NZ738966B2 - Synergistic fungicidal mixtures and compositions for fungal control - Google Patents

Abstract

The present invention relates to a synergistic fungicidal mixture comprising a fungicidally effective amount of the compound of Formula I: 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2-(1H)-one, and at least one (i) fungicidal multi-site inhibitor or (ii) strobilurin fungicide, that provides synergistic control of selected fungi. This invention also relates to synergistic fungal composition containing this mixture. des synergistic control of selected fungi. This invention also relates to synergistic fungal composition containing this mixture.

Description

SYNERGISTIC IDAL MIXTURES AND COMPOSITIONS FOR FUNGAL CONTROL CROSS REFERENCE TO D APPLICATIONS This application is a onal of New Zealand patent application no. 722436, the entire disclosure of which is incorporated herein by nce. [0001A] This application claims the t of U.S. Provisional Patent Application Serial Nos. ,616, 61/922,630, and 61/922,640, all filed December 31,2013, which are expressly orated by reference herein.

FIELD 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 e 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, nconazole, 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 Fungicides are compounds, of natural or synthetic origin, which act to t 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 y 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.

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 ides.

Consequently, research is being conducted to produce fungicides and combinations of ides that are safer, that have better performance, that require lower dosages, that are easier to use, and that cost less.

Synergism occurs when the activity of two or more compounds exceeds the activities of the compounds when used alone.

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, es caused by fungi of the classes Ascomycetes and Basidz‘omycetes. In addition, the synergistic compositions have ed efficacy against the cele 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.

According to an exemplary embodiment of the present disclosure, a synergistic fungicidal mixture is provided including a fungicidally effective amount of the compound of a I, and at least one fungicidal multi—site inhibitor.

According to another exemplary embodiment of the present sure, a synergistic fungicidal mixture is provided including a fungicidally effective amount of the compound of Formula I, and at least additional fungicide in which the at least one additional fungicide is a idal multi-site inhibitor.

According to yet another exemplary embodiment of the present disclosure, a synergistic, fungicidal ition is provided including a fungicidally effective amount of the mixture and an agriculturally acceptable adjuvant or carrier.

In certain embodiments, the multi-site tor and/or the at least one additional fungicide is selected from the group consisting of thalonil and mancozeb.

In certain embodiments, the multi-site inhibitor and/or the at least one additional fungicide is chlorothalonil.

In certain embodiments, the multi-site tor and/or the at least one additional fungicide is mancozeb.

In n ments, the concentration ratio of the Compound of Formula I to chlorothalonil is about 1:219.

In certain embodiments, the concentration ratio of the Compound of Formula I to mancozeb is about 1:272.

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 lrz'tici), Wheat Brown Rust nia triticina), Stripe Rust (Puccinia striiformis f.

[Annotation] cassarm None set by cassarm [Annotation] m MigrationNone set by cassarm ation] cassarm Unmarked set by cassarm Sp. tritici), Scab of Apple (Venturia inaequalis), Blister Smut of Maize (Usrilago mag/dis), Powdery Mildew of ine (Uncinula necator), Barley scald (Rhynchosporium secalis), Blast of Rice (Magnaporthe grisea), Rust of Soybean (Phakopsora hizi), Glume Blotch of Wheat (Leptospkaeria nodorum), Powdery Mildew of Wheat (Blumeria graminisf. sp.tritici), Powdery Mildew of Barley (Blumeria graminisf Sp. hordei), Powdery Mildew of Cucurbits (Erysipke cichoracearum), Anthracnose of Cucurbits (Glomerella Zagenarium), Leaf Spot of Beet (Cercospora beticola), Early Blight of Tomato (Alternaria salami), and Net Blotch of Barley (Pyrenophora teres).

In certain embodiments, the e provides control of a fungal pathogen and the fungal pathogen is Leaf Blotch of Wheat (Mycosphaerella gramz'm'cola; anamorph: Septoria lritici).

According to yet r exemplary embodiment of the present disclosure, a synergistic fungicidal mixture is provided including a fungicidally ive amount of the compound of Formula I, and at least one lurin fungicide.

According to still yet 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 ide in which the at least one additional fungicide is a lurin fungicide.

According to still yet another exemplary embodiment of the present sure, a synergistic, fungicidal composition is provided including a fungicidally effective amount of the e and an agriculturally acceptable adjuvant or carrier.

In certain embodiments, the strobilurin fungicide and/or the at least one additional fungicide is selected from the group consisting of pyraclostrobin, fluoxastrobin, azoxystrobin, trifloxystrobin, picoxystrobin, and kresoxim-methyl.

