Pyrimidine derivatives and their use for controlling undesired plant growth

1. A compound of the formula (I) and/or an agrochemically compatible salt thereof

in which

R 1 and R 2 , independently of one another, are selected from the group consisting of

hydrogen, halogen, hydroxy, cyano, nitro, amino, C(O)OH, C(O)NH 2 ;

(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-halo-alkylcarbonyl, (C 1 -C 6 )-alkylcarbonyloxy, (C 1 -C 6 )-haloalkylcarbonyloxy, (C 1 -C 6 )-alkylcarbonyl-(C 1 -C 4 )-alkyl;

(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-haloalkoxycarbonyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-halo-alkoxycarbonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkoxycarbonyl-(C 1 -C 6 )-haloalkyl;

(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkenylcarbonyl, (C 2 -C 6 )-haloalkenylcarbonyl, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-haloalkenyloxy, (C 2 -C 6 )-alkenyloxycarbonyl, (C 2 -C 6 )-haloalkenyloxycarbonyl;

(C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkynylcarbonyl, (C 2 -C 6 )-haloalkynylcarbonyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 2 -C 6 )-alkynyloxycarbonyl, (C 2 -C 6 )-haloalkynyloxycarbonyl;

tri(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl, di(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl, mono(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl, phenylsilyl-(C 2 -C 6 )-alkynyl;

(C 6 -C 14 )-aryl, (C 6 -C 14 )-aryloxy, (C 6 -C 14 )-arylcarbonyl and (C 6 -C 14 )-aryl-oxycarbonyl, which may in each case be substituted on the aryl moiety by halogen, (C 1 -C 6 )-alkyl and/or (C 1 -C 6 )-haloalkyl;

(C 6 -C 14 )-aryl-(C 1 -C 6 )-alkyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxy, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkylcarbonyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkylcarbonyloxy, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxycarbonyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxycarbonyloxy;

mono((C 1 -C 6 )-alkyl)amino, mono((C 1 -C 6 )-haloalkyl)amino, di((C 1 -C 6 )-alkyl)amino, di((C 1 -C 6 )-haloalkyl)amino, ((C 1 -C 6 )-alkyl-(C 1 -C 6 )-haloalkyl)amino, N—((C 1 -C 6 )-alkanoyl)amino, N—((C 1 -C 6 )-haloalkanoyl)amino, aminocarbonyl-(C 1 -C 6 )-alkyl, di(C 1 -C 6 )-alkylaminocarbonyl-(C 1 -C 6 )-alkyl;

mono((C 1 -C 6 )-alkyl)aminocarbonyl, mono((C 1 -C 6 )-haloalkyl)aminocarbonyl, di((C 1 -C 6 )-alkyl)aminocarbonyl, di((C 1 -C 6 )-haloalkyl)aminocarbonyl, ((C 1 -C 6 )-alkyl-(C 1 -C 6 )-haloalkyl)aminocarbonyl, N—((C 1 -C 6 )-alkanoyl)aminocarbonyl, N—((C 1 -C 6 )-haloalkanoyl)aminocarbonyl;

(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkoxy;

(C 3 -C 8 )-cycloalkyl, which may be optionally substituted on the cycloalkyl radical by (C 1 -C 6 )-alkyl and/or halogen; (C 3 -C 8 )-cycloalkoxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkoxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkoxy, (C 3 -C 8 )-cycloalkylcarbonyl, (C 3 -C 8 )-cycloalkoxycarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkylcarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-halo alkylcarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkoxycarbonyl, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkoxycarbonyl, (C 3 -C 8 )-cycloalkylcarbonyloxy, (C 3 -C 8 )-cycloalkoxycarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkylcarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-haloalkylcarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-alkoxycarbonyloxy, (C 3 -C 8 )-cycloalkyl-(C 1 -C 6 )-halo alkoxy-carbonyloxy;

(C 3 -C 8 )-cycloalkenyl, (C 3 -C 8 )-cycloalkenyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkoxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkoxy, (C 3 -C 8 )-cycloalkenylcarbonyl, (C 3 -C 8 )-cycloalkenyloxycarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkylcarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkylcarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkoxycarbonyl, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkoxycarbonyl, (C 3 -C 8 )-cycloalkenylcarbonyloxy, (C 3 -C 8 )-cycloalkenyloxycarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkylcarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkylcarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-alkoxycarbonyloxy, (C 3 -C 8 )-cycloalkenyl-(C 1 -C 6 )-haloalkoxycarbonyloxy;

hydroxy-(C 1 -C 6 )-alkyl, hydroxy-(C 1 -C 6 )-alkoxy, cyano-(C 1 -C 6 )-alkoxy, cyano-(C 1 -C 6 )-alkyl;

