Substituted 2-phenylpyridines
First Claim
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1. A substituted 2-phenylpyridine of the general formula I ##STR35## where the variables have the following meanings:
- n is 0 or 1;
R1 and R3 are hydrogen;
R2 is C1 -C4 -haloalkyl;
R4 is halogen;
R5 is hydrogen, halogen or cyano;
R6 and R13 independently of one another are hydrogen or halogen;
X is methylene or carbonyl;
R7, R8, R9, R10 independently of one another are hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy or nitro;
R11 is hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -hydroxyalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, C3 -C6 -cycloalkyl, C2 -C4 -alkenyl, C2 -C4 -alkynyl, hydroxycarbonyl-C1 -C4 -alkyl, hydroxycarbonyl-C2 -C4 -alkenyl, hydroxycarbonyl-C2 -C4 -alkynyl, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl, (C1 -C4 -alkoxy)carbonyl-C2 -C4 -alkenyl, (C1 -C4 -alkoxy)carbonyl-C2 -C4 -alkynyl, (C1 -C4 -alkoxy)carbonyl-C2 -C4 -haloalkyl, (C1 -C4 -alkoxy)carbonyl-C2 -C4 -haloalkenyl, aminocarbonyl-C1 -C4 -alkyl, aminocarbonyl-C2 -C4 -alkenyl, aminocarbonyl-C2 -C4 -alkynyl, C1 -C4 -alkylaminocarbonyl-C1 -C4 -alkyl, C1 -C4 -alkylaminocarbonyl-C2 -C4 -alkenyl, C1 -C4 -alkylaminocarbonyl-C2 -C4 -alkynyl, di(C1 -C4 -alkyl)aminocarbonyl-C1 -C4 -alkyl, di(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -alkenyl, di(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -alkynyl, aminocarbonyl-C1 -C4 -haloalkyl, aminocarbonyl-C2 -C4 -haloalkenyl, C1 -C4 -alkylaminocarbonyl-C1 -C4 -haloalkyl, C1 -C4 -alkylaminocarbonyl-C2 -C4 -haloalkenyl, di(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -haloalkyl, di(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -haloalkenyl, (hydroxycarbonyl-C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -alkenyl, (hydroxycarbonyl-C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -haloalkenyl, N-(hydroxycarbonyl-C1 -C4 -alkyl)-N-(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -alkenyl, N-(hydroxycarbonyl-C1 -C4 -alkyl)-N-(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -haloalkenyl, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!-aminocarbonyl-C2 -C4 -alkenyl, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!aminocarbonyl-C2 -C4 -haloalkenyl, N- (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!-N-(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -alkenyl, N- (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!-N-(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -haloalkenyl, 2- (C1 -C4 -alkoxy)carbonyl!-pyrrolidin-1-yl-carbonyl-C2 -C4 -alkenyl, 2- (C1 -C4 -alkoxy)carbonyl!