Note: Descriptions are shown in the official language in which they were submitted.
0050/44517
;` 2179181
Funglcidal composLtions
The present invention relates to fungicidal compositions having
5 synergistic fungicidal action in a formulation having delayed
release of active compound and methods of controlling fungi using
these compositions.
It is known to use a mixture of
a) 2-(1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chloro-
phenyl ) oxirane ( ~p~Yi c^n~
and
b ) 4- ( 2-methyl-3- [ 4-tert-butylphenyl ] propyl ) -2, 6-dimethylmorpho-
line (fenpropimorph) or tridemorph or fenpropidine
as a fungicide (EP--A 425 857).
It is further known to use a mixture of
a) prochloraz
25 and
b) tridemorph or fenpropimorph
as a fungicide (EP--A 72 156).
According to the known methods, the application of the active
~ J~ (a) and (b) for controlling fungi is carried out in the
customary manner, eg. by spray application. In this case, as a
rule several applications to the growing crop are necessary, 80
35 these applications are associated with appreciable expenditure of
labor. In the case of application to the plant and foliar appli-
cation, the problem further arises that the active ~ u--ds can
come into contact with the surrounding air on account of the
application method, 90 that they become partly lost for applica-
40 tion as a fungicide and at the same time can pollute the environ-
ment .
A fungicidal composition has now been found which contains, in a
formulation having delayed release of active compound, a fungi-
45 cidally active amount of
.
0050/44517
2 2179181
a ) 4- ( 2-methyl-3- [ 4-tert-butylphenyl ] propyl ) -2, 6-dimethylmorpho-
line ( ~enpropimorph ) and/or the active compound tridemorph
and/or the active compound fenpropidine
5 and
b ) a f urther f ungicidal crop protection active compound
in a formulation having delayed release of active compound [sic],
10 [lacuna] is advantageously suitable for controlling fungi.
~hese fllnr~ compositions arQ preferably formulated in the
form of granules or pellets having delayed release of active com-
pound. The control of fungi using the f~lnr; r~ ~Al composition3 in
15 a formulation having delayed release of active compound is expe-
diently carried out by allowing a fllnriri~7l ly active amount of
the ~llnriri~l 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 ~ ~, the release
rates of the active _ in the soil can be controlled such
that an effective protection frora fungal diseases can be main-
tained over the whole vegetation period. Absorption of the active
25 compound takes place continuously via the roots to the extent of
the controlled release of the active ~ '- from the active
compounds formulated according to the invention, and the active
compounds are then distributed in the plants systemically via the
roots .
::ompared with the spray application of the active ~ (a)
and (b) customary hitherto for fungal control, the process ac-
cording to the invention for fungal control 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 ~Q formulated according to
the invention to soil, which advantageously is carried out
together with the seed or with the planting of g~e~ll in~8.
- ~he hitherto customary use of several spray applications to
the growing crop hereby becomes llnn~r~Qs~ry~ whereby a sig-
nif Lcant expenditure of labor can be saved.
0050/44517
. 3 2179181
- The contact of a part of the active _ ' with the sur-
rounding air taking place during foliar application according
to the prior processes and the loss of active compound
associated therewith and a pollution of the environment which
may be associated therewith do not apply.
- The process according to the invention makes possible a more
specific application of active compound to a smaller area.
10 - ~ower amounts of the active _ .1~ to be applied thereby
result .
-- When using the process according to the invention, the seed
dressing necessary according to the conventional process does
not apply.
Tridemorph is 2, 6-dimethyl-4-tridecylmorpholine .
Fenpropidine is N- [ 3- ( 4-tert-butylphenyl ) -2-methylpropyl-
20 piperidine [sic].
The component fenpropimorph can be present in two stereoisomericforms (morpholine ring), the cis isomer being preferred. The in-
vention includes mixtures which contain the pure isomers of the
25 compound fenpropimorph, in particular the Ci8 isomer, and mix-
tures which contain mixtures of the isomers.
