U.S. patent application number 14/799671 was filed with the patent office on 2015-11-05 for fungicidal mixtures based on prothioconazole and a strobilurin derivative.
This patent application is currently assigned to BASF SE. The applicant listed for this patent is BASF SE. Invention is credited to Eberhard AMMERMANN, Thomas CHRISTEN, Gisela LORENZ, Klaus SCHELBERGER, V. James SPADAFORA, Reinhard STIERL, Siegfried STRATHMANN.
Application Number | 20150313226 14/799671 |
Document ID | / |
Family ID | 27770913 |
Filed Date | 2015-11-05 |
United States Patent
Application |
20150313226 |
Kind Code |
A1 |
AMMERMANN; Eberhard ; et
al. |
November 5, 2015 |
FUNGICIDAL MIXTURES BASED ON PROTHIOCONAZOLE AND A STROBILURIN
DERIVATIVE
Abstract
Disclosed is a fungicidal mixture containing (1)
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydr-
o-[1,2,4]-triazole-3-thion of formula (I) or the salts or adducts
thereof, and at least one additional fungicidal compound or the
salts or adducts thereof, selected among picoxystrobin of formula
(III) and pyraclostrobin of formula (IV), in a synergistically
active quantity.
Inventors: |
AMMERMANN; Eberhard;
(Heppenheim, DE) ; STIERL; Reinhard; (Freinsheim,
DE) ; LORENZ; Gisela; (Neustadt, DE) ;
STRATHMANN; Siegfried; (Limburgerhof, DE) ;
SCHELBERGER; Klaus; (Gonnheim, DE) ; SPADAFORA; V.
James; (Sugar Land, TX) ; CHRISTEN; Thomas;
(Dannstadt-Schauernheim, DE) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
BASF SE |
Ludwigshafen |
|
DE |
|
|
Assignee: |
BASF SE
Ludwigshafen
DE
|
Family ID: |
27770913 |
Appl. No.: |
14/799671 |
Filed: |
July 15, 2015 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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10505440 |
Aug 24, 2004 |
|
|
|
PCT/EP03/01929 |
Feb 26, 2003 |
|
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14799671 |
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Current U.S.
Class: |
514/345 ;
514/384 |
Current CPC
Class: |
A01N 37/18 20130101;
A01N 47/24 20130101; A01N 43/40 20130101; A01N 43/653 20130101;
A01N 43/56 20130101; A01N 37/50 20130101; C07D 249/12 20130101;
A01N 43/653 20130101; A01N 47/24 20130101; A01N 43/40 20130101;
A01N 37/50 20130101; A01N 43/653 20130101; A01N 43/40 20130101;
A01N 47/24 20130101; A01N 37/50 20130101; A01N 37/52 20130101; A01N
43/653 20130101; A01N 2300/00 20130101 |
International
Class: |
A01N 43/653 20060101
A01N043/653; A01N 43/56 20060101 A01N043/56; C07D 249/12 20060101
C07D249/12; A01N 43/40 20060101 A01N043/40 |
Foreign Application Data
Date |
Code |
Application Number |
Mar 1, 2002 |
DE |
10208838.1 |
Claims
1. A synergistic fungicidal mixture, comprising (1)
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydr-
o-[1,2,4]-triazole-3-thione (prothioconazole) of the formula I or
its salts or adducts ##STR00014## and at least one further
fungicidal compound or its salts or adducts, selected from the
group consisting of: picoxystrobin of the formula III ##STR00015##
and pyraclostrobin of the formula IV ##STR00016## in a
synergistically effective amount, wherein the weight ratio of
prothioconazole of the formula I to the further fungicidal compound
is from 1:20 to 20:1.
2. The synergistic fungicidal mixture of claim 1, wherein
prothioconazole of the formula I and picoxystrobin of the formula
III are present in a weight ratio of from 1:20 to 20:1.
3. The synergistic fungicidal mixture of claim 1, wherein
prothioconazole of the formula I and pyraclostrobin of the formula
IV are present in a weight ratio of from 1:20 to 20:1.
4. A method for controlling harmful fungi, which comprises treating
the harmful fungi, their habitat or the plants, seeds, soils,
areas, materials or spaces to be kept free from them with an
anti-fungal effective amount of a compound of formula I
##STR00017## or a salt or adduct thereof and at least one of
compound selected from picoxystrobin of formula III ##STR00018## or
a salt or adduct thereof, or pyraclostrobin of formula IV
##STR00019## or a salt or adduct thereof.
