U.S. patent application number 09/843396 was filed with the patent office on 2002-11-21 for fungicide active substance combinations.
Invention is credited to Dutzmann, Stefan, Jautelat, Manfred, Stenzel, Klaus.
Application Number | 20020173529 09/843396 |
Document ID | / |
Family ID | 7826916 |
Filed Date | 2002-11-21 |
United States Patent
Application |
20020173529 |
Kind Code |
A1 |
Dutzmann, Stefan ; et
al. |
November 21, 2002 |
Fungicide active substance combinations
Abstract
The novel active compound combinations comprising
2-[2-(1-chlorocyclopropy-
l)-3-(2-chlorophenyl)-2-hydroxypropyl]2,4-dihydro-[1,2,4]-triazole-3-thion-
e of the formula 1 and the active compound of groups (1) to (24)
listed in the description have very good fungicidal properties.
Inventors: |
Dutzmann, Stefan;
(Langenfeld, DE) ; Stenzel, Klaus; (Dusseldorf,
DE) ; Jautelat, Manfred; (Burscheid, DE) |
Correspondence
Address: |
BAYER CORPORATION
PATENT DEPARTMENT
100 BAYER ROAD
PITTSBURGH
PA
15205
US
|
Family ID: |
7826916 |
Appl. No.: |
09/843396 |
Filed: |
April 26, 2001 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
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09843396 |
Apr 26, 2001 |
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09402866 |
Oct 13, 1999 |
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Current U.S.
Class: |
514/383 ;
514/384 |
Current CPC
Class: |
A01N 43/30 20130101;
A01N 37/24 20130101; A01N 43/88 20130101; A01N 37/34 20130101; A01N
43/653 20130101; A01N 37/50 20130101; A01N 43/36 20130101; A01N
43/38 20130101; A01N 51/00 20130101; A01N 53/00 20130101; A01N
47/32 20130101; A01N 55/02 20130101; A01N 43/82 20130101; A01N
43/84 20130101; A01N 47/12 20130101; A01N 37/18 20130101; A01N
47/14 20130101; A01N 57/12 20130101; A01N 47/04 20130101; A01N
37/22 20130101; A01N 37/38 20130101; A01N 37/20 20130101; A01N
47/10 20130101; A01N 43/54 20130101; A01N 43/653 20130101; A01N
57/12 20130101; A01N 53/00 20130101; A01N 51/00 20130101; A01N
47/44 20130101; A01N 47/32 20130101; A01N 47/14 20130101; A01N
47/12 20130101; A01N 47/04 20130101; A01N 43/88 20130101; A01N
43/82 20130101; A01N 43/653 20130101; A01N 43/54 20130101; A01N
43/36 20130101; A01N 43/30 20130101; A01N 37/50 20130101; A01N
37/38 20130101; A01N 37/34 20130101; A01N 37/24 20130101; A01N
37/20 20130101; A01N 43/653 20130101; A01N 2300/00 20130101 |
Class at
Publication: |
514/383 ;
514/384 |
International
Class: |
A01N 043/64 |
Foreign Application Data
Date |
Code |
Application Number |
Apr 18, 1997 |
DE |
197 16 257.6 |
Claims
1. Fungicidal compositions, characterized in that they contain an
active compound combination consisting of
2-[2-(1-chlorocyclopropyl)-3-(2-chloro-
phenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione of
the formula 198and (1) a triazole derivative of the formula 199in
which X represents chlorine or phenyl and Y represents 200and/or
(2) the triazole derivative of the formula 201and/or (3) an aniline
derivative of the formula 202in which R.sup.1 represents hydrogen
or methyl, and/or (4)
N-[1-(4-chloro-phenyl)-ethyl]-2,2-dichloro-1-ethyl-3-methyl-cycloprop-
ane-carboxamide of the formula 203and/or (5) the zinc
propylene-1,2-bis-(dithiocarbamate) of the formula 204n>=1
(propineb) and/or (6) at least one thiocarbamate of the formula
205Me=Zn or Mn or a mixture of Zn and Mn and/or (7) the aniline
derivative of the formula 206and/or (8) the compound of the formula
207and/or (9) the benzothiadiazole derivative of the formula
208and/or (10) the
8-t-butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-1,4-dioxaspiro-[5,4]-decane
209and/or (11) the compound of the formula 210and/or (12) the
compound of the formula 211and/or (13) the compound of the formula
212and/or (14) the dicarboximide of the formula 213and/or (15) a
