Herbicidal composition

A herbicidally selective composition that, in addition to comprising customary inert formulation adjuvants, comprises as active ingredient a mixture

• a) a herbicidally effective amount of a compound of formula I
• 120
• wherein each R is independently hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C6haloalkyl, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, C1-C6alkoxycarbonyl, C1-C6alkylcarbonyl, C1-C6alkylamino, di(C1-C6alkyl)amino, C1-C6alkylaminosulfonyl, di(C1-C6alkyl)aminosulfonyl, —N(R1)—S—R2, —N(R3)—SO—R4, —N(R5)—SO2—R6, nitro, cyano, halogen, hydroxy, amino, benzylthio, benzylsulfinyl, benzylsulfonyl, phenyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl;
• wherein the phenyl group may itself be mono-, di- or tri-substituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy, 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, C2-C4dialkylaminosulfonyl, C1-C3alkylene-R45, NR46R47, halogen, cyano, nitro, phenyl or by benzylthio, wherein the latter phenyl and benzylthio groups may themselves be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
• or each R is independently a monocyclic or fused bicyclic ring system having from 5 to 10 members, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur;
• wherein the ring system either is bound directly to the pyridine ring or is bound to the pyridine ring via a C1-C4alkylene group, and each ring system may not contain more than two oxygen atoms and may not contain more than two sulfur atoms, and the ring system may itself be mono-, di- or tri-substituted by C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C6alkoxy, 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, C2-C4dialkylaminosulfonyl, C1-C3alkylene-R7, NR8R9, halogen, cyano, nitro, phenyl or by benzylthio, wherein phenyl and benzylthio may themselves be substituted on the phenyl ring by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen;
• or
• each R is independently C1-C4alkoxy-C1-C4alkyl or C1-C4alkoxy-C1-C4alkoxy-C1-C4alkyl;
• m is 1, 2, 3 or 4;
• R1, R3 and R5 are each independently of the others hydrogen or C1-C6alkyl;
• R2 is NR10R11, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6-haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C3-C6cycloalkyl or phenyl, wherein phenyl may itself be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
• R4 is NR12R13, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6-haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C3-C6cycloalkyl or phenyl, wherein phenyl may itself be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
• R6 is NR14R15, C1-C6alkoxy, C1-C6haloalkoxy, C1-C6alkyl, C1-C6haloalkyl, C3-C6alkenyl, C3-C6-haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C3-C6cycloalkyl or phenyl, wherein phenyl may itself be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or by nitro;
• R7 and R45 are each independently of the other C1-C3alkoxy, C2-C4alkoxycarbonyl, C1-C3-alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl or phenyl, wherein phenyl may itself be substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano nitro;
• R8, R10, R12, R14 and R46 are each independently of the others hydrogen or C1-C6alkyl;
• R9, R11, R13, R15 and R47 are each independently of the others C1-C6alkyl or C1-C6alkoxy;
• Q is the group Q1
• 121
• wherein R16, R17, R18 and R19 are each independently of the others hydrogen, hydroxy, C1-C4alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C4alkyl-NHS(O)2, C1-C4haloalkyl, —NH—C1-C4alkyl, —N(C1-C4alkyl)2, C1-C6alkoxy, cyano, nitro, halogen, or phenyl which may itself be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C4alkyl-S(O)2O, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro, COOH or by cyano;
