U.S. patent application number 15/537940 was filed with the patent office on 2018-01-04 for 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one as a seed treatment.
This patent application is currently assigned to Adama Makhteshim Ltd.. The applicant listed for this patent is Adama Makhteshim Ltd.. Invention is credited to Carla J.R. Klittich, W. John Owen, Chenglin Yao.
Application Number | 20180000082 15/537940 |
Document ID | / |
Family ID | 56151456 |
Filed Date | 2018-01-04 |
United States Patent
Application |
20180000082 |
Kind Code |
A1 |
Klittich; Carla J.R. ; et
al. |
January 4, 2018 |
5-FLUORO-4-IMINO-3-(ALKYL/SUBSTITUTED
ALKYL)-1-(ARYLSULFONYL)-3,4-DIHYDROPYRIMIDIN-2(1H)-ONE AS A SEED
TREATMENT
Abstract
The present disclosure relates to the use of a compound of
Formula I as a seed treatment to prevent or control plant diseases.
##STR00001##
Inventors: |
Klittich; Carla J.R.;
(Indianapolis, IN) ; Yao; Chenglin; (Indianapolis,
IN) ; Owen; W. John; (Carmel, IN) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Adama Makhteshim Ltd. |
Beer Sheva |
|
IL |
|
|
Assignee: |
Adama Makhteshim Ltd.
Beer Sheva
IL
|
Family ID: |
56151456 |
Appl. No.: |
15/537940 |
Filed: |
December 18, 2015 |
PCT Filed: |
December 18, 2015 |
PCT NO: |
PCT/US15/66756 |
371 Date: |
June 20, 2017 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
62096301 |
Dec 23, 2014 |
|
|
|
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
C07D 239/47 20130101;
A01N 43/54 20130101 |
International
Class: |
A01N 43/54 20060101
A01N043/54; C07D 239/47 20060101 C07D239/47 |
Claims
1. A method of treating a plant seed or seedling to produce a plant
resistant to fungal attack, wherein the plant seed or seedling is
treated with a compound of Formula I, wherein R.sub.1 is selected
from H, C.sub.1-C.sub.6 alkyl, and C.sub.1-C.sub.6 alkoxy, and
R.sub.2 is selected from C.sub.1-C.sub.6 alkyl, phenyl, benzyl, and
--CH.sub.3-- thiophenyl. ##STR00003##
2. The method of claim 1, wherein R.sub.1 and R.sub.2 are each
--CH.sub.3.
3. The method of claim 2, wherein the compound of Formula I is
applied at a rate from about 0.5 to about 500 grams per 100
kilograms of seed.
4. The method of claim 1, wherein the seed being treated is a wheat
seed (Triticum sp.; TRZSS), sugar beet (BEAVA), or peanut
(ARHHY).
5. The method of claim 1, wherein the fungal pathogen is selected
from the group consisting of the causal agent of wheat leaf blotch
(Zymoseptoria tritici), leaf spot of sugar beets (Cercospora
beticola), and leaf spot of peanut (Cercospora arachidicola and
Cercosporidium personatum).
6. A plant seed or seedling adapted to produce a plant resistant to
fungal attack, wherein the plant seed or seedling is treated with a
compound of Formula I, wherein R.sub.1 is selected from H,
C.sub.1-C.sub.6 alkyl, and C.sub.1-C.sub.6 alkoxy, and R.sub.2 is
selected from C.sub.1-C.sub.6 alkyl, phenyl, benzyl, and
--CH.sub.3-- thiophenyl. ##STR00004##
7. The plant seed or seedling of claim 6, wherein the plant seed or
seedling is further treated with one or more additional
fungicides.
8. The plant seed or seedling of claim 6 further adapted to
eradicate undesirable vegetation, wherein the plant seed or
seedling is treated with the compound of Formula I and one or more
herbicides.
9. The seed or seedling of claim 6, wherein the plant seed or
seedling is further treated with one or more additional plant
health stimulators selected from the group consisting of organic
compounds, inorganic fertilizers or micronutrient donors,
biocontrol agents and inoculants.
10. (canceled)
11. (canceled)
12. (canceled)
13. (canceled)
14. The plant seed or seedling of claim 6 further adapted to
produce a plant resistant to insect attack, wherein the plant seed
or seedling is treated with the compound of Formula I and one or
more insecticides.
15. (canceled)
16. (canceled)
17. (canceled)
18. (canceled)
19. A method of protecting a plant, from fungal attack comprising
application of a compound of Formula I, as a liquid or solid
formulation to the seedling environment, wherein R.sub.1 is
selected from H, C.sub.1-C.sub.6 alkyl, and C.sub.1-C.sub.6 alkoxy,
and R.sub.2 is selected from C.sub.1-C.sub.6 alkyl, phenyl, benzyl,
and --CH.sub.3-- thiophenyl. ##STR00005##
20. The method of claim 19, wherein R.sub.1 and R.sub.2 are each
--CH.sub.3.
21. The method of claim 1, wherein R.sub.1 and R.sub.2 are
independently selected from C.sub.1-C.sub.6 alkyl.
22. The method of claim 1, wherein the seed being treated is a
wheat seed (Triticum sp.; TRZSS).
23. The method of claim 1, wherein the compound of Formula I is
applied at a rate from about 0.5 to about 500 grams per 100
kilograms of seed.
24. The plant seed or seedling of claim 6, wherein R.sub.1 and
R.sub.2 are independently selected from C.sub.1-C.sub.6 alkyl.
25. The plant seed or seedling of claim 6, wherein R.sub.1 and
R.sub.2 are each --CH.sub.3.
26. The plant seed or seedling of claim 20, wherein the plant seed
or seedling is further treated with one or more additional
fungicides.
27. The plant seed or seedling of claim 20, wherein the plant seed
or seedling is further treated with one or more additional plant
health stimulators selected from the group consisting of organic
compounds, inorganic fertilizers or micronutrient donors,
biocontrol agents and inoculants.
28. The plant seed or seedling of claim 20, wherein: a) the plant
seed or seedling is further adapted to eradicate undesirable
vegetation and the plant seed or seedling is treated with the
compound of Formula I and one or more herbicides, and/or b) the
plant seed or seedling is further adapted to produce a plant
resistant to insect attack and the plant seed or seedling is
treated with the compound of Formula I and one or more
insecticides.
Description
CROSS REFERENCE TO RELATED APPLICATIONS
[0001] This application claims the benefit of U.S. Provisional
Patent Application Ser. No. 62/096,301 filed Dec. 23, 2014, which
is expressly incorporated by reference herein.
FIELD
[0002] The present disclosure relates to methods of controlling
phytopathogenic fungi by treating seeds with a novel seed treatment
fungicide.
BACKGROUND
[0003] In agriculture, seed treatments or seed dressings have been
used to treat seeds prior to planting. The term "seed treatment"
includes all suitable seed treatment techniques known in the art,
such as seed dressing, seed coating, seed dusting, seed imbibition
(soaking), seed foaming (i.e. covering in foam) and seed pelleting,
and refers preferably to the application of a fungicidally active
compound(s) directly to the seeds themselves, prior to planting,
and/or in their immediate vicinity during planting.