(C 1 -C 6 )-alkylsulfonyl, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkylsulfinyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 1 -C 6 )-haloalkylthio, (C 1 -C 6 )-haloalkylsulfinyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfonyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkylsulfinyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylsulfonyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylsulfinyl-(C 1 -C 6 )-halo alkyl, (C 1 -C 6 )-halo alkylsulfonyl-(C 1 -C 6 )-halo alkyl, (C 1 -C 6 )-haloalkylthio-(C 1 -C 6 )-halo alkyl, (C 1 -C 6 )-haloalkylsulfinyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylsulfonyloxy, (C 1 -C 6 )-haloalkylsulfonyloxy, (C 1 -C 6 )-alkylthiocarbonyl, (C 1 -C 6 )-haloalkylthiocarbonyl, (C 1 -C 6 )-alkylthiocarbonyloxy, (C 1 -C 6 )-haloalkylthiocarbonyloxy, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkylthio-(C 1 -C 6 )-alkylcarbonyloxy, (C 4 -C 14 )-arylsulfonyl, (C 6 -C 14 )-arylthio, (C 6 -C 14 )-arylsulfinyl, (C 3 -C 8 )-cycloalkylthio, (C 3 -C 8 )-alkenylthio, (C 3 -C 8 )-cycloalkenylthio, (C 3 -C 6 )-alkynylthio;

R 3 is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl;

R 4 is selected from the group consisting of (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, hydroxy, (C 1 -C 6 )-alkoxy and (C 1 -C 6 )-haloalkoxy; or, together with the carbon atom to which it is bonded with R 5 , forms a three- to seven-membered ring;

R 5 is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, hydroxy, (C 1 -C 6 )-alkoxy and (C 1 -C 6 )-haloalkoxy; or, together with the carbon atom to which it is bonded with R 4 , forms a three- to seven-membered ring;

R 6 and

R 7 in each case independently of one another are selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 6 -C 14 )-aryl, (C 6 -C 14 )-aryloxy, (C 6 -C 14 )-arylcarbonyl and (C 6 -C 14 )-aryloxycarbonyl; or the radicals R 6 and R 7 together form a (C 2 -C 7 )-alkylene group, which may comprise one or more oxygen and/or sulfur atoms, where the (C 2 -C 7 )-alkylene group may be mono- or polysubstituted by halogen and the respective halogen substituents may be identical or different,

R 8 is selected from the group consisting of hydrogen, halogen, cyano, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkyloxycarbonyl, (C 1 -C 6 )-alkyl-aminocarbonyl, (C 1 -C 6 )-dialkylaminocarbonyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkynylcarbonyl, (C 2 -C 6 )-haloalkynylcarbonyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 2 -C 6 )-alkynyloxycarbonyl and (C 2 -C 6 )-haloalkynyloxycarbonyl;

R 9 is selected from the group consisting of hydrogen, halogen, cyano, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkyloxycarbonyl, (C 1 -C 6 )-alkyl-aminocarbonyl, (C 1 -C 6 )-dialkylaminocarbonyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkynylcarbonyl, (C 2 -C 6 )-haloalkynylcarbonyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 2 -C 6 )-alkynyloxycarbonyl and (C 2 -C 6 )-haloalkynyloxycarbonyl;

R 10 is selected from the group consisting of, halogen, cyano, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkyloxycarbonyl, (C 1 -C 6 )-alkylaminocarbonyl, (C 1 -C 6 )-dialkylaminocarbonyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkynylcarbonyl, (C 2 -C 6 )-haloalkynylcarbonyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 2 -C 6 )-alkynyloxycarbonyl and (C 2 -C 6 )-haloalkynyloxycarbonyl;

R 11 is selected from the group consisting of hydrogen, halogen, cyano, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkyloxycarbonyl, (C 1 -C 6 )-alkyl-aminocarbonyl, (C 1 -C 6 )-dialkylaminocarbonyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkynylcarbonyl, (C 2 -C 6 )-haloalkynylcarbonyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 2 -C 6 )-alkynyloxycarbonyl and (C 2 -C 6 )-haloalkynyloxycarbonyl; and

X is a single bond,

R 12 and

R 13 in each case independently of one another are selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl,

R 14 is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, and (C 1 -C 6 )-haloalkyl,

wherein the stereochemical configuration on the carbon atom indicated by (*) is (R), and

provided R 2 does not denote chloro if R 1 is NH 2 .

2. A compound of the formula (I) as claimed in claim 1 , wherein the radical R 1 is selected from the group consisting of hydrogen, halogen, cyano, C(═O)NH 2 , NO 2 , (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 3 -C 6 )-cyclopropyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkylthio, (C 2 -C 6 )-alkynyl, mono(C 1 -C 6 )-alkylamino, di(C 1 -C 6 )-alkylamino and tri(C 1 -C 6 )-alkylsilyl-(C 2 -C 6 )-alkynyl.

3. A compound of the formula (I) as claimed in claim 1 , wherein the radical R 2 is selected from the group consisting of hydrogen, halogen, (C 1 -C 6 )-alkylphenyl, (C 6 -C 14 )-aryl, which may be substituted on the aryl radical by (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl and/or halogen; (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, which may be substituted on the cycloalkyl radical by (C 1 -C 6 )-alkyl, (C 6 -C 14 )-haloaryl and/or halogen; 1-(C 1 -C 6 )-alkylcyclopropyl, 1-(C 1 -C 6 )-alkyl-C 6 -aryl)cyclopropyl, 1-(monohalophenyl)cyclopropyl, 1-(dihalophenyl)cyclopropyl, mono(C 1 -C 6 )-alkylamino, di(C 1 -C 6 )-alkylamino, (C 1 -C 6 )-thioalkyl, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkoxy and amino.