• or two adjacent substituents out of R16, R17, R18 and R19 form a C2-C6alkylene bridge;
• R20 is hydroxy, O−M+, halogen, C1-C12alkoxy, C1-C12alkylcarbonyloxy, C2-C4alkenylcarbonyloxy, C3-C6cycloalkylcarbonyloxy, C1-C12alkoxycarbonyloxy, C1-C12alkylcarbonyloxy, R21R22N—C(O)O, C1-C12alkylthio, C1-C12alkylsulfinyl, C1-C12alkylsulfonyl, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C2-C12alkenylthio, C2-C12alkenylsulfinyl, C2-C12alkenylsulfonyl, C2-C12haloalkenylthio, C2-C12haloalkenylsulfinyl, C2-C12haloalkenylsulfonyl, C2-C12alkynylthio, C2-C12alkynylsulfinyl, C2-C12alkynylsulfonyl, C1-C4alkyl-S(O)2O, phenyl-S(O)2O, (C1-C4alkoxy)2P(O)O, C1-C4alkyl(C1-C4alkoxy)P(O)O, H(C1-C4alkoxy)P(O)O, C1-C12-alkyl-S(CO)O, benzyloxy, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, wherein the phenyl group may itself be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkyl-S(O)2O, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro or by cyano;
• and
• R21 and R22 are each independently of the other hydrogen or C1-C4alkyl;
• or is the group Q2
• 122
• wherein R23 is hydroxy, O−M+, halogen, C1-C12alkoxy, C1-C12alkylcarbonyloxy, C2-C4-alkenylcarbonyloxy, C3-C6cycloalkylcarbonyloxy, C1-C12alkoxycarbonyloxy, C1-C12alkyl-carbonyloxy, R24R25N—C(O)O, C1-C12alkylthio, C1-C12alkylsulfinyl, C1-C12alkylsulfonyl, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C2-C12alkenylthio, C2-C12-alkenylsulfinyl, C2-C12alkenylsulfonyl, C2-C12haloalkenylthio, C2-C12haloalkenylsulfinyl, C2-C12-haloalkenylsulfonyl, C2-C12alkynylthio, C2-C12alkynylsulfinyl, C2-C12alkynylsulfonyl, C1-C4-alkyl-S(O)2O, phenyl-S(O)2O, (C1-C4alkoxy)2P(O)O, C1-C4alkyl(C1-C4alkoxy)P(O)O, H(C1-C4alkoxy)P(O)O, C1-C12-alkyl-S(CO)O, benzyloxy, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, wherein the phenyl group may itself be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkyl-S(O)2O, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro or by cyano;
• R24 and R25 are each independently of the other hydrogen or C1-C4alkyl;
• and
• Y is oxygen, sulfur, a chemical bond or a C1-C4alkylene bridge;
• or is the group Q3
• 123
• wherein R44, R37, R38 and R39 are each independently of the others hydrogen, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxycarbonyl, C1-C6alkylthio, C1-C6alkyl-sulfinyl, C1-C6alkylsulfonyl, C1-C6alkyl-NHS(O)2, C1-C6alkylamino, di(C1-C6alkyl)amino, hydroxy, C1-C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, hydroxy-C1-C6alkyl, C1-C4alkylsulfonyloxy-C1-C6alkyl, tosyloxy-C1-C6alkyl, halogen, cyano, nitro, phenyl, or phenyl substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C4alkyl-S(O)2O, C1-C6haloalkylthio, C1-C6haloalkylsulfinyl, C1-C6haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C6alkylthio-N(C1-C4alkyl), C1-C6alkylsulfinyl-N(C1-C4alkyl), C1-C6alkylsulfonyl-N(C1-C4alkyl), halogen, nitro, COOH or by cyano;
• or adjacent R44 and R37 or R38 and R39 together are C3-C6alkylene;
• W is oxygen, sulfur, sulfinyl, sulfonyl, —CR41R42—, —C(O)— or —NR43—;
• R41 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylthio-C1-C4alkyl, C1-C4alkylcarbonyloxy-C1-C4alkyl, C1-C4alkylsulfonyloxy-C1-C4alkyl, tosyloxy-C1-C4alkyl, di(C1-C3alkoxyalkyl)methyl, di(C1-C3alkylthioalkyl)methyl, (C1-C3alkoxyalkyl)-(C1-C3alkylthioalkyl)-methyl, C3-C5oxacycloalkyl, C3-C5thiacycloalkyl, C3-C4dioxacycloalkyl, C3-C4dithiacycloalkyl, C3-C4oxathiacycloalkyl, formyl, C1-C4alkoxycarbonyl, or phenyl which may itself be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkylthio, C1-C4alkyl-sulfinyl, C1-C4alkylsulfonyl, C1-C4alkyl-S(O)2O, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C6alkylthio-N(C1-C4alkyl), C1-C6alkylsulfinyl-N(C1-C4alkyl), C1-C6alkylsulfonyl-N(C1-C4alkyl), halogen, nitro, COOH or by cyano;
