Herbicidal phenylpyridines

1. A compound of formula (I)

wherein the variables have the following meanings:

R 1 halogen, C 1 -C 4 -haloalkyl or SO 2 CH 3 ;

R 2 H, CH 3 or NH 2 ;

R 3 halogen;

R 4 H or halogen;

R 5 halogen or CN;

R 6 H or CH 3 ;

R 7 C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, or C 3 -C 6 -alkynyloxy;

R 8 OR 9 , SR 9 , NR 10 R 11 , NR 9 S(O)R 10 , NR 9 S(O) 2 R 10 , NR 9 S(O)NR 10 R 11 , or NR 9 S(O) 2 NR 10 R 11 ,

wherein

R 9 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -haloalkynyl, C 1 -C 6 -cyanoalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, di(C 1 -C 6 -alkoxy)C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, C 3 -C 6 -alkenyloxy-C 1 -C 6 -alkyl, C 3 -C 6 -haloalkenyloxy-C 1 -C 6 -alkyl, C 3 -C 6 -alkenyloxy-C 1 -C 6 -alkoxy-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 -alkylsulfonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxycarbonyl-C 1 -C 6 -alkyl, C 3 -C 6 -alkenyloxycarbonyl-C 1 -C 6 -alkyl, amino, (C 1 -C 6 -alkyl)amino, di(C 1 -C 6 -alkyl)amino, (C 1 -C 6 -alkylcarbonyl)amino, amino-C 1 -C 6 -alkyl, (C 1 -C 6 -alkyl)amino-C 1 -C 6 -alkyl, di(C 1 -C 6 -alkyl)amino-C 1 -C 6 -alkyl, aminocarbonyl-C 1 -C 6 -alkyl, (C 1 -C 6 -alkyl)aminocarbonyl-C 1 -C 6 -alkyl, di(C 1 -C 6 -alkyl)aminocarbonyl-C 1 -C 6 -alkyl,

—N═CR 12 R 13 , wherein R 12 and R 13 independently of one another are H, C 1 -C 4 -alkyl or phenyl;

C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, C 3 -C 6 -heterocyclyl, C 3 -C 6 -heterocyclyl-C 1 -C 6 -alkyl, phenyl, phenyl-C 1 -C 4 -alkyl or a 5- or 6-membered heteroaryl,

wherein each phenyl or heteroaryl ring can be substituted by one to four substituents selected from R 14 or a 3- to 7-membered carbocycle,

 which carbocycle optionally has in addition to carbon atoms one or two ring members selected from the group consisting of —N(R 12 )—, —N═N—, —C(═O)—, —O— and —S—, and

 which carbocycle is optionally substituted with one to four substituents selected from R 14 ;

 wherein R 14 is halogen, NO 2 , CN, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkoxy-carbonyl;

R 10 , R 11 independently of one another are R 9 , or together form a 3- to 7-membered carbocycle,

which carbocycle optionally has in addition to carbon atoms one or two ring members selected from the group consisting of —N(R 12 )—, —N═N—, —C(═O)—, —O— and —S—, and

which carbocycle is optionally substituted with one to four substituents selected from R 14 ;

X O or S; and

Y O or S;

or an agriculturally acceptable salt thereof.

2. The compound of claim 1 , wherein R 1 is C 1 -C 4 -haloalkyl.

3. The compound of claim 1 , wherein R 2 is H.

4. The compound of claim 1 , wherein R 3 is F, Cl or Br.

5. The compound of claim 1 , wherein R 6 is H.

6. The compound of claim 1 , wherein R 7 is C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy.

7. The compound of claim 1 , wherein R 8 is OR 9 or NR 9 S(O) 2 R 9 .

8. The compound of claim 1 , which corresponds to the formula (I.a)

wherein R 3 , R 4 , R 7 and R 8 are as defined in claim 1 .

9. A process for the preparation of the compound of claim 1 , wherein an acid chloride (II)

is reacted with a compound (III)

H—R 8   (III),

in the presence of a base, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are as defined in claim 1 .

10. A herbicidal composition comprising an herbicidally active amount of at least one phenylpyridine of formula (I) as claimed in claim 1 and at least one inert liquid and/or solid carrier and, if appropriate, at least one surface-active substance.

11. A process for the preparation of herbicidal active compositions, which comprises mixing an herbicidally active amount of at least one phenylpyridine of formula (I) as claimed in claim 1 and at least one inert liquid and/or solid carrier and, if desired, at least one surface-active substance.

12. A method of controlling undesired vegetation, which comprises allowing an herbicidally active amount of at least one compound of claim 1 to act on plants, their environment or on seed.

13. The method of claim 12 , wherein R 1 is C 1 -C 4 -haloalkyl.

14. The method of claim 12 , wherein R 2 is H.

15. The method of claim 12 , wherein R 3 is F Cl or Br.

16. The method of claim 12 , wherein R 6 is H.

17. The method of claim 12 , wherein R 7 is C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy.

18. The method of claim 12 , wherein R 8 is OR 9 or NR 9 S(O) 2 R 9 .

19. Acid chlorides of formula (II)

wherein the variables have the following meanings:

R 1 halogen, C 1 -C 4 -haloalkyl or SO 2 CH 3 ;

R 2 H, CH 3 or NH 2 ;

R 3 halogen;

R 4 H or halogen;

R 5 halogen or CN;

R 6 H or CH 3 ;

R 7 C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, or C 3 -C 6 -alkynyloxy;

X O or S; and

Y O or S.