Pyridinecarboxamides, useful-plant-protecting composition comprising them and processes for their prepartion and their use

Abstract

Compounds of the formula (I), or salts thereof, in which R 1 to R 4 are as defined in formula (I) of claim 1 are suitable as useful-plant-protecting agents for reducing or preventing harmful effects of agrochemicals on the useful plants and their method of preparation are described.

1 . A method for protecting useful plants against phytotoxic side effects of agrochemicals, which comprises applying an effective amount of one or more of the formula (I) or salts thereof, 
       
         
           
           
               
               
           
         
       
       in which 
       R 1  is a (C 1 -C 6 )-haloalkyl radical and 
       R 2  is hydrogen or halogen and 
       R 3  is hydrogen, (C 1 -C 16 )-alkyl, (C 2 -C 16 )-alkenyl or (C 2 -C 16 )-alkynyl,
 where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl, [(C 1 -C 4 )-haloalkoxy]-carbonyl, (C 3 -C 6 )-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, 
 
        or (C 3 -C 6 )-cycloalkyl, (C 4 -C 6 )-cycloalkenyl, (C 3 -C 6 )-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6 )-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
 where each of the 4 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (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 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl, [(C 1 -C 4 )-haloalkoxy]-carbonyl, (C 3 -C 6 )-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, 
 
        and 
       R 4  is (C 1 -C 16 )-alkyl, (C 2 -C 16 )-alkenyl or (C 2 -C 16 )-alkynyl,
 where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl, [(C 1 -C 4 )-haloalkoxy]-carbonyl, (C 3 -C 6 )-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, 
 
        or (C 3 -C 6 )-cycloalkyl, (C 4 -C 6 )-cycloalkenyl, (C 3 -C 6 )-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6 )-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
 where each of the 4 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (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 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl, [(C 1 -C 4 )-haloalkoxy]-carbonyl, (C 3 -C 6 )-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, 
 
        or 
       R 3  is (C 1 -C 4 )-alkoxy, (C 2 -C 4 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy or (C 2 -C 4 )-haloalkoxy 
        and 
       R 4  is hydrogen or (C 1 -C 4 )-alkyl 
        or 
       R 3  and R 4  together with the directly attached nitrogen atom are a four- to eight-membered heterocyclic ring which, in addition to the nitrogen atom, may also comprise further hetero ring atoms, and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy and (C 1 -C 4 )-alkylthio, 
        or 
       R 3  and R 4  together with the directly attached nitrogen atom are the group —N═CR 5-NR 6 R 7  in which 
        R 5  is hydrogen or (C 1 -C 6 )-alkyl, and 
        R 6 , R 7  independently of one another are hydrogen or (C 1 -C 4 )-alkyl, or 
        R 6  and R 7  together with the directly attached nitrogen atom form a five- to seven-membered heterocyclic ring, 
        or 
       R 1  is a (C 1 -C 6 )-haloalkyl radical, 
       R 2  is halogen, 
       R 3  is hydrogen and 
       R 4  is hydrogen 
        or 
       R 1  is a radical of the formula CF 2 C 1 , CF 2 H, CF 2 CF 3 , CF 2 CF 2 H, CF 2 CF 2 Cl, CFClCF 3 , CFHCF 3 , CF(CF 3 ) 2 , CH(CF 3 ) 2 , CF 2 CF 2 CF 3 , or C(CH 3 ) 2 F, 
       R 2  is hydrogen, 
       R 3  is hydrogen and 
       R 4  is hydrogen, 
       before, after or simultaneously with the agrochemicals to the plants, parts of the plants, the plant seeds or seed of the plants. 
     
     
         2 . The method as claimed in  claim 1  wherein 
       R 3  is hydrogen, (C 1 -C 10 )-alkyl, (C 2 -C 10 )-alkenyl or (C 2 -C 10 )-alkynyl,
 where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl, [(C 1 -C 4 )-haloalkoxy]-carbonyl, 
 (C 3 -C 6 )-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl, 
 phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy and (C 1 -C 4 )-alkylthio, and 
 heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (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 and oxo, 
 
        or (C 3 -C 6 )-cycloalkyl, (C 4 -C 6 )-cycloalkenyl, (C 3 -C 6 )-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6 )-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
 where each of the 4 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (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 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl, [(C 1 -C 4 )-haloalkoxy]-carbonyl, 
 (C 3 -C 6 )-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl, 
 phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy and (C 1 -C 4 )-alkylthio, and 
 heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (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 and oxo, 
 
       and 
       R 4  is (C 1 -C 10 )-alkyl, (C 2 -C 10 )-alkenyl or (C 2 -C 10 )-alkynyl,
 where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl, [(C 1 -C 4 )-haloalkoxy]-carbonyl, 
 (C 3 -C 6 )-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl, 
 phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy and (C 1 -C 4 )-alkylthio, and 
 heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (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 and oxo, 
 
        or (C 3 -C 6 )-cycloalkyl, (C 4 -C 6 )-cycloalkenyl, (C 3 -C 6 )-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6 )-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
 where each of the 4 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (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 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl, [(C 1 -C 4 )-haloalkoxy]-carbonyl, 
 (C 3 -C 6 )-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl, 
 phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy and (C 1 -C 4 )-alkylthio, and 
 heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (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 and oxo. 
 