SUMMARY
[0004] An embodiment of the present disclosure may include a method
for the control or prevention of fungal attack on a plant, the
method including the steps of applying a fungicidally effective
amount of a compound of Formula I to a seed adapted to produce the
plant.
##STR00002##
[0005] One aspect of the present disclosure is a method for
controlling phytopathogenic fungi in and/or on a plant, wherein the
seeds, from which the plant is expected to grow, before sowing
and/or after pregermination, are treated with a compound of Formula
I, wherein: R.sub.1 is selected from H, C.sub.1-C.sub.6 alkyl, and
C.sub.1-C.sub.6 alkoxy, and R.sub.2 is selected from
C.sub.1-C.sub.6 alkyl, phenyl, benzyl, and
--CH.sub.3-thiophenyl.
[0006] In one exemplary embodiment, a method of treating a plant
seed to produce a plant resistant to fungal attack, wherein the
plant seed is treated with a compound of Formula I. In a more
particular embodiment, R.sub.1 and R.sub.2 are independently
selected from C.sub.1-C.sub.6 alkyl. In an even more particular
embodiment, R.sub.1 and R.sub.2 are each --CH.sub.3.
[0007] In another more particular embodiment of any of the above
embodiments, the compound of Formula I is applied at a rate from
about 0.5 to about 500 grams per 100 kilograms of seed.
[0008] In another more particular embodiment of any of the above
embodiments, the seed being treated is a wheat seed (Triticum sp.;
TRZSS).
[0009] In another more particular embodiment of any of the above
embodiments, the fungal pathogen is selected from the group
consisting of the causal agent of wheat leaf blotch (Zymoseptoria
tritici), leaf spot of sugar beets (Cercospora beticola), and leaf
spot of peanut (Cercospora arachidicola and Cercosporidium
personatum).
[0010] In another embodiment, a plant seed adapted to produce a
plant resistant to fungal and insect attack is provided. In one
exemplary embodiment, the plant seed is treated with a compound of
Formula I and one or more insecticides. In a more particular
embodiment, R.sub.1 and R.sub.2 are each --CH.sub.3.
[0011] In another embodiment, a plant seed adapted to produce a
plant resistant to fungal and insect attack is provided. In one
exemplary embodiment, the plant seed is treated with a compound of
Formula I and one or more fungicides. In a more particular
embodiment, R.sub.1 and R.sub.2 are each --CH.sub.3.
[0012] In another embodiment, a plant seed adapted to produce a
plant resistant to fungal and insect attack is provided. In one
exemplary embodiment, the plant seed is treated with a compound of
Formula I and one or more insecticides. In a more particular
embodiment, R.sub.1 and R.sub.2 are each --CH.sub.3.
[0013] In another embodiment, a plant seed adapted to produce a
plant resistant to fungal attack is provided. The plant seed is
treated with a compound of Formula I and one or more additional
health stimulators selected from the group consisting of organic
compounds, inorganic fertilizers or micronutrient donors,
biocontrol agents and inoculants. In a more particular embodiment,
R.sub.1 and R.sub.2 are each --CH.sub.3.
[0014] In another embodiment, a method of treating a plant seedling
to produce a plant resistant to fungal attack is provided. The
plant seedling is treated with a compound of Formula I. In a more
particular embodiment, R.sub.1 and R.sub.2 are each --CH.sub.3. In
another more particular embodiment of any of the above embodiments,
the seedling is a seedling of wheat (Triticum sp.; TRZSS). In
another more particular embodiment of any of the above embodiments,
the fungal pathogen is selected from the group consisting of the
causal agent of wheat leaf blotch (Zymoseptoria tritici), leaf spot
of sugar beets (Cercospora beticola), and leaf spot of peanut
(Cercospora arachidicola and Cercosporidium personatum).
[0015] In another embodiment, a plant seedling adapted to produce a
plant resistant to fungal and insect attack is provided. In one
exemplary embodiment, the plant seedling is treated with a compound
of Formula I and one or more insecticides. In a more particular
embodiment, R.sub.1 and R.sub.2 are each --CH.sub.3.
[0016] In another embodiment, a plant seedling adapted to produce a
plant resistant to fungal and insect attack is provided. In one
exemplary embodiment, the plant seedling is treated with a compound
of Formula I and one or more fungicides. In a more particular
embodiment, R.sub.1 and R.sub.2 are each --CH.sub.3.
[0017] In another embodiment, a plant seedling adapted to produce a
plant resistant to fungal and insect attack is provided. In one
exemplary embodiment, the plant seedling is treated with a compound
of Formula I and one or more insecticides. In a more particular
embodiment, R.sub.1 and R.sub.2 are each --CH.sub.3.
[0018] In another embodiment, a plant seedling adapted to produce a
plant resistant to fungal attack is provided. The plant seedling is
treated with a compound of Formula I and one or more additional
health stimulators selected from the group consisting of organic
compounds, inorganic fertilizers or micronutrient donors,
biocontrol agents and inoculants. In a more particular embodiment,
R.sub.1 and R.sub.2 are each --CH.sub.3.
[0019] In another embodiment, a plant seedling adapted to produce a
plant resistant to fungal attack. The plant seedling is treated
with a compound of Formula I. In a more particular embodiment,
R.sub.1 and R.sub.2 are each --CH.sub.3.
[0020] In another embodiment, a method of protecting a plant from
fungal attack is provided. The method comprises applying a compound
of Formula I to the seedling environment. In a more particular
embodiment, the compound of Formula I is provided as a liquid
formulation. In another more particular embodiment, the compound of
Formula I is provided as a solid formulation.
[0021] Additional features and advantages of the present disclosure
will become apparent to those skilled in the art upon consideration
of the following detailed description of the illustrative
embodiments exemplifying the best mode of carrying out the utility
described herein as presently perceived.
DETAILED DESCRIPTION OF THE DISCLOSURE
[0022] The embodiments of the disclosure described herein are not
intended to be exhaustive or to limit the disclosure to the precise
forms disclosed. Rather, the embodiments selected for description
have been chosen to enable one skilled in the art to practice the
disclosure.
[0023] Seed treatment can independently include application of a
compound of Formula I directly to the seed as a coating or
application to the seed environment as a liquid or solid
formulation. Additionally, a compound of Formula I may be applied
as a liquid or solid formulation to a seedling environment.
[0024] A seed is broadly interpreted to include anything that can
be sown and can potentially be set in place (soil) to grow a crop.
The term "seed" embraces seeds and plant propagules of all kinds
including, but not limited to, true seeds, seed pieces, grains,
suckers, corms, bulbs, fruit, tubers, cuttings, cut shoots and
similar forms, and preferably means a true seed.
[0025] A seedling is a germinated seed.
[0026] A seedling environment is the soil or other growth medium
surrounding the seedling.
[0027] The present disclosure contemplates all vehicles by which a
compound of Formula I can be formulated for delivery and use as a
seed treatment fungicide. Conventional seed treatment formulations
include for example flowable concentrates, solutions, powders for
dry treatment, water dispersible powders for slurry treatment,
water-soluble powders and emulsion and gel formulations. These
formulations can be applied diluted or undiluted.
