Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-06-19
2002-02-26
Robinson, Allen J. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S063000, C514S259500, C514S383000, C514S399000
Reexamination Certificate
active
06350765
ABSTRACT:
The present invention relates to fungicidal mixtures for controlling harmful fungi and also to methods for controlling harmful fungi using such mixtures.
WO 97/08952 describes mixtures of amide compounds of the formula I
A—CO—NR
1
R
2
(I)
in which
A is an aryl group or an aromatic or non-aromatic, 5- or 6-membered heterocycle which has from 1 to 3 hetero atoms which are selected from O, N and S;
where the aryl group or the heterocycle may or may not have 1, 2 or 3 substituents which are selected, independently of one another, from alkyl, halogen, CHF
2
, CF
3
, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl;
R
1
is a hydrogen atom;
R
2
is a phenyl or cycloalkyl group which may or may not have 1, 2 or 3 substituents which are selected from alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkenyloxy, phenyl and halogen, where the aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or the cycloaliphatic radicals may be substituted by from 1 to 3 alkyl groups and where the phenyl group may have from 1 to 5 halogen atoms and/or from 1 to 3 substituents which are selected, independently of one another, from alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio and haloalkylthio, and where the amidic phenyl group may be condensed with a saturated 5-membered ring which may or may not be substituted by one or more alkyl groups and/or may have a hetero atom selected from O and S, and the active ingredient fenazaquin which is known as an acaricide.
These mixtures are described as being particularly effective against Botrytis.
EP-B 531,837, EP-A 645,091 and WO 97/06678 disclose fungicidal mixtures which contain one of the azoles II.1 to II.17 as an active ingredient component.
1-[(2RS,4RS;2RE,4SR)-4-bromo-2-(2,4-dichlorophenyl)tetra-hydrofuryl ]-1H-1,2,4-triazole (II.1)
2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol (II.2)
(±)-4-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-yl]phenyl 4-chlorophenyl ether (II.3)
(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)
(Z)-2-(1H-1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)-oxirane (II.5)
4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazolylmethyl)-butyronitrile (II.6)
3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)-quinazolin-4(3H)-one (II.7)
bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-ylmethyl)-silane (II.8)
(R,S)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-hexan-2-ol (II.9)
(1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (II.10)
N-propyl-N-[2-(2,4,
6
-trichlorophenoxy)ethyl]imidazol-1-carboxamide (II.11)
(±)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (II.12)
(R,S)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol (II.13)
(±)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazolyl)propyl 1,1,2,2-tetrafluoroethyl ether (II.14)
(E)-1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl ]-1H-imidazole (II.15)
(RS)-2,4′-difluoro-&agr;-(1H-1,2,4-triazol-1-ylmethyl)benzhydryl alcohol (II.16)
2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile (II.17)
The azole derivatives II, their preparation and their action against harmful fungi is known per se:
II.1: common name: bromuconazol, Proc. Br. Crop Prot. Conf.-Pests Dis., 5-6, 439 (1990);
II.2: common name: cyproconazol, U.S. Pat. No. 4,664,696;
II.3: common name: difenoconazol, GB-A 2,098,607;
II.4: common name: diniconazol, CAS RN [83657-24-3];
II.5: common name (proposed): epoxiconazol, EP-A 196 038;
II.6: common name: fenbuconazol (proposed), EP-A 251 775;
II.7: common name: fluquinconazol, Proc. Br. Crop Prot. Conf.-Pests Dis., 5-3, 411 (1992);
II.8: common name: flusilazol, Proc. Br. Crop Prot. Conf.-Pests Dis., 1, 413 (1984);
II.9: common name: hexaconazol, CAS RN [79983-71-4];
II.10: common name: metconazol, Proc. Br. Crop Prot. Conf.-Pests Dis., 5-4, 419 (1992);
II.11: common name: prochloraz, U.S. Pat. No. 3,991,071;
II.12: common name: propiconazol, GB-A 1,522,657;
II.13: common name: tebuconazol, U.S. Pat. No. 4,723,984;
II.14: common name: tetraconazol, Proc. Br. Crop Prot. Conf.-Pests Dis., 1, 49 (1988);
II.15: common name: triflumizol, JP-A 79/119,462
II.16: common name: flutriafol, CAS RN [76674-21-0]
II.17: common name: myclobutanil, CAS RN [88671-89-0].
It is an object of the present invention to provide other compositions for controlling harmful fungi and in particular for certain indications.
We have found that this object is achieved by a mixture which comprises as active ingredients amide compounds of the formula I defined at the outset and as further fungicidally active component a fungicidal active ingredient from the class of the azoles II.1 to II.17.
The mixtures according to the invention have synergistic action and are therefore particularly suitable for controlling harmful fungi and in particular powdery mildew fungi in vegetables and grapevines.
In the context of the present invention, halogen is fluorine, chlorine, bromine and iodine and is in particular fluorine, chlorine and bromine.
The term “alkyl” includes straight-chain and branched alkyl groups. These are preferably straight-chain or branched C
1
-C
12
-alkyl and in particular C
1
-C
6
-alkyl groups. Examples of alkyl groups are alkyl such as, in particular, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethyl-2-methylpropyl, n-heptyl, 1-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 1-propylbutyl, octyl, decyl, dodecyl.
Haloalkyl is an alkyl group as defined above which is partially or fully halogenated by one or more halogen atoms, in particular by fluorine and chlorine. Preferably, there are from 1 to 3 halogen atoms present, and the difluoromethyl or the trifluoromethyl group is particularly preferred.
The above statements for the alkyl group and the haloalkyl group apply in a corresponding manner to the alkyl and haloalkyl groups in alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl and alkylsulfonyl.
The alkenyl group includes straight-chain and branched alkenyl groups. These are preferably straight-chain or branched C
3
-C
12
-alkenyl groups and in particular C
3
-C
6
-alkenyl groups. Examples of alkenyl groups are 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dime-thyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl, in particular 2-propenyl, 2-butenyl, 3-methyl-2-butenyl and 3-methyl-2-pentenyl.
The alkenyl group may be partially or fully halogenated by one or more halogen atoms, in particular by fluorine and chlorine. Th
Ammermann Eberhard
Eicken Karl
Hampel Manfred
Lorenz Gisela
Schelberger Klaus
BASF - Aktiengesellschaft
Keil & Weinkauf
Robinson Allen J.
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