5. The method of claim 4, wherein the compound of the formula I and
at least one compound of the formula III or IV are applied
simultaneously, that is together or separately, or in
succession.
6. A fungicidal composition, comprising the synergistic fungicidal
mixture as claimed in claim 1 and a solid or liquid carrier.
7. A method as claimed in claim 4, wherein the compounds are
applied to agricultural crop areas in a total amount of from 0.1 to
8 kg/ha.
8. A fungicidal kit for controlling harmful fungi comprising, in
separate containers, a compound of formula I ##STR00020## or a salt
or adduct thereof, and at least one compound of formula III or IV
picoxystrobin of the formula III ##STR00021## or a salt or adduct
thereof, or pyraclostrobin of the formula IV ##STR00022## or a salt
or adduct thereof.
9. A synergistic fungicidal mixture comprising
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydr-
o-[1,2,4]-triazole-3-thione (prothioconazole) of the formula I or
its salts or adducts ##STR00023## and pyraclostrobin of the formula
IV ##STR00024## or its salts or adducts in a synergistically
effective amount.
10. The synergistic fungicidal mixture of claim 1, wherein said
mixture consists of prothioconazole or its salts or adducts and
picoxystrobin or its salts or adducts.
11. The synergistic fungicidal mixture of claim 1, wherein said
mixture consists of prothioconazole or its salts or adducts and
pyraclostrobin or its salts or adducts.
12. The synergistic fungicidal mixture of claim 1, wherein the
combination of prothioconazole of the formula I and picoxystrobin
of the formula III is responsible for the synergistic fungicidal
effect of said mixture.
13. The synergistic fungicidal mixture of claim 1, wherein the
combination of prothioconazole of the formula I and pyraclostrobin
of the formula IV is responsible for the synergistic fungicidal
effect of said mixture.
Description
[0001] This application is a continuation of U.S. Ser. No.
10/505,440, filed Aug. 24, 2004, which is a 35 U.S.C. 371 National
Phase Entry Application from PCT/EP03/01929, filed Feb. 26, 2003,
which claims the benefit of German Patent Application No.
10208838.1 filed on Mar. 1, 2002, the disclosures of which are
incorporated herein in their entireties by reference.
[0002] The present invention relates to a fungicidal mixture,
comprising
(1)
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-di-
hydro-[1,2,4]-triazole-3-thione (prothioconazole) of the formula I
or its salts or adducts
##STR00001##
and at least one further fungicidal compound or its salts or
adducts, selected from the group consisting of (2) trifloxystrobin
of the formula II
##STR00002##
and (3) picoxystrobin of the formula III
##STR00003##
and (4) pyraclostrobin of the formula IV
##STR00004##
and (5) dimoxystrobin of the formula V
##STR00005##
and (6) a strobilurin derivative of the formula VI
##STR00006##
in a synergistically effective amount.
[0003] Moreover, the invention relates to a method for controlling
harmful fungi using mixtures of the compounds I with at least one
of the compounds II, III, IV, V or VI, and to the use of the
compounds I, II, III, IV, V and VI for preparing such mixtures, and
to compositions comprising such mixtures.
[0004] The compound of the formula I,
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydr-
o-[1,2,4]-triazole-3-thione (prothioconazole), has already been
disclosed in WO 96/16048.
[0005] A number of active compound combinations of prothioconazole
with a large number of other fungicidal compounds have been
disclosed in WO 98/47367.
[0006] Trifloxystrobin of the formula II and its use as crop
protection agent are described in EP-A-0 460 575.
[0007] Picoxystrobin has been disclosed in EP-A-0 326 330.
[0008] The strobilurin derivative of the formula IV is likewise
already known and has been described in EP-A-0 804 421.
[0009] The strobilurin derivative of the formula V has been
disclosed in EP-A-0 477 631.
[0010] Finally, the strobilurin derivative of the formula VI is
likewise known and has been described in EP-A-0 876 332.