In certain embodiments, the strobilurin fungicide and/or the at least one onal fungicide is pyraclostrobin.

In certain embodiments, the strobilurin fungicide and/or the at least one additional fungicide is azoxystrobin.

In certain embodiments, the concentration ratio of the Compound of Formula I to picoxystrobin is between about 1:30 and about 122.6.

In certain embodiments, the concentration ratio of the Compound of Formula I to trifloxystrobin is between about 1:9.7 and about 4:1.

In n embodiments, the concentration ratio of the nd of Formula I to afiystrobin is between about 1:4.6 and about 2:1.

[Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] m Unmarked set by cassarm In certain embodiments, the concentration ratio of the Compound of Formula I to trobin is between about 111.6 and about 7:1.

In certain embodiments, the concentration ratio of the Compound of Formula I to im-methyl is between about 1:250 and about 1:212.

In certain embodiments, the mixture es l of a fungal pathogen and the fungal pathogen is one of Leaf Blotch of Wheat (Mycosphaerella gramim'cola; anamorph: Septoria tritici), Wheat Brown Rust nia triticina), Stripe Rust (Puccinia Striz'formis f.

Sp. triticz'), Scab of Apple (Venturia inaequalz‘s), Blister Smut of Maize (Usz‘ilago maydz’s), Powdery Mildew of Grapevine (Uncinula necator), Barley scald (Rhynchosporium secalis), Blast of Rice (Magnaporthe grisea), Rust of Soybean (Phakopsom pachyrhz'zz'), Glume Blotch of Wheat (Leptosphaeria nodorum), Powdery Mildew of Wheat (Blumeria graminisf. sp.trz‘tz'ci), Powdery Mildew of Barley (Blumerz'a gramz'nz'sf Sp. hordez'), Powdery Mildew of Cucurbits (Erjysiphe cichoracearum), Anthracnose of its (Glomerella rium), Leaf Spot of Beet (Cercospora beticola), Early Blight of Tomato (Alternaria solani), and Net Blotch of Barley (Pyrenophora teres).

In certain embodiments, the mixture provides control of a fungal pathogen and the fungal pathogen is Leaf Blotch of Wheat (Mycosphaerella graminicola; ph: Septoria tritici).

DETAILED DESCRIPTION The present disclosure concerns a synergistic fungicidal mixture comprising a fungicidally ive amount of (a) a compound of Formula I and (b) at least one fungicide selected from the group consisting of a lurin, for example pyraclostrobin, fluoxastrobin, azoxystrobin, trifloxystrobin, picoxystrobin, and kresoxim-methyl, a succinate ogenase-inhibitor, for example fluxapyroxad, benzovindiflupyr, opyrad, isopyrazam, bixafen, boscalid, penflufen, and fluopyram, an ergosterol biosynthesis—inhibitor, for example prothioconazole, epoxiconazole, cyproconazole, myclobutanil, prochloraz, metconazole, difenoconazole, tebuconazole, tetraconazole, fenbuconazole, propiconazole, fluquinconazole, zole, flutriafol, fenpropimorph, and oaz, and a multi—site- inhibitor, for example mancozeb and chlorothalonil, or other commercial fungicides to provide control of any plant fungal pathogen.

[Annotation] m None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm F O\\S/©/ fl/ ’ \\ 0 HN [T] 0 Formulal [003 1] As used herein, the compound of a I is 5-fluoro-4—imino—3 -methyl-l- tosyl-3,4—dihydropyrimidin-2(lH)—one. The compound of Formula I provides l of a variety of pathogens in economically important crops including, but not limited to, the causal agent of leaf blotch in wheat, Septoria triticz' (SEPTTR).

As used , epoxiconazole is the common name for SR)-l—[3—(2- chlorophenyl)—2,3-epoxy(4-fluorophenyl)propyl]- lH—l,2,4-triazole and possesses the following structure: 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.

As used herein, cyproconazole is the common name for (2RS,3RS;2RS,3SR)-2— orophenyl)—3 -cyclopropyl- l —( lH— l ,2,4-triazol- l tan-2—ol and possesses the following structure: [Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by m 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 s and sugar beet; and rust, Mycena, Sclerotinia and Rhizoctom'a in coffee and turf.

As used herein, metconazole is the common name for (lRS,5RS; lRS,5SR)—5- orobenzyl)-2,2—dimethyl—l-(1H—1,2,4—triazol—l—ylmethyl)cyclopentanol and possesses the following structure: Its fungicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Metconazole provides l of a wide range of foliar diseases on cereals and other crops, and is particularly effective t Fusarium, Septoria and rust es on cereals.

