U.S. patent application number 16/923338 was filed with the patent office on 2020-10-29 for synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1h)-one for fungal control (sbi).
This patent application is currently assigned to Adama Makhteshim Ltd.. The applicant listed for this patent is Adama Makhteshim Ltd.. Invention is credited to Beth Lorsbach, W. John Owen, Chenglin Yao.
Application Number | 20200337309 16/923338 |
Document ID | / |
Family ID | 1000004954116 |
Filed Date | 2020-10-29 |
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United States Patent
Application |
20200337309 |
Kind Code |
A1 |
Owen; W. John ; et
al. |
October 29, 2020 |
Synergistic Fungicidal Mixtures and Compositions Comprising
5-Fluoro-4-Imino-3-Methyl-1-Tosyl-3,4-Dihydropyrimidin-2(1h)-One
for Fungal Control (SBI)
Abstract
A fungicidal composition containing a fungicidally effective
amount of the compound of Formula I: ##STR00001##
5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one,
and at least one fungicide to provide synergistic control of
selected fungi wherein the at least one fungicide is a fungicidal
sterol biosynthesis-inhibitor.
Inventors: |
Owen; W. John; (Carmel,
IN) ; Yao; Chenglin; (Carmel, IN) ; Lorsbach;
Beth; (Indianapolis, IN) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Adama Makhteshim Ltd. |
Beer Sheva |
|
IL |
|
|
Assignee: |
Adama Makhteshim Ltd.
Beer Sheva
IL
|
Family ID: |
1000004954116 |
Appl. No.: |
16/923338 |
Filed: |
July 8, 2020 |
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Application
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16830623 |
Mar 26, 2020 |
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16923338 |
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16701303 |
Dec 3, 2019 |
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16830623 |
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16547209 |
Aug 21, 2019 |
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16701303 |
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16021977 |
Jun 28, 2018 |
10426165 |
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16547209 |
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15377845 |
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10045533 |
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16021977 |
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14585945 |
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9526245 |
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15377845 |
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61922616 |
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61922630 |
Dec 31, 2013 |
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61922640 |
Dec 31, 2013 |
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Current U.S.
Class: |
1/1 |
Current CPC
Class: |
A01N 47/08 20130101;
A01N 43/40 20130101; A01N 43/88 20130101; A01N 37/50 20130101; A01N
43/56 20130101; A01N 45/02 20130101; A01N 47/14 20130101; A01N
47/24 20130101; A01N 47/04 20130101; A01N 37/34 20130101; A01N
43/54 20130101; A01N 43/653 20130101 |
International
Class: |
A01N 43/54 20060101
A01N043/54; A01N 37/34 20060101 A01N037/34; A01N 37/50 20060101
A01N037/50; A01N 43/40 20060101 A01N043/40; A01N 43/56 20060101
A01N043/56; A01N 43/88 20060101 A01N043/88; A01N 47/08 20060101
A01N047/08; A01N 43/653 20060101 A01N043/653; A01N 45/02 20060101
A01N045/02; A01N 47/04 20060101 A01N047/04; A01N 47/14 20060101
A01N047/14; A01N 47/24 20060101 A01N047/24 |
Claims
1. A synergistic fungicidal mixture, comprising: a fungicidally
effective amount of the compound of Formula I: ##STR00026## and at
least one additional fungicide in which the at least one additional
fungicide is a fungicidal sterol biosynthesis inhibitor.
2. The mixture of claim 1 in which the at least one additional
fungicide is selected from the group consisting of epoxiconazole,
cyproconazole, myclobutanil, metconazole, propiconazole,
prothioconazole, fluquinconazole, flutriafol, and
difenoconazole.
3. The mixture of claim 2 in which the concentration ratio of the
Compound of Formula I to prothioconazole is between about 1:21.6
and about 2:1.
4. The mixture of claim 2 in which the concentration ratio of the
Compound of Formula I to epoxiconazole is between about 3.6:1 and
about 20:1.
5. The mixture of claim 2 in which the concentration ratio of the
Compound of Formula I to cyproconazole is between about 1:3 and
about 4.5:1.
6. The mixture of claim 2 in which the concentration ratio of the
Compound of Formula I to myclobutanil is between about 1:27 and
about 1:4.
7. The mixture of claim 2 in which the concentration ratio of the
Compound of Formula I to metconazole is between about 2.2:1 and
about 30:1.
8. The mixture of claim 2 in which the concentration ratio of the
Compound of Formula I to difenoconazole is between about 120:1 and
about 787:1.
9. The mixture of claim 2 in which the concentration ratio of the
Compound of Formula I to propiconazole is between about 1:2.1 and
about 30:1.
10. The mixture of claim 2 in which the concentration ratio of the
Compound of Formula I to fluquinconazole is between about 1:1.3 and
about 170:1.
11. The mixture of claim 2 in which the concentration ratio of the
Compound of Formula I to flutriafol is between about 1:20.6 and
about 5.1:1.
12. The mixtures of claims 1-11, wherein the mixture provides
control of a fungal pathogen and the fungal pathogen is one of Leaf
Blotch of Wheat (Mycosphaerella graminicola; anamorph: Septoria
tritici), Wheat Brown Rust (Puccinia triticina), Stripe Rust
(Puccinia striiformis f. sp. tritici), Scab of Apple (Venturia
inaequalis), Blister Smut of Maize (Ustilago maydis), Powdery
Mildew of Grapevine (Uncinula necator), Barley scald
(Rhynchosporium secalis), Blast of Rice (Magnaporthe grisea), Rust
of Soybean (Phakopsora pachyrhizi), Glume Blotch of Wheat
(Leptosphaeria nodorum), Powdery Mildew of Wheat (Blumeria graminis
f. sp. tritici), Powdery Mildew of Barley (Blumeria graminis f. sp.
hordei), Powdery Mildew of Cucurbits (Erysiphe cichoracearum),
Anthracnose of Cucurbits (Glomerella lagenarium), Leaf Spot of Beet
(Cercospora beticola), Early Blight of Tomato (Alternaria solani),
and Net Blotch of Barley (Pyrenophora teres).
13. The mixtures of claims 1-11, wherein the mixture provides
control of a fungal pathogen and the fungal pathogen is Leaf Blotch
of Wheat (Mycosphaerella graminicola; anamorph: Septoria
tritici).
14. The mixture of claim 2, wherein the mixture provides control of
a fungal pathogen and the fungal pathogen is one of Leaf Blotch of
Wheat (Mycosphaerella graminicola; anamorph: Septoria tritici),
Wheat Brown Rust (Puccinia triticina), Stripe Rust (Puccinia
striiformis f. sp. tritici), Scab of Apple (Venturia inaequalis),
Blister Smut of Maize (Ustilago maydis), Powdery Mildew of
Grapevine (Uncinula necator), Barley scald (Rhynchosporium
secalis), Blast of Rice (Magnaporthe grisea), Rust of Soybean
(Phakopsora pachyrhizi), Glume Blotch of Wheat (Leptosphaeria
nodorum), Powdery Mildew of Wheat (Blumeria graminis f. sp.
tritici), Powdery Mildew of Barley (Blumeria graminis f. sp.
hordei), Powdery Mildew of Cucurbits (Erysiphe cichoracearum),
Anthracnose of Cucurbits (Glomerella lagenarium), Leaf Spot of Beet
(Cercospora beticola), Early Blight of Tomato (Alternaria solani),
and Net Blotch of Barley (Pyrenophora teres).
15. The mixture of claim 2, wherein the mixture provides control of
a fungal pathogen and the fungal pathogen is Leaf Blotch of Wheat
(Mycosphaerella graminicola; anamorph: Septoria tritici).
16. A synergistic, fungicidal composition comprising a fungicidally
effective amount of the mixtures of claims 1-11 and an
agriculturally acceptable adjuvant or carrier.
17. The mixture of claim 1 in which the at least one additional
fungicide is prothioconazole.
18. The mixture of claim 1 in which the at least one additional
fungicide is epoxiconazole.
Description
CROSS REFERENCE TO RELATED APPLICATIONS
[0001] This application claims the benefit of U.S. Provisional
Patent Application Ser. Nos. 61/922,616, 61/922,630, and
61/922,640, all filed Dec. 31, 2013, which are expressly
incorporated by reference herein.
FIELD OF THE INVENTION
[0002] This disclosure concerns a synergistic fungicidal
composition containing (a) a compound of Formula I and (b) at least
one fungicide selected from the group consisting of a strobilurin,
for example pyraclostrobin, fluoxastrobin, azoxystrobin,
trifloxystrobin, picoxystrobin, and kresoxim-methyl; a succinate
dehydrogenase-inhibitor (SDHI), for example fluxapyroxad,
benzovindiflupyr, penthiopyrad, isopyrazam, bixafen, boscalid,
penflufen, and fluopyram; an ergosterol biosynthesis-inhibitor
(SBI), for example prothioconazole, epoxiconazole, cyproconazole,
myclobutanil, prochloraz, metconazole, difenoconazole,
tebuconazole, tetraconazole, fenbuconazole, propiconazole,
fluquinconazole, flusilazole, flutriafol, and fenpropimorph; and a
multi-site-inhibitor, for example mancozeb and chlorothalonil, or
other commercial fungicides to provide control of any plant fungal
pathogen.