The following is [sic] suitable, for example, as further fungi-
cidal crop protection active compound ( b ):
( + ) -cis--1- ( 4-chlorophenyl ) -2- ( lH-1, 2, 4--triazol--1--yl ) cyclohepta-nol, metsulfovax, cyprodinil, methyl (E)-2--{2--[6--(2--cyano-
phenoxy ) pyrimidin- 4--yloxy ] phenyl } - 3--methoxyacryl ate and, i n
particular, the azole active _ N-propyl-N- [ 2, 4, 6-tri-
35 chlorophenoxy)ethyl]imida2ole-l- ~-~rh~Y~rn;de (prochloraz),
(Z)-2-(1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chloro-
phenyl)oxirane (~rnY;~ n~7ol~) of the formula
N
! ~ ~J
0050/44517
- 4 2~79l8i
1-butyl-1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanol
(h~Y:Ir~nA7nl,0), 1-[(2-chlorophenyl)methyl]-1-(1,1-dimethyl)-
2-(1,2,4-triazol-1-ylethanol [sic], 1-(4-fluorophenyl)-
1-(2-fluorophenyl)-2-(1,2,4-triazol-l-yl)ethanol (flutriafol),
5 (RS)-4-(4-chlorophenyl)-2-phenyl-2-(lH-1,2,4-triazol-l-yl-
methyl)butyronitrile, 1-[(2 RS, 4 RS; 2 RS, 4 SR)-4-bromo-
2-(2,4-dichlorophenyl)tetrahy.lLuruL~uLyl]-lH-1,2,4-triazole,
3-(2,4-dichlorophenyl)-2-(lH-1,2,4-triazol-l-yl)q~l;n~7nl;n_
4- ( 3H ) -one, ( RS ) -2, 2-dimethyl-3- ( 2-chlorobenzyl ) -4- ( lH-1, 2, 4-tri-
10 azol-1-yl)-butan-3-ol, bitertanol, triadimefon, tr; ;-.1; nnl ~
I~L- ~7nl~ cyproconazole, dichlobutrazole, difl~nn~nnA7c~l e,
~l;n;rnns~7nl~ et~rnn~701P, fluqll;nr~ 7nl-~, ;m;hc~nrnn~7n~
prnp; c~nn~7nl ~ flllQ; 1 :l7nl F~, tl~hurnnsl7c~ imazalil, p~.nrnn;l7nl F.,
tetraconazole, triflumizole, metconazole, fluqll;nrnnsl7nl~ [8ic]~
15 fc~nhllrnn~7ol~-~ triticonazole.
The following are preferred as azole active compound (b): pro-
chloraz, ~pnY;cnn~7n1~, h~yArnn~7r~le~ cyprornn~7nlF~ difenocona--
zole, pro~;cnn:~7nl~ fl~lQ;l5l7ol~ ;n;rnn:~7ole~ triticonazole and
20 teb~rnn~7nl-~, epoxiconazole being used with particular advantage.
The active ~ (a) and (b) can also be present in the form
of their salt3 or metal complexes. These mixtures are also in-
cluded by the invention.
The salts are prepared by reaction with acids, eg. hydrohalic
acids such as hydrofluoric acid, hydrochloric acid, ~ydLublu.,ic
acid or hydriodic acid, or sulfuric acid, phosphoric acid, nitric
acid or organic acids such as acetic acid, trifluoroacetic acid,
30 tri--chloroacetic acid, propionic acid, glycolic acid, lactic
acid, succinic acid, citric acid, benzoic acid, cinnamic acid,
oxalic acid, formic acid, bc~n7~npslll fonic acid, p-toluenesulfonic
acid, methanesulfonic acid, salicylic acid, p_~m; nns~l; rylic acid
or 1,2-naphth~ n~-l;Qulfonic acid.
By choice, metal 1~Y-~Q can contain only one component (a) or
one component (b) or alternatively several components (a) or (b).
