Herbicidal heterocyclically annulated benzoylisothiazoles

Details Herbicidal heterocyclically annulated benzoylisothiazoles Herbicidal heterocyclically annulated benzoylisothiazoles

1998-10-15

1999-08-31

Gerstl, Robert

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

548213, 548214, A01N 4380, C07D41706

Patent

active

059453818

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

The present invention relates to novel substituted benzoylisothiazoles, to processes for their preparation, and to their use as herbicides.
The patent literature (EP 0 527 036, EP 0 527 037, EP 0 560 482, EP 0 580 439, EP 0 588 357, EP 609 797, EP 0 609 798, EP 0 636 622, WO 94/14782, WO 94/ 18179, WO 95/15691 and WO 95/16678) discloses that substituted 4-benzoyl-5-cycloalkylisoxazoles represent a class of compounds with pronounced herbicidal activity pre-emergence. 4-(2-Sulfonylmethyl-4-trifluoromethylbenzoyl)-5-cyclopropylisoxazole, a representative of this class of compounds, is developed by Rhone-Poulenc as a herbicidal active ingredient against mono- and dicotyledon harmful plants used pre-emergence in maize (i.e. corn; RPA 201772, Technical Bulletin).
Moreover, the herbicidal and insecticidal activity of substituted 4-alkyl- or 4-cycloalkyl-5-aryl- or 5-hetaryl-isoxazoles has been disclosed (GB 2 284 600, Wo 95/22903, WO 95/22904 and WO 95/25105).
The herbicidal activity of the known compounds is not only deficient post-emergence, but also only partially satisfactorily pre-emergence and shows gaps with regard to its compatibility with crop plants.
To date, the prior art has not disclosed herbicidal or insecticidal 4-benzoylisothiazoles according to the invention.
With the view to their synthesis, 4-benzoylisothiazoles have only been of limited interest to date. While substituted isothiazoles and their carbocycle-fused derivatives have been the aim of basic investigations (for example: D. L. Pain, B. J. Peart, K. R. H. Wooldridge, Comprehensive Heterocyclic Chemistry, Vol. 6, Part 4B, p. 131, Ed. A. R. Katritzky, Pergamon Press, Oxford 1984), acylated and, in particular, benzoylated derivatives have only been described occasionally in the literature (for example: A. J. Layton, E. Lunt, J. Chem. Soc. (1968) 611, A. Alberola, F. Alonso, P. Cuadrado, C. M. Sanudo, Synth. Commun. 17 (1987) 1207, A. Alberola, F. Alonso, P. Cuadrado, C. M. Sanudo, J. Heterocycl. Chem. 25 (1988) 235).
Some hydroxypropylaminocarbonyl-substituted 4-benzoylisothiazoles have been examined in EP 0 524 781 and EP 0 617 010 as muscle-relaxing agents or suitable therapeutic amides in the case of incontinence. EP 0 449 223 claims that 3,5-di(tert-butyl)-4-hydroxybenzoylisothiazoles inhibit 5-lipoxygenase and cyclooxygenase and thus have an antiinflammatory activity.
It is an object of the present invention to provide novel herbicidally active ingredients which have an improved profile of is action and an improved crop plant compatibility.
Surprisingly, the benzoylisothiazoles of the general formula 1 according to the invention have a pronounced herbicidal activity against harmful plants combined with crop plant compatibility.
The present invention relates to 4-benzoylisothiazoles of the general formula 1 ##STR3## where the substituents have the following meanings: X is oxygen or sulfur; alkoxycarbonyl; heterocyclyl or unsubstituted or substituted hetaryl; it being possible for these radicals to have attached to them one or more of the following groups: halogen, alkyl, alkenyl or alkynyl; of the following groups: alkenylthio, it being possible for these radicals to be partially or fully halogenated or to have attached to them one or more of the following groups: arylsulfonyl; unsubstituted or substituted arylthio; substituted mono- or diarylamino or unsubstituted or substituted N-alkyl-N-arylamino, it being possible for alkyl and aryl to be identical or different; partially or fully halogenated or to have attached to them one or more of the following groups: for at least one of the nitrogens to have attached to it one of the following groups: alkynyloxy, cycloalkyloxy, haloalkoxy, unsubstituted or substituted aryl or unsubstituted or substituted aryloxy; ##STR4## where n, A, B and the substituents R.sup.4, R.sup.5 and R.sup.6 have the following meanings: R.sup.10 --), (--CR.sup.7 .dbd.CR.sup.8 --), (--CR.sup.7 R.sup.8 --CR.sup.7 .dbd.CR.sup.8 --) or a nitrogen atom which, in turn, can be substituted by a substituent selec

REFERENCES:
patent: 4187099 (1980-02-01), Franz et al.

Affiliated with

Also associated with

Rating

Herbicidal heterocyclically annulated benzoylisothiazoles does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Herbicidal heterocyclically annulated benzoylisothiazoles, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Herbicidal heterocyclically annulated benzoylisothiazoles will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2426485