BACKGROUND AND SUMMARY
[0003] Fungicides are compounds, of natural or synthetic origin,
which act to protect plants against damage caused by fungi. Current
methods of agriculture rely heavily on the use of fungicides. In
fact, some crops cannot be grown usefully without the use of
fungicides. Using fungicides allows a grower to increase the yield
and the quality of the crop, and consequently, increase the value
of the crop. In most situations, the increase in value of the crop
is worth at least three times the cost of the use of the
fungicide.
[0004] However, no one fungicide is useful in all situations and
repeated usage of a single fungicide frequently leads to the
development of resistance to that and related fungicides.
Consequently, research is being conducted to produce fungicides and
combinations of fungicides that are safer, that have better
performance, that require lower dosages, that are easier to use,
and that cost less.
[0005] Synergism occurs when the activity of two or more compounds
exceeds the activities of the compounds when used alone.
[0006] It is an object of this disclosure to provide synergistic
compositions comprising fungicidal compounds. It is a further
object of this disclosure to provide processes that use these
synergistic compositions. The synergistic compositions are capable
of preventing or curing, or both, diseases caused by fungi of the
classes Ascomycetes and Basidiomycetes. In addition, the
synergistic compositions have improved efficacy against the
Ascomycete and Basidiomycete pathogens, including leaf blotch and
brown rust of wheat. In accordance with this disclosure,
synergistic compositions are provided along with methods for their
use.
[0007] According to an exemplary embodiment of the present
disclosure, a synergistic fungicidal mixture is provided including
a fungicidally effective amount of the compound of Formula I, and
at least one fungicide selected from the group consisting of a
fungicidal sterol biosynthesis inhibitor (SBI).
[0008] According to another exemplary embodiment of the present
disclosure, a synergistic fungicidal mixture is provided including
a fungicidally effective amount of the compound of Formula I, and
at least one additional fungicide in which the at least one
additional fungicide is a fungicidal sterol biosynthesis inhibitor
(SBI).
[0009] According to yet another exemplary embodiment of the present
disclosure, a synergistic, fungicidal composition is provided
including a fungicidally effective amount of the mixture and an
agriculturally acceptable adjuvant or carrier.
[0010] In certain embodiments, the SBI and/or the at least one
additional fungicide is selected from the group consisting of
epoxiconazole, cyproconazole, myclobutanil, metconazole,
propiconazole, prothioconazole, fluquinconazole, flutriafol, and
difenoconazole.
[0011] In certain embodiments, the SBI and/or the at least one
additional fungicide is prothioconazole.
[0012] In certain embodiments, the SBI and/or the at least one
additional fungicide is epoxiconazole.
[0013] In certain embodiments, the concentration ratio of the
Compound of Formula I to prothioconazole is between about 1:21.6
and about 2:1.
[0014] In certain embodiments, the concentration ratio of the
Compound of Formula I to epoxiconazole is between about 3.6:1 and
about 20:1.
[0015] In certain embodiments, the concentration ratio of the
Compound of Formula I to cyproconazole is between about 1:3 and
about 4.5:1.
[0016] In certain embodiments, the concentration ratio of the
Compound of Formula I to myclobutanil is between about 1:27 and
about 1:4.
[0017] In certain embodiments, the concentration ratio of the
Compound of Formula I to metconazole is between about 2.2:1 and
about 30:1.
[0018] In certain embodiments, the concentration ratio of the
Compound of Formula I to difenoconazole is between about 120:1 and
about 787:1.
[0019] In certain embodiments, the concentration ratio of the
Compound of Formula I to propiconazole is between about 1:2.1 and
about 30:1.
[0020] In certain embodiments, the concentration ratio of the
Compound of Formula I to fluquinconazole is between about 1:1.3 and
about 170:1.
[0021] In certain embodiments, the concentration ratio of the
Compound of Formula I to flutriafol is between about 1:20.6 and
about 5.1:1.
[0022] In certain embodiments, the mixture provides control of a
fungal pathogen and the fungal pathogen is one of Leaf Blotch of
Wheat (Mycosphaerella graminicola; anamorph: Septoria tritici),
Wheat Brown Rust (Puccinia triticina), Stripe Rust (Puccinia
striiformis f. sp. tritici), Scab of Apple (Venturia inaequalis),
Blister Smut of Maize (Ustilago maydis), Powdery Mildew of
Grapevine (Uncinula necator), Barley scald (Rhynchosporium
secalis), Blast of Rice (Magnaporthe grisea), Rust of Soybean
(Phakopsora pachyrhizi), Glume Blotch of Wheat (Leptosphaeria
nodorum), Powdery Mildew of Wheat (Blumeria graminis f. sp.
tritici), Powdery Mildew of Barley (Blumeria graminis f. sp.
hordei), Powdery Mildew of Cucurbits (Erysiphe cichoracearum),
Anthracnose of Cucurbits (Glomerella lagenarium), Leaf Spot of Beet
(Cercospora beticola), Early Blight of Tomato (Alternaria solani),
and Net Blotch of Barley (Pyrenophora teres).
[0023] In certain embodiments, the mixture provides control of a
fungal pathogen and the fungal pathogen is Leaf Blotch of Wheat
(Mycosphaerella graminicola; anamorph: Septoria tritici).
DETAILED DESCRIPTION
[0024] The present disclosure concerns a synergistic fungicidal
mixture comprising a fungicidally effective amount of (a) a
compound of Formula I and (b) at least one fungicide selected from
the group consisting of a strobilurin, for example pyraclostrobin,
fluoxastrobin, azoxystrobin, trifloxystrobin, picoxystrobin, and
kresoxim-methyl, a succinate dehydrogenase-inhibitor, for example
fluxapyroxad, benzovindiflupyr, penthiopyrad, isopyrazam, bixafen,
boscalid, penflufen, and fluopyram, an ergosterol
biosynthesis-inhibitor, for example prothioconazole, epoxiconazole,
cyproconazole, myclobutanil, prochloraz, metconazole,
difenoconazole, tebuconazole, tetraconazole, fenbuconazole,
propiconazole, fluquinconazole, flusilazole, flutriafol,
fenpropimorph, and prochloaz, and a multi-site-inhibitor, for
example mancozeb and chlorothalonil, or other commercial fungicides
to provide control of any plant fungal pathogen.
##STR00002##
[0025] As used herein, the compound of Formula I is
5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one.
The compound of Formula I provides control of a variety of
pathogens in economically important crops including, but not
limited to, the causal agent of leaf blotch in wheat, Septoria
tritici (SEPTTR).
[0026] As used herein, epoxiconazole is the common name for
(2RS,3SR)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,-
2,4-triazole and possesses the following structure:
##STR00003##
[0027] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Epoxiconazole provides broad
spectrum control, with preventive and curative action, of diseases
caused by Ascomycetes, Basidiomycetes and Deuteromycetes in
bananas, cereals, coffee, rice and sugar beet.
[0028] As used herein, cyproconazole is the common name for
(2RS,3RS;2RS,3SR)-2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1--
yl)butan-2-ol and possesses the following structure:
##STR00004##
[0029] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Cyproconazole provides control of
Septoria, rust, powdery mildew, Rhynchosporium, Cercospora and
Ramularia in cereals and sugar beet; and rust, Mycena, Sclerotinia
and Rhizoctonia in coffee and turf.
[0030] As used herein, metconazole is the common name for
(1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-y-
lmethyl)cyclopentanol and possesses the following structure:
##STR00005##
[0031] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Metconazole provides control of a
wide range of foliar diseases on cereals and other crops, and is
particularly effective against Fusarium, Septoria and rust diseases
on cereals.
[0032] As used herein, myclobutanil is the common name for
.alpha.-butyl-.alpha.-(4-chlorophenyl)-1H-1,2,4-triazole-1-propanenitrile
and possesses the following structure:
##STR00006##
[0033] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Myclobutanil provides control of
Ascomycetes, Fungi Imperfecti and Basidiomycetes on a wide variety
of crops.
[0034] As used herein, propiconazole is the common name for
(.+-.)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2-
,4-triazole and possesses the following structure:
##STR00007##
[0035] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Propiconazole provides control of
a broad range of diseases on a variety of crops. For example, on
cereals it controls diseases caused by Cochliobolus sativus,
Erysiphe graminis, Leptosphaeria nodorum, Puccinia spp.,
Pyrenophora teres, Pyrenophora tritici-repentis, Rhynchosporium
secalis and Septoria spp, and in bananas it controls diseases
caused by Mycosphaerella musicola and Mycosphaerella fijiensis var.
difformis. Other uses are in turf, against Sclerotinia homoeocarpa,
Rhizoctonia solani, Puccinia spp. and Erysiphe graminis; in rice,
against Rhizoctonia solani, Helminthosporium oryzae and dirty
panicle complex; in coffee, against Hemileia vastatrix; in peanuts,
against Cercospora spp.; in stone fruit, against Monilinia spp.,
Podosphaera spp., Sphaerotheca spp. and Tranzschelia spp.; and in
maize, against Helminthosporium spp.