pyrimidine derivative of the formula 214in which, R.sup.2
represents methyl or cyclopropyl, and/or (16) the phenyl derivative
of the formula 215and/or (17) the morpholine derivative of the
formula 216and/or (18) the phthalimide derivative of the formula
217and/or (19) the phosphorus compound of the formula 218and/or
(20) a phenylpyrrole derivative of the formula 219in which R.sup.3
and R.sup.4 each represent chlorine or together represent a radical
of the formula --O--CF.sub.2--O--, and/or (21) the
1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidineimine of
the formula 220and/or (22) the phenylurea derivative of the formula
221and/or (23) the benzamide derivative of the formula 222and/or
(24) a guanidine derivative of the formula 223in which m represents
integers from 0 to 5 and R.sup.5 represents hydrogen (17 to 23%) or
the radical of the formula 224(77 to 83%)
2. Composition according to claim 1, characterized in that in the
active compound combinations the weight ratio of active compound of
the formula (I) to active compound of group (1) is between 1:0.1
and 1:20, active compound of group (2) is between 1:0.1 and 1:20,
active compound of group (3) is between 1:0.2 and 1:150, active
compound of group (4) is between 1:0.1 and 1:10, active compound of
group (5) is between 1:1 and 1:50, active compound of group (6) is
between 1:1 and 1:50, active compound of group (7) is between 1:0.1
and 1:50, active compound of group (8) is between 1:0.2 and 1:50,
active compound of group (9) is between 1:0.02 and 1:50, active
compound of group (10) is between 1:0.1 and 1:50, active compound
of group (11) is between 1:0.1 and 1:50, active compound of group
(12) is between 1:0.1 and 1:50, active compound of group (13) is
between 1:0.1 and 1:50, active compound of group (14) is between
1:0.1 and 1:50, active compound of group (15) is between 1:0.1 and
1:50, active compound of group (16) is between 1:1 and 1:50, active
compound of group (17) is between 1:1 and 1:20, active compound of
group (18) is between 1:1 and 1:50, active compound of group (19)
is between 1:1 and 1:50, active compound of group (20) is between
1:0.1 and 1:10, active compound of group (21) is between 1:0.05 and
1:20, active compound of group (22) is between 1:0.1 and 1:10,
active compound of group (23) is between 1:0.1 and 1:10 and active
compound of group (24) is between 1:0.1 and 1:10.
3. Method, for controlling fungi, characterized in that active
compound combinations according to claim 1 are applied to the fungi
and/or their habitat.
4. Use of active compound combinations according to claim 1 for
controlling fungi.
5. Process for preparing fungicidal compositions characterized in
that active compound combinations according to claim 1 are mixed
with extenders and/or surfactants.
Description
[0001] The present invention relates to novel active compound
combinations which consist of the known
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)--
2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione and further
known fungicidally active compounds, and which are highly suitable
for controlling phytopathogenic fungi.
[0002] It is already known that
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophen-
yl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione has
fungicidal properties (cf. WO 96-16 048). The activity of this
compound is good, however, at low application rates it is in some
cases not satisfactory.
[0003] 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), paces 249 and 827, U.S. Pat. No. 3,903,090 and EP-A 0 206
999) Likewise, the activity of these compounds is not always
satisfactory at loss application rates
[0004] Finally, it is also known that
1-[(6-chloro-3-pyridinyl)-methyl]-N-- nitro-2-imidazolidineimine
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.
