Fluoralkylphenylamidines and the use thereof as fungicides

1. A fluoroalkylphenylamidine of the formula (I)

in which

x represents an integer selected from the group consisting of 1, 2 and 3;

A is selected from the group consisting of O, NH, CH 2 , CHR 8 and a single bond;

R 1 is selected from the group consisting of hydrogen; straight-chain or branched C 1-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl groups, cyclic C 3-12 -alkyl, C 4-12 -alkenyl or C 4-12 -alkynyl groups, where all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′ 2 , —SiR′ 3 , —COOR′, —CN and —CONR′ 2 , where R′ may represent hydrogen or a C 1-12 -alkyl group, and where X may represent a halogen atom; —SH; —SR″, where R″ may represent a straight-chain or branched C 1-12 -alkyl group which may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′, —SiR′ 3 , —COOR′, —CN and —CONR′ 2 , where R′ has the above meanings;

R 2 is selected from the group consisting of straight-chain or branched C 1-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl groups, cyclic C 3-8 -alkyl, C 4-8 -alkenyl, C 4-8 -alkynyl groups, C 5-18 -aryl, C 7-19 -aralkyl and C 7-19 -alkaryl groups, where all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′ 2 , —SiR′ 3 , —COOR′, —CN and —CONR′ 2 , where R′ has the above meanings;

R 3 is selected from the group consisting of —CN, —SH, —SR″, —OR″, —(C═O)—R″, straight-chain or branched C 1-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl groups, cyclic C 3-8 -alkyl, C 4-8 -alkenyl, C 4-8 -alkynyl groups, C 5-18 -aryl, C 7-19 -aralkyl and C 7-19 -alkaryl groups, where all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′ 2 , —SiR′ 3 , —COOR′, —CN and —CONR′ 2 , where R′ and R″ have the above meanings;

R 4 is selected from the group consisting of —X, —CN, —SH, —SR″, —OR″, —(C═O)—R″, straight-chain or branched C 1-12 -alkyl, C 2-12 -alkenyl, C 2-12 -alkynyl groups, cyclic C 3-8 -alkyl, C 4-8 -alkenyl, C 4-8 -alkynyl groups, C 5-18 -aryl, C 7-19 -aralkyl and C 7-19 -alkaryl groups, where all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′ 2 , —SiR′ 3 , —COOR′, —CN and —CONR′ 2 , where R′ and R″ have the above meanings;

R 5 is selected from the group consisting of C 5-18 -aryl, C 7-19 -aralkyl and C 7-19 -alkaryl groups, where all of the groups mentioned above may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′ 2 , —SiR′ 3 , —COOR′, —CN and —CONR′ 2 , where R′ has the above meanings;

and/or a salt thereof.

2. The fluoroalkylphenylamidine and/or a salt thereof as claimed in claim 1 where

A is selected from the group consisting of O, NH, CH 2 and a single bond;

x represents an integer selected from the group consisting of 2 and 3;

R 1 is selected from the group consisting of hydrogen, mercapto (—SH) or C 1-8 -alkyl groups;

R 2 is selected from the group consisting of C 1-8 -alkyl groups;

R 3 is selected from the group consisting of straight-chain C 2 -C 8 -alkyl groups, branched and alicyclic C 3-8 -alkyl groups;

R 4 is selected from the group consisting of —X, straight-chain or branched C 1-8 -alkyl groups and C 1-5 -haloalkyl groups;

R 5 is selected from the group consisting of the formulae (II-a), (II-d), and (II-f),

in which

represents an integer of 0, 1, 2 or 3;

represents N or CH,

R 6 is selected from the group consisting of hydrogen, straight-chain C 1-12 -alkyl groups, branched or cyclic C 3-8 -alkyl groups, halogen atoms, C 1-5 -haloalkyl groups;

R 8 is selected from C 1-12 -alkyl groups.

