Novel herbicides
AssigneesChristoph LUTHY, Andrew EDMUNDS, Renaud BEAUDEGNIES, Sebastian WENDERBORN, Jurgen SCHAETZER, William LUTZ
InventorsChristoph Luthy, Andrew Edmunds, Renaud Beaudegnies, Sebastian Wendeborn, Jurgen Schaetzer, William Lutz
Life of this patent
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Abstract
Compounds of formula (I) wherein the substituents are as defined in claim 1, and agronomically acceptable salts/N-oxides/isomers/enantiomers of those compounds are suitable for use as herbicides.
Claims4
A compound of formula I
- wherein
- R1 is -L10-R4, -L11-X1—R5, —NR6R7, —X2—R8 or —X3-L1-R9;
- L2, L4, L6 and L8 are each independently of the others C1-C4alkylene which may be substituted once, twice or three times by C1-C4alkyl, halogen or by C1-C4alkoxy and to which C1-C4alkylene group there may additionally be spirocyclically bound a C2-C5alkylene group, and wherein that C2-C5alkylene group may in turn be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and/or substituted by C1-C4alkyl or by C1-C4alkoxy;
- L3, L5, L7 and L9 are each independently of the others C1-C4alkylene which may be substituted once, twice or three times by C1-C4alkyl, halogen or by C1-C4alkoxy;
- R2 is halogen, C1-C4haloalkyl, cyano, C1-C3haloalkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl or C1-C4haloalkylsulfonyl;
- L10 is a direct bond or a C1-C6alkylene, C2-C6alkenylene or C2-C6alkynylene group which may be substituted once, twice or three times by C1-C6alkyl, halogen, hydroxy, C1-C6alkoxy, C3-C6cycloalkyloxy, C1-C6alkoxy-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy-C1-C6alkoxy or by C1-C2alkylsulfonyloxy;
- R4 is halogen, cyano, rhodano, C1-C6alkoxycarbonyl, C3-C6alkenyloxycarbonyl, C3-C6alkynyl-oxycarbonyl, benzyloxycarbonyl, C(O)NR25aR26a, formyl, C1-C6alkylcarbonyl, C1-C6haloalkylcarbonyl, C1-C4alkoxy-C1-C4alkylcarbonyl, C1-C4alkoxy-C1-C4alkoxy-C1-C4alkylcarbonyl, N—(C1-C4alkyl)-C1-C4alkylsulfonylamino-C1-C4alkylcarbonyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6-haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C1-C6alkylsulfonyloxy or phenylsulfonyloxy, wherein the phenyl groups may be substituted by one or more C1-C6alkyl, C1-C6-haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxy or nitro groups;
- or R4 is a three- to ten-membered, monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and which may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, and wherein the ring system may contain not more than 2 oxygen atoms and not more than two sulfur atoms, and each ring system may itself be substituted once, twice or three times by C1-C6alkyl, C1-C6haloalkyl, C1-C4alkoxy-C1-C2alkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, hydroxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di(C1-C2alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl or by benzylthio, and wherein phenyl and benzylthio may in turn be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituent on the nitrogen in the heterocyclic ring are other than halogen;
- or R4 is hydrogen when L10 is a C1-C6alkylene group which may be substituted once, twice or three times by C1-C6alkyl or by halogen;
- or when L10 is a C2-C6alkenylene or C2-C6alkynylene group which may be substituted once, twice or three times by C1-C6alkyl, halogen, hydroxy, C1-C6alkoxy, C3-C6cycloalkyloxy, C1-C6alkoxy-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy-C1-C6-alkoxy or by C1-C2alkylsulfonyloxy;
- R25a is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R26a is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R25a together with R26a and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- L11 is a C1-C6alkylene, C2-C6alkenylene or C2-C6alkynylene group which may be substituted once, twice or three times by halogen, hydroxy, C1-C6alkoxy, C3-C6cycloalkyloxy, C1-C6-alkoxy-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy-C1-C6alkoxy or by C1-C2alkylsulfonyloxy;
- X1 is oxygen, —OC(O)—, —C(O)—, —C(═NR14a)—, —C(O)O—, —C(O)NR14b—, —OC(O)O—, —N(R10)—O—, —O—NR11—, thio, sulfinyl, sulfonyl, —SO2NR12—, —NR13SO2—, —N(SO2R14c)—, —N(R14d)C(O)— or —NR14—;
