Herbicidal malonamides containing a condensed ring system

A compound of formula (I)

• wherein substituents have the following meanings:
• Q is a bicyclic or tricyclic aromatic or partially aromatic condensed ring system formed from s carbon atoms, t nitrogen atoms, n sulfur atoms, and n oxygen atoms, where the carbon or sulfur ring atoms bear p oxo groups and where the ring carries k substituents RQ1 and n substituents RQ2;
• RQ1 is halogen, nitro, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, hydroxy-(C1-C3)-alkyl, (C3-C8)-cycloalkyl, (C1-C3)-alkoxy, (C1-C3)haloalkoxy, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, or (C2-C3)-haloalkynyl;
• RQ2 is phenyl-(C1-C3)-alkyl, (C1-C4)-alkylcarbonyl, aminocarbonyl, (C1-C4)alkylaminocarbonyl, di-(C1-C4-alkyl)aminocarbonyl, (C1-C4)alkoxycarbonyl, benzyloxycarbonyl, fluorenyloxycarbonyl, allyloxycarbonyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-alkylsulfonyl, or phenylsulfonyl, where aliphatic or aromatic moieties in the 14 last-mentioned radicals are substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C1-C2)-alkoxy;
• R1 is hydrogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, or (C1-C3)-alkoxy-(C1-C3)-alkoxy;
• R2 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl, or (C1-C3)-alkoxy-(C1-C3)-alkyl, where aliphatic or cycloaliphatic moieties in the 5 last-mentioned radicals are substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, and cyano;
• R3 is hydrogen, halogen, cyano, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)cyanoalkyl, (C1-C3)-hydroxyalkyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (C1-C3)haloalkoxy-(C1-C3)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C2-C6)alkynyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C3)-cyanoalkoxy, (C1-C3)-alkoxy-(C1-C3)-alkoxy, (C3-C6)-cycloalkoxy, (C3-C8)-cycloalkyl-(C1-C3)-alkoxy, (C3-C6)-alkenyloxy, (C3-C6)-alkynyloxy, or (C1-C3)-alkylthio;
• R4 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C3)-alkoxy-(C1-C3)alkyl, (C3-C4)-cycloalkyl, (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):
• R5, R6, R7, R8, R9, and R10, independently of each other and independently of each occurrence, are hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2Re, CONRbRd, NRbCO2Re, Ra;
• (C1-C6)-alkyl, (C3-C8)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, phenyl, imidazolyl, where the 6 last-mentioned aliphatic, cycloaliphatic, aromatic or heteroaromatic radicals are substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, and cyano;
• (C1-C6)-alkoxy, (C3-C6)cycloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-alkynyloxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, or (C1-C3)-alkylsulfonyl, where aliphatic or cycloaliphatic moieties in the 7 last-mentioned radicals are 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;
• (C1-C12)-alkyl, (C3-C8)-cycloalkyl, (C2-C12)-alkenyl or (C2-C12)-alkynyl, where the 4 last-mentioned aliphatic or cycloaliphatic radicals are 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, Ra, Rc, Re, and Rf, and where the sulfur and carbon ring atoms bear n oxo groups;
• Ra is (C1-C6)-alkyl, (C2-C4)-alkynyl, or (C3-C6)-cycloalkyl, where the 3 last-mentioned aliphatic or cycloaliphatic radicals are substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C1-C3)-alkoxy;
• Rb is hydrogen or independently has one of the meanings given for Ra;
• Rc is fluorine, chlorine, bromine, iodine, cyano, hydroxyl;
• (C1-C6)-alkoxy, (C3-C6)-alkenyloxy, or (C3-C6)-alkynyloxy, where the aliphatic moieties in the 3 last-mentioned radicals are substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, and (C1-C2)-alkoxy;
• Rd is hydrogen, (C1-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C3-C6)cycloalkyl, (C3-C6)-cycloalkyl-(C1-C3)-alkyl, phenyl-(C1-C3)-alkyl or furanyl-(C1-C3)-alkyl, where aliphatic, cycloaliphatic, aromatic or heteroaromatic moieties in the 7 last-mentioned radicals are 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 independently has one of the meanings given for Rd;
• Rf is (C1-C3)-alkyl or (C1-C3)-alkoxy;
• Rh is hydrogen, (C1-C6)-alkyl, (C1-C2)-alkoxy, (C3-C6)-cycloalkyl, (C2-C4)alkenyl, (C2-C4)-alkynyl or (C1-C6)-alkoxycarbonyl-(C1-C6)-alkyl, where aliphatic or cycloaliphatic moieties in the 6 last-mentioned radicals are substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO2Ra, and (C1-C2)alkoxy;
• each k is independently 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;
• each p is independently 0, 1, or 2;
• each r is independently 1, 2, 3, 4, 5, 6, 7, or 8;
• each s is independently 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14;
• each t is independently 0, 1, 2, 3, or 4;
• and agriculturally acceptable salts, stereoisomers, and tautomers thereof;
• except for following compounds:
• N-[(S)-5-(2-hydroxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-2-methoxy-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide;
• 2-ethoxy-N-[(S)-5-(2-hydroxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-N′-(2,2,3,3,3-pentafluoro-propyl)malonamide;
• (S or R)-2-Ethoxy-N-[(S)-5-(2-hydroxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-N′-(2,2,3,3,3-pentafluoro-propyl)malonamide;
• 2-Methoxy-N-[(S)-5-(2-methoxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-N′-(2,2,3,3,3-pentafluoro-propyl)malonamide;
• N-((6R,7S)-2-fluoro-6-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-azabenzocyclohepten-7-yl)-2-methoxy-N′-(2,2,3,3,3-pentafluoro-propyl)malonamide;
• 2-methoxy-N-((6R,7S)-6-methyl-8-oxo-3-trifluoromethyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide;
• (−)-2-methoxy-N-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide;
• N-((S)-5-cyclopropylmethyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-2-methoxy-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide;
• 2-methoxy-N-((S)-5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide;
• and agriculturally acceptable salts, stereoisomers, and tautomers thereof.