Aminopropenoates as Fungicides

Abstract

This application claims priority to European Patent Application No. 09173304.8, filed Oct. 16, 2009, and the benefit of U.S. Provisional Application No. 61/253,091, filed Oct. 20, 2009, the disclosure of each of which is incorporated by reference herein in its entirety. The present invention relates to aminopropenoate derivatives, the process of their preparation, intermediate compounds, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants and in material protection, using these compounds or compositions.

1 . An aminopropenoate formula (I) 
       
         
           
           
               
               
           
         
         in which 
         R represents one of the following groups R A , R B  or R C   
       
       
         
           
           
               
               
           
         
         n represents 0, 1, 2, 3 or 4, 
         m represents 1, 2, 3 or 4, 
         t represents 0 or 1, 
         Y 1  represents S, O or NR 5 , 
         Y 2  represents O, S or NR 6 , 
         Y 3  represents S, O or NR 8 , 
         Y 4  represents a bond or O, S or NR 9 , 
         Y 5  represents SO or SO 2 , 
         in case that Y 2  represents NR 6 , then R 6  and R 1  together with the nitrogen atom to which they are linked may form a 5- to 7-membered, saturated or unsaturated, carbo- or heterocycle comprising up to 3 heteroatoms, which cycle may also include one of the groups C(═O) and C(═S), 
         in case that Y 4  represents NR 9 , then R 9  and R 7  together with the nitrogen atom to which they are linked may form a 5- to 7-membered, saturated or unsaturated, carbo- or heterocycle comprising up to 3 heteroatoms, which cycle may also include one of the groups C(═O) and C(═S), 
         R 1  represents hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkynyl-C 1 -C 8 -alkyl, C 1 -C 8 -halogeno-C 3 -C 8 -cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkyl, C 1 -C 8 -alkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -trialkylsilyl, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkyl, benzotriazolyl, aryl-C 3 -C 8 -cycloalkyl which can be substituted by up to 5 groups Q; 
         and, provided that when Y 2  does not represent NH, R 1  can also represent aryl which can be substituted by up to 5 groups Q, or aryl-C 1 -C 8 -alkyl which can be substituted by up to 5 groups Q; 
         Het represents one of the heterocycles Het 1 to Het 47 or Het 51 to Het 61: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         R 2  and R 3 , which can be the same or different, independently of one another represent hydrogen, halogen, CN, NH 2 , NO 2 , C 1 -C 8 -alkyl, C 1 -C 8 -hydroxyalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different, C 2 -C 8 -alkynyl, C 2 -C 8 -alkenyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkynyl-C 1 -C 8 -alkyl, C 3 -C 8 -halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy-C 2 -C 8 -alkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkynyl, C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkyl, C 1 -C 8 -alkylsulfinyl-C 1 -C 8 -alkyl, C 1 -C 8 -alkylsulfonyl-C 1 -C 8 -alkyl, amino-C 1 -C 8 -alkyl, C 1 -C 8 -alkylamino-C 1 -C 8 -alkyl, di-(C 1 -C 8 -alkyl)amino-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkyl, C 1 -C 8 -trialkylsilyl, phenyl which can be substituted by up to 5 groups Q, or phenyl-C 2 -C 4 -alkynyl, which can be substituted in the phenyl moiety by up to 5 groups Q, 
         R 2  and R 3  also together with the carbon atom to which they are linked can form a C 3 -C 7 -cycloalkyl, which may be substituted by 1 to 4 identical or different substituents selected from halogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio or phenyl, or can form a C 5 -C 10 -bicycloalkyl, a 2,3-dihydro-1H-indene-1-yl or a decahydronaphthalenyl, 
         R 4  represents aryl or a heterocycle E 1 to E 144: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         R 4  also represents hydrogen or halogen when n represents 1, 2, 3 or 4, 
         R 5  represents hydrogen, OH, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkynyl-C 1 -C 8 -alkyl, halogeno-C 3 -C 8 -cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 3 -C 8 -cyclo alkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkyl, C 1 -C 8 -alkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkyl, aryl which can be substituted by up to 5 groups Q, aryl-C 1 -C 8 -alkyl which can be substituted by up to 5 groups Q, or aryl-C 3 -C 8 -cycloalkyl which can be substituted by up to 5 groups Q; 