[0036] As used herein, prothioconazole is the common name
2-[(2RS)-2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2H-1-
,2,4-triazole-3(4H)-thione and possesses the following
structure:
##STR00008##
[0037] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Prothioconazole provides control
of diseases such as eyespot (Pseudocercosporella herpotrichoides),
Fusarium ear blight (Fusarium spp., Microdochium nivale), leaf
blotch diseases (Septoria tritici, Leptosphaeria nodorum,
Pyrenophora spp., Rhynchosporium secalis, etc.), rust (Puccinia
spp.) and powdery mildew (Blumeria graminis), by foliar
application, in wheat, barley and other crops.
[0038] As used herein, picoxystrobin is the common name for methyl
(E)-3-methoxy-2-[2-(6-trifluoromethyl-2-pyridyloxymethyl)phenyl]acrylate
and possesses the following structure:
##STR00009##
[0039] Its fungicidal activity is described in The e-Pesticide
Manual, Version 5.2, 2011. Exemplary uses of picoxystrobin include,
but are not limited to, broad-spectrum disease control in cereals,
including Mycosphaerella graminicola, Phaeosphaeria nodorum,
Puccinia recondita (brown rust), Helminthosporium tritici-repentis
(tan spot) and Blumeria graminis f.sp. tritici
(strobilurin-sensitive powdery mildew) in wheat; Helminthosporium
teres (net blotch), Rhynchosporium secalis, Puccinia hordei (brown
rust) and Erysiphe graminis f.sp. hordei (strobilurin-sensitive
powdery mildew) in barley; Puccinia coronata and Helminthosporium
avenae in oats; and Puccinia recondita and Rhynchosporium secalis
in rye.
[0040] As used herein, trifloxystrobin is the common name for
methyl
(.alpha.E)-.alpha.-(methoxyimino)-2-[[[[(1E)-1-[3-(trifluoromethyl)phenyl-
]ethylidene]amino]oxy]methyl]-benzeneacetate and possesses the
following structure:
##STR00010##
[0041] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Trifloxystrobin provides
broad-spectrum control of a variety of fungal pathogens on a wide
variety of fruits, vegetables, and crops.
[0042] As used herein, azoxystrobin is the common name for methyl
(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate
and possesses the following structure:
##STR00011##
[0043] Its fungicidal activity is exemplified in The e-Pesticide
Manual, Version 5.2, 2011. Exemplary uses of azoxystrobin include,
but are not limited to, control of the following pathogens:
Erysiphe graminis, Puccinia spp., Leptosphaeria nodorum, Septoria
tritici and Pyrenophora teres on temperate cereals; Pyricularia
oryzae and Rhizoctonia solani on rice; Plasmopara viticola and
Uncinula necator on vines; Sphaerotheca fuliginea and
Pseudoperonospora cubensis on cucurbitaceae; Phytophthora infestans
and Alternaria solani on potato and tomato; Mycosphaerella
arachidis, Rhizoctonia solani and Sclerotium rolfsii on peanut;
Monilinia spp. and Cladosporium carpophilum on peach; Pythium spp.
and Rhizoctonia solani on turf; Mycosphaerella spp. on banana;
Cladosporium caryigenum on pecan; Elsinoe fawcettii, Colletotrichum
spp. and Guignardia citricarpa on citrus; Colletotrichum spp. and
Hemileia vastatrix on coffee.
[0044] As used herein, fluoxastrobin is the common name for
(E)-{2-[6-(2-chlorophenoxy)-5-fluoropyrimidin-4-yloxy]phenyl}(5,6-dihydro-
-1,4,2-dioxazin-3-yl)methanone O-methyloxime and possesses the
following structure:
##STR00012##
[0045] Its fungicidal activity is exemplified in The e-Pesticide
Manual, Version 5.2, 2011. Exemplary uses of fluoxastrobin include,
but are not limited to, use as a foliar spray in cereals for
control of Septoria leaf spot diseases (Septoria tritici and
Leptosphaeria nodorum), rusts of wheat and barley (Puccinia
recondita, P. striiformis, P. hordei), Helminthosporium diseases
like Pyrenophora teres (net blotch of barley) and Pyrenophora
tritici-repentis (tan spot).
[0046] As used herein, boscalid is the common name for
2-chloro-N-(4'-chloro[1,1'-biphenyl]-2-yl)-3-pyridinecarboxamide
and possesses the following structure:
##STR00013##
[0047] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Boscalid provides control of
powdery mildew, Alternaria spp., Botrytis spp., Sclerotinia spp.,
Mycosphaerella spp. and Monilia spp. on grapes, turf, and a range
of fruit, vegetables and ornamentals.
[0048] As used herein, isopyrazam is the common name for a mixture
of the 2 syn and 2 anti isomers of
3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9RS)-1,2,3,4-tetrahydro-9-isoprop-
yl-1,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide and
3-(difluoromethyl)-1-methyl-N-[(1RS,4SR,9SR)-1,2,3,4-tetrahydro-9-isoprop-
yl-1,4-methanonaphthalen-5-yl]pyrazole-4-carboxamide, respectively,
and possesses the following structures:
##STR00014##
[0049] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Isopyrazam provides control of
Septoria tritici and rusts in wheat, and Ramularia in barley.
[0050] As used herein, fluxapyroxad is the common name for
3-(difluoromethyl)-1-methyl-N-(3',4',5'-trifluorobiphenyl-2-yl)pyrazole-4-
-carboxamide and possesses the following structure:
##STR00015##
[0051] Its fungicidal activity is exemplified in Agrow Intelligence
(https://www.agra-net.net/agra/agrow/databases/agrow-intelligence/).
Exemplary uses of fluxapyroxad include, but are not limited to, the
control of plant pathogens, such as Helminthosporium teres (net
blotch), Rhynchosporium secalis (leaf scald), Puccinia hordei
(brown rust), and Erysiphe graminis f.sp. hordei (powdery mildew)
in a range of crops, such as barley, maize, and soybeans.
[0052] As used herein, penthiopyrad is the common name for
N-[2-(1,3-dimethylbutyl)-3-thienyl]-1-methyl-3-(trifluoromethyl)-1H-pyraz-
ole-4-carboxamide and possesses the following structure:
##STR00016##
[0053] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Penthiopyrad provides control of
rust and Rhizoctonia diseases, as well as grey mold, powdery mildew
and apple scab.
[0054] As used herein, benzovindiflupyr is the common name for
N-[(1RS,4SR)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthal-
en-5-yl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide and
possesses the following structure:
##STR00017##
[0055] Its fungicidal activity is exemplified in Agrow Intelligence
(https://www.agra-net.net/agra/agrow/databases/agrow-intelligence/).
Exemplary uses of benzovindiflupyr include, but are not limited to,
controlling a variety of pathogens such as Botrytis spp., Erysiphe
spp., Rhizoctonia spp., Septoria spp., Phytophthora spp., Pythium
spp., Phakopsora pachyrhizi, and Puccinia recondita, in a range of
crops including vines, cereals, soybeans, cotton, and fruit and
vegetable crops.
[0056] As used herein, fluquinconazole is the common name for
3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)-
-one and possesses the following structure:
##STR00018##
[0057] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Fluquinconazole provides control
of a wide range of Ascomycetes, Deuteromycetes and Basidiomycetes.
For example, foliar application provides control of Leptosphaeria
nodorum, Septoria tritici, Puccinia spp., Ustilago nuda, Tilletia
caries, Tilletia controversa, Urocystis occulta, Pyrenophora teres,
and Pyrenophora graminea in cereals; Cercospora spp., Microsphaera
diffusa, and Phakopsora pachyrhizi in soybeans; Venturia spp., and
Podosphaera leucotricha in pome fruit; and Uncinula necator in
vines.
[0058] As used herein, difenoconazole is the common name for
1-[[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl]met-
hyl]-1H-1,2,4-triazole and possesses the following structure:
##STR00019##
[0059] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Difenoconazole provides
broad-spectrum fungicidal control, with preventative and curative
action, of diseases caused by Ascomycetes, Basidiomycetes and
Deuteromycetes.
[0060] As used herein, pyraclostrobin is the common name for methyl
N-[2-[[[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy]methyl]phenyl]-N-methoxyca-
rbamate and possesses the following structure:
##STR00020##
[0061] Its fungicidal activity is exemplified in The e-Pesticide
Manual, Version 5.2, 2011. Exemplary uses of pyraclostrobin
include, but are not limited to, the control of major plant
pathogens, such as Septoria tritici, Puccinia spp., Drechslera
tritici-repentis and Pyrenophora teres in cereals.
[0062] As used herein, fluopyram is the common name for
N-[2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl]-2-(trifluoromethyl)-
benzamide and possesses the following structure:
##STR00021##
[0063] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Fluopyram provides control of grey
mold, powdery mildew and sclerotinia and monilinia diseases in a
variety of fruits, vegetables and field crops.
