Fungicidal N-(Phenylcycloalkyl)carboxamide, N-(Benzylcycloalkyl)carboxamide and thiocarboxamide derivatives
View Patent ↗The present invention relates to a N-(Phenylcycloalkyl)carboxamide or N-(Benzylcycloalkyl)carboxamide or its thiocarboxamide derivative of formula (I) wherein A represents a carbo-linked, unsaturated or partially saturated, substituted or non-substituted 5-membered heterocyclyl group, T represents an oxygen or a sulphur atom, B represents a non aromatic carbocycle that can be substituted by one to four C 1 -C 8 -alkyl groups, and X, Z 1 , Z 2 and Z 3 represent various substituents; their process of preparation; the preparation of intermediate compounds; their use as fungicide active agents, particularly in the form of fungicide compositions and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.
1. A compound of formula (I)
wherein
A is a carbo-linked, unsaturated or partially saturated, 5-membered heterocyclyl group that can be substituted by up to four groups R;
T is O or S;
B is a 3-, 4-, 5-, 6- or 7-membered non aromatic carbocycle that can be substituted by up to four C 1 -C 8 -alkyl groups;
n is 0, 1, 2, 3, 4 or 5;
m is 0 or 1;
each X is independently selected from the group consisting of 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 5 halogen atoms; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl having 1 to 5 halogen atoms; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfinyl; C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 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 5 halogen atoms; substituted or non-substituted C 3 -C 8 -alkynyloxy; C 2 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms; substituted or non-substituted C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogenocycloalkyl having 1 to 5 halogen atoms; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 1 -C 8 -alkyl; 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 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbonylamino; C 1 -C 8 -halogenoalkyl-carbonylamino having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkyloxycarbonyloxy; C 1 -C 8 -halogenoalkoxycarbonyloxy having 1 to 5 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; C 1 -C 8 -arylalkyl that can be substituted by up to 6 groups Q; C 2 -C 8 -arylalkenyl that can be substituted by up to 6 groups Q; C 2 -C 8 -arylalkynyl that can be substituted by up to 6 groups Q; aryloxy that can be substituted by up to 6 groups Q; arylsulfanyl that can be substituted by up to 6 groups Q; arylamino that can be substituted by up to 6 groups Q; C 1 -C 8 -arylalkyloxy that can be substituted by up to 6 groups Q; C 1 -C 8 -arylalkylsulfanyl that can be substituted by up to 6 groups Q; and C 1 -C 8 -arylalkylamino that can be substituted by up to 6 groups Q; or
two substituents X together with the consecutive carbon atoms to which they are linked can form a 5- or 6-membered, saturated carbocycle or 5- or 6-membered, saturated heterocycle, which can be substituted by up to four groups Q which can be the same or different;
Z 1 and Z 2 are independently selected from the group consisting of a hydrogen atom; a halogen atom; cyano; a substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; and substituted or non-substituted C 1 -C 8 -alkoxycarbonyl;
Z 3 is a non-substituted C 3 -C 7 -cycloalkyl or a C 3 -C 7 -cycloalkyl substituted by up to 10 substituents independently selected from the group consisting of halogen atoms, cyano, C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkylaminocarbonyl and di-C 1 -C 8 -alkylamino-carbonyl;
Z 4 and Z 5 are independently selected from the group consisting of a hydrogen atom; a halogen atom; cyano; a substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; or Z 4 and Z 5 comprise a C 2 -C 5 -alkylene group that can be substituted by up to four C 1 -C 8 -alkyl groups;
each Q is independently selected from the group consisting of a halogen atom; cyano; nitro; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 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 having 1 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 having 1 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; and substituted or non-substituted (benzyloxyimino)-C 1 -C 8 -alkyl;
each R is independently selected from the group consisting of hydrogen atom; halogen atom; nitro; cyano; hydroxy; amino; sulfanyl; pentafluoro-λ 6 -sulfanyl; substituted or non-substituted (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (benzyloxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl having 1 to 5 halogen atoms; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfinyl; C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 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; substituted or non-substituted C 3 -C 8 -alkynyloxy; substituted or non-substituted C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogenocycloalkyl having 1 to 5 halogen atoms; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl; substituted or non-substituted C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 halogenoalkoxycarbonyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted di-C 1 -C 8 -alkylcarbamoyl; phenoxy; phenylsulfanyl; phenylamino; benzyloxy; benzylsulfanyl; ear and benzylamino;
as well as any salt, N-oxide, or optically active isomer thereof.
