Fungicidally active carboxylic acid amides

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...

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514519, 514534, 558414, 558428, 558429, 560 45, 564133, 564142, 564188, A01N 3718, C07C23358

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06090853&

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BRIEF SUMMARY
The present invention relates to carboxamides of the formula I ##STR2## where the substituents have the following meanings: R.sup.1 is C.sub.6 -C.sub.15 -bicycloalkyl, C.sub.6 -C.sub.15 -tricycloalkyl or C.sub.7 -C.sub.15 -bicycloalkenyl, it being possible for these radicals to be partially or fully halogenated and/or, if they are not fully halogenated, to carry one or, independently of one another, two, three, four or five of the following groups: cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and aryl, it being possible for the aryl to be partially or fully halogenated and/or to carry one or, independently of one another, two or three of the following substituents: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and C.sub.1 -C.sub.4 -alkylthio; C.sub.1 -C.sub.8 -alkyl, which may be partially or fully halogenated and/or carry one or two of the following groups: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.5 -C.sub.7 -cycloalkenyl, it being possible for the cyclic groups for their part, to carry one or, independently of one another, two or three halogens, C.sub.1 -C.sub.3 -alkyl groups and/or C.sub.1 -C.sub.3 -alkoxy groups, and aryl, it being possible for the aryl to be partially or fully halogenated and/or to carry one or, independently of one another, two or three of the following substituents: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and C.sub.1 -C.sub.4 -alkylthio or C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkenyl or heterocyclyl, it being possible for these radicals to be partially or fully halogenated and/or to carry one or, independently of one another, two or three of the following groups: cyano, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.1 -C.sub.6 -alkoxy and C.sub.1 -C.sub.6 -alkylthio; or, independently of one another, two or three of the following groups: halogen, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl, aryloxy and hetaryl, it being possible for the rings in these groups, for their part, to carry one or, independently of one another, two or three of the following substituents: halogen, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -alkoxycarbonyl, 2-cyano-N-[1-(1-naphthyl)ethyl]-3-phenylbicydclo[2.2.1]hept-5-ene-2-carbox amide.
The invention additionally relates to a process for preparing the compounds I, to compositions comprising the compounds I and to the use of the compounds I for preparing the compositions.
Furthermore, the invention relates to a process for controlling harmful fungi and to the use of the compounds I for this purpose.
JP-A 02/233 654, EP-A 170 842 and WO-A 95/31432 disclose fungicidal benzylamides. EP-A 653 418 discloses fungicidal amides of bicyclic carboxylic acids.
A paper on asymmetric Diels-Alder reactions also discloses some isomers of 2-cyano-N-[1-(1-naphthyl)ethyl]-3-phenylbicyclo[2.2.1]hept-5-ene-2-carboxa mide (J. Org. Chem. 57 (1992), 4664-4669).
However, the compounds from JP-A 02/233 654, EP 170 842 and WO-A 95/31456 are not yet satisfactory with regard to their fungicidal action.
It is an object of the present invention to provide novel carboxamides with improved action against harmful fungi.
We have found that this object is achieved by the compounds I defined above.
Furthermore, the invention provides a process for preparing the compounds I, compositions comprising the compounds I and the use of the compounds I for preparing the compositions and also a process for controlling harmf

REFERENCES:
patent: 4710518 (1987-12-01), Kurahashi et al.
patent: 5061731 (1991-10-01), Kurahashi et al.
patent: 5534653 (1996-07-01), Wagner et al.
RN 13869-11-9, 1990.
Fugita et al, Chem. Pharm. Bull., 28(2), 453-458, 1980.
Beilstein Reg No. 2013046, 1989.
Beilstein Reg. No. 2757590, 1989.
Beilstein Reg. No. 6059174, 1993.
Beilstein Reg. No. 2853311, 1989.
Beilstein Reg No. 5091636, 1992.
Beilstein Reg. No. 2981433, 1989.
Abstract WO/95/31432, PCT Gazette, Sec.I, 18959, No. 50, 1995.
Abstract, JP 2 233 654, Caplus 1996, p. 12.

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