- R10, R11, R12, R13, R14b, R14d and R14 are each independently of the others hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1-C6alkyl substituted by C1-C6alkoxy, or benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted once, twice or three times by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxy or by nitro;
- R14a is hydroxy, C1-C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy or benzyloxy;
- R14c is C1-C6alkyl;
- R5 is hydrogen or a C1-C8alkyl, C3-C8alkenyl or C3-C6alkynyl or C3-C6cycloalkyl group which may be substituted once, twice or three times by chlorine, bromine, iodine, hydroxy, amino, formyl, nitro, cyano, mercapto, C1-C6alkoxy, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, halo-substituted C3-C6cycloalkyl, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6haloalkoxy, C3-C6haloalkenyloxy, cyano-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy, C1-C6alkoxy-C1-C6alkoxy-C1-C6alkoxy, C1-C6alkylthio-C1-C6alkoxy, C1-C6alkylsulfinyl-C1-C6alkoxy, C1-C6alkylsulfonyl-C1-C6alkoxy, C1-C6alkoxycarbonyl-C1-C6alkoxy, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, phenylcarbonyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, C1-C6alkylamino, di(C1-C6alkyl)amino, R15aC(X23)N(R18a)—, R16aN(R17a)C(X24)—, R16bN(R17b)C(X25)NR18b—, R15cSO2N(R18c)—, R16cN(R17c)C(X26)O—, R15bC(X27)O—, R19R20C═NO—, R15S(O)2O—, R16N(R17)SO2—, rhodano, phenyl, phenoxy, phenylthio, phenylsulfinyl or by phenylsulfonyl or which may be substituted from one to seventeen times by fluorine;
- wherein the phenyl- or benzyl-containing groups may in turn be substituted by one or more C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxy or nitro groups;
- R15a, R15b and R15c are hydrogen, C1-C8alkyl, C2-C6alkenyl, C3-C6cycloalkyl, phenyl, benzyl, C1-C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy or benzyloxy, wherein the phenyl groups may be substituted once, twice or three times by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxy or by nitro;
- R16a, R16b and R16c are hydrogen, C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, C3-C6cycloalkyl or phenyl, wherein phenyl may be substituted once, twice or three times by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxy or by nitro;
- R17a, R17b, R17c, R18a, R18b and R18c are hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- X23, X24, X25, X26 and X27 are oxygen or sulfur;
- R15, R16, R17, R19 and R20 are each independently of the others hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1-C6alkyl substituted by C1-C6alkoxy, or benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted once, twice or three times by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxy or by nitro;
- or R5 is a three- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, and wherein the ring system is bound to the substituent X1 directly or via a C1-C4alkylene, C2-C4alkenylene, C2-C4alkynylene, —N(R18)—C1-C4alkylene, —O—C1-C4alkylene, —S—C1-C4alkylene, —S(O)—C1-C4alkylene or —SO2—C1-C4alkylene chain, wherein the ring system may not be interrupted by —C(═O)—, —C(═S)—, —C(═NR5a)—, —N(═O)—, —S(═O)— or by —SO2—, and each ring system may contain not more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system itself may be substituted once, twice or three times by C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1-C6alkoxy, hydroxy, C1-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C1-C6alkylthio, C1-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, C3-C6-alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxycarbonylalkylthio, C2-C4-cyanoalkylthio, C1-C6alkylsulfinyl, C1-C6haloalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkylsulfonyl, aminosulfonyl, C1-C2alkylaminosulfonyl, di(C1-C2alkyl)aminosulfonyl, di(C1-C4alkyl)amino, halogen, cyano, nitro, phenyl or by benzylthio, wherein phenyl and benzylthio may in turn be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen;
- R5a is C1-C6alkyl, hydroxy, C1-C6alkoxy, cyano or nitro;
- R18 is hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1-C6alkyl substituted by C1-C6alkoxy, or benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted once, twice or three times by C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, halogen, cyano, hydroxy or by nitro;
- R6 is hydrogen, C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, C1-C6haloalkyl, hydroxy, C1-C6alkoxy, —C(O)R19a or —C(S)R20a;
