Substituted pyridines having a herbicidal effect

1. A compound of the formula I

wherein:

R 1 is O—R A , S(O) n —R A or O—S(O) n —R A ;

R A is hydrogen, C 1 -C 4 -alkyl, Z—C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 2 -C 6 -alkenyl, Z—C 3 -C 6 -cycloalkenyl, C 2 -C 6 -alkynyl, Z-(tri-C 1 -C 4 -alkyl)silyl, Z—C(═O)—R a , Z—NR i —C(O)—NR i R ii , Z—P(═O)(R a ) 2 , NR i R ii , a 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, which may be partially or fully substituted by groups R a and/or R b and which is attached via carbon or nitrogen,

R a is hydrogen, OH, C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, Z—C 3 -C 6 -cycloalkyl, C 2 -C 8 -alkenyl, Z—C 5 -C 6 -cycloalkenyl, C 2 -C 8 -alkynyl, Z—C 1 -C 6 -alkoxy, Z—C 1 -C 4 -haloalkoxy, Z—C 3 -C 8 -alkenyloxy,

Z—C 3 -C 8 -alkynyloxy, NR i R ii , C 1 -C 6 -alkylsulfonyl, Z-(tri-C 1 -C 4 -alkyl)silyl, Z-phenyl, Z-phenoxy, Z-phenylamino or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where the cyclic groups are unsubstituted or substituted by 1, 2, 3 or 4 groups R b ;

R i , R ii independently of one another are hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, Z—C 3 -C 6 -cycloalkyl, Z—C 1 -C 8 -alkoxy, Z—C 1 -C 8 -haloalkoxy, Z—C(═O)—R a , Z-phenyl, a 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S and which is attached via Z; or

R i and R ii together with the nitrogen atom to which they are attached may also form a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S;

Z is a covalent bond or C 1 -C 4 -alkylene;

n is 0, 1 or 2;

R 2 is phenyl substituted by 1, 2, 3 or 4 groups R b ;

R b independently of one another are Z—CN, Z—OH, Z—NO 2 , Z-halogen, C 1 C 8 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, Z—C 1 -C 8 -alkoxy, Z—C 1 -C 8 -halo-alkoxy, Z—C 3 -C 10 -cycloalkyl, O—Z—C 3 -C 10 -cycloalkyl, Z—C(═O)—R a , NR i R ii , Z—(tri-C 1 -C 4 -alkyl)silyl, Z-phenyl and S(O) n R bb ,

where R bb is C 1 -C 8 -alkyl or C 1 -C 6 -haloalkyl;

n is 0, 1 or 2; or

R b together with a second group R b attached to the adjacent carbon atom may form a five- or six-membered saturated or partially or fully unsaturated ring which, in addition to carbon atoms, may contain 1, 2 or 3 heteroatoms selected from the group consisting of O, N and S;

X is O;

Y is O;

E, G, M are C—R c , A is N;

R c is hydrogen or one of the groups mentioned for R b ;

where in the groups R A , and their subsubtituents, the carbon chains and/or the cyclic groups may be partially or fully substituted by groups R b ,

or a N-oxide or an agriculturally suitable salt thereof.

2. The compound of the formula I according to claim 1 in which

R 1 O—R A or S(O) n —R A ; and

R A is hydrogen, C 1 -C 4 -alkyl, Z—C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 2 -C 6 -alkenyl, Z—C 3 -C 6 -cycloalkenyl, C 2 -C 6 -alkynyl, Z-(tri-C 1 -C 4 -alkyl)silyl, Z—C(═O)—R a , Z—P(═O)(R a ) 2 , a 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S which may be partially or fully substituted by groups R a and/or R b and which is attached via C or N,

R a is hydrogen, OH, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, Z—C 3 -C 6 -cycloalkyl, C 2 -C 8 -alkenyl, Z—C 5 -C 6 -cycloalkenyl, C 2 -C 8 -alkynyl, Z—C 1 -C 6 -alkoxy, Z—C 1 -C 4 -haloalkoxy, Z—C 3 -C 8 -alkenyloxy, Z—C 3 -C 8 -alkynyloxy, NR i R ii , C 1 -C 6 -alkylsulfonyl, Z-(tri-C 1 -C 4 -alkyl)silyl, Z-phenyl, Z-phenoxy,

Z-phenylamino or a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle, comprising 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where the cyclic groups are unsubstituted or substituted by 1, 2, 3 or 4 groups R b ;

R i , R ii independently of one another are hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, Z—C 3 -C 6 -cycloalkyl, Z—C 1 -C 8 -alkoxy, or Z—C 1 -C 8 -haloalkoxy; or

R i and R ii together with the nitrogen atom to which they are attached may form a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S.

