Patent Publication Number: US-2013231303-A1

Title: 5-halogenopyrazole(thio)carboxamides

Description:
The present invention relates to novel 5-halogenopyrazole(thio)carboxamides, their process of preparation, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions. 
     It is already known that numerous carboxamides have fungicidal properties (cf., for example, WO-A 1998/03495, WO-A 1998/03486 and EP-A 0 589 313). Thus, 1-methyl-3-trifluoromethyl-5-fluoro- and 1,3-dimethylfluoropyrazolecarboxamides are already known (WO-A 2006/061215, WO-A 2005/042494, WO-A 2005/042493, WO-A 2008/095890, WO-A 2004/035589, WO-A 2003/074491). 
     The activity of these compounds is good; however, in some cases, for example at low application rates, it is sometimes unsatisfactory. 
     This invention now provides novel 1-methyl-3-dihalogenomethyl-5-halogenopyrazole(thio)carboxamides of the formula (I) 
     
       
         
         
             
             
         
       
         
         in which T represents an oxygen or sulfur atom 
         R represents hydrogen, C 1 -C 6 -alkylsulfonyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl-sulfonyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl or formyl; 
         Hal1 and Hal2 independently of one another represent chlorine or fluorine; 
         Q represents Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , or Q 6 ; 
         L represents 
       
    
     
       
         
         
             
             
         
       
         
         where the bond marked by * is attached to the amide while the bond marked # is attached to Q; 
         R 1  represents hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; 
         Q 1  represents 
       
    
     
       
         
         
             
             
         
       
         
         where the bond marked # is attached to L; 
         R 2  represents hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl or optionally substituted phenyl; 
         Z 1  represents —CR 3 R 4 R 5  or —SiR 3 R 4 R 5 ; 
         s represents 0, 1, 2 or 3; 
         t represents 0 or 1; 
         R 3  represent hydrogen, cyano, C 1 -C 8 -alkyl, or C 1 -C 6 -haloalkyl; 
         R 4 , R 5  independently of one another represents hydrogen, C 1 -C 8 -alkyl, or C 1 -C 6 -haloalkyl; or 
         R 3  and R 4  together with the carbon atom to which they are attached form a 3- to 6-membered optionally substituted carbocyclic or heterocyclic saturated or unsaturated ring; 
         Q 2  represents 
       
    
     
       
         
         
             
             
         
       
         
         where the bond marked # is attached to L; 
         R 6  represents hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl or optionally substituted phenyl; 
         R 7  represents hydrogen, C 1 -C 4 -alkyl, or C 1 -C 4 -haloalkyl; 
         Z 2  represents hydrogen, —CR 8 R 9 R 10  or —SiR 8 R 9 R 10 ; 
         u represents 0, 1 or 2; 
         R 8  represent hydrogen, cyano, C 1 -C 8 -alkyl, or C 1 -C 6 -haloalkyl; or 
         R 7  and R 8  together with the carbon atoms to which they are attached form a 3- to 6-membered optionally substituted carbocyclic saturated or unsaturated ring; 
         R 9 , R 10  independently of one another represents hydrogen, C 1 -C 8 -alkyl, or C 1 -C 6 -haloalkyl; or 
         R 8  and R 9  together with the carbon atom to which they are attached form a 3- to 6-membered optionally substituted carbocyclic saturated or unsaturated ring; 
         Q 3  represents 
       
    
     
       
         
         
             
             
         
       
         
         where the bond marked # is attached to L; 
         R 11  represents hydrogen or halogen; 
         R 12  represents hydrogen or halogen; 
         R 13  represents optionally substituted C 2 -C 12 -alkyl, optionally substituted C 2 -C 12 -alkenyl, optionally substituted C 2 -C 12 -alkynyl, optionally substituted C 3 -C 12 -cycloalkyl, optionally substituted phenyl or heterocyclyl; 
         Q 4  represents 
       
    
     
       
         
         
             
             
         
       
         
         where the bond marked # is attached to L, 
         R 14 , R 15  and R 16  independently of one another represent halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -alkylsulfonyl, C 3 -C 6 -cycloalkyl, or represent C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylsulfanyl or C 1 -C 4 -halo-alkylsulfonyl having in each case 1 to 5 halogen atoms; 
         Q 5  represents 
       
    
     
       
         
         
             
             
         
       
         
         where the bond marked # is attached to L; 
         Q 6  represents 
       
    
     
       
         
         
             
             
         
       
         
         where R 17  represents hydrogen or fluorine; 
         where, unless indicated otherwise, a group or a substituent which is substituted according to the invention is substituted by one or more group selected in the list consisting of halogen; nitro, cyano, C 1 -C 12 -alkyl; C 1 -C 6 -haloalkyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkoxy; C 1 -C 6 -haloalkoxy having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfanyl; C 1 -C 6 -haloalkylsulfanyl having 1 to 9 identical or different halogen atoms; C 1 -C 6 -alkylsulfonyl; C 1 -C 6 -haloalkylsulfonyl having 1 to 9 identical or different halogen atoms; C 2 -C 12 -alkenyl; C 2 -C 12 -alkynyl; C 3 -C 7 -cycloalkyl; phenyl; tri(C 1 -C 8 )alkylsilyl; tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl; 
       
    
     The formula (I) provides a general definition of the 1-methyl-3-dihalogeno-5-halogenopyrazole(thio)carboxamides according to the invention. Preferred radical definitions for the formulae shown above and below are given below. These definitions apply to the end products of the formula (I) and likewise to all intermediates.
     T preferably represents an oxygen atom   R preferably represents hydrogen, C 1 -C 4 -alkylsulfonyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -haloalkylsulfonyl, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl having in each case 1 to 9 fluorine, chlorine and/or bromine atoms; or formyl.   R particularly preferably represents hydrogen, methylsulfonyl, ethylsulfonyl, n- or isopropyl-sulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, trifluoromethylsulfonyl, trifluoromethoxymethyl; or formyl.   R very particularly preferably represents hydrogen, methoxymethyl, or formyl.   Hal1 preferably represents chlorine.   Hal1 preferably represents fluorine.   Hal2 preferably represents chlorine.   Hal2 preferably represents fluorine.   L moreover preferably represents L-1   L moreover preferably represents L-2   L moreover preferably represents L-3.   R 1  preferably represents hydrogen or chlorine   Z 1  preferably represents —CR 3 R 4 R 5 .   Z 1  moreover preferably represents —SiR 3 R 4 R 5 .   s preferably represents 0.   s preferably represents 1.   s moreover preferably represents 2.   s particularly preferably represents 1.   t preferably represents 0.   t preferably represents 1.   R 2  preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, n- or isopropyl, or represents methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine   R 2  particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl, chloromethyl, chlorofluoromethyl, fluorodichloromethyl, difluorochloromethyl, pentafluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2-chloro-2,2-difluoroethyl, 2-dichloro-2-fluoroethyl, 2,2,2-tri-chloroethyl, 1-chlorobutyl, heptafluoro-n-propyl or heptafluoroisopropyl.   R 2  very particularly preferably represents hydrogen, methyl or ethyl.   R 2  especially preferably represents hydrogen or methyl.   R 3  preferably represents fluorine, chlorine, bromine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl or represents methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine   R 3  particularly preferably represents fluorine, chlorine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl, chloromethyl, chlorofluoromethyl, fluorodichloromethyl, difluorochloro-methyl, pentafluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2-chloro-2,2-difluoroethyl, 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, 1-chlorobutyl, heptafluoro-n-propyl or heptafluoroisopropyl.   R 3  very particularly preferably represents chlorine, methyl, ethyl, isopropyl or trifluoromethyl.   R 4  preferably represents fluorine, chlorine, bromine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl or represents methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine   R 4  particularly preferably represents fluorine, chlorine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl, chloromethyl, chlorofluoromethyl, fluorodichloromethyl, difluorochloro-methyl, pentafluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2-chloro-2,2-difluoroethyl, 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, 1-chlorobutyl, heptafluoro-n-propyl or heptafluoroisopropyl.   R 4  very particularly preferably represents chlorine, methyl, ethyl, isopropyl or trifluoromethyl.   

     In a particular embodiment, R 3  and R 4  together with the carbon atom to which they are attached preferably form a 3- to 6-membered carbocyclic or heterocyclic saturated or unsaturated ring which is optionally substituted by halogen, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,
     R 3  and R 4  together with the carbon atom to which they are attached particularly preferably form a 3-, 5- or 6-membered carbocyclic saturated ring which is optionally substituted by methyl, ethyl or trifluoromethyl,   R 3  and R 4  moreover together with the carbon atom to which they are attached very particularly preferably form a 6-membered carbocyclic unsaturated ring which is optionally substituted by halogen, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy.   R 5  preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl or represents methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine   R 5  particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, n- or isopropyl, iso-, sec- or tert-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl, chloromethyl, chlorofluoromethyl, fluorodichloromethyl, difluorochloro-methyl, pentafluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2-chloro-2,2-difluoroethyl, 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, 1-chlorobutyl, heptafluoro-n-propyl or heptafluoroisopropyl.   R 5  very particularly preferably represents hydrogen, chlorine, methyl, ethyl, isopropyl or trifluoromethyl.   Z 2  preferably represents —CR 8 R 9 R 10 .   Z 2  moreover preferably represents —SiR 8 R 8 R 10 .   u preferably represents 0.   u preferably represents 1.   u particularly preferably represents 1.   R 6  preferably represents hydrogen, methyl or ethyl.   R 7  preferably represents hydrogen, methyl or ethyl.   R 8  preferably represents fluorine, chlorine, bromine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl or represents methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine   R 8  particularly preferably represents fluorine, chlorine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl, chloromethyl, chlorofluoromethyl, fluorodichloromethyl, difluorochloro-methyl, pentafluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2-chloro-2,2-difluoroethyl, 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, 1-chlorobutyl, heptafluoro-n-propyl or heptafluoroisopropyl.   R 8  very particularly preferably represents chlorine, methyl, ethyl, isopropyl or trifluoromethyl.   R 9  preferably represents fluorine, chlorine, bromine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl or represents methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine   R 9  particularly preferably represents fluorine, chlorine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl, chloromethyl, chlorofluoromethyl, fluorodichloromethyl, difluorochloro-methyl, pentafluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2-chloro-2,2-difluoroethyl, 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, 1-chlorobutyl, heptafluoro-n-propyl or heptafluoroisopropyl.   R 9  very particularly preferably represents chlorine, methyl, ethyl, isopropyl or trifluoromethyl.   

     In a particular embodiment, R 8  and R 9  together with the carbon atom to which they are attached preferably form a 3- to 6-membered carbocyclic or heterocyclic saturated or unsaturated ring which is optionally substituted by halogen, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,
     R 8  and R 9  moreover together with the carbon atom to which they are attached particularly preferably form a 3-, 5- or 6-membered carbocyclic saturated ring which is optionally substituted by methyl, ethyl or trifluoromethyl,   R 8  and R 9  moreover together with the carbon atom to which they are attached very particularly preferably form a 6-membered carbocyclic unsaturated ring which is optionally substituted by halogen, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy.   R 10  preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl or represents methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, each of which is mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine and bromine   R 10  particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, n- or isopropyl, iso-, sec- or tert-butyl, trifluoromethyl, difluoromethyl, fluoromethyl, trichloromethyl, dichloromethyl, chloromethyl, chlorofluoromethyl, fluorodichloromethyl, difluorochloro-methyl, pentafluoroethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2-chloro-2,2-difluoroethyl, 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, 1-chlorobutyl, heptafluoro-n-propyl or heptafluoroisopropyl.   R 10  very particularly preferably represents hydrogen, chlorine, methyl, ethyl, isopropyl or trifluoromethyl.   R 11  and R 12  independently of one another preferably represent hydrogen, fluorine, chlorine or bromine;   R 11  and R 12  independently of one another particularly preferably represent hydrogen or fluorine;   R 11  and R 12  very particularly preferably represent hydrogen;   R 13  preferably represents C 2 -C 6 -alkyl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted phenyl, pyridyl, thienyl or furyl;   R 13  particularly preferably represents ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, isopentyl, n-hexyl, isohexyl, n-heptyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, a-methylcyclopropyl, 2-, 3- or 4-halo-substituted phenyl, 2-thienyl, 3-thienyl or 2-furyl;   R 13  very particularly preferably represents ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, a-methylcyclopropyl, 4-fluorophenyl, 4-bromophenyl, 4-chlorophenyl, 2-thienyl, 3-thienyl or 2-furyl;   R 14 , R 15  and R 16  independently of one another preferably represent fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or isopropyl, n-, s- or t-butyl, methoxy, ethoxy, methylsulfanyl, ethylsulfanyl, n- or isopropylsulfanyl, cyclopropyl, trifluoromethyl, trichloromethyl, trifluoro-ethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluor-omethylsulfanyl, difluorochloromethylsulfanyl or trifluoromethylsulfanyl;   R 14 , R 5  and R 16  independently of one another particularly preferably represent fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy;   R 14 , R 15  and R 16  independently of one another very particularly preferably represent fluorine, chlorine, bromine or trifluoromethyl.   

     Preference is given to compounds of the formula (I) in which all radicals in each case have the preferred meanings mentioned above. 
     Particular preference is given to compounds of the formula (I) in which all radicals in each case have the particularly preferred meanings mentioned above. 
     Very particular preference is given to compounds of the formula (I) in which all radicals in each case have the very particularly preferred meanings mentioned above. 
     The following groups of novel (thio)carboxamides of the formula 
     
       
         
         
             
             
         
       
         
         in which T, R, L, Q 1  have the meanings given above and Hal represents fluorine or chlorine; 
       
    
     
       
         
         
             
             
         
       
         
         in which T, R, L, Q 2  have the meanings given above and Hal represents fluorine or chlorine; 
       
    
     
       
         
         
             
             
         
       
         
         in which T, R, L, Q 3  have the meanings given above and Hal represents fluorine or chlorine; 
       
    
     
       
         
         
             
             
         
       
         
         in which T, R, L, Q 4  have the meanings given above and Hal represents fluorine or chlorine; 
       
    
     
       
         
         
             
             
         
       
         
         in which T, R, L, Q 5  have the meanings given above and Hal represents fluorine or chlorine; 
       
    
     
       
         
         
             
             
         
       
         
         in which T, R, L, Q 6  have the meanings given above and Hal represents fluorine or chlorine;
 
are preferred and in each case to be understood as a subset of the compounds of the formula (I) mentioned above.
 
       
    
     The following groups of novel carboxamides of the formulae 
     
       
         
         
             
             
         
       
         
         in which T, R, L and Q have the meanings given above and Hal represents fluorine; 
       
    
     
       
         
         
             
             
         
       
         
         in which T, R, L and Q have the meanings given above and Hal represents chlorine;
 
are preferred and in each case to be understood as a subset of the compounds of the formula (I) mentioned above.
 
       
    
     Very particular special preference is given to compounds of the formula (I) where
     T represents oxygen   R represents hydrogen;   Hal represents chlorine or fluorine;   Hal1 and Hal2 independently of one another represent chlorine or fluorine;   Q represents Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , or Q 6 ;   

     
       
         
         
             
             
         
       
         
         L represents, 
         where the bond marked * is attached to the amide while the bond marked # is attached to Q; 
         R 1  represents hydrogen; 
         Q 1  represents 
       
    
     
       
         
         
             
             
         
       
         
         where the bond marked # is attached to L, 
         R 2  represents hydrogen, methyl or ethyl, 
         Z 1  represents —CR 3 R 4 R 5  or —SiR 3 R 4 R 5 ; 
         s represents 0, 1, 2 or 3; 
         t represents 0, 
         R 3 , R 4 , R 5  independently of one another represent hydrogen or methyl; 
         Q 2  represents 
       
    
     
       
         
         
             
             
         
       
         
         where the bond marked # is attached to L, 
         R 6  represents hydrogen or methyl, 
         R 7  represents hydrogen or methyl, 
         Z 2  represents —CR 8 R 9 R 10  or —SiR 8 R 9 R 10 ; 
         u represents 0, 1 or 2; 
         R 8 , R 9 , R 10  independently of one another represent hydrogen or methyl; 
         Q 3  represents 
       
    
     
       
         
         
             
             
         
       
         
         where the bond marked # is attached to L; 
         R 11  and R 12  represent hydrogen; 
         R 13  represents cyclopropyl; 
         Q 4  represents 
       
    
     
       
         
         
             
             
         
       
         
         where the bond marked # is attached to L; 
         R 14 , R 15  and R 16  independently of one another represent fluorine, chlorine, bromine or trifluoromethyl; 
         Q 5  represents 
       
    
     
       
         
         
             
             
         
       
         
         Q 6  represents 
       
    
     
       
         
         
             
             
         
       
     
     Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, can in each case be straight-chain or branched as far as this is possible, including in combination with heteroatoms, such as, for example, in alkoxy. 
     Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution the substituents can be identical or different. Thus, the definition dialkylamino also includes an amino group which is unsymmetrically substituted by alkyl, such as, for example, methylethylamino. 
     Halogen-substituted radicals, such as, for example, halogenoalkyl, are mono- or polyhalogenated. In the case of polyhalogenation, the halogen atoms can be identical or different. Halogen denotes fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine. 
     The compounds according to the invention may, if appropriate, be present as mixtures of various possible isomeric forms, in particular stereoisomers such as, for example, E and Z, threo and erythro, and also optical isomers, and, if appropriate, also of tautomers. What is claimed are both the E and the Z isomers, and also the threo and erythro, and also the optical isomers, any mixtures of these isomers, and also the possible tautomeric forms. 
     In the variations according to the invention of Q, up to two stereocentres (*) are present. What is claimed are all diastereomers and enantiomers, in particular of the following radicals: 
     
       
         
         
             
             
         
       
     
     The abovementioned general or preferred radical definitions or illustrations can be combined as desired between the respective ranges and preferred ranges. They apply both to the end products and, correspondingly, to precursors and intermediates. In particular the compounds mentioned in groups (I-a) to (I-h) can be combined both with the general and the preferred, particularly preferred, etc., meanings, where here, too, in each case all combinations between the preferred ranges are possible. 
     Finally, it has been found that the novel 1-methyl-3-dihalogenomethyl-5-halogenopyrazole (thio)carboxamides of the formula (I) have very good microbicidal properties and can be used for controlling unwanted microorganisms both in crop protection and in the protection of materials. 
     Furthermore, it has been found that 1-methyl-3-dihalogenomethyl-5-halogenopyrazolecarboxamides of the formula (I) wherein T represents an oxygen atom are obtained when carboxylic acid derivatives of the formula (II) 
     
       
         
         
             
             
         
       
         
         
           
             in which 
             X 1  represents halogen or hydroxyl, 
             Hal1 and Hal2 independently of one another represent chlorine or fluorine; 
             are reacted with amine derivatives of the formula (III) 
           
         
       
    
     
       
         
         
             
             
         
       
         
         
           
             in which R, L and Q have the meanings given above, 
             if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent. 
           
