Note: Descriptions are shown in the official language in which they were submitted.
CA 02568817 2006-11-29
1
USE OF (E)-5-(4-CHLORBENZYLIDEN) 2,2-DIMETHYL-1-(1H-1,2,4-TRIAZOL-
1-YLMETHYL)CYCLOPENTANOL FOR COMBATING RUST
ATTACKS ON SOYA PLANTS
The invention relates to the use of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-
(1H-
1,2,4-triazol-1-ylmethyl)cyclopentanol for controlling rust disease on soybean
plants.
Until recently, the main growing areas for soybean cultures were free from
diseases
caused by harmful fungi, such as rust, which were of economical importance.
However,
in 2001 and 2002, South America saw increasingly serious rust diseases in
soybean
cultures caused by the harmful fungi Phakopsora pachyrhizi and Phakopsora
meibomiae. The results were considerable harvest and yield losses.
Most current fungicides are not suitable for controlling rust diseases in
soybean
cultures because they do not sufficiently inhibit the multiplication of the
harmful fungi
which cause the rust disease, such as Phakopsora pachyrhizi and Phakopsora
meibomiae. Moreover, there is a risk of the fungicidal active ingredient
adversely
affecting the symbiosis of root nodule bacteria (Rhizobium and
Bradyrrhizobium) and
soybean plants, thus causing yield loss.
CA 2,437;183 describes the use of strobilurins for the treatment of rust
diseases on
legumes.
However, there is a basic need for providing further active ingredients
against certain
fungal diseases to avoid the development of resistance.
It was therefore an object to provide a further agent which makes possible an
effective
control of rust diseases on soybean plants. In particular, the agent should
have no
adverse effect on the symbiosis of root nodule bacteria and soybean plants.
Surprisingly, it has now been found that (E)-5-(4-chlorobenzylidene)-2,2-
dimethyl-1-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol efficiently inhibits the
multiplication of the
abovementioned harmful fungi and is thus suitable for controlling the rust
disease on
soybean plants which is caused by these harmful fungi.
The invention therefore relates to the use of (E)-5-(4-chlorobenzylidene)-2,2-
dimethyl-
1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol for controlling rust disease on
soybean
plants and to a method for controlling rust disease on these plants in which
the plant
which requires such a treatment, or parts of this plant or the soil which is
intended for
culturing or growing the plant, is treated with (E)-5-(4-chlorobenzylidene)-
2,2-dimethyl-
1-(1 H-1,2,4-triazol-1-ylmethyl)cyclopentanol.
PF 0000055665 CA 02568817 2006-11-29
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The use of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-yl-
methyl)cyclopentanol efficiently prevents infection of the soybean plants with
rust
disease (protective treatment) and, moreover, also leads to a cure for plants
which are
already diseased (curative treatment).
Surprisingly, rust disease of soybean plants can also be prevented efficiently
by
treating the seed with (E)-5-(4-chlorobenzyiidene)-2,2-dimethyl-1-(1H-1,2,4-
triazol-1-yl-
methyl)cyclopentanol .
Moreover, it has unexpectedly emerged that the symbiosis of the root nodule
bacteria
with the soybean plants is not, or at least not substantially, adversely
affected by the
application of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1 H-1,2,4-triazol-1-
yl-
methyl)cyclopentanol.
Both the racemate of (E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1 H-1,2,4-
triazol-1-yl-
methyl)cyclopentanol and its enantiomers and nonracemic mixtures of these
enantiomers are suitable in accordance with the invention. (E)-5-(4-
Chlorobenzyl idene)-2,2-dim ethyl- 1 -(1 H- 1,2,4-triazol-1 -yl m
ethyl)cyclopentanol is known
to the skilled worker under the name triticonazole and commercially available.
The term "plant parts" here and hereinbelow refers not only to the aerial
plant parts
such as foliage, but also to the subterranean plant parts, i.e. the root
system, and to the
fruits and seeds.
To control the rust disease, the soybean plants, or the plant parts to be
protected from
rust disease, or the soil, are treated with such an amount of an active
ingredient
preparation comprising triticonazole as is necessary for controlling the rust
disease.
The way in which the active ingredient preparation is applied depends in a
known
manner on the intended use and the type of application. Expediently, the type
of active
ingredient preparation is chosen in such a way that a fine and uniform
distribution of
the active ingredient(s) is ensured.
