Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1998-10-15
2000-04-04
Gerstl, Robert
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504269, 548204, 548214, A01N 4380, C07D41710
Patent
active
060461373
DESCRIPTION:
BRIEF SUMMARY
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-cyclopropyl-isoxazole, a representative class of compounds, is being developed by Rhone-Poulenc as a pre-emergence herbicidally active ingredient against mono- and dicotyledon harmful plants in maize. (RPA 201772, Technical Bulletin).
Moreover, the herbicidal and insecticidal activity of substituted 4-alkyl- and 4-cycloalkyl-5-aryl- or -5-hetaryl-isoxazole 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 insufficient post-emergence, but also only partially satisfactory pre-emergence combined with incomplete crop plant compatibility.
Herbicidal or insecticidal 4-benzoylisothiazoles according to the invention cannot be found in the prior art as yet.
As yet, 4-benzoylisothiazoles have only been of limited interest as far as synthesis is concerned. 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), only individual cases of acylated and, in particular, benzoylated derivatives have been described 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 investigated in EP 0 524 781 and EP 0 617 010 as muscle relaxants and as suitable therapeutic amides for incontinence. EP 0 449 223 maintains that 3,5-di(tertiary-butyl)-4-hydroxybenzoylisothiazoles, being 5-lipoxygenase and cyclooxygenase inhibitors, have an antiinflammatory action.
U.S. Pat. No. 5,034,385 discloses that carbapenem-substituted benzoylisothiazoles have an antibacterial activity.
It is an object of the present invention to provide novel herbicidally active substances with an improved profile of action and crop plant compatibility.
We have found that this object is achieved by the benzoylisothiazoles of the general formula 1 according to the invention, which, surprisingly, have crop plant compatibility combined with a pronounced herbicidal activity against harmful plants.
The present invention relates to 4-benzylisothiazoles of the general formula 1 ##STR3## where the substituents have the following meanings: X is oxygen or sulfur; alkoxycarbonyl; unsubstituted or substituted aryl, unsubstituted or substituted 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; aryl, it being possible for this radical to have attached to it one or more of the following groups: alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio or 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: alkoxy, alkenyloxy, aryloxy, alkylsulfonyl, alkenylsulfonyl or arylsulfonyl; alkylsulfonyl or alkoxycarbonyl; unsubstituted or substituted aryloxy or unsubstituted or substituted arylthio; unsubstituted or substituted mono- or dialkylamino, unsubstituted or substituted mono- or diarylamino or unsubstituted or substituted N-alkyl-N-arylamino, it being possible for alkyl and aryl to be identical or different; halogen, cyano or nitro; partially or fully ha
REFERENCES:
patent: 4187099 (1980-02-01), Franz et al.
patent: 5034385 (1991-07-01), Dininno et al.
patent: 5846907 (1998-12-01), Von Deyn
Deyn Wolfgang von
Engel Stefan
Hill Regina Luise
Kardorff Uwe
Misslitz Ulf
BASF - Aktiengesellschaft
Gerstl Robert
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