-pyrrolidin-1-ylcarbonyl-C2 -C4 -haloalkenyl, formyl, (C1 -C4 -alkyl)carbonyl, (C1 -C4 -haloalkyl)carbonyl, hydroxyimino-C1 -C4 -alkyl, C1 -C4 -alkoxyimino-C1 -C4 -alkyl, 1,1-di(C1 -C4 -alkoxy)-C1 -C4 -alkyl, 1,1-di(C1 -C4 -alkylthio) -C1 -C4 -alkyl,nitro, hydroxylamino, amino, C1 -C4 -alkylamino, C3 -C6 -cycloalkylamino, di(C1 -C4 -alkyl)amino, (C1 -C4 -alkyl)carbonylamino, (C1 -C4 -haloalkyl)carbonylamino, C1 -C4 -alkylsulfonylamino, di(C1 -C4 -alkylsulfonyl)amino, C1 -C4 -haloalkylsulfonylamino, hydroxyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, cyano-C1 -C4 -alkoxy, C1 -C4 -alkoxy-C1 -C4 -alkoxy, C1 -C4 -alkylthio-C1 -C4 -alkoxy, C3 -C6 -cycloalkoxy, C2 -C4 -alkenyloxy, C2 -C4 -alkynyloxy, hydroxycarbonyl-C1 -C4 -alkoxy, (C1 -C6 -alkoxy)carbonyl-C1 -C4 -alkoxy, C1 -C4 -alkoxy-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, (C1 -C4 -alkoxy)carbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, aminocarbonyl-C1 -C4 -alkoxy, C1 -C4 -alkylaminocarbonyl-C1 -C4 -alkoxy, di(C1 -C4 -alkyl)aminocarbonyl-C1 -C4 -alkoxy, 1-pyrrolidinylcarbonyl-C1 -C4 -alkoxy, 1-piperidinyl-carbonyl-C1 -C4 -alkoxy, 4-morpholinylcarbonyl-C1 -C4 -alkoxy, aminocarbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, (C1 -C4 -alkyl)aminocarbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, di(C1 -C4 -alkyl)aminocarbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, -pyrrolidinyl-carbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, 1-piperidinylcarbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, 4-morpholinylcarbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!aminocarbonyl-C1 -C4 -alkoxy, N- (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!-N-(C1 -C4 -alkyl)aminocarbonyl-C1 -C4 -alkoxy, 2- (C1 -C4 -alkoxy)carbonyl!pyrrolidin-1-yl!carbonyl-C1 -C4 -alkoxy, cyano, hydroxycarbonyl, COCl, (C1 -C4 -alkoxy)carbonyl, (C1 -C4 -haloalkoxy)carbonyl, C1 -C4 -alkoxy-(C1 -C4 -alkoxy)carbonyl, aminocarbonyl, C1 -C4 -alkylaminocarbonyl, di(C1 -C4 -alkyl)aminocarbonyl, C3 -C6 -cycloalkylaminocarbonyl, 1-pyrrolidinylcarbonyl, 1-piperidinylcarbonyl, 4-morpholinylcarbonyl, hydroxycarbonyl-C1 -C4 -alkylaminocarbonyl, N-(hydroxycarbonyl-C1 -C4 -alkyl)-N-(C1 -C4 -alkyl)-aminocarbonyl, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkylaminocarbonyl, N- (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!-N-(C1 -C4 -alkyl)aminocarbonyl, 2-hydroxycarbonylpyrrolidin-1-yl-carbonyl, 2- (C1 -C4 -alkoxy)carbonyl!pyrrolidin-1-yl-carbonyl or a group ##STR36## where Y and Z independently of one another are oxygen or sulfur,R14 is hydrogen, C1 -C4 -alkyl or (C1 -C4 -alkoxy)carbonyl andAlk is an ethylene or trimethylene chain where one or more hydrogen atoms can be replaced in each case by C1 -C4 -alkyl or (C1 -C4 -alkoxy)carbonyl;
R12 is hydrogen, nitro, amino, hydroxylamino, C1 -C4 -alkylsulfonylamino, di(C1 -C4 -alkylsulfonyl)amino, C1 -C4 -haloalkylsulfonylamino, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -haloalkyl or (C1 -C4 -alkoxy)carbonyl-C2 -C4 -haloalkenyl;
with the proviso that R5, R7, R11 and R13 are not all simultaneously hydrogen or R7 and R8 or R10 and R11 are not simultaneously fluorine,or an agriculturally useful salt thereof.
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Abstract
Substituted 2-phenylpyridines I ##STR1## wherein all variables are as defined in the specification are used as herbicides and for the desiccation/defoliation of plants.