Metal complexes can also be prepared which contain both compo-
nents ( a ) and ( b ) together in a mixed complex .
Metal ~ yl~q are prepared from the organic molecule on which
they are based and an inorganic or organic metal salt, for exam-
ple the halides, nitrates, sulfates, phosphates, acetates, tri-
fluoroacetates, trichloroacetates, propionates, tartrates, sulfo-
45 nates, salicylates or benzoates of the metals of the second maingroup, such as calcium and r-~n~; , and of the third and fourth
main group, such as aluminum, tin or lead, and of the first to
0050/44517
5 2179l81
eighth subgroup, such as chromium, manganese, iron, cobalt, nick-
el, 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
5 complexes can contain one or more organic molecule components as
ligands .
It is an essential feature of the present invention that the com-
ponents (a) and the components (b) are present in a formulation
10 having delayed release of active compound. By means of such a
controlled release of active compound, it is possible to maintain
an effective protection of the crop plants against fungal attack
over the entire vegetation period using one application of the
~llnqi ~ composition8 according to the invention to the soil.
Preferably, the fungicides according to the invention are formu-
lated as granules or pellets having delayed release of active
compound .
20 Suitable granules are prepared, for eYample, as coated granules
by first applying the active . to solid granule-shaped
carriers. The active substance-containing granules obtained are
then coated with suitable coating substances which cause a
delayed, controlled release 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, diat~ earth, calcium sulfate and
30 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
35 powder. Fertilizers are advantageously used as carriers. Ferti-
lizer granules or pellets are preferred as carriers, in particu-
lar those containing phosphate.
The granules in general have a grain size range of from 0.1 to
40 10 mm, preferably from 0.5 to 8 mm, in particular from 1 to 6 mm.
The active ~1~ are as a rule applied to the carriers by
spraying them on in the form of oil--in-water emulsions, emulsion
concentrates, ~uaL - 1 ~ions, suspension concentrates or in or-
45 ganic solvents, or preferably dissolved in water.
0050/44517
- ` ~ 6 217918~
In the case of the active ~ ( a ), the use of oil-in-water
1 q;onc~ emulsion concentrates or the solutions mentioned is
pref erred .
5 The spraying--on i8 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
10 spraying-on and the drying.
~he carrier containing the applied active compound is then coated
with suitable coating substances. Suitable coating substances for
the controlled release of active compound from the coated gran-
15 ules are eg. polymers and copolymers of acrylic acid and/ormethacrylic acid and/or their esters, preferably copolymers based
on Cl-C6-alkyl acrylates and Cl-C6-alkyl methacrylates, for exam-
ple based on butyl acrylate and methyl methacrylate; copolymers
of acrylic and methacrylic acid esters with a low content of
20 ammonium groups (eg. Eudragit~9 RS), copolymers of acrylic and
methacrylic acid esters and trimethylammonium methacrylate; poly-
vinyl acetate; hydroxypropylmethylcellulose phthalate or acetate
succinate; cellulose acetate phthalate, starch acetate phthalate
and polyvinyl acetate phthalate; carboxymethylcellulose; methyl-
25 cellulose phthalate, succinate, phthalate succinate and hemi-
phthalate, ethyl~ se and ethylcellulose succinate; shellac;
ethylcarboxyethylcellulose; methacrylate/maleic anhydride copoly-
mer; maleic anhydride/vinyl methyl ether copolymer; styrene/
maleic acid copolymer3; 2-ethylhexyl acrylate/maleic anhydride,
30 crotonic acidtvinyl acetate copolymer; carboxymethylethylcellu-
lose glycerol monooctanoate; r~ 11 ose acetate succinate; poly-
ethylene, polypropylene and copolymers of ethylene or propylene
with acrylates and methacrylates and also acrylic acid and meth-
acrylic acid.
