Note: Descriptions are shown in the official language in which they were submitted.
0050/45359
227865
Coated solid crop protection composition formulation
The present invention relates to compositions containing one or
more crop protection active compounds in a formulation on a car-
rier and in the form of granules or as pellets which are coated
with a copolymer wax which was prepared from ethylene and an
a-olefinically unsaturated mqno- or dicarboxylic acid having 3 to
8 carbon atoms, and to a process for their production and fur-
ther, in the cases in which the crop protection active compound
is a fungicidal active compound, to a method of controlling harm-
ful fungi using these compositions.
It is generally known to fix crop protection active compounds to
a solid carrier using coating polymers such that the active com-
pound is only gradually released and can thus display its action
over a long period (slow-release formulation). The commercial
products, however, have the disadvantage that they are still
strongly prone to agglomeration, whereby the formulated goods
lose their flowability. The relatively high content of polymer in
the formulation can also be unsatisfactory.
It is an object of the present invention to find a formulation
for crop protection active compounds which does not have these
disadvantageous properties.
We have found that this object is achieved by compositions which
contain one or more crop protection active compounds in a for-
mulation on a carrier and in the form of granules or as pellets
and which are coated with a copolymer wax which was prepared from
ethylene and an a-olefinically unsaturated mono- or dicarboxylic
acid having 3 to 8 carbon atoms, and further, in the cases in
which the crop protection active compound is a fungicidal active
compound, a method of controlling harmful fungi using these com-
positions.
We have further found a process for their production and the use
of those compositions which contain a fungicidal crop protection
active compound for the control of harmful fungi.
Suitable crop protection active compounds are herbicidal, growth-
regulating, insecticidal and in particular fungicidal active
compounds.
0050/45359
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2
Suitable fungicidal crop protection active compounds are:
Tridemorph (2,6-dimethyl-4-tridecylmorpholine), fenpropimorph(4-
(2-methyl-3-j4-tert-butylphenyl]propyl)-2,6-dimethylmorpholine,
S in particular the isomer of which, in which the methyl groups on
the morpholine ring are cis to one another, fenpropidine (N-[3-
(4-tert-butylphenyl)-2-methylpropyl]piperidine).
The component fenpropimorph can be present in two stereoisomeric
forms (morpholine ring), the cis isomer being preferred. The
invention includes compositions which contain the pure isomers of
the compound fenpropimorph, in particular the cis isomer, and
compositions which contain mixtures of the isomers.
Fungicidal crop protection active compounds which are furthermore
suitable are:
(+)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cyclohepta-
nol, metsulfovax, cyprodinil, methyl (E)-2-{2-[6-(2-cyanophe-
noxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate and the azole
active compounds N-propyl-N-[2,4,6-trichlorophenoxy)ethyl]-
imidazole-1-carboxamide (prochloraz), (Z)-2-(1,2,4-triazol-1-yl-
methyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)oxirane (epoxicon-
azole) of the formula
N
~N O
~J
so
cl
F
1-butyl-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanol
(hexaconazole), 1-[(2-chlorophenyl)methyl]-1-(1,1-dimethyl)-
2-(1,2,4-triazol-1-ylethanol [sic], 1-(4-fluorophenyl)-
I-(2-fluorophenyl)-2-(1,2,4-triazol-1-yl)ethanol (flutriafol),
(RS)-4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-yl-
methyl)butyronitrile, 1-((2 RS, 4 RS; 2 RS, 4 SR)-4-bromo-
2-(2,4-dichlorophenyl)tetrahydrofurfuryl]-1H-1,2,4-triazole,
3-(2,4-dichlorophenyl)- 2-(1H-1,2,4-triazol-1-yl)quinazo-
lin-4-(3H)-one, (RS)-2,2-dimethyl-3-(2-chlorobenzyl)-
4-(1H-1,2,4-triazol-1-yl)-butan-3-ol, bitertanol, triadimefon,
triadimenol, bromuconazole, cyproconazole, dichlobutrazole,
difenoconazole, diniconazole, etaconazole, fluquinconazole,
imibenconazole, propiconazole, flusilazole, tebuconazole,
0050/45359
2I'~865~
3
imazalil, penconazole, tetraconazole, triflumizole, metconazole,
fluquinconazole [sic], fenbuconazole, triticonazole.