     
     
         3 . The method as claimed in  claim 1  wherein 
       R 3  is hydrogen, (C 1 -C 10 )-alkyl, (C 2 -C 10 )-alkenyl or (C 2 -C 10 )-alkynyl,
 where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl, [(C 1 -C 4 )-haloalkoxy]-carbonyl, 
 (C 3 -C 6 )-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl, 
 phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy and (C 1 -C 4 )-alkylthio, and 
 heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (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 and oxo, 
 
        or (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
 where each of the 2 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C 1 -C 4 )-alkyl, 
 
       and 
       R 4  is (C 1 -C 10 )-alkyl, (C 2 -C 10 )-alkenyl or (C 2 -C 10 )-alkynyl,
 where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl, [(C 1 -C 4 )-haloalkoxy]-carbonyl, 
 (C 3 -C 6 )-cycloalkyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-haloalkyl, 
 phenyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy and (C 1 -C 4 )-alkylthio, and 
 heterocyclyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (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 and oxo, 
 
        or (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
 where each of the 2 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C 1 -C 4 )-alkyl. 
 
     
     
         4 . The method as claimed in  claim 1  wherein 
       R 3  is hydrogen, (C 1 -C 10 )-alkyl, (C 2 -C 10 )-alkenyl or (C 2 -C 10 )-alkynyl,
 where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio and [(C 1 -C 4 )-alkoxy]-carbonyl, 
 
       and 
       R 4  is (C 1 -C 10 )-alkyl, (C 2 -C 10 )-alkenyl or (C 2 -C 10 )-alkynyl,
 where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio and [(C 1 -C 4 )-alkoxy]-carbonyl. 
 
     
     
         5 . The method as claimed in  claim 1 , wherein 
       R 1  is CF 3 , CF 2 C 1 , CF 2 H, CF 2 CF 3 , CF 2 CF 2 H, CF 2 CF 2 C 1 , CF 2 CF 2 CF 3  or C(CH 3 ) 2 F and 
       R 2  is hydrogen or halogen. 
     
     
         6 . The method as claimed in  claim 1 , wherein 
       R 1  is a (C 1 -C 6 )-haloalkyl radical, 
       R 2  is halogen, 
       R 3  is hydrogen, and 
       R 4  is hydrogen. 
     
     
         7 . The method as claimed in  claim 1 , wherein 
       R 1  is a radical of the formula CF 2 C 1 , CF 2 H, CF 2 CF 3 , CF 2 CF 2 H, CF 2 CF 2 Cl, CFClCF 3 , CFHCF 3 , CF(CF 3 ) 2 , CH(CF 3 ) 2 , CF 2 CF 2 CF 3 , or C(CH 3 ) 2 F, 
       R 2  is hydrogen, 
       R 3  is hydrogen and 
       R 4  is hydrogen. 
     
     
         8 . The method as claimed in any of  claim 1 , wherein
 one or more compounds of the formula (I) or salts thereof are used together with one or more agrochemicals which, applied on their own, cause damage to the useful plants, optionally in the presence of formulation auxiliaries.   
     
     
         9 . The method as claimed in  claim 1 , wherein the application is by the post-emergence method. 
     
     
         10 . The method as claimed in  claim 1 , wherein the application of the compound of the formula (I) or a salt thereof is by treating the plant seeds or seed of the plants. 
     
     
         11 . The method as claimed in  claim 1 , wherein the application is by the pre-emergence method. 
     
     
         12 . A method for the selective control of harmful plants in crops of useful plants, which comprises applying an effective amount of one or more compounds of the formula (I) or salts thereof as defined in  claim 1  before, after or simultaneously with one or more herbicides to the plants, parts of plants, plant seeds or seed of the plants. 
     
     
         13 . The method as claimed in  claim 12 , which comprises treating the seed of the plants with one or more compounds of the formula (I) or salts thereof and applying the herbicide after sowing by the pre-emergence method or by the post-emergence method. 
     
