Substituted N-phenylglutarimides and N-phenylglutaramides, their

Plant protecting and regulating compositions – Plant growth regulating compositions – Abscission agent – defoliant – or desiccant

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546219, A01N 4340, C07D21140, C07D40110

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active

056984944

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP93/02879, filed Oct. 19, 1993.


DESCRIPTION

The present invention relates to novel substituted N-phenylglutarimides of the formula I ##STR2## where the variables have the following meanings: X.sup.1, X.sup.2 -alkyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, phenyl or benzyl, where the phenyl group or the phenyl ring of the benzyl group may be substituted by C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, halogen, cyano, nitro or trifluoromethyl, one another via a 2- to 5-membered chain and thus form a spiro ring, which, if desired, can carry one or two halogen atoms, the spiro ring in addition to the C atoms also being able to contain one or two non-adjacent ring members selected from the group consisting of --O--, --S--, --NH--, and --N(C.sub.1 -C.sub.4 -alkyl)--, are bonded to one another via a 1- to 5-membered chain and thus form a fused ring, which, if desired, can carry one or two halogen atoms, the fused ring in addition to the C atoms also being able to contain one or two non-adjacent ring members selected from the group consisting of --O--, --S--, --NH-- and --N(C.sub.1 -C.sub.4 -alkyl)--; -haloalkyl; -alkoxy or C.sub.1 -C.sub.6 -alkylcarbonyloxy, and -C.sub.6 -haloalkyl, hydroxyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl or C.sub.1 -C.sub.6 -alkylcarbonyloxy
B has one of the following meanings: -alkynyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -dialkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkyl; -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.7 -cycloalkyl, halo-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.3 -C.sub.6 -haloalkenyl, C.sub.1 -C.sub.6 -alkoxycarbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkylimino or C.sub.1 -C.sub.6 -alkyloximino-C.sub.1 -C.sub.6 -alkyl, phenyl, phenyl substituted by one or more C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkoxycarbonyl radicals, benzyl or benzyl substituted by one or more C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkoxycarbonyl radicals; another have the following meanings: -C.sub.6 -alkynyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, phenyl, phenyl substituted by one to three C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl, halogen, cyano, nitro, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkoxycarbonyl radicals, or R.sup.10 and R.sup.11, together with the nitrogen atom to which they are bonded, are a saturated or unsaturated 4- to 7- membered heterocycle having one or two further identical or different heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur; N-phenylglutarimides I.
In particular, the invention relates to substituted N-phenylglutarimides of the formula I where R.sup.3 is C.sub.1 -C.sub.6 -alkyl or -haloalkyl and R.sup.4, R.sup.5 are hydrogen or C.sub.1 -C.sub.4 -alkyl and to glutarimides of the formula I' ##STR3## where R.sup.4 is C.sub.1 -C.sub.6 -haloalkyl, R.sup.3 and R.sup.5 are hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl and A, X.sup.1 and X.sup.2 are as defined above.
Additionally, the invention relates to herbicidal and desiccant and/or defoliant compositions which contain these compounds as active substances.
A further aspect of the invention relates to N-phenylglutaramides of the ge

REFERENCES:
patent: 3655669 (1972-04-01), Ackerman
patent: 5180418 (1993-01-01), Pissiotas et al.
patent: 5223018 (1993-06-01), Moser
patent: 5393735 (1995-02-01), Lange

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