The fungicidal crop protection active compounds preferably origi-
nated from the group consisting of: tridemorph, fenpropimorph,
fenpropidine, azole active compound, it being possible for one or
more active compounds from the group consisting of tridemorph,
fenpropimorph and fenpropidine to be present in the compositions.
The following azole active compounds are preferred: prochloraz,
epoxiconazole, hexaconazole, cyproconazole, difenoconazole,
propiconazole, flusilazole, diniconazole, triticonazole and tebu-
conazole, epoxiconazole being used with particular advantage.
The crop protection active compounds can also be present in the
form of their salts or metal complexes. The compositions thus ob-
tained are also included by the invention.
The salts are prepared by reaction with acids, eg. hydrohalic
acids such as hydrofluoric acid, hydrochloric acid, hydrobromic
acid or hydriodic acid, or sulfuric acid, phosphoric acid, nitric
acid or organic acids such as acetic acid, trifluoroacetic acid,
tri-chloroacetic acid, propionic acid, glycolic acid, lactic
acid, succinic acid, citric acid, benzoic acid, cinnamic acid,
oxalic acid, formic acid, benzenesulfonic acid, p-toluenesulfonic
acid, methanesulfonic acid, salicylic acid, p-aminosalicylic acid
or 1,2-naphthalenedisulfonic acid.
By choice, metal complexes can contain only one crop protection
active compound or alternatively several crop protection active
compounds. Metal complexes can also be prepared which contain
these active compounds together in a mixed complex.
Metal complexes are prepared from the organic molecule on which
they are based and an inorganic or organic metal salt, for
example the halides, nitrates, sulfates, phosphates, acetates,
trifluoroacetates, trichloroacetates, propionates, tartrates,
sulfonates, salicylates or benzoates of the metals of the second
main group, such as calcium and magnesium, and of the third and .
fourth main group, such as aluminum, tin or lead, and of the
first to eighth subgroup, such as chromium, manganese, iron,
cobalt, nickel, copper or zinc. The subgroup elements of the 4th
period and in particular copper are preferred. The metals can in
this case be present in the various valencies befitting them. The
metal complexes can contain one or more organic molecule com-
ponents as ligands.
0050/45359
_ . ~ 21'~865~
4
The control of harmful fungi using the fungicidal compositions,is
expediently carried out by allowing a fungicidally active amount
of the fungicidal composition to act in or on the soil, on the
seed planted in the soil or on the plants developing therefrom or
on seedlings.
Owing to the delayed release of the active compounds, the release
rates of the active compounds in the soil can be controlled such
that, for example in the case of the fungicidal crop protection
active compounds, an effective protection from fungal diseases
can be maintained over the whole vegetation period. Absorption of
the active compound takes place continuously via the roots to the
extent of the controlled release of the active compounds from the
active compounds formulated according to the invention, and the
active compounds are then distributed in the plants systemically
via the roots.
Compared with the widely used spray application of the crop
protection active compounds for fungal control, the process
according to the invention offers the following advantages:
- Effective protection of the plants against fungal diseases
can be achieved over the whole vegetation period by a single
application of the active compounds formulated according to
the invention to soil, which advantageously is carried out
togetherwith the seed or with the planting of seedlings.
- The hitherto customary use of several spray applications to
the growing crop hereby becomes unnecessary, whereby a sig-
nificant expenditure of labor can be saved.
- By application of the crop protection active compounds in the
form of the formulation according to the invention, lower
amounts of the active compounds to be applied result.
- When using the process according to the invention, seed
dressing is not necessary.
It is an essential feature of the present invention that the crop
protection active compounds are present in a formulation having
delayed release of active compound. By means of such a controlled
release of active compound, it is possible to maintain an effec-
tive protection of the crop plants against fungal attack over the
entire vegetation period using one application of the fungicidal
compositions according to the invention to the soil.
0050/45359
21786
The granules are prepared as coated granules by first applying .
the active compounds to solid granule-shaped carriers. The active
substance-containing granules obtained are then coated with suit-
able coating substances which cause a delayed, controlled release
5 of active compound.
Suitable solid carriers for the coated granules are, for example,
mineral earths such as silica gel, silicic acids, silica gels
[sic], silicates, talc, kaolin, limestone, lime, chalk, bole,
loess, clay, dolomite, diatomaceous earth, calcium sulfate and
magnesium sulfate, magnesium oxide, ground synthetic materials,
fertilizers such as ammonium sulfate, ammonium phosphate, ammo-
nium nitrate and ureas, eg. crotonylidenediurea or isobutylidene-
diurea, and vegetable products such as grain flour, corn flour,
tree bark, wood and nutshell meal, corn meal and cellulose pow-
der. Fertilizer granules or pellets are preferred as carriers and
in particular those containing phosphate.