         R 6  represents hydrogen, OH, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkynyl-C 1 -C 8 -alkyl, halogeno-C 3 -C 8 -cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkyl, C 1 -C 8 -alkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkyl comprising, up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 3 -C 8 -cycloalkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkoxy, C 2 -C 8 -alkenyl-C 1 -C 8 -alkoxy, C 2 -C 8 -alkynyl-C 1 -C 8 -alkoxy, C 1 -C 8 -halogeno-C 3 -C 8 -cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkenyloxy, C 1 -C 8 -alkoxy-C 1 -C 8 -alkoxy, C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkoxy comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkoxy, C 1 -C 8 -alkylamino-C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkoxy comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylammo-C 1 -C 8 -alkoxy, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkoxy, aryloxy which can be substituted by up to 5 groups Q, benzyloxy which can be substituted by up to 5 groups Q, C 1 -C 8 -alkylamino, (C 1 -C 8 -alkyl)carbonylamino, C 3 -C 8 -cycloalkylamino, C 1 -C 8 -halogenoalkylamino comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkylamino, C 2 -C 8 -alkenyl-C 1 -C 8 -alkylamino, C 2 -C 8 -alkynyl-C 1 -C 8 -alkylamino, halogeno-C 3 -C 8 -cycloalkylamino comprising up to 9 halogen atoms which can be the same or different, arylamino which can be substituted by up to 5 groups Q, benzylamino which can be substituted by up to 5 groups Q, or aryl-C 3 -C 8 -cycloalkyl which can be substituted by up to 5 groups Q; 
         R 7  represents hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 2 -C 8 -alkenyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkynyl-C 1 -C 8 -alkyl, halogeno-C 3 -C 8 -cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkyl, C 1 -C 8 -alkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkyl, phenyl or naphthyl, each of which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q, or phenyl-C 1 -C 2 -alkylimino, 
         R 7  also represents CN, if R is R B , t is 0 and Y 4  is a bond, 
         R 8  represents hydrogen, OH, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkynyl-C 1 -C 8 -alkyl, C 1 -C 8 -halogeno-C 3 -C 8 -cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkyl, C 1 -C 8 -alkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkyl, phenyl which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q; C 1 -C 8 -alkoxy, C 3 -C 8 -cycloalkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkoxy, C 2 -C 8 -alkenyl-C 1 -C 8 -alkoxy, C 2 -C 8 -alkynyl-C 1 -C 8 -alkoxy, C 1 -C 8 -halogeno-C 3 -C 8 -cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkenyloxy, C 1 -C 8 -alkoxy-C 1 -C 8 -alkoxy, C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkoxy comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkoxy, C 1 -C 8 -alkylamino-C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkoxy comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylamino-C 1 -C 8 -alkoxy, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkoxy, aryloxy which can be substituted by up to 5 groups Q, or benzyloxy which can be substituted by up to 5 groups Q, 
         R 9  represents hydrogen, OH, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkynyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkynyl-C 1 -C 8 -alkyl, C 3 -C 8 -halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkyl, C 1 -C 8 -alkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkyl, phenyl which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q; C 1 -C 8 -alkoxy, C 3 -C 8 -cycloalkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkoxy, C 2 -C 8 -alkenyl-C 1 -C 8 -alkoxy, C 2 -C 8 -alkynyl-C 1 -C 8 -alkoxy, halogeno-C 3 -C 8 -cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkenyloxy, C 1 -C 8 -alkoxy-C 1 -C 8 -alkoxy, C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkoxy comprising up, to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkoxy, C 1 -C 8 -alkylamino-C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkoxy comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylamino-C 1 -C 8 -alkoxy, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkoxy, phenyloxy which can be substituted by up to 5 groups Q, or benzyloxy which can be substituted by up to 5 groups Q, 
         Q which can be the same or different, independently represents halogen, CN, NO 2 , C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkylsulfanyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, tri(C 1 -C 8 )alkylsilyl or tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl, or two vicinal substituents Q may be —OCH 2 O—, —OCF 2 O—, —O(CH 2 ) 2 O—, —O(CF 2 ) 2 O— or —N═CH—S—, 
         Z 1 , Z 2 , Z 3 , Z 4  Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10  and Z 11 , which can be the same or different, independently of one another represent hydrogen, halogen, NO 2 , CN, OH, SH, NH 2 , SF 5 , C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different and optionally in addition one hydroxy group, C 1 -C 8 -alkylamino, di-C 1 -C 8 -alkylamino, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -alkylsulfanyl, C 1 -C 8 -halogenoalkylsulfanyl comprising up to 9 halogen atoms which can be the same or different, C 2 -C 8 -alkenyl, C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different, C 2 -C 8 -alkynyl, C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different, C 2 -C 8 -alkenyloxy, C 2 -C 8 -halogenoalkenyloxy comprising up to 9 halogen atoms which can be the same or different, C 2 -C 8 -alkynyloxy, C 2 -C 8 -halogenoalkynyloxy