14 Citations
6 Claims
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1. A substituted 2-phenylpyridine of the general formula I ##STR35## where the variables have the following meanings:
- n is 0 or 1;
R1 and R3 are hydrogen; R2 is C1 -C4 -haloalkyl; R4 is halogen; R5 is hydrogen, halogen or cyano; R6 and R13 independently of one another are hydrogen or halogen; X is methylene or carbonyl; R7, R8, R9, R10 independently of one another are hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -alkoxy or nitro; R11 is hydrogen, halogen, C1 -C4 -alkyl, C1 -C4 -haloalkyl, C1 -C4 -hydroxyalkyl, C1 -C4 -alkoxy-C1 -C4 -alkyl, C3 -C6 -cycloalkyl, C2 -C4 -alkenyl, C2 -C4 -alkynyl, hydroxycarbonyl-C1 -C4 -alkyl, hydroxycarbonyl-C2 -C4 -alkenyl, hydroxycarbonyl-C2 -C4 -alkynyl, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl, (C1 -C4 -alkoxy)carbonyl-C2 -C4 -alkenyl, (C1 -C4 -alkoxy)carbonyl-C2 -C4 -alkynyl, (C1 -C4 -alkoxy)carbonyl-C2 -C4 -haloalkyl, (C1 -C4 -alkoxy)carbonyl-C2 -C4 -haloalkenyl, aminocarbonyl-C1 -C4 -alkyl, aminocarbonyl-C2 -C4 -alkenyl, aminocarbonyl-C2 -C4 -alkynyl, C1 -C4 -alkylaminocarbonyl-C1 -C4 -alkyl, C1 -C4 -alkylaminocarbonyl-C2 -C4 -alkenyl, C1 -C4 -alkylaminocarbonyl-C2 -C4 -alkynyl, di(C1 -C4 -alkyl)aminocarbonyl-C1 -C4 -alkyl, di(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -alkenyl, di(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -alkynyl, aminocarbonyl-C1 -C4 -haloalkyl, aminocarbonyl-C2 -C4 -haloalkenyl, C1 -C4 -alkylaminocarbonyl-C1 -C4 -haloalkyl, C1 -C4 -alkylaminocarbonyl-C2 -C4 -haloalkenyl, di(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -haloalkyl, di(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -haloalkenyl, (hydroxycarbonyl-C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -alkenyl, (hydroxycarbonyl-C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -haloalkenyl, N-(hydroxycarbonyl-C1 -C4 -alkyl)-N-(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -alkenyl, N-(hydroxycarbonyl-C1 -C4 -alkyl)-N-(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -haloalkenyl, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!-aminocarbonyl-C2 -C4 -alkenyl, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!aminocarbonyl-C2 -C4 -haloalkenyl, N- (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!-N-(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -alkenyl, N- (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!-N-(C1 -C4 -alkyl)aminocarbonyl-C2 -C4 -haloalkenyl, 2- (C1 -C4 -alkoxy)carbonyl!-pyrrolidin-1-yl-carbonyl-C2 -C4 -alkenyl, 2- (C1 -C4 -alkoxy)carbonyl!-pyrrolidin-1-ylcarbonyl-C2 -C4 -haloalkenyl, formyl, (C1 -C4 -alkyl)carbonyl, (C1 -C4 -haloalkyl)carbonyl, hydroxyimino-C1 -C4 -alkyl, C1 -C4 -alkoxyimino-C1 -C4 -alkyl, 1,1-di(C1 -C4 -alkoxy)-C1 -C4 -alkyl, 1,1-di(C1 -C4 -alkylthio) -C1 -C4 -alkyl, nitro, hydroxylamino, amino, C1 -C4 -alkylamino, C3 -C6 -cycloalkylamino, di(C1 -C4 -alkyl)amino, (C1 -C4 -alkyl)carbonylamino, (C1 -C4 -haloalkyl)carbonylamino, C1 -C4 -alkylsulfonylamino, di(C1 -C4 -alkylsulfonyl)amino, C1 -C4 -haloalkylsulfonylamino, hydroxyl, C1 -C4 -alkoxy, C1 -C4 -haloalkoxy, cyano-C1 -C4 -alkoxy, C1 -C4 -alkoxy-C1 -C4 -alkoxy, C1 -C4 -alkylthio-C1 -C4 -alkoxy, C3 -C6 -cycloalkoxy, C2 -C4 -alkenyloxy, C2 -C4 -alkynyloxy, hydroxycarbonyl-C1 -C4 -alkoxy, (C1 -C6 -alkoxy)carbonyl-C1 -C4 -alkoxy, C1 -C4 -alkoxy-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, (C1 -C4 -alkoxy)carbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, aminocarbonyl-C1 -C4 -alkoxy, C1 -C4 -alkylaminocarbonyl-C1 -C4 -alkoxy, di(C1 -C4 -alkyl)aminocarbonyl-C1 -C4 -alkoxy, 1-pyrrolidinylcarbonyl-C1 -C4 -alkoxy, 1-piperidinyl-carbonyl-C1 -C4 -alkoxy, 4-morpholinylcarbonyl-C1 -C4 -alkoxy, aminocarbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, (C1 -C4 -alkyl)aminocarbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, di(C1 -C4 -alkyl)aminocarbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, -pyrrolidinyl-carbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, 1-piperidinylcarbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, 4-morpholinylcarbonyl-(C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkoxy, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!aminocarbonyl-C1 -C4 -alkoxy, N- (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!-N-(C1 -C4 -alkyl)aminocarbonyl-C1 -C4 -alkoxy, 2- (C1 -C4 -alkoxy)carbonyl!pyrrolidin-1-yl!carbonyl-C1 -C4 -alkoxy, cyano, hydroxycarbonyl, COCl, (C1 -C4 -alkoxy)carbonyl, (C1 -C4 -haloalkoxy)carbonyl, C1 -C4 -alkoxy-(C1 -C4 -alkoxy)carbonyl, aminocarbonyl, C1 -C4 -alkylaminocarbonyl, di(C1 -C4 -alkyl)aminocarbonyl, C3 -C6 -cycloalkylaminocarbonyl, 1-pyrrolidinylcarbonyl, 1-piperidinylcarbonyl, 4-morpholinylcarbonyl, hydroxycarbonyl-C1 -C4 -alkylaminocarbonyl, N-(hydroxycarbonyl-C1 -C4 -alkyl)-N-(C1 -C4 -alkyl)-aminocarbonyl, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkylaminocarbonyl, N- (C1 -C4 -alkoxy)carbonyl-C1 -C4 -alkyl!-N-(C1 -C4 -alkyl)aminocarbonyl, 2-hydroxycarbonylpyrrolidin-1-yl-carbonyl, 2- (C1 -C4 -alkoxy)carbonyl!pyrrolidin-1-yl-carbonyl or a group ##STR36## where Y and Z independently of one another are oxygen or sulfur, R14 is hydrogen, C1 -C4 -alkyl or (C1 -C4 -alkoxy)carbonyl and Alk is an ethylene or trimethylene chain where one or more hydrogen atoms can be replaced in each case by C1 -C4 -alkyl or (C1 -C4 -alkoxy)carbonyl; R12 is hydrogen, nitro, amino, hydroxylamino, C1 -C4 -alkylsulfonylamino, di(C1 -C4 -alkylsulfonyl)amino, C1 -C4 -haloalkylsulfonylamino, (C1 -C4 -alkoxy)carbonyl-C1 -C4 -haloalkyl or (C1 -C4 -alkoxy)carbonyl-C2 -C4 -haloalkenyl; with the proviso that R5, R7, R11 and R13 are not all simultaneously hydrogen or R7 and R8 or R10 and R11 are not simultaneously fluorine, or an agriculturally useful salt thereof. - View Dependent Claims (2, 3, 4, 5, 6)
- n is 0 or 1;
Specification
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Current AssigneeBASF AG (BASF SE)
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Original AssigneeBASF AG (BASF SE)
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InventorsSchaefer, Peter, Walter, Helmut, Hamprecht, Gerhard, Westphalen, Karl-Otto, Misslitz, Ulf, Heistracher, Elisabeth, Klintz, Ralf, Konig, Hartmann
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Primary Examiner(s)FAN, JANE T
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Application NumberUS08/849,874Time in Patent Office832 DaysField of Search504/244, 504/225, 504/248, 504/252, 504/260, 546/339, 546/276.4, 546/194, 544/124US Class Current504/244CPC Class CodesA01N 43/40 six-membered ringsC07D 213/61 Halogen atoms or nitro radi...