In a first preferred embodiment of the invention, the aerial plant parts of
the soybean
plants, in particular the leaves, are treated with a suitable preparation of
the active
ingredient. Preferably, triticonazole is employed in an aqueous spray mixture.
As a rule, the triticonazole application rates required for protective
treatment of the
aerial plant parts amount to 10 to 1000 g/ha, in particular to 20 to 500 g/ha.
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As a rule, the triticonazole application rates required for curative treatment
of the aerial
plant parts amount to 10 to 1000 g/ha, in particular to 20 to 500 g/ha.
In another embodiment of the invention, the seed is treated with a preparation
of the
active ingredient which is suitable for seed treatment. Active ingredient
preparations for
seed treatment are, in particular, aqueous spray mixtures, ready-to-use dusts
and ULV
solutions. In the case of seed treatment, triticonazole is generally employed
in an
amount of from 1 to 500 g, preferably 10 to 200 g, per 100 kilograms of seed.
Moreover, other harmful fungi which are frequently found in soybean plants can
also be
controlled very effectively with the method according to the invention. The
most
important fungal diseases in soybeans are listed hereinbelow:
= damping-off caused by Rhizoctonia solani,
= stem rot caused by Fusarium solani,
= stem rot caused by Fusarium spp.,
= stem and pod blight caused by Phomopsis phaseoli + spp.,
= purple blotch caused by Cercospora kikuchi,
= frogeye leaf spot caused by Cercospora sojina,
= seedling blight caused by Pythium spp.,
= stem antrachnose caused by Colletotrichum demativum var. truncata,
= brown spot caused by Septoria glycines,
= leaf spot caused by Cercospora spp.,
= powdery mildew caused by Erysiphe polygoni.
To widen the spectrum of action, triticonazole can also be employed together
with other
active ingredients which are used in soybean growing, for example together
with
herbicides, insecticides, nematicides, growth regulators, fungicides or else
fertilizers.
The following list of active ingredients with which triticonazole can be used
in
accordance with the invention is intended to illustrate the possible
combinations, but
not to impose any limitation:
Fungicides:
= acylalanines, in particular oxadixyl;
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= amine derivatives, in particular guazatine, iminoctadine;
= azoles, in particular difenoconazole, epoxyconazole, fenbuconazole,
fluquiconazole, flusilazol, flutriafol, hexaconazole, imazalil, metconazole,
myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole,
tebuconazole;
= dicarboximides such as iprodion, procymidon, vinclozolin;
= heterocylic compounds such as anilazin, benomyl, boscalid, carbendazim,
carboxin, oxycarboxin, cyazofamid, dithianon, famoxadon, fenamidon, fenarimol,
fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol,
probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen, silthiofam,
thiabendazole, thifluzamid, thiophanate-methyl, tiadinil, tricyclazol,
triforine;
= nitrophenyl derivatives such as binapacryl, dinocap, dinobuton, nitrophthal-
isopropyl;
= phenylpyrroles such as fenpiclonil or fludioxonil;
= sulfur;
= other fungicides such as acibenzolar-S-methyl, benthiavalicarb, carp
ropamid,
chlorothalonil, cyflufenamid, cymoxanil, dazomet, diclomezin, diclocymet,
diethofencarb, edifenphos, ethaboxam, fenhexamid, fentin-acetate, fenoxanil,
ferimzone, fluazinam, fosetyl, fosetyl aluminum, iprovalicarb, hexachlorobe
nzene,
metrafenon, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintozene,
zoxamid;
= strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-
methyl,
metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or
trifloxystrobin;
= sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet,
tolylfluanid
cinnamamides and analogs such as dimethomorph, flumetover or flumorph.
I nsecticides/acaricides:
= organo(thio)phosphates, in particular acephate;
= carbamates, in particular alanycarb, benfuracarb, bendiocarb, carbosulfan,
fenoxycarb, furathiocarb, methiocarb, methomyl, thiodicarb, triazamate;
= pyrethroids such as allethrin, bifenthrin, cyfluthrin, cyphenothrin,
cypermethrin and
the alpha-, beta-, theta- and zeta isomers, deltamethrin, esfenvalerate,
ethofenprox, fenpropathrin, fenvalerate, cyhalothrin, lambda-cyhalothrin,
imiprothrin, permethrin, prallethrin, pyrethrin I, pyrethrin II, silafluofen,
tau-
fluvalinate, tefluthrin, tetramethrin, tralomethrin, transfluthrin, zeta-
cypermethrin;
= neonicotinoids such as flonicamid, clothianidin, dinotefuran, imidacloprid,
thiamethoxam, nitenpyram, nithiazin, acetamiprid, thiacloprid;
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= pyrazole insecticides such as acetoprole, ethiprole, fipronil, tebufenpyrad,
tolfenpyrad and vaniliprole;
= and also spinosad and thiamethoxam.