• or R42 together with R39 is C1-C6alkylene;
• R42 is hydrogen, C1-C4alkyl or C1-C4haloalkyl;
• R40 is hydroxy, O−M+, halogen, C1-C12alkoxy, C1-C12alkylcarbonyloxy, C2-C4alkenylcarbonyloxy, C3-C6cycloalkylcarbonyloxy, C1-C12alkoxycarbonyloxy, C1-C12alkylcarbonyloxy, R96R97N—C(O)O, C1-C12alkylthio, C1-C12alkylsulfinyl, C1-C12alkylsulfonyl, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C2-C12alkenylthio, C2-C12alkenylsulfinyl, C2-C12alkenylsulfonyl, C2-C12haloalkenylthio, C2-C12haloalkenylsulfinyl, C2-C12haloalkenylsulfonyl, C2-C12alkynylthio, C2-C12alkynylsulfinyl, C2-C12alkynylsulfonyl, C1-C4alkyl-S(O)2O, phenyl-S(O)2O, (C1-C4alkoxy)2P(O)O, C1-C4alkyl(C1-C4alkoxy)P(O)O, H(C1-C4alkoxy)P(O)O, C1-C12-alkyl-S(CO)O, benzyloxy, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, wherein the phenyl group may itself be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkyl-S(O)2O, C1-C4haloalkylthio, C1-C4haloalkysulfinyl, C1-C4haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro or by cyano;
• R96 and R97 are each independently of the other hydrogen or C1-C4alkyl;
• R43 is hydrogen, C1-C4alkyl, C1-C4alkoxycarbonyl, or phenyl which may itself be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkyl-S(O)2O, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro or by cyano;
• or is the group Q4
• 124
• wherein R30 hydroxy, O−M+, halogen, C1-C12alkoxy, C1-C12alkylcarbonyloxy, C2-C4alkenylcarbonyloxy, C3-C6cycloalkylcarbonyloxy, C1-C12alkoxycarbonyloxy, C1-C12alkylcarbonyloxy, R31R32N—C(O)O, C1-C12alkylthio, C1-C12alkylsulfinyl, C1-C12alkylsulfonyl, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C2-C12alkenylthio, C2-C12alkenylsulfinyl, C2-C12-alkenylsulfonyl, C2-C12haloalkenylthio, C2-C12haloalkenylsulfinyl, C2-C12haloalkenylsulfonyl, C2-C12alkynylthio, C2-C12alkynylsulfinyl, C2-C12alkynylsulfonyl, C1-C4alkyl-S(O)2O, phenyl-S(O)2O, (C1-C4alkoxy)2P(O)O, C1-C4alkyl(C1-C4alkoxy)P(O)O, H(C1-C4alkoxy)P(O)O, C1-C12-alkyl-S(CO)O, benzyloxy, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl, wherein the phenyl group may itself be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkyl-S(O)2O, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro or by cyano;
• and
• R31 and R32 are each independently of the other hydrogen or C1-C4alkyl;
• R33 and R34 are each independently of the other hydrogen, hydroxy, C1-C4alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C4alkoxycarbonyl, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C4alkyl-NHS(O)2, C1-C4haloalkyl, —NH—C1-C4alkyl, —N(C1-C4alkyl)2, C1-C6alkoxy, cyano, nitro, halogen, or phenyl which may itself be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C6alkylthio, C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, C1-C4alkyl-S(O)2O, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro, COOH or by cyano;
• or R33 and R34 together form a C2-C6alkylene bridge;
• and
• R35 is hydrogen, C1-C4alkyl, C1-C4alkoxycarbonyl, or phenyl which may itself be substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylcarbonyl, C1-C4alkoxycarbonyl, amino, C1-C4alkylamino, di(C1-C4alkyl)amino, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4alkyl-S(O)2O, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4haloalkyl-S(O)2O, C1-C4alkyl-S(O)2NH, C1-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro, COOH or by cyano;
• or is the group Q5
• 125
• wherein Z is sulfur, SO or SO2;
