Patent DE-19741654-A1 (DE)
Title: Substituted triazine derivatives useful as pesticides active against e.g. insects, arachnids, helminths and fungi
Inventor: SCHAPER WOLFGANG DR
IPC: A01N43/66
Filed: 1997-09-22
Abstract: 2-(Substituted amino or hydroxy)-1,3,5-triazine compounds are new where the substituent on the amino or hydroxy is an optionally substituted carbocyclic, an optionally substituted benzofused carbocyclic or an optionally substituted heterocyclic group containing oxygen and/or sulfur atoms. Substituted 1,3,5-triazines of formula (I) and their N-oxides and/or salts are new.  R1, R2 = H; 1-6C alkyl or 3-6C cycloalkyl (both optionally halo-substituted); halo, 1-4C alkoxy-(1-4C alkyl), 2-6C alkenyl, 2-6C alkynyl or 1-4C cyanoalkyl; X = O or NH; Q = a group of formula (i)-(iv); in (i), the ring is optionally monounsaturated; n = 2-7; R3, R4 = H or Me; R5 = H; halo, CN, -NCS, NO2,1-20C alkyl (optionally substituted by halo, OH, CN, NO2, or -NCS); or 2-20C alkenyl or alkynyl; or 3-8C cycloalkyl, cycloalkenyl,  cycloalkoxy or cycloalkylthio; 1-4C alkyl-(3-8C)cycloalkyl; or 1-20C alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl; 2-20C alkoxyalkyl; 1-4C alkyl (which is itself substituted by 3-8C cycloalkyl or cycloalkoxy, 3-8C cycloalkyl-(1-4C)-alkoxy, 1-8C haloalkoxy, 1-8C alkylthio, 3-8C cycloalkylthio, 3-8C cycloalkyl-(1-4C)-alkylthio, aryl, heteroaryl, aryloxy, aryl-(1-4C)-alkoxy, heteroaryloxy, heteroaryl-(1-4C)-alkoxy, arylthio, aryl-(1-4C)-alkylthio, heteroarylthio or heteroaryl-(1-4C)-alkylthio); 1-4C alkylthio (which is itself substituted by aryl or heteroaryl); 1-4C alkoxy (which is itself substituted by 3-8C cycloalkyl, aryl or heteroaryl); 1-8C alkoxy-(1-4C)-haloalkoxy; 1-8C haloalkoxy-(1-4C)-haloalkyl; aryl; aryloxy; aryl-(2-4C)-alkenyl; aryl-(2-4C)-alkynyl; heteroaryl; heteroaryloxy; arylthio; heteroarylthio; tri(1-8C)-alkylsilyl; di(1-8C)-alkyl-(3-8C)-cycloalkylsilyl; di(1-8C)-alkyl-(phenyl-(1-4C)-alkyl)silyl; dimethyl-(mono, di or tris-oxa-(1-12C)-alkyl)silyl; ((1-8C)-alkyldimethylsilyl)-(1-8C)-alkyl; dimethylphenylsilyl; or a group of formula (v); and where the aryl or heteroaryl groups (and their derived groups) are optionally substituted by up to 3 groups (or in the case of F, by up to the maximum possible); or R5 = COR6, COOR6 or CON(R6)2; R6 = H, 1-20C alkyl or haloalkyl, 3-8C cycloalkyl or cycloalkenyl, 3-8C cycloalkyl-(1-4C)-alkyl, 2-20C alkenyl or alkynyl, aryl, aryl-(1-4C)-alkyl, aryl-(2-4C)-alkenyl, aryl-(2-4C)-alkynyl, heteroaryl or heteroaryl-(1-4C alkyl); or N(R6)2 = a group of formula (vi) or (vii); ring D = saturated or aromatic; m = 2-7; q, r = 0-4; q+r = 2-4;  in (vi), one CH2 may be replaced by O, S or NR9; R8, R9 = H, 1-20C alkyl, 1-20C haloalkyl, 3-8C cycloalkyl, 1-20C alkoxy, 1-20C alkylthio, phenyl-(1-4C)-alkyl, or phenyl and the phenyl groups are optionally substituted by up to 3 substituents (or in the case of F, by up to the maximum possible); the phenyl, aryl or heteroaryl groups or their derived groups in R6, R8, R9 are optionally substituted by up to 3 groups (or, in the case of F, by up to the maximum possible number); and when group (i) = cycloalkyl where R5 takes the 4-position relative to the pyrimidinyl-amino- or -alkoxy group (sic), the cis configuration is preferred for these substituents; and for all groups (i), R4, R5 are not both H; Z1 = CHR6, NOR6 or a group of formula (viii); U = a bond or CH2O; V = a bond, O, S, SO, SO2, OSO2, SO2O; or  VR6 = OCO-N(R6)2; in (iii), the aromatic portion of the condensed ring system may be substituted by up to 3 groups (or in the case of F, by up to the maximum possible number); A = a bond, O or S; B = CH2, O or S; at least 1 of A or B = O or S; where if (iv) involves a 6-membered ring, R6 is cis with respect to the pyrimidinyl-amino- or -alkoxy group (sic); and  in all of groups (i)-(iv), so far as they are not restricted by the foregoing, in alkyl, alkenyl and alkynyl groups (and all derived groups), H atoms may be partly (or in the case of F atoms, completely) replaced by halogens; and further, for alkyl, alkenyl and alkynyl groups in all of (i)-(iv), up to 3 non-adjacent saturated C units may be replaced by O, S, SO, SO2 or Si(CH3)2.