Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1995-05-12
1997-06-10
Ivy, C. Warren
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
546111, A01N 4342, C07D22116
Patent
active
056375549
DESCRIPTION:
BRIEF SUMMARY
This application is the national phase of PCT/EP94/00071 filed on Jan. 12, 1994.
The present invention relates to 4-methyl-5H-indeno[3,2-b]pyridines and 1-methyl-9H-indeno[2,3-c]pyridines of the formula I ##STR2## where X, Y, Z and the radicals R.sup.1 to R.sup.5 have the following meanings: being C.sub.1 -C.sub.4 -alkyl, -C.sub.4 -alkyl, substituents: halogen, hydroxyl or C.sub.1 -C.sub.6 -alkoxy, following substituents: nitro, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl; C.sub.1 -C.sub.2 -alkyl, COOH or COOR.sup.6, with the proviso that exclusively one nitrogen atom or one N-oxide group is contained in the ring; group, W being oxygen or the --N(R.sup.10) group and where substituted by halogen, COOR.sup.6 or C.sub.1 -C.sub.4 -alkoxy, a C.sub.3 -C.sub.6 -alkenyl group, a C.sub.3 -C.sub.6 -haloalkenyl group, a C.sub.3 -C.sub.6 -alkynyl group, or phenyl, phenyl-C.sub.1 -C.sub.4 -alkyl or mononuclear heteroaryl or heteroaryl-C.sub.1 -C.sub.4 -alkyl radicals, these aromatic or heteroaromatic groups being able to carry one to three of the following substituents on the ring: halogen, nitro, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.2 -haloalkyl, amino, C.sub.1 -C.sub.6 -alkylamino or di(C.sub.1 -C.sub.6 -alkyl)amino and herbicidal or the plant growth-regulating action of I, excluding onychine, 6-, 7-, 8- and 9-methoxyonychine, 6-, 7-, 8- and 9-hydroxyonychine, 7,8-dimethoxyonychine and 4-methyl-5H-indeno-[3,2-b]pyridines of the formula Ia ##STR3## where two of the radicals R.sup.2, R.sup.3, R.sup.4 and R.sup.5 form a combination of methoxy and hydroxyl if Z is C.dbd.O or CHOH and the remaining two radicals are hydrogen or methoxy.
The alkaloid onychine or 4-methyl-5H-indeno[3,2-b]pyridin-5-one, which was isolated from the plant Onychopetalum amazonicum, is known from the investigations of J. Koyama et al. (Heterocycles 12 (1979), 1017-1019) and V. Sniekus et al. (Tetrahedron Lett., 29 (1988), 2135-2136). Other alkaloids structurally related to onychine, such as, for example, 8-methoxyonychine (M. O. F. Goulart et al., Phytochemistry 25 (1986), 1691-95 and Phytochemistry 26 (1987), 1551-1552) isolated from Guatteria dielsiana, kinabaline or 6,9-dimethoxy-8-hydroxyonychine (D. Tadic et al., Phytochemistry 26 (1987), 537-541) from Meiogyne virgata, darienine or 8,9-dimethoxy-7-hydroxyonychine and macondine or 6-methoxy-7-hydroxyonychine (A. Cave et al., Phytochemistry 26 (1987), 2093-2098) from Oxandra xylopioides, ursuline or 8-hydroxy-9-methoxyonychine and isoursuline or oxylopine or 9-hydroxy-8-methoxy-onychine (A. Cave et al., Heterocycles 27 (1988), 407-421) from Unonopsis spectabilis, polylongine or 4-methyl-9-hydroxy-8-methoxy-5H-indeno[3,2-b]pyridin-5-ol (Yang Chang Wu, Heterocycles 29 (1989), 463-475) from Polyalthia longifolia, oncodine or 7-methoxy-8-hydroxyonychine (A. Cave et al., J. Natural Prod., 52 (1989), 273-278) from Oncostigma monosperma and polyfothine or 7,8-dimethoxyonychine and isooncodine or 7-hydroxy-8-methoxyonychine (Yang Chang Wu et al., J. Natural Prod., 53 (1990), 1327-1331) from Polyalthia longifolia are also already known.
In the literature mentioned, these alkaloids are ascribed antitumor, antiviral, anticandidal and fungicidal properties. A herbicidal or plant-growth regulating action of these natural substances is not known however.
It is furthermore known that certain indenopyridazines (JO 3161478-A) and indenopyrazoles (GB-A-2 223 946) have herbicidal properties.
As the known natural substances are not always satisfactory in their action, it was the object of the invention to make available novel herbicidal agents having a stronger herbicidal effect and novel plant growth regulators, preferably growth inhibitors. An object of the invention was furthermore novel herbicidal and plant growth-regulating compounds.
We have found that this object is achieved by the novel compounds I defined at the outset.
The invention furthermore relates to herbicidal and bioregulatory, in particular plant growth-inhibiting, compositions,
REFERENCES:
patent: 4873250 (1989-10-01), Hufford
Hufford CD, Liu S, Clark A. (1987) J. Nat. Prod. 50 (5) 961-964.
Arango GJ, Cortes D , Cassels BK, Cave A, Merienne C. (1987) Phytochemistry 26(7) 2093-2098.
Chem. Abst., vol. 57, No. 2, Jul. 23, 1962.
Gerber Matthias
Harreus Albrecht
Kardorff Uwe
Kast Juergen
Koenig Hartmann
BASF - Aktiengesellschaft
Huang Evelyn
Ivy C. Warren
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