Herbicidal malonamides

A compound of formula (I)

• wherein the substituents have the following meanings:
• R1 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, (C1-C3)-haloalkoxy;
• R2 hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy;
• R3 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, (C1-C3)-alkylsulfonyl;
• R4 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, (C1-C3)-alkylthio;
• R5 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, (C1-C3)-alkylsulfonyl;
• R6 hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy;
• R7 (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano;
• R8 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, (C3-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C1-C6)-haloalkoxy, (C1-C3)-cyanoalkoxy, (C1-C3)-alkoxy-(C1-C3)-alkoxy, (C3-C5)-cycloalkyl-(C1-C3)-alkoxy, (C3-C6)-alkenyloxy, (C3-C6)-alkynyloxy, (C1-C3)-alkylthio;
• R9 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, (C1-C3)-alkoxy-(C1-C3)-alkoxy;
• X a bond (X0) or a divalent unit from the group consisting of (X1), (X2), (X3), (X4), (X5), and (X6):
• R10-R15 each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2Re, CONRbRd, NRbCO2Re, Ra, or (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, phenyl, imidazolyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano, or (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 from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C2)-alkoxy;
• Y hydrogen, cyano, hydroxyl, Z,
• or
• (C1-C12)-alkyl, (C3-C8)-cycloalkyl, (C2-C12)-alkenyl or (C2-C12)-alkynyl, each substituted by m radicals 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 a three-, four-, five- or six-membered saturated, partly unsaturated, fully unsaturated or aromatic ring, except phenyl, which is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and which is substituted by m radicals 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 (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;
• Rb hydrogen or Ra;
• Rc fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O)nRa or (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 hydrogen or (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C4)-alkenyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, phenyl-(C1-C3)-alkyl, furanyl-(C1-C3)-alkyl or (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 henylsulfonyl;
• Re Rd;
• Rf (C1-C3)-alkyl or (C1-C3)-alkoxy;
• Rh hydrogen or (C1-C6)-alkyl, (C1-C2)-alkoxy, (C3-C6)-cycloalkyl, (C2-C4)-alkenyl, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl, or (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 0, 1, 2, 3, 4 or 5;
• n 0, 1 or 2;
• r 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.