2. The compound of claim 1 wherein A is selected from the group consisting of:
a heterocycle of formula (A 1 )
wherein:
R 1 , R 2 , and R 3 are independently selected from the group consisting of a hydrogen atom; a halogen atom;
substituted or non-substituted C 1 -C 5 -alkyl; 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, and C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 2 )
wherein:
R 4 , R 5 , and R 6 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; 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, and C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 3 )
wherein:
R 7 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; 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, and C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
R 8 is selected from the group consisting of a hydrogen atom and a substituted or non-substituted C 1 -C 5 -alkyl;
a heterocycle of formula (A 4 )
wherein:
R 9 , R 10 , and R 11 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; amino; 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 and C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 5 )
wherein:
R 12 and R 13 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 1 -C 5 -alkoxy; amino; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different and C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
R 14 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 1 -C 5 -alkoxy; amino; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different and C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A 6 )
wherein:
R 15 is selected from the group consisting of a hydrogen atom; a halogen atom; a cyano; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 1 -C 5 -alkoxy; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 16 and R 18 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkoxycarbonyl; substituted or non-substituted C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 17 is selected from the group consisting of a hydrogen atom and substituted or non-substituted C 1 -C 5 -alkyl;
a heterocycle of formula (A 7 )
wherein:
R 19 is selected from the group consisting of a hydrogen atom and a C 1 -C 5 -alkyl
R 20 , R 21 , and R 22 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 8 )
wherein:
R 23 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 24 is selected from the group consisting of a hydrogen atom or substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 9 )
wherein:
R 25 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 26 is selected from the group consisting of a hydrogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 10 )
wherein:
R 27 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 28 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; 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 and substituted or non-substituted di(C 1 -C 5 -alkyl)amino;
a heterocycle of formula (A 11 )
wherein:
R 29 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 1 -C 5 -alkoxy; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 30 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; 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 and substituted or non-substituted di(C 1 -C 5 -alkyl)amino;
a heterocycle of formula (A 12 )
wherein:
R 31 is selected from the group consisting of a hydrogen atom and a substituted or non-substituted C 1 -C 5 -alkyl
R 32 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 33 is selected from the group consisting of a hydrogen atom; a halogen atom; a nitro; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 1 -C 5 -alkoxy; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 13 )
wherein:
R 34 is selected from the group consisting of 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 and C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
R 35 is selected from the group consisting of 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 and substituted or non-substituted di(C 1 -C 5 -alkyl)amino;
R 36 is selected from the group consisting of a hydrogen atom and substituted or non-substituted C 1 -C 5 -alkyl;
a heterocycle of formula (A 14 )
wherein:
R 37 and R 38 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 ; 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 and a substituted or non-substituted C 1 -C 5 -alkylsulfanyl;
R 39 is selected from the group consisting of a hydrogen atom and substituted or non-substituted C 1 -C 5 -alkyl;
a heterocycle of formula (A 15 )
wherein:
R 40 and R 41 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 16 )
wherein:
R 42 and R 43 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or amino;
a heterocycle of formula (A 17 )
wherein:
R 44 and R 45 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 18 )
