N-cycloalkyl-n-[(heterocyclylphenyl)methylene]-(thio)carboxamide derivatives

Abstract

The present invention relates to fungicidal N-cycloalkyl-N-[(heterocyclylphenyl)methylene] carboxamide derivatives and their thiocarbonyl derivatives, their process of preparation and intermediate compounds for their preparation, their use as fungicides; particularly in the form of fungicidal compositions and methods for the control of phytopathogenic fungi of plants using these compounds or their compositions.

1 - 15 . (canceled) 
     
     
         16 : A compound of formula (IIa) 
       
         
           
           
               
               
           
         
       
       wherein
 Z 2  and Z 3 , which can be the same or different, are a hydrogen atom; non-substituted C 1 -C 8 -alkyl; non-substituted C 2 -C 8 -alkenyl; non-substituted C 2 -C 8 -alkynyl; a halogen atom; non-substituted C 1 -C 8 -alkoxy; non-substituted C 2 -C 8 -alkenyloxy; or non-substituted C 2 -C 8 -alkynyloxy; 
 n is 0, 1, 2, 3 or 4; 
 each X is independently a halogen atom; nitro; cyano; isonitrile; hydroxy; amino; sulfanyl; pentafluoro-λ 6 -sulfanyl; formyl; formyloxy; formylamino; substituted or non-substituted (hydroxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (C 2 -C 8 -alkenyloxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (C 2 -C 8 -alkynyloxyimino)-C 1 -C 8 -alkyl substituted or non-substituted (benzyloxyimino)-C 1 -C 8 -alkyl; carboxy; carbamoyl; N-hydroxycarbamoyl; carbamate; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 9 halogen atoms; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl having 1 to 9 halogen atoms; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfinyl; C 1 -C 8 -halogenoalkylsulfinyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; C 1 -C 8 -halogenoalkylsulfonyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylamino; substituted or non-substituted di-C 1 -C 8 -alkylamino; substituted or non-substituted C 2 -C 8 -alkenyloxy; C 2 -C 8 -halogenoalkenyloxy having 1 to 9 halogen atoms; substituted or non-substituted C 3 -C 8 -alkynyloxy; C 2 -C 8 -halogenoalkynyloxy having 1 to 9 halogen atoms; substituted or non-substituted C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogenocycloalkyl having 1 to 9 halogen atoms; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 1 -C 8 -alkyl; substituted or non-substituted C 4 -C 7 -cycloalkenyl; C 4 -C 7 -halogenocycloalkenyl having 1 to 9 halogen atoms; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 2 -C 8 -alkenyl; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 2 -C 8 -alkynyl; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl; substituted or non-substituted C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbonylamino; C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkyloxycarbonyloxy; C 1 -C 8 -halogenoalkoxycarbonyloxy having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted di-C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted C 1 -C 8 -alkylaminocarbonyloxy; substituted or non-substituted di-C 1 -C 8 -alkylaminocarbonyloxy; substituted or non-substituted N—(C 1 -C 8 -alkyl)hydroxy carbamoyl; substituted or non-substituted C 1 -C 8 -alkoxycarbamoyl; substituted or non-substituted N—(C 1 -C 8 -alkyl)-C 1 -C 8 -alkoxycarbamoyl; aryl that can be substituted by up to 6 groups Q which can be the same or different aryl-C 1 -C 8 -alkyl that can be substituted by up to 6 groups Q which can be the same or different aryl-C 2 -C 8 -alkenyl that can be substituted by up to 6 groups Q which can be the same or different aryl-C 2 -C 8 -alkynyl that can be substituted by up to 6 groups Q which can be the same or different aryloxy that can be substituted by up to 6 groups Q which can be the same or different arylsulfanyl that can be substituted by up to 6 groups Q which can be the same or different arylamino that can be substituted by up to 6 groups Q which can be the same or different aryl-C 1 -C 8 -alkyloxy that can be substituted by up to 6 groups Q which can be the same or different aryl-C 1 -C 8 -alkylsulfanyl that can be substituted by up to 6 groups Q which can be the same or different aryl-C 1 -C 8 -alkylamino that can be substituted by up to 6 groups Q which can be the same or different pyridinyl which can be substituted by up to 4 groups Q, or pyridinyloxy which can be substituted by up to 4 groups Q; 
 each Q is independently a halogen atom, cyano, nitro, substituted or non-substituted C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, substituted or non-substituted C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different, substituted or non-substituted C 1 -C 8 -alkylsulfanyl, C 1 -C 8 -halogenoalkylsulfanyl comprising up to 9 halogen atoms that can be the same or different, substituted or non-substituted tri(C 1 -C 8 )alkylsilyl, substituted or non-substituted tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl, substituted or non-substituted (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl, or substituted or non-substituted (benzyloxyimino)-C 1 -C 8 -alkyl; 
 L is a direct bond; and 
 B is a substituted or non-substituted oxiranyl ring, a substituted or non-substituted thienyl ring, a substituted or non-substituted benzothienyl ring, a substituted or non-substituted furan ring, or a substituted or non-substituted benzofuran ring, 
 
