Note: Descriptions are shown in the official language in which they were submitted.
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F I L E, ~ttd~-~I T H I S A idfEH~E~B-
'~E'XT TRANSLATION
Fungicidal active compound combinations
The present invention relates to novel active compound combinations which
comprise
known halogeno-benzimidazoles and further known fungicidally active compounds,
and
which are highly suitable for controlling phytopathogenic fungi.
It is already known that 1-(3,5-dimethyl-isoxazole-4-sulphonyl)-2-bromo-6,6-
diffuoro-
[1,3]-dioxolo-[4,Sf]-benzimidazole and 1-(3,5-dimethyl-isoxaole-4-sulphonyl)-2-
chloro-
6,6-difluoro-[1,3]-dioxolo-[4,SfJ-benzimidazole have fungicidal properties
(cf. WO 97-
06171 ). The activity of these compounds is good; however, at low application
rates it is in
some cases not satisfactory.
Furthermore, it is already known that a large number of triazole derivatives,
aniline
derivatives, dicarboximides and other heterocycles can be employed for
controlling fungi
(cf. EP-A 0 040 345, DE-A 2 201 063, DE-A 2 324 0 10, Pesticide Manual, 9th
Edition
(1991), pages 249 and 827, EP-A 0 382 375 and EP-A 0 S15 901). Likewise, the
activity
of these compounds is not always satisfactory at low application rates.
Finally, it is also known that 1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-
imida-
zolidineimine can be used for controlling animal pests such as insects (cf.
Pesticide
Manual, 9th Edition (1991), page 491). However, fungicidal properties have not
hitherto
been described for this compound.
It has now been found that the novel active compound combinations consisting
of a
halogeno-benzimidazole of the formula
Z
N
O ~ N
H3C S02
N/ ~ (I)
O CH3
in which
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Z represents chlorine or bromine,
and
( 1 ) a triazole derivative of the formula
X / \ O-CH-Y-C(CH3)s
(II),
N
N
in which
X represents chlorine or phenyl, and
-C- -CH-
Y represents O or OH ,
and/or
(2) the triazole derivative of the formula
OH
CI ~ \ CHZ CH2 C-C(CH3)s
CH2 (III),
,N
N
(tebuconazole)
and/or
(3) an aniline derivative of the formula
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R' ~ ~ N/S CCIZF
(IV),
~S02 N(CH3)2
in which
RI represents hydrogen or methyl,
S
and/or
(4) N-[1-(4-chloro-phenyl)-ethyl]-2,2-dichloro-1-ethyl-3-methyl-cyclopropane-
carboxamide of the formula
CI CI
CI ~ \ CH-NH-C H
C2Hs CH3
CH3 O
and/or
(5) the zinc propylene-1,2-bis(dithiocarbamidate) of the formula
H3
-[Zn-S-C-NH-CH2 CH-NH-C-S]~
NI)
n > = 1 (propineb)
and/or
(6) at least one thiocarbamate of the formula
H S
N--
S
S~Me (VII),
N
H S
Me = Zn or Mn or a mixture of Zn and Mn
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and/or
(7) the aniline derivative of the formula
O
CI NH ~ ~ OH (VIII)
CH3
CI CI
(fenhexamide)
and/or
(8) the compound of the formula
i H(CH3)2
(CH3)2CH-O-C-NH-CH-C-NH-CH ~ ~ CH3 (IX)
()
O CH3
and/or
(9) the benzothiadiazole derivative of the formula
N
II (X)
H3CS-C SAN
O (bendicar)
and/or
(10) the 8-t-butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-1,4-dioxaspiro[5,4]-
decane of
the formula
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_5_
O
(CH3)3C (xl)
O CH N~CZHS
~C3H~ n
(spiroxamine)
and/or
( 11 ) the compound of the formula
~N\C~I ~ \
o~o ~ (xll)
CN H3CO~C \ OCH3
I I
O (azoxystrobin)
and/or
( 12) the compound of the formula
CH3 ~ \
O
~CHZ ~ (X111)
\ H3CO~C wN~OCH3
I I
O (kresoxim-methyl)
and/or