The granules in general have a grain size range of from 0.1 to
10 mm, preferably from 0.5 to 8 mm, in particular from 1 to 6 mm.
The active compounds are as a rule applied to the carriers by
spraying them on in the form of oil-in-water emulsions, emulsion
concentrates, suspoemulsions, suspension concentrates or in
organic solvents, or preferably dissolved in water.
In the case of the active compounds tridemorph, fenpropimorph and
fenpropidine, the use of oil-in-water emulsions, emulsion concen-
trates or the solutions mentioned is preferred.
The spraying on is carried out eg. in fluidized bed apparatuses
or in drums or rotary disks in which the carrier granules are
rolled, in perforated vessels with controlled conduct of the dry-
ing medium, expediently air, or in air suspension processes. In
general, temperatures of from 10°C to 110°C are used for the
spraying-on and the drying.
The carrier containing the applied active compound is then coated
with suitable coating substances. The coating substances employed
for the controlled release of active compound from the coated
granules are aqueous wax dispersions, containing, based on the
aqueous wax dispersion, from 5 to 40% by weight of an ethylene
copolymer wax, consisting of from 10 to 25% by weight of an
a-olefinically unsaturated mono- or dicarboxylic acid having 3 to
8 C atoms and from 90 to 75% by weight of ethylene having an MFI
value, measured at 190°C and a loading of 2.16 kp, of from 1 to
600, preferably from 5 to 500, in particular from 15 to 300, or
0050/45359
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6
an MFI value, measured at 160'C and 325 p, of from 1 to 600,.from
0.1 to 5% by weight of alkali metal hydroxide, ammonia, an
alkanolamine or a dialkanolamine and their mixtures and, as the
remainder, water to 100%.
The copolymers of ethylene to be used for the wax dispersions
contain from 10 to 25, preferably from 15 to 24, % by weight of
a-olefinically unsaturated mono- or dicarboxylic acids having 3
to 8 C atoms, of which, for example, acrylic acid, methacrylic
acid, crotonic acid, malefic acid, fumaric acid and itaconic acid
may be mentioned. Of these, methacrylic acid and, in particular,
acrylic acid and their mixtures are preferred.
The ethylene copolymer waxes are characterized according to the
invention by a specific MFI (melt flow index) or melt index. The
MFI indicates the amount of the polymer melt in grams which. can
be forced at a specific temperature through a nozzle of specific
dimensions with a specific expenditure of force (loading). The
determination of the melt indices (MFI units) is carried out ac-
cording to the following standard procedures, ASTM D 1238-65 T,
ISO R 1133-1696 (E) or DIN 53 735 (1970), which are identical
with one another.
The wax dispersions furthermore contain mostly bases and precise-
ly, as a rule, from 0.1 to 5, preferably from 1 to 3, % by weight
of alkali metal hydroxide, preferably potassium hydroxide or
sodium hydroxide, ammonia, a mono-, di- or trialkanolamine in
each case having from 2 to 18 C atoms in the hydroxyalkyl
radical, preferably from 2 to 6 C atoms, or mixtures of the alka-
nolamines mentioned or a dialkylmonoalkanolamine in each case
having from 2 to B C atoms in the alkyl or hydroxyalkyl radical,
or their mixtures. Amines which may be mentioned are, for exam-
ple, diethanolamine, triethanolamine, 2-amino-2-methylpropanol or
dimethylethanolamine. Ammonia is preferably used.
owing to the base component in the wax dispersions, the carboxyl-
ic acid groups in the copolymer waxes are at least partly present
in the salt form. Preferably, these groups are neutralized to 50
to 90 and, especially, to 60 to 85%.
The coating layer can additionally contain substances for con-
trolling the release of the active compounds. These are eg.
water-soluble substances such as polyethylene glycols, polyvinyl-
pyrrolidone, or copolymers of polyvinylpyrrolidone and polyvinyl
acetate. The amount thereof is, for example, from 0.1 to 5% by
0050/45359
2~7~655
weight, preferably from 0.1 to 3% by.weight, based on the coating
substance.