wherein:
R 47 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 46 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different and substituted or non-substituted C 1 -C 5 -alkylsulfanyl;
a heterocycle of formula (A 19 )
wherein:
R 49 and R 48 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 1 -C 5 -alkoxy; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 20 )
wherein:
R 50 and R 51 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 1 -C 5 -alkoxy; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 21 )
wherein:
R 52 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 22 )
wherein:
R 53 is selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 23 )
wherein:
R 54 and R 56 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 55 is selected from the group consisting of a hydrogen atom and substituted or non-substituted C 1 -C 5 -alkyl;
a heterocycle of formula (A 24 )
wherein:
R 57 and R 59 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 58 is selected from the group consisting of a hydrogen atom and substituted or non-substituted C 1 -C 5 -alkyl;
a heterocycle of formula (A 25 )
wherein:
R 60 and R 61 are independently selected from the group consisting of a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl and C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 62 is selected from the group consisting of a hydrogen atom and substituted or non-substituted C 1 -C 5 -alkyl; and
a heterocycle of formula (A 26 )
wherein:
R 65 is selected from the group consisting of 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 and C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
R 63 is selected from the group consisting of 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 and di(C 1 -C 5 -alkyl)amino;
R 64 is selected from the group consisting of a hydrogen atom and substituted or non-substituted C 1 -C 5 -alkyl.
3. The compound of claim 2 wherein A is selected from the group consisting of A 2 ; A 6 ; A 10 and A 13 .
4. The compound of claim 3 wherein
A is A 13
wherein
R 34 is selected from the group consisting of a substituted or non-substituted C 1 -C 5 -alkyl, C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; and substituted or non-substituted C 1 -C 5 -alkoxy;
R 35 is selected from the group consisting of a hydrogen atom and a halogen atom and
R 36 is a substituted or non-substituted C 1 -C 5 -alkyl.
5. The compound of claim 1 wherein T is O.
6. The compound of claim 1 wherein n is 0, 1 or 2.
7. The compound of claim 1 wherein B is a 3-, 5-, 6- or 7-membered non aromatic carbocycle that can be substituted by one to four C 1 -C 8 -alkyl groups.
8. The compound of claim 7 wherein B is selected from the group consisting of cyclopropyl, cyclopentyl, cyclohexyl and cycloheptyl carbocycles that can be substituted by one to four methyl groups.
9. The compound of claim 1 wherein each X is independently selected from the group consisting of a halogen atom; 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 tri(C 1 -C 8 -alkyl)silyl; substituted or non-substituted C 1 -C 8 -alkoxy and C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
or wherein two consecutive substituents X together with the phenyl ring form a substituted or non substituted moiety selected from the group consisting of 1,3-benzodioxolyl;
1,2,3,4-tetrahydro-quinoxalinyl; 3,4-dihydro-2H-1,4-benzoxazinyl; 1,4-benzodioxanyl; indanyl; 2,3-dihydrobenzofuranyl; and indolinyl.
10. The compound of claim 1 wherein Z 1 and Z 2 are independently selected from the group consisting of a hydrogen atom and a substituted or non-substituted C 1 -C 8 -alkyl.
11. The compound of claim 1 wherein Z 3 is selected from the group consisting of a non-substituted C 3 -C 7 cycloalkyl and a C 3 -C 7 cycloalkyl substituted by up to 10 substituents independently selected from the group consisting of halogen atoms, C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkoxy and C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different.
12. The compound of claim 1 wherein Z 3 is a non-substituted C 3 -C 7 -cycloalkyl.
13. The compound of claim 1 wherein Z 4 and Z 5 are independently selected from the group consisting of a hydrogen atom, a halogen atom and a substituted or non-substituted C 1 -C 8 -alkyl.
14. The compound of claim 1 wherein each R is independently selected from the group consisting of a hydrogen atom; halogen atom; cyano; substituted or non-substituted C 1 -C 8 -alkylamino; substituted or non-substituted di-C 1 -C 8 -alkylamino; substituted or non-substituted tri(C 1 -C 8 -alkyl)silyl; 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; amino; hydroxyl; nitro; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; and substituted or non-substituted C 2 -C 8 -alkynyloxy.
