2,4-diamino-1,3,5-triazines, their preparation, and their use as herbicides and plant growth regulators

Abstract

The invention is in the technical field of the crop protection agents, such as herbicides and plant growth regulators, in particular of the herbicides for the selective control of harmful plants in crops of useful plants.

1 . A compound of the formula (I) or a salt thereof  
       
         
           
           
               
               
           
         
       
       in which 
 R 1  is aryl which is unsubstituted or substituted, or (C 3 -C 9 )cycloalkyl which is unsubstituted or substituted, or heterocyclyl which is substituted or unsubstituted, or 
 (C 1 -C 6 )alkyl, (C 2 -C 6 )alkenyl or (C 2 -C 6 )alkynyl,  
  each of the last-mentioned 3 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, nitro, thiocyanato, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 4 )alkenyloxy, (C 2 -C 4 )haloalkenyloxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )haloalkylsulfonyl and (C 3 -C 9 )cycloalkyl which is unsubstituted or substituted, and phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, and radicals of the formulae R′—C(═Z′)—, R′—C(═Z′)—Z—, R′—Z—C(═Z′)—, R′R″N—C(═Z′)—, R′—Z—C(═Z′)—O—, R′R″N—C(═Z′)—Z—, R′—Z—C(═Z′)—NR″— and R′R″N—C(═Z′)—NR′″— in which R′, R″ and R′″ in each case independently of one another are (C 1 -C 6 )alkyl, aryl, aryl-(C 1 -C 6 )alkyl, (C 3 -C 9 )cycloalkyl or (C 3 -C 9 )cycloalkyl-(C 1 -C 6 )alkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted, and in which Z and Z′ independently of one another are in each case an oxygen or sulfur atom,  
 