[0011] It is an object of the present invention to provide mixtures
which have further improved activity against harmful fungi combined
with a reduced total amount of active compounds applied
(synergistic mixtures), with a view to reducing the application
rates and improving the activity spectrum of the known compounds I,
II, III, IV, V and VI.
[0012] We have found that this object is achieved by the mixture,
defined at the outset, of prothioconazole with at least one
strobilurin derivative. Moreover, we have found that applying the
compound I and at least one of the compounds II, III, IV, V or VI
simultaneously, i.e. together or separately, or applying the
compound I and at least one of the compounds II, III, IV, V or VI
in succession provides better control of harmful fungi than is
possible with the individual compounds alone.
[0013]
2-[2-(1-Chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4--
dihydro-[1,2,4]-triazole-3-thione of the formula I is known from WO
96-16 048. The compound can be present in the "thiono" form of the
formula
##STR00007##
or in the tautomeric "mercapto" form of the formula
##STR00008##
[0014] For the sake of simplicity, only the "thiono" form is shown
in each case.
[0015] Trifloxystrobin of the formula II
##STR00009##
is known from EP-A 0 460 572.
[0016] Picoxystrobin of the formula III
##STR00010##
is known from EP-A-0 326 330.
[0017] Pyraclostrobin of the formula IV
##STR00011##
is known from EP-A 0 804 421.
[0018] Dimoxystrobin of the formula V
##STR00012##
is known from EP-A 0 477 631.
[0019] The strobilurin derivative of the formula VI
##STR00013##
is known from EP-A 0 876 332.
[0020] Owing to the basic character of their nitrogen atoms, the
compounds I to VI are capable of forming salts or adducts with
inorganic or organic acids or with metal ions.
[0021] Examples of inorganic acids are hydrohalic acids, carbonic
acid, such as hydrogen fluoride, hydrogen chloride, hydrogen
bromide and hydrogen iodide, sulfuric acid, phosphoric acid and
nitric acid.
[0022] Suitable organic acids are, for example, formic acid,
carbonic acid and alkanoic acids, such as acetic acid,
trifluoroacetic acid, trichloroacetic acid and propionic acid, and
also glycolic acid, thiocyanic acid, lactic acid, succinic acid,
citric acid, benzoic acid, cinnamic acid, oxalic acid,
alkylsulfonic acids (sulfonic acids having straight-chain or
branched alkyl radicals of 1 to 20 carbon atoms), arylsulfonic
acids or aryldisulfonic acids (aromatic radicals, such as phenyl
and naphthyl, which carry one or two sulfonic acid groups),
alkylphosphonic acids (phosphonic acids having straight-chain or
branched alkyl radicals of 1 to 20 carbon atoms), arylphosphonic
acids or aryldiphosphonic acids (aromatic radicals, such as phenyl
and naphthyl, which carry one or two phosphonic acid radicals), it
being possible for the alkyl or aryl radicals to carry further
substituents, for example p-toluenesulfonic acid, salicylic acid,
p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic
acid, etc.
[0023] Suitable metal ions are in particular the ions of the
elements of the second main group, in particular calcium and
magnesium, of the third and fourth main group, in particular
aluminum, tin and lead, and of the first to eighth transition
group, in particular chromium, manganese, iron, cobalt, nickel,
copper, zinc and others. Particular preference is given to the
metal ions of the elements of the transition groups of the fourth
period. The metals can be present in the various valencies that
they can assume.
[0024] Preference is given to mixtures of prothioconazole with
trifloxystrobin of the formula II.
[0025] Preference is also given to mixtures of prothioconazole with
picoxystrobin of the formula III.
[0026] Preference is given to mixtures of prothioconazole with
pyraclostrobin of the formula IV.
[0027] Preference is furthermore also given to mixtures of
prothioconazole with dimoxystrobin of the formula V.
[0028] Preference is also given to mixtures of prothioconazole with
the strobilurin derivative of the formula VI.
[0029] Preference is also given to three-component mixtures of
prothioconazole with two of the abovementioned strobilurin
derivatives.
[0030] When preparing the mixtures, it is preferred to employ the
pure active compounds I, II, III, IV, V and VI, to which may be
added further active compounds against harmful fungi or other
pests, such as insects, arachnids or nematodes, or else herbicidal
or growth-regulating active compounds or fertilizers.