As used herein, myclobutanil is the common name for a—butyl—a—(4— phenyl)— lH—l,2,4-triazole-l—propanenitrile and possesses the following structure: H3C N Its fungicidal activity is described in The Pesticide Manual, Fifteenth n, 2009. Myclobutanil provides control of Ascomycetes, Fungi Imperfecti and Basidiomycetes on a wide variety of crops.

As used herein, propiconazole is the common name for (::)—1-[2—(2,4— dichlorophenyl)—4-propyl—l,3-dioxolanylmethyl]-lH—l,2,4-triazole and possesses the following structure: [Annotation] m None set by cassarm [Annotation] cassarm MigrationNone set by m [Annotation] cassarm Unmarked set by m Its idal ty is described in The Pesticide Manual, Fifteenth Edition, 2009. Propiconazole es control of a broad range of diseases on a variety of crops. For example, on cereals it controls diseases caused by Cochliobolus salivus, 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 Mycosphaerellafijiensis var. diflormis. Other uses are in turf, against tinia homoeocarpa, tonia salami, Puccinia spp. and Erysiphe graminis; in rice, against Rhizoctonia solani, Helminthosporium oryzae and dirty panicle complex; in coffee, against Hemileia vastatrix; in peanuts, against pora spp.; in stone fruit, against Monilz'nia spp., Podosphaera spp., Sphaerotheca spp. and Tranzschelia spp.; and in maize, against Helminthosporium spp.

As used herein, prothioconazole is the common name 2-[(2RS)(l— cyclopropyl)-3 -(2-chlorophenyl)—2-hydroxypropyl]-2H— l ,2,4—triazole—3 (4H)-thione and possesses the following structure: N\\’_\/¢SNH Its fungicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Prothioconazole provides control of diseases such as t (Pseudocercosporella herpotrichoides), Fusarium ear blight (Fusarium spp., Microdochium nivale), leaf blotch diseases (Septoria tritici, phaeria nodorum, Pyrenophora spp., Rhynchosporz’um secalis, etc.), rust (Puccinia spp.) and powdery mildew (Blumeria graminis), by foliar application, in wheat, barley and other crops.

As used herein, picoxystrobin is the common name for methyl (E)—3—methoxy- 2—[2—(6-trifluoromethylpyridyloxymethyl)phenyl]acrylate and possesses the following structure: [Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm Its fungicidal activity is described in The e-Pesticide Manual, Version 5.2, 2011. ary uses of picoxystrobin include, but are not d to, broad—spectrum disease control in cereals, including Mycosphaerella gramim'cola, Phaeospkaeria nodoram, Puccinia recondita (brown rust), Helminthosporium tritici-repentis (tan spot) and Blumeria gramim's f.sp. triticz' (strobilurin-sensitive powdery mildew) in wheat; Helminthosporium teres (net blotch), Rhynchosporium secalz's, Puccinia hordei (brown rust) and Erysz'phe gramim's f.sp. hordez' (strobilurin-sensitive powdery mildew) in barley; ia coronata and Helminthosporium avenae in oats; and Puccinia recondita and Rhynchosporium secalis in rye.

As used , trifloxystrobin is the common name for methyl (am-ot- (methoxyimino)—2-[[[[( IE) [3 —(1:rifluoromethyl)phenyl] ethylidene] amino]oxy]methyl] - benzeneacetate and ses the following structure: Its fungicidal activity is described in The Pesticide , Fifteenth Edition, 2009. Trifloxystrobin provides broad-spectrum control of a variety of fungal pathogens on a wide variety of fruits, vegetables, and crops.

AS used herein, azoxystrobin is the common name for methyl (E)-2—{2-[6-(2- cyanophenoxy)pyrimidin-4—yloxy]phenyl}—3 —methoxyacrylate and ses the following Its fungicidal activity is exemplified in The e—Pesticia’e Manual, Version 5.2, 2011. Exemplary uses of azoxystrobin include, but are not limited to, control of the following pathogens: Erysiphe graminis, Puccinia spp., phaeria m, Septoria tritici and Pyrenophora teres on temperate cereals; Pyricularia oryzae and Rhizoctonia solani on rice; Piasmopara viticola and Uncinala necator on vines; Sphaerothecafuliginea and [Annotation] cassarm None set by cassarm ation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm Pseudoperonospora is on cucurbitaceae; Phylophthora infestans and Alternaria solam‘ on potato and tomato; Mycosphaerella arachidis, Rhizoctonia solam' and Sclerotiam i on peanut; Monilim'a spp. and Cladosporium carpophilam on peach; Pythium spp. and Rhizoctonia solam' on turf; Mycosphaerella spp. on banana; Cladosporiam caryigenum on pecan; Elsinoe'fawcettii, Colletotricham spp. and Guignardz‘a citricarpa on citrus; Colletotrz’chum spp. and Hemileia vastatrz'x on coffee.