Growth regulators such as chlormethquat and mepiquat.
Mixtures of triticonazole with a further fungicide from the azole fungicide
group have
proved to be very especially suitable for the use according to the invention.
Preferred
azole fungicides are epoxyconazole, tebuconazole, fluquinconazole, flutriafol,
metconazole, myclobutanil, cycproconazole, prothioconazole and propiconazole.
By
applying triticonazole jointly with a further azole fungicide, an increased
activity is
obtained so that in total lower application rates of fungicides are required
for obtaining
the desired fungicidal effect.
If triticonazole is employed together with an azole fungicide, the active
ingredients will
preferably be employed in a triticonazole to azole fungicide weight ratio of
from 1:100
to 100:1 and in particular 1:20 to 20:1. In this case, the application rates
of further azole
fungicide preferably amount to from I to 500 g/ha and in particular to 5 to
300 -g/ha.
Likewise especially suitable for the use according to the invention are
mixtures of
triticonazole with at least one further fungicide from the strobilurin group
which is
selected from among trifloxystrobin, pyraclostrobin, orysastrobin,
fluoxastrobin and
azoxystrobin.
If triticonazole is employed together with one of the abovementioned
strobilurins, the
active ingredients will preferably be employed in a triticonazole to
strobilurin weight
ratio of from 1:100 to 100:1 and in particular 1:20 to 20:1. In this case, the
application
rates of strobilurin preferably amount to from 1 to 500 -g/ha and in
particular to 5 to 300
-g/ha.
If triticonazole is employed jointly with a further fungicidal active
ingredient, the latter
can be applied simultaneously with triticonazole or after a short time
interval, for
example within a few days before or after the triticonazole treatment. In the
case of
simultaneous application, the treatment of the soybean plant can be effected
in one
pass where a composition comprising triticonazole and the further fungicidal
active
ingredient are applied, or else in separate passes where different
compositions of the
individual active ingredients are applied.
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It has furthermore been proved to be particularly advantageous to employ
triticonazole
together with at least one active ingredient against stinging or sucking
insects and
other arthropods, for example of the order
= Coleoptera, in particular Phyllophaga sp. such as Phyllophaga cuyabana,
Sternechus sp. such as Sternechus pingusi, Sternechuns subsignatus,
Promecops sp. such as Promecops carinicollis, Aracanthus sp. such as
Aracanthus morei, and Diabrotica sp. such as Diabrotica speciosa, Diabrotica
longicornis, Diabrotica 12-punctata, Diabrotica virgifera,
= Lepidoptera in particular Elasmopalpus sp. such as Elasmopalpus lignosellus,
= Isoptera, in particular Rhinotermitida,
= Homoptera, in particular Dalbulus maidis
or against nematodes, including root knot nematodes, for example Meloidogyne
spp.
such as Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and
other
Meloidogyne species; cyst-forming nematodes such as Globodera rostochiensis
and
other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera
schachtii, Heterodera trifolii, and other Heterodera species; gall nematodes,
for
example Anguina species; stem eel worms and foliar nematodes such as
Aphelenchoides species.
In particular, it has proved useful to employ triticonazole together with at
least one
insecticide from the neonicotinoid group, specifically with imidacloprid,
thiametoxam or
clothiamidin, or an insecticide from the group of the pyrazole insecticides,
specifically
with fipronil.
In particular, it has proved useful to employ triticonazole together with an
insecticide, in
particular a neonicotinoid or pyrazole insecticide, for the treatment of seed
or the
treatment of seedlings of the soybean plants.
If triticonazole is employed jointly with a further insecticidal active
ingredient, the latter
can be applied simultaneously with triticonazole or after a short time
interval, for
example within a few days before or after the triticonazole treatment. In the
case of
simultaneous application, the treatment of the soybean plant can be effected
in one
pass where a composition comprising triticonazole and the further insecticidal
active
ingredient are applied, or else in separate passes where different
compositions of the
individual active ingredients are applied.