- R19a and R20a are each independently of the other hydrogen, C1-C6alkyl, C3-C6cycloalkyl, phenyl, benzyl, heteroaryl, C1-C6alkoxy, C3-C6alkenyloxy, benzyloxy, C1-C4alkylthio or a group NR21R22;
- R21 and R22 are each independently of the other hydrogen, C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl or phenyl, and wherein phenyl, benzyl, benzyloxy and heteroaryl in R19a, R20a, R21 and R22 may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R21 together with R22 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R6 is -L2-X4—R24;
- wherein
- X4 is oxygen, —NR23—, —S—, —S(O)— or —S(O)2—;
- R23 is hydrogen, C1-C6alkoxy, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or is phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3-alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R24 is hydrogen or a C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, C1-C6alkoxy, C1-C3alkoxy-C1-C3alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6-alkylsulfonyl, cyano, C(X5)NR25R26, C3-C6cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R24 is C(O)—R74 or C(S)—R75;
- X5 is oxygen or sulfur;
- R25 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R26 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R25 together with R26 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R6 is -L3-R27;
- R27 is formyl, C1-C6alkylcarbonyl, C3-C6cycloalkylcarbonyl, benzoyl, C1-C6alkoxycarbonyl, cyano, C(X6)NR28R29, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- and wherein heteroaryl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro or by C1-C4alkoxycarbonyl;
- or R27 is C3-C6cycloalkyl or C5-C6cycloalkenyl each of which may in turn be substituted once, twice or three times by C1-C4alkyl, halogen or by C1-C4alkoxy;
- X6 is oxygen or sulfur;
- R28 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R29 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R28 together with R29 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R7 is hydrogen, C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, C1-C6haloalkyl, C3-C6cycloalkyl, phenyl, benzyl, heteroaryl, C(X7)R30 or NR33R34, wherein phenyl, benzyl and heteroaryl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3-alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- X7 is oxygen or sulfur;
- R30 is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, phenyl, heteroaryl, C1-C6alkoxy, C3-C6alkenyloxy, benzyloxy, C1-C4alkylthio or a group NR31R32;
- R31 and R33 are each independently of the other hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R32 and R34 are each independently of the other hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R31 together with R32 or R33 together with R34, in each case with the respective N atom to which they are bonded, form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R7 is -L4-X—R35;
- wherein
- X8 is oxygen, —NR36—, —S—, —S(O)— or —S(O)2—;
- R36 is hydrogen, C1-C6alkoxy, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or is phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3-alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R35 is hydrogen or a C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, C1-C6alkoxy, C1-C3alkoxy-C1-C3alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6-alkylsulfonyl, cyano, C(X9)NR37R38, C3-C6cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- X9 is oxygen or sulfur;
- R37 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R38 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R37 together with R38 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R7 is -L5-R39;
- R39 is formyl, C1-C6alkylcarbonyl, C3-C6cycloalkylcarbonyl, benzoyl, C1-C6alkoxycarbonyl, cyano, C(X10)NR40R41, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- and wherein heteroaryl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro or by C1-C4alkoxycarbonyl;
- or R39 is C3-C6cycloalkyl or C5-C6cycloalkenyl each of which may in turn be substituted once, twice or three times by C1-C4alkyl, halogen or by C1-C4alkoxy;
- X10 is oxygen or sulfur;