 R 2  is (C 3 -C 9 )cycloalkyl which is unsubstituted or substituted, (C 4 -C 9 )cycloalkenyl which is unsubstituted or substituted, heterocyclyl which is unsubstituted or substituted, or phenyl, which is unsubstituted or substituted, or  
 R 3  is hydrogen, (C 1 -C 6 )alkyl, aryl or (C 3 -C 9 )cycloalkyl, each of the last-mentioned 3 radicals being unsubstituted or substituted, or a radical of the formula —N(B 1 —D 1 )(B 2 —D 2 ) or —NR′—N(B 1 —D 1 )(B 2 —D 2 ) in which B 1 , B 2 , D 1  and D 2  are in each case as defined below and R′=hydrogen, (C 1 -C 6 )alkyl or [(C 1 -C 4 )alkyl]carbonyl,  
 R 4  is a radical of the formula —B 3 —D 3 B 3  and D 3  being as defined below,  
 A 1  is straight-chain alkylene having 1 to 5 carbon atoms or straight-chain alkenylene or alkynylene, each of which has 2 to 5 carbon atoms, each of the three last-mentioned divalent radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, thiocyanato and radicals of the formula —B 4 —D 4 , B 4  and D 4  being as defined below,  
 A 2  is a direct bond or straight-chain alkylene having 1 to 4 carbon atoms or straight-chain alkenylene or alkynylene, each of which has 2 to 5 carbon atoms, each of the three last-mentioned divalent radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, thiocyanato and radicals of the formula —B 5 —D 5  or a divalent radical of the formula V 1 , V 2 , V 3 , V 4  or V 5 ,  
 —CR 6 R 7 —W*—CR 8 R 9 —  (V 1 ) —CR 10 R 11 —W*—CR 12 R 13 —CR 14 R 15 —  (V 2 ) —CR 16 R 17 —CR 18 R 19 —W*—CR 20 R 21 —(V 3 ) —CR 22 R 23 —CR 24 R 25 —W*—  (V 4 ) —CR 26 R 27 —W*—  (V 5 )  
 each of the radicals R 6  to R 27  in each case independently of one another being hydrogen, halogen, nitro, cyano, thiocyanato or a radical of the formula —B 6 —D 6 ,  
 W* is in each case an oxygen atom, a sulfur atom or a group of the formula N(B 7 —D 7 ) and  
 B 5 , B 6 , B 7 , D 5 , B 8  and D 7  are as defined below,  
 B 1 , B 2 , B 3  and B 7  in each case independently of one another are a direct bond or a divalent group of the formulae —C(═Z*)—, —C(═Z*)—Z**—, —C(═Z*)—NH— or —C(═Z*)—NR*—, Z* being an oxygen or sulfur atom, Z** an oxygen or sulfur atom and R* (C 1 -C 6 )alkyl, aryl, aryl-(C 1 -C 6 )alkyl, (C 3 -C 9 )cycloalkyl or (C 3 -C 9 )cycloalkyl-(C 1 -C 6 )alkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted,  
 B 4 , B 5  and B 6  in each case independently of one another are a direct bond or a divalent group of the formulae —O—, —S(O) p —, —S(O) p —O—, —O—S(O) p —, —CO—, —O—CO—, —CO—O—, —S—CO—, —CO—S—, —S—CS—, —CS—S—, —O—CO—O—, —NR o —, —O—NR o —, —NR o —O—, —NR o —CO—, —CO—NR o —, —O—CO—NR o — or —NR o —CO—O—, p being the integer 0, 1 or 2 and R o  being hydrogen, (C 1 -C 6 )alkyl, aryl, aryl-(C 1 -C 6 )alkyl, (C 3 -C 9 )cycloalkyl or (C 3 -C 9 )cycloalkyl-(C 1 -C 6 )alkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted,  
 D 1 , D 2 , D 3 , D 4 , D 5  and D 6  in each case independently of one another are hydrogen, (C 1 -C 6 )alkyl, aryl, aryl-(C 1 -C 6 )alkyl, (C 3 -C 9 )cycloalkyl or (C 3 -C 9 )cycloalkyl-(C 1 -C 6 )alkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted,  
  or in each case two radicals D 5  of two groups —B 5 —D 5  which are bonded to a carbon atom are linked to each other and form an alkylene group having 2 to 4 carbon atoms, this alkylene group being unsubstituted or substituted by one or more radicals selected from the group consisting of (C 1 -C 4 )alkyl and (C 1 -C 4 )alkoxy,  
 (X) n  is n substituents X, where the X in each case independently of one another are halogen, hydroxyl, amino, nitro, formyl, carboxyl, cyano, thiocyanato, aminocarbonyl or (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, mono(C 1 -C 6 )alkylamino, di(C 1 -C 4 )alkylamino, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, [(C 1 -C 6 )alkyl]carbonyl, [(C 1 -C 6 )alkoxy]carbonyl, mono(C 1 -C 6 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, N—(C 1 -C 6 )alkanoylamino or N—(C 1 -C 4 )alkanoyl-N—(C 1 -C 4 )alkylamino,  
  each of the last-mentioned 13 radicals being unsubstituted or substituted, preferably unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, cyano, thiocyanato, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 9 )cycloalkyl, (C 3 -C 9 )cycloalkylamino, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyclylamino,  
  each of the last-mentioned 8 radicals being unsubstituted or having one or more substituents selected from the group consisting of halogen, nitro, cyano, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )haloalkoxy, formyl, (C 1 -C 4 )alkylcarbonyl and (C 1 -C 4 )alkoxycarbonyl,  
 or is (C 3 -C 9 )cycloalkyl, (C 3 -C 9 )cycloalkoxy, (C 3 -C 9 )cycloalkylamino, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclylamino,  
  each of the last-mentioned 11 radicals being unsubstituted or substituted,  
 or two adjacent radicals X together are a fused cycle which has 4 to 6 ring atoms and is carbocyclic or which contains hetero ring atoms selected from the group consisting of O, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )alkyl and oxo,  
 n is 0, 1, 3, 4 or 5, and  
 heterocyclyl in the abovementioned radicals independently of one another is in each case a heterocyclic radical having 3 to 7 ring atoms and 1 to 3 heteroatoms selected from the group consisting of N, O and S, where  
 a) the total of the carbon atoms in the radicals A 1  and A 2 —R 2  amounts to at least 6 carbon atoms or  
 b) the total of the carbon atoms in the radicals A 1  and A 2 —R 2  amounts to 5 carbon atoms and A 1  is a group of the formula —CH 2 — or —CH 2 CH 2 — and R 1  is (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 2 -C 6 )haloalkenyl or (C 3 -C 9 )cycloalkyl which is unsubstituted or substituted.  
 