         
       
    
     This process for synthesizing such amides of the formula (I) has already been described sufficiently: WO-A 2006/061215, WO-A 2005/042494, WO-A 2005/042493, WO-A 2008/095890, WO-A: 
     The acids and acid halides of the formula (II) used 
     
       
         
         
             
             
         
       
         
         
           
             in which 
             X 1  represents halogen or hydroxyl, 
             are novel and are synthesized as described below: 
           
         
       
    
     Preference is given to compounds of the formula (II) where X 1  represents hydroxyl, chlorine or fluorine. 
     A further aspect of the invention comprises the process P1 according to the invention for synthesizing the acid chlorides of the formula (II), as shown in the reaction scheme below: 
     
       
         
         
             
             
         
       
     
     The compound of the formula (IIa), 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde, is known from WO-2004/014138 (Example 35). 
     Step 1 in process P1 according to the invention is carried out in the presence of an oxidizing agent and, if required, in the presence of a solvent. 
     Steps 2 and 5 in process P1 according to the invention are carried out in the presence of an acid halide former and, if required, in the presence of a solvent. 
     Step 3 in process P1 according to the invention is carried out in the presence of a fluorinating agent and, if required, in the presence of a solvent. 
     Step 4 in process P1 according to the invention is carried out in the presence of an acid or a base and, if required, in the presence of a solvent. 
     Suitable oxidizing agents for carrying out step 1 of process P1 according to the invention are all inorganic and organic oxidizing agents customarily used for such reactions. 
     Preference is given to benzyltriethylammonium permanganate, bromine, chlorine, m-chloroperbenzoic acid, chromic acid, chromium(VI) oxide, hydrogen peroxide, hydrogen peroxide/boron trifluoride, hydrogen peroxide/urea adduct, 2-hydroxyperoxyhexafluoro-2-propanol, iodine, perbenzoic acid, peroxyacetyl nitrate, potassium permanganate, potassium ruthenate, pyridinium dichromate, ruthenium(VIII) oxide, silver(I) oxide, silver(II) oxide, silver nitrite, sodium chlorite, sodium hypochlorite, 2,2,6,6-tetramethylpiperidine-1-oxyl. 
     Suitable acid halide formers for step 2 and step 5 of process P1 according to the invention are all organic and inorganic acid halide formers customarily used for such reactions. 
     Preference is given to phosgene, phosphorus trichloride, phosphorus pentachloride, phosphorus oxytrichloride; thionyl chloride; or carbon tetrachloride/triphenylphosphine. 
     Suitable fluorinating agents for step 3 of process P1 according to the invention are those which are customarily used for such reactions. 
     Preference is given to caesium fluoride; potassium fluoride; potassium fluoride/calcium difluoride and also tetrabutylammonium fluoride. 
     Suitable solvents for steps 1 to 5 of process P1 according to the invention are all customary inert organic solvents. 
     Preference is given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decaline; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; various ethers, such as diethyl ether, cyclopentyl methyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate, sulfoxides, such as dimethyl sulfoxide, or sulfones, such as sulfolane. 
     When carrying out steps 1 to 5 of process P1 according to the invention, the reaction temperatures can be varied over a relatively wide range. In general, the steps are carried out at temperatures of 0° C. to 160° C., preferably at temperatures from 0° C. to 120° C. 
     As a means for controlling the temperature in process P1 according to the invention, it is also possible to use microwave technology. 
     Unless indicated otherwise, all steps of process P1 according to the invention are generally carried out under atmospheric pressure. However, it is also possible to operate under elevated or reduced pressure—in general between 0.1 and 10 bar. 
     For carrying out step 1 of process P1 according to the invention, in general an excess of oxidizing agent is employed per mole of the aldehyde derivative of the formula (IIa). However, it is also possible to employ the components in other ratios. 
     For carrying out steps 2 and 5 of process P1 according to the invention, in general an excess of acid halide former is employed per mole of the carboxylic acid derivative of the formula (IIb) or (IIe). However, it is also possible to employ the components in other ratios. 
     For carrying out step 3 of process P1 according to the invention, in general an excess of fluorinating agent is employed per mole of the acid halide derivative of the formula (IIc). However, it is also possible to employ the components in other ratios. 
     For carrying out step 4 of process P1 according to the invention, in general an excess of acid or base is employed per mole of the acid fluoride derivative of the formula (IId). However, it is also possible to employ the components in other ratios. 
     A further aspect of the invention comprises the process P2 according to the invention for synthesizing 1-methyl-3-dihalogenomethyl-5-halogenopyrazolethiocarboxamides of the formula (I) wherein T represents an sulfur atom, as shown in the reaction scheme below: 
     
       
         
         
             
             
         
       
         
         wherein Hal1, Hal2, R, L and Q are as herein-defined, 
         in the optionally presence of a catalytic or stoichiometric or excess amount, quantity of a base such as an inorganic and organic base. Preference is given to using alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate; heterocyclic aromatic bases, such as pyridine, picoline, lutidine, collidine; and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylaminopyridine or N-methyl-piperidine. 
       
    
     Process P2 according to the invention is performed in the presence of a thionating agent. 
     Starting amide derivatives of formula (I) can be prepared as previously described. 
     Suitable thionating agents for carrying out process P2 according to the invention can be sulfur (S), sulfhydric acid (H 2 S), sodium sulfide (Na 2 S), sodium hydrosulfide (NaHS), boron trisulfide (B 2 S 3 ), bis(diethylaluminium) sulfide ((AlEt 2 ) 2 S), ammonium sulfide ((NH 4 ) 2 S), phosphorous pentasulfide (P 2 S 5 ), Lawesson&#39;s reagent (2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane 2,4-disulfide) or a polymer-supported thionating reagent such as described in Journal of the Chemical Society, Perkin 1 (2001), 358. 
     The compounds according to the invention can be synthesized according to the process described above. Based on his expert knowledge, the person skilled in the art is able to modify the preparation processes for the compounds according to the invention in a suitable manner. 
     Certain amines of the formula (III) used are already known such as:
     2-(4-methylpentan-2-yl)thiophene-3-amine (EP-A 1 036 793, EP-A 0 737 682).   

