Naphthindazole-4,9-quinones and use thereof for controlling...

C - Chemistry – Metallurgy – 07 – D

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C07D 231/54 (2006.01) A01N 43/56 (2006.01) C07D 401/04 (2006.01) C07D 403/04 (2006.01) C07D 491/04 (2006.01)

Patent

CA 1331384

ABSTRACT OF THE DISCLOSURE Naphthindazole-4,9-quinones of the formula Image (I), where: R1 is C2-C10-alkyl, C3-C10-alkenyl, C2-C10-alkynyl, C1-C10-halo- alkyl, C1-C10-hydroxyalkyl, C2-C14-alkoxyalkyl, C2-C14-alkyl- thioalkyl, C3-C7-cycloalkyl, C1-C4-alkylcarbonyloxy-C1-C4-alkyl, C1-C4-alkylaminocarbonyloxy-C1-C4-alkyl, phenylaminocarbonyloxy- C1-C4-alkyl which is unsubstituted or substituted in the phenyl moiety by halogen, C1-C4-alkyl or C1-C4-alkoxy, phenylsulfonyl- oxy-C1-C4-alkyl which is unsubstituted or substituted in the phenyl moiety by halogen, C1-C4-alkyl or C1-C4-alkoxy, C1-C4-alkoxycarbonyl-C1-C4-alkyl, hydroxycarbonyl-C1-C4-alkyl, aminocarbonyl-C1-C4-alkyl, C1-C4-alkylaminocarbonyl-C1-C4-alkyl, di-(C1-C4-alkyl)-aminocarbonyl-C1-C4-alkyl, halo-C3-C4-alkynyl, unsubstituted or halogen- or C1-C4-alkyl-substituted heteroaryl radical with one or two nitrogen atoms, selected from the group consisting of pyrimidyl, pyridyl and imidazolyl, phenyl which is unsubstituted or substituted by halogen, hydroxy, nitro, amino, C1-C4-alkylamino, di-C1-C4-alkylamino, cyano, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkyl, C1-C4-alkylthio or C1-C4-haloalkylthio, or unsubstituted or halogen-substituted benzyl, and R2, R3, R4 and R5 are identical or different and each denotes hydrogen, halogen, nitro, cyano, hydroxy, amino, C1-C4-alkyl- amino, di-C1-C4-alkylamino, C1-C6-alkyl, C1-C5-haloalkyl, C1-C5-alkoxy, C1-C5-haloalkoxy, C1-C5-alkylthio, C1-C5-haloalkyl- thio, C2-C10-alkoxyalkyl, carboxyl, C2-C6-alkoxycarbonyl, C2-C6- alkanoyloxy, C2-C6-haloalkanoyloxy, C1-C4-alkylcarbonylamino, C1-C4-alkylaminocarbonyl, di-(C1-C4-alkyl)-aminocarbonyl, or phenyl or heteroaryl, selected from the group consisting of pyridyl, thienyl, furyl, benzimidazol-1-yl and pyrimid-2-yl, each of which phenyl or heteroaryl group is unsubstituted or substituted by halogen, trifluoromethyl, nitro, cyano, amino, C1-C4-alkoxy, C1-C4-alkylthio or C1-C5-haloalkylthio, and in addition R3 and R4, together with the two carbon atoms of the phenyl ring to which they are attached, form a heterocyclic ring selected from the group consisting of 1,4-dioxane, 1,3-dioxolane, pyrazole, indole, triophene, triazole and piperazine or a benzene or naphthalene ring which is unsub- stituted or substituted by halogen, nitro, cyano, amino, hydroxy, tri- fluoromethyl, C1-C5-alkyl, C1-C5-alkoxy, C1-C5-haloalkylthio, C1-C5- haloalkoxy or C1-C5-alkylthio and their use for combating unwanted plant growth.

610152

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