Patent DE-102004010086-A1 (DE)
Title: New 4-(alpha-aminobenzhydryl)-1-benzyl-piperidine derivatives, useful as pesticides, e.g. insecticides, acaricides, nematocides or endo- or ectoparasiticides
Inventor: JEANGUENAT ANDRE
IPC: A01N53/00
Filed: 2004-03-02
Abstract: 4-(alpha -Aminobenzhydryl)-1-benzyl-piperidine or -1,2,3,6-tetrahydropyridine derivatives (I) are new. Piperidine derivatives of formula (I) (including E/Z-isomers and their mixtures and/or tautomers) and their salts are new. [Image] R1, R2H, Cl, Br, I, 1-12C alkyl, cycloalkyl, haloalkyl, halocycloalkyl, Q, alkoxy, haloalkoxy, alkenyloxy, alkynyloxy, haloalkenyloxy, haloalkynyloxy, SF5, CON(R11)2, OCON(R11)2, CN, NO2, SO2N(R11)2, S(O)p-alkyl, S(O)p-haloalkyl, OS(O)p-alkyl or OS(O)p-haloalkyl; Q : 2-4C alkenyl, 2-4C alkynyl, 2-4C haloalkenyl or 2-4C haloalkynyl; R3, R4H; or together form a bond; R5H, alkyl, haloalkyl, cycloalkyl, 2-4C alkenyl, 2-4C alkynyl, alkoxy, alkoxyalkyl, haloalkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylsulfinyl or alkylsulfonyl; R55H, alkyl, haloalkyl, cycloalkyl, 2-4C alkenyl, 2-4C alkynyl, alkoxy, alkoxyalkyl, haloalkoxy, alkenyloxy or alkynyloxy; R6H, halo, CN, NO2, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkoxy, alkoxy, haloalkoxy, Q, alkenyloxy, alkynyloxy, haloalkenyloxy, haloalkynyloxy, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, N(R11)2, CON(R11)2, OCON(R11)2, SO2N(R11)2, S(O)p-alkyl, S(O)p-haloalkyl, OS(O)p-alkyl, OS(O)p-haloalkyl, N(R16)-C(Y)-ZR7 or C(R13)=N=W-R14; or aryl, benzyl, aryloxy, benzyloxy, heterocyclyl or heterocyclyloxy (all optionally substituted (os) by 1-5 of halo, CN, NO2, alkyl, 3-8C cycloalkyl, (3-8C) cycloalkylalkyl, haloalkyl, alkoxy, cycloalkoxy, (3-8C) cycloalkoxyalkyl, (3-8C) cycloalkylalkoxy, haloalkoxy, Q, alkenyloxy, alkynyloxy, haloalkenyloxy, haloalkynyloxy, phenyl, benzyl, phenoxy, benzyloxy, heterocyclyl or heterocyclyloxy); R7H, 1-12C alkyl, 3-8C cycloalkyl, haloalkyl, halocycloalkyl, Q COR8, OR9, NHR9, N=R(R1-0)2, phenyl or benzyl; R8H, 1-12C alkyl, 3-8C cycloalkyl, haloalkyl, halocycloalkyl, Q, OR9 or NHR9; R9, R10alkyl, haloalkyl, halocycloalkyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, 3-8C cycloalkyl, phenyl or benzyl; R11H, 1-12C alkyl, 1-12C haloalkyl, 2-12C alkenyl, 2-12C alkynyl, 2-12C haloalkenyl, 2-12C haloalkynyl, CONR14R15, CSNR14R15 or S(O)p-R14; or 3-8C cycloalkyl, aryl, arylalkyl, aryloxy, heterocyclyl or heterocyclylalkyl (all os in the ring by 1-5 of halo, OH, CN, NO2, alkyl, haloalkyl, alkoxy or haloalkoxy); or N(R11)2os heterocycle; R12H, alkyl or benzyl; R13halo, alkyl, 3-8C cycloalkyl, (3-8C) cycloalkylalkyl, haloalkyl, alkoxy, 3-8C cycloalkoxy, 3-8C cycloalkoxyalkyl, haloalkoxy or mono- or dialkylamino; R14, R15H, alkyl, 3-8C cycloalkyl, (3-8C) cycloalkylalkyl, haloalkyl, Q or alkylcarbonyl; R16H, alkyl, alkoxyalkyl, cycloalkyl, haloalkyl, alkenyl or alkynyl; R17H, alkyl, haloalkyl, alkoxyalkyl, 3-8C cycloalkyl, 3-8C halocycloalkyl, alkenyl, alkynyl, haloalkenyl or haloalkynyl; or aryl, arylalkyl, arylalkyl or heterocyclyl (all os by 1-3 of halo, CN, NO2, alkyl, 3-8C cycloalkyl, haloalkyl, alkoxy, haloalkoxy, Q, alkenyloxy or alkynyloxy); m, n, s : 1-5; o : 1-3; p : 0-2; q : 0 or 1; Y : O or S; Z : direct bond, O, S or NR18; R18H, alkyl, alkoxyalkyl, 3-8C cycloalkyl, haloalkyl, alkenyl or alkynyl; W : O, NH or N(alkyl); unless specified otherwise alkyl moieties have 1-6C, alkenyl or alkynyl moieties 2-6C and cycloalkyl moieties 3-6C. ACTIVITY : Insecticide; acaricide; nematocide; anthelmintic; antiparasitic. In tests against Heliothis virescens caterpillars on soya plants, C-(1-(4-(2-ethyl-2H-tetrazol-5-yl)-benzyl)-1-oxy-piperidin-4-yl)-C,C-bis-(4-trifluoromethyl-phenyl)-methylamine (Ia) at a concentration of 50 ppm gave a degree of protection of more than 80%. MECHANISM OF ACTION : None given in the source material.