U.S. patent application number 10/078241 was filed with the patent office on 2003-02-06 for synergistic fungicidal composition comprising a compound analogous to strobilurin.
Invention is credited to Duvert, Patrice.
Application Number | 20030027720 10/078241 |
Document ID | / |
Family ID | 9483441 |
Filed Date | 2003-02-06 |
United States Patent
Application |
20030027720 |
Kind Code |
A1 |
Duvert, Patrice |
February 6, 2003 |
Synergistic fungicidal composition comprising a compound analogous
to strobilurin
Abstract
A synergistic fungicidal composition comprising a compound A
having the formula 1 and a compound B which is a dicarboximide
derivative such as iprodione, procymidone or vinchlozolin, and a
method for controlling or preventing the development of
phytopathogenic fungi employing said composition.
Inventors: |
Duvert, Patrice; (Lyon,
FR) |
Correspondence
Address: |
Mary Katherine Baumeister
BURNS, DOANE, SWECKER & MATHIS, L.L.P.
P.O. Box 1404
Alexandria
VA
22313-1404
US
|
Family ID: |
9483441 |
Appl. No.: |
10/078241 |
Filed: |
February 20, 2002 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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10078241 |
Feb 20, 2002 |
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09505874 |
Feb 17, 2000 |
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09505874 |
Feb 17, 2000 |
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09051199 |
Jul 2, 1998 |
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6057331 |
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09051199 |
Jul 2, 1998 |
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PCT/FR96/01532 |
Oct 2, 1996 |
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Current U.S.
Class: |
504/118 |
Current CPC
Class: |
A01N 37/50 20130101;
A01N 43/54 20130101; A01N 43/54 20130101; A01N 53/00 20130101; A01N
47/38 20130101; A01N 43/76 20130101; A01N 37/50 20130101; A01N
53/00 20130101; A01N 47/38 20130101; A01N 43/76 20130101; A01N
37/50 20130101; A01N 2300/00 20130101; A01N 43/54 20130101; A01N
2300/00 20130101 |
Class at
Publication: |
504/118 |
International
Class: |
A01N 063/00 |
Foreign Application Data
Date |
Code |
Application Number |
Oct 5, 1995 |
FR |
95/11951 |
Claims
What is claimed is:
1. A fungicidal composition comprising a synergistic fungicidally
effective amount of a compound A which is (i) methyl
(E)-methoxyimino[.alpha.-(o-tolyloxy)-o-tolyl]acetate or (ii)
N-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamide,
and a compound B which is iprodione, the A/B ratio by weight being
between 0.02 and 5.
2. A fungicidal composition according to claim 1, wherein compound
A is methyl
(E)-methoxyimino[.alpha.-(o-tolyloxy)-o-tolyl]acetate.
3. A fungicidal composition according to claim 1, wherein compound
A is
N-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamide.
4. A fungicidal composition according to claim 1, wherein the A/B
ratio by weight is between 0.0625 and 1.33.
5. A fungicidal composition according to claim 1, wherein the A/B
ratio by weight is between 0.05 and 5.
6. A fungicidal composition according to claim 1, wherein the A/B
ratio by weight is between 0.17 and 1.33.
7. A fungicidal composition according to claim 1, wherein the A/B
ratio by weight is between 0.02 and 2.
8. A fungicidal composition according to claim 1, wherein the A/B
ratio by weight is between 0.0625 and 0.25.
9. A fungicidal composition according to claim 1, further
comprising at least one member selected from the group consisting
of an agriculturally acceptable solid or liquid vehicle and an
agriculturally acceptable surface-active agent.
10. A fungicidal composition according to claim 9, comprising from
0.05% to 95% by weight of compounds A and B.
11. A process for the curative or preventative control of
phytopathogenic fungi in plants, said process comprising applying
to plants or to the locus in which they grow a synergistic
fungicidally effective non-phytotoxic amount of a compound A which
is (i) methyl (E)-methoxyimino[.alpha.-(o-tolyloxy)-o-tolyl]acetate
or (ii)
N-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamide,
and a compound B which is iprodione, the A/B ratio by weight being
between 0.02 and 5.
12. A process according to claim 11, wherein compound A is methyl
(E)-methoxyimino[.alpha.-(o-tolyloxy)-o-tolyl]acetate.
13. A process according to claim 11, wherein compound A is
N-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamide.
14. A process according to claim 11, wherein the A/B ratio by
weight is between 0.0625 and 1.33.
15. A process according to claim 11, wherein the synergistic
fungicidally effective non-phytotoxic amount of A and B is applied
to crops or lawns to control fungi which are phytopathogenic
towards crops or lawns, respectively.
