Fungicide N-cycloalkyl-N-bicyclimethylene-carboxamide derivatives
View Patent ↗The present invention relates to N-cycloalkyl-N-bicyclicmethylene-carboxamide, thiocarboxamide or N-substituted carboximidamide derivatives of formula (I) wherein A represents a carbo-linked, 5-membered heterocyclyl group, T represents O or S, Z 1 represents a C 3 -C 7 -cycloalkyl group, X represents N or a CZ 7 and Y 1 , Y 2 , Z 2 , Z 3 , L 1 and L 2 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 are also disclosed.
1. A compound of formula
wherein:
Z 2 is selected from the group consisting of a hydrogen atom, a halogen atom, hydroxyl group, cyano, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, amino, and C 1 -C 8 -alkylamino;
Y 1 and Y 2 are independently selected from the group consisting of a hydrogen atom, a halogen atom, 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;
L 1 and each L 2 are independently selected from the group consisting of CZ 4 Z 5 , NZ 6 , O, S, S(O), and S(O) 2 ;
wherein:
Z 4 and Z 5 are independently selected from the group consisting of a hydrogen atom, a halogen atoms, 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;
Z 6 is selected from the group consisting of a hydrogen atom, 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 -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 -alkylsulfonyl, C 1 -C 8 -halogenoalkylsulfonyl comprising up to 9 halogen atoms that can be the same or different, phenylsulfonyl can be substituted by up to 5 groups Q that can be the same or different, and benzyl that can be substituted by up to 5 groups Q that can be the same or different;
m is 2;
X is selected from the group consisting of CZ 7 and N;
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 8 -alkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -arylalkyl, (C 3 -C 7 -cycloalkyl)-C 1 -C 8 -alkyl, C 1 -C 8 -alkylamino, di-C 1 -C 8 -alkylamino, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -alkylsulfanyl, C 1 -C 8 -halogenoalkylsulfanyl comprising up to 9 halogen atoms that can be the same or different, C 2 -C 8 -alkenyl, C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -arylalkenyl, (C 3 -C 7 -cycloalkyl)-C 1 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 2 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -arylalkynyl, (C 3 -C 7 -cycloalkyl)-C 1 -C 8 -alkynyl, C 2 -C 8 -alkenyloxy, C 2 -C 8 -halogenoalkenyloxy comprising up to 9 halogen atoms that can be the same or different, C 2 -C 8 -alkynyloxy, C 2 -C 8 -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 8 -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 8 -alkyl, 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 -alkylcarbamoyl, di-C 1 -C 8 -alkylcarbamoyl, N—C 1 -C 8 -alkyloxycarbamoyl, C 1 -C 8 -alkoxycarbamoyl, N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkylaminocarbonyl, di-C 1 -C 8 -alkylaminocarbonyl, C 1 -C 8 -alkylcarbonyloxy, C 1 -C 8 -halogenoalkylcarbonyloxy comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkylcarbonylamino, C 1 -C 8 -halogenoalkylcarbonylamino comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkylaminocarbonyloxy, di-C 1 -C 8 -alkylaminocarbonyloxy, C 1 -C 8 -alkyloxycarbonyloxy, C 1 -C 8 -alkylsulfenyl, C 1 -C 8 -halogenoalkylsulfenyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkylsulphinyl, C 1 -C 8 -halogenoalkylsulfinyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkylsulfonyl, C 1 -C 8 -halogenoalkylsulfonyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkoxyimino, (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl, (C 1 -C 8 -alkenyloxyimino)-C 1 -C 8 -alkyl, (C 1 -C 8 -alkynyloxyimino)-C 1 -C 8 -alkyl, a (benzyloxyimino)-C 1 -C 8 -alkyl, tri(C 1 -C 8 -alkyl)silyl, tri(C 1 -C 8 -alkyl)silyl-C 1 -C 8 -alkyl, phenyl that can be substituted by up to 5 groups Q that can be the same or different, benzyloxy that can be substituted by up to 5 groups Q that can be the same or different, benzylthio that can be substituted by up to 5 groups Q that can be the same or different, benzylamino that can be substituted by up to 5 groups Q that can be the same or different, naphthyl that can be substituted by up to 6 groups Q that can be the same or different, phenoxy that can be substituted by up to 5 groups Q that can be the same or different, phenylamino that can be substituted by up to 5 groups Q that can be the same or different, phenylthio that can be substituted by up to 5 groups Q that can be the same or different, phenylmethylene that can be substituted by up to 5 groups Q that can be the same or different, pyridinyl that can be substituted by up to 4 groups Q that can be the same or different, pyridinyloxy that can be substituted by up to 4 groups Q that can be the same or different, and phenoxymethylene that can be substituted by up to 5 groups Q; or
Z 7 or each Z 3 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, which can be substituted by up to four groups Q that can be the same or different; and
p is 1, 2, or 3;
provided that said compound does not represent N-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]cyclopropanamine or 3-cyclohexyl-1-[(cyclopropylamino)methyl]-3,4-dihydro-1H-isochromene-5,6-diol.
2. The compound of claim 1 wherein Y 1 is C 1 -C 5 -alkyl and Y 2 is hydrogen.
3. The compound of claim 2 wherein Y 1 is methyl.
4. The compound of claim 1 wherein Y 1 and Y 2 are both C 1 -C 5 -alkyl.
5. The compound of claim 4 wherein Y 1 and Y 2 are both methyl.
6. The compound of claim 1 wherein Z 2 is hydrogen.
7. The compound of claim 1 wherein L 1 is CZ 4 Z 5 .
8. The compound of claim 1 wherein L 2 is CZ 4 Z 5 and m is 2.
9. 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 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.
10. The compound of claim 1 wherein said compound is N-cyclopropyl-3-(difluoromethyl)-N-[1-(1-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)ethyl]-1-methyl-1H-pyrazole-4-carboxamide.