2-amino-4-oxo-4H-benzopyrans, their preparataion and their use a

Details 2-amino-4-oxo-4H-benzopyrans, their preparataion and their use a 2-amino-4-oxo-4H-benzopyrans, their preparataion and their use a

1993-06-07

1995-05-30

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549402, C07D31122

Patent

active

054203074

DESCRIPTION:

BRIEF SUMMARY
This application is a 317 of PCT/EP91/02268, filed Nov. 29, 1991.
The present invention relates to 2-amino-4-oxo-4H-benzopyrans of the general formula I. ##STR2## where R.sup.1 is hydrogen, hydroxyl, halogen, nitro, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkyl-thio or a group --NR.sup.5 R.sup.6, or --SO.sub.2 --R.sup.8, -C.sub.8 -cycloalkyl, phenyl-C.sub.1 -C.sub.3 -alkyl, amino, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, phenyl or phenylamino where the phenyl radicals are each unsubstituted or carry from one to three of the groups stated for R.sup.1, three of the groups stated for R.sup.1, --CS--R.sup.9 or --SO.sub.2 R.sup.10, R.sup.3, together with the nitrogen atom to which they are bonded, form a 3-membered to 8-membered saturated or unsaturated ring which, if desired, may in turn furthermore carry from one to three C.sub.1 -C.sub.4 -alkyl radicals, or a group .dbd.CR.sup.2 R.sup.11, -alkoxy, C.sub.3 -C.sub.8 -cycloalkyl, or benzyl or is phenyl which is unsubstituted or carries from one to three of the groups stated for R.sup.1, or is --O--CO--R.sup.12 or --O--CS--R.sup.12, -C.sub.8 -cycloalkyl, phenyl or phenyl-C.sub.1 -C.sub.3 -alkyl, where the phenyl radicals may each be unsubstituted or may carry from one to three of the radicals stated for R.sup.1, --CH.dbd.N--R.sup.14, amino, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, hydrazino, C.sub.1 -C.sub.6 -alkylhydrazino or phenylhydrazino, where the phenyl radical is unsubstituted or substituted by from one to three of the groups stated for R.sup.1 and that R.sup.4 is not cyano, a group CONH.sub.2 or formyl when R.sup.2 and R.sup.3 are each hydrogen and R.sup.1 is simultaneously hydrogen, chlorine, bromine, methyl, methoxy, phenyl, nitro or dimethylamino and m is 1, and furthermore with the proviso that R.sup.4 is not a group --CH.dbd.N--OH when R.sup.1, R.sup.2 and R.sup.3 are simultaneously hydrogen.
The present invention furthermore relates to processes for the preparation of the compounds I and to herbicides which contain. derivatives and/or 2-amino-4-oxo-4H-benzopyrans I', where I' has the meanings of I without the proviso, as antidotes, and to methods for selectively controlling undesirable plant growth with these herbicides.
The novel compounds I are obtainable by various methods. 2-Amino-4-oxo-4H-benzopyrans are obtained, for example, by formylating unsubstituted or substituted o-hydroxyacetophenones with phosphoryl chloride and dimethylformamide (H. Harnisch, Liebigs Ann. Chem. 765 (1972), 8; A. Nohara et al., Tetrahedron Lett. 1973, 1995), converting the aldehyde to the oxime and subjecting the latter to an-alkali-catalyzed rearrangement reaction (U. Petersen et al., Liebigs Ann. Chem. 1976, 1659). Another method comprises reacting o-acetoxybenzoyl chlorides with malonodinitrile (G. P. Ellis, J. Chem. Soc. Perkin Trans. I, 1986, 1643). The prior art does not describe a crop-protecting effect of 2-amino-4-oxo-benzopyrans.
It is an object of the present invention to provide compounds which reduce the disadvantages encountered when the abovementioned herbicides of the formulae VIII and IX are used, at least to such an extent that the herbicides are tolerated by the crops from the family comprising the grasses.
We have found that this object is achieved by the 2-amino-4-oxo-4H-benzopyrans I defined at the outset. We have furthermore found processes for the preparation of these compounds I and methods for the joint use of these compounds with the herbicides VIII and IX for influencing undesirable plant growth. The present invention furthermore relates to agents which contain the compounds I', it being unimportant whether the herbicidal active ingredient and the antidote compound are formulated and applied together or separately and, in the case of separate application, the order in which the herbicidal active ingredient and the antidote are applied being irrelevant.
The novel compounds I are obtainable by a plurality of met

REFERENCES:
patent: 3932466 (1976-01-01), Brown et al.
patent: 4143042 (1979-03-01), Nohara et al.
patent: 4255576 (1981-03-01), Nohara et al.
patent: 4299963 (1981-11-01), Nohara et al.
patent: 4505738 (1985-03-01), Gsell
patent: 5059240 (1991-10-01), Hagen et al.
A. Nohara et al, Tetrahedron Lett. (1973), 1995-1998.
P. S. Bevan et al., J. Chem. Soc. Perkin Trans. I (1986), pp. 1643-1649.
A. Nohara et al., J. Med. Chem. 28 (1985), pp. 559-568.
Akira Nohara et al., J. Pesticide Sci. 15 (1990) 241-244.
Chemical Abstracts, vol. 108, No. 21, May 23, 1988' abstract No. 186576U, p. 689 Corresponds to JP 62/228,001, (1987).
Chemical Abstracts, vol. 90, No. 7, Feb. 12, 1979; Abst. No. 54827B, p. 599 Corresponds to JP 53/111,071 (1978).
A. Balbi et al., Il Pharmaco 44 (1989), pp. 565-577.
F. Eiden et al., Archiv der Pharmazie 316 (1983), pp. 34-42.
C. K. Ghosh et al., Indian Journal of Chemistry 24B (1985), pp. 914-917.

Affiliated with

Also associated with

Rating

2-amino-4-oxo-4H-benzopyrans, their preparataion and their use a does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 2-amino-4-oxo-4H-benzopyrans, their preparataion and their use a, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 2-amino-4-oxo-4H-benzopyrans, their preparataion and their use a will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-363397