( 13) the compound of the formula
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CI
O F ~ ~ N-O
- / (XIV)
NON O N/ O
OC H3
and/or
( 14) the cyanooxime derivative of the formula
S
O O CN
CH3 CHZ NH-C~-NH-IC-C=NOCH3 (XV)
(cymoxanil)
and/or
(15) a pyrimidine derivative ofthe formula
CH3
N
NH~~ ~ (XVI),
N-
Rz
in which
R2 represents methyl or cyclopropyl,
and/or
(16) the aniline derivative ofthe formula
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CH3 i Hs
/CH-COOCH3
N ~ (XVI I)
CH2 O-CH3
CH3 O
(metalaxyl)
and/or
(17) the morpholine derivative of the formula
o / ~ cl
O N-CI-CH=C
(XVI I I)
/ ~ OCH3
(dimetomorph)
OCH3
and/or
(18) the phthalimide derivative ofthe formula
O
C
~N-S-CCI3 (XIX)
C
(fol pet)
O
and/or
( 19) the phosphorus compound of the formula
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_g_
and/or
HSC20 / O
H/P\O AI (XX)
(fosetyl-AI)
S (20) the hydroxyethyl-triazole derivative of the formula
CI
OH
CH2 C~CI (XXI)
i Hz
N~N~S
~NH
and/or
(21) the 1-[(6-chloro-3-pyridinyl)-methyl]-N-vitro-2-imidazolidineimine of the
formula
\ CH2 N NH (XXII)
CI N ~ ~ NO
z
(imidacloprid)
and/or
(22) the oxazolidinedione of the formula
CH3
O
- O~N~O (XXIII)
I
(famoxadone)
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and/or
(23) the benzamide derivative of the formula
CI
Hs
H3C C-NH- ~ I I CH2CI (XXI~
CI C2H5 O
and/or
(24) a guanidine derivative of the formula
Rs Rs
R3 N-(CH2)e [ ~ -(CHZ)8Jm N-H (XX~
H
x (2 + m) CH3COOH
in which
m represents integers from 0 to 5 and
R3 represents hydrogen (17 to 23%) or the radical of the formula
-C=NH
(77 to 83 %)
NH2
and/or
(25) the triazole derivative of the formula
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CI ~ ~ CH-C3H~ n
H (XXVI)
2
,N
(penconazole)
N
have very good fungicidal properties.
Surprisingly, the fungicidal activity of the active compound combinations
according to the
invention is considerably higher than the sum of the activities of the
individual active
compounds. Thus, an unforeseeable, true synergistic effect is present, and not
just an
addition of activities.
The formula (I) includes
- the 1-(3,5-dimethyl-isoxazole-4-sulphonyl)-2-bromo-6,6-difluoro-[1,3]-
dioxolo-
[4,SfJ-benzimidazole of the formula
O / N
O ~ N
1
H3C S02 (la)
N/
.O~CH3
and
- the 1-(3,S-dimethyl-isoxazole-4-sulphonyl)-2-chloro-6,6-difluoro-[1,3]-
dioxolo-
[4,Sf]-benzimidazole ofthe formula
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O / N
~>---CI
O ~ N
1
H3C S02 (Ib).
N/
'O~CH3
The halogeno-benzimidazoles of the formulae (Ia) and (Ib) are known (cf. WO 97-
06171 ).
The formula (II) includes the compounds
1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one ofthe
formula
O
CI ~ ~ O-CH-~ ~-C(CH3)s
U
(Ila)
N'
C ~N (triadimefon)
N
1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ole ofthe
formula
OH
CI ~ ~ O-CH- ~ H-C(CH3)s
(Ilb)
N'
(triadimenol)
and
1-(4-phenyl-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ole of the
formula
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OH
O-CH-CH-C(CH3)s
(Ilc)
N~
(bitertanol)
The formula (IV) includes the aniline derivatives of the formulae
S-CCI2F
N ~ (IVa)
~S02 N(CH3)2 (dichlofluanid)
and
/SCC12F
H3C~N~ (IVb)
S02 N(CH3)2 (tolylfluanid)
It is evident from the formula for the active compound of the formula (V) that
the
compound has three asymmetrically substituted carbon atoms. The product may
therefore
be present as a mixture of various isomers, or else in the form of a single
component.
