Malonamides and their use as herbicides

An herbicidal compound of formula (I)

• wherein the substituents have the following meanings:
• R1 is selected from the group consisting of 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, and (C1-C3)-haloalkoxy;
• R2 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, and (C1-C3)-haloalkoxy;
• R3 is selected from the group consisting of 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, and (C1-C3)-alkylsulfonyl;
• R4 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-alkoxy (C1-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl, and (C1-C3)-alkylthio;
• R5 is selected from the group consisting of 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, and (C1-C3)-alkylsulfonyl;
• R6 is selected from the group consisting of hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, and (C1-C3)-haloalkoxy;
• R7 is selected from the group consisting of hydrogen, halogen, cyano, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl, (C1-C6)-cyanoalkyl, (C1-C3)-hydroxyalkyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-haloalkoxy-(C1-C3)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, and (C1-C3)-alkylthio;
• R8 is selected from the group consisting of 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, and (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-R15, each independently, is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2Re, CONRbRd, NRbCO2Re, and Ra, or is selected from the group consisting of (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-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 (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-alkynyloxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, 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, or Z,
• or
• is selected from the group consisting of (C1-C12)-alkyl, (C3-C5)-cycloalkyl, (C2-C12)-alkenyl, and (C2-C12)-alkynyl, 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- 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 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 atoms and carbon atoms bear n oxo groups;
• Ra is selected from the group consisting of (C1-C6)-alkyl, (C2-C4)-alkynyl, (C3-C6)-cycloalkyl, and phenyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C1-C3)-alkoxy;
• Rb is hydrogen, (C1-C3)-alkoxy, or Ra;
• Rc is selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O)nRa or selected from the group consisting of (C1-C6)-alkoxy, (C3-C6)-alkenyloxy, or (C3-C6)-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C1-C2)-alkoxy;
• Rd is hydrogen or is selected from the group consisting of (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C4)-alkenyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, phenyl-(C1-C3)-alkyl, furanyl-(C1-C3)-alkyl, and (C2-C4)-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO2Ra, CONRbRh, (C1-C2)-alkoxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;
• Re is Rd;
• Rf is (C1-C3)-alkyl or (C1-C3)-alkoxy;
• Rh is hydrogen or is selected from the group consisting of (C1-C6)-alkyl, (C1-C2)-alkoxy, (C3-C6)-cycloalkyl, (C2-C4)-alkenyl, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl, and (C2-C4)-alkynyl each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO2Ra, and (C1-C2)-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.