Patent EP-2606726-A1 (EP)
IPC: C07C323/36
Filed: 2011-12-21
Abstract: N-arylamidine substituted trifluoroethyl sulfide derivatives (I) are new. N-arylamidine substituted trifluoroethyl sulfide derivatives of formula (I) are new. n : 0-2; either X1-X4 : cycloalkylalkyl, cycloalkyloxy, cycloalkyl-alkoxy, cycloalkylthio, cycloalkyl-alkylthio, cycloalkylsulfinyl, cycloalkyl-alkylsulfinyl, cycloalkylsulfonyl or cycloalkyl-alkylsulfonyl (all optionally saturated), phenylalkyl, phenoxy, phenyl-alkyloxy, phenoxy-alkyl, phenylthio, phenyl-thioalkyl, phenylsulfinyl, phenylsulfonyl, heteroarylalkyl, heteroaryloxy, heteroaryl-thio, heteroaryl-alkyloxy, heteroaryl-sulfinyl or heteroaryl-sulfonyl (all optionally substituted), H, halo, OH, NH 2, OCN, SCN, SF 5, trialkylsilyl, (halo)alkyl, cyanoalkyl, hydroxyalkyl, alkoxycarbonylalkyl, alkoxyalkyl, (halo)alkenyl, cyano-alkenyl, (halo)alkynyl, cyano-alkynyl, (halo)alkoxy, cyanoalkoxy, hydroxycarbonyl-alkoxy, alkoxycarbonyl-alkoxy, alkoxy-alkoxy, alkyl-hydroxyimino, alkoxyimino, (halo)alkyl-alkoxyimino, (halo)alkylthio, alkoxy-alkylthio, alkylthioalkyl, (halo)alkylsulfinyl, alkoxy-alkylsulfinyl, alkylsulfinyl-alkyl, (halo)alkylsulfonyl, alkoxy-alkylsulfonyl, alkylsulfonyl-alkyl, alkyl-sulfonyloxy, (halo)alkylcarbonyl, carboxy, alkylcarbonyloxy, (halo)alkoxycarbonyl, alkoxycarbonylalkyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenyl-aminocarbonyl, cycloalkylaminocarbonyl, alkylsulfonylamino, aminosulfonyl, alkyl-aminosulfonyl, dialkylamino-sulfonyl, alkylsulfoximino, aminothiocarbonyl, alkyl-aminothiocarbonyl, dialkylamino-thiocarbonyl, NR4R5 or saturated, partially saturated or aromatic 3-6-membered ring (optionally containing 1-3 O, S or N and optionally mono- or polysubstituted by G1); or X2+X3+C, X3+X4+C : 5-6-membered ring (optionally substituted and optionally interrupted by O, S, N or CO); either R4, R5 : H, CN, (halo)alkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, (halo)alkenyl, cyano-alkenyl, (halo)alkynyl, cyano-alkynyl, acyl or alkoxycarbonyl; or R4+R5+N to which R4 and R5 are bonded : optionally saturated 5-8-membered ring (optionally substituted and optionally interrupted by O, S or N); R3 : H, 2-8C alkyl, CN, haloalkyl, alkoxyalkyl, cyanoalkyl, alkylthioalkyl, (halo)alkenyl, (halo)alkynyl or saturated, partially saturated or aromatic 3-6-membered ring (optionally containing 1-3 O, S or N and optionally mono- or polysubstituted by G1); either R1, R2 : alkylcarbonyl, alkoxycarbonyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (halo)alkylsulfinyl, (hetero)arylsulfinyl, (hetero)arylalkylsulfinyl, (halo)alkylsulfonyl, (hetero)arylsulfonyl or (hetero)arylalkylsulfonyl (all optionally substituted), H, CN, (halo)alkyl, alkoxy, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, (halo)alkenyl, cyano-alkenyl, (halo)alkynyl, cyano-alkynyl, -(CH 2) m-R6, -O-(CH 2) m-R6, -(CH 2) m-R6 or saturated, partially saturated or aromatic 3-6-membered ring (optionally containing 1-3 O, S or N, optionally once or twice interrupted by C=O, SO or SO 2, and optionally mono- or polysubstituted by G1); R1+R2+N to which R1 and R2 are bonded, R1+R3+atoms to which R1 and R3 are bonded : 4-8-membered ring (optionally saturated, optionally substituted, and optionally containing S, O (where O are not immediately adjacent to each other), N or carbonyl); R6 : saturated, partially saturated or aromatic 3-6-membered ring (optionally containing 1-3 O, S or N, optionally once or twice interrupted by C=O, and optionally mono- or polysubstituted by G1); m : 1-4; and G1 : cycloalkyl, cycloalkoxy, cycloalkylalkyl or cycloalkyl-alkoxy (all optionally substituted and optionally interrupted by O, S or N) or halo, CN, NO 2, OH, NH 2, carboxy, (halo)alkyl, (halo)alkenyl, alkynyl, (halo)alkoxy, alkylsulfonyl-oxy, (halo)alkylthio, (halo)alkylsulfinyl, (halo)alkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonyl, alkylcarbonyl, alkylcarbonyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylamino-thiocarbonyl, dialkylamino-thiocarbonyl, cycloalkylamino, alkylsulfonylamino, aminosulfonyl, alkyl-aminosulfonyl or dialkyl-aminosulfonyl. Independent claims are also included for: (1) preparing (I); and (2) an active substance composition comprising (I) and at least one further insecticidal, acaricidal or nematicidal active substance. [Image] ACTIVITY : Insecticide. The ability of (I) to control insect was tested in Chinese cabbage against Phaedon cochleariae. The results showed that 2,2,2-trifluoro-N-[2-fluoro-4-methyl-5-(2,2,2-trifluoro-ethanesulfinyl)-phenyl]-N'-propyl-acetamidine exhibited 100% insecticidal effect. MECHANISM OF ACTION : None given.