comprising up to 9 halogen atoms which can be the same or different, C 2 -C 8 -alkenylsulfanyl, C 2 -C 8 -alkynylsulfanyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl, C 3 -C 7 -halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, formyl, formyloxy, formylamino, carbamoyl, N-hydroxycarbamoyl, (hydroxyimino)-C 1 -C 8 -alkyl, C 1 -C 8 -alkylcarbonyl, C 1 -C 8 -halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, (C 3 -C 7 -cycloalkyl)carbonyl, C 1 -C 8 -alkylcarbamoyl, di-C 1 -C 8 -alkylcarbamoyl, N—C 1 -C 8 -alkoxycarbamoyl, C 1 -C 8 -alkoxycarbamoyl, N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylaminocarbonyl, di-(C 1 -C 8 -alkyl)aminocarbonyl, C 1 -C 8 -alkylcarbonyloxy, C 1 -C 8 -halogenoalkylcarbonyloxy comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylcarbonylamino, C 1 -C 8 -halogenoalkylcarbonylamino comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylaminocarbonyloxy, di-(C 1 -C 8 -alkyl)amino carbonyl oxy, C 1 -C 8 -alkoxycarbonyloxy, C 1 -C 8 -alkylsulphinyl, C 1 -C 8 -halogenoalkylsulphinyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulphonyl, C 1 -C 8 -halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkoxyimino, (C 1 -C 8 -alkylimino)-C 1 -C 8 -alkyl, (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl, (C 1 -C 8 -alkenyloxyimino)-C 1 -C 8 -alkyl, (C 2 -C 8 -alkynyloxyimino)-C 1 -C 8 -alkyl, a (benzyloxyimino)-C 1 -C 8 -alkyl, tri-(C 1 -C 8 -alkyl)silyl, tri(C 1 -C 8 -alkyl)silyl-C 1 -C 8 -alkyl, benzyloxy which can be substituted by up to 5 groups Q, benzylsulfanyl which can be substituted by up to 5 groups Q, benzylamino which can be substituted by up to 5 groups Q, phenyl which can be substituted by up to 5 groups Q, naphthyl which can be substituted by up to 6 groups Q, phenoxy which can be substituted by up to 5 groups Q, phenylamino which can be substituted by up to 5 groups Q, phenylsulfanyl which can be substituted by up to 5 groups Q, or phenylmethylene which can be substituted by up to 5 groups Q, 
         or two vicinal substituents Z together with the consecutive carbon atoms to which they are linked form a 5- or 6-membered, saturated or unsaturated, carbo- or heterocycle comprising up to 3 heteroatoms, which can be substituted by up to four groups Q which can be the same or different and the other substituents Z as defined above, 
         or two geminal substituents Z together with the carbon atom to which they are linked can also be fused to represent C(≡O); C(═S), or C 3 -C 9 -cycloalkyl; 
         G 1  and G 2  which can be the same or different, independently of one another represent hydrogen, CN, OH, NH 2 , C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylamino, di-C 1 -C 8 -alkylamino, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms which can be the same or different, C 2 -C 8 -alkynyl, C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms which can be the same or different, C 2 -C 8 -alkenyloxy, C 2 -C 8 -halogenoalkenyloxy comprising up to 9 halogen atoms which can be the same or different, C 2 -C 8 -alkynyloxy, C 2 -C 8 -halogenoalkynyloxy comprising up to 9 halogen atoms which can be the same or different, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl, C 3 -C 7 -halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, formyl, carbamoyl, (hydroxyimino)-C 1 -C 8 -alkyl, C 1 -C 8 -alkylcarbonyl, C 1 -C 8 -halogenoalkylcarbonyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylcarbamoyl, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylamino carbonyl, di-C 1 -C 8 -alkylaminocarbonyl, C 1 -C 8 -alkylsulphonyl, C 1 -C 8 -halogenoalkylsulphonyl comprising up to 9 halogen atoms which can be the same or different, (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl, (C 1 -C 8 -alkenyloxyimino)-C 1 -C 8 -alkyl, (C 2 -C 8 -alkynyloxyimino)-C 1 -C 8 -alkyl, (benzyloxyimino)-C 1 -C 8 -alkyl, tri(C 1 -C 8 -alkyl)silyl, tri(C 1 -C 8 -alkyl)silyl-C 1 -C 8 -alkyl, benzyloxy which can be substituted by up to 5 groups Q, benzylamino which can be substituted by up to 5 groups Q, phenyl which can be substituted by up to 5 groups Q; naphthyl which can be substituted by up to 6 groups Q, phenoxy which can be substituted by up to 5 groups Q, phenylamino which can be substituted by up to 5 groups Q, or phenylmethylene which can be substituted by up to 5 groups Q, 
         provided that 
         when n represents 1 then R 2 , R 3  and R 4  do not represent simultaneously a hydrogen atom, 
         when Het represents Het 42, Y 1  and Y 2  represent O, R 1  represents ethyl, then Z 3  does not represent hydrogen or NO 2 , 
         when Het represents Het 8 and n represents 0, then R 4  does not represent an unsubstituted phenyl group, 
         when Het represents an indole ring then R B  does not represent —CH 2 —CH 2 —OH, —CH 2 —OCOC 2 H 5 , or —CH 2 —CH 2 —N(C 2 H 5 ) 2 , or 
         when Het represents a 4,5,6,7-tetrahydro-1H-indole then R A  does not represent —CH 2 —CH 2 —CH 2 —CH 3 , 
         or a salt, N-oxide, metallic complex, metalloidic complex or an optically active or geometric isomer thereof. 
       