The application of the coating layer is expediently carried out
by spraying on solutions, dispersions or dispersion [sic] of the
coating substances mentioned in organic solvents or water.
An aqueous suspension or an emulsion of the coating substance is
preferably used which has, in particular, a content of polymer
substance of from 0.1 to 50 and especially of from 1 to 35% by
weight. Further auxiliaries can be added in this case to optimize
the processability, eg. surface-active substances and solids such
as talc and/or magnesium stearate.
A wax dispersion is particularly preferred which contains from 5
to 40% by weight of an ethylene copolymer wax, from 0.1 to 5% by
weight of ammonia and from 55 to 94.9% by weight of water or con-
sists of these components, the ethylene copolymer wax being com-
posed of from 75 to 90% by weight of ethylene units and of from
10 to 25% by weight of units of an a-olefinically unsaturated
mono- or dicarboxylic acid having 3 to 8 carbon atoms.
The coated polymers used according to the invention are generally
known or obtainable according to known methods (cf. eg.
DE A 34 20 168; EP A 201 702; US-A 5 206 279).
Spraying-on is carried out, for example, in fluidized bed appara-
tuses or in drums or rotating disks in which the carrier granules
are rolled, in perforated vessels with controlled conduct of the
drying medium or in air suspension processes. In general, the
process is carried out at from 10~C to 110~C.
The fungicidal compositions thus obtained and provided with the
coating layer can be used as such for the control of fungi
according to the invention with controlled release of active
compound.
However, it can also be advantageous additionally to apply active
compound from outside to these compositions. The compositions
thus obtained enable a further graduation of the controlled re-
lease of active compound, the active compounds applied to the
coating layer on the outside being important for a more specific
initial action. It may additionally be advantageous also to use a
second coating layer, by means of which a further possibility of
control for the delayed release of the active compounds results.
In addition.to the coating technique described above, there is a
0050/45359
8
further advantageous technique for the production of the composi-
tions according to the invention in a formulation having delayed
release of active compound in which the active compounds are in-
corporated into suitable matrix substances from which the active
compounds are released in a delayed and controlled manner. The
matrix used in this case can be, for example, the material
employed for the coating. Preparation is expediently carried out
here by dissolving or dispersing the active compounds in the
solution or dispersion of the coating material and then applying
this preparation, as described above for the coating substances,
to the carrier material. It,is ensured by this means that the
active compounds are dispersed uniformly in the coating layer. As
a rule, release from these formulations is diffusion-controlled.
The fungicidal compositions for example contain in general from
0.01 to 95, preferably from 0.05 to 90, 8 by weight of crop
protection active compound.
Depending on the effect desired, the application rates are from
0.02 to 5 kg, preferably from 0.05 to 3 kg, of crop protection
active compound per ha. The ratio of active compound in a fungi-
cidal two-component mixture in this case is in general from 50:1
to 1:10, preferably from 20:1 to 1:5, in particular from 10:1 to
1:2.
The fungicidal compositions are distinguished by an outstanding
activity against a broad spectrum of phytopathogenic fungi, in
particular from the Ascomycetes and Basidiomycetes classes.
They are of particular importance for the control of a multipli-
city of fungi on various crop plants such as cereals, eg. wheat,
rye, barley, oats, rice, rape, sugar beet, corn, soybeans,
coffee, sugar cane, decorative plants and vegetable plants such
as cucumbers, beans and cucurbits. The fungicides prepared
according to the invention are used with particular advantage for
fungal control on cereals.
The fungicidal compositions are expediently applied by allowing
the composition to act in or on the soil on the seed planted in
the soil or on the plants developing therefrom or on seedlings.
The application of the composition and the planting of the seed
or the planting of the seedlings can take place in separate
operations, it being possible for the application of the composi-
tion to take place before or after the planting of the seed or
the planting of the seedlings.
It is particularly advantageous to apply the formulated crop
0050/45359
217865
9
protection active compound together with the seed or the planting
of the seedlings.
The following examples illustrate the invention.
A. Examples of formulations according, to the invention
a) The active compound epoxiconazole was processed in the
form of a suspension concentrate of the following com-
position:
500 g/1 of epoxiconazole,
30 g/1 of a block copolymer having a propylene oxide
core of approximate molecular weight 3250, to
which ethylene oxide up to a molecular weight of
approximately 6500 is grafted as a dispersant
(BASF, Germany),
20 g/1 of a sodium salt of a condensation product of
phenolsulfonic acid, urea and formaldehyde as a
dispersant (BASF, Germany) and
the difference to 1 1 of water. The liquid
preparations of epoxiconazole used in the
following examples were obtained by diluting
this suspension concentrate with the appropriate
amount of water.