16. A process according to claim 15, wherein compound A is
methyl-(E)-methoxyimino[.alpha.-(o-tolyloxy)-o-tolyl]acetate.
17. A process according to claim 15, wherein compound A is
N-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamide.
18. A process according to claim 15, wherein the synergistic
fungicidally effective non-phytotoxic amount of A and B is applied
to the aerial parts of the plants.
19. A process according to claim 15, wherein the synergistic
fungicidally effective non-phytotoxic amount of A and B is applied
to crops and wherein the A/B ratio by weight is between 0.05 and
5.
20. A process according to claim 15, wherein the synergistic
fungicidally effective non-phytotoxic amount of A and B is applied
to crops and wherein the A/B ratio by weight is between 0.17 and
1.33.
21. A process according to claim 15, wherein the synergistic
fungicidally effective non-phytotoxic amount of A and B is applied
to crops at a dose rate of between 150 and 1500 g/ha.
22. A process according to claim 15, wherein the synergistic
fungicidally effective non-phytotoxic amount of A and B is applied
to crops at a dose rate of between 400 and 1000 g/ha.
23. A process according to claim 15, wherein the synergistic
fungicidally effective non-phytotoxic amount of A and B is applied
to lawns and wherein the A/B ratio by weight is between 0.02 and
2.
24. A process according to claim 15, wherein the synergistic
fungicidally effective non-phytotoxic amount of A and B is applied
to lawns and wherein the A/B ratio by weight is between 0.0625 and
0.25.
25. A process according to claim 15, wherein the synergistic
fungicidally effective non-phytotoxic amount of A and B is applied
to lawns at a dose rate of between 1100 and 7000 g/ha.
26. A process according to claim 15, wherein the synergistic
fungicidally effective non-phytotoxic amount of A and B is applied
to lawns at a dose rate of between 2250 and 5000 g/ha.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] This application is a continuation of application Ser. No.
09/505,874, filed Feb. 17, 2000, incorporated by reference herein
in its entirety and relied upon, which is a divisional of
application Ser. No. 09/051,199, filed Jul. 2, 1998, now U.S. Pat.
No. 6,057,331, which is the U.S. national phase of PCT/FR96/01532,
filed Oct. 2, 1996, and designating the United States, and
published by the International Bureau in French, not English, on
Apr. 10, 1997 as WO97/12520.
BACKGROUND OF THE INVENTION
[0002] 1. Field of the Invention
[0003] The subject of the present invention is a synergistic
fungicidal composition comprising a compound analogous to
strobilurin and a process which makes use of the said composition
and which is intended for the curative or preventive protection of
crops against fungal attacks.
[0004] 2. Background of the Prior Art
[0005] Compounds analogous to strobilurin with a fungicidal effect
are known, in particular from European Patent Publication EP 253213
or 398692 or from International Publication WO 9208703, which make
it possible to prevent the growth and the development of
phytopathogenic fungi capable of attacking crops.
[0006] However, it is always desirable to improve the spectrum of
activity and the effectiveness of such compounds with a fungicidal
effect or to reinforce them by combining them with other molecules
in order to obtain a more effective product or alternatively to
prevent the appearance of fungal strains which are resistant to
these new fungicides.
[0007] It is also highly desirable to have available fungicidal
products which enjoy an improved persistence of effect, likely to
space out in time the number of plant-protection treatments
necessary for satisfactory control of the parasites.
[0008] It is, in any event, particularly advantageous to be able to
decrease the amount of chemicals distributed in the environment,
while ensuring high-performance protection of crops against fungal
attacks.
[0009] It has now been found that one (or a number) of the above
objectives could be achieved by virtue of the fungicidal
composition according to the present invention.
SUMMARY OF THE INVENTION
[0010] The subject of the present invention is therefore a
synergistic fungicidal composition comprising at least one compound
A of formula (I): 2
[0011] in which:
[0012] A is the nitrogen atom or the --CH group,
[0013] B is the --OCH.sub.2--, --CH.sub.2O--,
--C(CH.sub.3)--O--N.dbd.CH-- or --CH.dbd.N--O--CH(CH.sub.3)-- group
or the group of formula (II) 3
[0014] R.sub.1 is an alkyl group containing 1 to 4 carbon atoms,
preferably the methyl group,
[0015] R.sub.2 is --OCH.sub.3 or --NHCH.sub.3,
[0016] X is a halogen atom, the cyano group or an alkyl or
haloalkyl group containing 1 to 4 carbon atoms, preferably the
methyl or trifluoromethyl group,
[0017] n is equal to 1 or 2, with, when n is equal to 2, the
possibility of having different X groups,
[0018] and at least one fungicidal compound B chosen from the group
comprising dicarboximide derivatives, such as iprodione,
procymidone and vinchlozolin,
[0019] the said composition comprising the components A and B in an
A/B ratio by weight of between 0.02 and 5, preferably between
0.0625 and 1.33,
[0020] with the proviso that when compound B is procymidone, then B
in formula I is the group of formula
BRIEF DESCRIPTION OF THE DRAWING
[0021] The sole FIGURE of Drawing, FIG. 1, is an isobole plot for
ICIA 5504, i.e. methyl
(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-
-methoxyacrylate, and iprodione in radish seedlings against
Alternaria brassicae (alternaria disease).