     The compound according to the present invention can be prepared according to the general processes of preparation described above. It will nevertheless be understood that, on the basis of his general knowledge and of available publications, the skilled worker will be able to adapt this method according to the specifics of each of the compounds, which it is desired to synthesize. 
     In a further aspect, the present invention also relates to a fungicide composition comprising an effective and non-phytotoxic amount of an active compound of formula (I). 
     The expression “effective and non-phytotoxic amount” means an amount of composition according to the invention that is sufficient to control or destroy the fungi present or liable to appear on the cropsand that does not entail any appreciable symptom of phytotoxicity for the said crops. Such an amount can vary within a wide range depending on the fungus to be controlled, the type of crop, the climatic conditions and the compounds included in the fungicide composition according to the invention. This amount can be determined by systematic field trials that are within the capabilities of a person skilled in the art. 
     Thus, according to the invention, there is provided a fungicide composition comprising, as an active ingredient, an effective amount of a compound of formula (I) as herein defined and an agriculturally acceptable support, carrier or filler. 
     According to the invention, the term “support” denotes a natural or synthetic, organic or inorganic compound with that the active compound of formula (I) is combined or associated to make it easier to apply, notably to the parts of the plant. This support is thus generally inert and should be agriculturally acceptable. The support can be a solid or a liquid. Examples of suitable supports include clays, natural or synthetic silicates, silica, resins, waxes, solid fertilisers, water, alcohols, in particular butanol, organic solvents, mineral and plant oils and derivatives thereof. Mixtures of such supports can also be used. 
     The composition according to the invention can also comprise additional components. In particular, the composition can further comprise a surfactant. The surfactant can be an emulsifier, a dispersing agent or a wetting agent of ionic or non-ionic type or a mixture of such surfactants. Mention can be made, for example, of polyacrylic acid salts, lignosulfonic acid salts, phenolsulfonic or naphthalenesulfonic acid salts, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (in particular alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (in particular alkyl taurates), phosphoric esters of polyoxyethylated alcohols or phenols, fatty acid esters of polyolsand derivatives of the above compounds containing sulfate, sulfonate and phosphate functions. The presence of at least one surfactant is generally essential when the active compound and/or the inert support are water-insoluble and when the vector agent for the application is water. Preferably, surfactant content can be comprised from 5% to 40% by weight of the composition. 
     Optionally, additional components can also be included, e.g. protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilisers, sequestering agents. More generally, the active compounds can be combined with any solid or liquid additive, that complies with the usual formulation techniques. 
     In general, the composition according to the invention can contain from 0.05 to 99% by weight of active compound, preferably 10 to 70% by weight. 
     Compositions according to the invention can be used in various forms such as aerosol dispenser, capsule suspension, cold fogging concentrate, dustable powder, emulsifiable concentrate, emulsion oil in water, emulsion water in oil, encapsulated granule, fine granule, flowable concentrate for seed treatment, gas (under pressure), gas generating product, granule, hot fogging concentrate, macrogranule, microgranule, oil dispersible powder, oil miscible flowable concentrate, oil miscible liquid, paste, plant rodlet, powder for dry seed treatment, seed coated with a pesticide, soluble concentrate, soluble powder, solution for seed treatment, suspension concentrate (flowable concentrate), ultra low volume (ULV) liquid, ultra low volume (ULV) suspension, water dispersible granules or tablets, water dispersible powder for slurry treatment, water soluble granules or tablets, water soluble powder for seed treatment and wettable powder. These compositions include not only compositions that are ready to be applied to the plant or seed to be treated by means of a suitable device, such as a spraying or dusting device, but also concentrated commercial compositions that must be diluted before application to the crop. 
     The compounds according to the invention can also be mixed with one or more insecticide, fungicide, bactericide, attractant, acaricide or pheromone active substance or other compounds with biological activity. The mixtures thus obtained have normally a broadened spectrum of activity. The mixtures with other fungicide compounds are particularly advantageous. 
     Examples of suitable fungicide mixing partners can be selected in the following lists: 
     (1) Inhibitors of the ergosterol biosynthesis, for example (1.1) aldimorph (1704-28-5), (1.2) azaconazole (60207-31-0), (1.3) bitertanol (55179-31-2), (1.4) bromuconazole (116255-48-2), (1.5) cyproconazole (113096-99-4), (1.6) diclobutrazole (75736-33-3), (1.7) difenoconazole (119446-68-3), (1.8) diniconazole (83657-24-3), (1.9) diniconazole-M (83657-18-5), (1.10) dodemorph (1593-77-7), (1.11) dodemorph acetate (31717-87-0), (1.12) epoxiconazole (106325-08-0), (1.13) etaconazole (60207-93-4), (1.14) fenarimol (60168-88-9), (1.15) fenbuconazole (114369-43-6), (1.16) fenhexamid (126833-17-8), (1.17) fenpropidin (67306-00-7), (1.18) fenpropimorph (67306-03-0), (1.19) fluquinconazole (136426-54-5), (1.20) flurprimidol (56425-91-3), (1.21) flusilazole (85509-19-9), (1.22) flutriafol (76674-21-0), (1.23) furconazole (112839-33-5), (1.24) furconazole-cis (112839-32-4), (1.25) hexaconazole (79983-71-4), (1.26) imazalil (60534-80-7), (1.27) imazalil sulfate (58594-72-2), (1.28) imibenconazole (86598-92-7), (1.29) ipconazole (125225-28-7), (1.30) metconazole (125116-23-6), (1.31) myclobutanil (88671-89-0), (1.32) naftifine (65472-88-0), (1.33) nuarimol (63284-71-9), (1.34) oxpoconazole (174212-12-5), (1.35) paclobutrazol (76738-62-0), (1.36) pefurazoate (101903-30-4), (1.37) penconazole (66246-88-6), (1.38) piperalin (3478-94-2), (1.39) prochloraz (67747-09-5), (1.40) propiconazole (60207-90-1), (1.41) prothioconazole (178928-70-6), (1.42) pyributicarb (88678-67-5), (1.43) pyrifenox (88283-41-4), (1.44) quinconazole (103970-75-8), (1.45) simeconazole (149508-90-7), (1.46) spiroxamine (118134-30-8), (1.47) tebuconazole (107534-96-3), (1.48) terbinafine (91161-71-6), (1.49) tetraconazole (112281-77-3), (1.50) triadimefon (43121-43-3), (1.51) triadimenol (89482-17-7), (1.52) tridemorph (81412-43-3), (1.53) triflumizole (68694-11-1), (1.54) triforine (26644-46-2), (1.55) triticonazole (131983-72-7), (1.56) uniconazole (83657-22-1), (1.57) uniconazole-p (83657-17-4), (1.58) viniconazole (77174-66-4), (1.59) voriconazole (137234-62-9), (1.60) 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol (129586-32-9), (1.61) methyl 1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate (110323-95-0), (1.62) N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide, (1.63) N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide and (1.64) O-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]1H-imidazole-1-carbothioate (111226-71-2). 
     (2) inhibitors of the respiratory chain at complex I or II, for example (2.1) bixafen (581809-46-3), (2.2) boscalid (188425-85-6), (2.3) carboxin (5234-68-4), (2.4) diflumetorim (130339-07-0), (2.5) fenfuram (24691-80-3), (2.6) fluopyram (658066-35-4), (2.7) flutolanil (66332-96-5), (2.8) fluxapyroxad (907204-31-3), (2.9) furametpyr (123572-88-3), (2.10) furmecyclox (60568-05-0), (2.11) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR) (881685-58-1), (2.12) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (2.13) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.14) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (2.15) isopyrazam (syn epimeric racemate 1RS,4SR,9RS), (2.16) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.17) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.18) mepronil (55814-41-0), (2.19) oxycarboxin (5259-88-1), (2.20) penflufen (494793-67-8), (2.21) penthiopyrad (183675-82-3), (2.22) sedaxane (874967-67-6), (2.23) thifluzamide (130000-40-7), (2.24) 1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, (2.25) 3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide, (2.26) 3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide, (2.27) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide (1092400-95-7) (WO 2008148570), (2.28) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine (1210070-84-0) (WO2010025451), (2.29) N-[9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.30) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide and (2.31) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide. 
     (3) inhibitors of the respiratory chain at complex III, for example (3.1) ametoctradin (865318-97-4), (3.2) amisulbrom (348635-87-0), (3.3) azoxystrobin (131860-33-8), (3.4) cyazofamid (120116-88-3), (3.5) coumethoxystrobin (850881-30-0), (3.6) coumoxystrobin (850881-70-8), (3.7) dimoxystrobin (141600-52-4), (3.8) enestroburin (238410-11-2) (WO 2004/058723), (3.9) famoxadone (131807-57-3) (WO 2004/058723), (3.10) fenamidone (161326-34-7) (WO 2004/058723), (3.11) fenoxystrobin (918162-02-4), (3.12) fluoxastrobin (361377-29-9) (WO 2004/058723), (3.13) kresoxim-methyl (143390-89-0) (WO 2004/058723), (3.14) metominostrobin (133408-50-1) (WO 2004/058723), (3.15) orysastrobin (189892-69-1) (WO 2004/058723), (3.16) picoxystrobin (117428-22-5) (WO 2004/058723), (3.17) pyraclostrobin (175013-18-0) (WO 2004/058723), (3.18) pyrametostrobin (915410-70-7) (WO 2004/058723), (3.19) pyraoxystrobin (862588-11-2) (WO 2004/058723), (3.20) pyribencarb (799247-52-2) (WO 2004/058723), (3.21) triclopyricarb (902760-40-1), (3.22) trifloxystrobin (141517-21-7) (WO 2004/058723), (3.23) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide (WO 2004/058723), (3.24) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide (WO 2004/058723), (3.25) (2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide (158169-73-4), (3.26) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide (326896-28-0), (3.27) (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide, (3.28) 2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide (119899-14-8), (3.29) 5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, (3.30) methyl (2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3-methoxyprop-2-enoate (149601-03-6), (3.31) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide (226551-21-9), (3.32) 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide (173662-97-0) and (3.33) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide (394657-24-0). 
     (4) Inhibitors of the mitosis and cell division, for example (4.1) benomyl (17804-35-2), (4.2) carbendazim (10605-21-7), (4.3) chlorfenazole (3574-96-7), (4.4) diethofencarb (87130-20-9), (4.5) ethaboxam (162650-77-3), (4.6) fluopicolide (239110-15-7), (4.7) fuberidazole (3878-19-1), (4.8) pencycuron (66063-05-6), (4.9) thiabendazole (148-79-8), (4.10) thiophanate-methyl (23564-05-8), (4.11) thiophanate (23564-06-9), (4.12) zoxamide (156052-68-5), (4.13) 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine (214706-53-3) and (4.14) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine (1002756-87-7). 
     (5) Compounds capable to have a multisite action, like for example (5.1) bordeaux mixture (8011-63-0), (5.2) captafol (2425-06-1), (5.3) captan (133-06-2) (WO 02/12172), (5.4) chlorothalonil (1897-45-6), (5.5) copper hydroxide (20427-59-2), (5.6) copper naphthenate (1338-02-9), (5.7) copper oxide (1317-39-1), (5.8) copper oxychloride (1332-40-7), (5.9) copper(2+) sulfate (7758-98-7), (5.10) dichlofluanid (1085-98-9), (5.11) dithianon (3347-22-6), (5.12) dodine (2439-10-3), (5.13) dodine free base, (5.14) ferbam (14484-64-1), (5.15) fluorofolpet (719-96-0), (5.16) folpet (133-07-3), (5.17) guazatine (108173-90-6), (5.18) guazatine acetate, (5.19) iminoctadine (13516-27-3), (5.20) iminoctadine albesilate (169202-06-6), (5.21) iminoctadine triacetate (57520-17-9), (5.22) mancopper (53988-93-5), (5.23) mancozeb (8018-01-7), (5.24) maneb (12427-38-2), (5.25) metiram (9006-42-2), (5.26) metiram zinc (9006-42-2), (5.27) oxine-copper (10380-28-6), (5.28) propamidine (104-32-5), (5.29) propineb (12071-83-9), (5.30) sulfur and sulfur preparations including calcium polysulfide (7704-34-9), (5.31) thiram (137-26-8), (5.32) tolylfluanid (731-27-1), (5.33) zineb (12122-67-7) and (5.34) ziram (137-30-4). 
     (6) Compounds capable to induce a host defence, for example (6.1) acibenzolar-5-methyl (135158-54-2), (6.2) isotianil (224049-04-1), (6.3) probenazole (27605-76-1) and (6.4) tiadinil (223580-51-6). 
     (7) Inhibitors of the amino acid and/or protein biosynthesis, for example (7.1) andoprim (23951-85-1), (7.2) blasticidin-S (2079-00-7), (7.3) cyprodinil (121552-61-2), (7.4) kasugamycin (6980-18-3), (7.5) kasugamycin hydrochloride hydrate (19408-46-9), (7.6) mepanipyrim (110235-47-7), (7.7) pyrimethanil (53112-28-0) and (7.8) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline (861647-32-7) (WO2005070917). 
     (8) Inhibitors of the ATP production, for example (8.1) fentin acetate (900-95-8), (8.2) fentin chloride (639-58-7), (8.3) fentin hydroxide (76-87-9) and (8.4) silthiofam (175217-20-6). 
     (9) Inhibitors of the cell wall synthesis, for example (9.1) benthiavalicarb (177406-68-7), (9.2) dimethomorph (110488-70-5), (9.3) flumorph (211867-47-9), (9.4) iprovalicarb (140923-17-7), (9.5) mandipropamid (374726-62-2), (9.6) polyoxins (11113-80-7), (9.7) polyoxorim (22976-86-9), (9.8) validamycin A (37248-47-8) and (9.9) valifenalate (283159-94-4; 283159-90-0). 
     (10) Inhibitors of the lipid and membrane synthesis, for example (10.1) biphenyl (92-52-4), (10.2) chloroneb (2675-77-6), (10.3) dicloran (99-30-9), (10.4) edifenphos (17109-49-8), (10.5) etridiazole (2593-15-9), (10.6) iodocarb (55406-53-6), (10.7) iprobenfos (26087-47-8), (10.8) isoprothiolane (50512-35-1), (10.9) propamocarb (25606-41-1), (10.10) propamocarb hydrochloride (25606-41-1), (10.11) prothiocarb (19622-08-3), (10.12) pyrazophos (13457-18-6), (10.13) quintozene (82-68-8), (10.14) tecnazene (117-18-0) and (10.15) tolclofos-methyl (57018-04-9). 
     (11) Inhibitors of the melanine biosynthesis, for example (11.1) carpropamid (104030-54-8), (11.2) diclocymet (139920-32-4), (11.3) fenoxanil (115852-48-7), (11.4) phthalide (27355-22-2), (11.5) pyroquilon (57369-32-1), (11.6) tricyclazole (41814-78-2) and (11.7) 2,2,2-trifluoroethyl {3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate (851524-22-6) (WO2005042474). 
     (12) Inhibitors of the nucleic acid synthesis, for example (12.1) benalaxyl (71626-11-4), (12.2) benalaxyl-M (kiralaxyl) (98243-83-5), (12.3) bupirimate (41483-43-6), (12.4) clozylacon (67932-85-8), (12.5) dimethirimol (5221-53-4), (12.6) ethirimol (23947-60-6), (12.7) furalaxyl (57646-30-7), (12.8) hymexazol (10004-44-1), (12.9) metalaxyl (57837-19-1), (12.10) metalaxyl-M (mefenoxam) (70630-17-0), (12.11) ofurace (58810-48-3), (12.12) oxadixyl (77732-09-3) and (12.13) oxolinic acid (14698-29-4). 
     (13) Inhibitors of the signal transduction, for example (13.1) chlozolinate (84332-86-5), (13.2) fenpiclonil (74738-17-3), (13.3) fludioxonil (131341-86-1), (13.4) iprodione (36734-19-7), (13.5) procymidone (32809-16-8), (13.6) quinoxyfen (124495-18-7) and (13.7) vinclozolin (50471-44-8). 
     (14) Compounds capable to act as an uncoupler, for example (14.1) binapacryl (485-31-4), (14.2) dinocap (131-72-6), (14.3) ferimzone (89269-64-7), (14.4) fluazinam (79622-59-6) and (14.5) meptyldinocap (131-72-6). 
     (15) Further compounds, for example (15.1) benthiazole (21564-17-0), (15.2) bethoxazin (163269-30-5), (15.3) capsimycin (70694-08-5), (15.4) carvone (99-49-0), (15.5) chinomethionat (2439-01-2), (15.6) pyriofenone (chlazafenone) (688046-61-9), (15.7) cufraneb (11096-18-7), (15.8) cyflufenamid (180409-60-3), (15.9) cymoxanil (57966-95-7), (15.10) cyprosulfamide (221667-31-8), (15.11) dazomet (533-74-4), (15.12) debacarb (62732-91-6), (15.13) dichlorophen (97-23-4), (15.14) diclomezine (62865-36-5), (15.15) difenzoquat (49866-87-7), (15.16) difenzoquat methylsulfate (43222-48-6), (15.17) diphenylamine (122-39-4), (15.18) ecomate, (15.19) fenpyrazamine (473798-59-3), (15.20) flumetover (154025-04-4), (15.21) fluoroimide (41205-21-4), (15.22) flusulfamide (106917-52-6), (15.23) flutianil (304900-25-2), (15.24) fosetyl-aluminium (39148-24-8), (15.25) fosetyl-calcium, (15.26) fosetyl-sodium (39148-16-8), (15.27) hexachlorobenzene (118-74-1), (15.28) irumamycin (81604-73-1), (15.29) methasulfocarb (66952-49-6), (15.30) methyl isothiocyanate (556-61-6), (15.31) metrafenone (220899-03-6), (15.32) mildiomycin (67527-71-3), (15.33) natamycin (7681-93-8), (15.34) nickel dimethyldithiocarbamate (15521-65-0), (15.35) nitrothal-isopropyl (10552-74-6), (15.36) octhilinone (26530-20-1), (15.37) oxamocarb (917242-12-7), (15.38) oxyfenthiin (34407-87-9), (15.39) pentachlorophenol and salts (87-86-5), (15.40) phenothrin, (15.41) phosphorous acid and its salts (13598-36-2), (15.42) propamocarb-fosetylate, (15.43) propanosine-sodium (88498-02-6), (15.44) proquinazid (189278-12-4), (15.45) pyrimorph (868390-90-3), (15.45e) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one (1231776-28-5), (15.45z) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one (1231776-29-6), (15.46) pyrrolnitrine (1018-71-9) (EP-A 1 559 320), (15.47) tebufloquin (376645-78-2), (15.48) tecloftalam (76280-91-6), (15.49) tolnifanide (304911-98-6), (15.50) triazoxide (72459-58-6), (15.51) trichlamide (70193-21-4), (15.52) zarilamid (84527-51-5), (15.53) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl 2-methylpropanoate (517875-34-2) (WO2003035617), (15.54) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (1003319-79-6) (WO 2008013622), (15.55) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (1003319-80-9) (WO 2008013622), (15.56) 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (1003318-67-9) (WO 2008013622), (15.57) 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl 1H-imidazole-1-carboxylate (111227-17-9), (15.58) 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine (13108-52-6), (15.59) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one (221451-58-7), (15.60) 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone, (15.61) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (1003316-53-7) (WO 2008013622), (15.62) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (1003316-54-8) (WO 2008013622), (15.63) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone (1003316-51-5) (WO 2008013622), (15.64) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (15.65) 2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl]pyridine, (15.66) 2-phenylphenol and salts (90-43-7), (15.67) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (861647-85-0) (WO2005070917), (15.68) 3,4,5-trichloropyridine-2,6-dicarbonitrile (17824-85-0), (15.69) 3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine, (15.70) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (15.71) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (15.72) 5-amino-1,3,4-thiadiazole-2-thiol, (15.73) 5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide (134-31-6), (15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine (1174376-11-4) (WO2009094442), (15.75) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine (1174376-25-0) (WO2009094442), (15.76) 5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, (15.77) ethyl (2Z)-3-amino-2-cyano-3-phenylprop-2-enoate, (15.78) N′-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (15.79) N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide, (15.80) N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide, (15.81) N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide, (15.82) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide, (15.83) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide, (15.84) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide (221201-92-9), (15.85) N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide (221201-92-9), (15.86) N′-{4-[(3-tert-butyl-4-cyano-1,2-thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylimidoformamide, (15.87) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide (922514-49-6) (WO 2007014290), (15.88) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-O—N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide (922514-07-6) (WO 2007014290), (15.89) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide (922514-48-5) (WO 2007014290), (15.90) pentyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.91) phenazine-1-carboxylic acid, (15.92) quinolin-8-ol (134-31-6), (15.93) quinolin-8-ol sulfate (2:1) (134-31-6) and (15.94) tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate. 
     (16) Further compounds, for example (16.1) 1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (16.2) N-(4′-chlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (16.3) N-(2′,4′-dichlorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (16.4) 3-(difluoromethyl)-1-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (16.5) N-(2′,5′-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, (16.6) 3-(difluoromethyl)-1-methyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.7) 5-fluoro-1,3-dimethyl-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.8) 2-chloro-N-[4′-(prop-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide (known from WO 2004/058723), (16.9) 3-(difluoromethyl)-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.10) N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.11) 3-(difluoromethyl)-N-(4′-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.12) N-(4′-ethynylbiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.13) 2-chloro-N-(4′-ethynylbiphenyl-2-yl)pyridine-3-carboxamide (known from WO 2004/058723), (16.14) 2-chloro-N-[4′-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide (known from WO 2004/058723), (16.15) 4-(difluoromethyl)-2-methyl-N-[4′-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide (known from WO 2004/058723), (16.16) 5-fluoro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.17) 2-chloro-N-[4′-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide (known from WO 2004/058723), (16.18) 3-(difluoromethyl)-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.19) 5-fluoro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide (known from WO 2004/058723), (16.20) 2-chloro-N-[4′-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]pyridine-3-carboxamide (known from WO 2004/058723), (16.21) (5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone (known from EP-A 1 559 320), (16.22) N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulfonyl)valinamide (220706-93-4), (16.23) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid and (16.24) but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate. 
     All named mixing partners of the classes (1) to (16) can, if their functional groups enable this, optionally form salts with suitable bases or acids. 
     The composition according to the invention comprising a mixture of a compound of formula (I) with a bactericide compound can also be particularly advantageous. Examples of suitable bactericide mixing partners can be selected in the following list: bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations. 
     The compounds of formula (I) and the fungicide composition according to the invention can be used to curatively or preventively control the phytopathogenic fungi of plants or crops. 
     Thus, according to a further aspect of the invention, there is provided a method for curatively or preventively controlling the phytopathogenic fungi of plants or crops characterised in that a compound of formula (I) or a fungicide composition according to the invention is applied to the seed, the plant or to the fruit of the plant or to the soil wherein the plant is growing or wherein it is desired to grow. 
     The method of treatment according to the invention can also be useful to treat propagation material such as tubers or rhizomes, but also seeds, seedlings or seedlings pricking out and plants or plants pricking out. This method of treatment can also be useful to treat roots. The method of treatment according to the invention can also be useful to treat the overground parts of the plant such as trunks, stems or stalks, leaves, flowers and fruit of the concerned plant. 
     According to the invention all plants and plant parts can be treated. By plants is meant all plants and plant populations such as desirable and undesirable wild plants, cultivars and plant varieties (whether or not protectable by plant variety or plant breeder&#39;s rights). Cultivars and plant varieties can be plants obtained by conventional propagation and breeding methods which can be assisted or supplemented by one or more biotechnological methods such as by use of double haploids, protoplast fusion, random and directed mutagenesis, molecular or genetic markers or by bioengineering and genetic engineering methods. By plant parts is meant all above ground and below ground parts and organs of plants such as shoot, leaf, blossom and root, whereby for example leaves, needles, stems, branches, blossoms, fruiting bodies, fruits and seed as well as roots, corms and rhizomes are listed. Crops and vegetative and generative propagating material, for example cuttings, corms, rhizomes, runners and seeds also belong to plant parts. 
     Among the plants that can be protected by the method according to the invention, mention may be made of major field crops like corn, soybean, cotton,  Brassica  oilseeds such as  Brassica napus  (e.g. canola),  Brassica rapa, B. juncea  (e.g. mustard) and  Brassica carinata , rice, wheat, sugarbeet, sugarcane, oats, rye, barley, millet, triticale, flax, vine and various fruits and vegetables of various botanical taxa such as Rosaceae sp. (for instance pip fruit such as apples and pears, but also stone fruit such as apricots, cherries, almonds and peaches, berry fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actimidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana trees and plantings), Rubiaceae sp. (for instance coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemons, oranges and grapefruit); Solanaceae sp. (for instance tomatoes, potatoes, peppers, eggplant), Liliaceae sp., Compositiae sp. (for instance lettuce, artichoke and chicory—including root chicory, endive or common chicory), Umbelliferae sp. (for instance carrot, parsley, celery and celeriac), Cucurbitaceae sp. (for instance cucumber—including pickling cucumber, squash, watermelon, gourds and melons), Alliaceae sp. (for instance onions and leek), Cruciferae sp. (for instance white cabbage, red cabbage, broccoli, cauliflower, brussel sprouts, pak Choi, kohlrabi, radish, horseradish, cress, Chinese cabbage), Leguminosae sp. (for instance peanuts, peas and beans beans—such as climbing beans and broad beans), Chenopodiaceae sp. (for instance mangold, spinach beet, spinach, beetroots), Malvaceae (for instance okra), Asparagaceae (for instance asparagus); horticultural and forest crops; ornamental plants; as well as genetically modified homologues of these crops. 
     The method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMOs), e.g. plants or seeds. Genetically modified plants (or transgenic plants) are plants of which a heterologous gene has been stably integrated into genome. The expression “heterologous gene” essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology or RNA interference—RNAi—technology). A heterologous gene that is located in the genome is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event. 
     Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in additional effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the active compounds and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, bigger fruits, larger plant height, greener leaf color, earlier flowering, higher quality and/or a higher nutritional value of the harvested products, higher sugar concentration within the fruits, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected. 
     At certain application rates, the active compound combinations according to the invention may also have a strengthening effect in plants. Accordingly, they are also suitable for mobilizing the defense system of the plant against attack by unwanted microorganisms. This may, if appropriate, be one of the reasons of the enhanced activity of the combinations according to the invention, for example against fungi. Plant-strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances or combinations of substances which are capable of stimulating the defense system of plants in such a way that, when subsequently inoculated with unwanted microorganisms, the treated plants display a substantial degree of resistance to these microorganisms. In the present case, unwanted microorganisms are to be understood as meaning phytopathogenic fungi, bacteria and viruses. Thus, the substances according to the invention can be employed for protecting plants against attack by the abovementioned pathogens within a certain period of time after the treatment. The period of time within which protection is effected generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds. 
     Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means). 
     Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids. 
     Examples of nematode resistant plants are described in e.g. U.S. patent application Ser. Nos. 11/765,491, 11/765,494, 10/926,819, 10/782,020, 12/032,479, 10/783,417, 10/782,096, 11/657,964, 12/192,904, 11/396,808, 12/166,253, 12/166,239, 12/166,124, 12/166,209, 11/762,886, 12/364,335, 11/763,947, 12/252,453, 12/209,354, 12/491,396 or 12/497,221. 
     Plants and plant cultivars which may also be treated according to the invention are those plants which are resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance. 
     Plants and plant cultivars which may also be treated according to the invention, are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Further yield traits include seed composition, such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability. 
     Examples of plants with the above-mentioned traits are non-exhaustively listed in Table A. 
     Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses). Such plants are typically made by crossing an inbred male-sterile parent line (the female parent) with another inbred male-fertile parent line (the male parent). Hybrid seed is typically harvested from the male sterile plants and sold to growers. Male sterile plants can sometimes (e.g. in corn) be produced by detasseling, i.e. the mechanical removal of the male reproductive organs (or males flowers) but, more typically, male sterility is the result of genetic determinants in the plant genome. In that case, and especially when seed is the desired product to be harvested from the hybrid plants it is typically useful to ensure that male fertility in the hybrid plants is fully restored. This can be accomplished by ensuring that the male parents have appropriate fertility restorer genes which are capable of restoring the male fertility in hybrid plants that contain the genetic determinants responsible for male-sterility. Genetic determinants for male sterility may be located in the cytoplasm. Examples of cytoplasmic male sterility (CMS) were for instance described in  Brassica  species (WO 92/05251, WO 95/09910, WO 98/27806, WO 05/002324, WO 06/021972 and U.S. Pat. No. 6,229,072). However, genetic determinants for male sterility can also be located in the nuclear genome. Male sterile plants can also be obtained by plant biotechnology methods such as genetic engineering. A particularly useful means of obtaining male-sterile plants is described in WO 89/10396 in which, for example, a ribonuclease such as barnase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored by expression in the tapetum cells of a ribonuclease inhibitor such as barstar (e.g. WO 91/02069). 
     Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance. 
     Herbicide-resistant plants are for example glyphosate-tolerant plants, i.e. plants made tolerant to the herbicide glyphosate or salts thereof. Plants can be made tolerant to glyphosate through different means. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium  Salmonella typhimurium  (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium  Agrobacterium  sp. (Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), the genes encoding a Petunia EPSPS (Shah et al., 1986, Science 233, 478-481), a Tomato EPSPS (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289), or an  Eleusine  EPSPS (WO 01/66704). It can also be a mutated EPSPS as described in for example EP 0837944, WO 00/66746, WO 00/66747 or WO02/26995. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate oxido-reductase enzyme as described in U.S. Pat. Nos. 5,776,760 and 5,463,175. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate acetyl transferase enzyme as described in for example WO 02/36782, WO 03/092360, WO 05/012515 and WO 07/024,782. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above-mentioned genes, as described in for example WO 01/024615 or WO 03/013226. Plants expressing EPSPS genes that confer glyphosate tolerance are described in e.g. U.S. patent application Ser. Nos. 11/517,991, 10/739,610, 12/139,408, 12/352,532, 11/312,866, 11/315,678, 12/421,292, 11/400,598, 11/651,752, 11/681,285, 11/605,824, 12/468,205, 11/760,570, 11/762,526, 11/769,327, 11/769,255, 11/943,801 or 12/362,774. Plants comprising other genes that confer glyphosate tolerance, such as decarboxylase genes, are described in e.g. U.S. patent application Ser. Nos. 11/588,811, 11/185,342, 12/364,724, 11/185,560 or 12/423,926. 
     Other herbicide resistant plants are for example plants that are made tolerant to herbicides inhibiting the enzyme glutamine synthase, such as bialaphos, phosphinothricin or glufosinate. Such plants can be obtained by expressing an enzyme detoxifying the herbicide or a mutant glutamine synthase enzyme that is resistant to inhibition, e.g. described in U.S. patent application Ser. No. 11/760,602. One such efficient detoxifying enzyme is an enzyme encoding a phosphinothricin acetyltransferase (such as the bar or pat protein from  Streptomyces  species). Plants expressing an exogenous phosphinothricin acetyltransferase are for example described in U.S. Pat. Nos. 5,561,236; 5,648,477; 5,646,024; 5,273,894; 5,637,489; 5,276,268; 5,739,082; 5,908,810 and 7,112,665. 
     Further herbicide-tolerant plants are also plants that are made tolerant to the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase (HPPD). Hydroxyphenylpyruvatedioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is transformed into homogentisate. Plants tolerant to HPPD-inhibitors can be transformed with a gene encoding a naturally-occurring resistant HPPD enzyme, or a gene encoding a mutated or chimeric HPPD enzyme as described in WO 96/38567, WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387, or U.S. Pat. No. 6,768,044. Tolerance to HPPD-inhibitors can also be obtained by transforming plants with genes encoding certain enzymes enabling the formation of homogentisate despite the inhibition of the native HPPD enzyme by the HPPD-inhibitor. Such plants and genes are described in WO 99/34008 and WO 02/36787. Tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding an enzyme having prephenate deshydrogenase (PDH) activity in addition to a gene encoding an HPPD-tolerant enzyme, as described in WO 2004/024928. Further, plants can be made more tolerant to HPPD-inhibitor herbicides by adding into their genome a gene encoding an enzyme capable of metabolizing or degrading HPPD inhibitors, such as the CYP450 enzymes shown in WO 2007/103567 and WO 2008/150473. 
     Still further herbicide resistant plants are plants that are made tolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pryimidinyoxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinone herbicides. Different mutations in the ALS enzyme (also known as acetohydroxyacid synthase, AHAS) are known to confer tolerance to different herbicides and groups of herbicides, as described for example in Tranel and Wright (2002, Weed Science 50:700-712), but also, in U.S. Pat. Nos. 5,605,011, 5,378,824, 5,141,870, and 5,013,659. The production of sulfonylurea-tolerant plants and imidazolinone-tolerant plants is described in U.S. Pat. Nos. 5,605,011; 5,013,659; 5,141,870; 5,767,361; 5,731,180; 5,304,732; 4,761,373; 5,331,107; 5,928,937; and 5,378,824; and international publication WO 96/33270. Other imidazolinone-tolerant plants are also described in for example WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351, and WO 2006/060634. Further sulfonylurea- and imidazolinone-tolerant plants are also described in for example WO 07/024,782 and U.S. Patent Application No. 61/288,958. 
     Other plants tolerant to imidazolinone and/or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or mutation breeding as described for example for soybeans in U.S. Pat. No. 5,084,082, for rice in WO 97/41218, for sugar beet in U.S. Pat. No. 5,773,702 and WO 99/057965, for lettuce in U.S. Pat. No. 5,198,599, or for sunflower in WO 01/065922. 
     Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance. 
     An “insect-resistant transgenic plant”, as used herein, includes any plant containing at least one transgene comprising a coding sequence encoding:
         1) an insecticidal crystal protein from  Bacillus thuringiensis  or an insecticidal portion thereof, such as the insecticidal crystal proteins listed by Crickmore et al. (1998, Microbiology and Molecular Biology Reviews, 62: 807-813), updated by Crickmore et al. (2005) at the  Bacillus thuringiensis  toxin nomenclature, online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal portions thereof, e.g., proteins of the Cry protein classes Cry1Ab, Cry1Ac, Cry1B, Cry1C, Cry1D, Cry1F, Cry2Ab, Cry3Aa, or Cry3Bb or insecticidal portions thereof (e.g. EP 1999141 and WO 2007/107302), or such proteins encoded by synthetic genes as e.g. described in and U.S. patent application Ser. No. 12/249,016; or   2) a crystal protein from  Bacillus thuringiensis  or a portion thereof which is insecticidal in the presence of a second other crystal protein from  Bacillus thuringiensis  or a portion thereof, such as the binary toxin made up of the Cry34 and Cry35 crystal proteins (Moellenbeck et al. 2001, Nat. Biotechnol. 19: 668-72; Schnepf et al. 2006, Applied Environm. Microbiol. 71, 1765-1774) or the binary toxin made up of the Cry1A or Cry1F proteins and the Cry2Aa or Cry2Ab or Cry2Ae proteins (U.S. patent application Ser. No. 12/214,022 and EP 08010791.5); or   3) a hybrid insecticidal protein comprising parts of different insecticidal crystal proteins from  Bacillus thuringiensis , such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g., the Cry1A.105 protein produced by corn event MON89034 (WO 2007/027777); or   4) a protein of any one of 1) to 3) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation, such as the Cry3Bb1 protein in corn events MON863 or MON88017, or the Cry3A protein in corn event MIR604; or   5) an insecticidal secreted protein from  Bacillus thuringiensis  or  Bacillus cereus , or an insecticidal portion thereof, such as the vegetative insecticidal (VIP) proteins listed at: http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html, e.g., proteins from the VIP3Aa protein class; or   6) a secreted protein from  Bacillus thuringiensis  or  Bacillus cereus  which is insecticidal in the presence of a second secreted protein from  Bacillus thuringiensis  or  B. cereus , such as the binary toxin made up of the VIP1A and VIP2A proteins (WO 94/21795); or   7) a hybrid insecticidal protein comprising parts from different secreted proteins from  Bacillus thuringiensis  or  Bacillus cereus , such as a hybrid of the proteins in 1) above or a hybrid of the proteins in 2) above; or   8) a protein of any one of 5) to 7) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation (while still encoding an insecticidal protein), such as the VIP3Aa protein in cotton event COT102; or   9) a secreted protein from  Bacillus thuringiensis  or  Bacillus cereus  which is insecticidal in the presence of a crystal protein from  Bacillus thuringiensis , such as the binary toxin made up of VIP3 and Cry1A or Cry1F (U.S. Patent Appl. No. 61/126,083 and 61/195,019), or the binary toxin made up of the VIP3 protein and the Cry2Aa or Cry2Ab or Cry2Ae proteins (U.S. patent application Ser. No. 12/214,022 and EP 08010791.5).   10) a protein of 9) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation (while still encoding an insecticidal protein)       

