Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
2000-02-10
2000-11-14
Ramsuer, Robert W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5483741, A01N 4356, C07D23114
Patent
active
061471046
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a biphenyl amide of the formula I ##STR2## and salts thereof, where the radicals R.sup.1, R.sup.2 and R.sup.3 have the following meanings:
R.sup.1 is hydrogen or fluorine;
R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, halomethyl, in particular fluoro- or chloromethyl such as, for example, trifluoromethyl, trichloromethyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio;
R.sup.3 is methyl, difluoromethyl or trifluoromethyl.
Additionally, the invention relates to a process for preparing the compounds I, to compositions comprising I and to a method for controlling harmful fungi and to the use of the compounds I, their salts or the compositions for this purpose.
Fungicidal biphenylamides of type I are disclosed in the following publications: U.S. Pat. No. 5,438,070, DE-A 24 17 216, EP-A 545 099 and EP-A 589 301. However, the active compounds mentioned in these publications are not satisfactory with respect to their activity.
It is an object of the present invention to provide biphenylamides having better activity against harmful fungi.
We have found that this object is achieved by the compounds I defined at the outset.
Furthermore, we have found compositions comprising the compounds I or salts thereof and a process for preparing I and the compositions. Moreover, we have found a method for controlling harmful fungi, and the use of the compounds I, their salts or the compositions for this purpose.
The compounds I are obtainable in a manner known per se from the corresponding acyl halides II and the biphenylamines III with the aid of a base such as, for example, triethanolamine. ##STR3##
Hal is halogen, preferably chlorine or bromine;
R.sup.1 is hydrogen or fluorine;
R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, halomethyl, in particular fluoro- or chloromethyl such as, for example, trifluoromethyl, trichloromethyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio;
R.sup.3 is methyl, difluoromethyl or trifluoromethyl.
For the reaction conditions for preparing the compounds I and for the origin of the starting materials II, cf. for example Wo 93/11117, pages 17-19.
The biphenylamines III are generally known or obtainable in a manner known per se (cf. for example Tetrahedron Letters 28 (1987), 5093-5096).
The salts of the acid-stable compounds I which contain basic centers, especially basic nitrogen atoms, and in particular with salts of mineral acids such as sulfuric acid and phosphoric acid or Lewis acids such as zinc chloride also form part of the subject matter of the present invention. Generally, the kind of salt does not matter. For the purposes of the invention, preference is given to those salts which do not damage the plants, areas, materials or spaces to be kept free from harmful fungi and which do not adversely affect the activity of the compounds I. Particularly important are salts of this kind which are suitable for agricultural purposes.
The salts of the compounds I are obtainable in a manner known per se, especially by reacting the corresponding biphenylamides I with the abovementioned acids in water or an inert organic solvent at temperatures from -80 to 120.degree. C., preferably from 0 to 60.degree. C.
In the definitions of the compounds I to III given at the outset, collective terms were used which are representative of the following substituents:
halogen: fluorine, chlorine, bromine and iodine;
alkyl: straight-chain or branched alkyl groups having 1 to 4 carbon atoms, for example C.sub.1 -C.sub.4 -alkyl such as methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl;
alkoxy: straight-chain or branched alkoxy groups having 1 to 4 carbon atoms, for example C.sub.1 -C.sub.3 -alkoxy such as methyloxy, ethyloxy, propyloxy and 1-methylethyloxy;
alkylthio: straight-chain or branched alkyl groups having 1 to 4 carbon atoms (as mentioned above) which are linked to the skeleton via a sulfur atom (--S--), for example methylthio, ethylthio, propylthio, 1-m
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Elbe et al, Chem Abstracts, vol. 132, No. 180571, abstract of WO 2000014071, 2000.
Patent Abst. JP, vol. 12, No. 263 Abst. JP. 97/034280/03 (1997).
Ammermann Eberhard
Eicken Karl
Lorenz Gisela
Rack Michael
Strathmann Siegfried
BASF - Aktiengesellschaft
Ramsuer Robert W.
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