[0028] Typically, formulations are applied following dilution of
the concentrated formulation with water as aqueous solutions,
suspensions or emulsions, or combinations thereof. Such solutions,
suspensions or emulsions may be produced from water-soluble,
water-suspendible, or emulsifiable formulations or combinations
thereof, which are solids, including and usually known as wettable
powders or water dispersible granules; or liquids including and
usually known as emulsifiable concentrates, aqueous suspensions or
suspension concentrates, and aqueous emulsions or emulsions in
water, or mixtures thereof such as suspension-emulsions. As will be
readily appreciated, any material to which this composition can be
added may be used, provided it yields the desired utility without
significant interference with the desired activity of the
pesticidally active ingredients as pesticidal agents, improves
residual lifetime, or decreases the effective concentration
required to achieve the pesticidal effect.
[0029] Wettable powders, which may be compacted to form water
dispersible granules, comprise an intimate mixture of one or more
of the pesticidally active ingredients, an inert carrier and
surfactants. The concentration of the pesticidally active
ingredient in the wettable powder is usually from about 10 percent
to about 90 percent by weight based on the total weight of the
wettable powder, more preferably about 25 weight percent to about
75 weight percent. In the preparation of wettable powder
formulations, the pesticidally active ingredients can be compounded
with any finely divided solid, such as prophyllite, talc, chalk,
gypsum, Fuller's earth, bentonite, attapulgite, starch, casein,
gluten, montmorillonite clays, diatomaceous earths, purified
silicates or the like. In such operations, the finely divided
carrier and surfactants are typically blended with the compound(s)
and milled.
[0030] Emulsifiable concentrates of the pesticidally active
ingredient comprise a convenient concentration, such as from about
10 weight percent to about 50 weight percent of the pesticidally
active ingredient, in a suitable liquid, based on the total weight
of the concentrate. The pesticidally active ingredients are
dissolved in an inert carrier, which is either a water miscible
solvent or a mixture of water-immiscible organic solvents, and
emulsifiers. The concentrates may be diluted with water and oil to
form spray mixtures in the form of oil-in-water emulsions. Useful
organic solvents include aromatics, especially the high-boiling
naphthalenic and olefinic portions of petroleum such as heavy
aromatic naphtha. Other organic solvents may also be used, such as,
for example, terpenic solvents, including rosin derivatives,
aliphatic ketones, such as cyclohexanone, and complex alcohols,
such as 2-ethoxyethanol.
[0031] Emulsifiers which can be advantageously employed herein can
be readily determined by those skilled in the art and include
various nonionic, anionic, cationic and amphoteric emulsifiers, or
a blend of two or more emulsifiers. Examples of nonionic
emulsifiers useful in preparing the emulsifiable concentrates
include the polyalkylene glycol ethers and condensation products of
alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or
fatty acids with ethylene oxide, propylene oxides such as the
ethoxylated alkyl phenols and carboxylic esters esterified with the
polyol or polyoxyalkylene. Cationic emulsifiers include quaternary
ammonium compounds and fatty amine salts. Anionic emulsifiers
include the oil-soluble salts (e.g., calcium) of alkylaryl sulfonic
acids, oil-soluble salts of sulfated polyglycol ethers and
appropriate salts of phosphated polyglycol ether.
[0032] Representative organic liquids which can be employed in
preparing emulsifiable concentrates are the aromatic liquids such
as xylene, propyl benzene fractions; or mixed naphthalene
fractions, mineral oils, substituted aromatic organic liquids such
as dioctyl phthalate; kerosene; dialkyl amides of various fatty
acids, particularly the dimethyl amides; and glycol ethers such as
the n-butyl ether, ethyl ether or methyl ether of diethylene
glycol, and the methyl ether of triethylene glycol and the like.
Mixtures of two or more organic liquids may also be employed in the
preparation of the emulsifiable concentrate. Organic liquids
include xylene, and propyl benzene fractions, with xylene being
most preferred in some cases. Surface-active dispersing agents are
typically employed in liquid formulations and in an amount of from
0.1 to 20 percent by weight based on the combined weight of the
emulsifying agents. The formulations can also contain other
compatible additives, for example, plant growth regulators and
other biologically active compounds used in agriculture.
[0033] Aqueous suspensions comprise suspensions of one or more
water-insoluble pesticidally active ingredients dispersed in an
aqueous vehicle at a concentration in the range from about 5 to
about 50 weight percent, based on the total weight of the aqueous
suspension. Suspensions are prepared by finely grinding one or more
of the pesticidally active ingredients, and vigorously mixing the
ground material into a vehicle comprised of water and surfactants
chosen from the same types discussed above. Other components, such
as inorganic salts and synthetic or natural gums, may also be added
to increase the density and viscosity of the aqueous vehicle. It is
often most effective to grind and mix at the same time by preparing
the aqueous mixture and homogenizing it in an implement such as a
sand mill, ball mill, or piston-type homogenizer.
[0034] Aqueous emulsions comprise emulsions of one or more
water-insoluble pesticidally active ingredients emulsified in an
aqueous vehicle at a concentration typically in the range from
about 5 to about 50 weight percent, based on the total weight of
the aqueous emulsion. If the pesticidally active ingredient is a
solid it must be dissolved in a suitable water-immiscible solvent
prior to the preparation of the aqueous emulsion. Emulsions are
prepared by emulsifying the liquid pesticidally active ingredient
or water-immiscible solution thereof into an aqueous medium
typically with inclusion of surfactants that aid in the formation
and stabilization of the emulsion as described above. This is often
accomplished with the aid of vigorous mixing provided by high shear
mixers or homogenizers.
[0035] The compositions of the present disclosure can also be
granular formulations, which are particularly useful for
applications to the soil. Granular formulations usually contain
from about 0.5 to about 10 weight percent, based on the total
weight of the granular formulation of the pesticidally active
ingredient(s), dispersed in an inert carrier which consists
entirely or in large part of coarsely divided inert material such
as attapulgite, bentonite, diatomite, clay or a similar inexpensive
substance. Such formulations are usually prepared by dissolving the
pesticidally active ingredients in a suitable solvent and applying
it to a granular carrier which has been preformed to the
appropriate particle size, in the range of from about 0.5 to about
3 mm. A suitable solvent is a solvent in which the compound is
substantially or completely soluble. Such formulations may also be
prepared by making a dough or paste of the carrier and the compound
and solvent, and crushing and drying to obtain the desired granular
particle.
[0036] Dusts may be prepared by intimately mixing one or more of
the pesticidally active ingredients in powdered form with a
suitable dusty agricultural carrier, such as, for example, kaolin
clay, ground volcanic rock, talc, ground bark, and the like. Dusts
can suitably contain from about 1 to about 10 weight percent of the
compounds, based on the total weight of the dust.
