Document Type and Number:
Japanese Patent JPS4932535
Kind Code:
B1
Abstract:
1286603 Benzimidazoles MERCK & CO Inc 21 Sept 1970 [26 Sept 1969] 44896/70 Heading C2C The invention comprises compounds of formula and their salts with alkali or alkaline earth metals, and with pharmaceutically acceptable amines and acids, wherein R is CN, CSNH 2 , CSNH alkyl, CSN(alkyl) 2 , S-alkyl, SO 2 alkyl or 2-thiazolin-2-yl ; R 1 , R 2 , R 3 , R 4 are each F, Cl, Br or I, or one of them may be H; and R 5 is H, alkyl, alkoxyalkyl, C 2-6 alkenyl, carboxyalkyl, carboalkoxyalkyl, C 1-6 alkanoyl, aminoalkyl, alkylaminoalkyl or dialkylaminoalkyl, and when R is CN, R 5 may also be OH, alkoxy, carboxyalkoxy, carboalkoxyalkoxy, sulphoalkoxy or amino-C 2-6 -alkoxy (possibly N-alkyl or N,N- dialkyl substituted). In examples, these compounds are prepared by (1) (R=CN : Ia) dehydrating with SOCl 2 the tri- or tetra-halo- 2-formylbenzimidazole oxime, reacting the tri- or terra-halo-2-chlorobenzimidazole with NaCN, or reacting the tri- or tetra-halo-2-trichloromethylbenimidozole (II) with NH 3 ; (2) (R=CSNH 2 ) reacting Ia with H 2 S; (3) (R=CSNHMe or CSNEt 2 ) reacting ethyl trichlorobenzimidazolyl-2- formimidate with H 2 S followed by MeNH 2 or Et 2 NH; (4) (R = 2-thiazolin-2-yl) reacting II with 2-aminoethanethiol; (5) (R = SMe and SO 2 Me) reacting trichlorobenzimidazole-2-thiol with MeI/NaOH, and oxidizing the product with a peracid; (6) replacing the 1-H atom by reaction with an alkanoic acid anhydride, or the 1-H atom or the H of a 1-OH group by reaction with a halo-substituted compound; (7) (R 5 = NH 2 CH 2 CH 2 O) reacting a 2 - cyano - 1 - phthalimidoethoxytrihalobemimidazole with N 2 H 4 ; (8) removing a 1 -methoxymethyl group with pyridine hydrochloride; (9) standard interconversion reactions of functional groups in a sidechain in the 1-position; (10) salt formation. Intermediates otherwise prepared are:-2- methyl- and 2-styryl-4,6,7-trichlorobenzimidazoles and their 1-hydroxy derivatives; and 4,5,7 -trichlorobenzimidazolone. Veterinary compositions having anthelmintic and anticoccidial activity (which may be administered in conventional forms), and pesticidal compositions having herbicidal and bactericidal activity, comprise compounds of the above formula.
Application Number:
JP8380570A
Publication Date:
August 31, 1974
Filing Date:
September 26, 1970
Export Citation:
International Classes:
A01N43/52; B01J31/00; C07B61/00; C07D235/08; C07D235/10; C07D235/12; C07D235/14; C07D235/22; C07D235/24; C07D235/26; C07D235/28; C07D235/32