Patent DE-10224119-A1 (DE)
Title: Insecticides, especially for use in protection of plants or materials such as wood, comprising N,N'-disubstituted p-phenylene diamine derivatives, also having acaricidal, nematocidal and antifouling action
Inventor: SCHLITZER MARTIN
IPC: A01N43/78
Filed: 2002-05-29
Abstract: The use of N,N'-disubstituted para-phenylene diamine derivatives (I) as insecticides (or more generally for controlling arthropods (especially insects and acarina) and nematodes) is new.  The use of phenylene diamine derivatives of formula (I) or their salts is claimed as insecticides, and for controlling arthropods (especially insects and acarina) and nematodes in the agriculture, forestry, stored goods, material protection and hygiene sectors or as plant protectants. n  =  0-3;  R1, R2  =  H, alkyl, aryl, heteroaryl or acyl;  R3  =  H, halo, alkyl, aryl, heteroaryl, aralkyl, acyl, CN, NO2 or -X-R4;  R4  =  H, alkyl, aryl, heteroaryl, aralkyl or acyl;  X  =  NH, O, S, SO2, NHSO2 or OSO2;  A1  =  CH2, CHR5, CR5R6, CO, CS, CONR4, CSNR4, SO2 or PO2;  R5, R6  =  alkyl, aryl, heteroaryl, aralkyl, CN, NO2 or COR7;  R7  =  H, alkyl, aryl, aralkyl, alkoxy, aryloxy, aralkoxy or -NR8R9;  R8, R9  =  H, alkyl, aryl, aralkyl or heteroaryl;  A2  =  alkyl, aryl, heteroaryl, arylcarbonyl or saturated heterocyclyl; or 1-4C alkyl substituted by 1-9C alkyl, aryl, heteroaryl, halo, =O, OH, NH2, NHCOR10, NHSO2R10, COOR11, CONR12R13, CSNR14R15, SO2OR16, SO2NR17R18, NHCOOR19, NHCONR20R21 or NHCSNR22R23;  R10 - R23  =  H, alkyl, aryl, aralkyl or heteroaryl;  D  =  H, alkyl, aryl, heteroaryl, -Q-R24, halo, NO2, CN, NHCOR25, NHSO2R26, NHCOOR27, NHCONR28R29 or NHCSNR30R31;  Q  =  O, NH, S, CO, CS, SO2, COO, CONR31, CSNR32 or SO2NR33;  R24 - R33  =  H, alkyl, aryl, aralkyl or heteroaryl;  Y  =  -C(Z)-CH(NHR35)-C(R36)2-SR34, -C(Z)-CH(NHR35)-CH2-Im, -C(Z)-(CH2)m-Im, -G1-G2 or -J1-J2-J3-J4;  Im  =  1-(R34)-1H-imidazol-4-yl;  Z  =  O, S or H2;  R34  =  alkyl, aryl, aralkyl, COOR37 or arylsulfonyl;  R35  =  H, acyl or COOR38;  R36  =  H or alkyl;  R37, R38  =  alkyl, aryl or aralkyl;  m  =  0-3;  G1  =  CH2, CO, CS or SO2;  G2  =  COOR39, CONHOH, CONR40R41, CSNR42R43, aryl-(1-3C) alkyl, aryl or heteroaryl; or 1-3C alkyl terminally substituted by COOR44, CONHOH, CONR45R46, CSNR47R48, SR49, SOR50, SO2R51, SO2NR52R53, PO(OR54)OR55, PO(OR54)N(R57)2, OSO2R58, O(PO)OR59, NHSO2R60, NHPO2R61, NHCOR62, NHCSR63, NHCONR64R65, NHCSNR66R67, -S(NH)2-R68 or NHC(=NR70)NHR69;  R39 - R69  =  H, alkyl or aryl;  R70  =  CONH2 or SO2NH2;  J1  =  CH2, CHR71, CR72R73, CO, CS, SO2, SO or PO2;  J2  =  1-26C alkylene (optionally having one CH2 replaced by O, S or NR77) or 2-26C alkenylene (both optionally substituted (os) by aryl, heteroaryl, halo, OH, CN, 1-9C alkoxy, aryloxy, COOR74, CONR75R76, NR77R78, NHC(=NR70)NHR69, SR79 or SO2R80); 3-8C cycloalkylene (os by aryl, heteroaryl, halo, OH, CN, 1-9C alkoxy, aryloxy, COOR74, CONR75R76, NR77R78, SR79 or SO2R80); 3-8C cycloalkylene interrupted by O, S or NR77); or arylene (os by aryl, heteroaryl, halo, OH, CN, 1-9C alkoxy, aryloxy, COOR74, CONR75R76, NR77R78, SR79 or SO2R80);  R71 - R80  =  H, alkyl, aryl, aralkyl or heteroaryl;  J3  =  direct bond, CO, COO, CONR81, CS, CSNR82, SO2, S(NH)2, SO(NH), SO2O, SO2NR83, PO(OR84), PO(OR85)NR86, NR87CO, NR88CS, NR89SO2, OSO2, NR90PO(OR84), OPO(OR91), PO(OR84)O, NR92CONR93, NR94CSNR95, NR96SO2NR97 or NR98C(=NR99)NR100;  R81 - R100  =  H, alkyl, aryl, aralkyl or heteroaryl;  R99  =  H, alkyl, aryl, aralkyl, heteroaryl, CONR101R102, CSNR103R104 or SO2NR105R106;  R101 - R106  =  H, alkyl, aryl, aralkyl or heteroaryl;  J4  =  11-23C alkyl or 11-23C alkenyl (os by aryl or heteroaryl); 11-23C alkynyl; or aryl, heteroaryl or aralkyl (all os by fyrther aryl, heteroaryl and/or aralkyl);  alkyl or acyl moieties have 1-26C unless specified otherwise.  Independent claims are included for: (1) an insect control method using (I); (2) insecticidal compositions containing (I); and (3) the preparation insecticidal compositions, by mixing (I) with extenders and/or diluents and surfactants.