Substituted phthalimidocinnamic acid derivatives and intermediat

Details Substituted phthalimidocinnamic acid derivatives and intermediat Substituted phthalimidocinnamic acid derivatives and intermediat

1997-04-07

1998-01-13

Powers, Fiona T.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

546187, 548465, 548476, 560 23, 560 45, A01N 4338, C07D20948

Patent

active

057079374

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP95/04067 filed Oct. 17, 1995.
The present invention relates to novel substituted phthalimidocinnamic acid derivatives of the formula I ##STR2## where R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl; -haloalkyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -haloalkoxy; C.sub.2 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.6 -hydroxyalkyl, C.sub.1 -C.sub.6 -mercaptoalkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkyl; 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.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl-C.sub.1 -C.sub.6 -alkyl, hydroxycarbonyl-C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkylamino)carbonyl-C.sub.1 -C.sub.6 -alkyl, di(C.sub.1 -C.sub.6 -alkyl)aminocarbonyl-C.sub.1 -C.sub.6 -alkyl, aminocarbonyl-C.sub.1 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkyl)carbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoximino-C.sub.1 -C.sub.6 -alkyl, hydroximino-C.sub.1 -C.sub.6 -alkyl, di(C.sub.1 -C.sub.6 -alkoxy)-C.sub.1 -C.sub.6 -alkyl, di(C.sub.1 -C.sub.6 -alkylthio)-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -haloalkenyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl, hydroxycarbonyl, (C.sub.1 -C.sub.6 -alkylamino)carbonyl, di(C.sub.1 -C.sub.6 -alkyl)aminocarbonyl, aminocarbonyl(C.sub.1 -C.sub.6 -alkyl)carbonyl, (C.sub.1 -C.sub.6 -haloalkyl)carbonyl, aryl, hetaryl, aryl-C.sub.1 -C.sub.6 -alkyl or hetaryl-C.sub.1 -C.sub.6 -alkyl, where the aryl and hetaryl rings may, if desired, carry from one to three radicals selected from the group consisting of cyano, nitro, halogen, C.sub.1 -C.sub.6 -alkyl, 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, hydroxyl, mercapto and (C.sub.1 -C.sub.6 -alkoxy)carbonyl; chain in which a methylene unit may be replaced by oxygen or C.sub.1 -C.sub.4 -alkylimino; C.sub.3 -C.sub.6 -alkynyl, C.sub.2 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -cyanoalkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.2 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkylthio-C.sub.2 -C.sub.6 -alkyl, (C.sub.1 -C.sub.6 -alkoxy)carbonyl-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyl-C.sub.1 -C.sub.6 -alkyl, radicals selected from the group consisting of cyano, nitro, halogen, C.sub.1 -C.sub.6 -alkyl, 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 and (C.sub.1 -C.sub.6 -alkoxy)carbonyl; -alkoxy)carbonyl, (C.sub.1 -C.sub.6 -haloalkoxy)carbonyl, (C.sub.1 -C.sub.6 -alkyl)carbonyl, (C.sub.1 -C.sub.6 -haloalkyl)carbonyl, tri(C.sub.1 -C.sub.6 -alkyl)silyl, aryloxycarbonyl or arylmethoxycarbonyl in which a nonterminal methylene unit may be replaced by oxygen or C.sub.1 -C.sub.4 -alkylimino or in which the N-bonded methylene unit may be replaced by carbonyl,
The present invention furthermore relates to novel intermediates of the formulae IIa and IIb, where R.sup.2 to R.sup.7 and X have the same meanings as in the case of the compounds I.
The present invention furthermore relates to defoliation of plants, compounds I as active ingredients, plant desiccants and/or defoliants using the compounds I and defoliating plants with the compounds I.
EP-A 240 659, EP-A 300 387 and EP-A 400 427 disclose herbicidal cinnamic acid derivatives. However, their action is not always completely satisfactory, especially at low application rates.
It is an object of the present invention to provide cinnamic acid derivatives having improved herbicidal activity.
We have found that this object is achieved by the substituted phthalimidocinnamic acid derivatives of the formula I which are defined at the outset. We have also found herbicides which contain the compounds I and have very good herbicidal activity. We have furthermore found processes for the preparation of these

REFERENCES:
patent: 5009701 (1991-04-01), Plath et al.
patent: 5123955 (1992-06-01), Plath et al.
patent: 5356860 (1994-10-01), Schaefer et al.

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