The active compound fenpropimorph was processed as an
oil-in-water emulsion of the following composition:
200 g/1 of fenpropimorph,
37 g/1 of a p-isononylphenol etherified with 8 ethylene
oxide units as an emulsifier (BASF, Germany),
87.5 g/1 of a 1:1 mixture (weight) of 2-ethylhexanoic
acid and a p-isononylphenol etherified with 7
ethylene oxide unite as an emulsifier (BASF,
Germany) and
the difference to 1 1 of water.
0050/45359
21'~86~~
m
Example 1
a) Application of epoxiconazole to NP fertilizer
A solution of 3.0 g of epoxiconazole, prepared according to
(a), in 27.0 g of water were sprayed onto 4 kg of a nitrogen/
phosphate fertilizer (Nitrophoska~ fertilizer.20-20-0, BASF)
with a particle size in the range 2-3.5 mm and a bulk weight
of 1050 g/1 in a fluidized bed coating apparatus (Aeromatic
coater-MP 1), and the fertilizer particles obtained after
spraying were then dried. The inlet air temperature to the
fluidized bed coating apparatus was 39~C during the spraying
process and during the drying.
b) Application of the coating substance
The coating substance used was a wax dispersion containing
27% by weight of an ethylene/acrylic acid copolymer compris-
ing 20% by weight of acrylic acid and 80% by weight of ethyl-
ene, 3.68% by weight of ammonia solution (25% strength by
weight), 0.20% by weight of Na2S2o5 and 69.10% by weight of
water. A mixture of 740 g of this wax dispersion and 100, m1
of water-was sprayed in a fluidized bed coating apparatus
onto 3.8 kg of the fertilizer granules treated with epoxi-
conazole as described in section a) above and warmed to 40~C
with admission of air at from 39 to 42~C over a period of
70 min. Drying was then carried out at from 39 to 42~C for a
further 10 min with further admission of air. The content of
the coating layer in the coated fertilizer granules obtained
after drying was 5% by weight, based on the coated fertilizer
granules.
Example 2
The procedure was as described in Example lb), but 4.89 kg of the
wax dispersion were sprayed as a coating substance onto 12 kg of
the fertilizer granules treated with epoxiconazole as described
in Example 1a) at an air inlet and air outlet temperature in the
range 45-48'C, the total time for the spraying and drying being
175 min. The content of the coating layer, based on the coated
fertilizer granules obtained after drying, was 10% by weight.
Example 3
The procedure was as described in Example lb), but three times
the-amount of the Wax dispersion were sprayed on at an air inlet
and air outlet temperature of 44-45~C, the total time for the
0050/45359
~ 217865
11
spraying and the subsequent drying being 200 min. The content of
the coated layer, based on the coated fertilizer granules ob-
tained after drying, was 15% by weight.
Example 4
a) Application of fenpropimorph to NP fertilizer
20 g of fenpropimorph (according to (~), see above) were
sprayed in the course of about 11 min at an air inlet temper-
ature of 60~C onto 4 kg of a nitrogen/phosphate fertilizer
(Nitrophoska~ fertilizer 20-20-0 BASF) having a particle size
in the range 2-3.5 mm in a fluidized bed coating apparatus
(Aeromatic coater MP 1).
b) Application of the coating substance
The coating substance used was a wax dispersion containing
27% by weight of an ethylene/acrylic acid copolymer,compris-
ing 20% by weight of acrylic acid and 80% by weight of ethyl-
ene, 3.68% by weight of ammonia solution (25% strength by
weight), 0.20% by weight of NaiS205 and 69.10% by weight of
water. A mixture of 713 g of this wax dispersion and 96 ml of
water was sprayed in a fluidized bed coating apparatus onto
3.8 kg of the fertilizer granules treated with fenpropimorph
(according to (~), see above) and warmed to 45~C with admis-
sion of air at from 40 to 42~C over a period of 62 min. Dry-
ing was then carried out for a further 5 min with further ad-
mission of air at from 40 to 42~C. The content of the coating
layer in the coated fertilizer granules obtained after drying
was about 5% by weight, based on the coated fertilizer
granules.