[0064] As used herein, flutriafol is the common name for
(RS)-2,4'-difluoro-a-(1H-1,2,4-triazol-1-ylmethyl)benzhydryl
alcohol and possesses the following structure:
##STR00022##
[0065] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Flutriafol provides control of a
broad spectrum of leaf and ear diseases, including but not limited
to, Erysiphe graminis, Rhynchosporium secalis, Septoria spp.,
Puccinia spp., Helminthosporium teres and Helminthosporium
tritici-repentis in cereals.
[0066] As used herein, kresoxim-methyl is the common name for
methyl (E)-methoxyimino[2-(o-tolyloxymethyl)phenyl]acetate and
possesses the following structure:
##STR00023##
[0067] Its fungicidal activity is exemplified in The e-Pesticide
Manual, Version 5.2, 2011. Exemplary uses of kresoxim-methyl
include, but are not limited to, the control of scab in apples and
pears (Venturia spp.); powdery mildew on apples (Podosphaera
leucotricha), vines (Uncinula necator), cucurbits (Sphaerotheca
fuliginea) and sugar beet (Erysiphe betae); mildew (Erysiphe
graminis), scald (Rhynchosporium secalis), net blotch (Pyrenophora
teres) and glume blotch (Septoria nodorum) on cereals; and mildew
(Leveillula taurica, Erysiphe spp., Alternaria spp.) on
vegetables.
[0068] As used herein, chlorothalonil is the common name
tetrachloroisophthal-onitrile and possesses the following
structure:
##STR00024##
[0069] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Chlorothalonil provides control of
many fungal diseases in a wide range of crops, including pome
fruit, stone fruit, almonds, citrus fruit, bush and cane fruit,
cranberries, strawberries, pawpaws, bananas, mangoes, coconut
palms, oil palms, rubber, pepper, vines, hops, vegetables,
cucurbits, tobacco, coffee, tea, rice, soybeans, peanuts, potatoes,
sugar beet, cotton, maize, omamentals, mushrooms, and turf.
[0070] As used herein, mancozeb is the common name for
[[2-[(dithiocarboxy)amino]ethyl]carbamodithioato(2-)-.kappa.S,.kappa.S]ma-
nganese mixture with
[[2-[(dithiocarboxy)amino]ethyl]carbamodithioato(2-)-.kappa.S,.kappa.S]zi-
nc and possesses the following structure:
##STR00025##
[0071] Its fungicidal activity is described in The Pesticide
Manual, Fifteenth Edition, 2009. Mancozeb provides control of a
wide range of fungal pathogens on a variety of fruits, vegetables
and field crops.
[0072] In the compositions described herein, the concentration
ratio of the compound of Formula I at which the fungicidal effect
is synergistic with the other fungicides against SEPTTR in
protectant and curative applications lies within the range of about
1:250 and about 787:1. In one embodiment, the concentration ratio
of the compound of Formula I at which the fungicidal effect is
synergistic with the other fungicides in protectant applications
lies within the range of about 1:272 and about 787:1. In another
embodiment, the concentration ratio of the compound of Formula I at
which the fungicidal effect is synergistic with the other
fungicides in curative applications lies within the range of about
1:250 and about 120:1.
[0073] In the compositions described herein, the concentration
ratio of the compound of Formula I at which the fungicidal effect
is synergistic with the SBIs against SEPTTR in protectant and
curative applications lies within the range of about 1:27 and about
787:1. In one embodiment, the concentration ratio of the compound
of Formula I at which the fungicidal effect is synergistic with the
SBIs against SEPTTR in protectant applications lies within the
range of about 1:4 and about 787:1. In another embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with the SBIs against SEPTTR in
curative applications lies within the range of about 1:27 and about
120:1. In some embodiments, the concentration ratio of the compound
of Formula I at which the fungicidal effect is synergistic with
epoxiconazole against SEPTTR in protectant and curative
applications lies within the range of about 3.6:1 and about 20:1.
In one embodiment, the concentration ratio of the compound of
Formula I at which the fungicidal effect is synergistic with
epoxiconazole against SEPTTR in protectant applications is about
20:1, and in another embodiment, the concentration ratio of the
compound of Formula I at which the fungicidal effect is synergistic
with epoxiconazole against SEPTTR in curative applications is about
3.6:1. In some embodiments, the concentration ratio of the compound
of Formula I at which the fungicidal effect is synergistic with
cyproconazole against SEPTTR in protectant and curative
applications lies within the range of about 1:3 and about 4.5:1. In
one embodiment, the concentration ratio of the compound of Formula
I at which the fungicidal effect is synergistic with cyproconazole
against SEPTTR in protectant applications is about 4.5:1, and in
another embodiment, the concentration ratio of the compound of
Formula I at which the fungicidal effect is synergistic with
cyproconazole against SEPTTR in curative applications is about 1:3.
In some embodiments, the concentration ratio of the compound of
Formula I at which the fungicidal effect is synergistic with
metconazole against SEPTTR in protectant and curative applications
lies within the range of about 2.2:1 and about 30:1. In one
embodiment, the concentration ratio of the compound of Formula I at
which the fungicidal effect is synergistic with metconazole against
SEPTTR in protectant applications is about 30:1, and in another
embodiment, the concentration ratio of the compound of Formula I at
which the fungicidal effect is synergistic with metconazole against
SEPTTR in curative applications is about 2.2:1. In some
embodiments, the concentration ratio of the compound of Formula I
at which the fungicidal effect is synergistic with myclobutanil
against SEPTTR in protectant and curative applications lies within
the range of about 1:27 and about 1:4. In one embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with the myclobutanil against
SEPTTR in protectant applications is about 1:4, and in another
embodiment, the concentration ratio of the compound of Formula I at
which the fungicidal effect is synergistic with myclobutanil
against SEPTTR in curative applications is about 1:27. In some
embodiments, the concentration ratio of the compound of Formula I
at which the fungicidal effect is synergistic with propiconazole
against SEPTTR in protectant and curative applications lies within
the range of about 1:2.1 and about 30:1. In one embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with propiconazole against SEPTTR
in protectant applications is about 30:1, and in another
embodiment, the concentration ratio of the compound of Formula I at
which the fungicidal effect is synergistic with propiconazole
against SEPTTR in curative applications is about 1:2.1. In some
embodiments, the concentration ratio of the compound of Formula I
at which the fungicidal effect is synergistic with prothioconazole
against SEPTTR in protectant and curative applications lies within
the range of about 1:21.6 and about 2:1. In one embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with prothioconazole against
SEPTTR in protectant applications is about 2:1, and in another
embodiment, the concentration ratio of the compound of Formula I at
which the fungicidal effect is synergistic with prothioconazole
against SEPTTR in curative applications is about 1:21.6. In some
embodiments, the concentration ratio of the compound of Formula I
at which the fungicidal effect is synergistic with fluquinconazole
against SEPTTR in protectant and curative applications lies within
the range of about 1:1.3 and about 170:1. In one embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with the fluquinconazole against
SEPTTR in protectant applications is about 170:1, and in another
embodiment, the concentration ratio of the compound of Formula I at
which the fungicidal effect is synergistic with fluquinconazole
against SEPTTR in curative applications is about 1:1.3. In some
embodiments, the concentration ratio of the compound of Formula I
at which the fungicidal effect is synergistic with difenoconazole
against SEPTTR in protectant and curative applications lies within
the range of about 120:1 and about 787:1. In one embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with difenoconazole against SEPTTR
in protectant applications is about 787:1, and in another
embodiment, the concentration ratio of the compound of Formula I at
which the fungicidal effect is synergistic with difenoconazole
against SEPTTR in curative applications is about 120:1. In some
embodiments, the concentration ratio of the compound of Formula I
at which the fungicidal effect is synergistic with flutriafol
against SEPTTR in protectant and curative applications lies within
the range of about 1:20.6 and about 5.1:1. In one embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with flutriafol against SEPTTR in
protectant applications is about 5.1:1, and in another embodiment,
the concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with flutriafol against SEPTTR in
curative applications is about 1:20.6.