• R01 is hydrogen, C1-C8alkyl, C1-C8alkyl substituted by halogen, C1-C4alkoxy, C1-C4alkylthio, C1C4alkylsulfonyl, C1-C4alkylsulfinyl, hydroxy, cyano, nitro, —CHO, —CO2R02, —COR03, —COSR04, —NR05R06, CONR036R037, or by phenyl which may itself be substituted by C1-C4alkyl, C1-C6haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C6alkenyl, C3-C6alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano, —COOH, COOC1-C4alkyl, COOphenyl, C1-C4alkoxy, phenoxy, (C1-C4alkoxy)-C1-C4alkyl, (C1-C4alkylthio)-C1-C4alkyl, (C1-C4alkylsulfinyl)-C1-C4alkyl, (C1-C4alkylsulfonyl)-C1-C4alkyl, NHSO2—C1-C4alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2—C1-C4alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2—C1-C4alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6alkynyl)SO2—C1-C4alkyl, N(C3-C6alkynyl)SO2-phenyl, N(C3-C7cycloalkyl)SO2—C1-C4alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2—C1-C4alkyl, N(phenyl)SO2-phenyl, OSO2—C1-C4alkyl, CONR025R026, OSO2—C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthio, C1-C4haloalkylthio, phenylthio, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, phenylsulfonyl, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, phenylsulfinyl, C1-C4alkylenephenyl or by —NR015CO2R027;
• or R01 is C2-C8alkenyl or C2-C8alkenyl substituted by halogen, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfonyl, C1-C4alkylsulfinyl, —CONR032R033, cyano, nitro, —CHO, —CO2R038, —COR039, —COS—C1-C4alkyl, —NR034R035, or by phenyl which may itself be substituted by C1-C4alkyl, C1-C6haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C6alkenyl, C3-C6alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano, —COOH, COOC1-C4alkyl, COOphenyl, C1-C4alkoxy, phenoxy, (C1-C4alkoxy)-C1-C4alkyl, (C1-C4alkylthio)-C1-C4alkyl, (C1-C4alkylsulfinyl)-C1-C4alkyl, (C1-C4alkylsulfonyl)-C1-C4alkyl, NHSO2—C1-C4alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2—C1-C4alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2—C1-C4alkyl, N(C2-C6alkenyl)SO2phenyl, N(C3-C6alkynyl)SO2—C1-C4alkyl, N(C3-C6alkynyl)SO2-phenyl, N(C3-C7cycloalkyl)SO2—C1-C4alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2—C1-C4alkyl, N(phenyl)SO2-phenyl, OSO2—C1-C4alkyl, CONR040R041, OSO2—C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthio, C1-C4haloalkylthio, phenylthio, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, phenylsulfonyl, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, phenylsulfinyl, C1-C4alkylenephenyl or by —NR043CO2R042;
• or R01 is C3-C6alkynyl or C3-C6alkynyl substituted by halogen, C1-C4haloalkyl, cyano, —CO2R044, or by phenyl which may itself be substituted by C1-C4alkyl, C1-C6haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C6alkenyl, C3-C6alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano, —COOH, COOC1-C4alkyl, COOphenyl, C1-C4alkoxy, phenoxy, (C1-C4alkoxy)-C1-C4alkyl, (C1-C4alkylthio)-C1-C4alkyl, (C1-C4alkylsulfinyl)-C1-C4alkyl, (C1-C4alkysulfonyl)-C1-C4alkyl, NHSO2—C1-C4alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2—C1-C4alkyl, N(C1-C6alkyl)SO2-phenyl, N(C3-C6alkenyl)SO2—C1-C4alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6alkynyl)SO2—C1-C4alkyl, N(C3-C6alkynyl)SO2-phenyl, N(C3-C7cycloalkyl)SO2—C1-C4alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2—C1-C4alkyl, N(phenyl)SO2-phenyl, OSO2—C1-C4alkyl, CONR028R029, OSO2—C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthio, C1-C4haloalkylthio, phenylthio, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, phenylsulfonyl, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, phenylsulfinyl, C1-C4alkylenephenyl or by —NR031CO2R030;
• or R01 is C3-C7cycloalkyl or C3-C7cycloalkyl substituted by C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, or by phenyl which may itself be substituted by halogen, nitro, cyano, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkyl or by C1-C4haloalkyl;