[0005] It has now been found that the novel active compound
combinations comprising
[0006]
2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4--
dihydro-[1,2,4]-triazole-3-thione of the formula 2
[0007] and
[0008] (1) a triazole derivative of the formula 3
[0009] in which
[0010] X represents chlorine or phenyl
[0011] and
[0012] Y represents 4
[0013] and/or
[0014] (2) the triazole derivative of the formula 5
[0015] and/or
[0016] (3) an aniline derivative of the formula 6
[0017] in which
[0018] R.sup.1 represents hydrogen or methyl,
[0019] and/or
[0020] (4)
N-[1-(4-chloro-phenyl)-ethyl]-2,2-dichloro-1-ethyl-3-methyl-cyc-
lopropane-carboxamide of the formula 7
[0021] and/or
[0022] (5) the zinc propylene-1,2-bis-(dithiocarbamate) of the
formula 8
[0023] and/or
[0024] (6) at least one thiocarbamate of the formula 9
[0025] Me=Zn or Mn or a mixture of Zn and Mn
[0026] and/or
[0027] (7) the aniline derivative of the formula 10
[0028] and/or
[0029] (8) the compound of the formula 11
[0030] and/or
[0031] (9) the benzothiadiazole derivative of the formula 12
[0032] and/or
[0033] (10) the
8-t-butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-1,4-dioxaspi-
ro-[5,4]-decane of the formula 13
[0034] and/or
[0035] (11) the compound of the formula 14
[0036] and/or
[0037] (12) the compound of the formula 15
[0038] and/or
[0039] (13) the compound of the formula 16
[0040] and/or
[0041] (14) the dicarboximide of the formula 17
[0042] and/or
[0043] (15) a pyrimidine derivative of the formula 18
[0044] in which
[0045] R.sup.2 represents methyl or cyclopropyl,
[0046] and/or
[0047] (16) the phenyl derivative of the formula 19
[0048] and/or
[0049] (17) the morpholine derivative of the formula 20
[0050] and/or
[0051] (18) the phthalimide derivative of the formula 21
[0052] and/or
[0053] (19) the phosphorus compound of the formula 22
[0054] and/or
[0055] (20) a phenylpyrrole derivative of the formula 23
[0056] in which
[0057] R.sup.3 and R.sup.4 each represent chlorine or together
represent a radical of the formula --O--CF.sub.2--O--,
[0058] and/or
[0059] (21) the
1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidinei- mine of
the formula 24
[0060] and/or
[0061] (22) the phenylurea derivative of the formula 25
[0062] and/or
[0063] (23) the benzamide derivative of the formula 26
[0064] and/or
[0065] (24) a guanidine derivative of the formula 27
[0066] x(2+m)CH.sub.3COOH
[0067] in which
[0068] m represents integers from 0 to 5
[0069] and
[0070] R.sup.5 represents hydrogen (17 to 23%) or the radical of
the formula 28
[0071] (77 to 83%).
[0072] have very good fungicidal properties.
[0073] 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.
[0074] The 2-[2-(1-chlorocyclopropyl)-3
(2-chlorophenyl)-2-hydroxypropyl]--
2,4-dihydro-[1,2,4]-triazole-3-thione of the formula (I) is known
(cf. WO 96-16 048) The compound can be present in the ,,thiono,,
form of the formula 29
[0075] or in the tautomeric ,,mercapto,, form of the formula 30
[0076] For simplicity's sake, only the ,,thiono,, form is given in
each case.
[0077] The formula (II) includes the compounds
[0078]
1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butane-2-o-
ne of the formula 31
[0079]
1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol
of the formula 32
[0080] and
[0081]
1-(4-phenyl-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol
of the formula 33
[0082] The formula (IV) includes the aniline derivatives of the
formulae 34
[0083] and
[0084] 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
[0085]
N-(R)-[1-(4-chloro-phenyl)-ethyl]-(1S)-2,2-dichloro-1-ethyl-3t-meth-
yl-1r-cyclopropanecarboxamide of the formula 35
[0086] and
[0087]
N-(R)-[1-(4-chloro-phenyl)-ethyl]-(1R)-2,2-dichloro-1-ethyl-3t-meth-
yl-1r-cyclopropanecarboxamide of the formula 36
[0088] The formula (VII) includes the compounds
[0089] (VIIa) Me=Zn (zineb)
[0090] (VIIb) Me=Mn (maneb)
[0091] and
[0092] (VIIc) mixture of (VIIa) and (VIIb) (mancozeb).