[0037] The formulations may additionally contain adjuvant
surfactants and polymers to enhance adhesion and flowability and
decrease dust-off of active ingredients. These adjuvants may
optionally be employed as a component of the formulation or as a
tank mix. The amount of adjuvant surfactant will typically vary
from 0.01 to 1.0 percent by volume, based on a spray-volume of
water, preferably 0.05 to 0.5 volume percent. Suitable adjuvant
surfactants include, but are not limited to ethoxylated nonyl
phenols, ethoxylated synthetic or natural alcohols, salts of the
esters of sulfosuccinic acids, ethoxylated organosilicones,
ethoxylated fatty amines and blends of surfactants with mineral or
vegetable oils. The formulations may also include oil-in-water
emulsions such as those disclosed in U.S. patent application Ser.
No. 11/495,228, the disclosure of which is expressly incorporated
by reference herein.
[0038] The formulations may optionally include combinations that
contain other pesticidal compounds. Such additional pesticidal
compounds may be fungicides, insecticides, nematocides, miticides,
arthropodicides, bactericides or combinations thereof that are
compatible with the mixtures of the disclosure described herein in
the medium selected for application, and not antagonistic to the
activity of the present mixtures. Accordingly, in such embodiments,
the other pesticidal compound is employed as a supplemental
toxicant for the same or for a different pesticidal use. The
mixtures of the present disclosure, and the pesticidal compound in
the combination can generally be present in a weight ratio of from
1:100 to 100:1.
[0039] The term "polymer" or "polymeric material" as used in this
disclosure is taken to mean either a single polymer or a
combination of different polymers or a copolymer. The particle
comprises from about 50% to about 99% by weight of the polymeric
material, preferably from about 50% to about 90% by weight.
[0040] Examples of suitable polymers for the practice of this
disclosure include but are not limited to the following
non-exhaustive list of polymers (and copolymers and mixtures
thereof): poly(methylmethacrylate); poly(lactic acid) (Chronopols
50, 95, and 100) and copolymers such as poly(lactic acid-glycolic
acid) copolymers (Lactel BP-400) and combinations with polystyrene,
for example; cellulose acetate butyrate; poly(styrene);
hydroxybutyric acid-hydroxyvaleric acid copolymers (Biopol D400G);
styrene maleic anhydride copolymers (SMA 1440 A Resin, Sartomer
Co.); poly(methylvinyl ether-maleic acid); poly(caprolactone);
poly(n-amylmethacrylate); wood rosin; polyanhydrides, e.g.,
poly(sebacic anhydride), poly(valeric anhydride), poly(trimethylene
carbonate), etc., and copolymers such as
poly(carboxyphenoxypropane-sebacic acid), poly(fumaric acid-sebacic
acid), etc.; polyorthoesters; poly(cyanoacrylates);
poly(dioxanone); ethyl cellulose; ethyl vinyl acetate polymers and
copolymers; poly(ethylene glycol); poly(vinylpyrrolidone);
acetylated mono-, di-, and triglycerides; poly(phosphazene);
chlorinated natural rubber; vinyl polymers and copolymers;
polyvinyl chloride; hydroxyalkylcelluloses; polybutadiene;
polyurethane; vinylidene chloride polymers and copolymers;
styrene-butadiene copolymers; styrene-acrylic copolymers; vinyl
acetate polymers and copolymers (e.g., vinyl acetate-ethylene
copolymers (Vinumuls) and vinyl acetate-vinylpyrrolidone
copolymers; alkylvinylether polymers and copolymers; cellulose
acetate phthalates; ethyl vinyl pthalates; cellulose triacetate;
polyanhydrides; polyglutamates; polyhydroxy butyrates; acrylic
polymers (Rhoplexes); alkyl acrylate polymers and copolymers; aryl
acrylate polymers and copolymers; aryl methacrylate polymers and
copolymers; poly(caprolactams) (i.e., the nitrogen-containing
counterparts to caprolactones); epoxy/polyamine epoxy/polyamides;
polyvinyl alcohol polymers and copolymers; polyvinyl alcohol
polymers and copolymers; silicones; polyesters (for oil-based
approaches, including alkyds); phenolics (polymers and copolymers
with drying oils).
[0041] In one embodiment, the polymer used in the compositions of
the present disclosure is selected from the group consisting of
poly(methylmethacrylate), poly(lactic acid), poly(lactic
acid-glycolic acid) copolymers, cellulose acetate butyrate,
poly(styrene), hydroxybutyric acid-hydroxyvaleric acid copolymers,
styrene maleic anhydride copolymers, poly(methylvinyl ether-maleic
acid), poly(caprolactone), poly(n-amylmethacrylate), wood rosin,
polyanhydrides, polyorthoesters, poly(cyanoacrylates),
poly(dioxanone), ethyl cellulose, ethyl vinyl acetate polymers,
poly(ethylene glycol), poly(vinylpyrrolidone), acetylated mono-,
di-, and trigylcerides, poly(phosphazene), chlorinated natural
rubber, vinyl polymers, polyvinyl chloride, hydroxyalkylcelluloses,
polybutadiene, polyurethane, vinylidene chloride polymers,
styrene-butadiene copolymers, styrene-acrylic copolymers,
alkylvinylether polymers, cellulose acetate phthalates, ethyl vinyl
pthalates, cellulose triacetate, polyanhydrides, polyglutamates,
polyhydroxy butyrates, polyvinyl acetate, vinyl acetate-ethylene
copolymers, vinyl acetate-vinylpyrrolidone copolymers, acrylic
polymers, alkyl acrylate polymers, aryl acrylate polymers, aryl
methacrylate polymers, poly(caprolactams), epoxy resins, polyamine
epoxy resins, polyamides, polyvinyl alcohol polymers, polyalkyd
resins, phenolic resins, abietic acid resins, silicones,
polyesters, and copolymers and combinations thereof.
[0042] Preferred polymers include poly(methylmethacrylate),
poly(lactic acid) (Chronopols 50, 95, or 100), and combinations
with polystyrene, poly(lactic acid-glycolic acid) copolymers
(Lactel BP-400), cellulose acetate butyrate, and poly(styrene).
[0043] Compounds of Formula I are effective in use with plants in a
disease-inhibiting and phytologically acceptable amount. The term
"disease-inhibiting and phytologically acceptable amount" refers to
an amount of a compound that kills or inhibits the plant disease
for which control is desired, but is not significantly toxic to the
plant. This amount will generally be from about 0.5 to about 500 g
ai/100 kg seed. The exact amount of a compound of Formula I
required varies with the fungal disease to be controlled, the type
of formulation employed, the method of application, the timing of
the application, the particular plant species, climate conditions,
and the like. The dilution and rate of application will depend upon
the type of equipment employed, the method and frequency of
application desired and diseases to be controlled.