Aqueous wax dispersions are advantageously employed as coating
~ubstances, 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 -olefinically unsaturated mono-
40 or dicarboxylic acid having 3 to 8 C atoms and from 90 to 75t byweight 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 an MFI value, measured at 160 C
and 325 p, of from 1 to 600, from 0.1 to 5& by weight of alkali
45 metal hydroxide, ammonia, an ~lkAnolAmino or a ~l;AlkAnolAm;n~ and
their mixtures and, as the .. -; nr3rr~ water to 100% .
___ _ __ _
0050/44517
7 2~7918
The copolymers of ethylene to be used for the wax dispersions
contain from 10 to 25, preferably from 15 to 24, ~ by weight of
C-ol~f;n;cAl1y unsaturated mono-- or dicarboxylic acids having 3
to 8 C atoms, of which, for example, acrylic acid, methacrylic
5 acid, crotonic acid, maleic 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
10 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 t- .ILuLe through a nozzle of specific
dimensions with a specific expenditure of force (loading~. The
determination of the melt indices (MFI units) is carried out
15 according to the following standard ~Lu~:dur~s, 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, namely, as
20 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 tr;AlkAnr~1Am;n~ in each case
having from 2 to 18 C atoms in the hydroxyalkyl radical, prefer-
ably from 2 to 6 C atoms, or mixtures of the AlkAn~-lAm;n~Q men-
25 tioned or a dialky1n~n~A1kAnolamine in each case having from 2 to8 C atoms in the alkyl or hydroxyalkyl radical, or their mix-
tures. Amines which may be mentioned are, for example, diethanol-
amine, triethAn~l ;n~ 2-amino--2-methylpropanol or dimethyl-
ethanolamine. Ammonia is preferably used.
t~wing to the base content in the wax dispersions, the carboxylic
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 859~.
One or more of the coating substances mentioned can be used for
the coating layer. The coating layer can additionally contain
substances for controlling the release of the active ~Q.
These are eg. water-soluble substances such as polyethylene gly-
40 cols, polyvinylpyrrolidone, or copolymers of polyvinylpyrrolidoneand polyvinyl acetate. The amount thereof iB, for example, from
0.1 to 5% by weight, preferably from 0.1 to 396 by weight, based
on the coating 3ubstance.
45 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 ~ater. An
0050/44517
2 ~ 79 1 8 t
8
a~ueous suspension or an emulsion of the coating substance is
preferably used which ha~, 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
5 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 596 by
10 weight of ammonia and from 55 to 94.9% by weight of water or con-
sists of the8e components, thQ ethylene copolymer wax being com-
posed of from 75 to 90~ by weight of ethylene units and of from
10 to 251; by weight of units of an ~ f~n;c~lly unsaturated
mono-- or dicarboxylic acid having 3 to 8 carbon atoms.
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
20 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
25 compound.
However, it can also be advantageous additionally to apply active
compound from outside to these compositions. The flln~ Al com-
positions thus obtained enable a further graduation of the con-
30 trolled release of active compound, the active _ ` appliedto the coating layer on the outside being important for a more
specific initial action. It may :~A~l;t;~ lly be advantageous also
to use a second coating layer, by means of which a further possi-
bility of control for the delayed release of the active
35 results.
In addition to th~ coating technique described above, there is a
further advantageous technique for the production of the fungi-
cidal compositions according to the invention in a formulation
40 having delayed release of active compound in which the active
c _ .iq are incorporated into suitable matrix substances from
which the active ~ _ ~- are relQased in a delayed and con-'
trolled manner. The matrix used in this case can be, for example,
the material employed for the coating. Preparation is expediently
45 carried out here by dissolving or dispersing the active ~
in the solution or dispersion of the coating material and then
applying this preparation, as described above for the coating
_ _ _ _ _ _ .
0050/44517
2179181
g
substances, to the carrier material. It is ensured by this means
that the active flC are dispersed uniformly in the coating
layer. As a rule, release from these formulations i8 diffusion-
controlled .
The fungicidal compositions in general contain from 0.01 to gS,
preferably from 0.05 to 90, 96 by weight of active compound (a)
and (b).