[0093] The formula (XVI) includes the compounds
[0094] (XVIa) R.sup.2.dbd.CH.sub.3 (pyrimethanil)
[0095] and
[0096] (XVIb) R.sup.2= 37
[0097] (cyprodinyl)
[0098] The formula (XXI) includes the compounds
[0099] 4-(2,3-dichlorophenyl)-pyrrole-3-carbonitrile of the formula
38
[0100] and
[0101]
4-(2,2-difluoro-1,3-benzodioxol-7-yl)-1H-pyrrole-3-carbonitrile of
the formula 39
[0102] The guanidine derivative of the formula (XXV) is a mixture
of substances of the common name guazatine.
[0103] The components which are present in the active compound
combinations according to the invention in addition to the active
compound of the formula (I) are also known Specifically, the active
compounds are described in the following publications:
[0104] (1) Compounds of the formula (II)
[0105] DE-A 2 201 063
[0106] DE-A 2 324 010
[0107] (2) Compound of the formula (III)
[0108] EP-A 0 040 345
[0109] (3) Compounds of the formula (IV)
[0110] Pesticide Manual, 9th Edition (1991) pages 249 and 927
[0111] (4) Compound of the formula (V) and individual isomers
thereof
[0112] EP-A 0 341 475
[0113] (5) Compound of the formula (VI)
[0114] Pesticide Manual, 9th Edition (1991), page 726
[0115] (6) Compounds of the formula (VII)
[0116] Pesticide Manual, 9th Edition (1991), pages 529, 531 and
866
[0117] (7) Compound of the formula (VIII)
[0118] EP-A 0 339 418
[0119] (8) Compound of the formula (IX)
[0120] EP-A 0 472 996
[0121] (9) Compound of the formula (X)
[0122] EP-A 0 313 512
[0123] (10) Compound of the formula (XI)
[0124] EP-A 0281 842
[0125] (11) Compound of the formula (XII)
[0126] EP-A 0 382 375
[0127] (12) Compound of the formula (XIII)
[0128] EP-A 0 515 901
[0129] (13) Compound of the formula (XIV)
[0130] EP-A 196 02 095
[0131] (14) Compound of the formula (XV)
[0132] U.S. Pat. No. 3,903,090
[0133] (15) Compounds of the formula (XVI)
[0134] EP-A 0 270 111
[0135] EP-A 0 310 550
[0136] (16) Compound of the formula (XVII)
[0137] Pesticide Manual, 9th Edition (1991), page 159
[0138] (17) Compound of the formula (XVIII)
[0139] EP-A 0 219 756
[0140] (18) Compound of the formula (XIX)
[0141] Pesticide Manual, 9th Edition (1991), page 431
[0142] (19) Compound of the formula (XX)
[0143] Pesticide Manual, 9th Edition (1991), page 443
[0144] (20) Compounds of the formula (XXI)
[0145] EP-A 0 236 272
[0146] EP-A 0 206 999
[0147] (21 ) Compound of the formula (XXII)
[0148] Pesticide Manual, 9th Edition (1991), page 491
[0149] (22) Compound of the formula (XXIII)
[0150] DE-A 2 732 257
[0151] (23) Compound of the formula (XXIV)
[0152] EP-A 0 600 629
[0153] (24) Substance of the formula (XXV)
[0154] Pesticide Manual, 9th Edition (1991), page 461
[0155] In addition to the 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 (24).
Additionally, they may comprise further fungicidally active
components.