3. The compound of the formula I according to claim 1 in which R A is hydrogen or C 1 -C 6 -alkylcarbonyl.

4. The compound of the formula I according to claim 1 in which R c is hydrogen.

5. The compound of the formula I according to claim 1 which corresponds to the formula

in which R 5 and R 6 are groups R b , R c is H, and n is zero or an integer from one to four.

6. The compound of claim 5 and in which

R 1 is OH, OCH 3 , OC(O)CH 3 , OC(O)CH 2 CH 3 , OC(O)CH(CH 3 ) 2 , OC(O)C(CH 3 ) 3 , OC(O)-c-C 3 H 5 , OC(O)—C 6 H 5 , OC(O)—CH 2 C 6 H 5 , OC(O)CH 2 Cl, OC(O)—CF 3 , OC(O)—CH 2 OCH 3 , OC(O)—N(CH 3 ) 2 or OC(O)—OCH 2 CH 3 ; and

R 2 is phenyl substituted by a group selected from the group consisting of 2-Br, 2-Cl, 2,4-Cl 2 , 2-Cl-4-F, 2-Cl-5-F, 2-Cl-6-F, 2-Cl-4-CF 3 , 2-Cl-5-CF 3 , 2-Cl-6-CF 3 , 2-Cl-3,6-F 2 , 2-F, 2,4-F 2 , 2,5-F 2 , 2,6-F 2 , 2-F-4-CF 3 , 2-F-5-CF 3 , 2-F-6-CF 3 , 2,3,6-F 3 , 2-NO 2 , 2-NO 2 -4-F, 2-NO 2 -5-F, 2-NO 2 -6-F, 2-NO 2 -4-CF 3 , 2-NO 2 -5-CF 3 , 2-NO 2 -6-CF 3 , 2-NO 2 -3,6-F 2 , 2-CN, 2-CH 3 , 2-CH 3 -4-F, 2-CH 3 -5-F, 2-CH 3 -6-F, 2-CH 3 -4-CF 3 , 2-CH 3 -5-CF 3 , 2-CH 3 -6-CF 3 , 2-CH 3 -3,6-F 2 , 2-OCH 3 , 2-OCH 3 -4-F, 2-OCH 3 -5-F, 2-OCH 3 -6-F, 2-OCH 3 -4-CF 3 , 2-OCH 3 -5-CF 3 , 2-OCH 3 -6-CF 3 , 2-OCH 3 -3,6-F 2 , 2-CHF 2 , 2-CHF 2 -4-F, 2-CHF 2 -5-F, 2-CHF 2 -6-F, 2-CHF 2 -4-CF 3 , 2-CHF 2 -5-CF 3 , 2-CHF 2 -6-CF 3 , 2-CHF 2 -3,6-F 2 , 2-CF 3 , 2-CF 3 -4-F, 2-CF 3 -5-F, 2-CF 3 -6-F, 2-CF 3 -4-CF 3 , 2-CF 3 -5-CF 3 , 2-CF 3 -6-CF 3 , 2-CF 3 -3,6-F 2 , 2-OCHF 2 , 2-OCHF 2 -4-F, 2-OCHF 2 -5-F, 2-OCHF 2 -6-F, 2-OCHF 2 -4-CF 3 , 2-OCHF 2 -5-CF 3 , 2-OCHF 2 -6-CF 3 , 2-OCHF 2 -3,6-F 2 , 2-OCF 3 , 2-OCF 3 -4-F, 2-OCF 3 -5-F, 2-OCF 3 -6-F, 2-OCF 3 -4-CF 3 , 2-OCF 3 -5-CF 3 , 2-OCF 3 -6-CF 3 and 2-OCF 3 -3,6-F 2 .

7. A composition comprising a herbicidally effective amount of at least one pyridine compound of the formula I or an agriculturally suitable salt thereof according to claim 1 and auxiliaries customary for formulating crop protection agents.

8. The composition according to claim 7 which comprises at least one further active compound.

9. The composition according to claim 7 which comprises two further active compounds from the group of the herbicides and/or safeners.

10. A method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one compound of claim 1 to act on plants, their seed and/or their habitat.