[0074] In the compositions described herein, the concentration
ratio of the compound of Formula I at which the fungicidal effect
is synergistic with the strobilurins against SEPTTR in protectant
and curative applications lies within the range of about 1:250 and
about 42:1. In one embodiment, the concentration ratio of the
compound of Formula I at which the fungicidal effect is synergistic
with the strobilurins against SEPTTR in protectant applications
lies within the range of about 1:21.2 and about 42:1. In another
embodiment, the concentration ratio of the compound of Formula I at
which the fungicidal effect is synergistic with the strobilurins
against SEPTTR in curative applications lies within the range of
about 1:250 and about 20:1. In some embodiments, the concentration
ratio of the compound of Formula I at which the fungicidal effect
is synergistic with picoxystrobin against SEPTTR in protectant and
curative applications lies within the range of about 1:30 and about
1:2.6. In one embodiment, the concentration ratio of the compound
of Formula I at which the fungicidal effect is synergistic with
picoxystrobin against SEPTTR in protectant applications is about
1:2.6, and in another embodiment, the concentration ratio of the
compound of Formula I at which the fungicidal effect is synergistic
with picoxystrobin against SEPTTR in curative applications lies is
about 1:30. In some embodiments, the concentration ratio of the
compound of Formula I at which the fungicidal effect is synergistic
with trifloxystrobin against SEPTTR in protectant and curative
applications lies within the range of about 1:9.7 and about 4:1. In
one embodiment, the concentration ratio of the compound of Formula
I at which the fungicidal effect is synergistic with
trifloxystrobin against SEPTTR in protectant applications is about
4:1, and in another embodiment, the concentration ratio of the
compound of Formula I at which the fungicidal effect is synergistic
with trifloxystrobin against SEPTTR in curative applications is
about 1:9.7. In some embodiments, the concentration ratio of the
compound of Formula I at which the fungicidal effect is synergistic
with azoxystrobin against SEPTTR in protectant and curative
applications lies within the range of about 1:4.6 and about 2:1. In
one embodiment, the concentration ratio of the compound of Formula
I at which the fungicidal effect is synergistic with azoxystrobin
against SEPTTR in protectant applications is about 2:1, and in
another embodiment, the concentration ratio of the compound of
Formula I at which the fungicidal effect is synergistic with
azoxystrobin against SEPTTR in curative applications is about
1:4.6. In some embodiments, the concentration ratio of the compound
of Formula I at which the fungicidal effect is synergistic with
fluoxastrobin against SEPTTR in protectant and curative
applications lies within the range of about 1:1.6 and about 7:1. In
one embodiment, the concentration ratio of the compound of Formula
I at which the fungicidal effect is synergistic with fluoxastrobin
against SEPTTR in protectant applications is about 7:1, and in
another embodiment, the concentration ratio of the compound of
Formula I at which the fungicidal effect is synergistic with
fluoxastrobin against SEPTTR in curative applications is about
1:1.6. In some embodiments, the concentration ratio of the compound
of Formula I at which the fungicidal effect is synergistic with
pyraclostrobin against SEPTTR in protectant and curative
applications lies within the range of about 20:1 and about 42:1. In
one embodiment, the concentration ratio of the compound of Formula
I at which the fungicidal effect is synergistic with pyraclostrobin
against SEPTTR in protectant applications is about 42:1, and in
another embodiment, the concentration ratio of the compound of
Formula I at which the fungicidal effect is synergistic with
pyraclostrobin against SEPTTR in curative applications is about
20:1. In some embodiments, the concentration ratio of the compound
of Formula I at which the fungicidal effect is synergistic with
kresoxim-methyl against SEPTTR in protectant and curative
applications lies within the range of about 1:250 and about 1:21.2.
In one embodiment, the concentration ratio of the compound of
Formula I at which the fungicidal effect is synergistic with
kresoxim-methyl against SEPTTR in protectant applications is about
1:21.2, and in another embodiment, the concentration ratio of the
compound of Formula I at which the fungicidal effect is synergistic
with kresoxim-methyl against SEPTTR in curative applications is
about 1:250.
[0075] In the compositions described herein, the concentration
ratio of the compound of Formula I at which the fungicidal effect
is synergistic with the SDHIs against SEPTTR in protectant and
curative applications lies within the range of about 1:28 and about
8:1. In one embodiment, the concentration ratio of the compound of
Formula I at which the fungicidal effect is synergistic with the
SDHIs against SEPTTR in protectant applications lies within the
range of about 1:3.6 and about 8:1. In another embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with the SDHIs against SEPTTR in
curative applications lies within the range of about 1:28 and about
6.3:1. In some embodiments, the concentration ratio of the compound
of Formula I at which the fungicidal effect is synergistic with
boscalid against SEPTTR in protectant and curative applications
lies within the range of about 1:13.2 and about 1:1.3. In one
embodiment, the concentration ratio of the compound of Formula I at
which the fungicidal effect is synergistic with boscalid against
SEPTTR in protectant applications is about 1:1.3, and in another
embodiment, the concentration ratio of the compound of Formula I at
which the fungicidal effect is synergistic with boscalid against
SEPTTR in curative applications is about 1:13.2. In some
embodiments, the concentration ratio of the compound of Formula I
at which the fungicidal effect is synergistic with isopyrazam
against SEPTTR in protectant and curative applications lies within
the range of about 1:1.3 and about 1:1. In one embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with isopyrazam against SEPTTR in
protectant applications is about 1:1.3, and in another embodiment,
the concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with isopyrazam against SEPTTR in
curative applications is about 1:1. In some embodiments, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with fluxapyroxad against SEPTTR
in protectant and curative applications lies within the range of
about 4.4:1 and about 6.3:1. In one embodiment, the concentration
ratio of the compound of Formula I at which the fungicidal effect
is synergistic with fluxapyroxad against SEPTTR in protectant
applications is about 4.4:1, and in another embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with fluxapyroxad against SEPTTR
in curative applications is about 6.3:1. In some embodiments, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with penthiopyrad against SEPTTR
in protectant and curative applications lies within the range of
about 1:4.3 and about 1:1.9. In one embodiment, the concentration
ratio of the compound of Formula I at which the fungicidal effect
is synergistic with penthiopyrad against SEPTTR in protectant
applications is about 1:1.9, and in another embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with penthiopyrad against SEPTTR
in curative applications is about 1:4.3. In some embodiments, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with benzovindiflupyr against
SEPTTR in protectant and curative applications lies within the
range of about 1:3 and about 7.9:1. In one embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with benzovindiflupyr against
SEPTTR in protectant applications is about 7.9:1, and in another
embodiment, the concentration ratio of the compound of Formula I at
which the fungicidal effect is synergistic with benzovindiflupyr
against SEPTTR in curative applications is about 1:3. In some
embodiments, the concentration ratio of the compound of Formula I
at which the fungicidal effect is synergistic with fluopyram
against SEPTTR in protectant and curative applications lies within
the range of about 1:27.6 and about 1:3.6. In one embodiment, the
concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with fluopyram against SEPTTR in
protectant applications is about 1:3.6, and in another embodiment,
the concentration ratio of the compound of Formula I at which the
fungicidal effect is synergistic with fluopyram against SEPTTR in
curative applications is about 1:27.6.
[0076] In the compositions described herein, the concentration
ratio of the compound of Formula I at which the fungicidal effect
is synergistic with the multi-site inhibitors against SEPTTR in
protectant applications lies within the range of about 1:272 and
about 1:219. In some embodiments, the concentration ratio of the
compound of Formula I at which the fungicidal effect is synergistic
with chlorothalonil against SEPTTR in protectant applications is
about 1:219. In some embodiments, the concentration ratio of the
compound of Formula I at which the fungicidal effect is synergistic
with mancozeb against SEPTTR in protectant applications is about
1:272.
[0077] The rate at which the synergistic composition is applied
will depend upon the particular type of fungus to be controlled,
the degree of control required and the timing and method of
application. In general, the compositions described herein can be
applied at an application rate of between about 40 grams per
hectare (g/ha) and about 2600 g/ha based on the total amount of
active ingredients in the composition.
[0078] The compositions comprising the compound of Formula I and an
SBI can be applied at an application rate of between about 40 g/ha
and about 600 g/ha based on the total amount of active ingredients
in the composition. Epoxiconazole is applied at a rate of between
about 50 g/ha and about 250 g/ha, and the compound of Formula I is
applied at a rate between about 15 g/ha and about 100 g/ha.
Cyproconazole is applied at a rate of between about 50 g/ha and
about 250 g/ha, and the compound of Formula I is applied at a rate
between about 15 g/ha and about 100 g/ha. Metconazole is applied at
a rate of between about 50 g/ha and about 250 g/ha, and the
compound of Formula I is applied at a rate between about 15 g/ha
and about 100 g/ha. Myclobutanil is applied at a rate of between
about 30 g/ha and about 150 g/ha, and the compound of Formula I is
applied at a rate between about 15 g/ha and about 100 g/ha.
Propiconazole is applied at a rate of between about 50 g/ha and
about 250 g/ha, and the compound of Formula I is applied at a rate
between about 15 g/ha and about 100 g/ha. Prothioconazole is
applied at a rate of between about 50 g/ha and about 250 g/ha, and
the compound of Formula I is applied at a rate between about 15
g/ha and about 100 g/ha. Fluquinconazole is applied at a rate of
between about 25 g/ha and about 500 g/ha and the compound of
Formula I is applied at a rate between about 15 g/ha and about 100
g/ha. Difenoconazole is applied at a rate of between about 30 g/ha
and about 125 g/ha, and the compound of Formula I is applied at a
rate between about 15 g/ha and about 100 g/ha. Flutriafol is
applied at a rate of between about 60 g/ha and about 200 g/ha, and
the compound of Formula I is applied at a rate between about 15
g/ha and about 100 g/ha.