Particular preference is given to the compounds
N-(R)-[1-(4-chloro-phenyl)-ethyl]-(1S)-2,2-dichloro-1-ethyl-3t-methyl-lr-cyclo-
propanecarboxamide of the formula
cl cl (R)
H CO-NH-CH ~ \ CI
(Va)
H3C C2H5 CH3
(S) (R)
and
N-(R)-[ 1-(4-chloro-phenyl)-ethyl]-( 1 R)-2, 2-dichloro-1-ethyl-3 t-methyl-1 r-
cyclo-
propanecarboxamide of the formula
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CI CI
H3C~ C2H5 (R)
H CO-NH-CH ~ ~ CI (Vb)
(S) (R) ~ Hs
The formula (VII) includes the compounds
(VIIa) Me = Zn (zineb)
(VIIb) Me = Mn (maneb) and
(VIII) mixture of (VIIa) and (VIIb) (mancozeb).
The formula (XVI) includes the compounds
(XVIa) R2 = CH3 (pyrimethanil) and
(XVIb) RZ _ ~ (cyprodinyl)
The hydroxyethyl-triazole derivative of the formula (XXI) can be present in
the "thiono"
form of the formula
CI
OH
CH2 C~CI
H2 (XXI)
~N~S
~N
L--NH
or in the tautomeric "mercapto" form of the formula
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CI
OH
CH2 C-~CI
H2 (XXIb)
N~N SH
N
For the sake of simplicity, only the "thiono" form is given in each case.
The guanidine derivative of the formula (XX~ is a substance mixture of the
common
name guazatine.
The components which are present in the active compound combinations according
to the
invention in addition to a halogeno-benzimidazole of the formula (I) are also
known.
Specifically, the active compounds are described in the following
publications:
(1) Compounds ofthe formula (II)
DE-A 2 201 063
DE-A 2 324 010
(2) Compound of the formula (III)
EP-A 0 040 345
(3) Compounds ofthe formula (I~
Pesticide Manual, 9th Edition (1991), pages 249 and 827
(4) Compound of the formula (~ and individual derivatives thereof
EP-A 0 341 475
(5) Compound of the formula (VI)
Pesticide Manual, 9th Edition (1991), page 726
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(6) Compounds of the formula (VII)
Pesticide Manual, 9th Edition (1991), pages 529, 531 and 866
(7) Compound of the formula (VIII)
EP-A 0 339 418
(8) Compound of the formula (I~
EP-A 0 472 996
(9) Compound of the formula (~
EP-A 0 313 512
( 10) Compound of the formula (XI)
EP-A 0 281 842
( 11 ) Compound of the formula (XII)
EP-A 0 382 375
(12) Compound of the formula (XIII)
EP-A 0 S 15 901
( 13) Compound of the formula (XIV)
DE-A 196 02 095
( 14) Compound of the formula (XU)
Pesticide Manual, 9th edition (1991), page 206
( 15) Compounds of the formula (XVI)
EP-A 0 270 111
EP-A 0 310 550
(16) Compound ofthe formula (XVII)
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Pesticide Manual, 9th Edition (1991), page 554
( 17) Compound of the formula (XVIII)
EP-A 0 219 756
(18) Compound of the formula (XI~
Pesticide Manual, 9th Edition (1991), page 431
( 19) Compound of the formula (X~
Pesticide Manual, 9th Edition (1991), page 443
(20) Compound of the formula (XXI)
WO 96-16048
1 S (21 ) Compound of the formula (X~I)
Pesticide Manual, 9th Edition (1991), page 491
(22) Compound of the formula (X~~II)
EP-A 0 393 911
(23) Compound of the formula (XXIV)
EP-A 0 600 629
(24) Substance of the formula (XX~
Pesticide Manual, 9th Edition (1991), page 461
(25) Compound of the formula (XXVI)
Pesticide Manual, 9th Edition (1991), page 654
3 0 In addition to an active compound of the formula (I), the active compound
combinations
according to the invention comprise at least one active compound of the
compounds of
groups (1) to (25). Additionally, they may comprise further fungicidally
active
components.