As used herein, fluoxastrobin is the common name for (IE)— {2—[6—(2— chlorophenoxy)—5-fluoropyrimidinyloxy]phenyl} (5 ydro-l ,4,2-dioxazin-3 - yl)methanone 0—methyloxime and possesses the following structure: 0 ,0 F o —N _ N_ o \ N H3C—O/ N—// Its fungicidal ty is exemplified in The e—Pestz'cia’e 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 Leptosphaerz'a nodorum), rusts of wheat and barley nia recondita, P. Striiformis, P. hordei), thosporium diseases like Pyrenophora teres (net blotch of barley) and Pyrenophora tritici-repentz‘s (tan spot).

As used herein, boscalid is the common name for ro—N—(4’—chloro[1, 1 ’— biphenyl]y1)pyridinecarboxamide and possesses the following structure: o / Cl N Its fungicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Boscalid provides control ofpowdery mildew, Alternaria spp., is spp., Sclerotz'nz’a spp., Mycosphaerella spp. and 'a spp. on grapes, turf, and a range of fruit, vegetables and ornamentals.

[Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm As used herein, isopyrazam is the common name for a mixture of the 2 syn and 2 anti s of 3-(difluoromethyl)-l—methyl-N—[(lRS,4SR,9RS)-l,2,3,4-tetrahydro isopropyl—l,4-methanonaphthalen—5 -yl]pyrazole-4—carboxamide and 3-(difluoromethyl)-lmethyl-N —[( lRS,4SR,9SR)— l ,2,3 ,4-tetrahydroisopropyl-1,4-methanonaphthalen-5— yl]pyrazole—4—carboxamide, tively, and ses the following structures: F H30 N N‘N \h.‘ I syn anti Its fungicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Isopyrazam provides control of Septoria tritici and rusts in wheat, and Ramalaria in barley.

As used herein, fluxapyroxad is the common name for 3—(difluoromethyl)—l— methyl—N—(3’,4’,5’—trifluorobipheny1-2—yl)pyrazole—4-carboxamide and possesses the ing structure: 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 Helminthosporiam teres (net blotch), Rhynchosporium secalz's (leaf scald), Puccinia hordez' (brown rust), and Erysz'phe graminis f.sp. hordei ry mildew) in a range of crops, such as barley, maize, and As used herein, penthiopyrad is the common name for N—[2—( 1,3— dimethylbutyl)-3 —thienyl]— l -methyl-3 -(trifluoromethyl)— lH—pyrazolecarboxamide and ses the ing structure: [Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by m [Annotation] cassarm Unmarked set by cassarm N\ I CH3 CH3 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.

As used herein, benzovindiflupyr is the common name for N—[(1RS,4SR)—9— (dichloromethylene)- 1,2,3 ,4-tetrahydro-1,4-methanonaphthalen-5—yl]-3 -(difluoromethyl)— 1 — methylpyrazole—4—carboxamide and ses the following structure: CI [H3 CI N \ UN Its fungicidal activity is exemplified in Agrow igence (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 Botrytz's spp., Erysiphe spp., Rhizoctonia spp., Septoria spp., Phytophthora spp., Pythium spp., Phakopsora hizi, and Puccinia recondita, in a range of crops including vines, cereals, soybeans, cotton, and fruit and vegetable crops.

As used herein, fluquinconazole is the common name for 3—(2,4— dichlorophenyl)—6—fluoro-2—(1H—1,2,4—triazol—1—y1)quinazolin—4(3H)—one and possesses the following structure: Mr:/N N CI \\—N/ [Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm Its fungicidal activity is bed in The ide Manual, Fifteenth Edition, 2009. Fluquinconazole provides control of a wide range of Ascomycetes, Deuteromycetes and Basidiomycetes. For example, foliar ation provides control of Leptosphaeria nodorum, Septoria tritici, Puccinia spp., go nuda, Tilletia caries, Tilletia controversa, lis occulta, Pyrenophora teres, and Pyrenophora graminea in s; Cercospora spp., phaera diflusa, and Phakopsora pachyrhizi in soybeans; Venturia spp., and Podosphaera Zeucotricha in pome fruit; and Uncz'nula necator in vines.