[0044] A compound of Formula I may also be combined with
agricultural fungicides to form fungicidal mixtures and synergistic
mixtures thereof and be applied to a seed. The fungicidal mixtures
are often applied to control a wider variety of undesirable
diseases. When used in conjunction with other fungicide(s), a
compound of Formula I can be formulated with the other
fungicide(s), tank mixed with the other fungicide(s) or applied
sequentially with the other fungicide(s) to a seed. Such other
fungicides include, ametoctradin, azoxystrobin, Bacillus subtilis,
benalaxyl, benomyl, benthiavalicarb-isopropyl, bitertanol, bixafen,
boscalid, captan, carbendazim, carboxin, carpropamid,
chlorothalonil, Coniothyrium minitans, copper hydroxide, copper
octanoate, copper oxychloride, copper sulfate, copper sulfate
(tribasic), cuprous oxide, cyazofamid, cyflufenamid, cyproconazole,
cyprodinil, diethofencarb, difenoconazole, dimethomorph,
dimoxystrobin, enestrobin, epoxiconazole, ethaboxam, famoxadone,
fenamidone, fenarimol, fenbuconazole, fenpiclonil, fluazinam,
fludioxonil, flumorph, fluopicolide, fluopyram, fluoxastrobin,
fluquinconazole, flusilazole, flutianil, flutolanil, flutriafol,
fluxapyroxad, fosetyl, fosetyl-aluminium, guazatine, hexaconazole,
hymexazol, imazalil, imazalil sulfate, imibenconazole,
iminoctadine, iminoctadine triacetate, ipconazole, ipfenpyrazolone,
iprobenfos, iprodione, iprovalicarb, isopyrazam, isotianil,
mancozeb, mandipropamid, maneb, metalaxyl, mefenoxam, metalaxyl-M,
metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate,
metiram, metominostrobin, metrafenone, myclobutanil, ofurace,
orysastrobin, oxadixyl, oxine-copper, penconazole, penflufen,
penthiopyrad, picoxystrobin, probenazole, prochloraz, procymidone,
propamocarb, propamocarb hydrochloride, propiconazole, proquinazid,
prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin,
pyrazophos, pyribencarb, pyrimethanil, sedaxane, silthiofam,
simeconazole, spiroxamine, tebuconazole, tebufloquin,
tetraconazole, thiabendazole, thiophanate-methyl, thiram, tiadinil,
tolclofos-methyl, triadimenol, triazoxide, tricyclazole,
trifloxystrobin, triticonazole, zoxamide, Trichoderma spp.,
5-fluorocytosine and profungicides thereof, picolinamide UK-2A and
derivatives thereof.
[0045] Additionally, a compound of Formula I may be combined with
other pesticides, including insecticides, nematocides, miticides,
arthropodicides, bactericides or combinations thereof that are
compatible with the compound of Formula I in the medium selected
for application, and not antagonistic to the activity of the
compound of Formula I to form pesticidal mixtures and synergistic
mixtures thereof. A compound of Formula I can be applied in
conjunction with one or more other pesticides to control a wider
variety of undesirable pests. When used in conjunction with other
pesticides, the compound of Formula I can be formulated with the
other pesticide(s), tank mixed with the other pesticide(s) or
applied sequentially with the other pesticide(s) to a seed. Typical
insecticides include, but are not limited to: antibiotic
insecticides such as allosamidin and thuringiensin; macrocyclic
lactone insecticides such as spinosad and spinetoram; avermectin
insecticides such as abamectin, doramectin, emamectin,
eprinomectin, ivermectin and selamectin; milbemycin insecticides
such as lepimectin, milbemectin, milbemycin oxime and moxidectin;
carbamate insecticides such as bendiocarb and carbaryl;
benzofuranyl methylcarbamate insecticides such as benfuracarb,
carbofuran, carbosulfan, decarbofuran and furathiocarb;
dimethylcarbamate insecticides dimitan, dimetilan, hyquincarb and
pirimicarb; oxime carbamate insecticides such as alanycarb,
aldicarb, aldoxycarb, butocarboxim, butoxycarboxim, methomyl,
nitrilacarb, oxamyl, tazimcarb, thiocarboxime, thiodicarb and
thiofanox; phenyl methylcarbamate insecticides such as allyxycarb,
aminocarb, bufencarb, butacarb, carbanolate, cloethocarb, dicresyl,
dioxacarb, EMPC, ethiofencarb, fenethacarb, fenobucarb, isoprocarb,
methiocarb, metolcarb, mexacarbate, promacyl, promecarb, propoxur,
trimethacarb, XMC and xylylcarb; dessicant insecticides such as
boric acid, diatomaceous earth and silica gel; diamide insecticides
such as chlorantraniliprole, cyantraniliprole and flubendiamide;
dinitrophenol insecticides such as dinex, dinoprop, dinosam and
DNOC; fluorine insecticides such as barium hexafluorosilicate,
cryolite, sodium fluoride, sodium hexafluorosilicate and
sulfluramid; formamidine insecticides such as amitraz,
chlordimeform, formetanate and formparanate; fumigant insecticides
such as acrylonitrile, carbon disulfide, carbon tetrachloride,
chloroform, chloropicrin, para-dichlorobenzene,
1,2-dichloropropane, ethyl formate, ethylene dibromide, ethylene
dichloride, ethylene oxide, hydrogen cyanide, iodomethane, methyl
bromide, methylchloroform, methylene chloride, naphthalene,
phosphine, sulfuryl fluoride and tetrachloroethane; inorganic
insecticides such as borax, calcium polysulfide, copper oleate,
mercurous chloride, potassium thiocyanate and sodium thiocyanate;
chitin synthesis inhibitors such as bistrifluron, buprofezin,
chlorfluazuron, cyromazine, diflubenzuron, flucycloxuron,
flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron,
penfluron, teflubenzuron and triflumuron; juvenile hormone mimics
such as epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene,
pyriproxyfen and triprene; juvenile hormones such as juvenile
hormone I, juvenile hormone II and juvenile hormone III; moulting
hormone agonists such as chromafenozide, halofenozide,
methoxyfenozide and tebufenozide; moulting hormones such as
.alpha.-ecdysone and ecdysterone; moulting inhibitors such as
diofenolan; precocenes such as precocene I, precocene II and