       providing that (IIa) does not represent:
 N-[2-(2-furyl)benzyl]cyclopropanamine; 
 N-[2-(2-furyl)-4,5-dimethoxybenzyl]cyclopropanamine; 
 N-[2-(3-bromo-2-furyl)-4,5-dimethoxybenzyl]cyclopropanamine; 
 N-[2-(3-bromo-2-furyl)benzyl]cyclopropanamine; 
 N-[2-(3-furyl)benzyl]cyclopropanamine; 
 N-[2-(2-thienyl)benzyl]cyclopropanamine; or 
 N-[4,5-dimethoxy-2-(2-thienyl)benzyl]cyclopropanamine, 
 
       or a salt thereof. 
     
     
         17 : The compound of formula (IIa) according to  claim 16 , selected from the group consisting of:
 N-[5-chloro-2-(2-furyl)benzyl]cyclopropanamine;   N-[5-chloro-2-(2-thienyl)benzyl]cyclopropanamine;   N-[2-(3-thienyl)benzyl]cyclopropanamine;   N-{1-[2-(3-thienyl)phenyl]ethyl}cyclopropanamine;   N-[5-chloro-2-(3-thienyl)benzyl]cyclopropanamine;   N-[2-(5-chloro-2-thienyl)benzyl]cyclopropanamine, and   N-[5-chloro-2-(5-chloro-2-thienyl)benzyl]cyclopropanamine.   
     
     
         18 : A compound of formula (IIb) 
       
         
           
           
               
               
           
         
       
       wherein
 Z 2  and Z 3 , which can be the same or different, are a hydrogen atom; non-substituted C 1 -C 8 -alkyl; non-substituted C 2 -C 8 -alkenyl; non-substituted C 2 -C 8 -alkynyl; a halogen atom; non-substituted C 1 -C 8 -alkoxy; non-substituted C 2 -C 8 -alkenyloxy or non-substituted C 2 -C 8 -alkynyloxy; 
 n is 0, 1, 2, 3 or 4; 
 each X is independently a halogen atom; nitro; cyano; isonitrile; hydroxy; amino; sulfanyl; pentafluoro-λ 6 -sulfanyl; formyl; formyloxy; formylamino; substituted or non-substituted (hydroxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (C 2 -C 8 -alkenyloxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (C 2 -C 8 -alkynyloxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (benzyloxyimino)-C 1 -C 8 -alkyl; carboxy; carbamoyl; N-hydroxycarbamoyl; carbamate; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 9 halogen atoms; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl having 1 to 9 halogen atoms; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfinyl; C 1 -C 8 -halogenoalkylsulfinyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; C 1 -C 8 -halogenoalkylsulfonyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylamino; substituted or non-substituted di-C 1 -C 8 -alkylamino; substituted or non-substituted C 2 -C 8 -alkenyloxy; C 2 -C 8 -halogenoalkenyloxy having 1 to 9 halogen atoms; substituted or non-substituted C 3 -C 8 -alkynyloxy; C 2 -C 8 -halogenoalkynyloxy having 1 to 9 halogen atoms; substituted or non-substituted C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogenocycloalkyl having 1 to 9 halogen atoms; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 1 -C 8 -alkyl; substituted or non-substituted C 4 -C 7 -cycloalkenyl; C 4 -C 7 -halogenocycloalkenyl having 1 to 9 halogen atoms; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 2 -C 8 -alkenyl; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 2 -C 8 -alkynyl; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl; substituted or non-substituted C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbonylamino; C 1 -C 8 -halogenoalkylcarbonylamino having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkyloxycarbonyloxy; C 1 -C 8 -halogenoalkoxycarbonyloxy having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted di-C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted C 1 -C 8 -alkylaminocarbonyloxy; substituted or non-substituted di-C 1 -C 8 -alkylaminocarbonyloxy; substituted or non-substituted N—(C 1 -C 8 -alkyl)hydroxy carbamoyl; substituted or non-substituted C 1 -C 8 -alkoxycarbamoyl; substituted or non-substituted N—(C 1 -C 8 -alkyl)-C 1 -C 8 -alkoxycarbamoyl, aryl that can be substituted by up to 6 groups Q which can be the same or different aryl-C 1 -C 8 -alkyl that can be substituted by up to 6 groups Q which can be the same or different aryl-C 2 -C 8 -alkenyl that can be substituted by up to 6 groups Q which can be the same or different aryl-C 2 -C 8 -alkynyl that can be substituted by up to 6 groups Q which can be the same or different aryloxy that can be substituted by up to 6 groups Q which can be the same or different arylsulfanyl that can be substituted by up to 6 groups Q which can be the same or different arylamino that can be substituted by up to 6 groups Q which can be the same or different aryl-C 1 -C 8 -alkyloxy that can be substituted by up to 6 groups Q which can be the same or different aryl-C 1 -C 8 -alkylsulfanyl that can be substituted by up to 6 groups Q which can be the same or different aryl-C 1 -C 8 -alkylamino that can be substituted by up to 6 groups Q which can be the same or different pyridinyl which can be substituted by up to 4 groups Q, or pyridinyloxy which can be substituted by up to 4 groups Q; 
 each Q is independently a halogen atom, cyano, nitro, substituted or non-substituted C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, substituted or non-substituted C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different, substituted or non-substituted C 1 -C 8 -alkylsulfanyl, C 1 -C 8 -halogenoalkylsulfanyl comprising up to 9 halogen atoms that can be the same or different, substituted or non-substituted tri(C 1 -C 8 )alkylsilyl, substituted or non-substituted tri(C 1 -C 8 )alkylsilyl-C 1 -C 8 -alkyl, substituted or non-substituted (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl, or substituted or non-substituted (benzyloxyimino)-C 1 -C 8 -alkyl; 
 L is a direct bond; and 
 B 1  is a substituted or non-substituted oxiranyl ring, a substituted or non-substituted thienyl ring, a substituted or non-substituted benzothienyl ring, a substituted or non-substituted furan ring, or a substituted or non-substituted benzofuran ring, 
 