As used herein, difenoconazole is the common name for l—[[2—[2—chloro-4—(4— chlorophenoxy)phenyl]methy1-1,3 -dioxolany1]methyl]-1H—1,2,4-triazole and possesses the following structure: 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.

As used herein, pyraclostrobin is the common name for methyl N—[2-[[[l—(4— chlorophenyl)— azol—3-yl]oxy]methy1]pheny1]-N—methoxycarbamate and possesses the following structure: N‘N oawe,CH3 RAD/b Its fungicidal activity is exemplified in The e—Pesticia’e 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.

[Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm As used , fluopyram is the common name for N—[2—[3—chloro—5- (trifluoromethyl)-2—pyridinyl]ethyl]-2—(trifluoromethyl)benzamide and possesses the following structure: CI F F 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, bles and field crops.

As used herein, flutriafol is the common name for ,4’-difluoro-a-(1H— 1,2,4-triazol—1—ylmethyl)benzhydryl alcohol and possesses the following structure: Its fungicidal activity is bed in The Pesticide Manual, Fifteenth Edition, 2009. Flutriafol provides control of a broad spectrum of leaf and ear diseases, ing but not limited to, Erysiphe graminis, Rhynchosporium secalis, Septoria spp., Puccinia spp., Helminthosporium teres and Helminthosporium i—repentis in cereals.

As used herein, kresoxim-methyl is the common name for methyl ()5)— methoxyimino[2—(0—tolyloxymethyl)phenyl]acetate and ses the following structure: Its fungicidal activity is exemplified in The e—Pesticide Manual, n 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 leucolricha), ation] cassarm None set by cassarm [Annotation] m MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm vines (Uncinula necator), cucurbits (Sphaerothecafuliginea) and sugar beet (Erysiphe betae); mildew (Erysiphe graminis), scald (Rhynchosporium secalis), net blotch (Pyrenophora teres) and glume blotch (Seploria nodorum) on cereals; and mildew (Leveillula taurica, Erysiphe spp., Alternaria spp.) on vegetables.

As used herein, Chlorothalonil is the common name tetrachloroisophthal- onitrile and possesses the following structure: CI CI Cl \ Its fungicidal activity is described in The Pesticide , Fifteenth Edition, 2009. Chlorothalonil provides control of many fungal diseases in a wide range of crops, including pome fruit, stone fruit, s, 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, ornamentals, mushrooms, and turf.

As used herein, mancozeb is the common name for [[2— [(dithiocarboxy)amino]ethyl]carbamodithioato(2—)-KS,KS’]manganese mixture with [[2- iocarboxy)amino]ethyl]carbamodithioato(2—)—1 structure: JL H s- -s N/\/ Mn" (Zn) y H Y X:y = 1 : 0.091 Its fungicidal activity is bed in The Pesticide , Fifteenth n, 2009. Mancozeb provides l of a wide range of fungal pathogens on a variety of fruits, vegetables and field crops.

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 1. In one embodiment, the concentration ratio of the compound of Formula I at [Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by m 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 r embodiment, the concentration ratio of the compound of a 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.

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 ations 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 nd of Formula I at which the fungicidal effect is synergistic with the SBIs against SEPTTR in curative ations 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 tant and curative ations 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 tant 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 t 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 ations is about 4.5: 1, and in another embodiment, the concentration ratio of the compound of a I at which the fungicidal effect is synergistic with cyproconazole against SEPTTR in curative applications is about 1:3. In some ments, the concentration ratio of the nd 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 221 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 a I at which the funfidal effect is synergistic with metconazole against SEPTTR in curative applications is [Annotation] cassarm None set by cassarm [Annotation] m MigrationNone set by cassarm ation] m Unmarked set by cassarm about 2.2: 1. In some embodiments, the concentration ratio of the compound of Formula I at which the fungicidal effect is synergistic with utanil 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 r ment, the concentration ratio of the nd of a I at which the fungicidal effect is synergistic with myclobutanil t SEPTTR in curative applications is about 1:27. In some embodiments, the concentration ratio of the nd of Formula I at which the fungicidal effect is synergistic with propiconazole against SEPTTR in protectant and ve ations 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 1:21. 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 ations 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 t 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 121.6. In some embodiments, the concentration ratio of the compound of Formula I at which the fungicidal effect is synergistic with fluquinconazole t SEPTTR in protectant and curative applications lies within the range of about 121.3 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 tant 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 1:13. 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 witfifenoconazole against SEPTTR in protectant applications is about 787:1, and in another [Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm embodiment, the concentration ratio of the compound of a I at which the fungicidal effect is synergistic with difenoconazole against SEPTTR in curative applications is about 120: 1. In some embodiments, the tration ratio of the compound of a I at which the fungicidal effect is synergistic with flutriafol against SEPTTR in protectant and curative applications lies within the range of about 1:206 and about 5. 1: 1. In one ment, 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 1:206.