[0031] The mixtures of the compound I with at least one of the
compounds II, III, IV, V or VI or the compound I, used
simultaneously, jointly or separately, with at least one of the
compounds II, III, IV, V or VI exhibit outstanding activity against
a wide range of phytopathogenic fungi, in particular from the
classes of the Ascomycetes, Basidiomycetes, Phycomycetes and
Deuteromycetes. Some of them act systemically and can therefore
also be employed as folio- and soil-acting fungicides.
[0032] They are especially important for controlling a large number
of fungi in a variety of crop plants, such as cotton, vegetable
species (e.g. cucumbers, beans, tomatoes, potatoes and cucurbits),
barley, grass, oats, bananas, coffee, corn, fruit species, rice,
rye, soya, grapevine, wheat, ornamentals, sugar cane, and a variety
of seeds.
[0033] They are particularly suitable for controlling the following
phytopathogenic fungi: Blumeria graminis (powdery mildew) in
cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea in
cucurbits, Podosphaera leucotricha in apples, Uncinula necator in
grapevines, Puccinia species in cereals, Rhizoctonia species in
cotton, rice and lawns, Ustilago species in cereals and sugar cane,
Venturia inaequalis (scab) in apples, Helminthosporium species in
cereals, Septoria nodorum in wheat, Botrytis cinera (gray mold) in
strawberries, vegetables, ornamentals and grapevines, Cercospora
arachidicola in groundnuts, Pseudocercosporella herpotrichoides in
wheat and barley, Pyricularia oryzae in rice, Phytophthora
infestans in potatoes and tomatoes, Plasmopara viticola in
grapevines, Pseudoperonospora species in hops and cucumbers,
Alternaria species in vegetables and fruit, Mycosphaerella species
in bananas and Fusarium and Verticillium species.
[0034] They can furthermore be employed in the protection of
materials (e.g. the protection of wood), for example against
Paecilomyces variotii.
[0035] The compound I can be applied simultaneously, that is either
together or separately, or successively with at least one of the
compounds II, III, IV, V and VI, the sequence, in the case of
separate application, generally not having any effect on the result
of the control measures.
[0036] The compounds I and II are usually applied in a weight ratio
of from 20:1 to 1:20, in particular from 10:1 to 1:10, preferably
from 5:1 to 1:5.
[0037] The compounds I and III are usually applied in a weight
ratio of from 20:1 to 1:20, in particular from 10:1 to 1:10,
preferably from 5:1 to 1:5.
[0038] The compounds I and IV are usually applied in a weight ratio
of from 20:1 to 1:20, in particular from 10:1 to 1:10, preferably
from 5:1 to 1:5.
[0039] The compounds I and V are usually applied in a weight ratio
of from 20:1 to 1:20, in particular from 10:1 to 1:10, preferably
from 5:1 to 1:5.
[0040] The compounds I and VI are usually applied in a weight ratio
of from 20:1 to 1:20, in particular from 10:1 to 1:10, preferably
from 5:1 to 1:5.
[0041] Depending on the kind of effect desired, the application
rates of the mixtures according to the invention are, in particular
in agricultural crop areas, from 0.01 to 8 kg/ha, preferably from
0.1 to 5 kg/ha, in particular from 0.1 to 3.0 kg/ha.
[0042] The application rates for the compound I are from 0.01 to 1
kg/ha, preferably from 0.05 to 0.5 kg/ha, in particular from 0.05
to 0.3 kg/ha.
[0043] Correspondingly, in the case of the compound II, the
application rates are from 0.01 to 1 kg/ha, preferably from 0.02 to
0.5 kg/ha, in particular from 0.05 to 0.3 kg/ha.
[0044] Correspondingly, in the case of the compound III, the
application rates are from 0.01 to 1 kg/ha, preferably from 0.02 to
0.5 kg/ha, in particular from 0.05 to 0.3 kg/ha.
[0045] Correspondingly, in the case of the compound IV, the
application rates are from 0.01 to 1 kg/ha, preferably from 0.02 to
0.5 kg/ha, in particular from 0.05 to 0.3 kg/ha.
[0046] Correspondingly, in the case of the compound V, the
application rates are from 0.01 to 1 kg/ha, preferably from 0.02 to
0.5 kg/ha, in particular from 0.05 to 0.3 kg/ha.