10 D~rF~n~;n~ on the effect desired, the application rates are from
0.02 to 5 kg, preferably from 0.05 to 3 kg, of active ~ '-
( a ) and ( b ) per ha . The ratio of active compound ( a ) to active
compound (b) in the flln~ l mixture in this case is in general
from 50:1 to 1:10, preferably from 20:1 to 1:5, in particular
15 from 10:1 to 1:2.
The mixtures are distinguished by an outstanding activity against
a broad spectrum of phytopathogenic fungi, in particular from the
Ascomycetes and R~q; ~ es classes .
They are of particular importance for the control of a multiplic-
ity of fungi on various crop pIants such as cereals, eg. wheat,
rye, barley, oats, rice, rape, sugar beet, corn, soybeans, cof-
fee, sugar cane, decorative plants and vegetable plants such as
25 cucumbers, beans and cucurbits. The f~lns;~ q according to the
invention are used with particular advantage for fungal control
on cereals.
The fungicidal compositions according to the invention are expe-
30 diently applied by allowing the fungicidal composition to act inor on the soil on the seed planted in the soil and the plants de-
veloping therefrom or on s~ ; nqq . The application of the fungi-
cidal composition and the planting of the seed or the planting of
the seedlings can take place in separate operations, it being
35 possible for the application of the f1lng;~ l composition to
take place before or after the planting of the seed or the plant-
ing of the seedlings.
It is particularly advantageous to apply the formulated active
40 ~ , ~lq (a) and (b) together with the seed or the planting of
the seedlings.
The following exam~les illustraee the invention.
-
0050/44517
0 2179t8t
A. Examples of formulations according to the invention
c) The active compound ~nY; nnn~ ~nl ~ was processed in the
form of a suspension concentrate of the following com-
pOSition:
500 g/l of ~pnY; ron:~7n~
30 g/l of 2 block copolymer having a polypropylene
oxide core of approximate ~ r weight 3250,
to which ethylene oxide up to a molecular weight
of approximately 6500 is grafted as a dispersant
( BASF, Germany ),
20 g/l of a sodium salt of a condensation product of
phenolsulfonic acid, urea and formaldehyde as a
di~persant (BASF, Germany) and
the difference to 1 1 of water. The litIuid
preparation~ of epoxiconazole used in the
following examples were obtained by diluting
thi~ suspension concentrate with the appropriate
amount o~ water.
2~ ,3) The active compound fenpropimorph was pIo- e3~d as an
oil-in-water emul~ion of the following composition:
200 g/l of fenpropimorph,
37 g/l of a p--isononylphenol etherified with 8 ethylene
oxide units as an ~mlll~;f;~r (BA3F, Germany),
87.5 g/lof a 1:1 mixture (weight) of 2--ethylh~Y5nn~
acid and a p--isononylphenol eth~r; f; ~d with 7
ethylene oxide units as an emul~ifier (BASF,
Germany ) and
the difference to 1 1 of water.
40 Example 1
a) Application of ~p~Y; c~n~7nl ~ to NP ~ertilizer
A solution of 3.0 g of epoxiconazole, prepared according to
(c~), were [ ~ic ] ~prayed onto 4 kg of a nitrogen/pho3phate
fertilizer (Nitrophoska~) fertilizer 20-20-0, BASF) with a
particle size in the range 2-3 . 5 mm and a bulk weight of
0050/44517
11 ' ' 2 ~ 7~ ~ 8 l
1050 g/l 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 Na2S2Os and 69.10% by weight of
water. A mixture of 740 g of this wax dispersion and 100 ml
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 ~ ; nn 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 .
25 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 ~.r~Yi~n~7nle as described
30 in Example la) 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.
35 Example 3
The ~L~e~uL~ 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
40 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.
