Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-12-01
2002-04-09
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, C514S231200, C514S239500, C514S260100, C514S317000, C514S383000, C514S407000, C514S619000
Reexamination Certificate
active
06369090
ABSTRACT:
The present invention relates to a fungicidal mixture which comprises
a.1) a carbamate of the formula I.a,
in which X is CH or N, n is 0, 1 or 2 and R is halogen, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl, it being possible for the radicals R to be different if n is 2, or
a.2)the oxime ether carboxamide of the formula I.b
and
b.1) 4-[2-methyl-3-(4-tert-butylphenyl)propyl]-2,6-dimethylmorpholine
or
b.2) 4-(C
10
-C
13
-alkyl)-2,6-dimethylmorpholine
or
b.3) (RS)-1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine
and
c) an active ingredient from the group of the azole fungicides (III),
in a synergistically effective amount.
Particular preference is given to mixtures in which one of the compounds III.1 to III.33 serves as azole fungicide:
III.1 1-{[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-1H-1,2,4-triazole
III.2 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
III.3 1-[(2RS, 4RS; 2RS, 4SR)-4-bromo-2-(2,4-dichlorophenyl)tetrahydrofurfuryl]-1H-1,2,4-triazole
III.4 (2RS, 3RS, 2RS, 3SR)-2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
III.5 (2RS, 3RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pentan-3-ol
III.6 cis, trans-3-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-yl]phenyl 4-chlorophenyl ether
III.7 (E)-(R,S)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
III.8 (2RS, 3RS)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,4-triazole
III.9 (±)-1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole
III.10 (RS) -4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butyronitrile
III.11 3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one
III.12 bis-(4-fluorophenyl)(methyl)-(1H-1,2,4-triazol-1-ylmethyl)silane
III.13 (RS)-2,4′-difluoro-&agr;-(1H-1,2,4-triazol-1-ylmethyl)benzhydryl alcohol
III.14 (RS)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-hexan-2-ol
III.15 (1)-1-(&bgr;-allyloxy-2,4-dichlorophenylethyl)imidazole
III.16 4-chlorobenzyl N-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)thioacetamidate
III.17 (1RS,2SR,5RS; 1RS,2SR,5SR) -2-(4-chlorobenzyl)-5-isopropyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol
III.18 (1RS,5RS; 1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol
III.19 2-(4-chlorophenyl)-2-cyano-1-(1H-1,2,4-triazol-1-yl)-hexane
III.20 2-(4-chlorophenyl)-3-hydroxy-4,4-dimethyl-1-(1H-1,2,4-triazol-1-yl)pentane
III.21 pent-4-enyl N-furfuryl-N-imidazol-1-ylcarbonyl-DL-homoalaninate
III.22 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)pentane
III.23 N-propyl-N-[(2,4,6-trichlorophenoxy)ethyl]imidazole-1-carboxamide
III.24 (±)-1-{[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl}-1H-1,2,4-triazole
III.25 3-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-one
III.26 (±)-cis)-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol
III.27 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1yl)pentan-3-ol
III.28 (RS)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propyl 1,1,2,2-tetrafluoroethyl ether
III.29 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one
III.30 (1RS,2RS; 1RS,2SR) 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
III.31 (E)-4-chloro-&agr;,&agr;,&agr;-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylidene)-o-toluidine
III.32 (±)-(E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol
III.33 (E)-(RS)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol
Moreover, the invention relates to methods for controlling harmful fungi using mixtures of the compounds I (I.a and I.b), II (II.a, II.b and II.c) and III (III.1-III.33).
The compounds of the formula I, their preparation and their activity against harmful fungi are disclosed in the literature (EP-A 477 631; WO-A 96/01,256; WO-A 96/01,258).
Also known are the compounds of the formula II:
II.a (common name: fenpropimorph): CAS RN [67564-91-4], U.S. Pat. No. 4,202,894;
II.b (common name: tridemorph): CAS RN [81412-43-3], DE-A 11 64 152;
II.c (common name: fenpropidin): CAS RN [67306-00-7], U.S. Pat. No. 4,202,894.