Example 5
The procedure was as described in Example 4b), but, as a coating
substance, 1.428 kg of the wax dispersion were sprayed onto
3.4 kg of the fertilizer granules treated with fenpropimorph as
described in Example 4a) at an air inlet and air outlet
temperature in the range 44-45~C, the total time for the spraying
and subsequent drying being 125 min. The content of the coating
layer, based on the coated fertilizer granules obtained after
drying, was about 10% by weight.
,. 0050/45359
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12
Example 6
The procedure was as described in Example 4b), but 2.142 kg of
the wax dispersion were sprayed onto 3.4 kg of the fertilizer
granules treated with fenpropimorph as described in Example 4a)
at an air inlet and air outlet temperature of 44-45~C, the total
time for the spraying and the subsequent drying being 190 min.
The content of the coating layer, based on the coated fertilizer
granules obtained after drying, was 15% by weight.
Example 7
Corresponding to Examples la) and 4a), two active compound solu-
tions were applied by two separate nozzles to 3.8 kg of NP
20-20-0 fertilizer granules simultaneously. One solution con-
tained 2.5 g of epoxiconazole (according to (a), see above), and
the other an oil-in-water emulsion of 15 g of fenpropimorph.
After drying, the granules treated in this way were treated cor-
responding to the spraying procedure lb) or 4b) with 740 g of the
wax dispersion described there, the air inlet temperature being
45'C and the total time for the application 62 min.
Example 8
15 g of fenpropimorph were stirred as such into and uniformly
dispersed in 740 g of the wax dispersion described in Example
lb). Using this preparation, 3.8 kg of NP 20-20-0 fertilizer
granules were coated as in Ex. lb) (45~C air inlet temperature,
52 min application time).
Example 9
The procedure was as in Example 8, only instead of 15 g of fen
propimorph 2.5 g of epoxiconazole (according to (a), see above)
were stirred in as such.
Example 10
The procedure was as in Example 8, only in addition to the 15 g
of fenpropimorph 2.5 g of epoxiconazole (according to (a), see
above) were also stirred as such into the wax dispersion.
Examples 11 - 16
Examples 11 - 16 were carried out in a similar manner to Examples
1, 2, 4; 5 and 7 in each case using 3.8 kg of NP 20-20-0 ferti-
lizer granules, but instead of the wax dispersion described above
0050/45359
13
using an aqueous polymer dispersion .(of the type Acronal~, BASF)
which consisted to 50% by weight of water and to 40% by weight of
a copolymer of methyl methacrylate and n-butyl acrylate (1:1) as
coating substance. The individual application rates and test
parameters can be seen from the following table. The inlet air
temperature in all cases was 40 - 45~C.
Ex.NO. Fenpropimorph Epoxiconazole Acronal Time for
as pure according to (40% strength)spraying
substance (a)
Lg) Lgl
11 15 - 500 g 43 min
12 15 - 1000 g 82 min
13 - 2.5 500 g 43 min
14 - 2.5 1000 g 82 min
15 15 2.5 500 g 49 min
16 15 2.5 1000 g 87 min
The amount of coating in the finished granules was 5% by weight
each in Examples 11, 13 and 15, and 10% by weight each in Exam-
ples 12, 14 and 16. The product was subsequently also powdered on
a disk with 0.25% by weight of talc.
Examples 17 - 22
Examples 17 - 22 were carried out in a similar manner to Examples
11 - 16, but the active compounds were not applied separately but
were stirred into the coating dispersion used and then applied
together with this. The application rates and the other process
parameters remained virtually unchanged.
Examples 23 and 24
Examples 23 and 24 were carried out in a similar manner to Exam-
ples 11 and 13, but the carrier material used was 2.0 kg of pum-
ice split having a particle size of 2.0-- 3.5 mm and a bulk
weight of 460 g/1. On account of the lower density of the pumice
split, the coating amount in the finished product was in this
case 10% by weight.
Examples 25 - 30
Examples 25 - 30 correspond in their implementation to the exam-
plea described above as follows: Example 25 corresponds to Exam-
ple 11, Example 26 corresponds to Example 17, Example 27 corres-
ponds to Example 13, Example 28 corresponds,to Example 19,
0050/45359
2I~86~~
14
Example 29 corresponds to Example 15 and Example 30 corresponds
to Example 21. Instead of the 3.8 kg of NP 20-20-0 fertilizer,
however, 1.8 kg of corn meal (product of Eurama S.A. (France) of
the type Eu-Grit 8/10) having a particle size of 2.0 - 3.15 mm
and a bulk weight of 450 g/1 was used as the carrier material.