     Of course, an insect-resistant transgenic plant, as used herein, also includes any plant comprising a combination of genes encoding the proteins of any one of the above classes 1 to 10. In one embodiment, an insect-resistant plant contains more than one transgene encoding a protein of any one of the above classes 1 to 10, to expand the range of target insect species affected when using different proteins directed at different target insect species, or to delay insect resistance development to the plants by using different proteins insecticidal to the same target insect species but having a different mode of action, such as binding to different receptor binding sites in the insect. 
     An “insect-resistant transgenic plant”, as used herein, further includes any plant containing at least one transgene comprising a sequence producing upon expression a double-stranded RNA which upon ingestion by a plant insect pest inhibits the growth of this insect pest, as described e.g. in WO 2007/080126, WO 2006/129204, WO 2007/074405, WO 2007/080127 and WO 2007/035650. 
     Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance. Particularly useful stress tolerance plants include:
         1) plants which contain a transgene capable of reducing the expression and/or the activity of poly(ADP-ribose) polymerase (PARP) gene in the plant cells or plants as described in WO 00/04173, WO/2006/045633, EP 04077984.5, or EP 06009836.5.   2) plants which contain a stress tolerance enhancing transgene capable of reducing the expression and/or the activity of the PARG encoding genes of the plants or plants cells, as described e.g. in WO 2004/090140.   3) plants which contain a stress tolerance enhancing transgene coding for a plant-functional enzyme of the nicotineamide adenine dinucleotide salvage synthesis pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyl transferase, nicotinamide adenine dinucleotide synthetase or nicotine amide phosphorybosyltransferase as described e.g. in EP 04077624.7, WO 2006/133827, PCT/EP07/002,433, EP 1999263, or WO 2007/107326.       

     Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention show altered quantity, quality and/or storage-stability of the harvested product and/or altered properties of specific ingredients of the harvested product such as:
         1) transgenic plants which synthesize a modified starch, which in its physical-chemical characteristics, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscosity behaviour, the gelling strength, the starch grain size and/or the starch grain morphology, is changed in comparison with the synthesised starch in wild type plant cells or plants, so that this is better suited for special applications. Said transgenic plants synthesizing a modified starch are disclosed, for example, in EP 0571427, WO 95/04826, EP 0719338, WO 96/15248, WO 96/19581, WO 96/27674, WO 97/11188, WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472, WO 97/45545, WO 98/27212, WO 98/40503, WO99/58688, WO 99/58690, WO 99/58654, WO 00/08184, WO 00/08185, WO 00/08175, WO 00/28052, WO 00/77229, WO 01/12782, WO 01/12826, WO 02/101059, WO 03/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO 00/22140, WO 2006/063862, WO 2006/072603, WO 02/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP 07090009.7, WO 01/14569, WO 02/79410, WO 03/33540, WO 2004/078983, WO 01/19975, WO 95/26407, WO 96/34968, WO 98/20145, WO 99/12950, WO 99/66050, WO 99/53072, U.S. Pat. No. 6,734,341, WO 00/11192, WO 98/22604, WO 98/32326, WO 01/98509, WO 01/98509, WO 2005/002359, U.S. Pat. No. 5,824,790, U.S. Pat. No. 6,013,861, WO 94/04693, WO 94/09144, WO 94/11520, WO 95/35026, WO 97/20936   2) transgenic plants which synthesize non starch carbohydrate polymers or which synthesize non starch carbohydrate polymers with altered properties in comparison to wild type plants without genetic modification. Examples are plants producing polyfructose, especially of the inulin and levan-type, as disclosed in EP 0663956, WO 96/01904, WO 96/21023, WO 98/39460, and WO 99/24593, plants producing alpha-1,4-glucans as disclosed in WO 95/31553, US 2002031826, U.S. Pat. No. 6,284,479, U.S. Pat. No. 5,712,107, WO 97/47806, WO 97/47807, WO 97/47808 and WO 00/14249, plants producing alpha-1,6 branched alpha-1,4-glucans, as disclosed in WO 00/73422, plants producing alternan, as disclosed in e.g. WO 00/47727, WO 00/73422, EP 06077301.7, U.S. Pat. No. 5,908,975 and EP 0728213,   3) transgenic plants which produce hyaluronan, as for example disclosed in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006304779, and WO 2005/012529.   4) transgenic plants or hybrid plants, such as onions with characteristics such as ‘high soluble solids content’, ‘low pungency’ (LP) and/or ‘long storage’ (LS), as described in U.S. patent application Ser. No. 12/020,360 and 61/054,026.       

     Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics and include:
         a) Plants, such as cotton plants, containing an altered form of cellulose synthase genes as described in WO 98/00549   b) Plants, such as cotton plants, containing an altered form of rsw2 or rsw3 homologous nucleic acids as described in WO 2004/053219   c) Plants, such as cotton plants, with increased expression of sucrose phosphate synthase as described in WO 01/17333   d) Plants, such as cotton plants, with increased expression of sucrose synthase as described in WO 02/45485   e) Plants, such as cotton plants, wherein the timing of the plasmodesmatal gating at the basis of the fiber cell is altered, e.g. through downregulation of fiber-selective β-1,3-glucanase as described in WO 2005/017157, or as described in EP 08075514.3 or U.S. Patent Appl. No. 61/128,938   f) Plants, such as cotton plants, having fibers with altered reactivity, e.g. through the expression of N-acetylglucosaminetransferase gene including nodC and chitin synthase genes as described in WO 2006/136351       

     Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related  Brassica  plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered oil profile characteristics and include:
         a) Plants, such as oilseed rape plants, producing oil having a high oleic acid content as described e.g. in U.S. Pat. No. 5,969,169, U.S. Pat. No. 5,840,946 or U.S. Pat. No. 6,323,392 or U.S. Pat. No. 6,063,947   b) Plants such as oilseed rape plants, producing oil having a low linolenic acid content as described in U.S. Pat. No. 6,270,828, U.S. Pat. No. 6,169,190, or U.S. Pat. No. 5,965,755   c) Plant such as oilseed rape plants, producing oil having a low level of saturated fatty acids as described e.g. in U.S. Pat. No. 5,434,283 or U.S. patent application Ser. No. 12/668,303       

     Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related  Brassica  plants, with altered seed shattering characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered seed shattering characteristics and include plants such as oilseed rape plants with delayed or reduced seed shattering as described in U.S. Patent Appl. No. 61/135,230 WO09/068,313 and WO10/006,732. 
     Particularly useful transgenic plants which may be treated according to the invention are plants containing transformation events, or combination of transformation events, that are the subject of petitions for non-regulated status, in the United States of America, to the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) whether such petitions are granted or are still pending. At any time this information is readily available from APHIS (4700 River Road Riverdale, Md. 20737, USA), for instance on its internet site (URL http://www.aphis.usda.gov/brs/notreg.html). On the filing date of this application the petitions for nonregulated status that were pending with APHIS or granted by APHIS were those listed in table B which contains the following information:
         Petition: the identification number of the petition. Technical descriptions of the transformation events can be found in the individual petition documents which are obtainable from APHIS, for example on the APHIS website, by reference to this petition number. These descriptions are herein incorporated by reference.   Extension of Petition: reference to a previous petition for which an extension is requested.   Institution: the name of the entity submitting the petition.   Regulated article: the plant species concerned.   Transgenic phenotype: the trait conferred to the plants by the transformation event.   Transformation event or line: the name of the event or events (sometimes also designated as lines or lines) for which nonregulated status is requested.   APHIS documents: various documents published by APHIS in relation to the Petition and which can be requested with APHIS.       

     Additional particularly useful plants containing single transformation events or combinations of transformation events are listed for example in the databases from various national or regional regulatory agencies (see for example http://gmoinfo.jrc.it/gmp_browse.aspx and http://www.agbios.com/dbase.php). 
     Further particularly transgenic plants include plants containing a transgene in an agronomically neutral or beneficial position as described in any of the patent publications listed in Table C. 
     