-
0050/44517
2 1 79 1 8 t
12Example 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 ~ertilizer
(~itrophoska~9 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
2796 by weight of an ethylene/acrylic acid copolymer compris-
ing 209~ by weight of acrylic acid and 80% by weight of ethyl-
ene, 3.68% by weight of a_monia solution (25& strength by
weight), 0.20~ by weight of Na2520s and 69.1096 by weight of
water. A mixture of 713 g of this wax dispersion and 96 ml of
water was sprayed in a fl-l;c;;?ed bed coating apparatus onto
3. 8 kg of the fertilizer granules treated with fenpropimorph
(according to (,~), see above) as described in section a)
above and warmed to 45 C with admission of air at from 40 to
42 C over a period o_ 62 min. Drying was then carried out for
a further 5 min with ~urther ~m; r~ n of air at from 40 to
42 C. The content of the coating layer in the coated ferti-
lizer granules obtained after drying was about 5~ by weight,
based on the coated fertilizer granules.
3 0 Example 5
The ~Lv~eduL-_ was as d~sr~r;h~d 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
35 ~ r; hed 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.
Example 6
The ~Iocadu-~ was as describQd in Example 4b), but 2.142 kg of
the wax dispersion were spr~yed onto 3.4 kg of the fertilizer
45 granules treated with fenpropimorph as described in Example 4a)
at an air inlet and air outlQt temperature of 44-45 C, the total
time for the spraying and the subsequent drying being 190 min.
_ .. .. _ . _ .. . .. . _ . _.. , .. , . , ~, _ _ _ _ __ ___
0050/44517
13 2179~81
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 Pr-tY;r~nA7Ol-~ (according to (), see above) and
lO the other an oil-in-water emulsion of 15 g of fenpropimorph.
After drying, the granules treated in this way were treated cor-
r~pon~;n~ to the spraying ~LvcecluLe 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
20 lb). Using this preparation, 3.8 kg of NP 20-20-0 fertilizer
granules were coated as in Ex. lb) (45 C air inlet ~ ,_L~L~.UL~
52 min application time).
Example 9
The pLvceduLe was as in Example 8, only instead of 15 g of fen-
propimorph 2.5 g of eroY;ct~n~7^l0 (according to (c), see above)
were stirred in as such.
30 Example 10
The pLV'_edULe was as in Example 8, only in addition to the 15 g
of fenpropimorph 2.5 g of ~po~;c~n~7~ (according to (), see
above ) werQ 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-
40 lizer granules, but instead of the wax dispersion described aboveusing an aqueous polymer dispersion (of the type Acronal~, BASF)
which consisted to 6096 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
45 parameters can be seen from the following table. The inlet air
tQmperature in all cases was 40 - 45-C.
.
0050/44517
2 1 79 ~ 8 ~
14
Ex.No.Fenpropimorph Fr~lr; c~nA701e Acronal TLme for
as pure accor~ing to (40% 6trength) spraying
substance (a)
[g] [g]
511 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
1015 15 2.5 500 g 49 min
16 15 2.5 1000 g 87 min
The amount of coating in the finished granules was 59~ by weight
each in Examples 11, 13 and 15, and 10% by weight each in Exam-
15 ples 12, 14 and 16. The product was subsequently also powdered ona disk with 0 . 25% by weight of talc .
Examples 17 - 22
20 Examples 17 -- 22 were carried out in a gimilar manner to Examples
11 - 16, but the active '- 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 ~ln-hAn~c~d.
Examples 23 and 24
Examples 23 and 24 were carried out in a similar manner to Exam-
ples 11 and 13, but the support material used was 2.0 kg of pum-
30 ice split having a particle size of 2 . 0 - 3 . 5 mm and a bulk
weight of 460 g/l. On account of the lower density of the pumice
split, the co~ting amount in the finished product was in this
case 1096 by weight.
3 5 Examples 25 - 3 0
Examples 25 -- 30 ~ULLe~ d in their implementation to the
examples described above as follows: Example 25 ouLLe~u,.ds to
Example 11, Example 26 ~uLL-~ul~ds to Example 17, Example 27 cor-
40 responds to Example 13, Example 28 corresponds to Example 19,Example 29 ~:ULLe~ dS 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
thQ type Eu-Grit 8/10) having a particle si_e of 2.0 - 3.15 mm
45 and a bulk weight of 450 g/l was used as the carrier material.