precocene III; unclassified insect growth regulators such as
dicyclanil; nereistoxin analogue insecticides such as bensultap,
cartap, thiocyclam and thiosultap; nicotinoid insecticides such as
flonicamid; nitroguanidine insecticides such as clothianidin,
dinotefuran, imidacloprid and thiamethoxam; nitromethylene
insecticides such as nitenpyram and nithiazine; pyridylmethyl-amine
insecticides such as acetamiprid, imidacloprid, nitenpyram and
thiacloprid; organochlorine insecticides such as bromo-DDT,
camphechlor, DDT, pp'-DDT, ethyl-DDD, HCH, gamma-HCH, lindane,
methoxychlor, pentachlorophenol and TDE; cyclodiene insecticides
such as aldrin, bromocyclen, chlorbicyclen, chlordane, chlordecone,
dieldrin, dilor, endosulfan, alpha-endosulfan, endrin, HEOD,
heptachlor, HHDN, isobenzan, isodrin, kelevan and mirex;
organophosphate insecticides such as bromfenvinfos,
chlorfenvinphos, crotoxyphos, dichlorvos, dicrotophos,
dimethylvinphos, fospirate, heptenophos, methocrotophos, mevinphos,
monocrotophos, naled, naftalofos, phosphamidon, propaphos, TEPP and
tetrachlorvinphos; organothiophosphate insecticides such as
dioxabenzofos, fosmethilan and phenthoate; aliphatic
organothiophosphate insecticides such as acethion, amiton,
cadusafos, chlorethoxyfos, chlormephos, demephion, demephion-O,
demephion-S, demeton, demeton-O, demeton-S, demeton-methyl,
demeton-O-methyl, demeton-S-methyl, demeton-S-methylsulphon,
disulfoton, ethion, ethoprophos, IP SP, isothioate, malathion,
methacrifos, oxydemeton-methyl, oxydeprofos, oxydisulfoton,
phorate, sulfotep, terbufos and thiometon; aliphatic amide
organothiophosphate insecticides such as amidithion, cyanthoate,
dimethoate, ethoate-methyl, formothion, mecarbam, omethoate,
prothoate, sophamide and vamidothion; oxime organothiophosphate
insecticides such as chlorphoxim, phoxim and phoxim-methyl;
heterocyclic organothiophosphate insecticides such as azamethiphos,
coumaphos, coumithoate, dioxathion, endothion, menazon,
morphothion, phosalone, pyraclofos, pyridaphenthion and quinothion;
benzothiopyran organothiophosphate insecticides such as dithicrofos
and thicrofos; benzotriazine organothiophosphate insecticides such
as azinphos-ethyl and azinphos-methyl; isoindole
organothiophosphate insecticides such as dialifos and phosmet;
isoxazole organothiophosphate insecticides such as isoxathion and
zolaprofos; pyrazolopyrimidine organothiophosphate insecticides
such as chlorprazophos and pyrazophos; pyridine organothiophosphate
insecticides such as chlorpyrifos and chlorpyrifos-methyl;
pyrimidine organothiophosphate insecticides such as butathiofos,
diazinon, etrimfos, lirimfos, pirimiphos-ethyl, pirimiphos-methyl,
primidophos, pyrimitate and tebupirimfos; quinoxaline
organothiophosphate insecticides such as quinalphos and
quinalphos-methyl; thiadiazole organothiophosphate insecticides
such as athidathion, lythidathion, methidathion and prothidathion;
triazole organothiophosphate insecticides such as isazofos and
triazophos; phenyl organothiophosphate insecticides such as
azothoate, bromophos, bromophos-ethyl, carbophenothion,
chlorthiophos, cyanophos, cythioate, dicapthon, dichlofenthion,
etaphos, famphur, fenchlorphos, fenitrothion fensulfothion,
fenthion, fenthion-ethyl, heterophos, jodfenphos, mesulfenfos,
parathion, parathion-methyl, phenkapton, phosnichlor, profenofos,
prothiofos, sulprofos, temephos, trichlormetaphos-3 and trifenofos;
phosphonate insecticides such as butonate and trichlorfon;
phosphonothioate insecticides such as mecarphon; phenyl
ethylphosphonothioate insecticides such as fonofos and
trichloronat; phenyl phenylphosphonothioate insecticides such as
cyanofenphos, EPN and leptophos; phosphoramidate insecticides such
as crufomate, fenamiphos, fosthietan, mephosfolan, phosfolan and
pirimetaphos; phosphoramidothioate insecticides such as acephate,
isocarbophos, isofenphos, isofenphos-methyl, methamidophos and
propetamphos; phosphorodiamide insecticides such as dimefox,
mazidox, mipafox and schradan; oxadiazine insecticides such as
indoxacarb; oxadiazoline insecticides such as metoxadiazone;
phthalimide insecticides such as dialifos, phosmet and
tetramethrin; pyrazole insecticides such as tebufenpyrad,
tolefenpyrad; phenylpyrazole insecticides such as acetoprole,
ethiprole, fipronil, pyrafluprole, pyriprole and vaniliprole;
pyrethroid ester insecticides such as acrinathrin, allethrin,
bioallethrin, barthrin, bifenthrin, bioethanomethrin, cyclethrin,
cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,
gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin,
alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,
zeta-cypermethrin, cyphenothrin, deltamethrin, dimefluthrin,
dimethrin, empenthrin, fenfluthrin, fenpirithrin, fenpropathrin,
fenvalerate, esfenvalerate, flucythrinate, fluvalinate,
tau-fluvalinate, furethrin, imiprothrin, meperfluthrin,
metofluthrin, permethrin, biopermethrin, transpermethrin,
phenothrin, prallethrin, profluthrin, pyresmethrin, resmethrin,
bioresmethrin, cismethrin, tefluthrin, terallethrin, tetramethrin,
tetramethylfluthrin, tralomethrin and transfluthrin; pyrethroid
ether insecticides such as etofenprox, flufenprox, halfenprox,
protrifenbute and silafluofen; pyrimidinamine insecticides such as
flufenerim and pyrimidifen; pyrrole insecticides such as
chlorfenapyr; tetramic acid insecticides such as spirotetramat;
tetronic acid insecticides such as spiromesifen; thiourea
insecticides such as diafenthiuron; urea insecticides such as
flucofuron and sulcofuron; and unclassified insecticides such as
closantel, copper naphthenate, crotamiton, EXD, fenazaflor,
fenoxacrim, hydramethylnon, isoprothiolane, malonoben,
metaflumizone, nifluridide, plifenate, pyridaben, pyridalyl,
pyrifluquinazon, rafoxanide, sulfoxaflor, triarathene and
triazamate, and any combinations thereof.