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The synergistic effect is particularly pronounced when the active compounds in
the active
compound combinations according to the invention are present in certain weight
ratios.
However, the weight ratios of the active compounds in the active compound
combinations
can be varied within a relatively wide range. In general,
0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight, of active
compound of
group ( I ),
0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight, of active
compound of
group (2),
1 to 150 parts by weight, preferably I to 100 parts by weight, of active
compound of
group (3),
0. I to 10 parts by weight, preferably 0.2 to 5 parts by weight, of active
compound of
group (4),
I to 150 parts by weight, preferably S to 100 parts by weight, of active
compound of
group (5),
1 to 150 parts by weight, preferably 5 to 100 parts by weight, of active
compound of
group (6),
0.1 to SO parts by weight, preferably 1 to 20 parts by weight, of active
compound of group
(7),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active
compound of
group (8),
0.02 to 50 parts by weight, preferably 0.1 to 10 parts by weight, of active
compound of
group (9),
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0.1 to 20 parts by weight, preferably 0.5 to 10 parts by weight, of active
compound of
group ( 10),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active
compound of
group ( 11 ),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active
compound of
group ( 12),
0. I to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active
compound of
group ( 13 ),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active
compound of
group ( 14),
0.2 to 50 parts by weight, preferably 1 to 20 parts by weight, of active
compound of group
(15),
0.1 to SO parts by weight, preferably 0.2 to 20 parts by weight, of active
compound of
group (16),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active
compound of
group ( 17),
1 to 150 parts by weight, preferably 5 to 100 parts by weight, of active
compound of
group (18),
0.1 to 150 parts by weight, preferably 1 to 100 parts by weight, of active
compound of
group (19),
0.02 to 50 parts by weight, preferably 0.2 to 10 parts by weight, of active
compound of
group (20),
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0.05 to 20 parts by weight, preferably 0.1 to 10 parts by weight, of active
compound of
group (21 ),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active
compound of
group (22),
0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, of active
compound of
group (23 ),
0.02 to 50 parts by weight, preferably 0.04 to 10 parts by weight, of active
compound of
group (24) and/or
0.2 to 50 parts by weight, preferably 1 to 20 parts by weight, of active
compound of group
(25)
are employed per part by weight of active compound of the formula (I).
The active compound combinations according to the invention have very good
fungicidal
properties and can be employed for controlling phytopathogenic fungi, such as
Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes,
Basidiomycetes, Deuteromycetes, etc.
The active compound combinations according to the invention are particularly
suitable for
controlling cereal diseases, such as Erysiphe, Puccinia and Fusarium, and for
controlling
diseases encountered in viticulture, such as Uncinula, Plasmopara and
Botrytis, and
furthermore in dicotylendonous crops for controlling powdery and downy mildew
fungi
and causative organisms of leaf spot.
The fact that the active compound combinations are well tolerated by plants at
the
concentrations required for controlling plant diseases permits the treatment
of above-
ground parts of plants, of propagation stock and seeds, and of the soil. The
active
compound combinations according to the invention can be employed for foliar
application
or else as seed dressings.
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The active compound combinations according to the invention can be converted
to the
customary formulations, such as solutions, emulsions, suspensions, powders,
foams,
pastes, granules, aerosols and microencapsulations in polymeric substances and
in coating
S compositions for seeds, and LTLV formulations.
These formulations are produced in a known manner, for example by mixing the
active
compounds or active compound combinations with extenders, that is liquid
solvents,
liquefied gases under pressure, and/or solid Garners, optionally with the use
of surfactants,
that is emulsifiers and/or dispersants, and/or foam formers. If the extender
used is water, it
is also possible to use, for example, organic solvents as auxiliary solvents.