- R40 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R41 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R40 together with R41 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R6 and R7 together with the nitrogen atom to which they are bonded form a carbocyclic 3- to 7-membered, saturated or partially saturated or unsaturated monocyclic or bicyclic ring system which may be interrupted once by oxygen, once by sulfur, from one to three times by nitrogen and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3-haloalkylthio, cyano, nitro or by C1-C4alkoxycarbonyl;
- wherein each ring system may not be interrupted by —C(═O)—, —C(═S)—, —C(═NR5a)—, —N(═O)—, —S(═O)— or by —SO2—;
- R5a is C1-C6alkyl, hydroxy, C1-C6alkoxy, cyano or nitro;
- X2 is oxygen, —NR42—, sulfur, —S(O)— or —S(O)2—;
- R42 is hydrogen, C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, C1-C6haloalkyl, C3-C6cycloalkyl, phenyl, heteroaryl, C(X11)R43 or NR46R47;
- X11 is oxygen or sulfur;
- R43 is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, phenyl, heteroaryl, C1-C6alkoxy, C3-C6alkenyloxy, benzyloxy, C1-C4alkylthio or a group NR44R45;
- R44 and R46 are each independently of the other hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R45 and R47 are each independently of the other hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R44 together with R45 or R46 together with R47, in each case with the respective N atom to which they are bonded, form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R42 is -L6-X12—R48;
- wherein
- X12 is oxygen, —NR49—, —S—, —S(O)— or —S(O)2—;
- R49 is hydrogen, C1-C6alkoxy, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or is phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3-alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R48 is a C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, C1-C6alkoxy, C1-C3alkoxy-C1-C3alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, cyano, C(X13)NR50R51, C3-C6cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- X13 is oxygen or sulfur;
- R50 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R51 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R50 together with R51 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R42 is -L7-R52;
- R52 is formyl, C1-C6alkylcarbonyl, C3-C6cycloalkylcarbonyl, benzoyl, C1-C6alkoxycarbonyl, cyano, C(X14)NR53R54, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- and wherein heteroaryl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro or by C1-C4alkoxycarbonyl;
- or R52 is C3-C6cycloalkyl or C5-C6cycloalkenyl each of which may in turn be substituted once, twice or three times by C1-C4alkyl, halogen or by C1-C4alkoxy;
- X14 is oxygen or sulfur;
- R53 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R54 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R53 together with R54 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3-haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R8 is hydrogen or a C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, C1-C6alkoxy, C1-C3alkoxy-C1-C3alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6-alkylsulfonyl, cyano, C(X15)NR55R56, C3-C6cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, and wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- X15 is oxygen or sulfur;
- R55 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R56 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R55 together with R56 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R8 is cyano, C(O)—R76 or C(S)—R77;
- X3 is oxygen, —NR57—, sulfur, —S(O)— or —S(O)2—;
- R57 is hydrogen, C1-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, C1-C6haloalkyl, C3-C6cycloalkyl, phenyl, heteroaryl, C(X16)R58 or NR61R62;
- X16 is oxygen or sulfur;
- R58 is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, phenyl, heteroaryl, C1-C6alkoxy, C3-C6alkenyloxy, benzyloxy, C1-C4alkylthio or a group NR59R60;
- R59 and R61 are each independently of the other hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R60 and R62 are each independently of the other hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R59 together with R60 or R61 together with R62, in each case with the respective N atom to which they are bonded, form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R57 is -L8-X17—R63;
- wherein
- X17 is oxygen, —NR64—, —S—, —S(O)— or —S(O)2—;
