Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1998-10-15
2000-07-04
Stockton, Laura L.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
548214, 548213, A01N 4380, C07D27502, C07D27503
Patent
active
060838795
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
The present invention relates to novel substituted benzoylisothiazoles, processes for their preparation, and 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 substituted 4-benzoyl-5-cycloalkylisoxazoles as a class of compounds which have a pronounced herbicidal activity pre-emergence. 4-(2-Sulfonylmethyl-4-trifluoromethylbenzoyl)-5-cyclopropyl-isoxazole, a representative of this class of compound, is developed by Rhone-Poulenc as a herbicidally active substance used pre-emergence against harmful mono- and dicotyledons in maize (RPA 201772, Technical Bulletin).
Moreover, the herbicidal and insecticidal activity of substituted 4-alkyl- and 4-cycloalkyl-5-aryl- or -5-hetarylisoxazoles 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 insufficiently effective post-emergence, but also only partly satisfactory pre-emergence and combined with incomplete crop plant compatibility.
Herbicidal or insecticidal 4-benzoylisothiazoles according to the invention have not been found in the prior art as yet.
As yet, 4-benzoylisothiazoles have only been of moderate interest with a view to their synthesis. While substituted isothiazoles and their carbocycle-fused derivatives have been the object 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-relaxing agents and as suitable therapeutic amides to treat incontinence. EP 0 449 223 maintains that 3,5-di(tertiary-butyl)-4-hydroxybenzoylisothiazoles are inhibitors of 5-lipoxygenase and cyclooxygenase and thus have an antiinflammatory action.
It is an object of the present invention to provide novel herbicidally active ingredients with an improved profile of action and improved crop plant compatibility.
Surprisingly, the benzoylisothiazoles of the general formula 1 according to the invention show a pronounced herbicidal activity against harmful plants combined with crop plant compatibility.
The present invention relates to 4-benzoylisothiazoles of the general formula 1 ##STR2## 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: arylsulfonyl; 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: 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; partially or fully halogenated or to have attached to them one or more of the following groups: alkenylthio,
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Deyn Wolfgang von
Engel Stefan
Hill Regina Luise
Kardorff Uwe
Misslitz Ulf
BASF - Aktiengesellschaft
Stockton Laura L.
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