Essentially,
suitable liquid solvents include: aromatics such as xylene, toluene or
alkylnaphthalenes,
chlorinated aromatics or chlorinated aliphatic hydrocarbons such as
chlorobenzenes,
chloroethylenes or methylene chloride, aliphatic hydrocarbons such as
cyclohexane or
parafFlns, for example petroleum fractions, alcohols such as butanol or glycol
and their
ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl
isobutyl ketone or
cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl
sulphoxide, or else water. Liquefied gaseous extenders or carriers are to be
understood as
meaning liquids which are gaseous at ambient temperature and under atmospheric
pressure, for example aerosol propellants such as butane, propane, nitrogen
and carbon
dioxide. Suitable solid carriers are: for example ground natural minerals such
as kaolins,
clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous
earth, and ground
synthetic minerals such as finely divided silica, alumina and silicates.
Suitable solid carriers
for granules are: for example crushed and fractionated natural rocks such as
calcite,
marble, pumice, sepiolite and dolomite, or else synthetic granules of
inorganic and organic
meals, and granules of organic material such as sawdust, coconut shells, maize
cobs and
tobacco stalks. Suitable emulsifiers and/or foam formers are: for example
nonionic and
anionic emulsifiers, such as polyoxyethylene fatty acid esters,
polyoxyethylene fatty alcohol
ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl
sulphates,
arylsulphonates, or else protein hydrolysates. Suitable dispersants are: for
example lignin-
sulphite waste liquors and methylcellulose.
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Tackifiers such as carboxymethylcellulose and natural and synthetic polymers
in the form
of powders, granules or lances, such as gum arabic, polyvinyl alcohol and
polyvinyl
acetate, or else natural phospholipids such as cephalins and lecithins, and
synthetic
phospholipids can be used in the formulations. Other additives can be mineral
and
vegetable oils.
It is possible to use colourants such as inorganic pigments, for example iron
oxide,
titanium oxide and prussian blue, and organic dyestuffs such as alizarin
dyestuffs, azo
dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as
salts of iron,
manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations generally comprise between 0.1 and 95% by weight of active
compounds, preferably between 0.5 and 90%.
In the formulations, the active compound combinations according to the
invention can be
present as a mixture with other known active compounds such as fungicides,
insecticides,
acaricides and herbicides, and as mixtures with fertilizers or plant growth
regulators.
The active compound combinations can be used as such, in the form of their
formulations
or as the use forms prepared therefrom, such as ready-to-use solutions,
emulsifiable
concentrates, emulsions, suspensions, wettable powders, soluble powders and
granules.
They are used in the customary manner, for example by watering, spraying,
atomizing,
scattering, spreading, and as a powder for dry seed treatment, a solution for
seed
treatment, a water-soluble powder for seed treatment, a water-soluble powder
for slurry
treatment, or by encrusting.
When using the active compound combinations according to the invention, the
application
rates can be varied within a relatively wide range, depending on the kind of
application. In
the treatment of parts of plants, the application rates of the active compound
combination
are generally between 0.1 and 10,000 g/ha, preferably between 10 and 1000
g/ha. In the
treatment of seeds, the application rates of the active compound combination
are generally
between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g
per
kilogram of seed. In the treatment of the soil, the application rates of the
active compound
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combination are generally between 0.1 and 10,000 g/ha, preferably between 1
and
5000 g/ha.
The good fungicidal activity of the active compound combinations according to
the
invention is evident from the examples below. While the individual active
compounds
exhibit weaknesses with regard to the fungicidal activity, the combinations
have an activity
which exceeds a simple addition of activities.
A synergistic effect of fungicides is always present when the fungicidal
activity of the
active compound combinations exceeds the total of the activities of the active
compounds
when applied individually.
The expected activity for a given combination of two active compounds can be
calculated
as follows (cf. Colby, S.R., "Calculating Synergistic and Antagonistic
Responses of
Herbicide Combinations", Weeds 15, ( 1967), 20-22)
If
X is the efficacy when applying active compound A at an application rate of
Via,
Y is the efficacy when applying active compound B at an application rate of n
g/ha,
and
E is the efficacy when applying the active compounds A and B at application
rates of
m and n g/ha,
then
X~Y
E=X +Y-
100
The efficacy is calculated in %. 0% is an efficacy which corresponds to that
of the control,
while an efficacy of 100% means that no infection is observed.
