Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-02-17
1999-12-07
Fan, Jane
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514365, 514403, 546316, 548200, 5483741, C07D21382, A61K 3144
Patent
active
059984503
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to biphenylamides of the general formula I ##STR3## and to their salts where the radicals R.sup.1, R.sup.2 and A have the following meanings: C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio; ##STR4## where the substituents R.sup.3, R.sup.4, R.sup.5 and R.sup.6, in turn, have the following meanings:
Furthermore, the invention relates to a process for the preparation of the compounds I, to compositions comprising I, to a method of controlling harmful fungi, and to the use of the compounds I, of their salts or of the compositions for this purpose.
Fungicidal biphenylamides of the type I are disclosed in the following publications: DE-A 24 17 216, EP-A 545 099 and EP-A 589 301. However, the active ingredients mentioned in these publications are not yet satisfactory with a view to their activity.
It was therefore an object of the present invention to provide biphenylamides which have an improved activity against harmful fungi.
We have found that this object is achieved by the compounds I defined at the outset.
We have furthermore found compositions which comprise the compounds I or salts thereof and a process for the preparation of I and of the compositions. We have also found a method of controlling harmful fungi and the use of the compounds I, of their salts or of the compositions for this purpose.
The compounds I can be obtained in a manner known per se from the corresponding carboxylic acid halides II and the biphenylamines III with the aid of a base. ##STR5## Hal is halogen, preferably chlorine or bromine; R.sup.1 is fluorine; C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio; ##STR6## where the substituents R.sup.3, R.sup.4, R.sup.5 and R.sup.6, in turn, have the following meanings:
As regards the reaction conditions for the preparation of the compounds I and the origin of the starting compounds II, compare, for example, EP-A 589 301 and EP-A 545 099.
Those biphenylamines III which are not generally known can be obtained in a manner known per se (compare, for example, Tetrahedron Letters 28, page 5093 to page 5096, 1987).
The invention also encompasses the salts of the acid-resistant compounds I which contain basic centers, especially basic nitrogen atoms, in particular with mineral acids, such as sulfuric acid and phosphoric acid or Lewis acids, such as zinc chloride. Normally, the type of salt is immaterial. Salts which are preferred for the purpose of the invention are those which do not damage the plants, areas, materials or spaces to be kept from harmful fungi and which do not adversely affect the activity of the compounds I. Such salts which are suitable for agricultural purposes are especially important.
The salts of the compounds I are accessible in a manner known per se, mainly by reacting the corresponding biphenylamides I with the abovementioned acids in water or an inert organic solvent at from -80 to 120.degree. C., preferably 0 to 60.degree. C.
In the definition of the compounds I given at the outset, collective terms are used which represent the following substituents: eg. C.sub.1 -C.sub.6 -alkyl, such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl; atoms, eg. C.sub.1 -C.sub.3 -alkoxy, such as methyloxy, ethyloxy, propyloxy and 1-methylethyloxy; atoms (as mentioned above) which are bonded to the skeleton via a sulfur atom (--S--), eg. C.sub.1 -C.sub.4 -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, n-butylthio and tert-butylthio.
Preferred compounds I with a view to their biological activity against harmful fungi are those where R.sup
REFERENCES:
patent: 4001416 (1977-01-01), Pommer et al.
patent: 4214090 (1980-07-01), Huppatz
patent: 5330995 (1994-07-01), Eicken et al.
patent: 5438070 (1995-08-01), Eicken et al.
patent: 5480897 (1996-01-01), Eicken et al.
patent: 5556988 (1996-09-01), Eicken et al.
patent: 5589493 (1996-12-01), Eicken et al.
Synthetic Connections to the Aromatic Directed . . . Sharp et al. 5093-5096.
Chem Abst. JP 07145156-A 1993.
Chem. Abst. vol. 123, 1994 p. 1246.
Ammermann Eberhard
Eicken Karl
Gotz Norbert
Harreus Albrecht
Lorenz Gisela
BASF - Aktiengesellschaft
Fan Jane
LandOfFree
Heterocyclically substituted biphenylamine derivatives, their pr does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Heterocyclically substituted biphenylamine derivatives, their pr, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Heterocyclically substituted biphenylamine derivatives, their pr will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-824365