[0047] Correspondingly, in the case of the compound VI, the
application rates are from 0.01 to 1 kg/ha, preferably from 0.02 to
0.5 kg/ha, in particular from 0.05 to 0.3 kg/ha.
[0048] For seed treatment, the application rates of the mixture are
generally from 0.001 to 250 g/kg of seed, preferably from 0.01 to
100 g/kg of seed, in particular from 0.01 to 50 g/kg.
[0049] If phytopathogenic harmful fungi are to be controlled, the
separate or joint application of the compound I with at least one
of the compounds II, III, IV, V and VI or of the mixtures of the
compound I with at least one of the compounds II, III, IV, V or VI
is effected by spraying or dusting the seeds, the plants or the
soils before or after sowing of the plants, or before or after
plant emergence.
[0050] The fungicidal synergistic mixtures according to the
invention or the compound I and at least one of the compounds II,
III, IV, V and VI can be formulated, for example, in the form of
ready-to-spray solutions, powders and suspensions or in the form of
highly concentrated aqueous, oily or other suspensions,
dispersions, emulsions, oil dispersions, pastes, dusts, materials
for broadcasting or granules, and applied by spraying, atomizing,
dusting, broadcasting or watering. The use form depends on the
intended purpose; in each case, it should ensure as fine and
uniform as possible a distribution of the mixture according to the
invention.
[0051] The formulations are prepared in a known manner, for example
by adding solvents and/or carriers. Usually, inert additives, such
as emulsifiers or dispersants, are added to the formulations.
[0052] Suitable surfactants are the alkali metal salts, alkaline
earth metal salts and ammonium salts of aromatic sulfonic acids,
for example ligno-, phenol-, naphthalene- and
dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and
alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol
sulfates, and salts of sulfated hexa-, hepta- and octadecanols, or
of fatty alcohol glycol ethers, condensates of sulfonated
naphthalene and its derivatives with formaldehyde, condensates of
naphthalene or of the naphthalenesulfonic acids with phenol and
formaldehyde, polyoxyethylene octylphenyl ether, ethoxylated
isooctyl-, octyl- or nonylphenol, alkylphenol or tributylphenyl
polyglycol ethers, alkylaryl polyether alcohols, isotridecyl
alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated
castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl
ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,
lignosulfite waste liquors or methylcellulose.
[0053] Powders, materials for broadcasting and dusts can be
prepared by mixing or jointly grinding the compound I and at least
one of the compounds II, III, IV, V and VI or the mixture of the
compound I with at least one compound II, III, IV, V or VI with a
solid carrier.
[0054] Granules (for example coated granules, impregnated granules
or homogeneous granules) are usually prepared by binding the active
compound, or active compounds, to a solid carrier.
[0055] Fillers or solid carriers are, for example, mineral earths
such as silica gel, silicas, silicates, talc, kaolin, limestone,
lime, chalk, bole, loess, clay, dolomite, diatomaceous earth,
calcium sulfate, magnesium sulfate, magnesium oxide, ground
synthetic materials, and also fertilizers, such as ammonium
sulfate, ammonium phosphate, ammonium nitrate, ureas, and products
of vegetable origin, such as cereal meal, tree bark meal, wood meal
and nutshell meal, cellulose powders or other solid carriers.
[0056] The formulations generally comprise from 0.1 to 95% by
weight, preferably from 0.5 to 90% by weight, of the compound I and
at least one of the compounds II, III, IV, V or VI or of the
mixture of the compound I with at least one compound II, III, IV, V
or VI. The active compounds are employed in a purity of from 90% to
100%, preferably 95% to 100% (according to NMR spectrum or
HPLC).
[0057] The compound I and at least one of the compounds II, III,
IV, V and VI or the mixtures or the corresponding formulations are
applied by treating the harmful fungi, their habitat, or the
plants, seeds, soils, areas, materials or spaces to be kept free
from them with a fungicidally effective amount of the mixture, or
of the compound I and at least one of the compounds II, III, IV, V
or VI in the case of separate application.
[0058] Application can be effected before or after infection by the
harmful fungi.
USE EXAMPLE
[0059] The synergistic activity of the mixtures according to the
invention could be demonstrated by the following experiments:
[0060] The active compounds, separately or together, were
formulated as a 10% emulsion in a mixture of 63% by weight of
cyclohexanone and 27% by weight of emulsifier, and diluted with
water to the desired concentration.