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If the actual fungicidal activity exceeds the calculated value, then the
activity of the
combination is superadditive, i.e. a synergistic effect exists. In this case,
the efficacy which
was actually observed must be greater than the value for the expected efficacy
(E)
calculated from the abovementioned formula.
The examples that follow illustrate the invention.
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Examine 1
Phytophthora test (tomato) / protective
Solvent: 47 parts by weight of acetone
Emulsifier: 3 parts by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of
active
compound or active compound combination is mixed with the stated amounts of
solvent
and emulsifier and the concentrate is diluted with water to the desired
concentration, or a
commercial formulation of active compound or active compound combination is
diluted
with water to the desired concentration.
To test for protective activity, young plants are sprayed with the active
compound
preparation at the stated application rate. After the spray coating has dried
on, the plants
are inoculated with an aqueous spore suspension of Phytophthora infestans. The
plants are
then placed in an incubation cabinet at about 20°C and 100% relative
atmospheric
humidity.
Evaluation is carried out 3 days after the inoculation. 0% means an efFlcacy
which
corresponds to that of the control, while an efficacy of 100% means that no
infection is
observed.
Active compounds, application rates and test results are shown in the table
below.
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Table 1
Phytophthora test (tomato) / protective
Active compound Active compoundEfficacy
I application in
rate
I in g/ha
Known:
O / N
~ I 65
O
N
H3C SOz 0.2 14
N
.O CHs
(la)
F O / N
CI I 76
F O ~ N
H3C sot 0.2 37
N
.O CHs
{Ib)
/S-CCIZF
N
~SOZ N(CH3)2 2 0
(IVa)
/S CCIZF
~ ~
N
H C 2 26
3
~SO2 N(CH~2
{IVb)
N-// S
-~
~
S~ 2 17
S
~Zn
iMn +
c
-
S
S
~
~
H- \
H \
S
S
(Vllc)
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Table 1 (continued)
Phytophthora test (tomato) / protective
Active compound Active compound Efficacy
application rate in
in g/ha
S CH3 S
-[Zn-S-C-NH-CH2 CH-NH-C-S]~ 2 58
(VI)
O
2 12
C
~N-S-CCI3
C
O (XIX)
HSC20 / O
H jP~O AI 2 36
3
(
CH3
NH--~N 1 0
N /
CH3
(XVIa)
CH3
NH~N 1 0
N
(XVIb)
N N
'O I ~ 0.2 51
CN H3C0~ ~ OCH3
C
(XII) O
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Table 1 (continued)
Phytophthora test (tomato) / protective
Active compound Active compound Efficacy
application rate in
in g/ha
CH3 ~ \
O /
\ ~ H3CO~C wN~OCH3 0.2 0
\CH2
Ii
O
(X111)
CI
/ O F ~ ~ N-O 1 27
N~ '' O N
N
OCH3
(XIV)
CI
~N-C-CH=C 0.2 0
OCH3
(XVIII) OCH3
O O CN
CH3 CH2 NH-C-NH-C-C=NOCH3 0.2 0
(XV)
CH3 i Hs
/CH-COOCH3
NBC-CH2 O-CH3 0.2 0
CH3
(XVI I)
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Table 1 (continued)
Phytophthora test (tomato) / protective
Active compound Active compoundEfFicacy
application in
rate
in g/ha
CI
O
Hs
H3C C-NH-C C-CH2CI
0.2 0
C1 C2H5 O
(XXI~
I H(CH3)2
~ ~
(CH3)zCH-O-C-NH-CH-~ ~-NH- ~ I O
H
CHa
o cH3 0.2 0
(ix)
OH
O-CH- ~ H-C(CH3)s
0.2 24
N
(Ilc)
OH
CI ~ ' CH2 CH2 C-C(CH3)s
CHZ 0.2 0
,N
(III)
N
O
~ \
O-CH-C-C(CH3)s
CI
0.2 0
NON
(Ila)