The amount of coating substance was also 10% by weight here be-
cause of the lower bulk weight. The air inlet temperature was 50~C
and the time for spraying from 40 to 50 min. The.finished
granules were also treated with 1% by weight of talc.
Example 31
Corresponding to Example 7, solutions of 7.5 g of fenpropimorph
(according to (S), see above) and of 1.25 g of epoxiconazole (ac-
cording to (a), see above) in 38.75 g of water were first applied
to 3.8 kg of NP 20-20-0 fertilizer and dried. A mixture of 500 g
of the Acronal dispersion described in Examples 11 - 16, S g of
fenpropimorph (according to (~), see above) and 0.83 g of epoxico-
nazole (according to (a), see above) was then applied as a coat-
ing and dried (time: 45 min, temp.: 45~C inlet air). Finally,
solutions of 2.5 g of fenpropimorph (according to ((3), see above)
in 10.8 g of water and 0.42 g of epoxiconazole (according to (a),
see above) were again applied to the coating on the outside. The
finished product contains 5% by weight-of coating material and
half of the active compounds are dispersed under the coating, a
third in the coating matrix and a sixth on the outside on the
coating.
Example 32
This example was carried out in a similar manner to Example 31,
but instead of the Acronal dispersion 740 g of the wax dispersion
described in Example lb) were used (time: 55 min, temp.: SO~C).
The product contained 5% by weight of coating material and has
the active compound distribution shown in Example 31.
Example 33
The example was carried out in a similar manner to Example 31.
However, the individual application rates of the active compounds
were varied such that their distribution in the finished product
changed such that one third of the active compounds were applied
under the coating and two thirds were embedded in the coating ma-
terial.
0050/45359
21'~865~
Example 34
This example was carried out in a similar manner to Example 33,
but 740 g of the wax dispersion as described in Example lb were
5 used as coating material.
This example was carried out in a similar manner to Examples 31
and 33, but instead of the fertilizer 1.8 kg of corn meal as de-
scribed in Examples 25 - 30 were used as carrier granules.
10 Because of the lower bulk weight, in this case a coating amount
of 10% by Weight again resulted in the finished product. Active
compound dispersion was carried out by applying two thirds under
the coating layer and embedding one third in the coating layer.
15 B. Use examples
Testing of the fungicide granules having delayed release of ac-
tive compound for the control of seed- and airborne harmful fungi
on cereals
Fungicide granules having delayed release of active compound were
mixed with winter wheat seed of the variety Rektor such that dur-
ing simultaneous sowing of 200 kg/ha of loose smut- and covered
smut-infected wheat and [sic] 100 kg/ha of the fungicide granules
according to the invention were applied to the same drill row
using a drilling machine. The amounts of active compound were,
per ha, 300 g of fenpropimorph or 50 g of epoxiconazole or, on
combination of both active compounds, 125 g of fenpropimorph and
25 g of epoxiconazole (Use Example i). on complete ripening of
the wheat (development stage 89), the cobs attacked by loose smut
(Ustilago tritici)and covered smut (Tilletia caries) were
counted and the effectiveness of the fungicide granules was con-
verted to efficiencies according to Abbott (0 = Without effect,
100 = harmful fungus completely controlled). The results are
shown in Use Example 1.
The application of seed and granules was also carried out with
barley seed of the variety Beate and the fungicide granules hav-
ing delayed release of active compound in the same manner as with
the wheat seed. 200 kg/ha of barley and 200.kg/ha of the fungi-
cide granules according to the invention were sown
simultaneously. The amount of active compound per ha was 750 g of
fenpropimorph or 125 g of epoxiconazole or, in combination, 375 g
of fenpropimorph and 125 g of epoxiconaaole (Use Example 2). At
the end of the barley blooming period (development stage 69), at-
tack by mildew (Erysiphe graminis) and net blotch (Pyrenophora
teres) was c]etermined as total plant attack and the effect of the
_. 0050/45359
2I'~865~
,
16
fungicide granules was converted into efficiencies according to
Abbott. Use Example 2 shows the results of this test.
10
20
as
35
45
0050/45359
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