Patent EP-0616770-B1 (EP)
Inventor: GLOCK JUTTA DR
IPC: A01N43/10
Filed: 1994-03-14
Granted: 1999-05-06
Abstract: Mixtures of a herbicidally active amount of a haloacetamide of the formula I <IMAGE> and of a herbicide-antagonistically effective amount of a compound of the formula II  R-CHYCI     (II),  in which R is a radical of the formula <IMAGE>  where   R33 and R44 independently of one another are C1-C6-alkyl, C2-C6-alkenyl or a radical of the formula <IMAGE>  or   R33 and R34 together are <IMAGE>   R35 and R36 independently of one another are hydrogen or C1-C6-alkyl; or   R33 and R34 together are <IMAGE>     R37 and R38 independently of one another are C1-C4-alkyl, or   R37 and R38 together are -(CH2)5-;   R39 is hydrogen, C1-C4-alkyl or <IMAGE>  or   R33 and R34 together are <IMAGE>  and R40, R41, R42, R43, R44, R45, R46, R47, R48 , R49, R50, R51, R52, R53, R54 and R55 independently of one another are hydrogen or C1-C4-alkyl, or   R is a radical of the formula <IMAGE>  or   R is a radical of the formula <IMAGE>  in which   R1, R2, R3 and R4 independently of one another are hydrogen, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-haloalkyl, R5, R6, R7 and R8 independently of one another are hydrogen, C1-C4-alkyl or C1-C4-haloalkyl, where at least one of the substituents R5 and R6 is other than hydrogen, or   R is a radical of the formula <IMAGE>  in which   R9 is C1-C4-alkyl or halogen,   R10 is halogen, R11 and R12 independently of one another are hydrogen or C1-C4-alkyl, and   Q is C1-C4-alkylene or alkyl-substituted C1-C4-alkylene, or   R is a radical of the formula <IMAGE>  in which R14 is hydrogen, halogen, C1-C4-alkyl, dioxymethylene, C1-C4-alkoxy C2-C4-alkenyloxy, C2-C4-alkynyloxy or cyano-C1-C4-alkyl, P C1-C 4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C8-cycloalkyl, C1-C4- alkoxy-C1-C4-alkyl, C2-C4-alkenoxy-C1-C4-alkyl, C2-C4-alkynoxy-C1-C4-alkyl, C1-C4-alkyl-thio-C1-C4-alkyl, C2-C4-alkenyl-thio-C1-C4- alkyl, C2-C4-alkinyl-thio-C1-C4-alkyl, C1-C4-alkyl-sulphinyl-C1-C4 -alkyl, C1-C4-alkyl-sulphonyl-C1-C4-alkyl, halo-C1-C4-alkyl, cyano-C1-C 4-alkyl, 2,2-di-C1-C4-alkoxy-C1-C4-alkyl, 1,3-dioxolan-2-yl-C1-C4-alkyl, 1,3-dioxolan-4-yl-C1-C4-alkyl, 2,2-di-C1-C4-alkyl-1,3-dioxolan-4-yl-C1-C4-alkyl, 1,3-dioxan-2-yl-C1-C4-alkyl, 2-benzopyranyl-C1-C4-alkyl, C1-C4-alkoxycarbonyl or C2-C4-alkenyloxycarbonyl or tetrahydrofurfuryl-C1-C4-alkyl, the group P-X is also halo-C1-C4-alkyl, X is O, S, SO or SO2, n is 1, 2 or 3, A is a C1-C8-hydrocarbon radical, or a C1-C8-hydrocarbon radical which is substituted by alkoxy, alkylthio, fluorine, cyano or haloalkyl, and R13 is hydrogen, a C1-C5-hydrocarbon radical, a C1-C5-hydrocarbon radical which is substituted by alkoxy, polyalkoxy, halogen, cyano or trifluoromethyl, or C3-C8-cycloalkyl, C1-C4-alkyl-C3-C8-cycloalkyl, di-C1-C4-alkoxy-C1-C4-alkyl, 1,3-dioxolan-2-yl-C1-C4-alkyl, 1,3-dioxolan-4-yl-C1-C4-alkyl, 1,3-dioxan-2-yl-C1-C4-alkyl, furyl-C1-C4-alkyl, tetrahydrofuryl-C1-C4-alkyl, or a radical of the formula -NHCO2R01, -CH2CO2R01, -CH(CH3)CO2R01 or -CH(R 02)-C(R03)=NOR04 in which R01 is methyl, ethyl, propyl, isopropyl or allyl, R02 and R03 are in each case hydrogen or C1-C4-alkyl and R04 is hydrogen, C1-C4-alkyl, C2-C4-alkenyl or C2-C4-alkynyl, or   R is a radical of the formula (H5C2O)2P(O)CH2NHCO- or <IMAGE>  in which R15 and R16 independently of one another are hydroxyl, C1-C4-alkyl, aryl, C1-C4-alkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C2-C4-haloalkoxy, C2-C8-alkoxyalkoxy, C1-C4-cyanoalkoxy, C1-C4-phenylalkoxy or aryloxy, or aryloxy which is substituted by halogen, cyano, nitro or C1-C4-alkoxy, R17 is hydrogen, C1-C4-alkyl, phenyl or phenyl which is substituted by halogen, cyano, nitro or C1-C4-alkoxy,   R18 is hydrogen or C1-C4-alkyl, R19 is hydrogen or a radical of the formula -COCX1X2-R06 or an alkenoyl radical which has 2 to 4 carbon atoms in the alkenyl moiety and is substituted by halogen, X1 and X2 independently of one another being hydrogen or halogen, or a radical of the formula -COOR07 or -COR08, or a C1-C4-alkyl, C2-C4-alkenyl or C1-C4-phenylalkyl radical which can be substituted on the phenyl ring by halogen, cyano, nitro or C1-C4-alkoxy, and R20 is hydrogen, C1-C4-alkyl, C2-C4-alkenyl or C2-C4- alkynyl, R06 is hydrogen, halogen or C1-C6-alkyl, R07 is C1-C4-alkyl, C1-C4- phenylalkyl or C1-C4-phenylalkyl which is substituted in the phenyl moiety by halogen, cyano, nitro or C1-C4-alkoxy, and R08 is C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, phenyl, C1-C4-phenylalkyl or C1-C4-phenylalkyl which is substituted in the phenyl moiety by halogen, cyano, nitro or C1-C4-alkoxy, or   R is a radical of the formula <IMAGE>  or of the formula <IMAGE>  in which R21 is methyl, ethyl, propyl, 1-methylethyl, 2-propenyl, 2-butenyl, 1,1-dimethyl-2-propenyl, 2-propynyl or 2-methyl-2-propynyl, and R22, R23, R24 and R25 independently of one another are hydrogen or methyl, and   Y is chlorine or Y is hydrogen if R is a radical of the formula (H5C2O)2P(O)CH2NHCO-,     are highly suitable for controlling weeds in crops of useful plants, in particular maize.