[0079] The compositions comprising the compound of Formula I and a
strobilurin can be applied at an application rate of between about
65 g/ha and about 650 g/ha based on the total amount of active
ingredients in the composition. Picoxystrobin is applied at a rate
of between about 50 g/ha and about 250 g/ha, and the compound of
Formula I is applied at a rate between about 15 g/ha and about 100
g/ha. Trifloxystrobin is applied at a rate of between about 50 g/ha
and about 550 g/ha, and the compound of Formula I is applied at a
rate between about 15 g/ha and about 100 g/ha. Azoxystrobin is
applied at a rate of between about 100 g/ha and about 375 g/ha, and
the compound of Formula I is applied at a rate between about 15
g/ha and about 100 g/ha. Fluoxastrobin is applied at a rate of
between about 75 g/ha and about 200 g/ha, and the compound of
Formula I is applied at a rate between about 15 g/ha and about 100
g/ha. Pyraclostrobin is applied at a rate of between about 50 g/ha
and about 250 g/ha, and the compound of Formula I is applied at a
rate between about 15 g/ha and about 100 g/ha. Kresoxim-methyl is
applied at a rate of between about 50 g/ha and about 250 g/ha and
the compound of Formula I is applied at a rate between about 15
g/ha and about 100 g/ha.
[0080] The compositions comprising the compound of Formula I and an
SDHI can be applied at an application rate of between about 40 g/ha
and about 725 g/ha based on the total amount of active ingredients
in the composition. Boscalid is applied at a rate of between about
100 g/ha and about 625 g/ha, and the compound of Formula I is
applied at a rate between about 15 g/ha and about 100 g/ha.
Isopyrazam is applied at a rate of between about 25 g/ha and about
300 g/ha, and the compound of Formula I is applied at a rate
between about 15 g/ha and about 100 g/ha. Fluxapyroxad is applied
at a rate of between about 45 g/ha and about 200 g/ha, and the
compound of Formula I is applied at a rate between about 15 g/ha
and about 100 g/ha. Penthiopyrad is applied at a rate of between
about 100 g/ha and about 400 g/ha, and the compound of Formula I is
applied at a rate between about 15 g/ha and about 100 g/ha.
Benzovindiflupyr is applied at a rate of between about 25 g/ha and
about 300 g/ha, and the compound of Formula I is applied at a rate
between about 15 g/ha and about 100 g/ha. Fluopyram is applied at a
rate of between about 30 g/ha and about 250 g/ha, and the compound
of Formula I is applied at a rate between about 15 g/ha and about
100 g/ha.
[0081] The compositions comprising the compound of Formula I and a
multi-site inhibitor can be applied at an application rate of
between about 1015 g/ha and about 2600 g/ha based on the total
amount of active ingredients in the composition. Chlorothalonil is
applied at a rate of between about 1000 g/ha and about 2500 g/ha,
and the compound of Formula I is applied at a rate between about 15
g/ha and about 100 g/ha. Mancozeb is applied at a rate of between
about 1500 g/ha and about 2000 g/ha, and the compound of Formula I
is applied at a rate between about 15 g/ha and about 100 g/ha.
[0082] The components of the synergistic mixture described herein
can be applied either separately or as part of a multipart
fungicidal system.
[0083] The synergistic mixture of the present disclosure can be
applied in conjunction with one or more other fungicides to control
a wider variety of undesirable diseases. When used in conjunction
with other fungicide(s), the presently claimed compounds may be
formulated with the other fungicide(s), tank mixed with the other
fungicide(s) or applied sequentially with the other fungicide(s).
Such other fungicides may include
2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol,
8-hydroxyquinoline sulfate, ametoctradin, amisulbrom, antimycin,
Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus
subtilis, Bacillus subtilis strain QST713, benalaxyl, benomyl,
benthiavalicarb-isopropyl, benzylaminobenzene-sulfonate (BABS)
salt, bicarbonates, biphenyl, bismerthiazol, bitertanol, bixafen,
blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole,
bupirimate, calcium polysulfide, captafol, captan, carbendazim,
carboxin, carpropamid, carvone, chlazafenone, chloroneb,
chlorothalonil, chlozolinate, Coniothyrium minitans, copper
hydroxide, copper octanoate, copper oxychloride, copper sulfate,
copper sulfate (tribasic), cuprous oxide, cyazofamid, cyflufenamid,
cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, diammonium
ethylenebis-(dithiocarbamate), dichlofluanid, dichlorophen,
diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole,
difenzoquat ion, diflumetorim, dimethomorph, dimoxystrobin,
diniconazole, diniconazole-M, dinobuton, dinocap, diphenylamine,
dithianon, dodemorph, dodemorph acetate, dodine, dodine free base,
edifenphos, enestrobin, enestroburin, epoxiconazole, ethaboxam,
ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol,
fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil,
fenpropidin, fenpropimorph, fenpyrazamine, fentin, fentin acetate,
fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil,
flumorph, fluopicolide, fluopyram, fluoroimide, fluoxastrobin,
fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil,
flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl,
fosetyl-aluminum, fuberidazole, furalaxyl, furametpyr, guazatine,
guazatine acetates, GY-81, hexachlorobenzene, hexaconazole,
hymexazol, imazalil, imazalil sulfate, imibenconazole,
iminoctadine, iminoctadine triacetate, iminoctadine
tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone,
iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam,
isotianil, kasugamycin, kasugamycin hydrochloride hydrate,
kresoxium-methyl, laminarin, mancopper, mancozeb, mandipropamid,
maneb, mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercuric
chloride, mercuric oxide, mercurous chloride, metalaxyl,
metalaxyl-M, metam, metam-ammonium, metam-potassium, metam-sodium,
metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate,
metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil,
nabam, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oleic
acid (fatty acids), orysastrobin, oxadixyl, oxine-copper,
oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole,
pencycuron, penflufen, pentachlorophenol, pentachlorophenyl
laurate, penthiopyrad, phenylmercury acetate, phosphonic acid,
phthalide, picoxystrobin, polyoxin B, polyoxins, polyoxorim,
potassium bicarbonate, potassium hydroxyquinoline sulfate,
probenazole, prochloraz, procymidone, propamocarb, propamocarb
hydrochloride, propiconazole, propineb, proquinazid,
prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin,
pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil,
pyriofenone, pyroquilon, quinoclamine, quinoxyfen, quintozene,
Reynoutria sachalinensis extract, sedaxane, silthiofam,
simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodium
pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, tar oils,
tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole,
thifluzamide, thiophanate-methyl, thiram, tiadinil,
tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,
triazoxide, tricyclazole, tridemorph, trifloxystrobin,
triflumizole, triforine, triticonazole, validamycin, valifenalate,
valiphenal, vinclozolin, zineb, ziram, zoxamide, Candida oleophila,
Fusarium oxysporum, Gliocladium spp., Phlebiopsis gigantea,
Streptomyces griseoviridis, Trichoderma spp.,
(RS)--N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide,
1,2-dichloropropane, 1,3-dichloro-1,1,3,3-tetrafluoroacetone
hydrate, 1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitropropane,
2-(2-heptadecyl-2-imidazolin-1-yl)ethanol,
2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide,
2-methoxyethylmercury acetate, 2-methoxyethylmercury chloride,
2-methoxyethylmercury silicate,
3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop-1-enyl)phenyl
thiocyanateme, ampropylfos, anilazine, azithiram, barium
polysulfide, Bayer 32394, benodanil, benquinox, bentaluron,
benzamacril, benzamacril-isobutyl, benzamorf, binapacryl,
bis(methylmercury) sulfate, bis(tributyltin) oxide, buthiobate,
cadmium calcium copper zinc chromate sulfate, carbamorph, CECA,
chlobenthiazone, chloraniformethan, chlorfenazole, chlorquinox,
climbazole, copper bis(3-phenylsalicylate), copper zinc chromate,
cufraneb, cupric hydrazinium sulfate, cuprobam, cyclafuramid,
cypendazole, cyprofuram, decafentin, dichlone, dichlozoline,
diclobutrazol, dimethirimol, dinocton, dinosulfon, dinoterbon,
dipyrithione, ditalimfos, dodicin, drazoxolon, EBP, ESBP,
etaconazole, etem, ethirim, fenaminosulf, fenapanil, fenitropan,
fluotrimazole, furcarbanil, furconazole, furconazole-cis,
furmecyclox, furophanate, glyodine, griseofulvin, halacrinate,
Hercules 3944, hexylthiofos, ICIA0858, isopamphos, isovaledione,
mebenil, mecarbinzid, metazoxolon, methfuroxam, methylmercury
dicyandiamide, metsulfovax, milneb, mucochloric anhydride,
myclozolin, N-3,5-dichlorophenyl-succinimide,
N-3-nitrophenylitaconimide, natamycin,
N-ethylmercurio-4-toluenesulfonanilide, nickel
bis(dimethyldithiocarbamate), OCH, phenylmercury
dimethyldithiocarbamate, phenylmercury nitrate, phosdiphen,
prothiocarb, prothiocarb hydrochloride, pyracarbolid, pyridinitril,
pyroxychlor, pyroxyfur, quinacetol, quinacetol sulfate, quinazamid,
quinconazole, rabenzazole, salicylanilide, SSF-109, sultropen,
tecoram, thiadifluor, thicyofen, thiochlorfenphim, thiophanate,
thioquinox, tioxymid, triamiphos, triarimol, triazbutil,
trichlamide, urbacid, zarilamid, and any combinations thereof.