The amount of coating substance was also 10% by weight here
because of the lower bulk weight. The air inlet temperature was
. .. _ _ . .. ... . .. . .
0050/44517
2~7918~
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 3 1
Corresponding to Example 7, solutions of 7 . 5 g of ~enpropimorph
(according to (~), see above) and of 1.25 g of epoxiconazole
~according to (a), see above) in 38.75 g of water were first ap-
plied to 3. 8 kg of NP 20-20-0 fertilizer and dried. A mixture of
10 500 g of the Acronal dispersion described in Examples 11 - 16,
5 g of fenpropimorph (according to (,~), see above) and 0.83 g of
p~Y;c~nA7ole (according to (), see above) was then applied as a
coating and dried (time: 45 min, temp.: 45 C inlet air). Finally,
301utions of 2.5 g of fenpropimorph (according to (,~), see above)
15 in 10.8 g of water and 0.42 g of ~pAY;r~rA7A~ (according to (a),
see above ) were again applied to the coating on the outside. The
finished product contains 59~ by weight of coating material and
half of the active ~ are dispersed under the coating, a
third in the coating matrix and a sixth on the outside on the
20 coating.
Example 32
This example was carried out in a similar manner to Example 31,
25 but instead of the Acronal dispersion 740 g of the wax dispersion
described in Example lb) were used (time: 55 min, temp.: 50 C).
The product contained 59~ by weight of coating material and has
the active compound distribution shown in Example 31.
30 Example 33
The example was carried out in a similar manner to Example 31.
E~owever, the individual application rates of the active ~ ~~
were varied such that their distribution in the finished product
35 changed such that one third of the active ~ ~c were applied
under the coating and two thirds were embedded in the coating
material .
Example 3 4
This example was carried out in a similar manner to Example 33,
but 740 g of the wax dispersion as ~3~s~r; h~ in Example lb were
used as coating material.
.
-
0050/44S17
2179181
16
Example 35
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-
5 scribed in Examples 25 - 30 were used as carrier granules. Be-
cause of the lower bulk weight, in this case a coating amount of
10% by weight again resulted in the finished product. Active com-
pound dispersion was carried out by applying two thirds under the
coating layer and '-; n~ one third in the coating layer.
B. Use examples
Testing of the fungicide granules having delayed release of ac-
tive compound for the control of seed- and airborne harmful fungi
15 on cereals
Fungicide granules having delayed release of active compound were
mixed with winter wheat seed of the variQty Rektor such that dur-
ing simultaneous sowing of 200 kg~ha of loose smut- and covered
20 smut-infected wheat and [sic] 100 kg/ha of th~ fungicide granules
according to the invention were applied to the same drill row
using a drilling machi~e. The amounts of active compound were,
per ha, 300 g of fenpropimorph or 50 g of epoxiconazole or, on
combination of both active c ~c, 125 g of fenpropimorph and
25 25 g of epoxiconazole ~Use Example 1 ) . 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,
30 100 = 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-
35 ing delayed release of active compound in the same manner as withthe wheat seed. 200 kg/ha of barley and 200 kg/ha of the fungi-
cide granules according to the invention were sown simul-
taneously. The amount of active compound per ha was 750 g of fen-
propimorph or 125 g of ~rnY; ~ n~7~ or, in combination, 375 g of
40 fenpropimorph and 125 g of ~r~Yirr~n~7ole (Use Example 2). At the
end o~ the barley blooming period (development stage 69), attack
by mildew (Erysiphe graminis ) and net blotch (Pyrenophora teres )
was determined as total plant attack and the effect of the fungi-
cide granules was converted into C~ft~ nri~s according to
45 Abbott. USQ Example 2 shows the results of this test.
0050/44517 17 2 ~ 7 9 ~ ~ ~
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