Patent DE-19837620-A1 (DE)
Title: New diphenylmethyl-substituted hydrazine derivatives useful
Inventor: PASCUAL ALFONS
IPC: C07C309/65
Filed: 1998-08-19
Abstract: Diphenylmethyl-substituted hydrazine derivatives(I) are new.- DETAILED DESCRIPTION - Diphenylmethyl-substitutedhydrazine derivatives of formula (I) and their isomers, tautomers and salts are new.   n 0-5;   o  0-4;   R  1   halo-(1-6C alkoxy), S(O) m R 7 ,OS(O)R 7 , OS(O) 2 R 7  or CH 2 S(O) m R 7 ;   m  0-2;   R  2 halo,1-8C alkyl, halo-(1-8C alkyl), 3-6C cycloalkyl, halo-(3-6Ccycloalkyl), 2-6C alkenyl, 1-8C alkoxy, halo-(1-8C alkoxy),halo-(2-6C alkenyl), 3-6C alkenyloxy, 2-6C alkynyl, 3-6Calkynyloxy, halo-(2-6C alkynyl), halo-(3-6C alkynyloxy), 1-8Calkylthio, halo-(1-8C alkylthio), 1-8C alkylsulfinyl, halo-(1-8Calkylsulfinyl), 1-8C alkylsulfonyl, halo-(1-8C alkylsulfonyl),phenyl, NO 2  or CN;   R  3   halo, 1-8C alkyl, halo-(1-8C alkyl),3-6C cycloalkyl, halo-(3-6C cycloalkyl), 2-6C alkeyl, 1-8Calkoxy, halo-(1-8C alkoxy), halo-(2-6C alkenyl), 3-6C alkenyloxy, halo-(3-6C alkenyloxy), 2-6C alkynyl, 3-6C alkynyloxy, halo-(2-6Calkynyl) or halo-(3-6C alkynyloxy);   Or R 1  is H and two R 3 groups together form (provided they are in the o-position to each other) a 5-7 membered saturated ring, in which one or two CH 2 groups may be replaced by O, S or NH hetero groups, and where the ring is optionally substituted by 1-4 1-6C alkyl, halo or halo-(1-6C alkyl) groups; #R 4  = H, 1-8C alkyl, 1-4C alkoxy-(1-8Calkkyl), (1-8C alkyl)carbonyl, (1-8C alkoxy)carbonylbenzoyl orbenzoyl, which may be substituted by 1-5 halo, 1-4C alkyl, halo-(1-4C alkyl), 1-8C alkoxy, halo-(1-8C alkoxy), NO 2  or CN groups; #R 5  = H, 1-8C alkyl, halo-(1-8C alkyl), 1-8C alkenyl(sic), 3-6C cycloalkyl, halo-(3-6C cycloalkyl), 3-8C alkenyl, halo-(3-6C alkenyl), 3-6C alkenyloxy-CH 2 , 3-6C alkynyl, halo-(3-6C alkynyl), 1-8C alkoxy-(1-8C alkyl), halo-(1-8Calkoxy)-(1-8C alkyl), phenyl (optionally substituted by 1-5 1-4Calkyl, halo(1-4C alkyl), 1-8C alkoxy, halo-(1-8C alkoxy), NO 2 or CN groups), (CH 2 ) p COOR 9 , (CH 2 ) p COR 9 , (CH 2 ) p CONR 1 o R - 1  1 or (CH 2 ) p CN; #p = 0-4; #R 6  = H; 1-8C alkyl, 3-8C alkenyl or3-8C alkynyl (all optionally substituted by halo, 1-8C alkoxy,1-8C alkylthio, 1-8C alkyl-S(O), 1-8C alkyl-S(O) 2 , 1-8Calkyl-CO, 1-8C alkyl-OCO, 1-8C alkyl-COO or di(1-8C alkyl)amino);3-6C cycloalkyl, 3-6C cycloalkyl(1-8C alkyl), 3-6C cycloalkenyl,3-6C cycloalkenyl-(1-8C alkyl) or 3-6C cycloalkenyl-(1-8Calkenyl) (sic) (all optionally substituted by halo, 1-8C alkyl, halo-(1-8C alkyl), 1-8C alkoxy, halo-(1-8C alkoxy), 1-8Calkylthio, 1-8C alkyl-S(O), 1-8C alkyl-S(O) 2 , 1-8Calkoxycarbonyl, di(1-8C alkyl)amino) or 1-8C alkyl-COO); or aryl or heteroaryl  (optionally substituted by 1-5 halo, 1-4C alkyl, halo-(1-4C alkyl), 1-4C alkoxy, halo-(1-4C alkoxy), NO 2  or CN groups); N(R 1  0 )(R 1  1 ), OR 1  2 , SR 1  2 , or COOR 1  2 ; #R 7 =1-8C alkyl or halo-(1-8C alkyl); #R 9  = H, 1-8C alkyl or halo-(1-8C alkyl); #R 1  0 , R 1  1  = independently H, 1-8C alkyl, halo-(1-8C alkyl), 3-8C alkenyl, 3-8C alkynyl, 1-8C alkoxy orphenyl; #R 1  2  = H, 1-8C alkyl, halo-(1-8C alkyl), 3-6Ccycloalkyl, 3-8C alkenyl, 3-6C alkynyl or phenyl; #Y = O orS.- TECHNOLOGY FOCUS - ORGANIC CHEMISTRY - Preparation: (I) are prepared by:(1) reducing a compound of formula (II);(2) reacting a compound of formula (I) R 4  = H) with a compound R 4 -X 1  (III)(3) reacting a compound of formula (I) (R 5  = H) with a compound R 5 -X 2  (IV)(4) reacting a compound of formula (V) with one of formula X 3 -C(=Y)-R 6 (VI).    X 1 , X 2 , X 3   a leaving group, preferably halo.- ACTIVITY - Insecticidal; acaricidal. Young soya plants were sprayed with an aqueous composition containing 400 ppm trifluoromethanesulfonic acid4-[(N'-acetyl-N-methylhydrazino)-(4 -bromophenyl)methy l]ester;once the spray has dried, the plants were allowed to come into contact with Spodoptera littoralis caterpillars. Three days later, the plants were found to have more than 80% fewer caterpillars than untreated controls.  0.1-,00 (preferably 0.1-500) ppm, or1-2,00 (preferably 10-1,00, especially 20-600) g/ha.- SPECIFIC SUBSTANCES - SPECIFIC COMPOUNDS - A large number of compounds (I) are specifically disclosed e.g. trifluoromethanesulfonic acid4-[(N'-acetyl-N-methylhydrazino)-(4-bromophenyl)methy l]ester(Ia)