Benzhydryl derivatives

Details Benzhydryl derivatives Benzhydryl derivatives

2002-10-29

2004-07-27

Keys, Rosalynd (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C514S648000, C514S706000, C514S721000, C568S645000, C568S062000, C568S640000, C568S641000, C564S327000, C560S238000, C560S250000, C560S255000, C560S252000

Reexamination Certificate

active

06767923

ABSTRACT:

DESCRIPTION
The invention relates to benzhydryl derivatives of the formula I,
where the index and the variables are as defined below:
X is oxygen or sulfur;
R
1
, R
3
are halogen, cyano, nitro, hydroxyl, mercapto, amino,
C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkynyloxy, C
1
-C
6
-alkylcarbonyloxy, formyloxy, C
1
-C
6
-alkylthio, C
2
-C
6
-alkenylthio, C
2
-C
6
-alkynylthio, C
1
-C
6
-alkylamino, di-C
1
-C
6
-alkylamino, C
1
-C
6
-alkylcarbonyl or formyl, where the carbon atoms in the radicals mentioned may be partially or fully halogenated;
R
2
is halogen, cyano, nitro, hydroxyl, mercapto, amino, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-haloalkyl or C
1
-C
6
-haloalkoxy, where the groups R
2
may be different if n=2;
R
4
is C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl, where the carbon atoms in these radicals may be unsubstituted or partially or fully halogenated;
R
5
, R
6
are hydroxyl, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-haloalkenyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyloxy, C
1
-C
6
-haloalkoxy, C
2
-C
6
-haloalkenyloxy, C
3
-C
8
-cycloalkyl, C
3
-C
8
-cycloalkyl-C
1
-C
3
-alkyl, C
3
-C
8
-cycloalkoxy or C
3
-C
8
-cycloalkyl-C
1
-C
3
-alkoxy;
n is 0, 1 or 2.
Additionally, the invention relates to processes for preparing the compounds I, to compositions comprising them and to the use of the compounds I for controlling phytopathogenic fungi.
In JP 08225474 various benzhydryl alcohols have been described as starting materials for pharmaceutics.
EP-A 461 079 discloses various benzhydryl alcohols having herbicidal action.
Benzhydryl alcohols having fungicidal action are already known, for example
(RS)-2,4′-difluoro-alpha-(1H-1,2,4-triazol-1-ylmethyl)benzhydryl alcohol (flutriafol; EP-A 015 756) or
(R,S)-2,4′-dichloro-alpha-(pyrimidin-5-yl)benzhydryl alcohol (fenarimol; GB 1 218 623). However, their action is not entirely satisfactory.
Benzophenones having fungicidal action are known from EP-A 727 141.
It is an object of the present invention to provide benzhydryl derivatives having a higher efficacy in the control of harmful fungi.
We have found that this object is achieved by the benzhydryl derivatives of the formula I. Furthermore, we have found processes for preparing the compounds I and compositions comprising them for controlling harmful fungi.
The compounds of the formula I differ from the benzhydryl alcohols disclosed in JP 08225474 by the substitution pattern on the phenyl rings.
The compounds of the formula I differ from the herbicidally active benzhydryl alcohols disclosed in EP-A 461 079 by the substituents of the phenyl rings, which substituents are fixed in positions 2, 2, 2′, 2′, 3′, 4 and 4′.
The compounds of the formula I are secondary alcohols or thiols, whereas the compounds disclosed in EP-A 015 756 and GB 1 218 623 are tertiary alcohols which furthermore differ from compounds of the formula I in the substitution pattern on the phenyl rings.
The compounds of the formula I differ from the fungicidally active benzophenones disclosed in EP-A 727 141 in that the keto group is replaced by an alcohol or thiol function, and by the substitution patterns on the phenyl rings.
In the definitions of the symbols given in the formulae above, collective terms were used which, in general, represent the following substituents:
Halogen: fluorine, chlorine, bromine or iodine, preferably chlorine or bromine;
Alkyl: saturated, straight-chain or branched hydrocarbon radicals having 1 to 4 or 1 to 6 carbon atoms, for example C
1
-C
6
-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;
Haloalkyl: straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as mentioned above), it being possible for some or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, for example C
1
-C
2
-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
Alkoxy: straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as mentioned above), which are attached to the phenyl ring via an oxygen atom (—O—);
Haloalkoxy: straight-chain or branched haloalkyl groups having 1 to 6 carbon atoms (as mentioned above) which are attached to the phenyl ring via an oxygen atom (—O—);
Alkylthio: straight-chain or branched alkyl groups having 1 to 6 or 1 to 4 carbon atoms (as mentioned above) which are attached to the phenyl ring via a sulfur atom (—S—);
Alkylamino: a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as mentioned above) which is attached to the phenyl ring via an amino group (—NH—);
Dialkylamino: two independent straight-chain or branched alkyl groups having in each case 1 to 6 carbon atoms (as mentioned above) which are attached to the phenyl ring via a nitrogen atom;
Alkylcarbonyloxy: a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as mentioned above) which is attached to the phenyl ring via a carbonyloxy group (—CO
2
—);
Alkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 6 carbon atoms and a double bond in any position, for example C
2
-C
6
-alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
Haloalkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 6 carbon atoms and a double bond in any position (as mentioned above), it being possible for some or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, in particular by fluorine, chlorine and bromine;
Alkenyloxy: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 6 carbon atoms and a double bond in any position which is not adjacent to the heteroatom (as mentioned above), which are attached to the phenyl ring via an oxygen atom (—O—);
Haloalk

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