• or
• R01 is C1-C4alkylene-C3-C7cycloalkyl, phenyl, or phenyl substituted by C1-C4alkyl, C1-C6haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C6alkenyl, C3-C6alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano, —COOH, COOC1-C4alkyl, COOphenyl, C1-C4alkoxy, phenoxy, (C1-C4alkoxy)-C1-C4alkyl, (C1-C4alkylthio)-C1-C4alkyl, (C1-C4alkylsulfinyl)-C1-C4alkyl, (C1-C4alkylsulfonyl)-C1-C4alkyl, NHSO2—C1-C4alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2—C1-C4alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2—C1-C4alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6alkynyl)SO2—C1-C4alkyl, N(C3-C6alkynyl)SO2-phenyl, N(C3-C7cycloalkyl)SO2—C1-C4alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2—C1-C4alkyl, N(phenyl)SO2-phenyl, OSO2—C1-C4alkyl, CONR045R046, OSO2—C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthio, C1-C4haloalkylthio, phenylthio, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, phenylsulfonyl, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, phenylsulfinyl or by —NR048CO2R047;
• or
• R01 is C1-C4alkylenephenyl, COR07 or from 4- to 6-membered heterocyclyl;
• R02, R038, R044 and R066 are each independently of the others hydrogen, C1-C4alkyl, phenyl, or phenyl substituted by C1-C4alkyl, C1-C6haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C6alkenyl, C3-C6alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano, —COOH, COOC1-C4alkyl, COOphenyl, C1-C4alkoxy, phenoxy, (C1-C4alkoxy)-C1-C4alkyl, (C1-C4alkylthio)-C1-C4alkyl, (C1-C4alkylsulfinyl)-C1-C4alkyl, (C1-C4alkylsulfonyl)-C1-C4alkyl, NHSO2—C1-C4alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2—C1-C4alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2—C1-C4alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6alkynyl)SO2—C1-C4alkyl, N(C3-C6alkynyl)SO2-phenyl, N(C3-C7Cycloalkyl)SO2—C1-C4alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2—C1-C4alkyl, N(phenyl)SO2-phenyl, OSO2—C1-C4alkyl, CONR049R050, OSO2—C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthio, C1-C4haloalkylthio, phenylthio, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, phenylsulfonyl, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, phenylsulfinyl, —C1-C4-alkylphenyl or by —NR052CO2R053;
• R03, R039 and R067 are each independently of the others C1-C4alkyl, phenyl, or phenyl substituted by C1-C4alkyl, C1-C6haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C6alkenyl, C3-C6alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano, —COOH, COOC1-C4alkyl;
• COOphenyl, C1-C4alkoxy, phenoxy, (C1-C4alkoxy)-C1-C4alkyl, (C1-C4alkylthio)-C1-C4alkyl, (C1-C4alkylsulfinyl)-C1-C4alkyl, (C1-C4alkylsulfonyl)-C1-C4alkyl, NHSO2—C1-C4alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2—C1-C4alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2—C1-C4alkyl, N(C2-C6alkenyl)SO2phenyl, N(C3-C6alkynyl)SO2—C1-C4alkyl, N(C3-C6alkynyl)SO2-phenyl, N(C3-C7cycloalkyl)SO2—C1-C4alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2—C1-C4alkyl, N(phenyl)SO2-phenyl, OSO2—C1-C4alkyl, CONR068R054, OSO2—C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthio, C1-C4haloalkylthio, phenylthio, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, phenylsulfonyl, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, phenylsulfinyl, —(CH2)t-phenyl or by —NR056CO2R055;
• R04 is C1-C4alkyl;