       
         
           
               
               
             
               
                 TABLE A 
               
               
                   
               
               
                 Trait 
                 Reference 
               
               
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                 Water use efficiency 
                 WO 2000/073475 
                   
               
               
                 Nitrogen use efficiency 
                 WO 1995/009911 
                 WO 2007/076115 
               
               
                   
                 WO 1997/030163 
                 WO 2005/103270 
               
               
                   
                 WO 2007/092704 
                 WO 2002/002776 
               
               
                 Improved photosynthesis 
                 WO 2008/056915 
                 WO 2004/101751 
               
               
                 Nematode resistance 
                 WO 1995/020669 
                 WO 2003/033651 
               
               
                   
                 WO 2001/051627 
                 WO 1999/060141 
               
               
                   
                 WO 2008/139334 
                 WO 1998/012335 
               
               
                   
                 WO 2008/095972 
                 WO 1996/030517 
               
               
                   
                 WO 2006/085966 
                 WO 1993/018170 
               
               
                 Reduced pod dehiscence 
                 WO 2006/009649 
                 WO 1997/013865 
               
               
                   
                 WO 2004/113542 
                 WO 1996/030529 
               
               
                   
                 WO 1999/015680 
                 WO 1994/023043 
               
               
                   
                 WO 1999/000502 
               
               
                 Aphid resistance 
                 WO 2006/125065 
                 WO 2008/067043 
               
               
                   
                 WO 1997/046080 
                 WO 2004/072109 
               
               
                 Sclerotinia resistance 
                 WO 2006/135717 
                 WO 2005/000007 
               
               
                   
                 WO 2006/055851 
                 WO 2002/099385 
               
               
                   
                 WO 2005/090578 
                 WO 2002/061043 
               
               
                 Botrytis resistance 
                 WO 2006/046861 
                 WO 2002/085105 
               
               
                 Bremia resistance 
                 US 20070022496 
                 WO 2004/049786 
               
               
                   
                 WO 2000/063432 
               
               
                 Erwinia resistance 
                 WO 2004/049786 
               
               
                 Closterovirus resistance 
                 WO 2007/073167 
                 WO 2002/022836 
               
               
                   
                 WO 2007/053015 
               
               
                 Stress tolerance (including 
                 WO 2010/019838 
                 WO2008/002480 
               
               
                 drought tolerance) 
                 WO 2009/049110 
                 WO2005/033318 
               
               
                 Tobamovirus resistance 
                 WO 2006/038794 
               
               
                   
               
            
           
         
       
     
     
       
         
           
               
             
               
                 TABLE B 
               
             
            
               
                   
               
               
                 Petitions of Nonregulated Status Granted or Pending by APHIS as of Mar. 31, 2010 
               
            
           
           
               
               
            
               
                 Applicant Documents 
                   
               
            
           
           
               
               
               
               
               
               
            
               
                   
                 Extension of 
                   
                   
                   
                   
               
               
                   
                 Petition 
                   
                 Regulated 
                 Transgenic 
                 Transformation 
               
               
                 Petition 
                 Number *** 
                 Institution 
                 Article 
                 Phenotype 
                 Event or Line 
               
               
                   
               
            
           
           
               
            
               
                 Petitions for Nonregulated Status Pending 
               
            
           
           
               
               
               
               
               
               
            
               
                 10-070-01p 
                   
                 Virginia Tech 
                 Peanut 
                 Sclerotinia blight 
                 N70, P39, and 
               
               
                   
                   
                   
                   
                 resistant 
                 W171 
               
               
                 09-349-01p 
                   
                 Dow 
                 Soybean 
                 Herbicide Tolerant 
                 DAS-68416-4 
               
               
                   
                   
                 AgroSciences 
               
               
                 09-328-01p 
                   
                 Bayer Crop 
                 Soybean 
                 Herbicide Tolerant 
                 FG72 
               
               
                   
                   
                 Science 
               
               
                 09-233-01p 
                   
                 Dow 
                 Corn 
                 Herbicide Tolerant 
                 DAS-40278-9 
               
               
                 09-201-01p 
                   
                 Monsanto 
                 Soybean 
                   
                 MON-877Ø5-6 
               
               
                 09-183-01p 
                   
                 Monsanto 
                 Soybean 
                   
                 MON-87769 
               
               
                 09-082-01p 
                   
                 Monsanto 
                 Soybean 
                 Lepidopteran resistant 
                 MON 87701 
               
               
                 09-063-01p 
                   
                 Stine Seed 
                 Corn 
                 Glyphosate tolerant 
                 HCEM485 
               
               
                 09-055-01p 
                   
                 Monsanto 
                 Corn 
                 Drought Tolerant 
                 MON 87460 
               
               
                 09-015-01p 
                   
                 BASF Plant 
                 Soybean 
                 Herbicide Tolerant 
                 BPS-CV127-9 
               
               
                   
                   
                 Science, LLC 
                   
                   
                 Soybean 
               
               
                 08-366-01p 
                   
                 ArborGen 
                 Eucalyptus 
                 Freeze Tolerant, 
                 ARB-FTE1-08 
               
               
                   
                   
                   
                   
                 Fertility Altered 
               
               
                 08-340-01p 
                   
                 Bayer 
                 Cotton 
                 Glufosinate Tolerant, 
                 T304-40XGHB119 
               
               
                   
                   
                   
                   
                 Insect Resistant 
               
               
                 08-338-01p 
                   
                 Pioneer 
                 Corn 
                 Male Sterile, Fertility 
                 DP-32138-1 
               
               
                   
                   
                   
                   
                 Restored, Visual 
               
               
                   
                   
                   
                   
                 Marker 
               
               
                 08-315-01p 
                   
                 Florigene 
                 Rose 
                 Altered Flower Color 
                 IFD-524Ø1-4 and 
               
               
                   
                   
                   
                   
                   
                 IFD-529Ø1-9 
               
               
                 07-253-01p 
                   
                 Syngenta 
                 Corn 
                 Lepidopteran resistant 
                 MIR-162 Maize 
               
               
                 07-108-01p 
                   
                 Syngenta 
                 Cotton 
                 Lepidopteran Resistant 
                 COT67B 
               
               
                 06-354-01p 
                   
                 Pioneer 
                 Soybean 
                 High Oleic Acid 
                 DP-3Ø5423-1 
               
               
                 05-280-01p 
                   
                 Syngenta 
                 Corn 
                 Thermostable alpha- 
                 3272 
               
               
                   
                   
                   
                   
                 amylase 
               
               
                 04-110-01p 
                   
                 Monsanto &amp; 
                 Alfalfa 
                 Glyphosate Tolerant 
                 J101, J163 
               
               
                   
                   
                 Forage Genetics 
               
               
                 03-104-01p 
                   
                 Monsanto &amp; 
                 Creeping 
                 Glyphosate Tolerant 
                 ASR368 
               
               
                   
                   
                 Scotts 
                 bentgrass 
               
            
           
           
               
            
               
                 Petitions for Nonregulated Status Granted 
               
            
           
           
               
               
               
               
               
               
            
               
                 07-152-01p 
                   
                 Pioneer 
                 Corn 
                 glyphosate &amp; 
                 DP-098140-6 
               
               
                   
                   
                   
                   
                 Imidazolinone tolerant 
               
               
                 04-337-01p 
                   
                 University of 
                 Papaya 
                 Papaya Ringspot Virus 
                 X17-2 
               
               
                   
                   
                 Florida 
                   
                 Resistant 
               
               
                 06-332-01p 
                   
                 Bayer 
                 Cotton 
                 Glyphosate tolerant 
                 GHB614 
               
               
                   
                   
                 CropScience 
               
               
                 06-298-01p 
                   
                 Monsanto 
                 Corn 
                 European Corn Borer 
                 MON 89034 
               
               
                   
                   
                   
                   
                 resistant 
               
               
                 06-271-01p 
                   
                 Pioneer 
                 Soybean 
                 Glyphosate &amp; 
                 356043 
               
               
                   
                   
                   
                   
                 acetolactate synthase 
                 (DP-356Ø43-5) 
               
               
                   
                   
                   
                   
                 tolerant 
               
               
                 06-234-01p 
                 98-329-01p 
                 Bayer 
                 Rice 
                 Phosphinothricin 
                 LLRICE601 
               
               
                   
                   
                 CropScience 
                   
                 tolerant 
               
               
                 06-178-01p 
                   
                 Monsanto 
                 Soybean 
                 Glyphosate tolerant 
                 MON 89788 
               
               
                 04-362-01p 
                   
                 Syngenta 
                 Corn 
                 Corn Rootworm 
                 MIR604 
               
               
                   
                   
                   
                   
                 Protected 
               
               
                 04-264-01p 
                   
                 ARS 
                 Plum 
                 Plum Pox Virus 
                 C5 
               
               
                   
                   
                   
                   
                 Resistant 
               
               
                 04-229-01p 
                   
                 Monsanto 
                 Corn 
                 High Lysine 
                 LY038 
               
               
                 04-125-01p 
                   
                 Monsanto 
                 Corn 
                 Corn Rootworm 
                 88017 
               
               
                   
                   
                   
                   
                 Resistant 
               
               
                 04-086-01p 
                   
                 Monsanto 
                 Cotton 
                 Glyphosate Tolerant 
                 MON 88913 
               
               
                 03-353-01p 
                   
                 Dow 
                 Corn 
                 Corn Rootworm 
                 59122 
               
               
                   
                   
                   
                   
                 Resistant 
               
               
                 03-323-01p 
                   
                 Monsanto 
                 Sugar 
                 Glyphosate Tolerant 
                 H7-1 
               
               
                   
                   
                   
                 Beet 
               
               
                 03-181-01p 
                 00-136-01p 
                 Dow 
                 Corn 
                 Lepidopteran Resistant 
                 TC-6275 
               
               
                   
                   
                   
                   
                 &amp; Phosphinothricin 
               
               
                   
                   
                   
                   
                 tolerant 
               
               
                 03-155-01p 
                   
                 Syngenta 
                 Cotton 
                 Lepidopteran Resistant 
                 COT 102 
               
               
                 03-036-01p 
                   
                 Mycogen/Dow 
                 Cotton 
                 Lepidopteran Resistant 
                 281-24-236 
               
               
                 03-036-02p 
                   
                 Mycogen/Dow 
                 Cotton 
                 Lepidopteran Resistant 
                 3006-210-23 
               
               
                 02-042-01p 
                   
                 Aventis 
                 Cotton 
                 Phosphinothericin 
                 LLCotton25 
               
               
                   
                   
                   
                   
                 tolerant 
               
               
                 01-324-01p 
                 98-216-01p 
                 Monsanto 
                 Rapeseed 
                 Glyphosate tolerant 
                 RT200 
               
               
                 01-206-01p 
                 98-278-01p 
                 Aventis 
                 Rapeseed 
                 Phosphinothricin 
                 MS1 &amp; RF1/RF2 
               
               
                   
                   
                   
                   
                 tolerant &amp; pollination 
               
               
                   
                   
                   
                   
                 control 
               
               
                 01-206-02p 
                 97-205-01p 
                 Aventis 
                 Rapeseed 
                 Phosphinothricin 
                 Topas 19/2 
               
               
                   
                   
                   
                   
                 tolerant 
               
               
                 01-137-01p 
                   
                 Monsanto 
                 Corn 
                 Corn Rootworm 
                 MON 863 
               
               
                   
                   
                   
                   
                 Resistant 
               
               
                 01-121-01p 
                   
                 Vector 
                 Tobacco 
                 Reduced nicotine 
                 Vector 21-41 
               
               
                 00-342-01p 
                   
                 Monsanto 
                 Cotton 
                 Lepidopteran resistant 
                 Cotton Event 
               
               
                   
                   
                   
                   
                   
                 15985 
               
               
                 00-136-01p 
                   
                 Mycogen c/o 
                 Corn 
                 Lepidopteran resistant 
                 Line 1507 
               
               
                   
                   
                 Dow &amp; Pioneer 
                   
                 phosphinothricin 
               
               
                   
                   
                   
                   
                 tolerant 
               
               
                 00-011-01p 
                 97-099-01p 
                 Monsanto 
                 Corn 
                 Glyphosate tolerant 
                 NK603 
               
               
                 99-173-01p 
                 97-204-01p 
                 Monsanto 
                 Potato 
                 PLRV &amp; CPB resistant 
                 RBMT22-82 
               
               
                 98-349-01p 
                 95-228-01p 
                 AgrEvo 
                 Corn 
                 Phosphinothricin 
                 MS6 
               
               
                   
                   
                   
                   
                 tolerant and Male 
               
               
                   
                   
                   
                   
                 sterile 
               
               
                 98-335-01p 
                   
                 U. of 
                 Flax 
                 Tolerant to soil 
                 CDC Triffid 
               
               
                   
                   
                 Saskatchewan 
                   
                 residues of sulfonyl 
               
               
                   
                   
                   
                   
                 urea herbicide 
               
               
                 98-329-01p 
                   
                 AgrEvo 
                 Rice 
                 Phosphinothricin 
                 LLRICE06, 
               
               
                   
                   
                   
                   
                 tolerant 
                 LLRICE62 
               
               
                 98-278-01p 
                   
                 AgrEvo 
                 Rapeseed 
                 Phosphinothricin 
                 MS8 &amp; RF3 
               
               
                   
                   
                   
                   
                 tolerant &amp; Pollination 
               
               
                   
                   
                   
                   
                 control 
               
               
                 98-238-01p 
                   
                 AgrEvo 
                 Soybean 
                 Phosphinothricin 
                 GU262 
               
               
                   
                   
                   
                   
                 tolerant 
               
               
                 98-216-01p 
                   
                 Monsanto 
                 Rapeseed 
                 Glyphosate tolerant 
                 RT73 
               
               
                 98-173-01p 
                   
                 Novartis Seeds &amp; 
                 Beet 
                 Glyphosate tolerant 
                 GTSB77 
               
               
                   
                   
                 Monsanto 
               
               
                 98-014-01p 
                 96-068-01p 
                 AgrEvo 
                 Soybean 
                 Phosphinothricin 
                 A5547-127 
               
               
                   
                   
                   
                   
                 tolerant 
               
               
                 97-342-01p 
                   
                 Pioneer 
                 Corn 
                 Male sterile &amp; 
                 676, 678, 680 
               
               
                   
                   
                   
                   
                 Phosphinothricin 
               
               
                   
                   
                   
                   
                 tolerant 
               
               
                 97-339-01p 
                   
                 Monsanto 
                 Potato 
                 CPB &amp; PVY resistant 
                 RBMT15-101, 
               
               
                   
                   
                   
                   
                   
                 SEMT15-02, 
               
               
                   
                   
                   
                   
                   
                 SEMT15-15 
               
               
                 97-336-01p 
                   
                 AgrEvo 
                 Beet 
                 Phosphinothricin 
                 T-120-7 
               
               
                   
                   
                   
                   
                 tolerant 
               
               
                 97-287-01p 
                   
                 Monsanto 
                 Tomato 
                 Lepidopteran resistant 
                 5345 
               
               
                 97-265-01p 
                   
                 AgrEvo 
                 Corn 
                 Phosphinothricin 
                 CBH-351 
               
               
                   
                   
                   
                   
                 tolerant &amp; Lep. 
               
               
                   
                   
                   
                   
                 resistant 
               
               
                 97-205-01p 
                   
                 AgrEvo 
                 Rapeseed 
                 Phosphinothricin 
                 T45 
               
               
                   
                   
                   
                   
                 tolerant 
               
               
                 97-204-01p 
                   
                 Monsanto 
                 Potato 
                 CPB &amp; PLRV resistant 
                 RBMT21-129 &amp; 
               
               
                   
                   
                   
                   
                   
                 RBMT21-350 
               
               
                 97-148-01p 
                   
                 Bejo 
                 
                   Cichorium 
                 
                 Male sterile 
                 RM3-3, RM3-4, 
               
               
                   
                   
                   
                 
                   intybus 
                 
                   
                 RM3-6 
               
               
                 97-099-01p 
                   
                 Monsanto 
                 Corn 
                 Glyphosate tolerant 
                 GA21 
               
               
                 97-013-01p 
                   
                 Calgene 
                 Cotton 
                 Bromoxynil tolerant &amp; 
                 Events 31807 &amp; 
               
               
                   
                   
                   
                   
                 Lepidopteran resistant 
                 31808 
               
               
                 97-008-01p 
                   
                 Du Pont 
                 Soybean 
                 Oil profile altered 
                 G94-1, G94-19, G- 
               
               
                   
                   
                   
                   
                   
                 168 
               
               
                 96-317-01p 
                   
                 Monsanto 
                 Corn 
                 Glyphosate tolerant &amp; 
                 MON802 
               
               
                   
                   
                   
                   
                 ECB resistant 
               
               
                 96-291-01p 
                   
                 DeKalb 
                 Corn 
                 European Corn Borer 
                 DBT418 
               
               
                   
                   
                   
                   
                 resistant 
               
               
                 96-248-01p 
                 92-196-01p 
                 Calgene 
                 Tomato 
                 Fruit ripening altered 
                 1 additional 
               
               
                   
                   
                   
                   
                   
                 FLAVRSAVR line 
               
               
                 96-068-01p 
                   
                 AgrEvo 
                 Soybean 
                 Phosphinothricin 
                 W62, W98, A2704- 
               
               
                   
                   
                   
                   
                 tolerant 
                 12, A2704-21, 
               
               
                   
                   
                   
                   
                   
                 A5547-35 
               
               
                 96-051-01p 
                   
                 Cornell U 
                 Papaya 
                 PRSV resistant 
                 55-1, 63-1 
               
               
                 96-017-01p 
                 95-093-01p 
                 Monsanto 
                 Corn 
                 European Corn Borer 
                 MON809 &amp; 
               
               
                   
                   
                   
                   
                 resistant 
                 MON810 
               
               
                 95-352-01p 
                   
                 Asgrow 
                 Squash 
                 CMV, ZYMV, WMV2 
                 CZW-3 
               
