Herbicidal malonamides

A compound of formula (I)

• wherein the substituents have the following meanings:
• R1 is hydrogen, (C1-C3)-alkyl, (C3-C4)-cycloalkyl, (C1-C3)-haloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkoxy, or (C1-C3)-haloalkoxy;
• R2 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, or (C1-C3)-haloalkoxy;
• R3 is hydrogen, halogen, nitro, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)haloalkoxy, (C1-C3)-alkoxycarbonyl, (C2-C3) alkenyl, (C2-C3)haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, or (C1-C3)-alkylsulfonyl;
• R4 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-cycloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-haloalkoxy, (C2-C3)alkenyl, (C2-C3)-haloalkenyl (C2-C3)-alkynyl, or (C2-C3)-haloalkynyl;
• R5 is hydrogen, halogen, nitro, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)haloalkoxy, (C1-C3)-alkoxycarbonyl, (C2-C3) alkenyl, (C2-C3)haloalkenyl, (C2-C3) alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, or (C1-C3)-alkylsulfonyl;
• R6 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, or (C1-C3)-haloalkoxy;
• R7 and R8 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 heterocyclic ring W, containing, in addition to this carbon atom, q carbon atoms, u oxygen atoms, v nitrogen atoms, w sulfur atoms, and x elements selected from the group consisting of NRd, NCORd, and NC(O)ORd, where one carbon ring atom bears p oxo groups, and where the ring is substituted by n radicals Rg;
• R9 is hydrogen, (C1-C6)-alkyl, (C3-C4)-cycloalkyl, (C1-C6)-haloalkyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)alkynyl, (C2-C6)-haloalkynyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, or (C1-C3)-alkoxy-(C1-C3)-alkoxy;
• X is a bond (X0) or a divalent unit selected from the group consisting of (X1), (X2), (X3), (X4), (X5), and (X6):
• R10, R11, R12, R13, R14, and R15, independently of each other and independently of each occurrence, are hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2Re, CONRbRd, Ra,
• or (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, where the four last-mentioned aliphatic and cycloaliphatic radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, and cyano;
• or (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C3-C6)-alkenyloxy or (C3-C6)alkynyloxy, where the aliphatic and cycloaliphatic moieties in the four last-mentioned radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and (C1-C2)-alkoxy;
• Y is hydrogen, cyano, hydroxyl, Z,
• or is
• (C1-C12)-alkyl, (C3-C8)-cycloalkyl, (C2-C12)-alkenyl, or (C2-C12)-alkynyl, where the four last-mentioned aliphatic and cycloaliphatic radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, ORd, Z, OZ, NHZ, S(O)nRa, SO2NRbRd, SO2NRbCORe, CO2Re, CONRbRh, CORb, CONReSO2Ra, NRbRe, NRbCORe, NRbCONReRe, NRbCO2Re, NRbSO2Re, NRbSO2NRbRe, OCONRbRe, OCSNRbRe, PORfRf, and C(Rb)═NORe;
• Z is a three-, four-, five-, six-, seven- or eight-membered saturated, partly unsaturated, fully unsaturated or aromatic monocyclic, bicyclic, or polycyclic ring, except phenyl, which is formed from r carbon atoms, k nitrogen atoms, n sulfur atoms, and n oxygen atoms, and which is substituted by m radicals selected from the group consisting of CO2Re, CONRbRh, S(O)nRa, SO2NRbRd, SO2NRbCORe, CORb, CONReSO2Ra, NRbRe, NRbCORe, NRbCONReRe, NRbCO2Re, NRbSO2Re, NRbSO2NRbRe, OCONRbRe, OCSNRbRe, PORfRf, and C(Rb)═NORe, Rb, Rc, Re and Rf, and where the sulfur and carbon ring atoms bear n oxo groups;
• each Ra is independently (C1-C6)-alkyl, (C2-C4)-alkynyl, or (C3-C6)-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C1-C3)-alkoxy;
• each Rb is independently hydrogen or has one of the meanings given for Ra;
• each Rc is independently fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O)nRa, or (C1-C6)-alkoxy, (C3-C6)-alkenyloxy or (C3-C6)-alkynyloxy, where the aliphatic and cycloaliphatic moieties in the three last-mentioned radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C1-C2)-alkoxy;
• each Rd is independently hydrogen or (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, (C2-C4)-alkenyl, phenyl-(C1-C3)-alkyl, or (C2-C4)-alkynyl, where the six last-mentioned radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, COORa, (C1-C2)-alkoxy, (C1-C3)alkylsulfinyl, (C1-C3)-alkylsulfonyl, (C1-C3)-alkylthio, phenylsulfinyl, phenylsulfonyl, and phenylthio, where the aliphatic or aromatic moieties in the seven last-mentioned radicals are each substituted with m radicals selected from the group consisting of fluorine, chlorine, and bromine;
• and a 5- or 6-membered heteroaromatic ring containing 1, 2, or 3 heteroatoms selected from N, O, and S as ring members;
• each Re is independently hydrogen or (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, (C2-C4)-alkenyl, phenyl-(C1-C3)-alkyl, or (C2-C4)-alkynyl, where the six last-mentioned radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, COORa, (C1-C2)-alkoxy, (C1-C3)alkylsulfinyl, (C1-C3)-alkylsulfonyl, (C1-C3)-alkylthio, phenylsulfinyl, phenylsulfonyl, and phenylthio, where the aliphatic or aromatic moieties in the seven last-mentioned radicals are each substituted with m radicals selected from the group consisting of fluorine, chlorine, and bromine;
• and a 5- or 6-membered heteroaromatic ring containing 1, 2, or 3 heteroatoms selected from N, O and S as ring members;
• each Rf is independently (C1-C3)-alkyl or (C1-C3)-alkoxy;
• each Rg is independently halogen, nitro, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C5)-cycloalkyl, (C3-C5)halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)haloalkoxy, (C1-C3)-alkoxycarbonyl, (C2-C3) alkenyl, (C2-C3)haloalkenyl, (C2-C3) alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, or (C1-C3)-alkylsulfonyl;
• or two Rg, bound on the same carbon atom, form together a methylene group (═CH2);
• each Rh is independently hydrogen or (C1-C6)-alkyl, (C1-C2)-alkoxy, (C3-C6)cycloalkyl, (C2-C4)-alkenyl, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl, or (C2-C4)-alkynyl, where the six last-mentioned radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C1-C2)-alkoxy;
• k is 0, 1, 2, 3, or 4;
• each m is independently 0, 1, 2, 3, 4, or 5;
• each n is independently 0, 1, or 2;
• p is 0 or 1;
• q is 1, 2, 3, 4, 5, or 6;
• r is 1, 2, 3, 4, 5, 6, 7, or 8;
• u is 0, 1, or 2;
• v is 0, 1, 2, or 3;
• w is 0, 1, or 2;
• x is 0, 1, or 2;
• with the proviso that at least one of u, v, w, and x is not 0;
• including agriculturally acceptable salts, stereoisomers, and tautomers thereof.