     
     
         2 . A composition, comprising at least one aminopropenoate of the formula (I) according to  claim 1 , and one or more extenders, surfactant, or combinations thereof. 
     
     
         3 . (canceled) 
     
     
         4 . A method for controlling unwanted microorganisms, comprising applying at least one aminopropenoate of the formula (I) according to  claim 1  to the microorganisms, their habitat, or combinations thereof. 
     
     
         5 . A process for preparing a composition, comprising mixing at least one aminopropenoate of the formula (I) according to  claim 1  with one or more extenders, surfactants, or combinations thereof. 
     
     
         6 . A method for controlling unwanted microorganisms on a transgenic plant, comprising applying at least one aminopropenoate of the formula (I) according to  claim 1  to the transgenic plant, its seed, its habitat, or combinations thereof. 
     
     
         7 . The aminopropenoate of the formula (I) according to  claim 1 , wherein R represents R A . 
     
     
         8 . The aminopropenoate of the formula (I) according to  claim 1 , wherein R represents R B . 
     
     
         9 . The aminopropenoate of the formula (I) according to  claim 7 , wherein n represents 0, 1 or 2. 
     
     
         10 . The aminopropenoate of the formula (I) according to  claim 1 , wherein m represents 1 or 2. 
     
     
         11 . The aminopropenoate of the formula (I) according to  claim 1 , wherein Y 1  is S or O. 
     
     
         12 . The aminopropenoate of the formula (I) according to  claim 1 , wherein Y 2  represents O or NR 6  wherein R 6  represents hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkynyl-C 1 -C 8 -alkyl, C 1 -C 8 -halogeno-C 3 -C 8 -cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkyl, C 1 -C 8 -alkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkyl, or C 1 -C 8 -alkoxy. 
     
     
         13 . The aminopropenoate of the formula (I) according to  claim 1 , wherein Y 3  represents O or NR 8  wherein R 8  represents hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkynyl-C 1 -C 8 -alkyl, C 1 -C 8 -halogeno-C 3 -C 8 -cycloalkyl comprising up to 9 halogen atoms which can be the same or, different, C 3 -C 8 -cycloalkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkyl, C 1 -C 8 -alkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkoxy, C 1 -C 6 -halogenoalkoxy comprising, up to 9 halogen atoms which can be the same or different, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl-C 1 -C 6 -alkoxy, C 2 -C 6 -alkynyl-C 1 -C 6 -alkoxy, C 1 -C 6 -halogeno-C 3 -C 6 -cycloalkoxy comprising up to 9 halogen atoms which can be the same or different, C 3 -C 6 -cycloalkenyloxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkoxy-C 1 -C 6 -alkoxy comprising up to 9 halogen atoms which can be the same or different, C 1 -C 6 -alkylsulfanyl-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino-C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkylamino-C 1 -C 6 -alkoxy comprising up to 9 halogen atoms which can be the same or different, C 3 -C 6 -cycloalkylamino-C 1 -C 6 -alkoxy, C 1 -C 6 -trialkylsilyl-C 1 -C 6 -alkoxy, aryloxy which can be substituted by up to 5 groups Q, or benzyloxy which can be substituted by up to 5 groups Q. 
     
     
         14 . The aminopropenoate of the formula (I) according to  claim 1 , wherein Y 4  represents a bond, O or NR 9 , wherein R 9  represents hydrogen or C 1 -C 6 -alkyl. 
     
     
         15 . The aminopropenoate of the formula (I) according to  claim 1 , wherein R 1  represents hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl. 
     