DETAILED DESCRIPTION OF THE INVENTION, PREFERRED EMBODIMENTS AND
BEST MODE
[0022] It is clearly understood that the said fungicidal
composition can contain a single compound B or more than one such
compound, for example 1, 2 or 3 compounds B, according to the use
for which the combination is intended. Likewise, the composition
may comprise more than one compound A.
[0023] Preference is given to the fungicidal composition according
to the invention in which the compound A is methyl
(E)-2-{2-[6-(2-cyanophenoxy)p-
yrimidin-4-yloxy]phenyl}-3-methoxyacrylate, methyl
(E)-methoxyimino[.alpha- .-(o-tolyloxy)-o-tolyl]acetate or
N-methyl-(E)-methoxyimino[2-(2,5-dimethy-
lphenoxymethyl)phenyl]acetamide.
[0024] Preference is further given, among the more especially
preferred meanings of the compound B defined above, to iprodione.
In an entirely unexpected way, the composition according to the
invention significantly improves the effect of the active materials
taken separately with respect to a certain number of fungi which
are particularly harmful to crops, for example in particular grapes
or the Solanaceae. This improvement is reflected in particular by a
decrease in the doses of each of the constituents, which is
particularly advantageous for the user and the environment. The
fungicidal product thus exhibits synergistic properties attested by
application of the Tammes method, "Isoboles, a graphic
representation of synergism in pesticides", Netherlands Journal of
Plant Pathology, 70(1964), p. 73-80 or as defined by Limpel, L. E.,
P. H. Schuldt and D. Lammont, 1962, Proc. NEWCC 16:48-53, using the
following formula, also called Colby's formula:
E=X+Y-X.Y/100
[0025] in which:
[0026] E is the expected percentage inhibition of the growth of the
fungus by a mixture of the two fungicides A and B at defined doses,
equal to a and b respectively;
[0027] X is the observed percentage inhibition by the fungicide A
at dose a,
[0028] Y is the observed percentage inhibition by the fungicide B
at dose b.
[0029] When the percentage inhibition observed for the mixture is
greater than E, there is synergism.
[0030] Preferably, when the component B is iprodione, the A/B ratio
is between 0.05 and 5, preferably between 0.17 and 1.33, for all
the crops envisaged.
[0031] In the particular case of lawns, the A/B ratio will
generally be between 0.02 and 2, preferably between 0.0625 and
0.25.
[0032] The structures corresponding to the common names of the
fungicidal active materials which appear in the definition of B are
shown in at least one of the following 2 works:
[0033] "The Pesticide Manual", edited by Clive Tomlin and published
by The British Crop Protection Council, 10th edition;
[0034] l'Index phytosanitaire [Plant-protection index] 1994,
published by l'Association de Coordination Technique Agricole
[Agricultural Technical Coordination Association], 30th
edition.
[0035] As regards the derivatives analogous to strobilurin, methyl
(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate
(or ICIA5504) is described in International Publication WO 9208703;
methyl (E)-methoxyimino[.alpha.-(o-tolyloxy)-o-tolyl]acetate (or
BAS490F) is described in European Patent Publication EP 253213; and
N-methyl-(E)-methoxyimino[2-(2,5-dimethylphenoxymethyl)phenyl]acetamide
(or SSF-129) is described in European Patent Publication EP 398692.
Moreover, ICIA5504 and BAS490F are listed in the abovementioned
work "The Pesticide Manual".
[0036] The fungicidal composition according to the invention
comprises, as active material, at least one compound A and at least
one compound B as a mixture with solid or liquid vehicles which are
acceptable in agriculture and/or surface-active agents which are
also acceptable in agriculture. In particular, the inert and
conventional vehicles and the conventional surface-active agents
can be used. These compositions cover not only compositions which
are ready to be applied to the crop to be treated by means of a
suitable device, such as a spray device, but also commercial
concentrated compositions which have to be diluted before
application to the crop. The combination of at least one compound A
with at least one compound B is denoted as active material.
[0037] These compositions can also contain any kind of other
ingredients such as, for example, protective colloids, adhesives,
thickening agents, thixotropic agents, penetrating agents,
stabilizing agents, sequestering agents and the like. More
generally, the compounds A and B can be combined with all the solid
or liquid additives corresponding to the conventional formulating
techniques.