[0046] Additionally, a compound of Formula I may be combined with
herbicides that are compatible with the compound of Formula I in
the medium selected for application, and not antagonistic to the
activity of the compound of Formula I to form pesticidal mixtures
and synergistic mixtures thereof. The compound of Formula I may be
applied in conjunction with one or more herbicides to control a
wide variety of undesirable plants. When used in conjunction with
herbicides, a compound of Formula I may be formulated with the
herbicide(s), tank mixed with the herbicide(s) or applied
sequentially with the herbicide(s). Typical herbicides may include,
but are not limited to: amide herbicides such as allidochlor,
beflubutamid, benzadox, benzipram, bromobutide, cafenstrole, CDEA,
cyprazole, dimethenamid, dimethenamid-P, diphenamid, epronaz,
etnipromid, fentrazamide, flupoxam, fomesafen, halosafen,
isocarbamid, isoxaben, napropamide, naptalam, pethoxamid,
propyzamide, quinonamid and tebutam; anilide herbicides such as
chloranocryl, cisanilide, clomeprop, cypromid, diflufenican,
etobenzanid, fenasulam, flufenacet, flufenican, mefenacet,
mefluidide, metamifop, monalide, naproanilide, pentanochlor,
picolinafen and propanil; arylalanine herbicides such as
benzoylprop, flamprop and flamprop-M; chloroacetanilide herbicides
such as acetochlor, alachlor, butachlor, butenachlor, delachlor,
diethatyl, dimethachlor, metazachlor, metolachlor, S-metolachlor,
pretilachlor, propachlor, propisochlor, prynachlor, terbuchlor,
thenylchlor and xylachlor; sulfonanilide herbicides such as
benzofluor, perfluidone, pyrimisulfan and profluazol; sulfonamide
herbicides such as asulam, carbasulam, fenasulam and oryzalin;
thioamide herbicides such as chlorthiamid; antibiotic herbicides
such as bilanafos; benzoic acid herbicides such as chloramben,
dicamba, 2,3,6-TBA and tricamba; pyrimidinyloxybenzoic acid
herbicides such as bispyribac and pyriminobac;
pyrimidinylthiobenzoic acid herbicides such as pyrithiobac;
phthalic acid herbicides such as chlorthal; picolinic acid
herbicides such as aminopyralid, clopyralid and picloram;
quinolinecarboxylic acid herbicides such as quinclorac and
quinmerac; arsenical herbicides such as cacodylic acid, CMA, DSMA,
hexaflurate, MAA, MAMA, MSMA, potassium arsenite and sodium
arsenite; benzoylcyclohexanedione herbicides such as mesotrione,
sulcotrione, tefuryltrione and tembotrione; benzofuranyl
alkylsulfonate herbicides such as benfuresate and ethofumesate;
benzothiazole herbicides such as benzazolin; carbamate herbicides
such as asulam, carboxazole chlorprocarb, dichlormate, fenasulam,
karbutilate and terbucarb; carbanilate herbicides such as barban,
BCPC, carbasulam, carbetamide, CEPC, chlorbufam, chlorpropham,
CPPC, desmedipham, phenisopham, phenmedipham, phenmedipham-ethyl,
propham and swep; cyclohexene oxime herbicides such as alloxydim,
butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim,
sethoxydim, tepraloxydim and tralkoxydim; cyclopropylisoxazole
herbicides such as isoxachlortole and isoxaflutole; dicarboximide
herbicides such as cinidon-ethyl, flumezin, flumiclorac,
flumioxazin and flumipropyn; dinitroaniline herbicides such as
benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin,
isopropalin, methalpropalin, nitralin, oryzalin, pendimethalin,
prodiamine, profluralin and trifluralin; dinitrophenol herbicides
such as dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC,
etinofen and medinoterb; diphenyl ether herbicides such as
ethoxyfen; nitrophenyl ether herbicides such as acifluorfen,
aclonifen, bifenox, chlomethoxyfen, chlornitrofen, etnipromid,
fluorodifen, fluoroglycofen, fluoronitrofen, fomesafen,
furyloxyfen, halosafen, lactofen, nitrofen, nitrofluorfen and
oxyfluorfen; dithiocarbamate herbicides such as dazomet and metam;
halogenated aliphatic herbicides such as alorac, chloropon,
dalapon, flupropanate, hexachloroacetone, iodomethane, methyl
bromide, monochloroacetic acid, SMA and TCA; imidazolinone
herbicides such as imazamethabenz, imazamox, imazapic, imazapyr,
imazaquin and imazethapyr; inorganic herbicides such as ammonium
sulfamate, borax, calcium chlorate, copper sulfate, ferrous
sulfate, potassium azide, potassium cyanate, sodium azide, sodium
chlorate and sulfuric acid; nitrite herbicides such as bromobonil,
bromoxynil, chloroxynil, dichlobenil, iodobonil, ioxynil and
pyraclonil; organophosphorus herbicides such as amiprofos-methyl,
anilofos, bensulide, bilanafos, butamifos, 2,4-DEP, DMPA, EBEP,
fosamine, glufosinate, glufosinate-P, glyphosate and piperophos;
phenoxy herbicides such as bromofenoxim, clomeprop, 2,4-DEB,
2,4-DEP, difenopenten, disul, erbon, etnipromid, fenteracol and
trifopsime; oxadiazoline herbicides such as methazole, oxadiargyl,
oxadiazon; oxazole herbicides such as fenoxasulfone; phenoxyacetic
herbicides such as 4-CPA, 2,4-D, 3,4-DA, MCPA, MCPA-thioethyl and
2,4,5-T; phenoxybutyric herbicides such as 4-CPB, 2,4-DB, 3,4-DB,
MCPB and 2,4,5-TB; phenoxypropionic herbicides such as cloprop,
4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecoprop and
mecoprop-P; aryloxyphenoxypropionic herbicides such as chlorazifop,
clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P,
fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P,
isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P
and trifop; phenylenediamine herbicides such as dinitramine and
prodiamine; pyrazole herbicides such as pyroxasulfone;
benzoylpyrazole herbicides such as benzofenap, pyrasulfotole,
pyrazolynate, pyrazoxyfen, and topramezone; phenylpyrazole
herbicides such as fluazolate, nipyraclofen, pioxaden and
pyraflufen; pyridazine herbicides such as credazine, pyridafol and
pyridate; pyridazinone herbicides such as brompyrazon, chloridazon,
dimidazon, flufenpyr, metflurazon, norflurazon, oxapyrazon and
pydanon; pyridine herbicides such as aminopyralid, cliodinate,
clopyralid, dithiopyr, fluroxypyr, haloxydine, picloram,
picolinafen, pyriclor, thiazopyr and triclopyr; pyrimidinediamine
herbicides such as iprymidam and tioclorim; quaternary ammonium
herbicides such as cyperquat, diethamquat, difenzoquat, diquat,
morfamquat and paraquat; thiocarbamate herbicides such as butylate,
cycloate, di-allate, EPTC, esprocarb, ethiolate, isopolinate,
methiobencarb, molinate, orbencarb, pebulate, prosulfocarb,
pyributicarb, sulfallate, thiobencarb, tiocarbazil, tri-allate and
vernolate; thiocarbonate herbicides such as dimexano, EXD and
proxan; thiourea herbicides such as methiuron; triazine herbicides
such as dipropetryn, indaziflam, triaziflam and trihydroxytriazine;
chlorotriazine herbicides such as atrazine, chlorazine, cyanazine,
cyprazine, eglinazine, ipazine, mesoprazine, procyazine,
proglinazine, propazine, sebuthylazine, simazine, terbuthylazine
and trietazine; methoxytriazine herbicides such as atraton,
methometon, prometon, secbumeton, simeton and terbumeton;
methylthiotriazine herbicides such as ametryn, aziprotryne,
cyanatryn, desmetryn, dimethametryn, methoprotryne, prometryn,
simetryn and terbutryn; triazinone herbicides such as ametridione,
amibuzin, hexazinone, isomethiozin, metamitron and metribuzin;
triazole herbicides such as amitrole, cafenstrole, epronaz and
flupoxam; triazolone herbicides such as amicarbazone, bencarbazone,
carfentrazone, flucarbazone, ipfencarbazone, propoxycarbazone,
sulfentrazone and thiencarbazone-methyl; triazolopyrimidine
herbicides such as cloransulam, diclosulam, florasulam,
flumetsulam, metosulam, penoxsulam and pyroxsulam; uracil
herbicides such as benzfendizone, bromacil, butafenacil,
flupropacil, isocil, lenacil, saflufenacil and terbacil; urea
herbicides such as benzthiazuron, cumyluron, cycluron,
dichloralurea, diflufenzopyr, isonoruron, isouron,
methabenzthiazuron, monisouron and noruron; phenylurea herbicides
such as anisuron, buturon, chlorbromuron, chloreturon,
chlorotoluron, chloroxuron, daimuron, difenoxuron, dimefuron,
diuron, fenuron, fluometuron, fluothiuron, isoproturon, linuron,
methiuron, methyldymron, metobenzuron, metobromuron, metoxuron,
monolinuron, monuron, neburon, parafluron, phenobenzuron, siduron,
tetrafluron and thidiazuron; pyrimidinylsulfonylurea herbicides
such as amidosulfuron, azimsulfuron, bensulfuron, chlorimuron,
cyclosulfamuron, ethoxysulfuron, flazasulfuron, flucetosulfuron,
flupyrsulfuron, foramsulfuron, halosulfuron, imazosulfuron,
mesosulfuron, metazosulfuron, nicosulfuron, orthosulfamuron,
oxasulfuron, primisulfuron, propyrisulfuron, pyrazosulfuron,
rimsulfuron, sulfometuron, sulfosulfuron and trifloxysulfuron;
triazinylsulfonylurea herbicides such as chlorsulfuron,
cinosulfuron, ethametsulfuron, iodosulfuron, metsulfuron,
prosulfuron, thifensulfuron, triasulfuron, tribenuron,
triflusulfuron and tritosulfuron; thiadiazolylurea herbicides such
as buthiuron, ethidimuron, tebuthiuron, thiazafluron and
thidiazuron; and unclassified herbicides such as acrolein, allyl
alcohol, aminocyclopyrachlor, azafenidin, bentazone, benzobicyclon,
bicyclopyrone, buthidazole, calcium cyanamide, cambendichlor,
chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol,
cinmethylin, clomazone, CPMF, cresol, cyanamide,
ortho-dichlorobenzene, dimepiperate, endothal, fluoromidine,
fluridone, flurochloridone, flurtamone, fluthiacet, indanofan,
methyl isothiocyanate, OCH, oxaziclomefone, pentachlorophenol,
pentoxazone, phenylmercury acetate, prosulfalin, pyribenzoxim,
pyriftalid, quinoclamine, rhodethanil, sulglycapin, thidiazimin,
tridiphane, trimeturon, tripropindan and tritac.