[0061] Evaluation was carried out by determining the infected leaf
areas in percent. These percentages were converted into efficacies.
The efficacy (W) was determined as follows using Abbot's
formula:
W=(1-.alpha./.beta.)100
.alpha. corresponds to the fungal infection of the treated plants
in % and .beta. corresponds to the fungal infection of the
untreated (control) plants in
[0062] An efficacy of 0 means that the infection level of the
treated plants corresponds to that of the untreated control plants;
an efficacy of 100 means that the treated plants were not
infected.
[0063] The expected efficacies of the mixtures of the active
compounds were determined using Colby's formula [R. S. Colby, Weeds
15, 20-22 (1967)] and compared with the observed efficacies.
E=x+y-xy/100 Colby's formula [0064] E expected efficacy, expressed
in % of the untreated control, when using the mixture of the active
compounds A and B at the concentrations a and b [0065] x efficacy,
expressed in % of the untreated control, when using the active
compound A at the concentration a [0066] y efficacy, expressed in %
of the untreated control, when using the active compound B at the
concentration b
Use Example 1
Activity Against Mildew of Wheat Caused by Erysiphe [Syn. Blumeria]
Graminis Forma Specialis. Tritici
[0067] Leaves of wheat seedlings of the cultivar "Kanzler" grown in
pots were sprayed to runoff point with an aqueous preparation of
active compound which had been prepared from a stock solution
comprising 10% of active compound, 85% of cyclohexanone and 5% of
emulsifier, and, 24 hours after the spray coating had dried on, the
leaves were dusted with spores of mildew of wheat (Erysiphe [syn.
Blumeria] graminis forma specialis. tritici). The test plants were
then placed in a greenhouse at 20-24.degree. C. and 60-90% relative
atmospheric humidity. After 7 days, the extent of the development
of the mildew was determined visually in % infection of the entire
leaf area.
[0068] The visually determined values for the percentage of
diseased leaf areas were converted into efficacies as % of the
untreated control. An efficacy of 0 means the same disease level as
in the untreated control, an efficacy of 100 means a disease level
of 0%. The expected efficacies for the active compound combinations
were determined using Colby's formula mentioned above and compared
with the observed efficacies.
TABLE-US-00001 TABLE 1 Concentration of active Efficacy in % of
compound in the spray the untreated Active compound liquor in ppm
control Control (untreated) (90% infected) 0 Compound I = 4 22
prothioconazole 1 0 0.25 0 0.06 0 0.015 0 Compound II = 4 83
trifloxystrobin 1 44 0.25 22 0.06 0 Compound III = 0.25 11
picoxystrobin Compound IV = 1 0 pyraclostrobin 0.25 0
TABLE-US-00002 TABLE 2 Combinations according to the Observed
Calculated invention efficacy efficacy*) Compound I =
prothioconazole + 33 22 Compound II = trifloxystrobin 0.015 + 0.25
ppm Mixture 1:16 Compound I = prothioconazole + 94 83 Compound II =
trifloxystrobin 1:4 ppm Mixture 1:4 Compound I = prothioconazole +
56 44 Compound II = trifloxystrobin 0.25 + 1 ppm Mixture 1:4
Compound I = prothioconazole + 22 0 Compound II = trifloxystrobin
0.25 + 0.06 ppm Mixture 4:1 Compound I = prothioconazole + 55 40
Compound II = trifloxystrobin 4 + 0.25 ppm Mixture 16:1 Compound I
= prothioconazole + 33 11 Compound III = picoxystrobin 0.06 + 0.25
ppm Mixture 1:4 Compound I = prothioconazole + 22 11 Compound III =
picoxystrobin 1 + 0.25 ppm Mixture 4:1 Compound I = prothioconazole
+ 33 0 Compound IV = pyraclostrobin 0.06 + 1 ppm Mixture 1:16
Compound I = prothioconazole + 33 0 Compound IV = pyraclostrobin
0.015 + 0.25 ppm Mixture 1:16 Compound I = prothioconazole + 33 0
Compound IV = pyraclostrobin 0.25 + 1 ppm Mixture 1:4 Compound I =
prothioconazole + 22 0 Compound IV = pyraclostrobin 0.06 + 0.25 ppm
Mixture 1:4 Compound I = prothioconazole + 33 22 Compound IV =
pyraclostrobin 4 + 1 ppm Mixture 4:1 *)efficacy calculated using
Colby's formula
[0069] The test results show that in all mixing ratios the observed
efficacy is higher than the efficacy calculated beforehand using
Colby's formula (from Synerg 171. XLS).