In the compositions described , the concentration ratio of the compound of Formula I at which the idal effect is synergistic with the strobilurins against SEPTTR in protectant and curative ations lies within the range of about 1:250 and about 42: 1. In one embodiment, the concentration ratio of the compound of FormulaI at which the fungicidal effect is synergistic with the strobilurins against SEPTTR in protectant applications lies within the range of about 121.2 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 ations 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 t SEPTTR in protectant and curative applications lies within the range of about 1:30 and about 12.6. In one embodiment, the concentration ratio of the compound of Formula I at which the fungicidal effect is synergistic with picoxystrobin against SEPTTR in tant applications is about 122.6, and in another embodiment, the concentration ratio of the compound of Formula I at which the fungicidal effect is synergistic with picoxystrobin t 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 nd of Formula I at which the fungicidal effect is synergistic with trifloxystrobin against SEPTTR in protectant applications is about 4: 1, and in another ment, the concentration ratio of the compound of Formula I at which the fungicidal effect is synergistic with ystrobin against SEPTTR in curative applications is about 129.7. In some embodiments, the concentration ratio of the compound of Formula I at which the fungicidal effect is synergistic witfioxystrobin t SEPTTR in protectant and curative applications lies within the ation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm ed set by cassarm range of about 1:46 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 t SEPTTR in protectant applications is about 2: 1, and in another embodiment, the concentration ratio of the nd of Formula I at which the fungicidal effect is synergistic with azoxystrobin against SEPTTR in curative applications is about 1:46. In some ments, the concentration ratio of the compound of Formula I at which the fungicidal effect is synergistic with fluoxastrobin against SEPTTR in protectant and curative ations lies within the range of about 121.6 and about 721. 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 idal effect is synergistic with fluoxastrobin against SEPTTR in curative applications is about 121.6. 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 ostrobin 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 1:212, and in another embodiment, the tration ratio of the compound of Formula I at which the fungicidal effect is istic with kresoxim-methyl against SEPTTR in curative applications is about 1:250.

In the compositions described herein, the tration ratio of the compound of Formula I at which the idal effect is synergistic with the SDHIs against SEPTTR in protectant and ve 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 ations lies within the range of about 13.6 and about 8: 1. In another embodiment, the concentration ratio of the confimd of a I at which the fungicidal effect is synergistic with the SDHIs against ation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm ed set by cassarm 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 a I at which the fungicidal effect is synergistic with boscalid against SEPTTR in protectant and curative applications lies within the range of about 1213.2 and about 121.3. In one embodiment, the concentration ratio of the compound of a I at which the fungicidal effect is istic with boscalid against SEPTTR in protectant applications is about 121.3, 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 1213.2. 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 tration ratio of the compound of Formula I at which the fungicidal effect is synergistic with isopyrazam against SEPTTR in protectant applications is about 1:13, and in another embodiment, the concentration ratio of the compound of Formula I at which the fungicidal effect is istic with isopyrazam against SEPTTR in ve 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 ve 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 nd 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 opyrad against SEPTTR in protectant and ve applications lies within the range of about 124.3 and about 121.9. 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 istic with penthiopyrad against SEPTTR in curative ations is about 1:43. In some embodiments, the concentration ratio of the compound of Formula I at which the fungicidal effect is synergistic with indiflupyr against SEPTTR in protectant and curative applications lies within the range of about 1:3 and about 7.921. In one embodiment, the concentration ratio of the compound of Formula I at which the fungicidal effefi' synergistic with benzovindiflupyr against SEPTTR in protectant applications is [Annotation] m None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by m 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 indiflupyr 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 istic with fluopyram against SEPTTR in protectant and curative applications lies within the range of about 127.6 and about 1:36. In one embodiment, the concentration ratio of the compound of FormulaI at which the fungicidal effect is istic with am against SEPTTR in protectant applications is about 123.6, and in r 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 1227.6.

In the compositions described herein, the concentration ratio of the compound of Formula I at which the fungicidal effect is synergistic with the site inhibitors against SEPTTR in protectant applications lies within the range of about 1:272 and about 1:219. In some ments, 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.

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 l, the compositions described herein can be applied at an ation rate of between about 40 grams per hectare (g/ha) and about 2600 g/ha based on the total amount of active ients in the composition.