15. A fungicide composition comprising, as an active ingredient, an effective amount of the compound of claim 1 and an agriculturally acceptable support, carrier or filler.
16. A compound of formula (II)
wherein,
each X is selected from the group consisting of 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 5 halogen atoms; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl having 1 to 5 halogen atoms; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfinyl; C 1 -C 8 -halogenoalkylsulfinyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; C 1 -C 8 -halogenoalkylsulfonyl having 1 to 5 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 5 halogen atoms; substituted or non-substituted C 3 -C 8 -alkynyloxy; C 2 -C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms; substituted or non-substituted C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogenocycloalkyl having 1 to 5 halogen atoms; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 1 -C 8 -alkyl; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 1 -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 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbonyloxy; C 1 -C 8 -halogenoalkylcarbonyloxy having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbonylamino; C 1 -C 8 -halogenoalkyl-carbonylamino having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkyloxycarbonyloxy; C 1 -C 8 -halogenoalkoxycarbonyloxy having 1 to 5 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; C 1 -C 8 -arylalkyl that can be substituted by up to 6 groups Q; C 2 -C 8 -arylalkenyl that can be substituted by up to 6 groups Q; C 2 -C 8 -arylalkynyl that can be substituted by up to 6 groups Q; aryloxy that can be substituted by up to 6 groups Q arylsulfanyl that can be substituted by up to 6 groups Q; arylamino that can be substituted by up to 6 groups Q; C 1 -C 8 -arylalkyloxy that can be substituted by up to 6 groups Q; C 1 -C 8 -arylalkylsulfanyl that can be substituted by up to 6 groups Q; and C 1 -C 8 -arylalkylamino that can be substituted by up to 6 groups Q;
n is 0, 1, 2, 3, 4 or 5;
m is 0 or 1;
or two substituents X together with the consecutive carbon atoms to which they are linked can form a 5- or 6-membered, saturated carbocycle or saturated heterocycle, which can be substituted by up to four groups Q that can be the same or different;
Z 1 and Z 2 are independently selected from the group consisting of a hydrogen atom; a halogen atom; cyano; a substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; and substituted or non-substituted C 1 -C 8 -alkoxycarbonyl;
Z 3 is selected from the group consisting of a non-substituted C 3 -C 7 -cycloalkyl and a C 3 -C 7 -cycloalkyl substituted by up to 10 substituents independently selected from the group consisting of halogen atoms, cyano, C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkylaminocarbonyl and di-C 1 -C 8 -alkylamino-carbonyl;
Z 4 and Z 5 are independently selected from the group consisting of a hydrogen atom; a halogen atom; cyano; a substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; and substituted or non-substituted C 1 -C 8 -alkoxycarbonyl;
or Z 4 and Z 5 are a C 2 -C 5 -alkylene group that can be substituted by one to four C 1 -C 8 -alkyl groups;
each Q is independently selected from the group consisting of a halogen atom; cyano; nitro; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 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 having 1 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 having 1 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; and substituted or non-substituted (benzyloxyimino)-C 1 -C 8 -alkyl; and
B is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl moieties with the exclusion of N-cyclopropyl-2-phenylcyclohexanamine.
17. A method for controlling phytopathogenic fungi of crops comprising applying an agronomically effective and substantially non-phytotoxic quantity of the compound of claim 1 to the soil where plants grow or are capable of growing, to the leaves and/or the fruit of plants or to the seeds of plants.
18. A method for controlling phytopathogenic fungi of crops comprising applying an agronomically effective and substantially non-phytotoxic quantity of the composition of claim 15 to the soil where plants grow or are capable of growing, to the leaves and/or the fruit of plants or to the seeds of plants.
19. The compound of claim 12 wherein Z 3 is non-substituted cyclopropyl.