5-aminopyrimidine derivatives and use thereof for combating undesired plant growth

1. A compound of formula (I) or an agrochemically acceptable salt thereof

in which

R 1 is selected from the group consisting of

cyano (CN), NO 2 , (C 1 -C 3 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 6 )-alkylthio, (C 1 -C 6 )-alkyl sulfoxide, (C 1 -C 6 )-alkylsulfonyl, (C 1 -C 6 )-haloalkylsulfonyl, (C 1 -C 6 )-alkoxy-carbonyl, amino-carbonyl, mono-((C 1 -C 6 )-alkyl)-amino-carbonyl, di-((C 1 -C 6 )-alkyl)-amino-carbonyl, (C 6 -C 14 )-aryl, (C 6 -C 14 )-aryl-haloalkyl, (C 1 -C 6 )-aryloxy, (C 6 -C 14 )-haloaryl-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkynyl-(C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkynyl-(C 1 -C 6 )-alkyl-(C 1 -C 6 )-alkoxy, and (C 1 -C 6 )-alkyl-(C 2 -C 6 )-alkynyl-(C 1 -C 6 )-alkoxy; and

R 2a and R 2b , each independently of one another, are selected from the group consisting of

hydrogen, halogen, hydroxy, cyano, nitro, 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 )-haloalkylcarbonyl, (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 )-haloalkoxycarbonyl-(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 )-aryloxycarbonyl, each of which may be substituted at the aryl moiety by halogen, (C 1 -C 6 )-alkyl 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 )-alkyl-carbonyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkyl-carbonyloxy, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxycarbonyl, (C 6 -C 14 )-aryl-(C 1 -C 6 )-alkoxycarbonyloxy;

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

N—((C 1 -C 6 )-haloalkanoyl)-amino-carbonyl, mono-((C 6 -C 14 )-aryl)-amino-carbonyl, di-((C 6 -C 14 )-aryl)-amino-carbonyl;

(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 optionally be substituted at the cycloalkyl radical by (C 1 -C 6 )-alkyl 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 )-haloalkylcarbonyl, (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 )-haloalkoxycarbonyloxy;

(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 )-haloalkyl, (C 1 -C 6 )-haloalkylsulfonyl-(C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-haloalkylthio-(C 1 -C 6 )-haloalkyl, (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, and (C 3 -C 6 )-alkynylthio; and

R 3 is selected from the group consisting of

hydrogen, cyano, C(O)OH, C(O)NH 2 ;

(C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl; and

(C 1 -C 6 )-alkoxycarbonyl; and

R 4 and R 5 , each independently of one another, are 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 the radicals R 4 and R 5 together with the carbon atom to which they are attached form a three- to seven-membered ring; and

R 6 and R 7 , each 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 1 -C 7 )-alkylene group, which may contain one or more oxygen or sulfur atoms, where the (C 1 -C 7 )-alkylene group may be mono- or polysubstituted by halogen and the halogen substituents in question may be identical or different, and

n is the number 0, 1 or 2 and

R 8 , R 9 , R 10 and R 11 , each independently of one another, are selected from the group consisting of hydrogen, halogen, cyano, C(O)OH, C(O)NH 2 , (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkylcarbonyl, (C 1 -C 6 )-alkyloxycarbonyl, (C 1 -C 6 )-alkylaminocarbonyl, (C 1 -C 6 )-di-alkylaminocarbonyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 2 -C 6 )-alkenyl, (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 nitro;

X is a bond, CH 2 , O, S, carbonyl, NH, CR 12 R 13 or NR 14 or CH 2 O, CH 2 S, where in the two last-mentioned groups the carbon atom is attached to the aromatic moiety and the heteroatom O or S is attached to the partially hydrogenated moiety of the amine;

and

R 12 and R 13 , each independently of one another, are selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-haloalkyl; and

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

2. The compound of formula (I) as claimed in claim 1 , wherein the radicals R 2a and R 2b , each independently of one another, are selected from the group consisting of hydrogen, CN, hydroxy (OH), (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkoxy, aminocarbonyl, hydroxycarbonyl COOH, (C 1 -C 6 )-alkoxycarbonyl, (C 1 -C 6 )-alkyl sulfonyl, mono-((C 1 -C 6 )-alkyl)-amino-carbonyl, di-((C 1 -C 6 )-alkyl)-amino-carbonyl, mono-((C 6 -C 14 )-aryl)-amino-carbonyl, mono-((C 2 -C 6 )-alkylene)-amino-carbonyl, mono-((C 6 -C 14 )-aryl-(C 1 -C 6 )-alkyl)-amino-carbonyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkoxy-carbonyl and di-((C 1 -C 6 )-alkyl)-amino-(C 1 -C 6 )-alkoxycarbonyl.

3. The compound of formula (I) as claimed in claim 1 , wherein the radical R 3 is selected from the group consisting of hydrogen, CH 3 , CH 2 CH 2 OCH 3 , COOCH 3 , CONH 2 and C 6 H 5 .

4. The compound of formula (I) as claimed in claim 1 , wherein the radicals R 4 and R 5 , each independently of one another, are selected from the group consisting of hydrogen, cyano, hydroxy, (C 1 -C 6 )-alkyl and (C 1 -C 6 )-alkoxy.

5. The compound of formula (I) as claimed in claim 1 , wherein the radicals R4 and R5 are a (C 1 -C 3 )-alkylene group and together with the carbon atom to which they are attached form a three- or four-membered ring.

6. The compound of formula (I) as claimed in claim 1 , wherein R6 and R7 independently of one another are selected from the group consisting of hydrogen, methyl and phenyl.

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

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

9. The compound of formula (I) as claimed in claim 1 , wherein the radical R 10 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, cyano, CONH 2 , COOH, methyl (CH 3 ), ethyl (CH 2 CH 3 ), methoxy (OCH 3 ), CH═CH 2 , C≡CH and C≡CCH 3 .

10. The compound of formula (I) as claimed in claim 1 , wherein the radical R 11 is selected from the group consisting of hydrogen and methyl.

11. The compound of formula (I) as claimed in claim 1 , wherein the radical X is selected from the group consisting of O, S, carbonyl, CH 2 , NH, CHCH 3 , NCH 3 , C(CH 3 ) 2 , OCH 2 , SCH 2 , and a chemical bond.

12. A process for preparing a compound of formula (I) or an agrochemically acceptable salt thereof or an agrochemically acceptable quaternized nitrogen derivative thereof as claimed in claim 1 : comprising reacting

a compound of formula (II)

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

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

13. The process as claimed in claim 12 , where the exchangeable radical or the leaving group Z 1 is fluorine, chlorine, bromine, iodine, a (C 1 -C 4 )-alkylsulfonyl, an unsubstituted or a substituted phenyl-(C 1 -C 4 )-alkylsulfonyl or a (C 1 -C 4 )-alkylphenylsulfonyl.

14. A herbicidal or plant growth-regulating composition, comprising one or more compounds of formula (I) or a salt thereof as claimed in claim 1 .

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

16. The method as claimed in claim 15 , wherein the compound is employed for controlling harmful plants or for regulating growth of plants in crops of useful plants or ornamental plants.

17. The method as claimed in claim 16 , wherein the plants are transgenic crop plants.

18. The method as claimed in claim 16 , wherein the plants are plantation crops.