     
     
         2 . A compound of the formula (I) or a salt thereof as claimed in  claim 1 , wherein 
 R 1  is phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano, thiocyanato, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 9 )cycloalkyl, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulfonyl and (C 1 -C 4 )haloalkylsulfonyl,     or     (C 3 -C 9 )cycloalkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, cyano, thiocyanato, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino and di(C 1 -C 4 )alkylamino,     or     heterocyclyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 9 )cycloalkyl, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulfonyl and (C 1 -C 4 )haloalkylsulfonyl,     or     (C 1 -C 8 )alkyl, (C 2 -C 6 )alkenyl or (C 2 -C 6 )alkynyl, each of the last-mentioned 3 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, nitro, thiocyanato, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 2 -C 4 )alkenyloxy, (C 2 -C 4 )haloalkenyloxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )alkylsulfinyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfinyl, (C 1 -C 4 )haloalkylsulfonyl and (C 3 -C 6 )cycloalkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, cyano, thiocyanato, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino and di(C 1 -C 4 )alkylamino, and phenyl and heterocyclyl, each of the two last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 9 )cycloalkyl, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylamino-carbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulfonyl and (C 1 -C 4 )haloalkylsulfonyl, and radicals of the formulae R′—C(═Z′)—, R′—C(═Z′)—Z—, R′—Z—C(═Z′)—, R′R″N—C(═Z′)—, R′—Z—C(═Z′)—O—, R′R″N—C(═Z′)—Z—, R′—Z—C(═Z′)—NR″— and R′R″N—C(═Z)—NR′″— in which R′, R″ and R′″ in each case independently of one another are (C 1 -C 4 )alkyl, phenyl, phenyl-(C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl or (C 3 -C 6 )cycloalkyl-(C 1 -C 4 )alkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, cyano, thiocyanato, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkynyl, (C 3 -C 6 )cycloalkyl and in the case of cyclic radicals also (C 1 -C 4 )alkyl and (C 1 -C 4 )haloalkyl, and in which Z and Z independently of one another are in each case an oxygen or sulfur atom.    
     
