Malonamides and their use as herbicides

1 . An herbicidal compound of formula (I)

wherein the substituents have the following meanings:

R 1 is selected from the group consisting of hydrogen, (C 1 -C 3 )-alkyl, (C 3 -C 4 )-cycloalkyl, (C 1 -C 3 )-haloalkyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, and (C 1 -C 3 )-haloalkoxy;

R 2 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, and (C 1 -C 3 )-haloalkoxy;

R 3 is selected from the group consisting of hydrogen, halogen, nitro, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, hydroxy-(C 1 -C 3 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 3 -C 5 )-halocycloalkyl, hydroxy-(C 3 -C 5 )-cycloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, (C 1 -C 3 )-alkoxycarbonyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, and (C 1 -C 3 )-alkylsulfonyl;

R 4 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 3 -C 4 )-halocycloalkyl, (C 1 -C 3 )-alkoxy (C 1 -C 3 )-haloalkoxy, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-haloalkynyl, and (C 1 -C 3 )-alkylthio;

R 5 is selected from the group consisting of hydrogen, halogen, nitro, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, hydroxy-(C 1 -C 3 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 3 -C 5 )-halocycloalkyl, hydroxy-(C 3 -C 5 )-cycloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, (C 1 -C 3 )-alkoxycarbonyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, and (C 1 -C 3 )-alkylsulfonyl;

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

R 7 is selected from the group consisting of hydrogen, halogen, cyano, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-cyanoalkyl, (C 1 -C 3 )-hydroxyalkyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkoxy-(C 1 -C 3 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, and (C 1 -C 3 )-alkylthio;

R 8 is selected from the group consisting of hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 4 )-cycloalkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-haloalkenyl, (C 2 -C 6 )-alkynyl, (C 2 -C 6 )-haloalkynyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, and (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkoxy;

X is a bond (X 0 ) or a divalent unit selected from the group consisting of (X 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ), and (X 6 ):

R 10 -R 15 , each independently, is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO 2 R e , CONR b R d , NR b CO 2 R e , and R a , or is selected from the group consisting of (C 1 -C 6 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, and cyano, or is selected from the group consisting of (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkoxy, (C 3 -C 6 )-alkenyloxy, (C 3 -C 6 )-alkynyloxy, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, (C 1 -C 3 )-alkylsulfonyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and (C 1 -C 2 )-alkoxy;

Y is hydrogen, cyano, hydroxyl, or Z,

or

is selected from the group consisting of (C 1 -C 12 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 2 -C 12 )-alkenyl, and (C 2 -C 12 )-alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a , SO 2 NR b R d , SO 2 NR b COR e , CO 2 R e , CONR b R h , COR b , CONR e SO 2 R a , NR b R e , NR b COR e , NR b CONR e R e , NR b CO 2 R e , NR b SO 2 R e , NR b SO 2 NR b R e , OCONR b R e , OCSNR b R e , POR f R f , and C(R b )═NOR e ;

Z is a three-, four-, five- or six-membered saturated, partly unsaturated, fully unsaturated or aromatic ring, except phenyl, which is formed from r carbon atoms, o nitrogen atoms, n sulfur atoms, and n oxygen atoms, and which is substituted by m radicals selected from the group consisting of CO 2 R e , CONR b R h , S(O) n R a , SO 2 NR b R d , SO 2 NR b COR e , COR b , CONR e SO 2 R a , NR b R e , NR b COR e , NR b CONR e R e , NR b CO 2 R e , NR b SO 2 R e , NR b SO 2 NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )═NOR e , R b , R c , R e , and R f , and where the sulfur atoms and carbon atoms bear n oxo groups;

R a is selected from the group consisting of (C 1 -C 6 )-alkyl, (C 2 -C 4 )-alkynyl, (C 3 -C 6 )-cycloalkyl, and phenyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C 1 -C 3 )-alkoxy;

R b is hydrogen, (C 1 -C 3 )-alkoxy, or R a ;

R c is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or selected from the group consisting of (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-alkenyloxy, or (C 3 -C 6 )-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C 1 -C 2 )-alkoxy;

R d is hydrogen or is selected from the group consisting of (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 3 )-alkyl, phenyl-(C 1 -C 3 )-alkyl, furanyl-(C 1 -C 3 )-alkyl, and (C 2 -C 4 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO 2 R a , CONR b R h , (C 1 -C 2 )-alkoxy, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, (C 1 -C 3 )-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;

R e is R d ;

R f is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-alkoxy;

R h is hydrogen or is selected from the group consisting of (C 1 -C 6 )-alkyl, (C 1 -C 2 )-alkoxy, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, and (C 2 -C 4 )-alkynyl each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO 2 R a , and (C 1 -C 2 )-alkoxy;

m is 0, 1, 2, 3, 4, or 5;

n is 0, 1, or 2;

o is 0, 1, 2, 3, or 4;

r is 1, 2, 3, 4, 5, or 6;

including their agriculturally acceptable salts, amides, esters, or thioesters, provided the compounds of formula (I) have a carboxyl group.