               
                   
                   
                   
                   
                 resistant 
               
               
                 95-338-01p 
                   
                 Monsanto 
                 Potato 
                 CPB resistant 
                 SBT02-5 &amp; -7, 
               
               
                   
                   
                   
                   
                   
                 ATBT04-6 
               
               
                   
                   
                   
                   
                   
                 &amp;-27, -30, -31, -36 
               
               
                 95-324-01p 
                   
                 Agritope 
                 Tomato 
                 Fruit ripening altered 
                 35 1 N 
               
               
                 95-256-01p 
                   
                 Du Pont 
                 Cotton 
                 Sulfonylurea tolerant 
                 19-51a 
               
               
                 95-228-01p 
                   
                 Plant Genetic 
                 Corn 
                 Male sterile 
                 MS3 
               
               
                   
                   
                 Systems 
               
               
                 95-195-01p 
                   
                 Northrup King 
                 Corn 
                 European Corn Borer 
                 Bt11 
               
               
                   
                   
                   
                   
                 resistant 
               
               
                 95-179-01p 
                 92-196-01p 
                 Calgene 
                 Tomato 
                 Fruit ripening altered 
                 2 additional 
               
               
                   
                   
                   
                   
                   
                 FLAVRSAVR lines 
               
               
                 95-145-01p 
                   
                 DeKalb 
                 Corn 
                 Phosphinothricin 
                 B16 
               
               
                   
                   
                   
                   
                 tolerant 
               
               
                 95-093-01p 
                   
                 Monsanto 
                 Corn 
                 Lepidopteran resistant 
                 MON 80100 
               
               
                 95-053-01p 
                   
                 Monsanto 
                 Tomato 
                 Fruit ripening altered 
                 8338 
               
               
                 95-045-01p 
                   
                 Monsanto 
                 Cotton 
                 Glyphosate tolerant 
                 1445, 1698 
               
               
                 95-030-01p 
                 92-196-01p 
                 Calgene 
                 Tomato 
                 Fruit ripening altered 
                 20 additional 
               
               
                   
                   
                   
                   
                   
                 FLAVRSAVR lines 
               
               
                 94-357-01p 
                   
                 AgrEvo 
                 Corn 
                 Phosphinothricin 
                 T14, T25 
               
               
                   
                   
                   
                   
                 tolerant 
               
               
                 94-319-01p 
                   
                 Ciba Seeds 
                 Corn 
                 Lepidopteran resistant 
                 Event 176 
               
               
                 94-308-01p 
                   
                 Monsanto 
                 Cotton 
                 Lepidopteran resistant 
                 531, 757, 1076 
               
               
                 94-290-01p 
                   
                 Zeneca &amp; 
                 Tomato 
                 Fruit polygalacturonase 
                 B, Da, F 
               
               
                   
                   
                 Petoseed 
                   
                 level decreased 
               
               
                 94-257-01p 
                   
                 Monsanto 
                 Potato 
                 Coleopteran resistant 
                 BT6, BT10, BT12, 
               
               
                   
                   
                   
                   
                   
                 BT16, BT17, BT18, 
               
               
                   
                   
                   
                   
                   
                 BT23 
               
               
                 94-230-01p 
                 92-196-01p 
                 Calgene 
                 Tomato 
                 Fruit ripening altered 
                 9 additional 
               
               
                   
                   
                   
                   
                   
                 FLAVRSAVR lines 
               
               
                 94-228-01p 
                   
                 DNA Plant Tech 
                 Tomato 
                 Fruit ripening altered 
                 1345-4 
               
               
                 94-227-01p 
                 92-196-01p 
                 Calgene 
                 Tomato 
                 Fruit ripening altered 
                 Line N73 1436-111 
               
               
                 94-090-01p 
                   
                 Calgene 
                 Rapeseed 
                 Oil profile altered 
                 pCGN3828- 
               
               
                   
                   
                   
                   
                   
                 212/86- 18 &amp; 23 
               
               
                 93-258-01p 
                   
                 Monsanto 
                 Soybean 
                 Glyphosate tolerant 
                 40-3-2 
               
               
                 93-196-01p 
                   
                 Calgene 
                 Cotton 
                 Bromoxynil tolerant 
                 BXN 
               
               
                 92-204-01p 
                   
                 Upjohn 
                 Squash 
                 WMV2 &amp; ZYMV 
                 ZW-20 
               
               
                   
                   
                   
                   
                 resistant 
               
               
                 92-196-01p 
                   
                 Calgene 
                 Tomato 
                 Fruit ripening altered 
                 FLAVR SAVR 
               
               
                   
               
               
                 NOTE: 
               
               
                 To obtain the most up-to-date list of Crops No Longer Regulated, please look at the Current Status of Petitions. This list is automatically updated and reflects all petitions received to date by APHIS, including petitions pending, withdrawn, or approved. 
               
               
                 Abbreviations: 
               
               
                 CMV—cucumber mosaic virus; CPB—colorado potato beetle; PLRV—potato leafroll virus; PRSV—papaya ringspot virus; PVY—potato virus Y; WMV2—watermelon mosaic virus 2 ZYMV—zucchini yellow mosaic virus 
               
               
                 *** Extension of Petition Number: Under 7CFR 340.6(e) a person may request that APHIS extend a determination of non-regulated status to other organisms based on their similarity of the previously deregulated article. This column lists the previously granted petition of that degregulated article. 
               
               
                 **** Preliminary EA: The Environmental Assessment initially available for Public comment prior to finalization. 
               
            
           
         
       
     
     
       
         
           
               
               
               
               
             
               
                 TABLE C 
               
               
                   
               
               
                 Plant species 
                 Event 
                 Trait 
                 Patent reference 
               
               
                   
               
             
            
               
                 Corn 
                 PV-ZMGT32 (NK603) 
                 Glyphosate tolerance 
                 US 2007-056056 
               
               
                 Corn 
                 MIR604 
                 Insect resistance (Cry3a055) 
                 EP 1 737 290 
               
               
                 Corn 
                 LY038 
                 High lysine content 
                 U.S. Pat. No. 7,157,281 
               
               
                 Corn 
                 3272 
                 Self processing corn (alpha- 
                 US 2006-230473 
               
               
                   
                   
                 amylase) 
               
               
                 Corn 
                 PV-ZMIR13 
                 Insect resistance (Cry3Bb) 
                 US 2006-095986 
               
               
                   
                 (MON863) 
               
               
                 Corn 
                 DAS-59122-7 
                 Insect resistance 
                 US 2006-070139 
               
               
                   
                   
                 (Cry34Ab1/Cry35Ab1) 
               
               
                 Corn 
                 TC1507 
                 Insect resistance (Cry1F) 
                 U.S. Pat. No. 7,435,807 
               
               
                 Corn 
                 MON810 
                 Insect resistance (Cry1Ab) 
                 US 2004-180373 
               
               
                 Corn 
                 VIP1034 
                 Insect resistance 
                 WO 03/052073 
               
               
                 Corn 
                 B16 
                 Glufosinate resistance 
                 US 2003-126634 
               
               
                 Corn 
                 GA21 
                 Glyphosate resistance 
                 U.S. Pat. No. 6,040,497 
               
               
                 Corn 
                 GG25 
                 Glyphosate resistance 
                 U.S. Pat. No. 6,040,497 
               
               
                 Corn 
                 GJ11 
                 Glyphosate resistance 
                 U.S. Pat. No. 6,040,497 
               
               
                 Corn 
                 FI117 
                 Glyphosate resistance 
                 U.S. Pat. No. 6,040,497 
               
               
                 Corn 
                 GAT-ZM1 
                 Glufosinate tolerance 
                 WO 01/51654 
               
               
                 Corn 
                 MON87460 
                 Drought tolerance 
                 WO 2009/111263 
               
               
                 Corn 
                 DP-098140-6 
                 Glyphosate tolerance/ALS 
                 WO 2008/112019 
               
               
                   
                   
                 inhibitor tolerance 
               
               
                 Wheat 
                 Event 1 
                 Fusarium resistance 
                 CA 2561992 
               
               
                   
                   
                 (trichothecene 3-O- 
               
               
                   
                   
                 acetyltransferase) 
               
               
                 Sugar beet 
                 T227-1 
                 Glyphosate tolerance 
                 US 2004-117870 
               
               
                 Sugar beet 
                 H7-1 
                 Glyphosate tolerance 
                 WO 2004-074492 
               
               
                 Soybean 
                 MON89788 
                 Glyphosate tolerance 
                 US 2006-282915 
               
               
                 Soybean 
                 A2704-12 
                 Glufosinate tolerance 
                 WO 2006/108674 
               
               
                 Soybean 
                 A5547-35 
                 Glufosinate tolerance 
                 WO 2006/108675 
               
               
                 Soybean 
                 DP-305423-1 
                 High oleic acid/ALS inhibitor 
                 WO 2008/054747 
               
               
                   
                   
                 tolerance 
               
               
                 Rice 
                 GAT-OS2 
                 Glufosinate tolerance 
                 WO 01/83818 
               
               
                 Rice 
                 GAT-OS3 
                 Glufosinate tolerance 
                 US 2008-289060 
               
               
                 Rice 
                 PE-7 
                 Insect resistance (Cry1Ac) 
                 WO 2008/114282 
               
               
                 Oilseed rape 
                 MS-B2 
                 Male sterility 
                 WO 01/31042 
               
               
                 Oilseed rape 
                 MS-BN1/RF-BN1 
                 Male sterility/restoration 
                 WO 01/41558 
               
               
                 Oilseed rape 
                 RT73 
                 Glyphosate resistance 
                 WO 02/36831 
               
               
                 Cotton 
                 CE43-67B 
                 Insect resistance (Cry1Ab) 
                 WO 2006/128573 
               
               
                 Cotton 
                 CE46-02A 
                 Insect resistance (Cry1Ab) 
                 WO 2006/128572 
               
               
                 Cotton 
                 CE44-69D 
                 Insect resistance (Cry1Ab) 
                 WO 2006/128571 
               
               
                 Cotton 
                 1143-14A 
                 Insect resistance (Cry1Ab) 
                 WO 2006/128569 
               
               
                 Cotton 
                 1143-51B 
                 Insect resistance (Cry1Ab) 
                 WO 2006/128570 
               
               
                 Cotton 
                 T342-142 
                 Insect resistance (Cry1Ab) 
                 WO 2006/128568 
               
               
                 Cotton 
                 event3006-210-23 
                 Insect resistance (Cry1Ac) 
                 WO 2005/103266 
               
               
                 Cotton 
                 PV-GHGT07 (1445) 
                 Glyphosate tolerance 
                 US 2004-148666 
               
               
                 Cotton 
                 MON88913 
                 Glyphosate tolerance 
                 WO 2004/072235 
               
               
                 Cotton 
                 EE-GH3 
                 Glyphosate tolerance 
                 WO 2007/017186 
               
               
                 Cotton 
                 T304-40 
                 Insect-resistance (Cry1Ab) 
                 WO2008/122406 
               
               
                 Cotton 
                 Cot202 
                 Insect resistance (VIP3) 
                 US 2007-067868 
               
               
                 Cotton 
                 LLcotton25 
                 Glufosinate resistance 
                 WO 2007/017186 
               
               
                 Cotton 
                 EE-GH5 
                 Insect resistance (Cry1Ab) 
                 WO 2008/122406 
               
               
                 Cotton 
                 event 281-24-236 
                 Insect resistance (Cry1F) 
                 WO 2005/103266 
               
               
                 Cotton 
                 Cot102 
                 Insect resistance (Vip3A) 
                 US 2006-130175 
               
               
                 Cotton 
                 MON 15985 
                 Insect resistance (Cry1A/Cry2Ab) 
                 US 2004-250317 
               
               
                 Bent Grass 
                 Asr-368 
                 Glyphosate tolerance 
                 US 2006-162007 
               
               
                 Brinjal 
                 EE-1 
                 Insect resistance (Cry1Ac) 
                 WO 2007/091277 
               
               
                   
               
            
           
         
       
     
     Among the diseases of plants or crops that can be controlled by the method according to the invention, mention can be made of: 
     Powdery mildew diseases such as:
           Blumeria  diseases, caused for example by  Blumeria graminis;        Podosphaera  diseases, caused for example by  Podosphaera leucotricha;        Sphaerotheca  diseases, caused for example by  Sphaerotheca fuliginea;        Uncinula  diseases, caused for example by  Uncinula necator;          

     Rust diseases such as:
           Gymnosporangium  diseases, caused for example by  Gymnosporangium sabinae;        Hemileia  diseases, caused for example by  Hemileia vastatrix;        Phakopsora  diseases, caused for example by  Phakopsora pachyrhizi  or  Phakopsora meibomiae;        Puccinia  diseases, caused for example by  Puccinia recondite, Puccinia graminis  or  Puccinia striiformis;        Uromyces  diseases, caused for example by  Uromyces appendiculatus;          

     Oomycete diseases such as:
           Albugo  diseases caused for example by  Albugo candida;        Bremia  diseases, caused for example by  Bremia lactucae;        Peronospora  diseases, caused for example by  Peronospora pisi  or  P. brassicae;        Phytophthora  diseases, caused for example by  Phytophthora infestans;        Plasmopara  diseases, caused for example by  Plasmopara viticola;        Pseudoperonospora  diseases, caused for example by  Pseudoperonospora humuli  or     Pseudoperonospora cubensis;        Pythium  diseases, caused for example by  Pythium ultimum;          

     Leafspot, leaf blotch and leaf blight diseases such as:
           Alternaria  diseases, caused for example by  Alternaria solani;        Cercospora  diseases, caused for example by  Cercospora beticola;        Cladiosporum  diseases, caused for example by  Cladiosporium cucumerinum;        Cochliobolus  diseases, caused for example by  Cochliobolus sativus  (Conidiaform:  Drechslera , Syn:  Helminthosporium ) or  Cochliobolus miyabeanus;        Colletotrichum  diseases, caused for example by  Colletotrichum lindemuthanium;        Cycloconium  diseases, caused for example by  Cycloconium oleaginum;        Diaporthe  diseases, caused for example by  Diaporthe citri;        Elsinoe  diseases, caused for example by  Elsinoe fawcettii;        Gloeosporium  diseases, caused for example by  Gloeosporium laeticolor;        Glomerella  diseases, caused for example by  Glomerella cingulata;        Guignardia  diseases, caused for example by  Guignardia bidwelli;        Leptosphaeria  diseases, caused for example by  Leptosphaeria maculans; Leptosphaeria nodorum;        Magnaporthe  diseases, caused for example by  Magnaporthe grisea;        Mycosphaerella  diseases, caused for example by  Mycosphaerella graminicola; Mycosphaerella arachidicola; Mycosphaerella fijiensis;        Phaeosphaeria  diseases, caused for example by  Phaeosphaeria nodorum;        Pyrenophora  diseases, caused for example by  Pyrenophora teres , or  Pyrenophora tritici repentis;        Ramularia  diseases, caused for example by  Ramularia collo - cygni , or  Ramularia areola;        Rhynchosporium  diseases, caused for example by  Rhynchosporium secalis;        Septoria  diseases, caused for example by  Septoria apii  or  Septoria lycopercisi;        Typhula  diseases, caused for example by  Typhula incarnate;        Venturia  diseases, caused for example by  Venturia inaequalis ; Root, Sheath and stem diseases such as:     Corticium  diseases, caused for example by  Corticium graminearum;        Fusarium  diseases, caused for example by  Fusarium oxysporum;        Gaeumannomyces  diseases, caused for example by  Gaeumannomyces graminis;        Rhizoctonia  diseases, caused for example by  Rhizoctonia solani;        Sarocladium  diseases caused for example by  Sarocladium oryzae;        Sclerotium  diseases caused for example by  Sclerotium oryzae;        Tapesia  diseases, caused for example by  Tapesia acuformis;        Thielaviopsis  diseases, caused for example by  Thielaviopsis basicola;          

     Ear and panicle diseases such as:
           Alternaria  diseases, caused for example by  Alternaria  spp.;     Aspergillus  diseases, caused for example by  Aspergillus flavus;        Cladosporium  diseases, caused for example by  Cladosporium  spp.;     Claviceps  diseases, caused for example by  Claviceps purpurea;        Fusarium  diseases, caused for example by  Fusarium culmorum;        Gibberella  diseases, caused for example by  Gibberella zeae;        Monographella  diseases, caused for example by  Monographella nivalis;          

     Smut and bunt diseases such as:
           Sphacelotheca  diseases, caused for example by  Sphacelotheca reiliana;        Tilletia  diseases, caused for example by  Tilletia caries;        Urocystis  diseases, caused for example by  Urocystis occulta;        Ustilago  diseases, caused for example by  Ustilago nuda;          

     Fruit rot and mould diseases such as:
           Aspergillus  diseases, caused for example by  Aspergillus flavus;        Botrytis  diseases, caused for example by  Botrytis cinerea;        Penicillium  diseases, caused for example by  Penicillium expansum;        Rhizopus  diseases caused by example by  Rhizopus stolonifer        Sclerotinia  diseases, caused for example by  Sclerotinia sclerotiorum;        Verticilium  diseases, caused for example by  Verticilium alboatrum;          

     Seed and soilborne decay, mould, wilt, rot and damping-off diseases:
           Alternaria  diseases, caused for example by  Alternaria brassicicola        Aphanomyces  diseases, caused for example by  Aphanomyces euteiches        Ascochyta  diseases, caused for example by  Ascochyta lentis        Aspergillus  diseases, caused for example by  Aspergillus flavus        Cladosporium  diseases, caused for example by  Cladosporium herbarum        Cochliobolus  diseases, caused for example by  Cochliobolus sativus      (Conidiaform:  Drechslera, Bipolaris  Syn:  Helminthosporium );     Colletotrichum  diseases, caused for example by  Colletotrichum coccodes;        Fusarium  diseases, caused for example by  Fusarium culmorum;        Gibberella  diseases, caused for example by  Gibberella zeae;        Macrophomina  diseases, caused for example by  Macrophomina phaseolina        Monographella  diseases, caused for example by  Monographella nivalis;        Penicillium  diseases, caused for example by  Penicillium expansum        Phoma  diseases, caused for example by  Phoma lingam        Phomopsis  diseases, caused for example by  Phomopsis sojae;        Phytophthora  diseases, caused for example by  Phytophthora cactorum;        Pyrenophora  diseases, caused for example by  Pyrenophora graminea        Pyricularia  diseases, caused for example by  Pyricularia oryzae;        Pythium  diseases, caused for example by  Pythium ultimum;        Rhizoctonia  diseases, caused for example by  Rhizoctonia solani;        Rhizopus  diseases, caused for example by  Rhizopus oryzae        Sclerotium  diseases, caused for example by  Sclerotium rolfsii;        Septoria  diseases, caused for example by  Septoria nodorum;        Typhula  diseases, caused for example by  Typhula incarnate;        Verticillium  diseases, caused for example by  Verticillium dahliae;          

     Canker, broom and dieback diseases such as:
           Nectria  diseases, caused for example by  Nectria galligena;          

     Blight diseases such as:
           Monilinia  diseases, caused for example by  Monilinia laxa;          

     Leaf blister or leaf curl diseases such as:
           Exobasidium  diseases caused for example by  Exobasidium vexans        Taphrina  diseases, caused for example by  Taphrina deformans;          

     Decline diseases of wooden plants such as:
           Esca  diseases, caused for example by  Phaemoniella clamydospora;        Eutypa  dyeback, caused for example by  Eutypa lata;        Ganoderma  diseases caused for example by  Ganoderma boninense;        Rigidoporus  diseases caused for example by  Rigidoporus lignosus          

     Diseases of Flowers and Seeds such as 
       Botrytis  diseases caused for example by  Botrytis cinerea;    
     Diseases of Tubers such as
           Rhizoctonia  diseases caused for example by  Rhizoctonia solani;          

       Helminthosporium  diseases caused for example by  Helminthosporium solani;    
     Club root diseases such as
           Plasmodiophora  diseases, cause for example by Plamodiophora brassicae.       