     
         14 . A compound of the formula (I) or a salt thereof, 
       
         
           
           
               
               
           
         
       
       in which 
       R 1  is a (C 1 -C 6 )-haloalkyl radical and 
       R 2  is hydrogen or halogen and 
       R 3  is hydrogen, (C 1 -C 16 )-alkyl, (C 2 -C 16 )-alkenyl or (C 2 -C 16 )-alkynyl,
 where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl and [(C 1 -C 4 )-haloalkoxy]-carbonyl 
 
        or (C 3 -C 6 )-cycloalkyl, (C 4 -C 6 )-cycloalkenyl, (C 3 -C 6 )-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6 )-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
 where each of the 4 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (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 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl, [(C 1 -C 4 )-haloalkoxy]-carbonyl, (C 3 -C 6 )-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, 
 
        and 
       R 4  is (C 1 -C 16 )-alkyl, (C 2 -C 16 )-alkenyl or (C 2 -C 16 )-alkynyl,
 where each of the 3 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy, (C 1 -C 4 )-alkylthio, (C 1 -C 4 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl and [(C 1 -C 4 )-haloalkoxy]-carbonyl, 
 
        or (C 3 -C 6 )-cycloalkyl, (C 4 -C 6 )-cycloalkenyl, (C 3 -C 6 )-cycloalkyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C 4 -C 6 )-cycloalkenyl which is condensed at one side of the ring to a 4- to 6-membered saturated or unsaturated carbocyclic ring,
 where each of the 4 last mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, hydroxyl, cyano, (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 )-alkylamino, di[(C 1 -C 4 )-alkyl]-amino, [(C 1 -C 4 )-alkoxy]-carbonyl, [(C 1 -C 4 )-haloalkoxy]-carbonyl, (C 3 -C 6 )-cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, 
 
        or 
       R 3  is (C 1 -C 4 )-alkoxy, (C 2 -C 4 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy or (C 2 -C 4 )-haloalkoxy and 
       R 4  is hydrogen or (C 1 -C 4 )-alkyl 
        or 
       R 3  and R 4  together with the directly attached nitrogen atom are a four- to eight-membered heterocyclic ring which, in addition to the nitrogen atom, may also comprise further hetero ring atoms, and which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, cyano, nitro, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-haloalkoxy and (C 1 -C 4 )-alkylthio, 
        or 
       R 3  and R 4  together with the directly attached nitrogen atom are the group —N═CR 5 —NR 6 R 7  in which 
        R 5  is hydrogen or (C 1 -C 6 )-alkyl, and 
        R 6 , R 7  independently of one another are hydrogen or (C 1 -C 4 )-alkyl, or 
        R 6  and R 7  together with the directly attached nitrogen atom form a five- to seven-membered heterocyclic ring, 
        or 
       R 1  is a (C 1 -C 6 )-haloalkyl radical, 
       R 2  is halogen, 
       R 3  is hydrogen and 
       R 4  is hydrogen 
        or 
       R 1  is a radical of the formula CF 2 CF 3 , CF 2 CF 2 H, CF 2 CF 2 Cl, CFClCF 3 , CFHCF 3 , CF(CF 3 ) 2 , CH(CF 3 ) 2 , CF 2 CF 2 CF 3 , or C(CH 3 ) 2 F, 
       R 2  is hydrogen, 
       R 3  is hydrogen and 
       R 4  is hydrogen. 
     
     
         15 . A process for preparing compounds of the general formula (I) or salts thereof as defined in  claim 14 , which comprises 
       (a) reacting a carboxylic acid of the general formula (II) 
       
         
           
           
               
               
           
         
         in which R 1  and R 2  are as defined for the compound of the formula (I) to be prepared, 
         with an amine of the formula (III) or a salt thereof, 
       
       
         
           
           
               
               
           
         
         in which R 3  and R 4  are as defined for the compound of the formula (I) to be prepared, 
         to give the compound of the formula (I) or 
       
       (b) reacting a carboxylic ester of the general formula (IV) 
       
         
           
           
               
               
           
         
         in which R 1  and R 2  are as defined for the compound of the formula (I) to be prepared and “Alkyl” is an alkyl radical, with an amine of the formula (III) or a salt thereof, 
       
       
         
           
           
               
               
           
         
         in which R 3  and R 4  are as defined for the compound of the formula (I) to be prepared, to give the compound of the formula (I) or 
       
       (c) reacting a carbonyl halide or a carboxylic anhydride of the general formula (V), 
       
         
           
           
               
               
           
         
         in which R 1  and R 2  are as defined for the compound of the formula (I) to be prepared and Hal is a halogen atom or an acyloxy radical with an amine of the formula (III) or a salt thereof, 
       
       
         
           
           
               
               
           
         
         in which R 3  and R 4  are as defined for the compound of the formula (I) to be prepared to give the compound of the formula (I), or 
       
       (d) if R 3  and R 4  in the compound of the formula (I) to be prepared are each hydrogen,
 reacting a compound of the formula (VI), 
 
       
         
           
           
               
               
           
         
         in which R 1  is as defined for the compound of the formula (I) to be prepared, and “Alkyl” is an alkyl radical, 
         with malonamide to give the compound of the formula (I). 
       
     
     
         15 . A crop protection composition which comprises one or more compounds of the formula (I) or salts thereof as defined in  claim 1  and formulation auxiliaries. 
     
     
         16 . A crop protection composition which comprises one or more compounds of the formula (I) or salts thereof as defined in  claim 1  and one or more agrochemicals and, optionally, formulation auxiliaries.