Patent DE-10007286-A1 (DE)
Title: New phenyl-substituted heterocyclic enaminone and enaminethione derivatives useful as herbicides and pesticides, especially insecticides, acaricides, nematocides and fungicides
Inventor: FISCHER REINER
IPC: A01N43/84
Filed: 2000-02-17
Abstract: Phenyl-substituted heterocyclic enaminone and enaminethione derivatives are new. They are prepared using partly new intermediates. The phenyl-substituted heterocyclic enaminone and enaminethione derivatives are compounds of formula (I). [Image] Q1O or S; X : CN; CONR1>R2>; or CSNH2; Y : halo; alkyl, cycloalkyl, cycloalkoxy, alkoxy, phenyl, phenoxy, phenylalkyl, heteroaryl or heteroarylalkyl (each optionally substituted), CN, CO2R1> or CONR1>R2>, or 2 adjacent Y form a (saturated) ring optionally substituted with 1 or more heteroatoms; A : CH2, O, S, SO2, N, N(B) or C(O); B : H, CN, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, phenoxyalkyl, phenylalkoxyalkyl, phenylthioalkyl, phenylalkylthioalkyl, phenyl, phenylalkyl, heteroaryl or heteroaryl-alkyl (each optionally substituted), CO2>R1>, CONR1>R2>, SO2R1>, COR1>, -(C)l(R5>)(R6>)-C(R3>)(R4>)-CO2R1>, -(C)l(R5>)(R6>)-C(R3>)(R4>)-CONR1>R2> or -(C)l(R5>)(R6>)-C(R3>)(R4>)-COR1>; l : 0-3; m : 0-1; q : 0 or 1; n : 0-5; R1>H, (saturated) alkyl or cycloalkyl (each optionally substituted and each optionally interrupted with 1 or more hetero atoms), phenyl, heteroaryl, phenylalkyl or heteroarylalkyl (each optionally substituted); R2>H, (saturated) alkyl or alkoxy, phenyl, phenylalkyl or phenylalkoxy (each optionally substituted); or NR1>R2> forms a ring (optionally substituted and optionally interrupted with 1 or more hetero atoms); R3>H or (substituted) alkyl, alkoxy, phenyl or phenylalkyl; R4-6> each : H or (substituted) alkyl; R7>H or halo; R8>CN, CO2H, -C(Q1)-NR1>R2>, halo, alkyl, alkylthio, alkenyl, alkynyl, alkoxy, alkoxyalkyl or alkylthioalkyl (each optionally substituted); R9>A1-A2-A3; A1, A2 each : single bond, O, SO, SO2, CO, -N-A4-, alkanediyl, alkenediyl, azaalkenediyl, alkynediyl, cycloalkanediyl, cycloalkenediyl or phenylene (each optionally substituted with halo); A3H (except when A1 and/or A2 = single bond), OH, NH2, isocyano, thiocyanato, NO2, CO2H, CONH2, CSNH2, sulfo, chlorosulfonyl, halo, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, NH(alkyl), N(alkyl)2, alkoxycarbonyl, dialkoxy(thio)phosphoryl (each optionally substituted with halo or alkoxy), aryl, aryloxy, aralkyl, aralkoxy, aryloxycarbonyl or aralkoxycarbonyl (each optionally substituted with NO2, CN, CO2H, halo, alkyl, haloalkyl, alkoxy, haloalkoxy and/or alkoxycarbonyl), pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, dioxolonyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, alkyl substituted with pyrazolyl, imidazolyl (each optionally partly or fully hydrogenated, optionally substituted and optionally bonded via alkyl (except pyrrolyl) or alkoxy); A4H, OH, alkyl, alkenyl, alkynyl, alkoxy, aryl, alkylsulfonyl or arylsulfonyl; R10>H or R9> + R10> form a saturated or unsaturated ring (optionally substituted and optionally interrupted with one or more hetero atoms). Compounds are excluded when (i) A1 = A2 = S, SO or SO2 and (ii) A3 = halo and A1 = A2 = single bond; and (iii) A = CH2 and n = 0. Independent claims are also included for: (A) the preparation of compounds (I); (B) 2-fluoro-4-bromo-5-nitrobenzoic acid; (C) 2,4-difluorophenyl carbonate; (D) 2,4-difluoro-5-bromophenol; and (E) intermediates of formula (XX), (XXII), (XXIII), (XXIIIa), (XIVa), (XIVb) and (IIb). [Image] R7>, R8>F or Cl; R10>H; R14>H, 1-4C alkyl, 1-6C alkenyl, 1-6C alkynyl or optionally substituted benzyl; R15>H or CH3; L : 2-F-4-CN-5-OH, 2-F-4-Cl-5-(O-allyl), 2-F-4-Cl-5-OEt, 2-F-4-CN-5-isopropylthio, 2-F-4-CN-5-benzyloxy, 4-CN-5-NO2 or 2-F-4-CN-5-NO2. - ACTIVITY : Herbicidal; insecticidal; acaricidal; nematocidal; microbicidal; antimycotic. - MECHANISM OF ACTION : None given.