Patent EP-2072506-A1 (EP)
IPC: A01N43/78
Filed: 2007-12-21
Abstract: Thiadiazolyloxyphenylamidine or thiazolyloxyphenylamidine compounds (I) are new. Thiadiazolyloxyphenylamidine or thiazolyloxyphenylamidine compounds of formula (I) are new. Y 1>CR 7>or N; either R 1>1-12C-alkyl, 2-12C-alkenyl, 2-12C-alkynyl, cyclic 3-12C-alkyl, 4-12C-alkenyl or 4-12C-alkynyl (where in the ring system of all cyclic groups, one or more C atoms are replaced by heteroatoms of N, O, P or S, and substituted by one or more R1a, X, OR1a, S(R1a) 2, N(R1a) 2, Si(R1a) 3, COOR1a, CN or CON(R1a) 2), H, SH or SR2a; and R 2>, R 3>1-12C-alkyl, 2-12C-alkenyl, 2-12C-alkynyl, cyclic 3-12C-alkyl, 4-12C-alkenyl, 4-12C-alkynyl, 5-18C-aryl, 7-19C-aralkyl or 7-19C-alkaryl, where in the ring system of all cyclic groups, one or more C atoms are replaced by heteroatoms of N, O, P or S, and substituted by one or more groups of R1a, X, OR1a, SR1a, N(R1a) 2, Si(R1a) 3, COOR1a, CN or CON(R1a) 2; or R 2>R 3>, R 2>R 1>, R 1>R 3>4-7 membered ring containing heteroatoms of N, O, P or S, which is optionally replaced by one or more X, R1a, OR1a, SR1a, N(R1a) 2, Si(R1a) 3, COOR1a, CN or CON(R1a) 2; R 4>, R 5>H, X, CN, 1-12C-alkyl, 2-12C-alkenyl, 2-12C-alkynyl, cyclic 3-12C-alkyl, 4-12C-alkenyl, 4-12C-alkynyl, 5-18C-aryl, 7-19C-aralkyl or 7-19C-alkaryl, where in the ring system of all cyclic groups, one or more C atoms are replaced by heteroatoms of N, O, P or S, and substituted by one or more groups of R1a, X, OR1a, SR1a, N(R1a) 2, Si(R1a) 3, COOR1a, CN or CON(R1a) 2; R 6>X, CN, SH, SR2a, OR2a, (C=O)-R2a, 1-12C-alkyl, 2-12C-alkenyl, 2-12C-alkynyl, cyclic 3-12C-alkyl, 4-12C-alkenyl, 4-12C-alkynyl, 5-18C-aryl, 7-19C-aralkyl or 7-19C-alkaryl, where in the ring system of all cyclic groups, one or more C atoms are replaced by heteroatoms of N, O, P or S, and substituted by one or more groups of OR1a, SR1a, N(R1a) 2, Si(R1a) 3, COOR1a, CN or CON(R1a) 2; R 7>X, CN, SH, SR2a, OR2a, (C=O)-R2a, 1-12C-alkyl, 2-12C-alkenyl, 2-12C-alkynyl, cyclic 3-12C-alkyl, 4-12C-alkenyl, 4-12C-alkynyl, 5-18C-aryl, 7-19C-aralkyl or 7-19C-alkaryl, where in the ring system of all cyclic groups, one or more C atoms are replaced by heteroatoms of N, O, P or S, and substituted by one or more groups of R1a, X, OR1a, SR1a, N(R1a) 2, Si(R1a) 3, COOR1a, CN or CON(R1a) 2; n : 0-5; R1a : H or 1-12C-alkyl; and R2a : 1-12C-alkyl substituted by one or more groups from R1a, X, OR1a, SR1a, N(R1a) 2, Si(R1a) 3, COOR1a, CN or CON(R1a) 2. Independent claims are included for: (1) the preparation of (I); (2) a thiazolyl or thiadiazolylalcohol compound of formula (II); (3) a thiazolyl- or thiadiazolyl-derivative of formula (IV); (4) a thiazolyl- or thiadiazolylaminophenylether compound of formula (VIII); (5) a thiazolyl- or thiadiazolylaminophenylether compound of formula (VI); and (6) a process for the preparation of (II) or (IV) (in which Z is Cl and Y 1>is N) (preferred), comprising reacting cyclopropanecarboxamidine compound of formula (XX) with trichloromethyl thiohypochlorite. Z : a leaving group, preferably halo, triflate, mesylate, tosylate or SO 2Me. [Image] [Image] [Image] ACTIVITY : Antimicrobial; Fungicide; Antibacterial; Virucide; Herbicide; Antiparasitic. MECHANISM OF ACTION : None given.