- R64 is hydrogen, C1-C6alkoxy, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or is phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3-alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R63 is a C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, C1-C6alkoxy, C1-C3alkoxy-C1-C3alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, cyano, C(X18)NR65R66, C3-C6cycloalkyl, phenyl, phenoxy or by 5 or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- X18 is oxygen or sulfur;
- R65 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R66 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R65 together with R66 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R57 is -L9-R67;
- R67 is formyl, C1-C6alkylcarbonyl, C3-C6cycloalkylcarbonyl, benzoyl, C1-C6alkoxycarbonyl, cyano, C(X19)NR68R69, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- and wherein heteroaryl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro or by C1-C4alkoxycarbonyl;
- or R67 is C3-C6cycloalkyl or C5-C6cycloalkenyl each of which may in turn be substituted once, twice or three times by C1-C4alkyl, halogen or by C1-C4alkoxy;
- X19 is oxygen or sulfur;
- R68 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R69 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R68 together with R69 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- L1 is C1-C4alkylene which may be substituted once, twice or three times by C1-C4alkyl, halogen or by C1-C4alkoxy and to which C1-C4alkylene group there may be spirocyclically bound a further C2-C5alkylene group which may in turn be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and/or substituted by C1-C4alkyl or by C1-C4alkoxy;
- or L1 is C1-C4alkylene which may be substituted once, twice or three times by C1-C4alkyl, halogen or by C1-C4alkoxy, and wherein a carbon atom of that C1-C4alkylene group together with R9 or with R70 forms, by means of a further C2-C6alkylene chain, a ring system which may additionally be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and/or substituted by C1-C4alkyl or by C1-C4alkoxy;
- R9 is a group —X20—R70, wherein
- X20 is oxygen, —NR71—, —S—, —S(O)— or —S(O)2—;
- R71 is hydrogen or a C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, C1-C6alkoxy, C1-C3alkoxy-C1-C3alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6-alkylsulfonyl, cyano, C(X21)NR72R73, C3-C6cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- X21 is oxygen or sulfur;
- R72 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R73 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R72 together with R73 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R70 is hydrogen or a C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, C1-C6alkoxy, C1-C3alkoxy-C1-C3alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6-alkylsulfonyl, cyano, C(X15a)NR55aR56a, C3-C6cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, and wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- X15a is oxygen or sulfur;
- R55a is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R56a is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R55a together with R56a and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R70 is C1-C10alkylideneimino, (phenyl-C1-C4alkylidene)imino, or phenyl, wherein phenyl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3-alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- or R70 is cyano, C(O)—R78 or C(S)—R79;
- or R9 is formyl, C1-C6alkylcarbonyl, C3-C6cycloalkylcarbonyl, benzoyl, C1-C6alkoxycarbonyl, cyano, C(X35)NR125R126, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- and wherein heteroaryl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro or by C1-C4alkoxycarbonyl;
- or R9 is C3-C6cycloalkyl or C5-C6cycloalkenyl each of which may in turn be substituted once, twice or three times by C1-C4alkyl, halogen or by C1-C4alkoxy;
- X35 is oxygen or sulfur;
- R125 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R126 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R125 together with R126 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R74, R75, R76, R77, R78 and R79 are each independently of the others hydrogen, C1-C6alkyl, C3-C6cycloalkyl, phenyl, benzyl, heteroaryl, C1-C6alkoxy, C3-C6alkenyloxy, benzyloxy, C1-C4alkylthio or NR127R128, wherein phenyl, benzyl or heteroaryl may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R127 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl or phenyl which may be substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R128 is hydrogen, C1-C6alkyl, C3-C6alkenyl or C3-C6alkynyl;