[0038] Generally, the compositions according to the invention
usually contain from 0.05 to 95% (by weight) of active material,
one or more solid or liquid vehicles and, optionally, one or more
surface-active agents.
[0039] In the present account, the term "vehicle" denotes a natural
or synthetic, organic or inorganic material with which the active
material is combined to facilitate its application on the aerial
parts of the plant. This vehicle is thus generally inert and it
must be acceptable in agriculture, especially on the treated plant.
The vehicle can be solid (clays, natural or synthetic silicates,
silica, resins, waxes, solid fertilizers and the like) or liquid
(water, alcohols, especially butanol, and the like).
[0040] The surface-active agent can be an emulsifying, dispersing
or wetting agent of ionic or nonionic type or a mixture of such
surface-active agents. There may be mentioned, for example, salts
of polyacrylic acids, salts of lignosulphonic acids, salts of
phenolsulphonic or naphthalenesulphonic acids, polycondensates of
ethylene oxide with fatty alcohols or with fatty acids or with
fatty amines, substituted phenols, (especially alkylphenols or
arylphenols), salts of esters of sulphosuccinic acids, taurine
derivatives (especially alkyltaurates), phosphoric esters of
polyoxyethylenated phenols or alcohols, esters of fatty acids and
of polyols, and the derivatives of the above compounds containing
sulphate, sulphonate and phosphate functional groups. The presence
of at least one surface-active agent is generally indispensable
when the active material and/or the inert vehicle is/are not
soluble in water and the carrier agent for application is
water.
[0041] The compositions for agricultural use according to the
invention can thus contain the active material within very wide
limits, ranging from 0.05% to 95% (by weight). Their surface-active
agent content is advantageously of between 5% and 40% by weight.
Unless otherwise stated, the percentages given in this description,
including the claims, are by weight.
[0042] These compositions according to the invention are themselves
in fairly diverse, solid or liquid forms.
[0043] There may be mentioned, as forms of solid compositions, the
powders for dusting (with an active material content which can
range up to 100%) and the granules, especially those obtained by
extrusion, by compacting, by impregnation of a granulated support,
or by granulation from a powder (the active material content in
these granules being between 0.5 and 80% for the latter cases), the
tablets or effervescent tablets.
[0044] The fungicidal composition according to the invention can
also be used in the form of powders for dusting; it is also
possible to use a composition comprising 50 g of active material
and 950 g of talc; it is also possible to use a composition
comprising 20 g of active material, 10 g of finely divided silica
and 970 g of talc; these constituents are mixed and milled and the
mixture is applied by dusting.
[0045] There may be mentioned, as forms of liquid compositions or
those intended to constitute liquid compositions at the time of
application, solutions, in particular water-soluble concentrates,
emulsifiable concentrates, emulsions, suspension concentrates,
aerosols, wettable powders (or powder to be sprayed), pastes or
gels.
[0046] The emulsifiable or soluble concentrates most often comprise
10 to 80% of active material, the emulsions or solutions ready for
application containing, for their part, 0.001 to 20% of active
material.
[0047] In addition to the solvent, the emulsifiable concentrate may
contain, when necessary, 2 to 20% of appropriate additives such as
stabilizing agents, surface-active agents, penetrating agents,
corrosion inhibitors, colorants or adhesives mentioned above.
[0048] Starting from these concentrates, it is possible to obtain,
by diluting with water, emulsions of any desired concentration
which are particularly suitable for applying to crops.
[0049] By way of example, here is the composition of a few
emulsifiable concentrates:
EC Example 1:
[0050]
1 active material 400 g/l alkali metal dodecylbenzene 24 g/l
sulphonate oxyethylated nonylphenol 16 g/l with 10 molecules of
ethylene oxide cyclohexanone 200 g/l aromatic solvent qs 1
litre
[0051] According to another emulsifiable concentrate formula, the
following are used:
EC Example 2:
[0052]
2 active material 250 g expoxidized vegetable oil 25 g mixture of
alkylaryl sulphonate 100 g and of ether of polyglycol and fatty
alcohols dimethylformamide 50 g xylene 575 g
[0053] The suspension concentrates, which can also be applied by
spraying, are prepared so as to obtain a stable fluid product which
does not settle out and they generally contain from 10 to 75% of
active material, from 0.5 to 15% of surface-active agents, from 0.1
to 10% of thixotropic agents and from 0 to 10% of suitable
additives, such as antifoaming agents, corrosion inhibitors,
stabilizing agents, penetrating agents and adhesives and, as
vehicle, water or an organic liquid in which the active material is
insoluble or nearly insoluble: certain organic solid materials or
inorganic salts can be dissolved in the vehicle to aid in
preventing sedimentation or as antigels for water.