In addition, the compounds III are described in the literature as active compounds for controlling harmful fungi:
III.1 (common name: azaconazole): CAS RN [60207-31-0];
III.2 (common name: biteranol): CAS RN [70585-36-3], DE-A 23 24 010;
III.3 (common name: bromuconazole): CAS RN [116255-48-2];
III.4 (common name: cyproconazole): CAS RN [94361-06-5], U.S. Pat. No. 4,664,696;
III.5 (common name: diclobutrazol): CAS RN [75736-33-3];
III.6 (common name: difenconazole): CAS RN [119446-68-3], EP-A 65 485;
III.7 (common name: diniconazole): CAS RN [83657-24-3];
III.8 (proposed common name: epoxiconazole): CAS RN [106325-08-0];
III.9 (common name: etaconazole): CAS RN [60207-93-4];
III.10 (common name: fenbuconazole): CAS RN [114369-43-6];
III.11 (common name: fluquinconazole): CAS RN [136426-54-5];
III.12 (common name: flusilazole): CAS RN [85509-19-9];
III.13 (common name: flutriafol): CAS RN [76674-21-0], EP-A 15 756;
III.14 (common name: hexaconazole): CAS RN [79983-71-4];
III.15 (common name: imazalil): CAS RN [73790-28-0];
III.16 (common name: imibenzconazole): CAS RN [86598-92-7];
III.17 (common name: ipconazole): CAS RN [125225-28-7], EP-A 267 778;
III.18 (common name: metconazole): CAS RN [125116-23-6];
III.19 (common name: myclobutanil): CAS RN [88671-89-0];
III.20 (common name: paclobutrazol): CAS RN [76738-62-0], U.S. Pat. No. 1,595,697;
III.21 (common name: pefurazoate): CAS RN [101903-30-4];
III.22 (common name: penconazole): CAS RN [66246-88-6], GB-A 1 589 852;
III.23 (common name: prochloraz): CAS RN [67747-09-5], U.S. Pat. No. 4,080,462;
III.24 (common name: propiconazole): CAS RN [60207-90-1], GB-A 1 522 657;
III.25 (common name: quinconazole): CAS RN [103970-75-8];
III.26 (code name: SSF 109): CAS RN [129586-32-9];
III.27 (common name: tebuconazole): CAS RN [107534-96-3], EP-A 40 345;
III.28 (common name: tetraconazole): CAS RN [112281-77-3], EP-A 234 242;
III.29 (common name: triadimefon): CAS RN [43121-43-3], U.S. Pat. No. 3,912,752;
III.30 (common name: triadimenol): CAS RN [55219-65-3], DE-A 23 24 010;
III.31 (common name: triflumizole): CAS RN [99387-89-0], JP-A 79/119,462;
III.32 (common name: triticonazole): CAS RN [131983-72-7];
III.33 (common name: uniconazole): CAS RN [83657-22-1].
Synergistic mixtures of the compounds I.a with active compounds II.a to II.c are described in the earlier application DE P 19 616 724.8, and synergistic mixtures of the compounds I.a with active compounds III.1 to III.33 are described in the earlier application DE P 19 618 676.5.
Moreover, EP-A 645 087 discloses synergistic mixtures of the compound I.b with the active compounds II.a to II.c, and EP-A 645 091 discloses synergistic mixtures of the compound I.b with some of the active compounds III.1 to III.33.
It is an object of the present invention to provide mixtures which have an improved activity against harmful fungi combined with a reduced total amount of active ingredients applied (synergistic mixtures), with a view to reducing the application rates and to improving the activity spectrum of the known compounds I, II and III.
We have found that this object is achieved by the mixture defined at the outset. Moreover, we have found that better control of harmful fungi is possible by applying the compounds I, II and III simultaneously, that is either together or separately, or by applying the compounds I, II and III in succession than wh
Ammermann Eberhard
Birner Erich
Hampel Manfred
Leyendecker Joachim
Lorenz Gisela
BASF - Aktiengesellschaft
Keil & Weinkauf
Robinson Allen J.
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