Since triticonazole has no adverse effect on the symbiosis of the root nodule
bacteria
and the soybean plants, the treatment of the seed with the active ingredient
can be
carried out simultaneously or within a narrow time interval around the
infection of the
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seed with the root nodule bacteria. For example, the active ingredient can be
applied to
the seed jointly with a suitable preparation of the root nodule bacteria, for
example an
aqueous suspension of the root nodule bacteria.
Triticonazole and optionally the further active ingredient(s) can be used as
such, in the
form of their formulations or the use forms prepared therefrom, for example in
the form
of directly sprayable solutions, powders, suspensions or dispersions,
emulsions, oil
dispersions, pastes, dusts, compositions for broadcasting, or granules.
Application is
typically achieved by means of spraying, atomizing, dusting, broadcasting or
pouring.
In any case, the use forms and means should ensure the finest possible
distribution of
the active ingredients according to the invention.
Aqueous use forms of the active ingredients can be prepared from commercially
available formulations of the active ingredients, for example from emulsion
concentrates, pastes or wettable powders (sprayable powders, oil dispersions),
by
addition of water. To prepare emulsions, pastes or oil dispersions, the
substances, as
such or dissolved in an oil or solvent, can be homogenized in water by means
of
wetter, sticker, dispersant or emulsifier. However, it is also possible to
prepare
concentrates which consist of active substance, wetter, sticker, dispersant or
emulsifier
and, if appropriate, solvent or oil, and such concentrates are suitable for
dilution with
water.
The concentration of triticonazole and the optional further active
ingredient(s) in the
ready-to-use preparations can vary within substantial ranges. In general, they
are
between 0.0001 and 10%, preferably between 0.001 and 1% (% by weight total
active
ingredients, based on the total weight of the ready-to-use formulation).
Triticonazole and the optional further active ingredient(s) can also be used
successfully
in the ultra-low-volume method (ULV), it being possible to apply formulations
comprising more than 95% by weight of active ingredient, or indeed the active
ingredient without additives.
Various types of oils or wetters, adjuvants, herbicides, fungicides,
insecticides,
nematicides, but also other pesticides, for example bactericides, can be added
to the
active ingredients, if appropriate also immediately prior to application (tank
mix). These
agents can be admixed to the compositions according to the invention in a
weight ratio
of from 1:10 to 10:1.
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The formulations are prepared in the known manner, for example by extending
the
active ingredient with solvents and/or carriers, if appropriate using
surfactants, i.e.
emulsifiers and/or dispersants.
Solvents/carriers which are suitable are essentially:
- water, aromatic solvents (e.g. Solvesso products, xylene), paraffins (for
example
mineral oil fractions), alcohols (for example methanol, butanol, pentanol,
benzyl
alcohol), ketones (for example cyclohexanone, methyl hydroxybutyl ketone,
diacetone alcohol, mesityl oxide, isophorone), lactones (for example gamma-
butyrolactone), pyrrolidones (pyrrolidone, N-methylpyrrolidone, N-
ethylpyrrolidone,
n-octylpyrrolidone), acetates (glycol diacetate), glycols, dimethyl fatty acid
amides,
fatty acids and fatty acid esters. In principle, solvent mixtures may also be
used.
- Carriers such as ground natural minerals (for example kaolins, clays, talc,
chalk)
and ground synthetic minerals (for example highly-disperse silica, silicates);
emulsifiers such as nonionic and anionic emulsifiers (for example
polyoxyethylene
fatty alcohol ethers, alkylsulfonates and arylsulfonates), and dispersants
such as
lignin-sulfite waste liquors and methylcellulose.
Suitable surfactants are alkali metal salts, alkaline earth metal salts and
ammonium
salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid,
dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates,
alkylsulfonates, fatty
alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers,
furthermore
condensates of sulfonated naphthalene and naphthalene derivatives with
formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with
phenol
and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated
isooctylphenol,
octylphenol, nonylphenol, alkylphenyl polyglycol ether, tributylphenyl
polyglycol ether,
tristerylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and
fatty alcohol
ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl
ethers,
ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol
esters,
lignin-sulfite waste liquors and methylcellulose.
