Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-01-20
1999-11-30
Robinson, Allen J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514 63, 514259, 514399, 514619, A01N 3718, A01N 4350, A01N 4354, A01N 5500
Patent
active
059943823
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP96/03358, filed Jul. 31, 1996.
The present invention relates to a fungicidal mixture which comprises ##STR2## where R is hydrogen or halogen and b) an azole derivative II selected from the group of the compounds II.1 to II.17 (2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)tetrahydrofuryl]-1H-1,2,4- triazole (II.1) ##STR3## 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (II.2) ##STR4## (.+-.)-4-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2 -yl]phenyl 4-chlorophenyl ether (II.3) ##STR5## (E)-(R,S)-1-(2,4-dichlorophenyl)-4,4- dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (II.4) ##STR6## (Z)-2-(1H-1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl) -3-(2-chlorophenyl)oxirane (II.5) ##STR7## 4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazolylmethyl)butyronitrile (II.6) ##STR8## 3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl) quinazolin-4(3H)-one (II.7) ##STR9## bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-ylmethyl)silane (II.8) ##STR10## (R,S)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol (II.9) ##STR11## (1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1 -ylmethyl)cyclopentanol (II.10) ##STR12## N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1-carboxamide (II.11) ##STR13## (.+-.)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2, 4-triazole (II.12) ##STR14## (R,S)-1-(4-chloro phenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (II.13) ##STR15## (.+-.)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazolyl)propyl 1,1,2,2-tetrafluoroethyl ether (II.14) and ##STR16## (E)-1-[1-[[4-chloro-2-(trifluoromethyl)phe nyl]imino]-2-propoxyethyl]-1H-imidazole (II.15) ##STR17## (RS)-2,4'-difluoro-.alpha.-(1H-1,2,4-triazol-1-ylmethyl)benzhydryl alcohol (II.16) ##STR18## 2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile (II.17) ##STR19## in a synergistically active amount.
Furthermore, the invention relates to methods of controlling harmful fungi using mixtures of the compounds I and II, and to the use of the compound I and of the compounds II for the preparation of such mixtures.
The compounds of the formula I, their preparation and their action against harmful fungi are known from the literature (WO-A 95/18,789). Also known are the azole derivatives II, their preparation and their action against harmful fungi: 5-6, 439 (1990); 5-3, 411 (1992); 413 (1984); 5-4, 419 (1992); 1, 49 (1988);
With the view of reducing the rates of application and improving the spectrum of action of the known compounds, it was an object of the present invention to provide mixtures which have an improved action against harmful fungi combined with a reduced total amount of active ingredients applied (synergistic mixtures).
Accordingly, we have found that this object is achieved by the mixtures defined at the outset. Moreover, we have found that, when using the compound I and the compounds II simultaneosuly together or separately or when using the compound I and the compounds II in succession, a better control of the harmful fungi can be achieved than with the individual compounds.
R in formula I is hydrogen or a halogen atom, such as fluorine, chlorine, bromine and iodine, especially hydrogen, fluorine and chlorine, in partiuclar hydrogen or fluorine.
Relative to the C.dbd.N double bond, the compounds of the formula I can be present in the E or the Z configuration (relative to the carboxylic acid function). Accordingly, they can be used, in the mixture according to the invention, either as the pure E or Z isomer or as an E/Z isomer mixture. The E/Z isomer mixture or the E isomer is preferably used, the E isomer being especially preferred.
The C.dbd.N double bonds of the oxime ether groups in the side chain of the compounds I can in each case be present as pure E or Z isomers or E/Z isomer mixtures. The compounds I can be used, in the mixtures according to the invention, as isomer mixtures, but also as pure isomers. With a view to their use, particularly preferred compounds I are those where both ox
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Ammermann Eberhard
Bayer Herbert
Lorenz Gisela
Muller Ruth
Saur Reinhold
BASF - Aktiengesellschaft
Robinson Allen J.
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