Substituted 5-aminopyrazoles

C - Chemistry – Metallurgy – 07 – D

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C07D 231/38 (2006.01) A01N 25/32 (2006.01) A01N 43/56 (2006.01) A01N 47/36 (2006.01) A01N 57/32 (2006.01) C07D 231/40 (2006.01) C07D 401/02 (2006.01) C07D 403/04 (2006.01) C07D 413/02 (2006.01) C07F 9/547 (2006.01)

Patent

CA 2097418

2097418 9210480 PCTABS00013 Substituted 5-aminopyrazols have formula (I), in which R1 stands for C1-C8-alkyl, C1-C8-hydroxyalkyl, phenyl, that can also carry 1-3 of the following residues: halogen, nitro, alkyl, halogen alkyl, alkoxy, halogen alkoxy, alkylthio or -NR6R7, and that can in addition carry as many halogen atoms as necessary for the total number of residues to be 5; R6, R7 stand for H, C1-C4-alkyl; R2 stands for H, C1-C4-alkyl, C1-C4-halogen alkyl; R3 stands for CN, -CO-R8, -CS-R8; R8 stands for OH, C1-C4-alkoxy, NH2, C1-C4-alkylamino, di-(C1-C4)-alkylamino; R4, R5 stand for H, C1-C4-alkyl, -PX(OR9)2, -SO2-R9, -CX-R10, -CX-NH-CY-R9, CX-NH-SO2-R11; X, Y stand for O, S; R9 stands for one of the substituents named under R1; R10 stands for C1-C20-alkyl, C1-C4-alkoxy, if necessary substituted phenyl, NH2; R11 stands for NH2, C1-C4-alkylamino, di-(C1-C4)-alkylamino, pyrolidinyl, piperidinyl, morpholinyl; R4 and R5 together represent a group =CR12R13 or -CO-W-CO; R12 stands for H, NH2, C1-C4-alkylamino or C3-C8-cycloalkylamino; R13 stands for NH2, C1-C4-alkylamino, di-(C1-C4)alkylamino, C3-C8-cacloalkylamino, pyrrolidin-1-yl, pipieridin-1-yl, morpholin-4-yl, if necessary substituted phenyl or pyridyl; W stands for an ethylene or ethenylene bridge, if necessary substituted, a 5 or 6 membered, 1,2-C linked aromatic or heteroaromatic bridge, if necessary substituted, or a 5 or 6 membered, 1,2-C linked cycloalkylene or cycloalkenylene bridge, if necessary substituted. Also disclosed are the basic salts of such compounds (I), in which R3 stands for a hydroxycarbonyl or hydroxythiocarbonyl group, and the acid salts of such compounds (I), containing a basic nitrogen atom, with the exception of 1-phenyl- and 1-methyl-4-cyano-5-(acylamino)-pyrazol, 1-methyl-4-cyano-5-(chloromethylcarbonylamino)-pyrazol, 1-methyl-4-cyano-5-(phenylcarbonylamino)-pyrazol, 1-methyl-4-cyano-5-(p-chlorophenylcarbonylamino)-pyrazol, as well as the compounds (I), in which R1 stands for a methyl, phenyl, 4-chlorophenyl or 4-nitrophenyl group, R2 stands for hydrogen, a methyl or trifluoromethyl group, R3 stands for a cyano group and R4 and R5 simultaneously stand for hydrogen. Also disclosed are herbicides that contain 2-(4-heteroaryloxy)- and 2-(4-aryloxy)- phenoxyacetic acid or propionic acid derivatives and/or cyclohexenone derivatives as herbicidal active substances and substituted 5-aminopyrazols I' as antidotes, as well as the salts of I', if acid terminal groups or basic nitrogen atoms are present.

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