Suitable for the preparation of directly sprayable solutions, emulsions,
pastes or oil
dispersions are mineral oil fractions of medium to high boiling point, such as
kerosene
or diesel oil, furthermore coal tar oils and oils of vegetable and animal
origin, aliphatic,
cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin,
tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol,
ethanol,
propanol, butanol, cyclohexanol, cyclohexanone, mesityl oxide, isophorone,
strongly
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polar solvents, for example dimethyl sulfoxide, 2-pyrrolidone, N-
methylpyrrolidone,
butyrolactone, or water.
Powders, materials for spreading and dusts can be prepared by mixing or
jointly
grinding the active substances with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous
granules, can be prepared by binding the active ingredients onto solid
carriers. Solid
carriers are, for example, mineral earths such as silica gels, silicates,
talc, kaolin,
Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous
earth,
calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic
materials,
fertilizers such as, for example, ammonium sulfate, ammonium phosphate,
ammonium
nitrate, ureas and plant products such as cereal meal, tree bark meal, wood
meal and
nutshell meal, cellulose powder and other solid carriers.
In general, the formulations comprise between 0.01 and 95% by weight,
preferably
between 0.1 and 90% by weight, in particular from 5 to 50 % by weight, of the
active
ingredient. In this context, the active ingredients are employed in a purity
of from 90%
to 100%, preferably 95% to 100% (according to NMR spectrum).
Examples of formulations are:
1. Products for dilution in water
A) Water-soluble concentrates (SL)
10 parts by weight of triticonazole are dissolved in water or a water-soluble
solvent. Alternatively, wetters or other adjuvants are added. Upon dilution in
water, the active ingredient dissolves.
B) Dispersible concentrates (DC)
20 parts by weight of triticonazole are dissolved in cyclohexanone with
addition
of a dispersant, for example polyvinylpyrrolidone. Upon dilution in water, a
dispersion results.
C) Emulsifiable concentrates (EC)
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parts by weight of triticonazole are dissolved in xylene with addition of
calcium
dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). Upon
dilution in water, an emulsion results.
5 D) Emulsions (EW, EO)
40 parts by weight of triticonazole are dissolved in xylene with addition of
calcium
dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%). This
mixture is introduced into water by means of an emulsifier (Ultraturrax) and
made
into a homogeneous emulsion. Upon dilution in water, an emulsion results.
E) Suspensions (SC, OD)
parts by weight of triticonazole are comminuted in a stirred ball mill with
addition of dispersants, wetters and water or an organic solvent to give a
fine
suspension of active ingredient. Upon dilution in water, a stable suspension
of
15 the active ingredient results.
F) Water-dispersible and water-soluble granules (WG, SG)
50 parts by weight of triticonazole are ground finely with addition of
dispersant
and wetters and made into water-dispersible or water-soluble granules by means
20 of technical apparatuses (for example extrusion, spray tower, fluidized
bed).
Upon dilution in water, a stable dispersion or solution of the active
ingredient
results.
G) Water-dispersible and water-soluble powders (WP, SP)
75 parts by weight of triticonazole are ground in a rotor-stator mill with
addition of
dispersants, wetters and silica gel. Upon dilution in water, a stable
dispersion or
solution of the active ingredient results.
2. Products for direct application
H) Dusts (DP)
5 parts by weight of triticonazole are ground finely and mixed intimately with
95%
finely particulate kaolin. This gives a dust.
I) Granules (GR, FG, GG, MG)
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0.5 part by weight of triticonazole is ground finely and combined with 95.5%
carriers. Current methods are extrusion, spray drying or the fluidized bed.
This
gives granules for direct application.
J) ULV solutions (UL)
parts by weight of triticonazole are dissolved in an organic solvent, for
example xylene. This gives a product for direct application.
Compositions which are useful for seed treatment are e.g.:
10 A Soluble concentrates (SL, LS)
D Emulsions (EW, EO, ES)
E Suspensions (SC, OD, FS)
F Water-dispersible granules and water-soluble granules (WG, SG)
G Water-dispersible powders and water-soluble powders (WP, SP, WS)
H Dusts and dustable powders (DP, DS)
Preferred FS formulations of triticonazole for seed treatment usually comprise
from 0.5
to 80% of the active ingredient, from 0,05 to 5 /a of a wetter, from 0.5 to 15
% of a dis-
persing agent, from 0,1 to 5 % of a thickener, from 5 to 20 % of an anti-
freeze agent,
from 0,1 to 2 % of an anti-foam agent, from 1 to 20 % of a pigment and/or a
dye, from 0
to 15 % of a sticker /adhesion agent, from 0 to 75 % of a filler/vehicle, and
from 0,01 to
1 % of a preservative.