The compositions comprising the compound of a 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/hfid about 100 g/ha. Propiconazole is applied at a rate of between about 50 g/ha and [Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm ation] m Unmarked set by cassarm 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 a I is applied at a rate between about 15 g/ha and about 100 g/ha. conazole 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 d at a rate n about 15 g/ha and about 100 g/ha.

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 n 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 nd 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 n 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.

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 a 1 is d at a rate between about 15 g/ha and about 100 g/ha. Isopyrazam is applied at a rate of between about 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. yroxad 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 abofiOO g/ha, and the compound of a I is applied at a rate between about 15 g/ha [Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm and about 100 g/ha. indiflupyr is applied at a rate of between about 25 g/ha and about 300 g/ha, and the compound of Formula I is d 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.

The compositions comprising the nd of Formula I and a 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 nd 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.

The components of the istic mixture described herein can be applied either separately or as part of a multipart fungicidal system.

The synergistic mixture of the present sure 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 tially with the other ide(s). Such other fungicides may include 2— (thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8—hydroxyquinoline sulfate, ametoctradin, amisulbrom, antimycin, Ampelomyces quisqualz's, azaconazole, azoxystrobin, Bacillus subtilis, Bacillus subtilis strain QST713, benalaxyl, benomyl, benthiavalicarb- isopropyl, aminobenzene-sulfonate (BABS) salt, bicarbonates, biphenyl, bismerthiazol, bitertanol, n, 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 e, copper sulfate (tribasic), cuprous oxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, t, debacarb, diammonium ethylenebis-(dithiocarbamate), dichlofluanid, rophen, diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole, difenzoquat ion, diflumetorim, dimethomorph, dimoxystrobin, nazole, diniconazole-M, dinobuton, dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, , dodine free base, edifenphos, enestrobin, enestroburin, epoxiconazole, ethaboxam, ethfiluin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, [Annotation] cassarm None set by cassarm ation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine, fentin, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph, fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, amide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl, fosetyl-aluminum, fuberidazole, xyl, furametpyr, guazatine, guazatine acetates, GY-8l, hexachlorobenzene, hexaconazole, zol, imazalil, il sulfate, imibenconazole, iminoctadine, tadine triacetate, iminoctadine tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isotianil, mycin, mycin hydrochloride hydrate, kresoxium-methyl, laminarin, mancopper, mancozeb, mandipropamid, maneb, xam, mepanipyrim, mepronil, meptyl—dinocap, mercuric chloride, mercuric oxide, mercurous chloride, metalaxyl, xyl—M, metam, metam-ammonium, metam-potassium, 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, boxin, pefurazoate, penconazole, pencycuron, en, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, mercury acetate, phosphonic acid, phthalide, picoxystrobin, polyoxin B, polyoxins, orim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, idone, 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 ylphenoxide, sodium onate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-ZO48, 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, a oleophila, Fusarium oxysporum, Gliocladium spp., Phlebz‘opsz's gigantea, Streptomyces griseovz'rz'dis, Trichoderma spp., —(3,5— dichlorophenyl)—2—(methoxymethyl)-succinimide, 1,2—dichloropropane, l,3—dichloro—l,l,3,3— tetrafluoroacetone hydrate, l-chloro-2,4-dinitronaphthalene, l-chloronitropropane, 2—(2- heptadecy1imidazolin- 1 —yl)ethanol, 2,3 ro—5-pheny1-l ,4-dithi-ine 1, l ,4,4-tetraoxide, 2—methoxyethylmercury acetate, 2—methoxyethylmercury chloride, 2-methoxyethylmercury silifi 3—(4-chlorophenyl)—5-methylrhodanine, 4-(2-nitroprop—l-enyl)phenyl thiocyanateme, [Annotation] cassarm None set by cassarm [Annotation] cassarm ionNone set by cassarm [Annotation] cassarm Unmarked set by cassarm ampropylfos, anilazine, azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox, bentaluron, benzamacril, benzamacril-isobutyl, benzamorf, binapacryl, bis(methylmercury) sulfate, ibutyltin) oxide, buthiobate, cadmium calcium copper zinc chromate e, carbamorph, CECA, chlobenthiazone, chloraniformethan, chlorfenazole, chlorquinox, climbazole, copper bis(3 -phenylsalicylate), copper zinc chromate, cufraneb, cupric hydrazinium sulfate, cuprobam, cyclafuramid, azole, cyprofuram, decafentin, dichlone, dichlozoline, diclobutrazol, dimethirimol, dinocton, dinosulfon, dinoterbon, dipyrithione, mfos, dodicin, drazoxolon, EBP, ESBP, etaconazole, etem, ethirim, fenaminosulf, fenapanil, fenitropan, fluotrimazole, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin, inate, Hercules 3944, hexylthiofos, ICIA0858, isopamphos, isovaledione, mebenil, mecarbinzid, metazoxolon, methfuroxam, methylmercury dicyandiamide, metsulfovax, milneb, loric anhydride, myclozolin, N- chlorophenyl-succinimide, N—3-nitrophenylitaconimide, natamycin, N—ethylmercurio-4— toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), OCH, phenylmercury dimethyldithiocarbamate, mercury nitrate, phosdiphen, prothiocarb, prothiocarb hydrochloride, pyracarbolid, pyridinitril, pyroxychlor, pyroxyfur, quinacetol, quinacetol sulfate, quinazamid, nazole, rabenzazole, salicylanilide, 9, sultropen, tecoram, thiadifluor, thicyofen, thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trichlamide, urbacid, zarilamid, and any ations thereof.