     
         3 . A compound of the formula (I) or a salt thereof as claimed in  claim 1 , wherein 
 R 2  is (C 3 -C 9 )cycloalkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of the radicals A), B), C) and D), where 
 Group A) is composed of the radicals halogen, hydroxyl, amino, nitro, formyl, carboxyl, aminocarbonyl, sulfo, cyano, thiocyanato and oxo,  
 Group B) is composed of the radicals (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylthio, mono(C 1 -C 6 )alkylamino, di(C 1 -C 4 )alkylamino, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 3 -C 9 )cycloalkyl, (C 4 -C 9 )cycloalkenyl, (C 1 -C 6 )alkylidene, (C 4 -C 9 )cycloalkylidene, radicals of the formulae R′—C(═Z)—, R′—C(—Z′)—Z—, R′—Z—C(═Z′)—, R′R″N—C(═Z)—, R′—Z—C(═Z′)—O—, R′R″N—C(═Z′)—Z—, R′—Z—C(═Z′)—NR″-and R′R″N—C(═Z′)—NR′″— where R′, R″ and R′″ in each case independently of one another are (C 1 -C 6 )alkyl, phenyl, phenyl-(C 1 -C 6 )alkyl, (C 3 -C 9 )cycloalkyl or (C 3 -C 9 )cycloalkyl-(C 1 -C 6 )alkyl and where Z and Z independently of one another are in each case an oxygen or sulfur atom,  
 Group C) is composed of radicals as shown for group B), but each radical being substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano, thiocyanato, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 9 )cycloalkyl, (C 4 -C 9 )cycloalkylene, (C 4 -C 9 )cycloalkylidene, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyclylamino, each of the last-mentioned 21 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkoxy, formyl, (C 1 -C 4 )alkylcarbonyl and (C 1 -C 4 )alkoxycarbonyl and, in the case of cyclic radicals, also (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl and (C 1 -C 6 )alkylidene,  
  and in the case of cyclic radicals also (C 1 -C 6 )alkyl, (C 1 -C 6 )haloalkyl and (C 1 -C 6 )alkylidene, and  
 Group D) is composed of divalent or trivalent aliphatic bridges having 1 to 6, preferably 1 to 4, carbon atoms which, in the case of divalent bridges, connect two and in the case of trivalent bridges three carbon atoms of the cyclic skeleton and the radical R 1  thus represents the radical of a bicycle or tricycle, each of the bridges being unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, nitro, cyano, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )haloalkoxy, formyl, (C 1 -C 4 )alkylcarbonyl, (C 1 -C 4 )alkoxycarbonyl and oxo,  
    or     (C 4 -C 4 )cycloalkenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of the radicals A), B), C) and D) as they are defined as radicals for R 2 ═(C 3 -C 9 )cycloalkyl,     or     heterocyclyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of the radicals A), B), C) and D) as they are defined as radicals for R 2 ═(C 3 -C 9 )cycloalkyl,     or    phenyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of the radicals A), B) and C) as they are defined as radicals for R 2 ═(C 3 -C 9 )cycloalkyl.    
     