3. The fluoroalkylphenylamidine as claimed in claim 1 where

A is selected from the group consisting of O, NH, CH 2 or a single bond;

x represents an integer selected from the group consisting of 1, 2 and 3;

R 1 is selected from the group consisting of hydrogen, methyl and ethyl;

R 2 is selected from the group consisting of methyl and ethyl;

R 3 is selected from the group consisting of methyl, ethyl and cyclopropyl;

R 4 may be selected from the group consisting of Cl and F atoms and —CF 3 , —CF 2 H, —CH 2 F and methyl groups;

R 5 is selected from the group consisting of (i) and (ii)

(i) groups of the formula (II-g)

in which

R 6 represents halogen, a C 1-8 -alkyl group, a C 1-5 -haloalkyl group and

R 7 represents hydrogen, halogen, chlorine or fluorine, a C 1-8 -alkyl group or a C 1-5 -haloalkyl group,

(ii) groups of the formula (II-h)

in which

R 2 may represent halogen, a straight-chain or branched C 1-8 -alkyl group, C 3-12 -cycloalkyl, C 5-18 -aryl, C 7-19 -aralkyl and C 7-19 -alkaryl groups, where the groups mentioned above may be substituted with —SiR′ 3 , —OR′ and —CN, where R′ has the above meanings.

4. A fluoroalkylphenylamidine selected from the group consisting of (1) N-ethyl-N-methyl-N′-[4-(3-tert-butyl-4-chlorophenoxy)-5-fluoromethyl-2-methylphenyl]formamidine, (2) N-ethyl-N-methyl-N′-[4-(4-tert-butylphenyl)-5-fluoromethyl-2-methylphenyl]formamidine, (3) N-ethyl-N-methyl-N′-[4-(3-tert-butyl-4-chlorophenoxy)-5-trifluoromethyl-2-methylphenyl]formamidine, (4) N-ethyl-N-methyl-N′-[4-(3-iso-propylphenoxy)-5-trifluoromethyl-2-methylphenyl]formamidine, (5) N-ethyl-N-methyl-N′-[4-(3-trifluoromethyl-4-chlorophenoxy)-5-trifluoromethyl-2-methylphenyl]formamidine, (6) N-propyl-N-methyl-N′-[4-(3-trifluoromethyl-4-chlorophenoxy)-5-trifluoromethyl-2-methylphenyl]formamidine, (8) N,N-dimethyl-N′-[4-(3-tert-butyl-4-chlorophenoxy)-5-trifluoromethyl-2-methylphenyl]formamidine, (9) N-ethyl-N-methyl-N′-[4-(3-tert-butyl-4-chlorophenoxy)-5-difluoromethyl-2-methylphenyl]formamidine, (10) N-ethyl-N-methyl-N′-[4-(3,4-dichlorophenoxy)-5-difluoromethyl-2-methylphenyl]formamidine, (11) N-ethyl-N-methyl-N′-[4-(3-tert-butylphenoxy)-5-trifluoromethyl-2-methylphenyl]formamidine, (12) N-ethyl-N-methyl-N′-[4-(4-tert-butylphenyl)-5-trifluoromethyl-2-ethylphenyl]formamidine, (13) N-ethyl-N-methyl-N′-[4-phenoxy-5-difluoromethyl-2-methylphenyl]formamidine, (15) N-ethyl-N-methyl-N′-{4-[3-(1-hydroxyethyl)-phenoxy]-5-difluoromethyl-2-methylphenyl}formamidine, (16) N-ethyl-N-methyl-N′-{4-[3-(1-fluoroethyl)-phenoxy]-5-difluoromethyl-2-methylphenyl}formamidine, (17) N-ethyl-N-methyl-N′-[4-(3-isopropyl-4-chlorophenoxy)-5-difluoromethyl-2-methylphenyl]formamidine, and (18) N-ethyl-N-methyl-N′-[4-(3-iso-propylphenoxy)-5-difluoromethyl-2-methylphenyl]formamidine.

5. A composition for controlling unwanted microorganisms, comprising at least one fluoroalkylphenylamidine as claimed in claim 1 .

6. A method for controlling unwanted microorganisms, comprising applying a fluoroalkylphenylamidine and/or a salt thereof as claimed in claim 1 to the microorganisms and/or a habitat thereof.

7. Seed treated with at least one fluoroalkylphenylamidine as claimed in claim 1 .

8. A method for treating seed comprising using a fluoroalkylphenylamidine and/or a salt thereof as claimed in claim 1 to the seed.

9. A method for treating transgenic plants comprising applying a fluoroalkylphenylamidine and/or a salt thereof as claimed in claim 1 to the transgenic plants.

10. Seed of a transgenic plant treated with a fluoroalkylphenylamidine and/or a salt thereof as claimed in claim 1 .