Fungicide N-cycloalkyl-N-bicyclic-carboxamide derivatives
View Patent ↗The present invention relates N-cycloalkyl-N-bicyclic-carboxamide, thiocarboxamide or N-substituted carboximidamide derivatives of formula (I) wherein A represents a carbo-linked, 5-membered heterocyclyl group; T represents O, S, N—R a , N—OR a , N—NR a R b or N—CN; Z 1 represents a C 3 -C 7 -cycloalkyl group; X represents N or a CZ 7 and Z 2 ; Z 3 ; L 1 and L 2 represent various substituents; their process of preparation; preparation intermediate compounds; their use as fungicide active agents, particularly in the form of fungicide compositions and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.
1. A compound of formula:
wherein
Z 1 is selected from the group consisting of a nonsubstituted C 3 -C 7 -cycloalkyl and a C 3 -C 7 -cycloalkyl which is substituted by up to 10 atoms or groups, wherein the substituent atoms or groups are 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; di-C 1 -C 8 -alkylaminocarbonyl; and carbamoyl;
Z 2 is selected from the group consisting of a hydrogen atom; a halogen atom; cyano; C 1 -C 8 -alkyl; and C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
L 1 and L 2 are independently selected from the group consisting of CZ 4 Z 5 ;
m is 1 or 2;
X is CZ 7 ;
Z 7 and each Z 3 are independently selected from the group consisting of a hydrogen atom; a halogen atom; nitro; cyano; hydroxyl; thio; amino; pentafluoro-λ 6 -thio; C 1 -C 4 -alkyl; C 1 -C 4 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 4 -alkylamino; di-C 1 -C 4 -alkylamino; C 1 -C 4 -alkoxy; C 1 -C 4 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl; C 1 -C 4 -alkylsulfanyl; C 1 -C 4 -halogenoalkylsulfanyl comprising up to 9 halogen atoms that can be the same or different; C 2 -C 4 -alkenyl; C 2 -C 4 -halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C 2 -C 4 -alkynyl; C 2 -C 4 -halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different; C 2 -C 4 -alkenyloxy; C 2 -C 4 -halogenoalkenyloxy comprising up to 9 halogen atoms that can be the same or different; C 2 -C 4 -alkynyloxy; C 2 -C 4 -halogenoalkynyloxy comprising up to 9 halogen atoms that can be the same or different; C 3 -C 7 -cycloalkyl; C 3 -C 7 -cycloalkyl-C 1 -C 4 -alkyl; C 3 -C 7 -halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different; formyl; formyloxy; formylamino; carboxy; carbamoyl; N-hydroxycarbamoyl; carbamate; (hydroxyimino)-C 1 -C 4 -alkyl; C 1 -C 4 -alkylcarbonyl; C 1 -C 4 -halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 4 -alkylcarbamoyl; di-C 1 -C 4 -alkylcarbamoyl; —C 1 -C 4 -alkyloxycarbamoyl; C 1 -C 4 -alkoxycarbamoyl; —C 1 -C 4 -alkyl-C 1 -C 4 -alkoxycarbamoyl; C 1 -C 4 -alkoxycarbonyl; C 1 -C 4 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 4 -alkylaminocarbonyl; di-C 1 -C 4 -alkylaminocarbonyl; C 1 -C 4 -alkylcarbonyloxy; C 1 -C 4 -halogenoalkylcarbonyloxy comprising up to 9 halogen atoms that can be the same or different; C 1 -C 4 -alkylcarbonylamino; C 1 -C 4 -halogenoalkylcarbonylamino comprising up to 9 halogen atoms that can be the same or different; C 1 -C 4 -alkylaminocarbonyloxy; di-C 1 -C 4 -alkylaminocarbonyloxy; C 1 -C 4 -alkyloxycarbonyloxy; C 1 -C 4 -alkylsulfenyl; C 1 -C 4 -halogenoalkylsulfenyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 4 -alkylsulfinyl; C 1 -C 4 -halogenoalkylsulfinyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 4 -alkylsulfonyl; C 1 -C 4 -halogenoalkylsulfonyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 4 -alkoxyimino; (C 1 -C 4 -alkoxyimino)-C 1 -C 4 -alkyl; (C 1 -C 4 -alkenyloxyimino)-C 1 -C 4 -alkyl; (C 1 -C 4 -alkynyloxyimino)-C 1 -C 4 -alkyl; (benzyloxyimino)-C 1 -C 4 -alkyl; phenyl that can be substituted by up to two groups Q; benzyloxy that can be substituted by up to two groups Q; benzylthio that can be substituted by up to two groups Q; benzylamino that can be substituted by up to two groups Q; naphthyl that can be substituted by up to two groups Q; phenoxy that can be substituted by up to two groups Q; phenylamino that can be substituted by up to two groups Q; phenylthio that can be substituted by up to two groups Q; phenylmethylene that can be substituted by up to two groups Q; pyridinyl that can be substituted by up to two groups Q; pyridinyloxy that can be substituted by up to two groups Q; and phenoxymethylene that can be substituted by up to two groups Q; or
two substituents Z 3 or Z 7 together with the consecutive carbon atoms to which they are linked can form a 5- or 6-membered, saturated or non-saturated, carbo- or hetero-cycle, that can be substituted by up to two groups Q that can be the same or different;
p is 1 or 2;
Z 4 and Z 5 are independently selected from the group consisting of a hydrogen atom; a halogen atom; cyano; nitro; 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 -alkoxy-C 1 -C 8 -alkyl; C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different; C 3 -C 7 -cycloalkyl; C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl; C 3 -C 7 -halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different; formyl; C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylsulfinyl; C 1 -C 8 -halogenoalkylsulfinyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 8 -alkylsulfonyl; and C 1 -C 8 -halogenoalkylsulfonyl comprising up to 9 halogen atoms that can be the same or different;
each Q is independently selected from the group consisting of a halogen atom; cyano; nitro; C 1 -C 4 -alkyl; C 1 -C 4 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 4 -alkoxy; C 1 -C 4 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C 1 -C 4 -alkylsulfanyl; and C 1 -C 4 -halogenoalkylsulfanyl comprising up to 9 halogen atoms that can be the same or different;
provided that:
(A) Z 4 and Z 5 cannot all be hydrogen; and
(B) the compound is not 3-(cyclopropylamino)-2,3-dihydro-1,7-dimethyl-1H-indan-4-ol.
2. The compound of claim 1 wherein Z 1 is a cyclopropyl.
3. The compound of claim 1 wherein Z 1 is a non-substituted cyclopropyl.
4. The compound of claim 1 wherein Z 2 is a hydrogen atom.
5. The compound of claim 1 wherein Z 7 and each Z 3 are independently selected from the group consisting of a hydrogen atom; a halogen atom; C 1 -C 4 -alkyl; C 1 -C 4 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 4 -alkoxy; and C 1 -C 4 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different.