- or R127 together with R128 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, C1-C3haloalkylthio, cyano, nitro, C1-C4alkoxycarbonyl or by C1-C4alkylcarbonylamino;
- R3 is hydroxy, O−M+ wherein M+ is a metal cation or an ammonium cation, or is halogen or S(O)pR80, wherein
- p is 0, 1 or 2;
- R80 is C1-C12alkyl, C2-C12alkenyl, C2-C12alkynyl, C3-C12allenyl, C3-C12cycloalkyl or C5-C12-cycloalkenyl;
- or R80 is R121—C1-C12alkylene or R122—C2-C12alkenylene, wherein the alkylene or alkenylene chain may be interrupted by —O—, —S—, —S(O)—, —SO2— or by —C(O)— and/or substituted from one to five times by R123;
- or R80 is phenyl which may be substituted once, twice, three times, four times or five times by R124;
- R121 and R122 are each independently of the other halogen, cyano, rhodano, hydroxy, C1-C6alkoxy, C2-C6alkenyloxy, C2-C6alkynyloxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C2-C6alkenylthio, C2-C6alkynylthio, C1-C6alkylsulfonyloxy, phenylsulfonyloxy, C1-C6-alkylcarbonyloxy, benzoyloxy, C1-C4alkoxycarbonyloxy, C1-C6alkylcarbonyl, C1-C4alkoxycarbonyl, benzoyl, aminocarbonyl, C1-C4alkylaminocarbonyl, C3-C6cycloalkyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, wherein the phenyl-containing groups may in turn be substituted once, twice or three times by halogen, C1-C3alkyl, C1-C3haloalkyl, hydroxy, C1-C3alkoxy, C1-C3haloalkoxy, cyano or by nitro;
- R123 is hydroxy, halogen, C1-C6alkyl, C1-C6alkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, cyano, carbamoyl, carboxy, C1-C4alkoxycarbonyl or phenyl, wherein phenyl may be substituted once, twice or three times by hydrogen, C1-C4alkyl, C1-C4haloalkyl, C3-C4alkenyl, C3-C4alkynyl or by C1-C4alkoxy;
- R124 is halogen, C1-C3alkyl, C1-C3haloalkyl, hydroxy, C1-C3alkoxy, C1-C3haloalkoxy, cyano or nitro;
- A1 is —C(R112R113)— or —NR114—;
- A2 is —C(R115R116)m—, —C(═O)—, —O—, —NR117— or —S(O)q—;
- A3 is —C(R118R119)— or —NR120—;
- with the proviso that A2 is other than —O— or —S(O)q— when A1 is —NR114— and/or A3 is —NR120;
- R112 and R118 are each independently of the other hydrogen, C1-C4alkyl, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkoxycarbonyl, hydroxy, C1-C4alkoxy, C3-C4alkenyloxy, C3-C4alkynyloxy, hydroxy-C1-C4alkyl, C1-C4alkylsulfonyloxy-C1-C4alkyl, halogen, cyano or nitro;
- R113 and R119 are each independently of the other hydrogen, C1-C4alkyl or C1-C4alkylthio, C1-C4alkylsulfinyl or C1-C4alkylsulfonyl;
- or R113 together with R112 and/or R119 together with R118 form a C2-C5alkylene chain which may be interrupted by —O—, —C(O)O— or by —S(O)r—;
- R114 and R120 are each independently of the other hydrogen, C1-C4alkyl, C1-C4haloalkyl, C3-C4alkenyl, C3-C4alkynyl or C1-C4alkoxy;
- R115 is hydrogen, hydroxy, C1-C4alkyl, C1-C4haloalkyl, C1-C3hydroxyalkyl, C1-C4alkoxy-C1-C3alkyl, C1-C4alkylthio-C1-C3alkyl, C1-C4alkylcarbonyloxy-C1-C3alkyl, C1-C4alkylsulfonyloxy-C1-C3alkyl, tosyloxy-C1-C3alkyl, di(C1-C4alkoxy)C1-C3alkyl, C1-C4alkoxycarbonyl, formyl, C3-C5oxacycloalkyl, C3-C5thiacycloalkyl, C3-C4dioxacycloalkyl, C3-C4dithiacycloalkyl, C3-C4-oxathiacycloalkyl, C1-C4alkoxyiminomethyl, cyano, carbamoyl, C1-C4alkylaminocarbonyl or di(C1-C4alkyl)aminocarbonyl;
- or R115 together with R112 or R113 or R114 or R116 or R118 or R119 or R120 or, when m is 2, also with a second R115 form a C1-C4alkylene bridge;
- R116 is hydrogen, C1-C3alkyl or C1-C3haloalkyl;
- R117 is hydrogen, C1-C3alkyl, C1-C3haloalkyl, C1-C4alkoxycarbonyl, C1-C4alkylcarbonyl or di(C1-C4alkyl)aminocarbonyl;
- m is 1 or 2;
- and
- q and r are each independently of the other 0, 1 or 2;
- and also to agronomically acceptable salts, tautomers, isomers and enantiomers of those compounds.
A herbicidal composition which, besides comprising formulation adjuvants, comprises a herbicidally effective amount of compound of formula I.
A method of controlling grasses and weeds in crops of useful plants, which comprises applying a herbicidally effective amount of a compound of formula I or of a composition comprising such a compound to the plants or the locus thereof.
Dependencies are inferred from the claim text.