[0054] A suspension concentrate composition is given here as an
example:
SC EXAMPLE 1
[0055]
3 active material 500 g polyethoxylated tristyrylphenyl 50 g
phosphate polyethoxylated alkylphenol 50 g sodium polycarboxylate
20 g ethylene glycol 50 g organopolysiloxane oil (antifoaming 1 g
agent) polysaccharide 1.5 g water 316.5 g
[0056] Wettable powders (or powder to be sprayed) are generally
prepared so that they contain 20 to 95% of active material, and
they generally contain, in addition to the solid vehicle, from 0 to
30% of a wetting agent, from 3 to 20% of a dispersing agent and,
when this is necessary, from 0.1 to 10% of one or more stabilizing
agents and/or other additives, such as penetrating agents,
adhesives, or anticlumping agents, dyes, and the like.
[0057] To obtain powders to be sprayed or wettable powders, the
active materials are intimately mixed, in suitable mixers, with the
additional substances and the mixture is milled with mills or other
suitable grinders. Powders to be sprayed are thereby obtained with
advantageous wettability and suspensibility; they can be suspended
in water at any desired concentration and these suspensions can be
used very advantageously in particular for application to plant
leaves.
[0058] Pastes can be produced in place of wettable powders. The
conditions and modes of production and use of these pastes are
similar to those of wettable powders or powders to be sprayed.
[0059] Various wettable powder (or powder to be sprayed)
compositions are given here as examples:
WP EXAMPLE 1
[0060]
4 active material 50% ethoxylated fatty alcohol (wetting 2.5%
agent) ethoxylated phenylethylphenol 5% (dispersing agent) chalk
(inert vehicle) 42.5%
WP EXAMPLE 2
[0061]
5 active material 10% C13 branched-type synthetic oxo alcohol,
0.75% ethoxylated with 8 to 10 molecules of ethylene oxide (wetting
agent) neutral calcium lignosulphonate 12% dispersing agent)
calcium carbonate (inert filler) qs for 100%
[0062] This wettable powder contains the same ingredients as in the
above example, in the proportions below:
WP EXAMPLE 3
[0063]
6 active material 75% wetting agent 1.50% dispersing agent 8%
calcium carbonate (inert filler) qs for 100%
WP EXAMPLE 4
[0064]
7 active material 90% ethoxylated fatty alcohol (wetting agent) 4%
ethoxylated phenylethylphenol (dispersing agent) 6%
WP EXAMPLE 5
[0065]
8 active material 50% mixture of anionic and nonionic surface- 2.5%
active agents (wetting agent) sodium lignosulphonate (dispersing
agent) 5% kaolin clay (inert vehicle) 42.5%
[0066] Aqueous dispersions and emulsions, for example the
compositions obtained by diluting a wettable powder or an
emulsifiable concentrate according to the invention with water, are
contained within the general scope of the present invention.
Emulsions can be of the water-in-oil or oil-in-water type and they
can have a thick consistency, like that of a "mayonnaise".
[0067] The fungicidal compositions according to the invention can
be formulated in the form of water-dispersible granules, which also
come within the scope of the invention.
[0068] These dispersible granules, with a bulk density generally of
between approximately 0.3 and 0.6, have a particle size generally
of between approximately 150 and 2000 and preferably between 300
and 1500 microns.
[0069] The active material content of these granules is generally
between approximately 1% and 90%, and preferably between 25% and
90%.
[0070] The rest of the granule comprises a solid filler and,
optionally, surface-active adjuvants which confer
water-dispersibility properties on the granule. These granules can
be essentially of two distinct types according to whether the
filler chosen is soluble or insoluble in water. When the filler is
water-soluble, it can be inorganic or, preferably, organic.
Excellent results were obtained with urea. In the case of an
insoluble filler, the latter is preferably inorganic, such as, for
example, kaolin or bentonite. It is then advantageously accompanied
by surface-active agents (in a proportion of 2 to 20% by weight of
the granule) of which more than half comprises, for example, at
least one dispersing agent, essentially anionic, such as an alkali
metal or alkaline-earth metal polynaphthalenesulphonate or an
alkali metal or alkaline-earth metal lignosulphonate, the remainder
consisting of nonionic or anionic wetting agents such as an alkali
metal or alkaline-earth metal alkylnaphthalenesulphonate.
[0071] Moreover, although this is not indispensable, it is possible
to add other adjuvants such as antifoaming agents.
