alkyl, heteroaryl-C 1 -C 6 alkyl, unsubstituted or halo-, cyano-, nitro-, C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-, C 1 -C 6 haloalkyl-, C 1 -C 6 haloalkoxy-, C 1 -C 6 alkylthio- or C 1 -C 6 alkylsulfonyl-substituted phenyl, unsubstituted or halo-, nitro-, cyano-, C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-, C 1 -C 6 haloalkyl- or C 1 -C 6 haloalkoxy-substituted phenyl-C 1 -C 6 alkyl, unsubstituted or halo- or C 1 -C 6 alkyl-substituted heteroaryl, unsubstituted or halo- or C 1 -C 6 alkyl-substituted phenoxy-C 1 -C 6 alkyl, or unsubstituted or halo-, amino- or C 1 -C 6 alkyl-substituted heteroaryloxy-C 1 -C 6 alkyl; R 31  is unsubstituted or halo-substituted C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 1 -C 8 alkoxy-C 2 -C 8 alkyl, poly-C 1 -C 8 alkoxy-C 2 -C 8 alkyl, unsubstituted or halo- or C 1 -C 6 alkoxy-substituted C 3 -C 8 cycloalkyl, C 3 -C 6 cycloalkyl-C 1 -C 6 alkyl, heterocyclyl-C 1 -C 6 alkyl, heteroaryl-C 1 -C 6 alkyl, unsubstituted or halo-, cyano-, nitro-, C 1 -C 6 -alkyl-, C 1 -C 6 alkoxy-, C 1 -C 6 haloalkyl- or C 1 -C 6 haloalkoxy-substituted phenyl or benzyl; R 34  is unsubstituted or halo-substituted C 1 -C 8 alkyl, or unsubstituted or halo-, C 1 -C 6 alkyl-, C 1 -C 6 -alkoxy-, C 1 -C 4 haloalkyl-, C 1 -C 4 haloalkoxy-, cyano- or nitro-substituted phenyl.  
 
     
     
         19 . A compound of formula II  
       
         
           
           
               
               
           
         
       
       wherein R 0 , R 1 , R 2 , R 3 , R 6 , R 7  and n are as defined in  claim 1 .  
     
     
         20 . A compound of formula II according to  claim 19 , wherein R 1 , R 2  and R 3  are each independently of the others hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, hydroxy, C 1 -C 4 alkoxy, C 3 — or C 4 -alkenyloxy, C 3 — or C 4 -alkynyloxy, C 1 -C 4 haloalkoxy, nitro or amino.  
     
     
         21 . A compound of formula II according to  claim 19 , wherein R 1  is C 2 -C 6 alkyl.  
     
     
         22 . A compound of formula II according to  claim 19 , wherein n is 0.  
     
     
         23 . A compound of formula II according to  claim 22 , wherein R 1  is C 2 -C 4 alkyl, C 1 -C 4 alkoxy, C 2 -C 4 alkynyl or C 3 -C 6 cycloalkyl and R 3  is C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 2 -C 4 alkynyl or C 3 -C 6 -cycloalkyl sind.  
     
     
         24 . A compound of formula II according to  claim 19 , wherein R 1  is C 2 -C 6 alkynyl.  
     
     
         25 . A compound of formula II according to  claim 19 , wherein R 1  and R 3  are each independently of the other C 2 -C 6 alkyl, C 2 -C 6 alkynyl, C 1 -C 10 alkoxy or C 3 -C 6 cycloalkyl.  
     
     
         26 . A compound of formula II according to  claim 25 , wherein R 1  is C 2 -C 6 alkyl and R 3  is C 2 -C 6 alkyl, C 2 -C 6 alkynyl or C 1 -C 10 alkoxy.  
     
     
         27 . A compound of formula II according to  claim 19 , wherein R 6  is R 8 R 9 N— and R 7  is R 10 R 11 N—; and R 8 , R 9 , R 10  and R 11  are as defined hereinbefore.