Herbicidal malonamides

A compound of formula (I)

• wherein the substituents have the following meanings:
• 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 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, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C1-C3)-haloalkoxycarbonyl, (C1-C3)-alkylthio, (C1-C3)-haloalkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-haloalkylsulfinyl, (C1-C3)-alkylsulfonyl, or (C1-C3)-haloalkylsulfonyl;
• R4 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C3-C4)-cycloalkyl, (C3-C4)-halocycloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, or (C1-C3)-alkylthio;
• 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, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy, (C1-C3)-alkoxycarbonyl, (C1-C3)-haloalkoxycarbonyl, (C1-C3)-alkylthio, (C1-C3)-haloalkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)-haloalkylsulfinyl, (C1-C3)-alkylsulfonyl, or (C1-C3)-haloalkylsulfonyl;
• R6 is hydrogen, halogen, hydroxyl, cyano, (C1-C3)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, or (C1-C3)-haloalkoxy;
• R7 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, or (C2-C6)-alkynyl, where the four last-mention aliphatic and cycloaliphatic radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, and cyano;
• R8 is hydrogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C4)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C1-C3)-alkoxy-(C1-C3)-alkyl, (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 and R11, 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-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;
• (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, or (C1-C3)-alkylsulfonyl, where the aliphatic or cycloaliphatic moieties of the seven last-mentioned radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and (C1-C2)-alkoxy;
• R12 to R15, independently of each other and independently of each occurrence, are hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2Rc, CONRbRd, NRbCO2Re, Ra, (C1-C6)-alkyl, (C3-C5)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, phenyl, imidazolyl, where the six last-mentioned aliphatic, cycloaliphatic, aromatic and heteroaromatic radicals are each substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano;
• (C1-C6)-alkoxy, (C3-C6)-cycloalkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, or (C1-C3)-alkylsulfonyl, where the aliphatic or cycloaliphatic moieties of the seven last-mentioned radicals are each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, and (C1-C2)-alkoxy;
• Y is 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 Rb, Rc, Re, and Rf;
• and are further substituted by p radicals selected from the group consisting of CO2Re, CONRbRh, S(O)nRa, S(O)2NRbRd, SO2NRbCORe, CORb, CONReS(O)Ra, CONReS(O)2Ra, CONRb1S(O)2NRb2Rb3, NRbRe, NRbCORe, NRbCONReRe, NRbCO2Re, NRbS(O)2Re, NRb1SO2NRb2Rb3, OC(O)NRbRe, OC(S)NRbRe, 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, n nitrogen atoms, n sulfur atoms, and n oxygen atoms, and which is substituted by m radicals selected from the group consisting of Rb, Rc, Re, and Rf and p radicals from the group consisting of CO2Re, CONRbRh, S(O)nRa, SO2NRbRd, SO2NRbCORe, CORb, CONReS(O)Ra, CONReSO2Ra, CONRb1SO2NRb2Rb3, NRbRe, NRbCORe, NRbCONReRe, NRbCO2Re, NRbSO2Re, NRb1SO2NRb2Rb3, OCONRbRe, OCSNRbRe, PORfRf, and C(Rb)═NORe, 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;
• Rb, Rb1, and Rb2, independently of each other and independently of each occurrence, are hydrogen or have one of the meanings given for Ra;
• each Rb3 has independently one of the meanings given for Rd;
• or
• Rb2 and Rb3, together with the nitrogen atom they are bound to, form a saturated 3-, 4-, 5-, 6-, or 7-membered N-bound heterocyclic ring which optionally contains one further heteroatom or heteroatom group selected from the group consisting of N, O, S, S(O)1 and S(O)2 as ring member;
• each Rc is independently fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O)nRa, or (C1-C6)-alkoxy, (C2-C6)-alkenyloxy or (C2-C6)-alkynyloxy, where the aliphatic or cycloaliphatic moieties of 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, (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 each of the seven last-mentioned radicals 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;
• each Re has independently one of the meanings given for Rd;
• each Rf is independently (C1-C3)-alkyl or (C1-C3)-alkoxy;
• 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 each of the six last-mentioned radicals is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO2Ra, and (C1-C2)-alkoxy;
• each m is independently 0, 1, 2, 3, 4, or 5;
• each n is independently 0, 1, or 2;
• each p is independently 1, 2, or 3;
• r is 1, 2, 3, 4, 5, or 6;
• including agriculturally acceptable salts, stereoisomers, and tautomers;
• except for
• 2-methyl-N1-phenyl-N3-[1-[(2-phenylacetyl)amino]ethyl]propanediamide;
• carbamic acid [(2S,3S)-3-hydroxy-2-[[2-methyl-1,3-dioxo-3-[[3-(trifluoro-methyl)phenyl]amino]propyl]amino]4-hexynyl]-phenylmethylester;
• 2-methyl-N-phenyl-N′-[1-[(2-phenylacetyl)amino]ethyl]propanediamide;
• {(2S,3S)-3-hydroxy-2-[2-(3-trifluoromethyl-phenylcarbamoyl)-propionylamino]-hex-4-ynyl}-carbamic acid benzyl ester.