[0072] The granule according to the invention can be prepared by
mixing the necessary ingredients and then granulating according to
several techniques known per se (granulator, fluid bed, sprayer,
extrusion, and the like). The preparation generally finishes with a
crushing followed by a sieving to the particle size chosen within
the limits mentioned above. Granules obtained as above and then
impregnated with a composition containing the active material can
alternatively be used.
[0073] It is preferably obtained by extrusion, by carrying out the
preparation as indicated in the examples below.
DG EXAMPLE 1
Dispersible Granules
[0074] 90% by weight of active material and 10% of urea in the form
of pearls are mixed in a mixer. The mixture is then milled in a pin
mill. A powder is obtained which is moistened with approximately 8%
by weight of water. The moist powder is extruded in a
perforated-roller extruder. A granular material is obtained which
is dried, and then crushed and sieved, so as to respectively keep
only the granules with a size of between 150 and 2000 microns.
DG EXAMPLE 2
Dispersible Granules
[0075] The following constituents are mixed in a mixer:
9 active material 75% wetting agent (sodium alkylnaphthalene- 2%
sulphonate dispersing agent (sodium 8% polynaphthalenesulphonate)
water-insoluble inert filler (kaolin) 15%
[0076] This mixture is granulated on a fluid bed in the presence of
water and then dried, crushed and sieved so as to obtain granules
with a size of between 0.15 and 0.80 mm.
[0077] These granules can be used alone or in solution or
dispersion in water so as to obtain the required dose.
[0078] As regards the compositions which are suitable for storage
and transportation, they more advantageously contain from 0.5 to
95% (by weight) of active material.
[0079] The invention also relates to a product comprising at least
one compound A and at least one compound B as defined above for
controlling phytopathogenic fungi by simultaneous, sequential or
separate application.
[0080] Another subject of the invention is a process for
controlling phytopathogenic fungi in a medium, characterized in
that at least one compound A and at least one compound B, these
compounds being as defined above, and the combination of these
compounds being in an effective and non-phytotoxic total quantity,
are applied to said medium.
[0081] More precisely, the subject of the invention is a process
for the curative or preventive control of fungi which are
phytopathogenic, for example, towards crops or lawns, characterized
in that an effective and non-phytotoxic amount of a combination of
at least one compound A and at least one compound B, for example in
a fungicidal composition according to the invention, is generally
applied on the aerial parts of plants.
[0082] The fungi which are phytopathogenic towards crops which can
be combated by this process are in particular those:
[0083] from the Oomycetes group:
[0084] from the Phytophthora genus, such as Phytophthora infestans
(downy mildew of the Solanaceae, in particular of potatoes or
tomatoes), Phytophthora citrophthora, Phytophthora capsici,
Phytophthora cactorum, Phytophthora palmivora, Phytophthora
cinnamoni, Phytophthora megasperma or Phytophthora parasitica,
[0085] from the Peronosporaceae family, in particular Plasmopara
viticola (grape downy mildew), Plasmopara halstedei (sunflower
downy mildew), Pseudoperonospora sp (in particular downy mildew of
cucurbits and of hops), Bremia lactucae (lettuce downy mildew) or
Peronospora tabacinae (tobacco downy mildew),
[0086] from the Adelomycetes group:
[0087] from the Alternaria genus, for example Alternaria solani
(alternaria disease of the Solanaceae and in particular of tomatoes
and potatoes),
[0088] from the Guignardia genus, in particular Guignardia
bidwellii (black rot of grapes),
[0089] from the Oidiums group, for example grape powdery mildew
(Uncinula necator); powdery mildew of legumes, for example Erysiphe
polygoni (powdery mildew of crucifers); Leveillula taurica,
Erysiphe cichoracearum, Sphaerotheca fuligena; (powdery mildew of
cucurbits, of composites or of tomatoes); Erysiphe communis (beet
and cabbage powdery mildew); Erysiphe pisi (pea or lucerne powdery
mildew); Erysiphe polyphaga (bean and cucumber powdery mildew);
Erysiphe umbelliferarum (powdery mildew of the Umbelliferae, in
particular of carrots); Sphaerotheca humuli (hop powdery mildew);
or Erysiphe graminis (powdery mildew of cereals),
[0090] from the Septoria genus, for example Septoria nodorum or
Septoria tritici (septoria disease of cereals);
[0091] from the Sclerotinia genus, for example Sclerotinia
sclerotinium or Sclerotinia homeocarpa (lawn sclerotinia
disease),
[0092] from the Basidiomycetes group:
[0093] from the Puccinia genus, for example Puccinia recondita or
striiformis (wheat rusts),
[0094] of the Rhizoctonia spp. family.