• R05 is hydrogen, C1-C4alkyl, C2-C6alkenyl, C3-C6alkynyl, C3-C7cycloalkyl, phenyl, or phenyl substituted by C1-C4alkyl, C1-C6haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C6alkenyl, C3-C6-alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano, —COOH, COOC1-C4alkyl, COOphenyl, C1-C4alkoxy, phenoxy, (C1-C4alkoxy)-C1-C4alkyl, (C1-C4alkylthio)-C1-C4alkyl, (C1-C4alkylsulfinyl)-C1-C4alkyl, (C1-C4alkylsulfonyl)-C1-C4alkyl, NHSO2—C1-C4alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2—C1-C4alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2—C1-C4alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6alkynyl)SO2H, N(C3-C6alkynyl)SO2—C4alkyl, N(C3-C6alkynyl)SO2-phenyl, N(C3-C7cycloalkyl)SO2H, N(C3-C7cycloalkyl)SO2—C1-C4alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2—C1-C4alkyl, N(phenyl)SO2-phenyl, OSO2—C1-C4alkyl, CONR057R058, OSO2—C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthio, C1-C4haloalkylthio, phenylthio, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, phenylsulfonyl, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, phenylsulfinyl, C1-C4alkylenephenyl or by —NR060CO2R059;
• R06 is hydrogen, C1-C4alkyl, C2-C6alkenyl, C3-C6alkynyl, C3-C7cycloalkyl, phenyl, or phenyl substituted by C1-C4alkyl, C1-C6haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C6alkenyl, C3-C6alkynyl, C3-C6alkenyloxy, C3-C6alkynyloxy, halogen, nitro, cyano, —COOH, COOC1-C4alkyl, COOphenyl, C1-C4alkoxy, phenoxy, (C1-C4alkoxy)-C1-C4alkyl, (C1-C4alkylthio)-C1-C4alkyl, (C1-C4alkylsulfinyl)-C1-C4alkyl, (C1-C4alkylsulfonyl)-C1-C4alkyl, NHSO2—C1-C4alkyl, NHSO2-phenyl, N(C1-C6alkyl)SO2—C1-C4alkyl, N(C1-C6alkyl)SO2-phenyl, N(C2-C6alkenyl)SO2—C1-C4alkyl, N(C2-C6alkenyl)SO2-phenyl, N(C3-C6alkynyl)SO2—C1-C4alkyl, N(C3-C6alkynyl)SO2-phenyl, N(C3-C7cycloalkyl)SO2—C1-C4alkyl, N(C3-C7cycloalkyl)SO2-phenyl, N(phenyl)SO2—C1-C4alkyl, N(phenyl)SO2-phenyl, OSO2—C1-C4alkyl, CONR061R062, OSO2—C1-C4haloalkyl, OSO2-phenyl, C1-C4alkylthio, C1-C4haloalkylthio, phenylthio, C1-C4alkylsulfonyl, C1-C4haloalkylsulfonyl, phenylsulfonyl, C1-C4alkylsulfinyl, C1-C4haloalkylsulfinyl, phenylsulfinyl, C1-C4-alkylenephenyl or by —NR064CO2R063;
• R07 is phenyl, C1-C4alkyl, C1-C4alkoxy or —NR08R09;
• R08 and R09 are each independently of the other C1-C4alkyl, phenyl, or phenyl substituted by halogen, nitro, cyano, C1-C4alkyl, C1-C4alkoxy, C1-C4thioalkyl, —CO2R066, —COR067, C1-C4-alkylsulfonyl, C1-C4alkylsulfinyl or by C1-C4haloalkyl;
• or R08 and R09 together form a 5- or 6-membered ring, which may be interrupted by oxygen, NR065 or by S;
• R015, R031, R043, R048, R052, R056, R060 and R064 are each independently of the others hydrogen, C1-C4alkyl, C2-C6alkenyl, C3-C6alkynyl or C3-C7cycloalkyl;
• R025, R026, R027, R028, R029, R030, R032, R033, R034, R035, R036, R037, R040, R041, R042, R045, R046, R047, R049, R050, R053, R054, R055, R057, R058, R059, R061, R062, R063, R065, and R068, are each independently of the others hydrogen, C1-C4alkyl, C2-C6alkenyl, C3-C6alkynyl, C3-C7cycloalkyl, phenyl, or phenyl substituted by halogen, nitro, cyano, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkylthio, C1-C4haloalkylthio, C1-C4alkyl or by C1-C4haloalkyl;
• and
• R36 is C1-C4alkyl, C1-C4haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C3-C6cycloalkyl, or C3-C6cycloalkyl substituted by halogen, C1-C4alkyl, C1-C4haloalkyl, C3-C6alkenyl, C3-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C1-C4alkoxycarbonyl, C1-C4alkylthio, C1-C4alkylsulfinyl, C1-C4alkylsulfonyl, C1-C4haloalkylthio, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl, C1-C4alkylcarbonyl, di(C1-C4alkyl)amino, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkyl-S(O)2O, C1-C4haloalkyl-S(O)2O, or by phenyl which may itself be substituted by halogen, C1-C4alkyl, C1-C4haloalkyl, C3-C6alkenyl, C3-C6alkynyl, cyano, nitro or by COOH;