11. The method of claim 10 , wherein

R 1 O—R A or S(O) n —R A ; and

R A is hydrogen, C 1 -C 4 -alkyl, Z—C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, Z—C 3 -C 6 -cycloalkenyl, C 2 -C 6 -alkynyl, Z-(tri-C 1 -C 4 -alkyl)silyl, Z—C(═O)—R a , Z—P(═O)(R a ) 2 , a 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S which may be partially or fully substituted by groups R a and/or R b and which is attached via C or N,

R a is hydrogen, OH, C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, Z—C 3 -C 6 -cycloalkyl, C 2 -C 8 -alkenyl, Z—C 5 -C 6 -cycloalkenyl, C 2 -C 8 -alkynyl, Z—C 1 -C 6 -alkoxy, Z—C 1 -C 4 -haloalkoxy, Z—C 3 -C 8 -alkenyloxy, Z—C 3 -C 8 -alkynyloxy, NR i R ii , C 1 -C 6 -alkylsulfonyl, Z-(tri-C 1 -C 4 -alkyl)silyl, Z-phenyl, Z-phenoxy,

Z-phenylamino or a 5- or 6-membered monocyclic or 9-, or 10-membered bicyclic heterocycle, comprising 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S, where the cyclic groups are unsubstituted or substituted by 1, 2, 3 or 4 groups R b ;

R i , R ii independently of one another are hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, Z—C 3 -C 6 -cycloalkyl, Z—C 1 -C 8 -alkoxy, or Z—C 1 -C 8 -haloalkoxy; or

R i and R ii together with the nitrogen atom to which they are attached may form a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle which contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S.

12. The method of claim 10 , wherein R A is hydrogen or C 1 -C 6 -alkylcarbonyl.

13. The method of claim 10 , wherein R c is hydrogen.

14. The method of claim 10 , wherein the compound corresponds to the formula

in which R 5 and R 6 are groups R b and n is zero or an integer from one to four.

15. The method of claim 10 , wherein

R 1 is OH, OCH 3 , OC(O)CH 3 , OC(O)CH 2 CH 3 , OC(O)CH(CH 3 ) 2 , OC(O)C(CH 3 ) 3 , OC(O)-c-C 3 H 5 , OC(O)—C 6 H 5 , OC(O)—CH 2 C 6 H 5 , OC(O)CH 2 Cl, OC(O)—CF 3 , OC(O)—CH 2 OCH 3 , OC(O)—N(CH 3 ) 2 or OC(O)—OCH 2 CH 3 ;

R 2 is phenyl substituted by a group selected from the group consisting of 2-Br, 2-Cl, 2,4-Cl 2 , 2-Cl-4-F, 2-Cl-5-F, 2-Cl-6-F, 2-Cl-4-CF 3 , 2-Cl-5-CF 3 , 2-Cl-6-CF 3 , 2-Cl-3,6-F 2 , 2-F, 2,4-F 2 , 2,5-F 2 , 2,6-F 2 , 2-F-4-CF 3 , 2-F-5-CF 3 , 2-F-6-CF 3 , 2,3,6-F 3 , 2-NO 2 , 2-NO 2 -4-F, 2-NO 2 -5-F, 2-NO 2 -6-F, 2-NO 2 -4-CF 3 ,

2-NO 2 -5-CF 3 , 2-NO 2 -6-CF 3 , 2-NO 2 -3,6-F 2 , 2-CN, 2-CH 3 , 2-CH 3 -4-F, 2-CH 3 -5-F, 2-CH 3 -6-F, 2-CH 3 -4-CF 3 , 2-CH 3 -5-CF 3 , 2-CH 3 -6-CF 3 , 2-CH 3 -3,6-F 2 ,

2-OCH 3 , 2-OCH 3 -4-F, 2-OCH 3 -5-F, 2-OCH 3 -6-F, 2-OCH 3 -4-CF 3 , 2-OCH 3 -5-CF 3 , 2-OCH 3 -6-CF 3 , 2-OCH 3 -3,6-F 2 , 2-CHF 2 , 2-CHF 2 -4-F, 2-CHF 2 -5-F,

2-CHF 2 -6-F, 2-CHF 2 -4-CF 3 , 2-CHF 2 -5-CF 3 , 2-CHF 2 -6-CF 3 , 2-CHF 2 -3,6-F 2 , 2-CF 3 , 2-CF 3 -4-F, 2-CF 3 -5-F, 2-CF 3 -6-F, 2-CF 3 -4-CF 3 , 2-CF 3 -5-CF 3 , 2-CF 3 -6-CF 3 , 2-CF 3 -3,6-F 2 , 2-OCHF 2 , 2-OCHF 2 -4-F, 2-OCHF 2 -5-F, 2-OCHF 2 -6-F, 2-OCHF 2 -4-CF 3 , 2-OCHF 2 -5-CF 3 , 2-OCHF 2 -6-CF 3 , 2-OCHF 2 -3,6-F 2 ,

2-OCF 3 , 2-OCF 3 -4-F, 2-OCF 3 -5-F, 2-OCF 3 -6-F, 2-OCF 3 -4-CF 3 , 2-OCF 3 -5-CF 3 , 2-OCF 3 -6-CF 3 and 2-OCF 3 -3,6-F 2 .