       providing that (IIb) does not represent:
 N-[3-(2-furyl)benzyl]cyclopropanamine; 
 N-[5-(2-furyl)-2-methoxybenzyl]cyclopropanamine; 
 N-[4-fluoro-3-(2-furyl)benzyl]cyclopropanamine; 
 N-[2-fluoro-5-(2-furyl)benzyl]cyclopropanamine-; 
 N-[2-fluoro-5-(3-furyl)benzyl]cyclopropanamine; 
 N-[3-(3-bromo-2-furyl)-4-fluorobenzyl]cyclopropanamine; 
 N-[3-(3-bromo-2-furyl)benzyl]cyclopropanamine; 
 N-[5-(3-bromo-2-furyl)-2-fluorobenzyl]cyclopropanamine; 
 N-[5-(3-bromo-2-furyl)-2-methoxybenzyl]cyclopropanamine; 
 N-[3-(3-furyl)benzyl]cyclopropanamine; 
 N-[3-(2-thienyl)benzyl]cyclopropanamine; 
 N-[4-fluoro-3-(2-thienyl)benzyl]cyclopropanamine; 
 N-[2-fluoro-5-(2-thienyl)benzyl]cyclopropanamine-; 
 N-[2-methoxy-5-(2-thienyl)benzyl]cyclopropanamine-; 
 5-{5-[(cyclopropylamino)methyl]-2-fluorophenyl}thiophene-2-carbonitrile, 
 
       or a salt thereof. 
     
     
         19 : The compound of formula (IIb) according to  claim 18 , selected from the group consisting of:
 N-[2-chloro-5-(2-furyl)benzyl]cyclopropanamine;   N-[2-chloro-5-(2-thienyl)benzyl]cyclopropanamine;   N-[2-chloro-5-(3-thienyl)benzyl]cyclopropanamine, and   N-[2-chloro-5-(5-chloro-2-thienyl)benzyl]cyclopropanamine.   
     
     
         20 : A compound of formula (Xa) 
       
         
           
           
               
               
           
         
       
       wherein
 Z 2  and Z 3 , which can be the same or different, are a hydrogen atom; non-substituted C 1 -C 8 -alkyl; non-substituted C 2 -C 8 -alkenyl; non-substituted C 2 -C 8 -alkynyl; a halogen atom; non-substituted C 1 -C 8 -alkoxy; non-substituted C 2 -C 8 -alkenyloxy; or non-substituted C 2 -C 8 -alkynyloxy; 
 A is A 13   
 
       
         
           
           
               
               