[0156] 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,
[0157] 0.1 to 20 parts by weight, preferably 0.2 to 10 parts by
weight, of active compound of group (1),
[0158] 0.1 to 20 parts by weight, preferably 0.2 to 10 parts by
weight, of active compound of group (2),
[0159] 0.2 to 150 parts by weight, preferably 1 to 100 parts by
weight, of active compound of group (3),
[0160] 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by
weight, of active compound of group (4),
[0161] 1 to 50 parts by weight, preferably 5 to 20 parts by weight,
of active compound of group (5),
[0162] 1 to 50 parts by weight, preferably 2 to 20 parts by weight,
of active compound of group (6),
[0163] 0.1 to 50 parts by weight, preferably 1 to 30 parts by
weight, of active compound of group (7),
[0164] 0.2 to 50 parts by weight, preferably 1 to 20 parts by
weight, of active compound of group (8),
[0165] 0.02 to 50 parts by weight, preferably 0.2 to 10 parts by
weight, of active compound of group (9),
[0166] 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by
weight, of active compound of group (10),
[0167] 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by
weight, of active compound of group (11),
[0168] 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by
weight, of active compound of group (12),
[0169] 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by
weight, of active compound of group (13)
[0170] 0.1 to 50 parts by weight, preferably 1 to 30 parts by
weight, of active compound of group (14),
[0171] 0.1 to 50 parts by weight, preferably 0.2 to 20 parts by
weight, of active compound of group (15),
[0172] 0.1 to 50 parts by weight, preferably 2 to 20 parts by
weight, of active compound of group (16),
[0173] 1 to 20 parts by weight, preferably 2 to 10 parts by weight,
of active compound of group (17),
[0174] 1 to 50 parts by weight, preferably 2 to 20 parts by weight,
of active compound of group (18),
[0175] 1 to 50 parts by weight, preferably 2 to 20 parts by weight,
of active compound of group (19),
[0176] 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by
weight, of active compound of group (20),
[0177] 0.05 to 20 parts by weight, preferably 0.1 to 10 parts by
weight, of active compound of group (21),
[0178] 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by
weight, of active compound of group (22),
[0179] 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by
weight, of active compound of group (23),
[0180] and/or
[0181] 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by
weight, of active compound of group (24)
[0182] are present per part by weight of active compound of the
formula (I)
[0183] 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.
[0184] 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
[0185] 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.
[0186] 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
compositions for seeds, and ULV formulations.
[0187] 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 carriers, 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 paraffins, 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, monitmorillonite 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, polyoxyetlhylene fatty alcohol ethers, for
example alkylaryl polyglycol ethers, alkyl-sulphonates, alkyl
sulphates, arylsulphonates, or else protein hydrolysates. Suitable
dispersants are: for example lignin-sulphite waste liquors and
methylcellulose.
[0188] Tackifiers such as carboxymethylcellulose and natural and
synthetic polymers in the form of powders, granules or latices,
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.
[0189] It is possible to use colorants 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.
[0190] The formulations generally comprise between 0.1 and 95% by
weight of active compounds, preferably between 0.5 and 90%
[0191] 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.
[0192] 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.
[0193] 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 combination are
Generally between 0.1 and 10,000 (g/ha, preferably between 1 and
5000 (g/ha.
[0194] 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.
[0195] 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.
[0196] 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).
[0197] If
[0198] X is the efficacy when applying active compound A at an
application rate of m g/ha,
[0199] Y is the efficacy when applying active compound B at an
application rate of n g/ha and
[0200] E is the efficacy when applying the active compounds A and B
at an application rate of m and n g/ha,
[0201] then 1 E = X + Y - X Y 100
[0202] The efficacy is calculated in %. 0% is an efficacy which
corresponds to that of the control, whereas an efficacy of 100%
means that no infection is observed.
[0203] 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.
[0204] The examples that follow illustrate the invention.
EXAMPLE 1
[0205] Sphaerotheca Test (Cucumber)/Protective
1 Solvent: 47 parts by weight of acetone Emulsifier: 3 parts by
weight of alkylaryl polyglycol ether
[0206] 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.
[0207] 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 Sphaerotheca
fuliginea The plants are then placed in a greenhouse at about
23.degree. C. and a relative atmospheric humidity of about 70%.
[0208] Evaluation is carried out 10 days after the inoculation. 0%
means an efficacy which corresponds to that of the control, whereas
an efficacy of 100% means that no infection is observed.
[0209] Active compounds, application rates and test results are
shown in the table below.