Suitable pigments or dyes for seed treatment formulations of triticonazole are
pigment
blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment
blue 80,
pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2,
pigment red
48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange
34, pig-
ment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment
brown
25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14,
acid blue 9,
acid yellow 23, basic red 10, basic red 108.
Wetters and dispersants, which are suitable are in particular the
aforementioned sur-
factants. Preferred wetting agents are alkylnaphthaline sulfonates such as
diisopropyl-
or diisobutylnaphthalenesulfonates. Preferred dispersants are nonionic or
anionic dis-
persants or mixtures of nonionic or anionic dispersants. Suitable nonionic
dispersants
which are employed are, in particular, ethylene oxide/propylene oxide block
polymers,
alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers, for
example poly-
oxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol,
nonylphenol,
alkylphenol polyglycol ether, tributylphenyl polyglycol ether, tristerylphenyl
polyglycol
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ether, alkylarylpolyether alcohols, alcohol and fatty alcohol ethylene oxide
conden-
sates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated
polyoxy-
propylene, lauryl alcohol polyglycol ether acetal, sorbitol esters and methyl
cellulose.
Suitable anionic dispersants which are used are, in particular, alkali metal,
alkaline
earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic
acid, phe-
nolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl
sulfates,
alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty
alcohol glycol
ethers, furthermore arylsulfonate/formaldehyde condensates, for example
condensates
of sulfonated naphthalene and naphthalene derivatives with formaldehyde,
conden-
sates of naphthalene or of naphtalenesulfonic acid with phenol and
formaldehyde, lign-
insulfonates, lignin-sulfite waste liquors, phosphated or sulfated derivatives
of methyl-
cellulose, and salts of polyacrylic acid.
Antifreeze which can be employed are in principle all those substances which
lead to a
depression of the melting point of water. Suitable antifreeze comprise
alkanoles such
as methanol, ethanol, isopropanol, butanols, glycol, glycerine,
diethylenglycol and the
like.
Thickeners which are suitable are all substances which can be employed for
such pur-
poses in agrochemical compositions, for example cellulose derivatives,
polyacrylic acid
derivatives, xanthan, modified clays and highly-dispersed silicas.
Antifoams which can be employed are all those substances which inhibit the
develop-
ment of foam and which are conventionally used for formulating agrochemical
active
ingredients. Silicone antifoams and magnesium stearate are particularly
suitable.
Preservatives which can be employed are all preservatives used for such
purposes in
agrochemical compositions. Examples which may be mentioned are dichlorophene,
isothiazolenes such as 1,2-benzisothiazol-3(2H)-one, 2-methyl-2H-isothiazol-3-
one-
hydrochloride, 5-chloro-2-(4-chlorobenzyl)-3(2H)-isothiazolone, 5-chloro-2-
methyl-2H-
isothiazol-3-one, 5-chloro-2-methyl-2H-isothiazol-3-one, 5-chloro-2-methyl-2H-
isothiazol-3-one-hydrochloride, 4,5-dichloro-2-cyclohexyl-4-isothiazolin-3-
one, 4,5-
dichloro-2-octyl-2H-isothiazol-3-one, 2-methyl-2H-isothiazol-3-one, 2-methyl-
2H-
isothiazol-3-one-calcium chloride complex, 2-octyl-2H-isothiazol-3-one and
benzyl al-
cohol hemiformal.
Stickers/adhesion agents are added to improve the adhesion of the active
materials on
the seeds after treatment. Suitable adhesives are block copolymers EO/PO
surfactants
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but also polyvinylalcohols, polyvinylpyrrolidones, polyacrylates,
polymethacrylates,
polybutenes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneam
ides,
polyethyleneimines (Lupasol , Polymin ), polyethers and copolymers derived
from
these polymers.
In principle, all customary methods of treating or dressing seeds can be
employed.
Specifically, the treatment follows a procedure in which the seed is mixed
with the spe-
cifically desired amount of seed dressing formulations, either as such or
after previ-
ously diluting them with water, using a device which is suitable for this
purpose, for
example a mixer for solid or solid/liquid components, until the composition is
distributed
uniformly on the seed. If appropriate, this is followed by drying.