           
         
         wherein: 
         R 34  is a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 3 -C 5 -cycloalkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different substituted or non-substituted C 1 -C 5 -alkoxy; substituted or non-substituted C 2 -C 5 -alkynyloxy or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; 
         R 35  is a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; a cyano; substituted or non-substituted C 1 -C 5 -alkoxy; substituted or non-substituted C 1 -C 5 -alkylsulfanyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different amino; substituted or non-substituted C 1 -C 5 -alkylamino or substituted or non-substituted di(C 1 -C 5 -alkyl)amino; 
         R 36  is a hydrogen atom or substituted or non-substituted C 1 -C 5 -alkyl; 
         X a1  is a halogen atom; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; substituted or non-substituted C 3 -C 7 -cycloalkyl; tri(C 1 -C 8 -alkyl)silyl; substituted or non-substituted C 1 -C 8 -alkoxy; or substituted or non-substituted C 1 -C 8 -alkylsulfanyl; 
         X a2  is hydrogen, a halogen atom; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; 
         substituted or non-substituted C 3 -C 7 -cycloalkyl; tri(C 1 -C 8 -alkyl)silyl; substituted or non-substituted C 1 -C 8 -alkoxy; or substituted or non-substituted C 1 -C 8 -alkylsulfanyl, and 
         U 2  is a halogen atom or a triflate group, 
       
       providing that (Xa) does not represent:
 N-(2,5-dichlorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide; 
 N-[1-(2,5-dichlorophenyl)ethyl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide; 
 N-[2-(2,5-dichlorophenyl)propan-2-yl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide; 
 N-[1-(2,5-dichlorophenyl)cyclopropyl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide; 
 5-chloro-N-[1-(2,5-dichlorophenyl)ethyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide; 
 5-chloro-N-[2-(2,5-dichlorophenyl)propan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide; 
 5-chloro-N-[1-(2,5-dichlorophenyl)cyclopropyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide; 
 5-chloro-N-(2,5-dichlorobenzyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide; 
 N-(5-bromo-2-fluorobenzyl)-1,3,5-trimethyl-1H-pyrazole-4-carboxamide; 
 N-(5-bromo-2-fluorobenzyl)-3,5-dimethyl-1H-pyrazole-4-carboxamide; 
 1-methyl-N-[1-(2,4,5-trichlorophenyl)ethyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide; 
 3-(difluoromethyl)-1-methyl-N-[1-(2,4,5-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide; 
 N-(5-chloro-2-fluorobenzyl)-1-methyl-5-propoxy-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide; or 
 N-(2,5-dichlorobenzyl)-1-methyl-5-propoxy-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, 
 
       a salt thereof. 
     
     
         21 : The compound of formula (Xa) according to  claim 20 , selected from the group consisting of:
 N-(5-chloro-2-ethylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide;   N-(5-chloro-2-isopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide;   N-[5-chloro-2-(trifluoromethyl)benzyl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide; and   N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.   
     
     
         22 - 26 . (canceled) 
     
     
         27 : The compound of formula (IIa) according to  claim 16 , wherein Z 2  and Z 3  are independently a hydrogen atom or a methyl. 
     
     
         28 : The compound of formula (IIa) according to  claim 16 , wherein n is 0, 1 or 2. 
     
     
         29 : The compound of formula (IIa) according to  claim 16 , wherein B is a substituted or non-substituted thienyl ring, or a substituted or non-substituted benzothienyl ring. 
     
     
         30 : The compound of formula (IIa) according to  claim 16 , wherein each X is independently a halogen atom; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; substituted or non-substituted C 3 -C 7 -cycloalkyl; tri(C 1 -C 8 -alkyl)silyl; substituted or non-substituted C 1 -C 8 -alkoxy; or substituted or non-substituted C 1 -C 8 -alkylsulfanyl. 
     
     
         31 : The compound of formula (IIb) according to  claim 18 , wherein Z 2  and Z 3  are independently a hydrogen atom or a methyl. 
     
     
         32 : The compound of formula (IIb) according to  claim 18 , wherein n is 0, 1 or 2. 
     
     
         33 : The compound of formula (IIb) according to  claim 18 , wherein B is a substituted or non-substituted thienyl ring, or a substituted or non-substituted benzothienyl ring. 
     
     
         34 : The compound of formula (IIb) according to  claim 18 , wherein each X is independently a halogen atom; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; substituted or non-substituted C 3 -C 7 -cycloalkyl; tri(C 1 -C 8 -alkyl)silyl; substituted or non-substituted C 1 -C 8 -alkoxy; or substituted or non-substituted C 1 -C 8 -alkylsulfanyl. 
     
     
         35 : The compound of formula (Xa) according to  claim 20 , wherein Z 2  and Z 3  are independently a hydrogen atom or a methyl. 
     
     
         36 : The compound of formula (Xa) according to  claim 20 , wherein n is 0, 1 or 2. 
     
     
         37 : The compound of formula (Xa) according to  claim 20 , wherein B is a substituted or non-substituted thienyl ring, or a substituted or non-substituted benzothienyl ring. 
     
     
         38 : The compound of formula (Xa) according to  claim 20 , wherein each X is independently a halogen atom; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms which can be the same or different; substituted or non-substituted C 3 -C 7 -cycloalkyl; tri(C 1 -C 8 -alkyl)silyl; substituted or non-substituted C 1 -C 8 -alkoxy; or substituted or non-substituted C 1 -C 8 -alkylsulfanyl.