[0095] A classification made no longer by targeted fungi but by
target crops can be illustrated as below:
[0096] barley-helminthosporium (Helminthosporium),
[0097] rape: alternaria (Alternaria spp.), rot (Botrytis cinerea),
sclerotinia disease (Sclerotinia sclerotinium),
[0098] grapes: powdery mildew (Uncinula necator), downy mildew
(Plasmopara viticola), rot (Botrytis cinerea), excoriosis
(Phomopsis viticola) and black rot (Guignardia bidweliii),
[0099] Solanaceae: downy mildew (Phytophthora infestans),
alternaria disease (Alternaria solani) and rot (Botrytis
cinerea),
[0100] legumes: downy mildews (Peronospora spp., Bremia lactucae,
Pseudoperonospora spp.), or alternaria disease (Alternaria spp.),
sclerotinia disease (Sclerotinia spp.), rot (Botrytis cinerea) or
powdery mildew (Erysiphe spp. or Sphaerotheca fuliginea), foot or
root rot (Rhizoctonia spp.),
[0101] rice: foot or root rot (Rhizoctonia spp.),
[0102] arboriculture: scab (Venturia inaequalis), powdery mildew
(Podosphaera leucotricha), alternaria disease (Alternaria spp.),
rot (Botrytis cinerea) and monilia disease (Monilia
fructigena),
[0103] citrus fruits: scab (Elsinoe fawcetti), melanose (Phomopsis
citri) and diseases due to Phytophthora spp., bananas: cercospora
disease (Mycosphaerella figiensis),
[0104] lawns: rust, powdery mildew, helminthosporium disease or
soil diseases (Microdochium nivale, Pythium spp., Rhizoctonia
solani, Sclerotinia homeocarpa and the like).
[0105] The fungicidal composition which is the subject of the
invention is applied by means of various treatment processes, such
as:
[0106] spraying a liquid comprising the said composition on the
aerial parts of the crops to be treated,
[0107] dusting, the incorporation of granules or of powders into
the soil, sprinkling, injecting into trees or painting.
[0108] The spraying of a liquid on the aerial parts of the crops to
be treated is the preferred treatment process.
[0109] "Effective and non-phytotoxic amount" is understood to mean
an amount of composition according to the invention which is
sufficient to make possible control or destruction of the fungi
present or capable of appearing on the crops and which does not
result in any notable phytotoxicity symptoms with respect to the
said crops. Such an amount is capable of varying within wide limits
depending on the fungi to be combated, the type of crop, the
weather conditions and the compounds included in the fungicidal
composition according to the invention. This amount can be
determined by systematic tests in the field, within the scope of
the person skilled in the art.
[0110] The use doses during the implementation of the process
according to the invention will then generally be:
[0111] on barley, rape, rice, grapes, legumes, Solanaceae, bananas,
arboriculture or citrus fruits:
[0112] 100 to 1000 g of compound B, e.g. iprodione +50 to 500 g/ha
of compound A and more precisely 300 to 600 g+100 to 400 g/ha, i.e.
a total dose of compounds A and B of between 150 and 1500 g/ha,
preferably between 400 and 1000 g/ha,
[0113] on lawns:
[0114] 1000 to 5000 g of compound B, e.g. iprodione +100 to 2000
g/ha of compound A and more precisely 2000 to 4000 g+250 to 1000
g/ha, i.e. a total dose of compounds A and B of between 1100 and
7000 g/ha, preferably between 2250 and 5000 g/ha.
[0115] The following examples are given purely by way of
illustration of the invention, which they do not limit in any
way.
[0116] In the FIGURE appended to the present text, the dose of each
active material, taken in isolation, required for control of the
phytopathogenic fungus at the level indicated is compared with that
of the 2 active materials taken as a mixture. The effective dose of
each active material taken in isolation is shown on the axis of the
abscissae and of the ordinates and a straight line is traced
cutting these 2 axes and connecting these 2 doses. When an active
material taken in isolation is not effective, the straight line is
parallel to the axis of the coordinates which shows the doses of
this active material. As regards the 2 active materials taken as a
mixture, the dose of the mixture at a given ratio is shown by a
point.
EXAMPLE 1
[0117] In vivo test of the combination of ICIA5504 with iprodione
with respect to alternaria disease of radish (Alternaria brassicae)
by preventive treatment 24 hours before infection.
[0118] A suspension comprising the compounds A and B in a liquid
mixture composed of a surface-active agent (oleate of
polyoxyethylenated derivative of sorbitan) and water is
prepared.
[0119] The component B is iprodione; the A/B ratio is 0.25, 0.5, 1,
2 or 4.
[0120] Radish seedlings (variety Pernot), are grown in small pots.
When these seedlings are 10-12 days old (cotyledon, 1st leaf
stage), they are treated by spraying with the above suspension.