[0084] The compositions of the present disclosure are preferably
applied in the form of a formulation comprising a composition of
(a) a compound of Formula I and (b) at least one fungicide selected
from the group consisting of pyraclostrobin, fluoxastrobin,
azoxystrobin, trifloxystrobin, picoxystrobin, kresoxim-methyl,
fluxapyroxad, benzovindiflupyr, penthiopyrad, isopyrazam, boscalid,
fluopyram, prothioconazole, epoxiconazole, cyproconazole,
myclobutanil, metconazole, difenoconazole, propiconazole,
fluquinconazole, flutriafol, mancozeb and chlorothalonil, together
with a phytologically acceptable carrier.
[0085] Concentrated formulations can be dispersed in water, or
another liquid, for application, or formulations can be dust-like
or granular, which can then be applied without further treatment.
The formulations are prepared according to procedures which are
conventional in the agricultural chemical art, but which are novel
and important because of the presence therein of a synergistic
composition.
[0086] The formulations that are applied most often are aqueous
suspensions or emulsions. Either such water-soluble,
water-suspendable, or emulsifiable formulations are solids, usually
known as wettable powders, or liquids, usually known as
emulsifiable concentrates, aqueous suspensions, or suspension
concentrates. The present disclosure contemplates all vehicles by
which the synergistic compositions can be formulated for delivery
and use as a fungicide.
[0087] As will be readily appreciated, any material to which these
synergistic compositions can be added may be used, provided they
yield the desired utility without significant interference with the
activity of these synergistic compositions as antifungal
agents.
[0088] Wettable powders, which may be compacted to form
water-dispersible granules, comprise an intimate mixture of the
synergistic composition, a carrier and agriculturally acceptable
surfactants. The concentration of the synergistic composition in
the wettable powder is usually from about 10% to about 90% by
weight, more preferably about 25% to about 75% by weight, based on
the total weight of the formulation. In the preparation of wettable
powder formulations, the synergistic composition can be compounded
with any of the finely divided solids, 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 is ground or mixed with the synergistic composition
in a volatile organic solvent. Effective surfactants, comprising
from about 0.5% to about 10% by weight of the wettable powder,
include sulfonated lignins, naphthalenesulfonates,
alkylbenzenesulfonates, alkyl sulfates, and non-ionic surfactants,
such as ethylene oxide adducts of alkyl phenols.
[0089] Emulsifiable concentrates of the synergistic composition
comprise a convenient concentration, such as from about 10% to
about 50% by weight, in a suitable liquid, based on the total
weight of the emulsifiable concentrate formulation. The components
of the synergistic compositions, jointly or separately, are
dissolved in a 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.
[0090] 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 solubilized 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 or sulfated polyglycol
ethers and appropriate salts of phosphated polyglycol ether.
[0091] Representative organic liquids which can be employed in
preparing the emulsifiable concentrates of the present disclosure
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 of fatty
glycols and glycol derivatives such as the n-butyl ether, ethyl
ether or methyl ether of diethylene glycol, and the methyl ether of
triethylene glycol. Mixtures of two or more organic liquids are
also often suitably employed in the preparation of the emulsifiable
concentrate. The preferred organic liquids are xylene, and propyl
benzene fractions, with xylene being most preferred. The
surface-active dispersing agents are usually employed in liquid
formulations and in the amount of from 0.1 to 20 percent by weight
of the combined weight of the dispersing agent with the synergistic
compositions. The formulations can also contain other compatible
additives, for example, plant growth regulators and other
biologically active compounds used in agriculture.
[0092] Aqueous suspensions comprise suspensions of one or more
water-insoluble compounds, dispersed in an aqueous vehicle at a
concentration in the range from about 5% to about 70% by weight,
based on the total weight of the aqueous suspension formulation.
Suspensions are prepared by finely grinding the components of the
synergistic combination either together or separately, and
vigorously mixing the ground material into a vehicle comprised of
water and surfactants chosen from the same types discussed above.
Other ingredients, 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.
[0093] The synergistic composition may also be applied as a
granular formulation, which is particularly useful for applications
to the soil. Granular formulations usually contain from about 0.5%
to about 10% by weight of the compounds, based on the total weight
of the granular formulation, dispersed in a carrier which consists
entirely or in large part of coarsely divided attapulgite,
bentonite, diatomite, clay or a similar inexpensive substance. Such
formulations are usually prepared by dissolving the synergistic
composition 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. Such formulations may
also be prepared by making a dough or paste of the carrier and the
synergistic composition, and crushing and drying to obtain the
desired granular particle.
[0094] Dusts containing the synergistic composition are prepared
simply by intimately mixing the synergistic composition in powdered
form with a suitable dusty agricultural carrier, such as, for
example, kaolin clay, ground volcanic rock, and the like. Dusts can
suitably contain from about 1% to about 10% by weight of the
synergistic composition/carrier combination.
[0095] The formulations may contain agriculturally acceptable
adjuvant surfactants to enhance deposition, wetting and penetration
of the synergistic composition onto the target crop and organism.
These adjuvant surfactants may optionally be employed as a
component of the formulation or as a tank mix. The amount of
adjuvant surfactant will vary from 0.01 percent to 1.0 percent
volume per volume (v/v) based on a spray-volume of water,
preferably 0.05 to 0.5 percent. Suitable adjuvant surfactants
include ethoxylated nonyl phenols, ethoxylated synthetic or natural
alcohols, salts of the esters or sulfosuccinic acids, ethoxylated
organosilicones, ethoxylated fatty amines and blends of surfactants
with mineral or vegetable oils.
[0096] The formulations may optionally include combinations that
can comprise at least 1% by weight of one or more of the
synergistic compositions with another pesticidal compound. Such
additional pesticidal compounds may be fungicides, insecticides,
nematocides, miticides, arthropodicides, bactericides or
combinations thereof that are compatible with the synergistic
compositions of the present disclosure in the medium selected for
application, and not antagonistic to the activity of the present
compounds. Accordingly, in such embodiments the other pesticidal
compound is employed as a supplemental toxicant for the same or for
a different pesticidal use. The pesticidal compound and the
synergistic composition can generally be mixed together in a weight
ratio of from 1:100 to 100:1.
[0097] The present disclosure includes within its scope methods for
the control or prevention of fungal attack. These methods comprise
applying to the locus of the fungus, or to a locus in which the
infestation is to be prevented (for example applying to wheat or
barley plants), a fungicidally effective amount of the synergistic
composition. The synergistic composition is suitable for treatment
of various plants at fungicidal levels, while exhibiting low
phytotoxicity. The synergistic composition is useful in a
protectant or eradicant fashion. The synergistic composition is
applied by any of a variety of known techniques, either as the
synergistic composition or as a formulation comprising the
synergistic composition. For example, the synergistic compositions
may be applied to the roots, seeds or foliage of plants for the
control of various fungi, without damaging the commercial value of
the plants. The synergistic composition is applied in the form of
any of the generally used formulation types, for example, as
solutions, dusts, wettable powders, flowable concentrates, or
emulsifiable concentrates. These materials are conveniently applied
in various known fashions.
[0098] The synergistic composition has been found to have
significant fungicidal effect, particularly for agricultural use.
The synergistic composition is particularly effective for use with
agricultural crops and horticultural plants, or with wood, paint,
leather or carpet backing.
[0099] In particular, the synergistic composition is effective in
controlling a variety of undesirable fungi that infect useful plant
crops. The synergistic composition may be used against a variety of
Ascomycete and Basidiomycete fungi, including for example the
following representative fungi species: wheat brown rust (Puccinia
triticina; Synonym Puccinia recondita f. sp. tritici; Bayer code
PUCCRT); stripe rust of wheat (Puccinia striiformis; Bayer code
PUCCST); leaf blotch of wheat (Mycosphaerella graminicola;
anamorph: Septoria tritici; Bayer code SEPTTR); glume blotch of
wheat (Leptosphaeria nodorum; Bayer code LEPTNO; anamorph:
Stagonospora nodorum); spot blotch of barley (Cochliobolus sativum;
Bayer code COCHSA; anamorph: Helminthosporium sativum); leaf spot
of sugar beets (Cercospora beticola; Bayer code CERCBE); leaf spot
of peanut (Mycosphaerella arachidis; Bayer code MYCOAR; anamorph:
Cercospora arachidicola); cucumber anthracnose (Glomerella
lagenarium; anamorph: Colletotrichum lagenarium; Bayer code COLLLA)
and black sigatoka disease of banana (Mycosphaerella fijiensis;
BAYER code MYCOFI). It will be understood by those in the art that
the efficacy of the synergistic compositions for one or more of the
foregoing fungi establishes the general utility of the synergistic
compositions as fungicides.
[0100] The synergistic compositions have a broad range of efficacy
as a fungicide. The exact amount of the synergistic composition to
be applied is dependent not only on the relative amounts of the
components, 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
synergistic composition. Thus, formulations containing the
synergistic composition may not be equally effective at similar
concentrations or against the same fungal species.
[0101] The synergistic compositions 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 the synergistic composition that
kills or inhibits the plant disease for which control is desired,
but is not significantly toxic to the plant. The exact
concentration of synergistic composition required varies with the
fungal disease to be controlled, the type of formulation employed,
the method of application, the particular plant species, climate
conditions, and the like.
[0102] The present compositions can be applied to fungi or their
locus by the use of conventional ground sprayers, granule
applicators, and by other conventional means known to those skilled
in the art.