     
         4 . A compound of the formula (I) or a salt thereof as claimed in  claim 1 , wherein 
 R 3  is hydrogen, (C 1 -C 4 )alkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, cyano, thiocyanato, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino and di(C 1 -C 4 )alkylamino, or phenyl or (C 3 -C 6 )cycloalkyl, each of the last-mentioned 2 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 9 )cycloalkyl, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylamino-carbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulfonyl and (C 1 -C 4 )haloalkylsulfonyl, or a radical of the formula N(B 1 —D 1 )(B 2 —D 2 ),    R 4  is a radical of the formula —B 3 —D 3 ,    A 1  is straight-chain alkylene having 1 to 5 carbon atoms or straight-chain alkenylene or alkynylene, each of which having 2 to 5 carbon atoms, each of the three last-mentioned divalent radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, thiocyanato and a radical of the formula —B 4 —D 4 ,    B 4  is a direct bond or a divalent group of the formulae —O—, —SO 2 —, —CO, —O—CO—, —NR o —, —NR o —CO—, —CO—NR o —, —O—CO—NR o — or —NR o —CO—O—,    where    R o  and D 4  independently of one another are in each case hydrogen, (C 1 -C 4 )alkyl, phenyl, phenyl-(C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl or (C 3 -C 6 )cycloalkyl-(C 1 -C 4 )alkyl, each of the last-mentioned 5 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 9 )cycloalkyl, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl and in the case of cyclic radicals also (C 1 -C 4 )alkyl and (C 1 -C 4 )haloalkyl,    A 2  is a direct bond or a group of the formula —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 , each of the 4 last-mentioned divalent radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, nitro, cyano, thiocyanato and radicals of the formula —B 5 —D 5 —, or a divalent radical of the formula V 1 , V 2 , V 3 , V 4  or V 5 ,    —CR 6 R 7 —W*—CR 8 R 9 —  (V 1 ) —CR 10 R 11 —W*—CR 12 R 13 —CR 14 R 15 —  (V 2 ) —CR 16 R 17 —CR 18 R 19 —W*—CR 20 R 21 —(V 3 ) —CR 22 R 23 —CR 24 R 25 —W*—  (V 4 ) —CR 26 R 27 —W*—  (V 5 )    where each of the radicals R 6  to R 27  in each case independently of one another is hydrogen, halogen, nitro, cyano, thiocyanato or a radical of the formula —B 6 —D 6 ,    W* is in each case O, S or a group of the formula N(B 7 —D 7 ),    B 1 , B 2 , B 3  and B 7  independently of one another are a direct bond or a divalent group of the formulae —C(═Z*)—, —C(═Z*)—Z**—, —C(═Z*)—NH— or —C(═Z*)—NR*—, where Z*═O or S, Z**═O or S and R*═(C 1 -C 4 )alkyl, phenyl, phenyl-(C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl or (C 3 -C 6 )cycloalkyl-(C 1 -C 4 )alkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano, thiocyanato, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 9 )cycloalkyl, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl and in the case of cyclic radicals also (C 1 -C 4 )alkyl and (C 1 -C 4 )haloalkyl; B 4 , B 5  and B 8  independently of one another are a direct bond or a divalent group of the formulae —O—, —S(O) p —, —S(O) p —O—, —O—S(O) p —, —CO—, —O—CO—, —CO—O—, —S—CO—, —CO—S—, —S—CS—, —CS—S—, —O—CO—O—, —NR o —, —O—NR o —, —NR o —O—, —NR o —CO—, —CO—NR o —, —O—CO—NR o — or —NR o —CO—O—, where p is the integer 0, 1 or 2 and R o =hydrogen, (C 1 -C 4 )alkyl, phenyl, phenyl-(C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl or (C 3 -C 6 )cycloalkyl-(C 1 -C 4 )alkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano, thiocyanato, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 9 )cycloalkyl, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl and in the case of cyclic radicals also (C 1 -C 4 )alkyl and (C 1 -C 4 )haloalkyl,    D 1 , D 2 , D 3 , D 4 , D 5  and D 6  independently of one another are hydrogen,     (C 1 -C 6 )alkyl, phenyl, phenyl-(C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl or (C 3 -C 6 )cycloalkyl-(C 1 -C 6 )alkyl, each of the 5 last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfo, cyano, thiocyanato, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 9 )cycloalkyl, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulfonyl, (C 1 -C 4 )haloalkylsulfonyl and in the case of cyclic radicals also (C 1 -C 4 )alkyl and (C 1 -C 4 )haloalkyl,    (X) n  is n substituents X, where the X independently of one another are halogen, hydroxyl, amino, nitro, formyl, carboxyl, cyano, thiocyanato, aminocarbonyl or (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkynyl, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, mono(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, N—(C 1 -C 6 )alkanoylamino or N—(C 1 -C 4 )alkanoyl-N—(C 1 -C 4 )alkylamino,     each of the last-mentioned 13 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, cyano, thiocyanato, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkylamino, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio and heterocyclylamino,     each of the last-mentioned 8 radicals being unsubstituted or having one or more substituents selected from the group consisting of halogen, nitro, cyano, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )haloalkoxy, formyl, (C 1 -C 4 )alkylcarbonyl and (C 1 -C 4 )alkoxycarbonyl,    or (C 3 -C 9 )cycloalkyl, phenyl, phenoxy, phenylthio, phenylcarbonyl, heterocyclyl, heterocyclyloxy, heterocyclylthio or heterocyclylamino,     each of the last-mentioned 9 radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, cyano, thiocyanato, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 6 )cycloalkyl, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylaminocarbonyl and di(C 1 -C 4 )alkylaminocarbonyl,    or two adjacent radicals X together are a fused cycle which has 4 to 6 ring atoms and is carbocyclic or contains hetero ring atoms selected from the group consisting of O, S and N and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )alkyl and oxo, and    n is 0, 1, 2 or 3.    
     