2 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:

R 1 is hydrogen;

R 8 is hydrogen.

3 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:

R 2 is hydrogen, halogen, or (C 1 -C 3 )-alkyl;

R 6 is hydrogen, halogen, or (C 1 -C 3 )-alkyl.

4 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:

R 3 is halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, or (C 1 -C 3 )-haloalkoxy;

R 5 is hydrogen, halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, or (C 1 -C 3 )-haloalkoxy.

5 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:

R 4 is hydrogen or halogen.

6 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:

R 7 is selected from the group consisting of hydrogen, halogen, cyano, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-haloalkyl, and (C 1 -C 3 )-hydroxyalkyl.

7 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:

X is a bond.

8 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:

X is a bond;

Y is selected from the group consisting of (C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 8 )-alkenyl, and (C 2 -C 8 )-alkynyl, each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a , SO 2 NR b R d , SO 2 NR b COR e , CO 2 R e , CONR b R h , COR b , CONR e SO 2 R a , NR b R e , NR b COR e , NR b CONR e R e , NR b CO 2 R e , NR b SO 2 R e NR b SO 2 NR b R e , OCONR b R e , OCSNR b R e , POR f R f , and C(R b )═NOR e .

9 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:

X is a bond;

Y is Z;

Z is a four- or five-membered saturated or partly unsaturated ring, which is formed from r carbon atoms and n oxygen atoms, each substituted by m radicals selected from the group consisting of CO 2 R e , CONR b R h , CONR e SO 2 R a , R b , R c , R e , and R f .

10 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:

X is a bond;

Y is Z or (C 1 -C 8 )-alkyl, which is substituted by m radicals selected from the group consisting of CO 2 R e ;

Z is a five-membered saturated or partly unsaturated carbocycle, which is substituted by m radicals selected from the group consisting of CO 2 R e .

11 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:

R 1 is selected from the group consisting of hydrogen, (C 1 -C 3 )-alkyl, (C 3 -C 4 )-cycloalkyl, (C 1 -C 3 )-haloalkyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, and (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy;

R 2 is selected from the group consisting of hydrogen, halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, and (C 1 -C 3 )-haloalkoxy;

R 3 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 3 -C 5 )-halocycloalkyl, (C 1 -C 3 )-haloalkoxy, (C 2 -C 3 )-haloalkenyl, and (C 2 -C 3 )-haloalkynyl;

R 4 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 3 -C 4 )-halocycloalkyl, (C 1 -C 3 )-haloalkoxy, (C 2 -C 3 )-haloalkenyl, and (C 2 -C 3 )-haloalkynyl;

R 5 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 3 -C 5 )-halocycloalkyl, (C 1 -C 3 )-haloalkoxy, (C 2 -C 3 )-haloalkenyl, and (C 2 -C 3 )-haloalkynyl;

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

R 7 is selected from the group consisting of hydrogen, halogen, cyano, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-haloalkyl, and (C 1 -C 3 )-hydroxyalkyl;

R 8 is hydrogen, (C 1 -C 6 )-alkyl, or (C 3 -C 6 )-cycloalkyl;

X is a bond;

Y is Z, or is selected from the group consisting of (C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 5 )-alkenyl, and (C 2 -C 8 )-alkynyl, each substituted by m radicals selected from the group consisting of fluorine, CO 2 R e , and CONR e SO 2 R a ;

Z is a four to five-membered saturated or partly unsaturated ring which is formed from r carbon atoms and n oxygen atoms, and which is substituted by m radicals selected from the group consisting of CO 2 R e , CONR b R h , CONR e SO 2 R a , R b , R c , R e , and R f ;

R a is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, or phenyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and hydroxy;

R b is hydrogen, or is (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and hydroxy;

R c is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-alkenyloxy, and (C 3 -C 6 )-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C 1 -C 2 )-alkoxy;

R e is hydrogen or is selected from the group consisting of (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, phenyl-(C 1 -C 3 )-alkyl, and (C 2 -C 4 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C 1 -C 2 )-alkoxy;

R f is (C 1 -C 3 )-alkyl or (C 1 -C 3 )-alkoxy;

R h is hydrogen or is selected from the group consisting of (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, and (C 2 -C 4 )-alkynyl each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C 1 -C 2 )-alkoxy;

m is 0, 1, 2, 3, 4, or 5;

n is 0, 1, or 2;

r is 1, 2, 3, 4, or 5.

12 . A composition comprising at least one herbicidal compound as claimed in claim 1 , and at least one auxiliary, which is customary for formulating crop protection compounds.

13 . The composition as claimed in claim 12 , comprising a further herbicide.

14 . A method for controlling unwanted vegetation in a crop which comprises applying an herbicidally effective amount of at least one herbicidal compound as claimed in claim 1 to crop plants, their seed, and/or their habitat.