Use example
Example 1: Curative treatment of diseased soybean plants
In field experiments, different varieties of soybean plants whose leaves were
already
infested with Phakopsora pachyrhizi were treated with an aqueous triticonazole
preparation using equipment conventionally used under practice conditions. The
application rates were from 20 to 200 g/ha. 25 days after the treatment, the
disease
level on the untreated, but infested, leaves had developed to such an extent
that it
covered 50% of the leaf area. In the treated plants, in contrast, Phakopsora
pachyrhizi
disease had only reached a maximum of 25%. This reduced disease level resulted
in
markedly improved yield in comparison with the untreated control.
Example 2: Protective treatment of diseased soybean plants
In field experiments, different varieties of soybean plants were treated with
an aqueous
triticonazole preparation. The application rates amounted to 20 to 200 g/ha.
Thereafter,
the plants were inoculated with Phakopsora pachyrhizi. 25 days after the
treatment, the
disease level on the untreated, but infested, leaves had developed to such an
extent
that it covered 50% of the leaf area. In the treated plants, in contrast,
Phakopsora
pachyrhizi disease had only reached a maximum of 25%. This reduced disease
level
resulted in markedly improved yield in comparison with the untreated control.
Example 3: Seed treatment
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Seed of soybean plants c.v. "Embrapa 48" were treated with a composition
suitable for
seed treatment, comprising triticonazole as active substance, at application
rates in the
range of from 12.5 g, 25 g, 50 g, 100 g and 250 g of triticonazole per 100 kg
of seed.
Thereafter, the seed was sown. The soybean plants thus grown were then
inoculated
with Phakopsora pachyrhizi. After 50 days, the level of rust disease of the
leaf areas
was determined. The disease level in the plants from untreated seed was at
least 50%,
whereas the disease level of the leaf area in plants from treated seed was
less than
25% in all cases.
Example 4_ Protektive Activity of Triticonazole against Soybean Rust Caused by
Pha-
kopsora pachyrhizi via Seed Treatment
A defined amound of a commercial ready-to-used formulation of Triticonazole
(suspen-
sion concentrate, concentration of active ingredient 200 g/1), corresponding
to the de-
sired application (a.r.) rate of 5, 15, 30 und 50 g ai/100 kg soybean was
diluted with
water to a total volume of 1 Ltr./ 100 kg Soybean.
Soybean seeds of the cultivar " IAC 8.2 " were treated in a commercial device
for
dressing seeds with the thus prepared aqueous suspension of triticonazole and
then
seeded in a field experiment in Brazil. The leaves of the soybean plants thus
grown
were inoculated at an appropriate growing stage with a spore suspension of
soybean
rust (Phakopsora pachyrhizi). Thereafter the plants were kept wet for 6-8 h
overnight
by means of a finely dripping sprinkling device. During this time the spores
germinated
and their germ tubes penetrated into the leaf tissue. 60 days after treatment
(60 DAT)
or seeding, respectively, the extent of rust formation on the leaves of the
infected
plants was determinated. The results are summarized in table 1:
Table 1:
a.r. % infected leaf area
g /100 kg (60 DAT)"
0 (untreated) 40
5 23
15 11
9
50 3
Example 5: Curative Activity of Tritconazole against Soybean Rust Caused by
Phakop-
sora pachyrhizi via Spray Application
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A commercial ready-to-used formulation of Triticonazole (suspension
concentrate, con-
centration of active ingredient 200 g/1) was diluted with water to the active
ingredient
concentraten (act.conc.) given in Table 2.
5 Leaves of potted soybean seedlings of the cultivar "Hutcheson" were
inoculated with a
suspension of spores of soybean rust (Phakopsora pachyrhizi). The pots were
placed
in a chamber with high atmospheric humidity (90 to 95%) at 22 to 24 C for 24
hours.
During this time, the spores germinated and the germ tubes penetrated into the
leaf
tissue. After 3 days, the infected plants were sprayed to runoff point with an
aqueous
10 suspension having the concentration of active compound as given in table 2.
The sus-
pensions or emulsions were prepared as described above. After the spray
coating was
dry, the test plants were cultivated in a greenhouse at temperatures between
22 and
24 C and at 90% relative humidity for 17 days. The extent of the rust
development on
the leaves was then determined. The results are summarized in table 2.
Table 2:
act.conc. % infected leaf area
ppm (17 DAT)'
0 (untreated) 80
1 9
4 1
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