Patent EP-1120411-A2 (EP)
Inventor: LINKER KARL-HEINZ
IPC: A01N43/653
Filed: 1995-12-04
Abstract: 3-Aryl-1,2,4-triazoles (Ia), (Ib) and (Ic) are new; Q1,Q2= O or S; R1, R2 = H; CN; CHO; alkyl opt. substd. by halo, CN, COOH, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkoxycarbonyl, alkenyloxycarbonyl or alkynyloxycarbonyl; alkenyl, alkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl or alkynyloxycarbonyl all opt. substd. by halo; or cycloalkyl or cycloalkylcarbonyl both opt. substd. by halo, CN or COOH; but R1 and R2 are not both H; Ar = gp. of formula (i); R3,R4,R7 = H or halo; R5 = CN; COOH; COCl; CONH2; CSNH2; OH; halo; or alkyl, alkoxy or alkoxycarbonyl opt. substd. by halo; and R6 = -A1-A2-A3; or 2 adjacent gps. R3-R7 = -Q3-CQ4-; -Q3-CQ4-Q5-; -Q3-C(R8R9)-Q5-; -C(R8R9)-CQ4-; -C(R8R9)-Q3-CQ4-; -Q3-C(R8R9)-C(R8R9)-; -Q3-C(R8R9)-C(R8R9)-Q5-; -C(R8R9)-C(R8R9)-CQ4-; -Q3-C(R8)=C(R8)-; -C(R8)=C(R8)-CQ4-; -Q3-C(R8R9)-CQ4-; -N(R10)-C(R8R9)-CQ4-; -C(R8)=N-; -Q3-CQ4-C(R8R9)-; -Q3-CQ4-N(R10)-; -Q3-C(R8R9)-CQ4-N(R10)-; -C(R8R9)-Q3-CQ4-N(R10)-; -C(R8R9)-C(R8R9)-N(R10)-; -C(R8R9)-C(R8R9)-CQ4-N(R10)-; -C(R8)=C(R8)-N(R10)-; -C(R8)=C(R8)-CQ4-N(R10)-; -C(R8R9)-CQ4-N(R10)-, -N(R10)-C(R8R9)-CQ4-N(R10)-; -C(R8)=N-N(R10)-; -Q3-CQ4-C(R8R9)-N(R10)-; or -Q3-(CR8R9)-C(R8R9)-CQ4-N(R10)-; A1 = single bond; O; S; SO; SO2, CO; N(A4); or alkanediyl; alkenediyl, azaalkenediyl, alkynediyl, cycloalkanediyl, cycloalkenediyl or phenylene opt. substd. by halo; A4 = H; OH; alkyl, alkenyl; alkynyl; alkoxy; aryl; alkylcarbonyl; arylcarbonyl; alkylsulphonyl; or arylsulphonyl; A2 = A1 except NR4 when R4 = alkenyl, alkynyl, alkylcarbonyl or arylcarbonyl; A3 = H (except when A1 and/or A2 = single bond); OH; SH; NH2; CN; NC; SCN; NO2; COOH; CONH2; CSNH2; sulpho; SO2Cl; halo; alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, mono- or di-alkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl all opt. substd. by halo or alkoxy; alkenyl, alkenyloxy, alkenylthio, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylthio, alkynylamino or alkynyloxycarbonyl opt. substd. by halo; cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkyl-alkoxycarbonyl opt. substd. by halo, CN, COOH, alkyl and/or alkoxycarbonyl; aryl, aryloxy, aralkyl, aralkoxy, aryloxycarbonyl or aralkoxycarbonyl opt. substd. by NO2, CN, COOH, halo, alkyl, haloalkyl, alkoxy, haloalkoxy and/or alkoxycarbonyl; or partly or fully hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylalkyl, furylalkyl, thienylalkyl, oxazolylalkyl, isoxazolylalkyl, thiazolylalkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy, furylalkoxy, perhydropyranyloxy or pyridylalkoxy; Q3,Q4,Q5 = O or S; R8,R9 = H; halo; or alkyl; or R8+R9 = alkanediyl; R10 = H; OH; alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl opt. substd. by CN, halo, alkoxy, alkylcarbonyl or alkoxycarbonyl; alkenyl, alkynyl, alkoxy or alkenyloxy opt. substd. by halo; cycloalkyl or cycloalkylalkyl opt. substd. by halo or alkyl; or aralkyl or aralkoxy opt. substd. by CN, halo, alkyl, haloalkyl, alkoxy or haloalkoxy; cpds. (Ia) are excluded when Q1 = O, Q2 = S, R1 = R2 = Me and Ar = 3,4-dichlorophenyl or 4-chloro-3-trifluoromethylphenyl.