     Diseases caused by Bacterial Organisms such as
           Xanthomonas  species for example  Xanthomonas campestris  pv.  oryzae;        Pseudomonas  species for example  Pseudomonas syringae  pv.  lachrymans;        Erwinia  species for example  Erwinia amylovora.          

     The composition according to the invention may also be used against fungal diseases liable to grow on or inside timber. The term “timber” means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood. The method for treating timber according to the invention mainly consists in contacting one or more compounds according to the invention or a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means. 
     The dose of active compound usually applied in the method of treatment according to the invention is generally and advantageously from 10 to 800 g/ha, preferably from 50 to 300 g/ha for applications in foliar treatment. The dose of active substance applied is generally and advantageously from 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed in the case of seed treatment. It is clearly understood that the doses indicated herein are given as illustrative examples of the method according to the invention. A person skilled in the art will know how to adapt the application doses, notably according to the nature of the plant or crop to be treated. 
     The compounds or mixtures according to the invention can also be used for the preparation of composition useful to curatively or preventively treat human or animal fungal diseases such as, for example, mycoses, dermatoses, trichophyton diseases and candidiases or diseases caused by  Aspergillus  spp., for example  Aspergillus fumigatus.    
     The preparation and the use of the active compounds I-methyl-3-dihalogenomethyl-5-halogenopyrazole(thio)carboxamides of the formula (I) according to the invention and the intermediates is illustrated by the examples below. 
     Procedure for Synthesizing Amides of the Formula (I) According to the Invention from Compounds of the Formula (II) and Compounds of the Formula (III): 
     4 mL of a 0.15 molar solution (0.60 mmol) of an amine according to formula III as described above are initially charged in a 13 mL Chemspeed™ reaction tube in dichloromethane, followed by 0.72 mmol of triethylamine. At a rate of 1 mL/min, 2 mL of a 0.30 molar solution of the acyl chloride (IIb) or (IIe) (0.60 mmol) are added, and the mixture is stirred at room temperature overnight. 1 mL of water is then added, and the mixture is applied to a cartridge with basic alumina (weight 2 g) and eluted with dichloromethane. The solvent is removed and the reaction mixture is analyzed by LCMS and NMR. Impure products are purified further by preparative LCMS. 
     Procedure for Synthesizing the Carboxylic Acid Derivatives of the Formula (II) According to the Invention According to Process P1: 
     5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (Example IIb) 
     
       
         
         
             
             
         
       
     
     In a 500 mL round-bottom flask, 6.0 g (31 mmol) of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbaldehyde were taken up in 30 mL of toluene. A solution of 2.4 g (62 mmol) of sodium hydroxide in 6 mL of water was added to the reaction mixture, followed by 103 mL of a 30% strength solution of hydrogen peroxide in water. During the addition, the temperature was kept below 37° C. The reaction mixture was then stirred at 50° C. for 7 h. After cooling, the organic phase was extracted with 100 mL of water. The aqueous phase was acidified to pH 2 using dilute hydrochloric acid. The white precipitate formed was filtered off, washed twice with 20 mL of water and dried. This gave 3.2 g of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid as a white solid. 
       1 H NMR (400 MHz, DMSO-d 6 ) δ ppm: 3.78 (s, 3H); 7.12 (t, 1H, J HF =53.60 Hz); 13.19 (s, 1H); 
     IR (KBr): 1688 cm −1  (C═O); 2200-3200 cm −1  broad; 
     5-Chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride (Example IIc) 
     
       
         
         
             
             
         
       
     
     3.2 g of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid and 44.3 mL of thionyl chloride were heated under reflux for 5 h. After cooling, the reaction mixture was concentrated under reduced pressure, giving 3.5 g of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride as a yellow oil. 
       1 H NMR (400 MHz, CHCl 3 -d 6 ) δ ppm: 3.97 (s, 3H); 7.00 (t, J=52.01 Hz, 1H); 
     IR (TQ): 1759 and 1725 cm −1  (C═O); 
     3-(Difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl fluoride (Example IId) 
     
       
         
         
             
             
         
       
     
     At 100° C., a solution of 5.0 g (22 mmol) of 5-chloro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride in 15 mL of toluene was added to a dried solution of 4.0 g (70 mmol) of potassium fluoride in 21 mL of tetrahydrothiophene-1,1-dioxide. The reaction mixture was then stirred at 190-200° C. for 22 h. Removal of the solvent under reduced pressure gave 8 g of a solution (25% molar) of 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl fluoride in tetrahydrothiophene-1,1-dioxide. 
       1 H NMR (250 MHz, CHCl 3 -d 6 ) δ ppm: 3.87 (s, 3H); 6.79 (t, J=53.75 Hz, 1H); 
       19 F NMR (250 MHz, CHCl 3 -d 6 ) δ ppm: 45.37 (s, COF); −117.5 (d, J=28.2 Hz); −131.6 (m); 
     5-Fluoro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid (Example IIe) 
     
       
         
         
             
             
         
       
     
     67.5 g of a solution (10% molar) of 3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl fluoride in tetrahydrothiophene-1,1-dioxide were added dropwise to 400 mL of an aqueous 1N NaOH solution. During the addition, the temperature was kept below 20° C. After 2 h of stirring at room temperature, the mixture was carefully acidified to pH 2 using concentrated hydrochloric acid. The white precipitate formed was filtered off, washed with water and dried. This gave 6 g of 5-fluoro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid as a white solid. 
       1 H NMR (400 MHz, DMSO-d 6 ) δ ppm: 3.90 (s, 3H); 7.22 (t, 1H, J HF =53.55 Hz); 13.33 (s, 1H); 
     5-Fluoro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride (Example IIf) 
     
       
         
         
             
             
         
       
     
     9.1 g of 5-fluoro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid and 75.5 mL of thionyl chloride were heated under reflux for 1.5 h. After cooling, the reaction mixture was concentrated under reduced pressure, giving 10 g of 5-fluoro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride as a yellow oil. 
     GC-MS (M= +. )=212; fragments: (M +. -Cl)=177 and (M +. -F)=193; 
     General Procedure for Synthesizing Thioamides of the Formula (I) According to the Invention from Amides of the Formula (I) According to Process P2: 
     In a 13 mLChemspeed™ vial is weighed 0.27 mmol of phosphorous pentasulfide (P 2 S 5 ). 3 mL of a 0.18 molar solution of the amide (I) (0.54 mmol) in dioxane is added and the mixture is heated at reflux for two hours. The temperature is then cooled to 80° C. and 2.5 mL of water are added. The mixture is heated at 80° C. for one more hour. 2 mL of water are then added and the reaction mixture is extracted twice by 4 mL of dichloromethane. The organic phase is deposited on a basic alumina cartridge (2 g) and eluted twice by 8 mL of dichloromethane. The solvents are removed and the crude thioamide derivative is analyzed by LCMS and NMR. Insufficiently pure compounds are further purified by preparative LCMS. 
     The following examples of compounds according to formula (I) are listed in Table 1 below: 
     
       
         
         
             
             
         
       
         
         where R represents hydrogen and L has the following meaning: 
       
    
     
       
         
         
             
             
         
       
         
         where the bond marked by * is attached to the amide while the bond marked # is attached to Q; 
       
    
     
       
         
           
               
               
               
               
               
               
               
               
             
               
                 TABLE 1 
               
               
                   
               
               
                   
                   
                   
                   
                   
                   
                   
                 Mass 
               
               
                 Ex.  
                 Hal 
                 T 
                 L 
                 R 1   
                 Q 
                 logP 
                 (M + H) 
               
               
                   
               
             
            
               
                  1 
                 Cl 
                 O 
                 L-1 
                 H 
                 3-methylbutyl  
                 3.74 
                 362 
               
               
                  2 
                 Cl 
                 O 
                 L-1 
                 H 
                 pentan-2-yl 
                 3.70 
                 362 
               
               
                  3 
                 Cl 
                 O 
                 L-1 
                 H 
                 4-methylpentan-2-yl 
                 4.19 
                 376 
               
               
                  4 
                 F 
                 O 
                 L-1 
                 H 
                 4-methylpentan-2-yl 
                 3.94 
                 360 
               
               
                  5 
                 Cl 
                 O 
                 L-1 
                 H 
                 2-ethylbutyl 
                 4.03 
                 376 
               
               
                  6 
                 Cl 
                 O 
                 L-1 
                 H 
                 3,3-dimethylbutyl 
                 4.01 
                 376 
               
               
                  7 
                 Cl 
                 O 
                 L-1 
                 H 
                 2-hexyl 
                 4.25 
                 376 
               
               
                  8 
                 Cl 
                 O 
                 L-1 
                 H 
                 hexan-2-yl 
                 4.13 
                 376 
               
               
                  9 
                 Cl 
                 O 
                 L-1 
                 H 
                 2-methylpentan-3-yl 
                 4.07 
                 376 
               
               
                 10 
                 Cl 
                 O 
                 L-1 
                 H 
                 3-methylpentan-2-yl 
                 3.99 
                 376 
               
               
                 11 
                 Cl 
                 O 
                 L-1 
                 H 
                 5-cyanopentan-2-yl 
                 2.57 
                 387 
               
               
                 12 
                 Cl 
                 O 
                 L-1 
                 H 
                 cyclohexylmethyl 
                 4.27 
                 388 
               
               
                 13 
                 Cl 
                 O 
                 L-1 
                 H 
                 2,3-dimethylpentyl 
                 4.41 
                 390 
               
               
                 14 
                 Cl 
                 O 
                 L-1 
                 H 
                 heptan-4-yl 
                 4.54 
                 390 
               
               
                 15 
                 Cl 
                 O 
                 L-1 
                 H 
                 5-methylhexan-3-yl 
                 4.46 
                 390 
               
               
                 16 
                 Cl 
                 O 
                 L-1 
                 H 
                 5-methylhexan-2-yl 
                 4.45 
                 390 
               
               
                 17 
                 Cl 
                 O 
                 L-1 
                 H 
                 4,4-dimethylpentan-2-yl  
                 4.29 
                 390 
               
               
                 18 
                 Cl 
                 O 
                 L-1 
                 H 
                 2-(trimethylsilyl)ethyl 
                 4.30 
                   
               
               
                 19 
                 F 
                 O 
                 L-1 
                 H 
                 2-(trimethylsilyl)ethyl 
                 4.06 
                   
               
               
                 20 
                 F 
                 S 
                 L-1 
                 H 
                 2-(trimethylsilyl)ethyl 
                 4.46 
                 392 
               
               
                 21 
                 Cl 
                 O 
                 L-1 
                 H 
                 1-cyclohexylethyl 
                 4.56 
                 402 
               
               
                 22 
                 Cl 
                 O 
                 L-1 
                 H 
                 pent-2-en-2-yl 
                 3.71 + 
                 360 
               
               
                   
                   
                   
                   
                   
                   
                 3.87  (1)   
                   
               
               
                 23 
                 Cl 
                 O 
                 L-1 
                 H 
                 3,3-dimethylbut-1-en- 
                 3.92 
                 374 
               
               
                   
                   
                   
                   
                   
                 1-yl 
                   
                   
               
               
                 24 
                 Cl 
                 O 
                 L-1 
                 H 
                 2-ethylbut-1-en-1-yl 
                 4.06 
                 374 
               
               
                 25 
                 Cl 
                 O 
                 L-1 
                 H 
                 hex-1-en-1-yl 
                 4.12 
                 374 
               
               
                 26 
                 Cl 
                 O 
                 L-1 
                 H 
                 hex-2-en-2-yl 
                 4.14 + 
                 374 
               
               
                   
                   
                   
                   
                   
                   
                 4.27  (1)   
                   
               
               
                 27 
                 Cl 
                 O 
                 L-1 
                 H 
                 4-methylpent-2-en-3-yl 
                 4.26 
                 374 
               
               
                 28 
                 Cl 
                 O 
                 L-1 
                 H 
                 3-methylpent-2-en-2-yl 
                 4.23 
                 374 
               
               
                 29 
                 Cl 
                 O 
                 L-1 
                 H 
                 5-cyanopent-2-en-2-yl 
                 2.58 + 
                 385 
               
               
                   
                   
                   
                   
                   
                   
                 2.70  (1)   
                   
               
               
                 30 
                 Cl 
                 O 
                 L-1 
                 H 
                 cyclohexylidenemethyl 
                 4.25 
                 386 
               
               
                 31 
                 Cl 
                 O 
                 L-1 
                 H 
                 2,3-dimethylpent-1-en-  
                 4.41 
                 388 
               
               
                   
                   
                   
                   
                   
                 1-yl 
                   
                   
               
               
                 32 
                 Cl 
                 O 
                 L-1 
                 H 
                 hept-3-en-4-yl 
                 4.58 + 
                 388 
               
               
                   
                   
                   
                   
                   
                   
                 4.74  (1)   
                   
               
               
                 33 
                 Cl 
                 O 
                 L-1 
                 H 
                 4,4-dimethylpent-2-en- 
                 4.43 + 
                 388 
               
               
                   
                   
                   
                   
                   
                 2-yl 
                 4.61  (1)   
                   
               
               
                 34 
                 Cl 
                 O 
                 L-1 
                 H 
                 5-methylhex-2-en-2-yl 
                 4.46 + 
                 388 
               
               
                   
                   
                   
                   
                   
                   
                 4.50  (1)   
                   
               
               
                 35 
                 Cl 
                 O 
                 L-1 
                 H 
                 5-methylhex-3-en-3-yl 
                 4.51 + 
                 388 
               
               
                   
                   
                   
                   
                   
                   
                 4.66  (1)   
                   
               
               
                 36 
                 Cl 
                 O 
                 L-1 
                 H 
                 1-cyclohexylvinyl 
                 4.78 + 
                 400 
               
               
                   
                   
                   
                   
                   
                   
                 5.16  
                   
               
               
                 37 
                 Cl 
                 O 
                 L-1 
                 H 
                 1-phenylprop-1-en-1-yl 
                 3.70 
                 408 
               
               
                 38 
                 F 
                 O 
                 L-1 
                 H 
                 phenyl 
                 3.11 
                 352 
               
               
                 39 
                 F 
                 O 
                 L-2 
                 1-trifluoro 
                 phenyl 
                 4.11 
                 420 
               
               
                   
                   
                   
                   
                 methyl 
                   
                   
                   
               
               
                 40 
                 F 
                 O 
                 L-3 
                 H 
                 4-methylphenyl 
                 3.60 
                 366 
               
               
                 41 
                 F 
                 O 
                 L-4 
                 H 
                 4-chlorophenyl 
                 3.87 
                 386 
               
               
                   
               
               
                 Note 
               
               
                   1  mixture of isomers 
               
            
           
         
       
