1h-imidazole-5-carboxylic acid derivatives

Details 1h-imidazole-5-carboxylic acid derivatives 1h-imidazole-5-carboxylic acid derivatives

C - Chemistry, Metallurgy

07

D

260/305, 260/241

C07D 405/04 (2006.01) A01N 43/50 (2006.01) A01N 43/56 (2006.01) C07D 401/04 (2006.01) C07D 403/04 (2006.01) C07D 409/04 (2006.01)

Patent

CA 1291755

ABSTRACT 1H-IMIDAZOLE-5-CARBOXYLIC ACID DERIVATIVES Novel herbicidal 1-heterocyclyl-1H-imidazole-5- carboxylic acid derivatives, compositions containing thes compounds as active ingredients, and a method for controlling weeds, preferably selectively in crops of useful plants. Further the invention also relates to a process for making these novel compounds. The compounds of the present invention are directed to those having the general formula Image (I) or a stereochemically isomeric form thereof, or a salt thereof, or a quaternised form thereof, or a N-oxide thereof wherein R1 is hydrogen or mercapto, R2 is hydrogen, C1-C7alkyl, C3-C7alkenyl, C3-C7alkynyl, C3-C7cycloalkyl, C1-C7alkyloxy-C1-C7alkyl or arylC1-C5alkyl; n is zero, one or two; Y is a group -CH2-S(O)m-, -CH2-O-, -CH2-N(E)-, or -CH=N-, wherein the hereoatom is linked to the carbon atom of the benzene ring and wherein m is zero, one or two: E is hydrogen, C1-C5alkyl, C1-C5alkanoyl, or 4-methylphenylsulfonyl; R3, R4, R5 and R6 are each independently hydrogen, C1-C6alkyl, mono- and di-(aryl)C1-C5alkyl, C1-C6alkyloxy, halo, C3-C7alkenyl, C1-C5alkyl substituted With one to three halo atoms, C1-C5alkyloxy substituted with one to three halo atoms or aryl; or R3 and R4 toqether may form a fused benzene residue which may optionally be substituted with one or two substituents each independently selected from hydrogen, C1-C5alkyl, C1-C5alkyloxy, halo, C1-C5alkyl substituted with one to three halo atoms, C1-C5alkyloxy substituted with one to three halo atoms, nitro, amino and -NH-CO-G; or where R3 and R4 are geminally substituted, they may form a spirocyclic carbon ring with 3 to 7 carbon atoms; and R7 and R8 are each independently hydrogen, C1-C5alkyl, C1-C5alkyloxy, halo, C1-C5alkyl substituted with one to three halo atoms, C1-C5alkyloxy substituted with one to three halo atoms, cyano, nitro, amino, mono- and di-C1-C5alkylamino or -NH-CO-G; G is C1-C6alkyl; and aryl is phenyl optionally substituted with one to three substituents each independently selected from C1-C5alkyl, C1-C5alkyloxy and halo; whereby the radicals R3, R4, R5 and R6 as defined above may be substituted to any carbon atom making up the Y containing part of the bicyclic ring system, including the CH2 or CH-groups of either the -(CH2)n- or -CH2S-, -CH2O-, -CH2N(E)- or -CH=N- fragments.

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