[0121] Seedlings, used as controls, are treated with a similar
suspension but which does not contain active material ("formulation
blank").
[0122] After 24 hours, each seedling is infected by spraying with
an aqueous suspension of spores of Alternaria brassica, which
suspension is obtained from an in vitro culture of the fungus.
These spores are suspended at a concentration of 40,000 units per
cm.sup.3 of inoculum. Infection is carried out by spraying the
inoculum at the top surface of the leaves.
[0123] The infected seedlings are then incubated for six days at
18-20.degree. C. at 90-100% relative humidity under natural
light.
[0124] Reading is carried out 6 days after infection, in comparison
with the control seedlings.
[0125] The results obtained are reported in the form of points,
corresponding to 80% destruction of the parasite, and are plotted
on a Tammes isobole diagram which contains, on the abscissa, the
doses of A expressed in ppm (mg/l) and, on the ordinate, the doses
of B, also in ppm (mg/l).
[0126] The diagram of FIG. 1 is obtained. It appears that the
addition of iprodione makes it possible, in an entirely unexpected
way, to lower the dose of A necessary for the destruction of 80% of
the parasite below 115 ppm (mg/l), which corresponds to the dose of
A alone which it is necessary to apply to obtain the same
percentage of destruction.
[0127] The arrangement of the points obtained therefore shows a
bilateral effect described, according to the Tammes method
mentioned above, as a "two-sided effect". This arrangement
corresponds to a type-III isobole according to the said method
(page 74 of the corresponding bibliographical reference already
cited) and is characteristic of a synergy.
EXAMPLE 2
[0128] In vivo test of the combination of ICIA5504 with iprodione
with respect to helminthosporium disease of barley by preventive
treatment 7 days before infection.
[0129] The fungicides are used at the following doses:
[0130] iprodione (Rovral SC 500 g/l (B): 12.5-25-50-100-200-400-800
g/ha,
[0131] ICI A5504 (SC 250 g/l)(A): 1.5-3.1-6.2-12.5-25-50-100-200
g/ha,
[0132] iprodione (B)/ICIA5504(A) 4: 6.2+1.5 to 800+200 g/ha,
[0133] iprodione/ICIA5504=2: 3.1+1.5 to 400+200 g/ha
[0134] iprodione/ICIA5504=1: 1.5+1.5 to 200+200 g/ha
[0135] iprodione/ICIA5504=0.5: 0.75+1.5 to 100+200 g/ha
[0136] The young barley plants (var. Express) which are 12 days old
(first leaf developed stage) are treated with the experimental
fungicides at the doses indicated above in a slurry volume of 250
l/ha (3 repeats/dose). Seven days after the treatment, the young
barley plants are infected with a suspension of Pyrenophora teres
spores (10,000 spores/ml). The young plants are incubated for 48
hours at 20.degree. C., 100% relative humidity (RH). Next, the
plants are transferred to a greenhouse at 20.degree. C., 70-80% RH
under natural light. The grading of the disease is carried out ten
days after infection by estimating the leaf surface area
contaminated on the first leaf (10 young plants/pot).
[0137] By comparing with the control (non-treated-contaminated) a
percentage efficacy is calculated. The synergy is then quantified
by using the Colby model. The following results are thereby
obtained:
[0138] Observed Efficacy:
10 B/A 0 g/ha 1.5 3.1 6.2 12.5 25 50 100 200 0 g/ha 0 0 17.54 34.21
59.21 76.75 83.86 81.67 92.72 12.5 15.79 78.6 88.68 83.95 94.04 25
7.02 88.77 94.47 85.70 93.68 50 37.72 91.49 96.23 92.54 90.88 100
35.09 94.65 95.53 93.33 96.23 200 47.37 95.53 97.37 95 400 50.88
96.14 97.72 800 59.65 95.95
[0139] Theoretical Efficacy According to Colby:
11 B/A 0 g/ha 1.5 3.1 6.2 12.5 25 50 100 200 0 g/ha 0 0 17.54 34.21
59.21 76.75 83.86 81.67 92.72 12.5 15.79 30.56 44.60 65.65 80.42 25
7.02 38.83 62.07 78.38 84.99 50 37.72 74.60 85.52 89.95 88.58 100
35.09 84.91 89.52 88.10 95.27 200 47.37 91.51 90.35 96.17 400 50.88
91.00 96.42 800 59.65 97.06
[0140] Synergy (% Gain):
12 B/A 0 g/ha 1.5 3.1 6.2 12.5 25 50 100 200 0 g/ha 12.5 +48 +44
+18 +14 25 +50 +32 +7 +9 50 +17 +11 +3 +2 100 +10 +6 +5 +1 200 +4
+7 -1 400 +5 +1 800 -1
* * * * *