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Table 1 (continued)
Phytophthora test (tomato) / protective
Active compound Active compound Efficacy
application rate in
in g/ha
OH
CI ~ \ O-CH-CH-C(CH3)3 0.2 0
N~
(Ilb)
CI
O
CHZ C~CI
0.2 0
i Hz
~N~ S
I) N
O
(CH3)3C
O CH-N~C2H5 0.2 5
~C3H7-n
(XI)
O
CI-NH ~ ~ OH 5 0
CH3
CI CI
(VIII)
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Table 1 (continued)
Phytophthora test (tomato) / protective
Active compound Active compound Efficacy
application rate in
in g/ha
CI CI (R)
H CO-NH-CH ~ ~ CI
H3C CZHS CH3
(S) (R) (Va)
1 0
CI CI
H3C' CzHS (R)
H .I. ' CO-NH-CH ~ ~ CI
(S) (R) CH3
(Vb)
(1:1-mixture)
CH2' NH 0.2 6
CI N- ~ NO
z
(XXI I)
According to the invention: found calc.*)
0.2
(la)
+ 54 14
(IVa) 2
(1:10)
(Ib) 0.2
+ 55 37
(IVa) 2 I
(1:10)
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Table 1 (continued)
Phytophthora test (tomato) / protective
Active compound Active compound Efficacy
application rate in
in g/ha
found calc. *)
(la) 0.2
+ 74 36
(IVb) 2
(1:10)
(Ib) 0.2
+ 86 53
(IVb) 2
(1:10)
(la) 0.2
+ 73 29
(VI Ic) 2
(1:10)
(Ib) 0.2
+ 70 48
(VI Ic) 2
(1:10)
(la) 0.2
+ 79 64
(VI) 2
(1:10)
(Ib) 0.2
+ 93 74
(VI) 2
(1:10)
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Table 1 (continued)
Phytophthora test (tomato) / protective
Active compound Active compound Efficacy
application rate in
in g/ha
0.2 found talc.*)
(Ib)
+ 71 45
(XIX) 2
(1:10)
(Ib) 0.2
+ 83 60
2
(1:10)
(I b) 0.2
+ 69 37
(XVIa)
(1:5)
(Ib) 0.2
+ 81 37
(XVIb)
(1:5)
(I b) 0.2
+ 87 69
(XII) 0,2
(1:1)
(la) 0.2
+ 71 14
(X111) 0,2
(1:1)
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Table 1 (continued)
Phytophthora test (tomato) / protective
Active compound Active compound Efficacy
application rate in
in g/ha
0.2 found calc. *)
i (Ib) + 75 37
(X111) 0,2
(1:1)
(I a) 0.2
+ 73 37
(XIV) 1
(1:5)
{Ib) 0.2
+ 75 54
(XIV) 1
(1:5)
{I a) 0.2
+ 46 14
(XVI I I) 0.2
(1:1)
(I b) 0.2
+ 81 37
(XVI I I) 0.2
(1:1)
(la) 0.2
+ 56 14
{XV) 0.2
(1:1)
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Table 1 (continued)
Phytophthora test (tomato) / protective
Active compound Active compound Efficacy
application rate in
in g/ha
0.2 found calc.*)
(Ib)
+ 67 37
(XV) 0.2
(1:1)
(la) 0.2
+ 73 14
(XVI I) 0.2
(1:1)
(I b) 0.2
+ 58 37
0.2
(XVI I)
(1:1)
(Ib) 0.2
+ 50 37
(~(I~ 0.2
(1:1)
(la) 1
+ + 82 65
(IX) 1
(1:1)
(Ib) 0.2
+ 67 37
(I X) 0.2
(1:1)
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Table 1 (continued)
Phytophthora test (tomato) / protective
Active compound Active compound Efficacy
application rate in
in g/ha
0.2 found calc. *)
(Ib)
+ 85 52
0.2
(Ilc)
(1:1)
(la) 0.2
+ 51 14
(I I I) 0.2
(1:1)
(Ib) 0.2
+ 71 37
0.2
(III)
(1:1)
(la) 0.2
+ 56 14
(I I a) 0.2
(1:1)
(Ib) 0.2
+ 84 37
(I la) 0.2
(1:1)
(la) 0.2
+ 67 14
0.2
(Ilb)
(1:1)
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Table 1 (continued)
Phytophthora test (tomato) / protective
Active compound Active compound Efficacy
application rate in
in g/ha
0.2 found talc.*)
(Ib)
+ 75 37
0.2
(Ilb)
(1:1)
(la) 0.2
+ 51 14
0.2
(1:1)
(Ib) 0.2
+ 69 37
0.2
(1:1)
(la) 0.2
+ 67 18
0.2
(XI)
(1:1)
(Ib) 0.2
+ 87 40
(XI) 0.2
(1:1)
(la) 1
+ + 90 65
(VIII) 5
(1:5)
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Table 1 (continued)
