Herbicidal malonamides
The present invention relates to malonamide compounds of the formula (I) wherein the variables are as defined in the claims and the description, and to compositions comprising these compounds. The invention also relates to the use of said malonamide compounds or the corresponding compositions for controlling unwanted vegetation. Furthermore, the invention relates to methods for controlling unwanted vegetation wherein said malonamide compounds or the corresponding compositions are applied.
1 . A compound of formula (I)
wherein the substituents have the following meanings:
R 1 is 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, or (C 1 -C 3 )-haloalkoxy;
R 2 is hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, or (C 1 -C 3 )-haloalkoxy;
R 3 is 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, or (C 1 -C 3 )-alkylsulfonyl;
R 4 is 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, or (C 2 -C 3 )-haloalkynyl;
R 5 is 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, or (C 1 -C 3 )-alkylsulfonyl;
R 6 is hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, or (C 1 -C 3 )-haloalkoxy;
R 7 and R 8 form, together with the carbon atom to which they are bound, a saturated or partially unsaturated three-, four-, five-, six-, seven- or eight-membered monocyclic or bicyclic carbocyclic ring W, where one carbon ring atom bears p oxo groups, and where the ring is substituted by n radicals R g ;
R 9 is 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, or (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkoxy;
X is a bond; and Y is (C 1 -C 6 )-alkyl substituted by a radical CO 2 R e ; where R e is hydrogen or (C 1 -C 4 )-alkyl; or
X is a bond or a group CH 2 ; and Y is Z, where
Z is a three-, four-, five-, six- or seven-membered saturated or partly unsaturated carbocyclic ring which is substituted by a radical CO 2 R e ;
where R e is hydrogen or (C 1 -C 4 )-alkyl;
each R g is independently 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, (C 1 -C 3 )-alkylsulfonyl;
each n is independently 0, 1 or 2;
each p is independently 0 or 1;
including their agriculturally acceptable salts, stereoisomers and tautomers;
except for following compounds:
glycine, N-[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]-;
L-alanine, N-[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]-;
D-alanine, N-[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl];
D-leucine, N-[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]-;
butanoic acid, 4-[[[1-[[4-fluorophenyl)amino)carbonyl]cyclopropyl]carbonyl]methylamino]-;
β-alanine, N-[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]-N-methyl-;
heptanoic acid, 7-[[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]amino]-;
cyclohexanecarboxylic acid, 4-[[[1-[[(4-fluorophenyl)amino]carbonyl]cyclopropyl]carbonyl]amino].
2 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:
R 1 is hydrogen;
R 9 is hydrogen.
3 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:
R 2 is hydrogen, halogen, (C 1 -C 3 )-alkyl;
R 6 is hydrogen, halogen, (C 1 -C 3 )-alkyl.
4 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:
R 3 is hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy or (C 1 -C 3 )-haloalkoxy;
R 5 is hydrogen, halogen, hydroxyl, cyano, or (C 1 -C 3 )-alkyl.
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 and R 8 form, together with the carbon atom to which they are bound, a saturated or partially unsaturated three-, four- or five-membered monocyclic carbocyclic ring W.
7 . The compound as claimed in claim 1 , where
X is a bond and Z is a five-membered partly unsaturated carbocyclic ring which is substituted by a radical CO 2 R e ; where R e is hydrogen or (C 1 -C 4 )-alkyl.
8 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:
R 1 is hydrogen;
R 2 is hydrogen;
R 3 is hydrogen, halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy or (C 1 -C 3 )-haloalkoxy;
R 4 is hydrogen;
R 5 is hydrogen or halogen;
R 6 is hydrogen;
R 7 and R 8 form, together with the carbon atom to which they are bound, a saturated or partially unsaturated three-, four- or five-membered monocyclic carbocyclic ring W;
R 9 is hydrogen;
X is a bond or a group (X 1 ), where R 10 and R 11 are each independently hydrogen or methyl;
Y is Z, or (C 1 -C 8 )-alkyl substituted by a radical CO 2 R e ;
Z is a three-, four-, five-, six- or seven-membered saturated or partly unsaturated carbocyclic ring which is substituted by a radical CO 2 R e ; and
R e is hydrogen or (C 1 -C 4 )-alkyl.
9 . The compound as claimed in claim 1 , wherein the substituents have the following meaning:
R 1 is hydrogen;
R 2 is hydrogen;
R 3 is halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy or (C 1 -C 3 )-haloalkoxy;
R 4 is hydrogen;
R 5 is hydrogen or halogen;
R 6 is hydrogen;
R 7 and R 8 form, together with the carbon atom to which they are bound, a saturated or partially unsaturated three-, four- or five-membered monocyclic carbocyclic ring W;
R 9 is hydrogen;
X is a bond;
Y is Z, or C(R 101 )(R 111 )—C 1 -C 4 -alkyl substituted by a radical CO 2 R e ;
Z is a five-membered saturated or partly unsaturated carbocyclic ring which is substituted by a radical CO 2 R e ;
R e is hydrogen or (C 1 -C 4 )-alkyl; and
one of R 101 and R 111 is hydrogen and the other is hydrogen or methyl.
10 . A composition comprising at least one compound as claimed in claim 1 , and at least one auxiliary, which is customary for formulating crop protection compounds.
11 . The composition as claimed in claim 10 , comprising a further herbicide.
12 . A method for controlling unwanted vegetation which comprises contacting plants, their seed, and/or their habitat with a herbicidally effective amount of at least one compound as claimed in claim 1 .