2TABLE 1 Sphaerotheca test (cucumber)/protective Active compound
application rate Active compound in g/ha Efficacy in % Known: 40
2.5 0.5 21 0 41 25 0 42 25 0 43 25 0 44 25 0 45 25 0 46 50 0 47 25
0 48 25 0 49 25 0 50 12.5 0 51 12.5 0 52 12.5 0 53 12.5 0 54 12.5 0
55 2.5 57 56 2.5 59 57 12.5 15 58 2.5 0 59 2.5 50 60 2.5 61 2.5 80
62 2.5 22 63 2.5 0 According to the invention: found calc *) 64 65
70 21 66 67 63 21 68 69 63 21 70 71 63 21 72 73 59 21 74 75 52 21
76 77 63 21 78 79 59 21 80 81 52 21 82 83 50 21 84 85 63 21 86 87
50 21 88 89 75 21 90 91 54 21 92 93 80 57 94 95 75 59 96 97 66 31
98 99 90 21 100 101 85 61 102 103 90 50 104 105 93 84 106 107 70 38
108 109 52 21 found = efficacy found calc. = efficacy calculated
using the Colby formula
EXAMPLE 2
[0210] Venturia Test (Apple)/Protective
3 Solvent: 47 parts by weight of acetone Emulsifier: 3 parts by
weight of alkylaryl polyglycol ether
[0211] 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.
[0212] 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 konidia suspension of the causative
organism of apple scab Venturia inaequalis and then remain in an
incubation cabin at about 20.degree. C. and 100% relative
atmospheric humidity for one day.
[0213] The plants are then placed in a greenhouse at about
21.degree. C. and a relative atmospheric humidity of about 90%.
[0214] Evaluation is carried out 12 days after the inoculation. 0%
means an efficacy which corresponds to that of the control, whereas
an efficacy of 100% means that no infection is observed.
[0215] Active compounds, application rates and test results are
shown in the table below.
4TABLE 2 Venturia test (apple)/protective Active compound
application rate Active compound in g/ha Efficacy in % Known: 110 1
1 111 1 0 According to the invention: found calc. *) 112 113 54 1
found = efficacy found calc. = efficacy calculated using the Colby
formula
EXAMPLE 3
Erysiphe Test (Barley)/Curative
[0216]
5 Solvent: 10 parts by weight of N-methyl-pyrrolidone Emulsifier:
0.6 parts by weight of alkylaryl polyglycol ether
[0217] 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.
[0218] To test for curative activity, young plants are dusted with
spores of Erysiphe graminis f.sp. hordei. 48 hours after the
inoculation, the plants are sprayed with the active compound
preparation at the stated application rate.
[0219] The plants are placed in a greenhouse at a temperature of
about 20.degree. C. and a relative atmospheric humidity of about
80% to promote the development of mildew pustules.
[0220] Evaluation is carried out 7 days after the inoculation. 0%
means an efficacy which corresponds to that of the control, whereas
an efficacy of 100% means that no infection is observed.
[0221] Active compounds, application rates and test results are
shown in the table below.
6TABLE 3 Erysiphe test (barley)/curative Active compound
application rate Active compound in g/ha Efficacy in % Known: 114
25 81 115 25 75 According to the invention: 116 117 100
EXAMPLE 4
Erysiphe Test (Barley)/Protective
[0222]
7 Solvent: 10 parts by weight of N-methyl-pyrrolidone Emulsifier:
0.6 parts by weight of alkylaryl polyglycol ether
[0223] 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.
[0224] To test for protective activity, young plants are sprayed
with the active compound preparation at the stated application
rate.
[0225] After the spray coating has dried on, the plants are dusted
with spores of Erysiphe graminis f.sp. hordei.
[0226] The plants are placed in a greenhouse at a temperature of
about 20.degree. C. and a relative atmospheric humidity of about
80% to promote the development of mildew pustules.
[0227] Evaluation is carried out 7 days after the inoculation. 0%
means an efficacy which corresponds to that of the control, whereas
an efficacy of 100% means that no infection is observed.
[0228] Active compounds, application rates and test results are
shown in the table below
8TABLE 4 Erysiphe test (barley)/protective Active compound
application rate Active compound in g/ha Efficacy in % Known: 118
25 83 119 25 92 According to the invention: 120 121 100 122 123 100
124 125 100
EXAMPLE 5
[0229]
9 Solvent: 10 parts by weight of N-methyl-pyrrolidone Emulsifier:
0.6 parts by weight of alkylaryl polyglycol ether
[0230] 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.
