Patent EP-2706058-A1 (EP)
Inventor: SEITZ THOMAS
IPC: A01P3/00
Filed: 2011-04-11
Abstract: Use of dithiine derivatives (I) for controlling undesirable microorganisms, preferably phytopathogenic fungi, in crop protection and material protection, and in the area of household and hygiene, is claimed. Use of dithiine derivatives of formula (I) for controlling undesirable microorganisms, preferably phytopathogenic fungi, in crop protection and material protection, and in the area of household and hygiene, is claimed. Either R1-R4 : (hetero)aryl or (hetero)aryl-(1-4C-alkyl) (both optionally substituted by one or more halo, nitro, cyano, 1-4C-(halo)alkyl or 1-4C-alkoxy), H, halo, nitro, 1-8C-(halo)alkyl, 1-8C-(halo)alkoxy, 1-8C-(halo)alkylthio, -COR5, -CH 2COR5 or N-phenylmorpholin-4-carboximidoyl; and R5 : hydroxy, 1-4C-alkyl or 1-4C-alkoxy; and m, n : 0-2; or R1+C+R2 : 5- or 6-membered heterocycle having one or two heteroatoms comprising N, S or O, where the heterocycle contains one or two C(=O)- or (C=S)- groups, and is optionally substituted by 1-4C-alkyl, -COR6 or di(1-4C-alkyl)amino, and when the heterocycle is pyrazine then the pyrazine is substituted by one or two 1-4C-alkyl, -COR6 or di(1-4C-alkyl)amino, and the heterocycle is not 1,3-dithio-2-(thi)one-ring; and either R3, R4 : H or R1 and R2; or R3+C+R4 : an aryl ring; and R6 : hydroxy, 1-4C-alkyl or 1-4C-alkoxy, where both R1 and R2, and R3 and R4 are not optionally substituted 1H-pyrrol-2,5-dione-ring; and m, n : 0; or R1, R2 : -C(=O)-X1-C(=O)-; and R3, R4 : -C(=O)-X2-C(=O)-; and X1 : S or NR7; and X2 : S or NR7a, or phenyl-1,2-diyl; and R7 : 1-8C-(halo)alkylthio, 1-4C-alkylamino, di-(1-4C-alkyl)amino, phenylsulfonylamino or aryl or aryl-(1-4C-alkyl) (both substituted by three halo, 1-4C-(halo)alkyl, 1-4C-(halo)alkoxy or 1-8C-alkylthio); and R7a : R7 or H; and m, n : 0; or R1R2 : -C(=O)-CR8=CR9-C(=O)-; and either R3, R4 : cyano; or R3R4 : -C(=O)-CR8=CR9-C(=O)-; and R8, R9 : H, halo, 1-8C-alkyl, 1-8C-(halo)alkoxy or 1-8C-(halo)alkylthio, where at least one R8 or R9 is not H, when both R1 and R2, and R3 and R4 are -C(=O)-CR8=CR9-C(=O)-; and m, n : 0; or R1R2 : -C(OH)=CR8-CR9=C(OH)-; either R3, R4 : cyano; or R3R4 : -C(=O)-CR8=CR9-C(=O)-; and R8, R9 : H, halo, 1-8C-alkyl, 1-8C-(halo)alkoxy or 1-8C-(halo)alkylthio; and m, n : 0. Independent claims are included for: (1) dithiine derivatives of formulae (IA)-(ID) (representatives of (I)); and (2) a composition comprising (I) and at least a further agent comprising insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners or semiochemicals. R1a+C+R2a : 5- or 6-membered heterocycle having one or two heteroatoms comprising N, S or O, where the heterocycle contains one or two C(=O)- or (C=S)- groups, and is optionally substituted by 1-4C-alkyl, -COR6a or di(1-4C-alkyl)amino, and when the heterocycle is pyrazine then the pyrazine is substituted by one or two 1-4C-alkyl, -COR6 or di(1-4C-alkyl)amino, and the heterocycle is not 1,3-dithio-2-(thi)one-ring; and either R3a, R4a : H or R1a and R2a; or R3a+C+R4a : aryl ring; R6a : R6; either R3c, R4c : cyano; or R3cR4c : -C(=O)-CR8=CR9-C(=O)-, where at least one of R8 or R9 is not H; and either R3d, R4d : cyano; or R3dR4d : -C(=O)-CR8=CR9-C(=O)-. [Image] [Image] ACTIVITY : Fungicide. The fungicidal activity of (I) against Alternaria solaniwas tested in tomato. The results showed that 6,7-dimethyl-5,8-dioxo-5,8-dihydro-1,4-benzodithiin-2,3-dicarbonitrile (1500 ppm) exhibited an efficiency of 100%. MECHANISM OF ACTION : None given.