[0047] The seed treatment mixture can also comprise or may be
applied together and/or sequentially with further active compounds.
These further compounds can be plant health stimulants, such as
organic compounds, inorganic fertilizers, or micronutrient donors
or other preparations that influence plant growth, such as
inoculants.
[0048] In another embodiment, the seed treatment mixture can also
comprise or may be applied together and/or sequentially with other
biological organisms, such as, but not limited to the group
consisting of Bacillus strains, for example Bacillus subtilis var.
amyloiquefaciens FZB24 (TAEGRP.RTM.) and Bacillus amyloiquefaciens
FZB42 (RHIZOVITAL.RTM.), and/or mutants and metabolites of the
respective strains that exhibit activity against insects, mites,
nematodaes, and/or phytopathogens.
[0049] Another embodiment of the present disclosure is a method for
the control or prevention of fungal attack. This method comprises
applying to the seed a fungicidally effective amount of a compound
of Formula I. A compound of Formula I is suitable for treatment of
various plants at fungicidal levels, while exhibiting low
phytotoxicity. The compound may be useful both in a protectant
and/or an eradicant fashion.
[0050] Compounds of Formula I have been found to have significant
fungicidal effects particularly for agricultural use. Compounds of
Formula I are particularly effective for use with agricultural
crops and horticultural plants. Additional benefits may include,
but are not limited to, improving the health of a plant; improving
the yield of a plant (e.g. increased biomass and/or increased
content of valuable ingredients); improving the vigor of a plant
(e.g. improved plant growth and/or greener leaves); improving the
quality of a plant (e.g. improved content or composition of certain
ingredients); and improving the tolerance to abiotic and/or biotic
stress of the plant.
[0051] It will be understood by those in the art that the efficacy
of compounds of Formula I for the following fungi establish the
general utility of the compounds as fungicides.
[0052] Compounds of Formula I have broad ranges of activity against
fungal pathogens. Exemplary pathogens may include, but are not
limited to, wheat leaf blotch (Zymoseptoria trilici), leaf spot of
sugar beets (Cercospora beticola), leaf spot of peanut (Cercospora
arachidicola and Cercosporidium personatum). The exact amount of
the active material to be applied is dependent not only on the
specific formulation being applied, but also on the particular
action desired, the fungal species to be controlled, and the stage
of growth thereof, as well as the part of the plant or other
product to be contacted with the compound.
[0053] Any range or desired value given herein may be extended or
altered without losing the effects sought, as is apparent to the
skilled person for an understanding of the teachings herein.
Examples
[0054] Evaluation of Fungicidal Activity as a Seed Treatment for
Leaf Blotch of Wheat (Zymoseptoria trilici; Bayer code SEPTTR):
Seeds of wheat cultivar `Yuma` were treated with seed dye and a 10%
suspension concentrate formulation of compound 1 at rates of 300,
100, 33.3, 11, 3.7, and 0 grams active ingredient/100 kilograms
seeds (g ai/100 kg seeds). The treated seeds were planted in pots
containing 50% mineral soil/50% soil-less metro mix 12 days after
treatment, with 10 seeds per pot, and grown in a greenhouse at
20.degree. C. Four pots of 7-day old seedlings were inoculated with
an aqueous spore suspension of Z. trilici and after inoculation the
plants were kept in 100% relative humidity to permit spores to
germinate and infect the leaf. The plants were then transferred to
a greenhouse set at 20.degree. C. for disease development.
[0055] The activity of various compounds of Formula I when
evaluated in these experiments are presented in Table 2. The
effectiveness of compounds of Formula I in controlling disease was
determined by assessing the severity of disease on treated plants,
then converting the severity to percent control based on the level
of disease on untreated, inoculated plants.
[0056] The test results indicated compound 1 was very active
against Z. tritici, providing 93% disease control at the 11 gai/100
kg seeds rate.
[0057] Control of foliar diseases with these seed treatment
applications demonstrates that the experimental compound is taken
up into the xylem and redistributed to leaves in an amount
sufficient to provide protectant disease control from a seed
treatment. Further, there was no evidence of stunting or
phytotoxicity from applications of compound 1, even at the highest
rates tested. Excellent disease control without phytotoxicity
indicates that the classes of chemistry represented by compounds of
Formula I have potential utility as seed treatments.
TABLE-US-00001 TABLE 1 Biological Activity Rating Scale. % Disease
Control Rating 76-100 A 51-75 B 26-50 C 0-25 D Not Tested E
TABLE-US-00002 TABLE 2 Foliar Disease Control Of Seed Treatments
Utilizing Compounds Of Formula I. Cmpd. Rate No.* R.sub.1 R.sub.2
(g ai/100 kg seeds)* SEPTTR* 1 CH.sub.3 CH.sub.3 300 A 100 A 33.3 A
11 A 3.7 D Cmpd. No.--Compound Number *g ai/100 kg seeds--grams
active ingredient per 100 kilogram of seeds SEPTTR--Wheat Leaf
Blotch (Zymoseptoria tritici)
* * * * *