     
         5 . A compound of the formula (I) or a salt thereof as claimed in  claim 1 , wherein 
 R 2  is (C 3 -C 9 )cycloalkyl which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, thiocyanato, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, (C 1 -C 4 )alkylidene, mono(C 1 -C 4 )alkylamino and di(C 1 -C 4 )alkylamino,     or     heterocyclyl or phenyl, each of the last-mentioned two radicals being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, amino, nitro, formyl, carboxyl, sulfonyl, cyano, thiocyanato, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, (C 1 -C 4 )alkylthio, (C 1 -C 4 )haloalkylthio, mono(C 1 -C 4 )alkylamino, di(C 1 -C 4 )alkylamino, (C 3 -C 6 )cycloalkyl, heterocyclyl having 3 to 6 ring atoms, [(C 1 -C 4 )alkyl]carbonyl, [(C 1 -C 4 )alkoxy]carbonyl, aminocarbonyl, mono(C 1 -C 4 )alkylaminocarbonyl, di(C 1 -C 4 )alkylaminocarbonyl, (C 1 -C 4 )alkylsulfonyl and (C 1 -C 4 )haloalkylsulfonyl.    
     
     
         6 . A compound of the formula (I) or a salt thereof as claimed in  claim 1 , wherein 
 A 1  is a radical of the formula —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 — or —CH 2 CH 2 CH 2 CH 2 CH 2 — and    A 2  is a direct bond or a group of the formula     —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 —O—CH 2 —, —CH 2 —O—CH 2 —CH 2 —, —CH 2 —CH 2 —O—CH 2 —, —CH 2 —S—CH 2 —, —CH 2 —S—CH 2 —CH 2 —, —CH 2 —CH 2 —S—CH 2 —, —CH 2 —NH—CH 2 —, —CH 2 —NH—CH 2 —CH 2 —, —CH 2 —CH 2 —NH—CH 2 —, —CH 2 —N(CH 3 )—CH 2 —, —CH 2 —N(CH 3 )—CH 2 —CH 2 — or —CH 2 —CH 2 —N(CH 3 )—CH 2      and the number of the carbon atoms of the total of the numbers of the carbon atoms of the two radicals A 1  and A 2 —R 2      a) is 6 to 20 carbon atoms or    b) is 5 carbon atoms, in which case A 1 =a group of the formula —CH 2 — or —CH 2 CH 2 — and R 1 ═(C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl or (C 3 -C 6 )cycloalkyl.    
     
     
         7 . A process for the preparation of a compound of the formula (I) or a salt thereof as claimed in  claim 1 , which comprises 
 a) reacting a compound of the formula (II)    R 1 —Fu  (II)    where Fu is a functional group selected from the group consisting of carboxylic ester, carboxylic orthoester, carboxylic acid chloride, carboxamide, carboxylic anhydride and trichloromethyl with a biguanidide of the formula (III) or an acid addition salt thereof                          or    b) reacting a compound of the formula (IV)                          where Z 1  is an exchangeable radical or leaving group with a suitable amine of the formula (V) or an acid addition salt thereof                          where, in the formulae (II), (III), (IV) and (V), the radicals R 1 , R 2 , R 3 , R 4 , A 1 , A 2  and X and n are as defined in formula (I).    
     
     
         8 . A herbicidal or plant-growth-regulating composition, which comprises one or more compounds of the formula (I) or salts thereof as claimed in  claim 1  and formulation auxiliaries conventionally used in crop protection.  
     
     
         9 . A method of controlling harmful plants or of regulating the growth of plants, wherein an effective amount of one or more compounds of the formula (I) or salts thereof as claimed in  claim 1  is applied to the plants, the seeds of the plants or the area under cultivation.  
     
     
         10 . A method of controlling harmful plants or of regulating the growth of plants, wherein an effective amount of one or more compounds of the formula (I) or salts thereof as claimed in  claim 1  is used as herbicide or plant growth regulator.  
     
     
         11 . The method as claimed in  claim 10 , wherein the compounds of the formula (I) or the salts thereof are employed for controlling harmful plants or for regulating the growth in crops of useful plants or ornamentals.  
     
     
         12 . The method as claimed in  claim 11 , wherein the crop plants are transgenic crop plants.  
     
     
         13 . A compound of the formula (III) or (V) as defined in claim  7 .