     
     In table 1, unless otherwise specified, M+H (ApcI+) means the molecular ion peak plus 1 a.m.u. (atomic mass unit) as observed in mass spectroscopy via positive atmospheric pressure chemical ionisation. 
     In table 1, the logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a reversed-phase column (C 18), using the method described below: 
     Temperature: 40° C.; Mobile phases: 0.1% aqueous formic acid and acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile. 
     Calibration was carried out using unbranched alkan-2-ones (comprising 3 to 16 carbon atoms) with known logP values (determination of the logP values by the retention times using linear interpolation between two successive alkanones). lambda-max-values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals. 
     NMR Data of Selected Examples 
     NMR Peak List Method 
     The  1 H-NMR data of selected examples are stated in the form of  1 H-NMR peak lists. For each signal peak, the δ value in ppm and the signal intensity in brackets are listed: 
     Example 3 
       1 H NMR (600 MHz, CD3CN-d) δ ppm: 0.84-0.86 (m, 3H); 1.22-1.23 (m, 2H); 1.44-1.55 (m, 2H); 1.93-1.97 (m, 6H); 2.15 (s, 1H); 3.20-3.24 (m, 1H); 3.90 (s, 2H); 7.10 (t, 1H); 7.28 (s, 1H); 8.03 (b, 1H) 
     Example 4 
       1 H NMR (600 MHz, CD3CN-d) δ ppm: 0.84-0.87 (m, 6H); 1.18-1.27 (m, 2H); 1.41-1.52 (m, 2H); 1.92-1.97 (m, 6H); 2.15 (s, 1H); 3.16-3.34 (m, 1H); 3.79 (s, 2H); 7.10 (t, 1H); 7.14 (s, 1H); 7.82 (b, 1H) 
    
    
     USE EXAMPLES 
     Example A  Alternaria  Test (Tomato)/Preventive 
     
         
         Solvent: 49 parts by weight of N,N-dimethylformamide 
         Emulsifier: 1 part by weight of alkylarylpolyglycolether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 
     To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of  Alternaria solani . The plants remain for one day in an incubation cabinet at approximately 22° C. and a relative atmospheric humidity of 100%. Then the plants are placed in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 96%. 
     The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control while an efficacy of 100% means that no disease is observed. 
     In this test, the following compounds from table A according to the invention, show at an active compound concentration of 500 ppm, an efficacy of 70% or more: 
     
       
         
           
               
               
               
             
               
                   
                 TABLE A 
               
               
                   
                   
               
               
                   
                 Example 
                 Efficacy 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 1 
                 100 
               
               
                   
                 2 
                 94 
               
               
                   
                 3 
                 100 
               
               
                   
                 4 
                 100 
               
               
                   
                 5 
                 100 
               
               
                   
                 6 
                 95 
               
               
                   
                 8 
                 94 
               
               
                   
                 9 
                 94 
               
               
                   
                 12 
                 100 
               
               
                   
                 13 
                 95 
               
               
                   
                 15 
                 88 
               
               
                   
                 16 
                 88 
               
               
                   
                 17 
                 94 
               
               
                   
                 18 
                 80 
               
               
                   
                 19 
                 90 
               
               
                   
                 21 
                 95 
               
               
                   
                 22 
                 94 
               
               
                   
                 23 
                 70 
               
               
                   
                 26 
                 75 
               
               
                   
                 27 
                 75 
               
               
                   
                 28 
                 94 
               
               
                   
                 30 
                 70 
               
               
                   
                 33 
                 88 
               
               
                   
                   
               
            
           
         
       
     
     Example B 
       Sphaerotheca  Test (Cucumber)/Preventive 
     
         
         Solvent: 49 parts by weight of N,N-dimethylformamide 
         Emulsifier: 1 part by weight of alkylarylpolyglycolether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 
     To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of  Sphaerotheca fuliginea . Then the plants are placed in a greenhouse at approximately 23° C. and a relative atmospheric humidity of approximately 70%. 
     The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. 
     In this test, the following compounds from table B according to the invention, show at an active compound concentration of 500 ppm, an efficacy of 85% or more: 
     
       
         
           
               
               
               
             
               
                   
                 TABLE B 
               
               
                   
                   
               
               
                   
                 Example 
                 Efficacy 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 3 
                 96 
               
               
                   
                 4 
                 100 
               
               
                   
                 6 
                 89 
               
               
                   
                 17 
                 100 
               
               
                   
                 18 
                 98 
               
               
                   
                 19 
                 100 
               
               
                   
                   
               
            
           
         
       
     
     Example C 
       Venturia  Test (Apples)/Preventive 
     
         
         Solvent: 24.5 parts by weight of acetone
       24.5 parts by weight of N,N-dimethylformamide   
     
         Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 
     To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the causal agent of apple scab ( Venturia inaequalis ) and then remain for 1 day in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 100%. 
     The plants are then placed in a greenhouse at approximately 21° C. and a relative atmospheric humidity of approximately 90%. 
     The test is evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. 
     In this test, the following compounds from table C according to the invention, show at an active compound concentration of 100 ppm, an efficacy of 90% or more: 
     
       
         
           
               
               
               
             
               
                   
                 TABLE C 
               
               
                   
                   
               
               
                   
                 Example 
                 Efficacy 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 3 
                 100 
               
               
                   
                 4 
                 100 
               
               
                   
                 18 
                 94 
               
               
                   
                 19 
                 99 
               
               
                   
                   
               
            
           
         
       
     
     Example D 
       Uromyces  Test (Beans)/Preventive 
     
         
         Solvent: 24.5 parts by weight of acetone
       24.5 parts by weight of N,N-dimethylformamide   
     
         Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 
     To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causal agent of bean rust ( Uromyces appendiculatus ) and then remain for 1 day in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 100%. 
     The plants are then placed in a greenhouse at approximately 21° C. and a relative atmospheric humidity of approximately 90%. 
     The test is evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. 
     In this test, the following compounds from table D according to the invention, show at an active compound concentration of 100 ppm, a total efficacy: 
     
       
         
           
               
               
               
             
               
                   
                 TABLE D 
               
               
                   
                   
               
               
                   
                 Example 
                 Efficacy 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 3 
                 100 
               
               
                   
                 4 
                 100 
               
               
                   
                 18 
                 100 
               
               
                   
                 19 
                 100 
               
               
                   
                   
               
            
           
         
       
     
     Example E 
       Botrytis  Test (Beans)/Preventive 
     
         
         Solvent: 24.5 parts by weight of acetone
       24.5 parts by weight of N,N-dimethylformamide   
     
         Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 
     To test for preventive activity, young plants are sprayed with the preparation of active compound. After the spray coating has dried on, 2 small pieces of agar covered with growth of  Botrytis cinerea  are placed on each leaf. The inoculated plants are placed in a darkened chamber at 20° C. and a relative atmospheric humidity of 100%. 
     2 days after the inoculation, the size of the lesions on the leaves is evaluated. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. 
     In this test, the following compounds from table E according to the invention, show at an active compound concentration of 100 ppm, an efficacy of 90% or more: 
     
       
         
           
               
               
               
             
               
                   
                 TABLE E 
               
               
                   
                   
               
               
                   
                 Example 
                 Efficacy 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 3 
                 98 
               
               
                   
                 4 
                 97 
               
               
                   
                 18 
                 91 
               
               
                   
                 19 
                 100 
               
               
                   
                   
               
            
           
         
       
     
     Example F 
       Blumeria  Test (Barley)/Preventive 
     
         
         Solvent: 49 parts by weight of N,N-dimethylacetamid 
         Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 
     To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are dusted with spores of  Blumeria graminis  f.sp.  hordei.    
     The plants are placed in the greenhouse at a temperature of approximately 18° C. and a relative atmospheric humidity of approximately 80% to promote the development of mildew pustules. 
     The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. 
     In this test, the following compounds from table F according to the invention, show at an active compound concentration of 500 ppm, an efficacy of 90% or more: 
     
       
         
           
               
               
               
             
               
                   
                 TABLE F 
               
               
                   
                   
               
               
                   
                 Example 
                 Efficacy 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 1 
                 94 
               
               
                   
                 3 
                 100 
               
               
                   
                 4 
                 100 
               
               
                   
                 6 
                 94 
               
               
                   
                 12 
                 94 
               
               
                   
                 13 
                 100 
               
               
                   
                 15 
                 94 
               
               
                   
                 18 
                 92 
               
               
                   
                 19 
                 100 
               
               
                   
                   
               
            
           
         
       
     
     Example G 
       Fusarium nivale  (Var.  Majus )-Test (Wheat)/Preventive 
     
         
         Solvent: 49 parts by weight of N,N-dimethylacetamide 
         Emulsifier: 1 part by weight of alkylaryl polyglycol ether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 
     To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. 
     After the spray coating has been dried, the plants are slightly injured by using a sandblast and afterwards they are sprayed with a conidia suspension of  Fusarium nivale  (var.  majus ). 
     The plants are placed in the greenhouse under a translucent incubation cabinet at a temperature of approximately 10° C. and a relative atmospheric humidity of approximately 100%. 
     The test is evaluated 5 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. 
     In this test, the following compounds from table G according to the invention, show at an active compound concentration of 500 ppm, an efficacy of 80% or more: 
     
       
         
           
               
               
               
             
               
                   
                 TABLE G 
               
               
                   
                   
               
               
                   
                 Example 
                 Efficacy 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 1 
                 80 
               
               
                   
                 3 
                 100 
               
               
                   
                 6 
                 100 
               
               
                   
                 7 
                 90 
               
               
                   
                 13 
                 100 
               
               
                   
                 18 
                 100 
               
               
                   
                 19 
                 100 
               
               
                   
                   
               
            
           
         
       
     
     Under the same conditions, high (at least 80%) protection to total protection is observed at a dose of 250 ppm and 500 ppm of active ingredient with compound 3, whereas poor (less than 15%) protection to average (less than 50%) protection is observed with the compound of example 1.13 disclosed in patent application EP-0737682 as in table G2. 
     
       
         
           
               
               
               
               
             
               
                   
                 TABLE G2 
               
               
                   
                   
               
               
                   
                 Example 
                 dose (ppm) 
                 Efficacy 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
            
               
                   
                 3 from this invention 
                 500 
                 100 
               
               
                   
                   
                 250 
                 86 
               
               
                   
                 1.13 from EP-0737682 
                 500 
                 43 
               
               
                   
                   
                 250 
                 14 
               
               
                   
                   
               
            
           
         
       
     
     Example 1.13 disclosed in international patent EP-0737682 corresponds to 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide [commun name: penthiopyrad]. 
     These results show that the compounds according to the invention have a better biological activity than the structurally closest compounds disclosed in EP-0737682. 
     Example H 
       Puccinia  Test (Wheat)/Preventive 
     
         
         Solvent: 49 parts by weight of N,N-dimethylformamide 
         Emulsifier: 1 part by weight of alkylarylpolyglycolether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 
     To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of  Puccinia recondita . The plants remain for 48 hours in an incubation cabinet at 22° C. and a relative atmospheric humidity of 100%. Then the plants are placed in a greenhouse at a temperature of approximately 20° C. and a relative atmospheric humidity of approximately 80%. 
     The test is evaluated 7-9 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control while an efficacy of 100% means that no disease is observed. 
     In this test, the following compounds from table H according to the invention, show at an active compound concentration of 500 ppm, an efficacy of 70% or more: 
     
       
         
           
               
               
               
             
               
                   
                 TABLE H 
               
               
                   
                   
               
               
                   
                 Example 
                 Efficacy 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 1 
                 95 
               
               
                   
                 2 
                 100 
               
               
                   
                 3 
                 100 
               
               
                   
                 4 
                 100 
               
               
                   
                 5 
                 90 
               
               
                   
                 6 
                 100 
               
               
                   
                 7 
                 100 
               
               
                   
                 8 
                 95 
               
               
                   
                 9 
                 80 
               
               
                   
                 10 
                 90 
               
               
                   
                 11 
                 100 
               
               
                   
                 12 
                 95 
               
               
                   
                 13 
                 90 
               
               
                   
                 14 
                 70 
               
               
                   
                 15 
                 90 
               
               
                   
                 16 
                 100 
               
               
                   
                 17 
                 100 
               
               
                   
                 18 
                 100 
               
               
                   
                 19 
                 100 
               
               
                   
                 21 
                 95 
               
               
                   
                 22 
                 80 
               
               
                   
                 23 
                 90 
               
               
                   
                 24 
                 90 
               
               
                   
                 27 
                 80 
               
               
                   
                 28 
                 80 
               
               
                   
                 32 
                 80 
               
               
                   
                 33 
                 95 
               
               
                   
                 36 
                 80 
               
               
                   
                   
               
            
           
         
       
     
     Example I 
       Pyrenophora  Test (Barley)/Preventive 
     
         
         Solvent: 49 parts by weight of N,N-dimethylformamide 
         Emulsifier: 1 part by weight of alkylarylpolyglycolether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 
     To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after this treatment, the plants are inoculated with an aqueous spore suspension of  Pyrenophora teres . The plants remain for 48 hours in an incubation cabinet at 22° C. and a relative atmospheric humidity of 100%. Then the plants are placed in a greenhouse at a temperature of approximately 20° C. and a relative atmospheric humidity of approximately 80%. 
     The test is evaluated 7-9 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control while an efficacy of 100% means that no disease is observed. 
     In this test, the following compounds from table I according to the invention, show at an active compound concentration of 500 ppm, an efficacy of 70% or more: 
     
       
         
           
               
               
               
             
               
                   
                 TABLE I 
               
               
                   
                   
               
               
                   
                 Example 
                 Efficacy 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 1 
                 100 
               
               
                   
                 2 
                 100 
               
               
                   
                 3 
                 100 
               
               
                   
                 4 
                 100 
               
               
                   
                 5 
                 100 
               
               
                   
                 6 
                 100 
               
               
                   
                 7 
                 95 
               
               
                   
                 8 
                 100 
               
               
                   
                 9 
                 100 
               
               
                   
                 10 
                 100 
               
               
                   
                 11 
                 94 
               
               
                   
                 12 
                 100 
               
               
                   
                 13 
                 100 
               
               
                   
                 14 
                 94 
               
               
                   
                 15 
                 100 
               
               
                   
                 16 
                 94 
               
               
                   
                 17 
                 94 
               
               
                   
                 18 
                 100 
               
               
                   
                 19 
                 100 
               
               
                   
                 21 
                 100 
               
               
                   
                 22 
                 94 
               
               
                   
                 23 
                 80 
               
               
                   
                 24 
                 90 
               
               
                   
                 26 
                 89 
               
               
                   
                 27 
                 89 
               
               
                   
                 28 
                 100 
               
               
                   
                 30 
                 80 
               
               
                   
                 31 
                 70 
               
               
                   
                 33 
                 94 
               
               
                   
                 34 
                 78 
               
               
                   
                 36 
                 95 
               
               
                   
                   
               
            
           
         
       
     
     Example J 
       Pyricularia  Test (Rice)/Protective 
     
         
         Solvent: 28.5 parts by weight of acetone 
         Emulsifier: 1.5 part by weight of alkylaryl polyglycol ether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water and the stated amount of emulsifier to the desired concentration. 
     To test for protective activity, young rice plants are sprayed with the preparation of active compound at the stated application rate. 1 day after the treatment, the plants are inoculated with an aqueous spore suspension of  Pyricularia oryzae . The plants are then placed in a greenhouse at a relative atmospheric humidity of 100% and a temperature of 25° C. 
     Evaluation is carried out 5 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. 
     In this test, the following compound according to the invention, show at an active compound concentration of 250 ppm, an efficacy of 95% or more: 
     Example no. 3 (97%). 
     Example K 
       Rhizoctonia  Test (Rice)/Protective 
     
         
         Solvent: 28.5 parts by weight of acetone 
         Emulsifier: 1.5 part by weight of alkylaryl polyglycol ether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water and the stated amount of emulsifier to the desired concentration. 
     To test for protective activity, young rice plants are sprayed with the preparation of active compound at the stated application rate. 1 day after the treatment, the plants are inoculated with hyphae of  Rhizoctonia solani . The plants are then placed in a greenhouse at a relative atmospheric humidity of 100% and a temperature of 25° C. 
     Evaluation is carried out 4 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. 
     In this test, the following compound according to the invention, show at an active compound concentration of 250 ppm, an efficacy of 95% or more: 
     Example no. 3 (100%). 
     Example L 
       Cochliobolus  Test (Rice)/Protective 
     
         
         Solvent: 28.5 parts by weight of acetone 
         Emulsifier: 1.5 part by weight of alkylaryl polyglycol ether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water and the stated amount of emulsifier to the desired concentration. 
     To test for protective activity, young rice plants are sprayed with the preparation of active compound at the stated application rate. 1 day after the treatment, the plants are inoculated with an aqueous spore suspension of  Cochliobolus miyabeanus . The plants are then placed in a greenhouse at a relative atmospheric humidity of 100% and a temperature of 25° C. 
     Evaluation is carried out 4 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed. 
     In this test, the following compound according to the invention, show at an active compound concentration of 250 ppm, an efficacy of 95% or more: 
     Example no. 3 (97%). 
     Example M 
       Phakopsora  Test (Soybeans)/Protective 
     
         
         Solvent: 28.5 parts by weight of acetone 
         Emulsifier: 1.5 parts by weight of polyoxyethylene alkyl phenyl ether 
       
    
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 
     To test for protective activity, young plants are sprayed with the preparation of active compound at the stated rate of application. One day after spraying, the plants are inoculated with an aqueous spore suspension of the causal agent of soybean rust ( Phakopsora pachyrhizi ). The plants are then placed in a greenhouse at approximately 20° C. and a relative atmospheric humidity of approximately 80%. 
     The test is evaluated 11 days after the inoculation. 0% means an efficacy which corresponds to that of the control, while an efficacy of 100% means that no disease is observed. 
     In this test, the following compounds from table M according to the invention, show at an active compound concentration of 250 ppm, an efficacy of 95% or more: 
     
       
         
           
               
               
               
             
               
                   
                 TABLE M 
               
               
                   
                   
               
               
                   
                 Example 
                 Efficacy 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
            
               
                   
                 3 
                 98 
               
               
                   
                 4 
                 99