     
         16 . The aminopropenoate of the formula (I) according to  claim 1 , wherein R 4  is selected from E 1 to E 48, E 52 to E 56, E 63, E 64, E 69 to E 77, E 98 to E 100, E 105, E 106, E 109 to E 112, E 129 or E 130, and wherein Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10  and Z 11 , which can be the same or different, independently of one another represent hydrogen, halogen, NO 2 , CN, OH, SH, NH 2 , methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, s-butyl, t-butyl, difluoromethyl, trifluoromethyl, fluoroethyl, difluoroethyl, methylamino, ethylamino, dimethylamino, diethylamino, methoxy, ethoxy, trifluoromethoxy, vinyl, allyl, ethinyl, propargyl, cyclopropyl, cyclohexyl, acetyl, C 1 -C 3 -halogenoalkylcarbonyl comprising up to 5 halogen atoms which can be the same or different, carboxyl, methoxycarbonyl, ethoxycarbonyl, C 1 -C 4 -alkylcarbonyloxy, C 1 -C 4 -alkylcarbonylamino, methylthio, ethylthio, trimethylsilyl, phenyl which can be substituted by up to 3 groups Q, or naphthyl which can be substituted by up to 6 groups Q, or two geminal substituents Z together with the carbon atom to which they are linked can be fused to represent C(═O). 
     
     
         17 . The aminopropenoate of the formula (I) according to  claim 1 , wherein R 5  represents hydrogen, OH, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 2 -halogenoalkyl comprising up to 5 halogen atoms which can be the same or different, C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl, C 2 -C 4 -alkenyl-C 1 -C 4 -alkyl, C 2 -C 4 -alkynyl-C 1 -C 4 -alkyl, halogeno-C 3 -C 6 -cycloalkyl comprising up to 9 halogen atoms which can be the same or different, cyclohexenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy-C 1 -C 4 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 4 -alkylsulfanyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylamino-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkylamino-C 1 -C 4 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 4 -trialkylsilyl-C 1 -C 4 -alkyl, phenyl or naphthyl, each of which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q. 
     
     
         18 . The aminopropenoate of the formula (I) according to  claim 1 , wherein R 2  and R 3 , which can be the same or different, independently of one another represent hydrogen, halogen, CN, NH 2 , C 1 -C 6 -alkyl, C 1 -C 6 -hydroxyalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 6 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -alkenyl-C 1 -C 6 -alkyl, C 2 -C 6 -alkynyl-C 1 -C 6 -alkyl, C 3 -C 6 -halogenocycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -halogenoalkoxy-C 1 -C 6 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 6 -alkylsulfanyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylamino-C 1 -C 6 -alkyl, C 1 -C 6 -halogenoalkylamino-C 1 -C 6 -alkyl comprising up to 9 halogen atoms which can be the same or different, or R 2  and R 3  together with the carbon atom to which they are linked can form a C 3 -C 7  cycloalkyl. 
     
     
         19 . An aminopropenoate of the formula (I) according to  claim 1 , wherein R 7  represents hydrogen, CN, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, halogeno-C 3 -C 6 -cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -halogenoalkoxy-C 1 -C 6 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 6 -alkylsulfanyl-C 1 -C 6 -alkyl, C 1 -C 6 -trialkylsilyl-C 1 -C 6 -alkyl, phenyl or naphthyl, each of which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q, or phenyl-C 1 -C 2 -alkylamino. 
     
     
         20 . The aminopropenoate of the formula (I) according to  claim 1 , wherein R represents R B , wherein t represents 0, Y 3  represents O, Y 4  represents NR 9 , and R 9  represents hydrogen, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl-C 1 -C 8 -alkyl, C 2 -C 8 -alkynyl-C 1 -C 8 -alkyl, C 1 -C 8 -halogeno-C 3 -C 8 -cycloalkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkoxy-C 1 -C 8 -alkyl comprising up to 9 halogen atoms, which can be the same or different, C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkyl, C 1 -C 8 -alkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkylamino-C 1 -C 8 -alkyl comprising up to 9 halogen atoms which can be the same or different, C 3 -C 8 -cycloalkylamino-C 1 -C 8 -alkyl, C 1 -C 8 -trialkylsilyl-C 1 -C 8 -alkyl, phenyl which can be substituted by up to 5 groups Q, benzyl which can be substituted by up to 5 groups Q. 
     
     
         21 . The aminopropenoate of the formula (I) according to  claim 1 , wherein Q which can be the same or different, independently represents halogen, CN, NO 2 , C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different, C 1 -C 6 -halogenoalkoxy comprising up to 9 halogen atoms which can be the same or different, tri(C 1 -C 6 )alkylsilyl or tri(C 1 -C 6 )alkylsilyl-C 1 -C 6 -alkyl.