1,8-napthalenedicarboximides as antidotes

C - Chemistry – Metallurgy – 07 – D

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260/237.1, 260/2

C07D 221/14 (2006.01) A01N 25/32 (2006.01) C07D 401/12 (2006.01) C07D 405/12 (2006.01) C07D 409/12 (2006.01) C07D 471/06 (2006.01)

Patent

CA 2030129

Abstract of the Disclosure: 1,8-Naphthalanedicarbox- imides of the formula Ia Image I where R1 to R4 are each H, halogen, OH, SH, CN, SCN, NO2, alkyl which may be halogenated, alkenyl, alkynyl, cycloalkyl, cycloalkoxy, NH2, alkylamino, dialkylamino, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxy, alkylthio, alkoxyalkyl, alkylthioalkyl, alkylcarbonyl, alkylcar- bonyloxy, alkoxycarbonyl, COOH, hydroxycarbonylalkyl, hydroxycarbonylalkoxy, hydroxycarbonylalkylthio, SO3H, alkylsulfinyl, alkylsulfonyl, alkoxysulfonyl, SO2NH2, alkylaminosulfonyl, dialkylaminosulfonyl, unsubstituted or substituted NHNH2, C6H5, phenylalkyl, naphthyl, naph- thylalkyl, hetaryl, hetarylalkyl, phenoxy, naphthyloxy, phenylthio, naphthylthio, phenoxycarbonyl, naphthyloxy- carbonyl, phenylcarbonyl, naphthylcarbonyl, phenyl- carbonyloxy, naphthylcarbonyloxy, phenylalkoxy, naphthyl- alkoxy, hetarylalkoxy, phenylsulfinyl, naphthylsulfinyl, hetarylsulfinyl, phenylsulfonyl, naphthylsulfonyl, hetarylsulfonyl, phenoxysulfonyl, naphthyloxysulfonyl or hetaryloxysulfonyl, where all aryl moieties may carry further substituents; X is an unsubstituted or sub- stituted alkylene chain; R5 is H, CN, alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, alkoxyoarbonyl, acetyl, cycloalkyl, benzoyl, naphthoyl, hetaroyl, C6H5, naphthyl, phenylalkyl, naphthylalkyl, hetaryl or hetarylalkyl, where the aryl moieties of the six last-mentioned radicals may carry further substituents; R6 is H, CN, alkyl which may be halogenated, alkoxy, alkoxyalkyl, diazolylmethyl, triazolylmethyl, alkoxycarbonyl, furyl, tetrahydrofuryl, thienyl, tetrahydropyranyl, tetrahydro- thiopyranyl, dihydropyranyl or dihydrothiopyranyl; R6 is C6H5 if R5 is H, CH3 or CH3CO; R5 and R6, together with the common carbon atom, form a cycloalkyl radical or an unsubstituted or substituted 5-membered or 6-membered ring which may be unsaturated and may contain O or S as hetero atoms, and Y and Z are each O and S, with the exception of compounds in which R3 and R4 are simultan- eously H, and, where R1 to R4 are each an acidic group, the plant- tolerated salts of Ia, and herbicides which contain the 2-(4-hetaryloxy)- or 2-(4-aryloxy)-phenoxyacetic acid or -propionic acid derivatives and/or cyclohexenone deriva- tives as herbicidal active ingredients and 1,8- naphthalenedicarboximides Ia and/or Ib Image Ib where R7 is an organic radical and may have different meanings, and/or Ic Image Ic and, in the case of acidic terminal groups, the plant- tolerated salts of Ia and/or Ib and/or Ic as antidotes.

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