[0231] To test for curative activity, young plants are dusted with
spores of Erysiphe graminis f.sp. tritici. 48 hours after the
inoculation, the plants are sprayed with the active compound
preparation at the stated application rate.
[0232] The plants are then placed in a greenhouse at a temperature
of about 20.degree. C. and a relative atmospheric humidity of about
80% to promote the development of mildew pustules.
[0233] Evaluation is carried out 7 days after the inoculation. 0%
means an efficacy which corresponds to that of the control, whereas
an efficacy of 100% means that no infection is observed.
[0234] Active compounds, application rates and test results are
shown in the table below.
10TABLE 5 Erysiphe test (wheat)/curative Active compound
application rate Active compound in g/ha Efficacy in % Known: 126
25 12.5 6.25 75 50 25 127 25 88 128 25 81 129 12.5 0 130 12.5 0 131
12.5 0 132 6.25 38 133 6.25 94 According to the invention: 134 100
135 136 137 100 138 139 100 140 141 100 142 143 100 144 145 63 146
147 75 148 149 100 150 151 100 152 153 100 154 155 75 156 157 50
158 159 100 160 161 100
EXAMPLE 6
[0235] Erysiphe Test (Wheat)/Protective
11 Solvent: 10 parts by weight of N-methyl-pyrrolidone Emulsifier:
0.6 parts by weight of alkylaryl polyglycol ether
[0236] 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.
[0237] To test for protective activity, young plants are sprayed
with the active compound preparation at the stated application
rate.
[0238] After the spray coating has dried on, the plants are dusted
with spores of Erysiphe graminis f.sp. tritici.
[0239] The plants are then placed in a greenhouse at a temperature
of about 20.degree. C. and a relative atmospheric humidity of about
80% to promote the development of mildew pustules.
[0240] Evaluation is carried out 7 days after the inoculation. 0%
means an efficacy which corresponds to that of the control, whereas
an efficacy of 100% means that no infection is observed.
[0241] Active compounds, application rates and test results are
shown in the table below.
12TABLE 6 Erysiphe test (wheat)/protective Active compound Effi-
application cacy Active compound rate in g/ha in % Known: 162 6.25
57 163 6.25 57 According to the invention: 164 165 79 166 167 71
168 169 71
EXAMPLE 7
[0242] Leptosphaeria nodorum Test (Wheat)/Protective
13 Solvent: 10 parts by weight of N-methyl-pyrrolidone Emulsifier:
0.6 parts by weight of alkylaryl polyglycol ether
[0243] 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.
[0244] To test for protective activity, young plants are sprayed
with the active compound preparation at the stated application
rate.
[0245] After the spray coating has dried on, the plants are sprayed
with a spore suspension of Leptosphaeria nodorum. The plants remain
in an incubation cabin at 20.degree. C. and 100% relative
atmospheric humidity for 48 hours.
[0246] The plants are then placed in a greenhouse at a temperature
of about 15.degree. C. and a relative atmospheric humidity of about
80%.
[0247] Evaluation is carried out 10 days after the inoculation. 0%
means an efficacy which corresponds to that of the control, whereas
an efficacy of 100% means that no infection is observed.
[0248] Active compounds, application rates and test results are
shown in the table below.
14TABLE 7 Leptosphaeria nodorum test (wheat)/protective Active
compound application rate Active compound in g/ha Efficacy in %
Known: 170 25 62 171 25 87 According to the invention: 172 173
100
EXAMPLE 8
[0249] Puccinia Test (Wheat)/Protective
15 Solvent: 10 parts by weight of N-methyl-pyrrolidone Emulsifier:
0.6 parts by weight of alkylaryl polyglycol ether
[0250] 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.
[0251] To test for protective activity, young plants are inoculated
with a spore suspension of Puccinia recondita in a 0.1% strength
aqueous agar solution. After the spray coating had dried on, the
plants are sprayed with the active compound preparation at the
stated application rate.
[0252] The plants remain in an incubation cabin at 20.degree. C.
and 100% relative atmospheric humidity for 24 hours.