Use Example 2
Curative Activity Against Brown Rust of Wheat Caused by Puccinia
recondita
[0070] Leaves of wheat seedlings of the cultivar "Kanzler" grown in
pots were dusted with spores of brown rust (Puccinia recondita).
The pots were then placed in a chamber with high atmospheric
humidity (90-95%), at 20-22.degree. C. for 24 hours. During this
time, the spores germinated and the germinal tubes penetrated into
the leaf tissue. The next day, the infected plants were sprayed to
runoff point with an aqueous formulation of active compound
prepared from a stock solution comprising 10% of active compound,
85% of cyclohexanone and 5% of emulsifier. After the spray coating
had dried on, the test plants were cultivated in a greenhouse at
20-22.degree. C. and 65-70% relative atmospheric humidity for 7
days. Thereafter, the extent of the rust fungus development on the
leaves was determined.
[0071] The visually determined values for the percentage of
diseased leaf areas were converted into efficacies as % of the
untreated control. An efficacy of 0 means the same disease level as
in the untreated control, an efficacy of 100 means a disease level
of 0%. The expected efficacies for the combinations of active
compounds were determined using Colby's formula mentioned above and
compared with the observed efficacies.
TABLE-US-00003 TABLE 3 Concentration of active Efficacy in % of
compound in the spray the untreated Active compound liquor in ppm
control Control (untreated) (90% infected) 0 Compound I = 1 0
prothioconazole 0.25 0 0.015 0 0.006 0 Compound II = 0.25 0
trifloxystrobin 0.06 0
TABLE-US-00004 TABLE 4 Combinations according to the Observed
Calculated invention efficacy efficacy*) Compound I =
prothioconazole + 22 0 Compound II = trifloxystrobin 0.015 + 0.25
ppm Mixture 1:16 Compound I = prothioconazole + 22 0 Compound II =
trifloxystrobin 0.06:0.25 ppm Mixture 1:4 Compound I =
prothioconazole + 67 0 Compound II = trifloxystrobin 1 + 0.25 ppm
Mixture 4:1 Compound I = prothioconazole + 67 0 Compound II =
trifloxystrobin 0.25 + 0.06 ppm Mixture 4:1 Compound I =
prothioconazole + 11 0 Compound II = trifloxystrobin 1 + 0.06 ppm
Mixture 16:1 Compound I = prothioconazole + 44 33 Compound III =
picoxystrobin 0.06 + 1 ppm Mixture 1:16 Compound I =
prothioconazole + 11 0 Compound III = picoxystrobin 0.06 + 0.25 ppm
Mixture 1:4 Compound I = prothioconazole + 78 0 Compound III =
picoxystrobin 1 + 0.25 ppm Mixture 4:1 Compound I = prothioconazole
+ 78 0 Compound III = picoxystrobin 0.25 + 0.06 ppm Mixture 4:1
Compound I = prothioconazole + 44 0 Compound III = picoxystrobin 1
+ 0.06 ppm Mixture 16:1 Compound I = prothioconazole + 94 0
Compound IV = pyraclostrobin 0.015 + 0.25 ppm Mixture 1:16 Compound
I = prothioconazole + 89 0 Compound IV = pyraclostrobin 0.06 + 0.25
ppm Mixture 1:4 Compound I = prothioconazole + 22 0 Compound IV =
pyraclostrobin 1 + 0.25 ppm Mixture 4:1 Compound I =
prothioconazole + 22 0 Compound IV = pyraclostrobin 0.25 + 0.06 ppm
Mixture 4:1 Compound I = prothioconazole + 89 0 Compound IV =
pyraclostrobin 1 + 0.06 ppm Mixture 16:1 *)efficacy calculated
using Colby's formula
[0072] The test results show that in all mixing ratios the observed
efficacy is higher than the efficacy calculated beforehand using
Colby's formula (from Synerg 171. XLS).
* * * * *