4. A compound of the formula (I) as claimed in claim 1 , wherein the radical R 3 is hydrogen or (C 1 -C 6 )-alkyl.

5. A compound of the formula (I) as claimed in claim 1 , wherein the radical R 4 is selected from the group consisting of (C 1 -C 6 )-alkyl, hydroxy, and (C 1 -C 6 )-alkoxy or, together with the carbon atom to which it is bonded with R 5 , forms a three- to seven-membered ring.

6. A compound of the formula (I) as claimed in claim 1 , wherein the radicals R 4 and R 5 together with the carbon atom to which they are bonded form a three- to seven-membered ring.

7. A compound of the formula (I) as claimed in claim 1 , wherein the radicals R 6 and R 7 , independently of one another, are selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl and (C 6 -C 14 )-aryl.

8. A compound of the formula (I) as claimed in claim 1 , wherein the radical R 8 is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl and halogen.

9. A compound of the formula (I) as claimed in claim 1 , wherein the radical R 9 is selected from the group consisting of hydrogen and (C 1 -C 6 )-alkyl.

10. A compound of the formula (I) as claimed in claim 1 , wherein the radical R 10 is selected from the group consisting of (C 1 -C 6 )-alkyl, (C 1 -C 6 )-dialkylaminocarbonyl, halogen, (C 2 -C 6 )-alkynyl, cyano, and (C 1 -C 6 alkyloxycarbonyl.

11. A compound of the formula (I) as claimed in claim 1 , wherein R 11 is selected from the group consisting of hydrogen and (C 1 -C 6 )-alkyl.

12. A process for the preparation of compounds of the formula (I) of claim 1

which comprises

(1) reacting a compound of the formula (II)

in which Z 1 is an exchangeable radical or a leaving group,

with an amine of the formula (III) or an acid addition salt thereof

13. A herbicidal or plant growth regulating composition, which comprises one or more compounds of the formula (I) or salts thereof as claimed in claim 1 .

14. A method for controlling harmful plants or for regulating the growth of plants, which comprises applying an effective amount of one or more compounds of the formula (I) or salts thereof as claimed in claim 1 to plants, plant parts, plant seeds or to an area under cultivation.

15. A compound of the formula (I) as claimed in claim 1 , wherein the radical R 5 is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, hydroxy, cyclopropyl and (C 1 -C 6 )-alkoxy.

16. A method according to claim 14 , in which the applying of an effective amount of one or more compounds of the formula (I) or salts thereof, as claimed in claim 1 , occurs to an area under cultivation before the emergence of crop plants.

17. A method according to claim 14 , in which the applying of an effective amount of one or more compounds of the formula (I) or salts thereof, as claimed in claim 1 , occurs to an area under cultivation after the emergence of crop plants.

18. A compound according to claim 1 , selected from compounds

19. A compound according to claim 1 , in which

R 1 and R 2 , independently of one another, are selected from the group consisting of hydrogen, halogen, hydroxy, cyano, nitro, amino, C(O)OH, C(O)NH 2 , (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, and (C 1 -C 6 )-alkylcarbonyl;

R 3 is hydrogen;

R 4 is a (C 1 -C 6 )-alkyl or, together with the carbon atom to which it is bonded with R 5 , forms a three- to seven-membered ring;

R 5 is a hydrogen or, together with the carbon atom to which it is bonded with R 4 , forms a three- to seven-membered ring;

R 6 is a hydrogen,

R 7 is a hydrogen,

R 8 is selected from the group consisting of hydrogen, halogen, (C 1 -C 6 )-alkyl, and (C 1 -C 6 )-alkylcarbonyl;

R 9 is selected from the group consisting of hydrogen, halogen, (C 1 -C 6 )-alkyl, and (C 1 -C 6 )-alkylcarbonyl;

R 10 is selected from the group consisting of, halogen, cyano, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkyloxycarbonyl, (C 1 -C 6 )-alkylamino carbonyl, (C 1 -C 6 )-dialkylaminocarbonyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 2 -C 6 )-alkynylcarbonyl, (C 2 -C 6 )-haloalkynylcarbonyl, (C 2 -C 6 )-alkynyloxy, (C 2 -C 6 )-haloalkynyloxy, (C 2 -C 6 )-alkynyloxycarbonyl and (C 2 -C 6 )-haloalkynyloxycarbonyl;

R 11 is a hydrogen;

X is a single bond,

R 12 and

R 13 in each case independently of one another are selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl,

R 14 is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, and (C 1 -C 6 )-haloalkyl,

wherein the stereochemical configuration on the carbon atom indicated by (*) is (R), and provided R 2 does not denote chloro if R 1 is NH 2 .

20. A compound of the formula (I) as claimed in claim 1 , wherein the radical R 4 together with the carbon atom to which it is bonded with R 5 , forms a three membered ring.