• or an agronomically acceptable salt of such a compound, and
• b) a synergistically effective amount of one or more compounds selected from a compound of formula 2.1
• 126
• wherein R51 is CH2—OMe, ethyl or hydrogen;
• R52 is hydrogen or R51 and R52 together are the group —CH═CH—CH═CH—;
• and a compound of formula 2.2
• 127
• wherein R53 is ethyl, R54 is methyl or ethyl and R55 is —CH(Me)—CH2OMe, <S>—CH(Me)-CH2OMe, CH2OMe or CH2O—CH2CH3;
• and a compound of formula 2.3
• 128
• wherein R56 is CH(Me)-CH2OMe or <S>CH(Me)-CH2OMe;
• and a compound of formula 2.4
• 129
• wherein R57 is chlorine, methoxy or methylthio, R58 is ethyl and R59 is ethyl, isopropyl, —C(CN)(CH3)-CH3 or tert-butyl;
• and a compound of formula 2.5
• 130
• wherein R60 is ethyl or n-propyl, R61 is COO−1/2Ca++, —CH2—CH(Me)S—CH2CH3 or the group
• 131
• and X is oxygen, N—O—CH2CH3 or N—O—CH2CH═CH—Cl;
• and a compound of formula 2.6
• 132
• wherein R62 is hydrogen, methoxy or ethoxy, R63 is hydrogen, methyl, methoxy or fluorine, R64 is COOMe, fluorine or chlorine, R65 is hydrogen or methyl, Y is methine, C—F or nitrogen, Z is methine or nitrogen and R66 is fluorine or chlorine;
• and a compound of formula 2.7
• 133
• wherein R67 is hydrogen or —C(O)—S-n-octyl;
• and a compound of formula 2.8
• 134
• wherein R68 is either bromine or iodine;
• and a compound of formula 2.9
• 135
• wherein R69 is chlorine or nitro;
• and a compound of formula 2.10
• 136
• wherein R70 is fluorine or chlorine and R71 is —CH2—CH(Cl)-COOCH2CH3 or —NH—SO2Me;
• and a compound of formula 2.11
• 137
• wherein R72 is trifluoromethyl or chlorine;
• and a compound of formula 2.12
• 138
• wherein R73 is NH2 or <S>NH2;
• and a compound of formula 2.13
• 139
• wherein Y, is nitrogen, methine, NH—CHO or N—Me, Y2 is nitrogen, methine or C—I, Y3 is methine, Y4 is methine or Y3 and Y4 together are sulfur or C—Cl, Y5 is nitrogen or methine, Y6 is methyl, difluoromethoxy, trifluoromethyl or methoxy, Y7 is methoxy or difluoromethoxy and R74 is CONMe2, COOMe, COOC2H5, trifluoromethyl, CH2—CH2CF3 or SO2CH2CH3, or a sodium salt thereof;
• and the compound of formula 2.13.c
• 140
• and the compound of formula 2.14
• 141
• and the compound of formula 2.15
• 142
• and the compound of formula 2.16
• 143
• and the compound of formula 2.17
• 144
• and the compound of formula 2.18
• 145
• and the compound of formula 2.19
• 146
• and the compound of formula 2.20
• 147
• and the compound of formula 2.21
• 148
• and the compound of formula 2.22
• 149
• and the compound of formula 2.23
• 150
• and the compound of formula 2.24
• 151
• and the compound of formula 2.25
• 152
• and the compound of formula 2.26
• 153
• and the compound of formula 2.27
• 154
• and the compound of formula 2.28
• 155
• and the compound of formula 2.29
• 156
• and the compound of formula 2.30
• 157
• and the compound of formula 2.31
• 158
• and the compound of formula 2.32
• 159
• and the compound of formula 2.33
• 160
• and the compound of formula 2.34
• 161
• and the compound of formula 2.35
• 162
• and the compound of formula 2.36
• 163
• and the compound of formula 2.37
• 164
• and the compound of formula 2.38
• 165
• and the compound of formula 2.39
• 166
• and the compound of formula 2.40
• 167
• and the compound of formula 2.41
• 168
• and the compound of formula 2.42
• 169
• and the compound of formula 2.43
• 170
• and the compound of formula 2.44
• 171
• and the compound of formula 2.45
• 172
• and the compound of formula 2.46
• 173
• and the compound of formula 2.47
• 174
• and the compound of formula 2.48
• 175
• and the compound of formula 2.49
• 176
• and the compound of formula 2.50
• 177
• and the compound of formula 2.51
• 178