Patent EP-0723961-A1 (EP)
Inventor: VOGELBACHER UWE JOSEF DR
IPC: A01N43/80
Filed: 1995-12-18
Abstract: Phenyl, pyridyl or naphthyl-substd. 5-fluoropyrimidine derivs. of formula (I) are new. A = substd. phenyl, pyridyl or naphthyl of formula (a) or (b); A<1> -A<4> = CH; or one is N or N<+> -O<-> and the other three are CH; W = O, NR<3>, NOR<3> or =N-NR<4>R<5>; X = O, S or NR<6>; Y, Z = halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylamino or dialkylamino; R<1> = H, alkyl, alkylcarbonyl, alkoxycarbonyl, succinyliminooxy, 5-membered heteroaryl (contg. 1-3N and opt. substd. by 1-4 halogen and/or one or two of alkyl, haloalkyl, alkoxy, halo-alkoxy and alkylthio), OR<7>, -(O)m-NR<8>R<9> or -NHSO2R<10>; R<2> = H, halogen, amino, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylsulphonyl, alkylamino or dialkylamino Äall opt. substd. by one, or for dialkylamino two, of the following: alkoxy, alkylthio, dialkyl-amino, thienyl, furyl, 5-membered heteroaryl (contg. 1-4N or 1-3 N plus one O or S, opt. substd. by 1-3 halogen and/or 1-3 Q), Ar<1>, OAr<1> or 6-membered heteroaryl (contg. 1-3 N, opt. substd. by 1-3 halogen and/or 1-3 Q)Ü; Ar<2>; OAr<2>; SAr<2>; SO2Ar<2>; 5-membered heteroaryl (contg. 1-4 N or 1-3 N plus one O or S, opt. substd. by 1-3 halogen and/or 1-3 of Q, halo-alkoxy and Ar<1> and opt. bonded via O; benzo-fused 5-membered heteroaryl (contg. 1-3 N or one N plus one O or S, opt. substd. by halogen, Q, haloalkoxy or Ar<1> and opt. bonded via O); thienyl or furyl (both opt. substd. by 1-3 halogen and/or 1-3 of Q, haloalkoxy and Ar<1> and opt. bonded via O); benzothienyl or benzofuryl (both opt. substd. by 1-5 halogen and/or 1-3 of Q, haloalkoxy and Ar<1> and opt. bonded via O), 6-membered heteroaryl (contg. 1-4 N, opt. substd. by 1-3 halogen and/or 1-3 of Q, haloalkoxy and Ar<1> and opt. bonded via O); naphthyl, quinolinyl, isoquinolinyl or quinazolinyl (all opt. substd. by 1-3 halogen and/or 1-3 of Q, haloalkoxy and Ar<1> and opt. bonded via O); -C(=W')-R<1>'; or substd. 5-fluoro-2-pyrimidinyloxy of formula (c); Q = NO2, CN, alkyl, alkoxy, alkylthio or haloalkyl; Ar<1> = phenyl opt. substd. by 1-3 halogen and/or 1-3 methyl; W', R<1>' = as W, R<1> respectively; R<3> = H, Ar<2>, or alkyl, alkenyl or alkynyl (all opt. substd by 1-3 of halogen, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, COOH, alkylthio and Ar<2>); R<4> = H, alkyl or phenyl; R<5> = H, Ar<2> or alkyl (opt. substd. by 1-3 of halogen, alkoxy, alkoxycarbonyl, alkylcarbonyl, COOH, alkylthio and Ar<2>); R<6> = H, alkyl, CHO, CONH2 or alkoxycarbonyl; R<7> = H, alkali metal cation, 1 equiv. of alkaline earth metal cation, organic ammonium ion, cycloalkyl (opt. substd. by 1-3 alkyl), alkyl (opt. substd. by 1-5 halogen and/or 1 or 2 or alkoxy, alkylthio, CN, alkylcarbonyl, alkoxycarbonyl, cycloalkyl, -O-N=CR<11>R<12>, phenyl, phenoxy or phenylcarbonyl (where phenyl rings are themselves opt. substd. by 1-5 halogen and/or 1-3 of alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio)); alkyl substd. by 5-membered heteroaryl (contg. 1-3 N and opt. substd. by 1-4 halogen and/or 1 or 2 of alkyl, haloalkyl, alkoxy, haloalkoxy and alkylthio) and opt. further substd. by 1-5 halogen; alkyl substd. in the 2-position by alkoxyimino, alkenyloxyimino, haloalkenyloxy-imino or benzyloxyimino; alkenyl or alkynyl (both opt. substd. by 1-5 halogen); phenyl (opt. substd. by 1-3 of NO2, alkyl and alkoxy and/or by 1-5 halogen); -N=CR<13>R<14>; N-bonded 5-membered heteroaryl (contg. 1-4 N) or N-bonded benzo-fused 5-membered heteroaryl (contg. 1-3 N) opt. substd. by halogen, alkyl or haloalkyl; R<8>, R<9> = H; alkyl, alkenyl or alkynyl (all opt. substd. by 1-5 halogen and/or 1 or 2 of alkoxy, alkylthio, CN, alkyl-carbonyl, alkoxycarbonyl, dialkylamino and cycloalkyl); cycloalkyl (opt. substd. by 1-3 alkyl); Ar<2>; or -CHR<15>-COOR<16>; or R<8>+R<9> = alkylene (opt. interrupted by O, S or N and/or opt. substd. by 1-3 alkyl gps.); R<10> = alkyl or phenyl (opt. substd. by 1-4 of halogen, NO2, CN and alkyl); R<11>, R<12> = alkyl (opt. substd. by alkoxy or alkylthio) or together form alkylene; R<13>, R<14> = alkyl (opt. substd. by phenyl, alkoxy and/or alkylthio), cycloalkyl or phenyl; or together for alkylene (opt. substd. by 1-5 alkyl and opt. bridged by alkylene); R<15> = H or alkyl (opt. substd. by OH, NH2, SH, alkylthio, COOH, CONH2, guanidino, phenyl, hydroxyphenyl, imidazolyl or indolyl); or is bonded to R<9> via alkylene to form a ring; R<16> = alkyl, alkenyl or alkynyl; m = 0 or 1; n = 0-4; Ar<2> = phenyl (opt. substd. by 1-5 halogen and/or by 1-3 of the following : NO2, CN, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, Ar<1>, OAr<1> and OCH2O or OCH2CH2O on adjacent C).