Patent DE-102007010801-A1 (DE)
Title: Use of new and known 2,4-diaminopyrimidine derivatives as fungicides, especially for controlling phytopathogenic fungi
IPC: C07D401/12
Filed: 2007-03-02
Abstract: Use of new and known 2,4-diaminopyrimidine derivatives (I), is claimed, as fungicides. Use of 2,4-diaminopyrimidine derivatives of formula (I) and their salts, is claimed, as fungicides. X 1> : N or CR 3>; X 2> : N or CR 4>; A : C(R 14>) 2 or a bond; R 1>-R 5> : H, halo, CN, OH, NO 2, heterocyclyl, carbocyclyl, OR, SR, SOR, SO 2R, SONRR, SO 2NRR, OSO 2NRR, COR, NRCOOR', NRCSOR', NRR, NRCOR, NRSO 2R', NRSOR', OCONRR, OCOR, CONRR, COOR, CR 2OR, (CH 2) mQ, optionally substituted 1-8C alkyl, 1-8C haloalkyl or 3-8C cycloalkyl, or two of R 2>-R 4> can form a ring; m : 1-8; Q : CR 2OR, OR, SR, SOR, SO 2R, SONRR, SO 2NRR, NRR, COOR, COR, NRCOR or NRCOOR; R 6> : H; benzyl, 1-8C alkyl, 1-4C alkylcarbonyl, (1-4C)alkoxy(1-4C)alkyl, 2-6C alkenyl or 2-6C alkynyl, all optionally substituted; 1-4C alkoxycarbonyl, 1-6C alkylsulfinyl, 1-6C alkylsulfonyl, 3-8C cycloalkyl, 1-6C haloalkyl, 1-4C haloalkylsulfinyl, 1-4C haloalkylsulfonyl, haloalkoxyalkyl, halocycloalkyl, CHO, formyl(1-3C)alkyl, alkanoylalkyl, alkoxycarbonylalkyl, haloalkanoylalkyl, haloalkoxycarbonyl, 1-8C alkylcarbonyl, 1-8C alkoxycarbonyl, 1-8C alkylthiocarbonyl, alkoxyalkanoyl, alkenyloxycarbonyl, alkynyloxycarbonyl, 3-8C cycloalkylcarbonyl 1-6C haloalkylcarbonyl, 1-6C haloalkylthiocarbonyl, 1-6C haloalkoxycarbonyl, 3-6C haloalkenyloxycarbonyl, 3-6C haloalkynyloxycarbonyl, haloalkoxyalkanoyl, halocycloalkylcarbonyl, CH 2CCR 1>', CH 2CH=CHR 1>', CH=C=CHR 1>', COCOR 2>, CONR 3>R 4>, CH 2NR 5>R 6>, trialkylsilyl, trialkylsilylethyl or phenyldialkylsilyl; R 1>' : H, 1-6C alkyl, 1-6C haloalkyl, 2-6C alkenyl, 2-6C alkynyl, 3-7C cycloalkyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl or CN; R 7> : H, CN, Me or 1-3C haloalkyl; R 8> : halo, CN, Me or 1-3C haloalkyl; R 9> : H; 1-8C alkyl, aryl, benzyl, alkoxyalkyl, alkenyl or alkynyl, all optionally substituted; 3-8C cycloalkyl, 1-8C haloalkyl, trialkylsilyl, 1-6C alkylsulfinyl or 1-6C alkylsulfonyl; R 10> : H, 1-8C alkoxy, optionally substituted 1-8C alkyl, 3-8C cycloalkyl, 1-8C haloalkyl, trialkylsilyl, optionally substituted aryl, COOR, COR, OR; R 11> : H, F, Cl, Br, optionally substituted 1-8C alkyl, 1-8C alkoxy, 3-8C cycloalkyl, 1-8C haloalkyl, trialkylsilyl, optionally substituted aryl or optionally substituted cyclopropyl; R 12>, R 13> : 1-8C alkyl, 1-8C haloalkyl, 3-6C cycloalkyl, 2-6C alkenyl, 2-6C alkynyl, aryl, benzyl or 3-7 membered saturated or unsaturated ring optionally containing 1-4 N, O and S heteroatoms (all optionally substituted), 1-4C trialkylsilyl or 1-4 alkoxy 1-4C alkyl, or NR 12>R 12>, NR 12>COR 12>, R 13> + R 13> : 3-7 membered optionally substituted, saturated or unsaturated ring optionally containing 1-4 N, O and S heteroatoms, where two O atoms are not adjacent; R 14> : H, F, Cl, Br or 1-8C alkyl, 3-8C alkoxy, 3-8C cycloalkyl, 1-8C haloalkyl or 1-4C trialkylsilyl (all optionally substituted), or R 14> + R 14> : carbonyl or thiocarbonyl; R : H, substituted 1-8C alkyl, trialkylsilyl or optionally substituted 1-8C haloalkyl, 3-6C cycloalkyl, 2-6C alkenyl, 3-6C alkynyl, aryl, alkoxyalkyl, benzyl or a 3- to 7-membered ring with 0-4 heteroatoms, or R+R forms a 3- to 7-membered ring with 0-4 other heteroatoms, and R' : trialkylsilyl, alkoxyalkyl or optionally substituted 1-8C alkyl, 1-8C haloalkyl, alkenyl, alkynyl, 3-6C cycloalkyl, aryl, benzyl or a 3- to 7-membered ring with 0-4 heteroatoms, or R'+R' forms a 3- to 7-membered ring with 0-4 other heteroatoms. Independent claims are also included for 6 new compounds of formula (IA)-(IF) and their salts. R 8a> : Cl, I, CH 2F, CF 2H or CCl 3; X 1b> : N or C(R 3b>); R 3b> : e.g. H, halo, CN, OH or NO 2, or 2 of adjacent R 2>, R 3b> and R 4> optionally with R 12> and R 13> : 3-7 membered ring; m : 1-8; X 1c> : N or C(R 3c>); X 2c> : N or C(R 4c>); R 2c>, R 4c> : e.g. H, halo, CN, OH or NO 2, or 2 of adjacent R 2c>, R 3c> and R 4c> optionally with R 12> and R 13> : 3-7 membered ring; R 3c> : e.g. H, F, Cl, Br, I, CN, OH, NO 2, OMe or OEt; X 1e> : N or C(R 3e>); R 3e> : e.g. H, halo, CN, OH or NO 2, or 2 of adjacent R 2>, R 3e> and R 4> optionally with R 12> and R 13> : a ring; group of formula (i) in (IE) : e.g. (2-oxo-2,3-dihydro-1H-indol-5-yl)amino, 1H-indol-6-ylamino or 1H-indol-5-ylamino, and R 1f> : e.g. H, F, Br, I, CN, OH or NO 2, or any two adjacent R 2>, R 3> and R 4>, optionally with R 12> and R 13> : 3-7 membered ring, with a specified proviso. N.B.: Full Definitions for compounds (IA)-(IF) are given in the Definitions ('Full Definitions') field. [Image] [Image] [Image] [Image] [Image] ACTIVITY : Plant antifungal. Several compounds (I), e.g. 5-chloro-4-cyclopropylamino-2-(3-chlorophenylamino)pyrimidine, gave more than 70% protection of young apple plants against Venturia inaequalis infection at a concentration of 100 ppm. MECHANISM OF ACTION : None given.