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Pub. No.:    WO/1994/001432    International Application No.:    PCT/EP1993/001682
Publication Date: 20.01.1994 International Filing Date: 30.06.1993
A01N 43/78 (2006.01), C07D 417/12 (2006.01), C07D 513/04 (2006.01)
Applicants: CIBA-GEIGY AG [CH/CH]; Klybeckstrasse 141, CH-4002 Basle (CH) (For All Designated States Except US).
HILDENBRAND, Christof [CH/CH]; (CH) (For US Only).
GEHRET, Jean-Claude [CH/CH]; (CH) (For US Only).
TINEMBART, Olivier [CH/CH]; (CH) (For US Only)
Inventors: HILDENBRAND, Christof; (CH).
GEHRET, Jean-Claude; (CH).
TINEMBART, Olivier; (CH)
CIBA-GEIGY AG; Patentabteilung, Klybeckstrasse 141, CH-4002 Basel (CH)
Priority Data:
2219/92-5 13.07.1992 CH
Abstract: front page image
(EN)Novel 4,5-dicyanoimidazole derivatives of formula (I), wherein X is oxygen, sulfur, SO or SO¿2?; R¿1? is hydrogen, C¿1?-C¿6?alkyl, C¿1-?-C¿6?haloalkyl, C¿1?-C¿6?hydroxyalkyl, C¿1?-C¿6?cyanoalkyl, or a C¿1?-C¿6?alkylene substituted by C¿1?-C¿6?alkoxy, C¿1?-C¿6?haloalkoxy, C¿1?-C¿6?alkylthio, C¿1?-C¿6?haloalkylthio, C¿1?-C¿6?alkylsulfinyl, C¿1?-C¿6?haloalkylsulfinyl, C¿1?-C¿6?alkylsulfonyl, C¿1?-C¿6?haloalkylsulfonyl, C¿1?-C¿6?hydroxyalkyl, C¿1?-C¿6?alkyloxycarbonyl, C¿1?-C¿6?alkylcarbonyl, C¿1?-C¿6?alkylcarbonyloxy or by COOH; R¿2? is hydrogen, halogen, CN, C¿1?-C¿6?alkyl, C¿1?-C¿6?haloalkyl, C¿1?-C¿6?cyanoalkyl, C¿1?-C¿6?hydroxyalkyl, C¿1?-C¿6?alkoxy, C¿1?-C¿6?haloalkoxy, C¿1?-C¿6?alkylthio, C¿1?-C¿6?haloalkylthio or C¿3?-C¿7?cycloalkyl; R¿3? is hydrogen, halogen, C¿1?-C¿6?alkyl, C¿1?-C¿6?haloalkyl, cyano or nitro; R¿4? is hydrogen, halogen, nitro, cyano, NCS, C¿1?-C¿6?alkyl, C¿1?-C¿6?haloalkyl, C¿1?-C¿6?alkoxy or C¿1?-C¿6?haloalkoxy; and R¿5? is hydrogen, halogen, nitro, C¿1?-C¿6?alkyl, C¿1?-C¿6?haloalkyl, C¿1?-C¿6?alkoxy or C¿1?-C¿6?haloalkoxy; or R¿4? and R¿5? together form a -O-(CH¿2?)¿m?-O- bridge, wherein m is an integer selected from the group consisting of 1, 2 and 3, with the proviso that R¿4? and R¿5? are located at adjacent carbon atoms; including the physiologically tolerable addition compounds, can be used against insects and representatives of the order Acarina that are harmful to animals and plants, as well as against helminths in warm-blooded animals.
(FR)L'invention concerne de nouveaux dérivés de la 4,4-dicyanoimidazole de la formule (I). Dans cette formule X représente oxygène, soufre, SO ou SO¿2?; R¿1? représente hydrogène, C¿1?-C¿6?alkyle, C¿1-?-C¿6?haloalkyle, C¿1?-C¿6?hydroxyalkyle, C¿1?-C¿6?cyanoalkyle, ou C¿1?-C¿6?alkylène avec comme substituant un C¿1?-C¿6?alcoxy, C¿1?-C¿6?haloalcoxy, C¿1?-C¿6?alkylthio, C¿1?-C¿6?-haloalkylthio, C¿1?-C¿6?alkylsulfinyle, C¿1?-C¿6?haloalkylsulfinyle, C¿1?-C¿6?alkylsulfonyle, C¿1?-C¿6?haloalkylsulfonyle, C¿1?-C¿6?hydroxyalkyle, C¿1?-C¿6?alkyloxycarbonyle, C¿1?-C¿6?alkylcarbonyle, C¿1?-C¿6?alkylcarbonyloxy ou COOH; R¿2? représente hydrogène, halogène, CN, C¿1?-C¿6?alkyle, C¿1?-C¿6?haloalkyle, C¿1?-C¿6?cyanoalkyle, C¿1?-C¿6?-hydroxyalkyle, C¿1?-C¿6?alcoxy, C¿1?-C¿6?haloalcoxy, C¿1?-C¿6?alkylthio, C¿1?-C¿6?haloalkylthio ou C¿3?-C¿7?cycloalkyle; R¿3? est un hydrogène, halogène, C¿1?-C¿6?alkyle, C¿1?-C¿6?haloalkyle, cyano ou nitro; R¿4? est hydrogène, halogène, nitro, cyano, NCS, C¿1?-C¿6?alkyle, C¿1?-C¿6?haloalkyle, C¿1?-C¿6?alcoxy ou C¿1?-C¿6?haloalcoxy; et R¿5? représente hydrogène, halogène, nitro, C¿1?-C¿6?alkyle, C¿1?-C¿6?haloalkyle, C¿1?-C¿6?alcoxy ou C¿1?-C¿6?haloalcoxy, ou R¿4? et R¿5? forment ensemble un pont -O-(CH¿2?)¿m?-O- où m représente un nombre entier choisi parmi 1, 2 et 3, une condition à satisfaire étant alors que R¿4? et R¿5? doivent être liés à des atomes de carbone adjacents. L'invention concerne également les composés d'addition de ces dérivés acceptables sur le plan physiologique. On peut utiliser ces dérivés et composés d'addition contre les insectes appartenant à l'ordre des acariens qui sont nuisibles pour les animaux et les plantes et contre les helminthes chez les animaux à sang chaud.
Designated States: AU, BB, BG, BR, BY, CA, CZ, FI, HU, JP, KP, KR, KZ, LK, MG, MN, MW, NO, NZ, PL, RO, RU, SD, SK, UA, US, VN.
European Patent Office (AT, BE, CH, DE, DK, ES, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, ML, MR, NE, SN, TD, TG).
Publication Language: English (EN)
Filing Language: English (EN)