Phytophthora test (tomato) / protective
~I Active compound Active compound Efficacy
application rate in
in g/ha
found talc. *)
(Ib) 1
+ + 90 76
(VIII)
5
(1:5)
(la) 1
+ + 89 65
(VaNb)
1
(1:1)
(I b) 1
+ + 95 76
(VaNb) 1
(1:1)
(I a) 0.2
+ 73 19
(XXI I) 0.2
(1:1)
(Ib) 0.2
+ 90 41
(XXI I) 0.2
(1:1)
found = efficacy found
talc. = efficacy calculated using the Colby formula
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Example 2
Fusarium nivale test (triticale) / seed treatment
The active compounds are applied as dry seed dressings. These are prepared by
ex-
tending the respective active compound or the active compound combination with
ground minerals to give a finely pulverulent mixture which ensures uniform
distri-
bution on the seed surface.
To dress the seed, the infected seed together with the seed dressing is shaken
for
3 minutes in a sealed glass flask.
2 x 100 corns of triticale are sown at a depth of 1 cm in standard soil and
cultivated in
a greenhouse at a temperature of about 10°C and a relative atmospheric
humidity of
1 S about 95% in seed trays which receive a light regimen of 15 hours per day.
About 3 weeks after sowing, the plants are evaluated for symptoms. 0% means an
efficacy which corresponds to that of the control, while an efficacy of 100%
means
that no infection is observed.
Active compounds, application rates and test results are shown in the table
below.
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Table 2
Fusarium nivale test (triticale) / seed treatment
Active compound Active compound
application rateEfI'lcacy in
in
mg/kg of seed
Known:
(Ia) 100 . 26
(Ib) S00 0
100 0
(XXII) 100 0
(IX) 500 0
(VIII) 100 0
(IVb) 100 3
Mixtures accordingto the
in-
vention:
(Ia + VIII) 50 + 50 66
(1:1)
(Ib + XXII) 50 + 50 36
(1:1)
(Ib + IX) (1:1) 250 + 250 43
(Ib + VIII) 50 + SO 32
(1:1)
(Ib + IVb) (1:1) 50 + 50 75
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Example 3
Pythium sp. test (pea) / seed treatment
The active compounds are applied as dry seed dressings. These are prepared by
ex-
tending the respective active compound or the active compound combination with
ground minerals to give a finely pulverulent mixture which ensures uniform
distri-
bution on the seed surface.
To dress the seed, the infected seed together with the seed dressing is shaken
for
3 minutes in a sealed glass flask.
2 x 50 corns of seed are sown at a depth of 2 cm in compost soil naturally
infected
with phythium sp. and cultivated in a greenhouse at a temperature of about
20°C in
seed trays which receive a light regimen of 15 hours per day.
Evaluation is carried out after 14 days. 0% means an efFicacy which
corresponds to
that of the control, while an efficacy of 100% means that no infection is
observed.
Active compounds, application rates and test results are shown in the table
below.
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Table 3
Pythium sp: test (pea) / seed treatment
Active compound Active compound
application rateEfficacy in
in
mg/kg of seed
Known:
(Ia) S00 1
(Ib) 1000 4
(VIII) 1000 8
(IVb) 1000 42
500 37
Mixtures accordingto the
in-
vention:
(Ia + IVb) (l 250 + 250 55
: l)
(Ib + VIII) 500 + S00 38
(1:1)
(Ib + IVb) (1:1) 500 + 500 59
