Patent EP-0075167-B1 (EP)
IPC: C07D231/12
Filed: 1982-09-06
Granted: 1985-02-13
Abstract: 1. N-(1-Alkenyl)-carboxanilides of the general formula (I)  see diagramm : EP0075167,P39,F1  in which R**1 represents hydrogen or alkyl, R**2 represents hydrogen, alkyl, alkoxy, alkoxyalkyl, hydroxyalkyl or benzyl, R**3 represents hydrogen, alkyl, alkenyl, alkoxy, alkoxyalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonyl or alkoxycarbonylalkyl, or R**1 and R**2 , together with the C=C double bond, represent a mono- or polyunsaturated ring which is optionally mono- or polysubstituted by alkyl with 1 to 4 carbon atoms, halogen or hydroxyl, and which can also contain hetero atoms, or R**2 and R**3 , together with the adjacent carbon atom, represent a saturated or unsaturated ring which is optionally mono- or polysubstituted by alkyl with 1 to 4 carbon atoms, halogen or hydroxyl, and which can also contain hetero atoms, X**1 , X**2 and X**3 independently of one another represent hydrogen, alkyl or halogen, Y represents furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl ; phenyl which is optionally substituted by halogen, alkyl, alkoxy or alkylthio with in each case 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy or halogenoalkylthio with in each case 1 to 4 carbon and 1 to 5 identical or different halogen atoms, nitro, cyano or phenyl which is optionally substituted by halogen or alkyl with 1 to 4 carbon atoms ; isoxazolyl optionally substituted by alkyl ; 1,2,4-triazol-1-yl, imidazol-1-yl or pyrazol-1-yl, or alkyl, alkenyl or alkinyl which are optionally substituted by cyano or thiocyano ; cycloalkyl or cycloalkenyl which are optionally substituted by alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, halogenoalkyl with 1 to 4 carbon and up to 5 identical or different halogen atoms, halogenoalkenyl with 2 to 4 carbon and up to 5 identical or different halogen atoms, halogen, alkoxy with 1 to 4 carbon atoms or a two-to five-membered methylene bridge dihalogenoalkyl ; or the groupings : -CH2 Az   -CH2 R**9 -CH2 OR**8 -CH2 OR**9   -CH2 SR**8   -CH2 SR**9 -CH2 -SOn R**8   -CH2 SOn -R**9 -CH2 OSOR**8   -CH2 OSOR**9   -CH2 OSO2 R**8 -CH2 OSO2 R**9 -CH2 OCOR**8 -CH2 OCOR**9   -OR**8   -OR**9   -SR**8 -SR**9   -NR**10 R**11 or  see diagramm : EP0075167,P39,F2  wherein R**8 represents optionally halogen-, cyano- or thiocyanosubstituted alkyl, alkenyl, alkinyl or alkoxyalkyl, R**9 represents phenyl which is optionally substituted by halogen, alkyl, alkoxy or alkylthio with in each case 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy or halogenoalkylthio with in each case 1 to 4 carbon and 1 to 5 identical or different halogen atoms, nitro, cyano, or phenyl which is optionally substituted by halogen or alkyl with 1 to 4 carbon atoms, R**10 and R**11 are identical or different and represent hydrogen, alkyl, alkenyl or phenyl which is optionally substituted by halogen, alkyl, alkoxy or alkylthio with in each case 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy or halogenoalkylthio with in each case 1 to 4 carbon and 1 to 5 identical or different halogen atoms, nitro, cyano, or phenyl which is optionally substituted by halogen or alkyl with 1 to 4 carbon atoms, Az represents pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl- n represents 1 or 2, and, when Y represents Az or -CH2 -Az, the physiologically tolerated acid addition salts and metal salt complexes thereof.