[0103] The following examples are provided for illustrative
purposes and should not be construed as limitations to the
disclosure.
EXAMPLES
[0104] Evaluation of Curative and Protectant Activity of Fungicide
Mixtures vs. Leaf Blotch of Wheat (Mycosphaerella graminicola;
anamorph: Septoria tritici Bayer code: SEPTTR):
[0105] Wheat plants (variety Yuma) were grown from seed in a
greenhouse in plastic pots with a surface area of 27.5 square
centimeters (cm.sup.2) containing 50% mineral soil/50% soil-less
Metro mix, with 8-12 seedlings per pot. The plants were employed
for testing when the first leaf was fully emerged, which typically
took 7 to 8 days after planting. Test plants were inoculated with
an aqueous spore suspension of Septoria tritici either 3 days prior
to (3-day curative test) or 1 day after fungicide treatments (1-day
protectant test). After inoculation the plants were kept in 100%
relative humidity (one day in a dark dew chamber followed by two
days in a lighted mist chamber) to permit spores to germinate and
infect the leaf. The plants were then transferred to a greenhouse
for disease to develop.
[0106] Treatments consisted of fungicide compounds pyraclostrobin,
fluoxastrobin, azoxystrobin, trifloxystrobin, picoxystrobin,
kresoxim-methyl, fluxapyroxad, benzovindiflupyr, penthiopyrad,
isopyrazam, boscalid, fluopyram, prothioconazole, epoxiconazole,
cyproconazole, myclobutanil, metconazole, difenoconazole,
propiconazole, fluquinconazole, flutriafol, mancozeb and
chlorothalonil, either using individually or as two-way mixtures
with the compound of Formula I.
[0107] Detailed dose-responses of each fungicide in 1-day
protectant (1DP) and 3-day curative (3DC) SEPTTR whole plant assays
were performed using high-volume spray applications, and EC.sub.50
values were calculated using JMP Pro 9.0. With the exception of
isopyrazam, fluxapyroxad and penthiopyrad, compounds were tested as
technical grade material formulated in acetone, and spray solutions
contained 10% acetone and 100 parts per million (ppm) Triton X-100.
Commercially available EC formulations Seguris Flexi and Imtrex
were used for isopyrazam and fluxapyroxad respectively, and the SC
Fontelis for penthiopyrad. 10% EC and SC formulations of Compound I
were also used to determine their EC.sub.50 values. Compound I was
mixed with each fungicide based on EC.sub.50 values for protectant
and curative activities, respectively. The EC formulation for
Compound I was mixed with isopyrazam and fluxapyroxad, and the SC
with penthiopyrad; the remaining mixtures involved technical
materials for both Compound I and its mixing partners.
[0108] Ten milliliter (mL) fungicide solutions were applied onto 8
pots of plants using an automated booth sprayer, which utilized two
6218-1/4 JAUPM spray nozzles operating at 20 pounds per square inch
(psi) set at opposing angles to cover both leaf surfaces. All
sprayed plants were allowed to air dry prior to further handling.
Control plants were sprayed in the same manner with the solvent
blank.
[0109] When disease fully developed on the control plants,
infection levels were assessed on treated plants visually and
scored on a scale of 0 to 100 percent. Percentage of disease
control was then calculated using the ratio of disease on treated
plants relative to control plants.
[0110] Colby's equation was used to determine the fungicidal
effects expected from the mixtures. (See Colby, S. R. Calculation
of the synergistic and antagonistic response of herbicide
combinations. Weeds 1967, 15, 20-22.)
[0111] The following equation was used to calculate the expected
activity of mixtures containing two active ingredients, A and
B:
Expected=A+B-(A.times.B/100)
[0112] A=observed efficacy of active component A at the same
concentration as used in the mixture;
[0113] B=observed efficacy of active component B at the same
concentration as used in the mixture.
[0114] Representative synergistic interactions are presented in
Tables 1 and 2.
TABLE-US-00001 TABLE 1 Synergistic Interactions of the Compound of
Formula I and Other Fungicides in 1-Day Protectant (1 DP) Septoria
tritici (SEPTTR) Tests. Rates SEPTTR* Synergism Composition (ppm)*
Observed* Expected* Factor* Cmpd. I + 1.18 + 0.06 89 70 1.26
Epoxiconazole Cmpd. I + 1.18 + 0.26 91 81 1.13 Cyproconazole Cmpd.
I + 1.18 + 0.04 86 71 1.21 Metconazole Cmpd. I + 1.18 + 4.81 95 70
1.35 Myclobutanil Cmpd. I + 1.18 + 0.04 96 67 1.43 Propiconazole
Cmpd. I + 1.18 + 0.64 90 70 1.29 Prothioconazole Cmpd. I + 1.18 +
3.08 85 75 1.14 Picoxystrobin Cmpd. I + 1.18 + 0.3 84 73 1.15
Trifloxystrobin Cmpd. I + 1.18 + 0.64 94 67 1.39 Azoxystrobin Cmpd.
I + 1.18 + 0.17 89 74 1.20 Fluoxastrobin Cmpd. I + 1.18 + 1.56 79
67 1.18 Boscalid Cmpd. I.sup.a + 8.41 + 10.9 100 91 1.10 Isopyrazam
Cmpd. I.sup.a + 8.41 + 1.92 100 42 2.41 Fluxapyroxad Cmpd. I.sup.b
+ 2.56 + 4.98 100 59 1.68 Penthiopyrad Cmpd. I + 1.18 + 0.15 49 32
1.50 Benzovindiflupyr Cmpd. I + 1.18 + 0.007 39 31 1.25
Fluquinconazole Cmpd. I + 1.18 + 0.0015 46 33 1.38 Difenoconazole
Cmpd. I + 1.18 + 0.028 46 40 1.16 Pyraclostrobin Cmpd. I + 1.18 +
4.19 43 34 1.26 Fluopyram Cmpd. I + 1.18 + 0.23 30 27 1.10
Flutriafol Cmpd. I + 1.18 + 25.sup. 51 35 1.45 Kresoxim-methyl
Cmpd. I + 1.18 + 258 41 31 1.30 Chlorothalonil Cmpd. I + 1.18 + 321
42 31 1.34 Mancozeb *SEPTTR = Leaf Blotch of Wheat; Septoria
tritici *DC Observed = Observed disease control at the test rates
*DC Expected = Disease control expected as predicted by the Colby
equation *ppm = Parts per million *Synergism factor = % DC
Observed/% DC Expected *Cmpd I.sup.a = An EC formulation of
compound I was used *Cmpd I.sup.b = An SC formulation of compound I
was used
TABLE-US-00002 TABLE 2 Synergistic Interactions of the Compound of
Formula I and Other Fungicides in 3-Day Curative (3 DC) Septoria
tritici (SEPTTR) Tests. Rates SEPTTR* Synergism Composition (ppm)*
Observed* Expected* Factor* Cmpd. I + 0.18 + 0.05 99 77 1.29
Epoxiconazole Cmpd. I + 0.18 + 0.54 98 84 1.17 Cyproconazole Cmpd.
I + 0.18 + 0.08 93 67 1.38 Metconazole Cmpd. I + 0.18 + 4.86 94 62
1.51 Myclobutanil Cmpd. I + 0.18 + 0.38 77 52 1.48 Propiconazole
Cmpd. I + 0.18 + 3.89 58 50 1.18 Prothioconazole Cmpd. I + 0.18 +
5.4 68 92 0.73 Picoxystrobin Cmpd. I + 0.18 + 1.74 69 95 0.73
Trifloxystrobin Cmpd. I + 0.18 + 0.83 61 79 0.77 Azoxystrobin Cmpd.
I + 0.18 + 0.29 51 78 0.65 Fluoxastrobin Cmpd. I + 0.18 + 2.37 43
93 0.46 Boscalid Cmpd. I.sup.a + 2.27 + 2.19 74 64 1.15 Isopyrazam
Cmpd. I.sup.a + 2.27 + 0.36 71 53 1.33 Fluxapyroxad Cmpd. I.sup.b +
0.2 + 0.86 77 61 1.25 Penthiopyrad Cmpd. I + 0.18 + 0.54 72 56 1.29
Benzovindiflupyr Cmpd. I + 0.18 + 0.24 27 64 0.42 Fluquinconazole
Cmpd. I + 0.18 + 0.0015 21 62 0.33 Difenoconazole Cmpd. I + 0.18 +
0.009 71 59 1.20 Pyraclostrobin Cmpd. I + 0.18 + 4.96 78 51 1.54
Fluopyram Cmpd. I + 0.18 + 3.7 81 64 1.27 Flutriafol Cmpd. I + 0.18
+ 45.sup. 23 42 0.54 Kresoxim-methyl *SEPTTR = Leaf Blotch of
Wheat; Septoria tritici *DC Observed = Observed disease control at
the test rates *DC Expected = Disease control expected as predicted
by the Colby equation *ppm = Parts per million *Synergism factor =
% DC Observed/% DC Expected *Cmpd I.sup.a = An EC formulation of
compound I was used *Cmpd I.sup.b = An SC formulation of compound I
was used
* * * * *
References