[0253] The plants are then placed in a greenhouse at a temperature
of about 20.degree. C. and a relative atmospheric humidity of about
80% to promote the development of rust pustules.
[0254] Evaluation is carried out 10 days after the inoculation 0%
means an efficacy which corresponds to that of the control, whereas
an efficacy of 100% means that no infection is observed.
[0255] Active compounds, application rates and test results are
shown in the table below.
16TABLE 8 Puccinia test (wheat)/protective Active compound
application rate Active compound in g/ha Efficacy in % Known: 174
25 38 175 25 94 According to the invention: 176 177 100 178 179
100
EXAMPLE 9
[0256] Fusarium culmorum Test (Wheat)/Seed Treatment
[0257] The active compounds are applied as a dry seed dressing.
This is prepared by extending the respective active compound or the
active compound combination with ground minerals to give a finely
pulverulent mixture which ensures uniform distribution on the seed
surface.
[0258] To dress the seed, the infected seed together with the seed
dressing is shaken for 3 minutes in a sealed glass flask.
[0259] 2.times.100 corns of wheat are sown at a depth of 1 cm in
standard soil and cultivated in a greenhouse at a temperature of
about 18.degree. C. and a relative atmospheric humidity of about
95% in seed trays which receive a light regimen of 15 hours per
day.
[0260] About 3 weeks after sowing, the plants are evaluated for
symptoms. 0% means an efficacy which corresponds to that of the
control, whereas an efficacy of 100% means that no infection is
observed.
[0261] Active compounds, application rates and test results are
shown in the table below.
17TABLE 9 Fusarium culmorum test (wheat)/seed treatment Active
compound application rate Active compound in g/ha Efficacy in %
Known: 180 75 32 181 75 27 According to the invention: 182 183
41
EXAMPLE 10
[0262] Fusarium nivale Test (Triticale)/Seed Treatment
[0263] The active compounds are applied as a dry seed dressing.
This is prepared by extending the respective active compound or the
active compound combination with ground minerals to give a finely
pulverulent mixture which ensures uniform distribution on the seed
surface.
[0264] To dress the seed, the infected seed together with the seed
dressing is shaken for 3 minutes in a sealed glass flask.
[0265] 2.times.100 corns of wheat are sown at a depth of 1 cm in
standard soil and cultivated in a greenhouse at a temperature of
about 10.degree. C. and a relative atmospheric humidity of about
95% in seed trays which receive a light regimen of 15 hours per
day.
[0266] About 3 weeks after sowing, the plants are evaluated for
symptoms. 0% means an efficacy which corresponds to that of the
control, whereas an efficacy of 100% means that no infection is
observed.
[0267] Active compounds, application rates and test results are
shown in the table below
18TABLE 10 Fusarium nivale test (triticale)/seed treatment Active
compound application rate Active compound in g/ha Efficacy in %
Known: 184 75 25 14 0 185 75 94 186 25 0 According to the
invention: 187 188 99 189 190 31
EXAMPLE 11
[0268] Rhizoctonia solani Test (Cotton)/Seed Treatment
[0269] The active compounds are applied as a dry seed dressing.
This is prepared by extending the respective active compound or the
active compound combination with ground minerals to give a finely
pulverulent mixture which ensures uniform distribution on the seed
surface.
[0270] To dress the seed, the infected seed together with the seed
dressing is shaken for 3 minutes in a sealed glass flask.
[0271] 2.times.50 corns of seed are sown at a depth of 2 cm in
standard soil infected with Rhizoctonia solani, and the seeds are
cultivated in a greenhouse at a temperature of about 22.degree. C.
in seed trays which receive a light regimen of 15 hours per
day.
[0272] Evaluation is carried out after 8 days. 0% means an efficacy
which corresponds to that of the control, whereas an efficacy of
100% means that no infection is observed.
[0273] Active compounds, application rates and test results are
shown in the table below
19TABLE 11 Rhizoctonia solani test (cotton)/seed treatment Active
compound application rate Active compound in g/ha Efficacy in %
Known: 191 (I) 25 19 192 (III) 25 27 193 (IIc) 25 0 According to
the invention 194 195 40 196 197 31
* * * * *