The compositions of the present disclosure are preferably applied in the form of a formulation sing a composition of (a) a compound of Formula I and (b) at least one fungicide selected from the group consisting of ostrobin, fluoxastrobin, azoxystrobin, trifloxystrobin, strobin, kresoxim-methyl, fluxapyroxad, benzovindiflupyr, penthiopyrad, isopyrazam, boscalid, fluopyram, prothioconazole, epoxiconazole, onazole, myclobutanil, metconazole, conazole, propiconazole, fluquinconazole, flutriafol, mancozeb and chlorothalonil, together with a phytologically acceptable carrier.

Concentrated ations can be dispersed in water, or another liquid, for ation, or formulations can be dust-like or granular, which can then be applied without further treatment. The formulations are prepared according to ures which are conventional in the agricultural chemical art, but which are novel and important because of the presence therein of a synergistic composition.

The formulations that are applied most often are aqueous suspensions or emfins. Either such water—soluble, water—suspendable, or emulsifiable formulations are [Annotation] cassarm None set by cassarm [Annotation] m MigrationNone set by cassarm ation] cassarm Unmarked set by cassarm solids, usually known as wettable powders, or liquids, usually known as emulsifiable concentrates, aqueous sions, or suspension concentrates. The t disclosure contemplates all vehicles by which the synergistic itions can be formulated for delivery and use as a fungicide.

As will be readily appreciated, any al to which these synergistic compositions can be added may be used, provided they yield the d utility without significant interference with the activity of these synergistic compositions as antifungal agents.

Wettable powders, which may be compacted to form water—dispersible granules, comprise an intimate mixture of the synergistic composition, a carrier and agriculturally able surfactants. The concentration of the synergistic composition in the wettable powder is usually from about 10% to about 90% by weight, more ably about % 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, , montmorillonite clays, diatomaceous earths, d silicates or the like. In such operations, the finely divided r is ground or mixed with the synergistic composition in a volatile organic solvent. Effective surfactants, sing 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 s of alkyl phenols.

Emulsiflable 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 emulsif1able concentrate ation. The components of the synergistic compositions, jointly or separately, are dissolved in a carrier, which is either a 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 oiling 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.

Emulsifiers which can be advantageously employed herein can be y detfined by those skilled in the art and include various nonionic, anionic, cationic and [Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm amphoteric emulsifiers, or a blend of two or more fiers. Examples of nonionic emulsifiers useful in ing the emulsifiable concentrates include the kylene glycol ethers and condensation products of alkyl and aryl phenols, aliphatic ls, 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.

Representative organic liquids which can be employed in preparing the emulsifiable trates of the present disclosure are the aromatic liquids such as xylene, propyl benzene fractions, or mixed naphthalene fractions, mineral oils, substituted aromatic organic s such as dioctyl phthalate, kerosene, l amides of various fatty acids, particularly the yl 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 fiable concentrate. The preferred organic liquids are xylene, and propyl benzene ons, with xylene being most preferred. The e—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. s 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 s suspension formulation.

Suspensions are prepared by finely grinding the components of the synergistic ation either together or separately, and vigorously mixing the ground al into a e 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.

The synergistic composition may also be applied as a granular formulation, which is particularly useful for applications to the soil. Granular formulations usually n froflout 0.5% to about 10% by weight of the compounds, based on the total weight of the [Annotation] cassarm None set by cassarm ation] cassarm MigrationNone set by cassarm [Annotation] cassarm ed set by m granular formulation, dispersed in a carrier which consists entirely or in large part of coarsely d attapulgite, bentonite, diatomite, clay or a similar inexpensive substance. Such formulations are usually prepared by dissolving the synergistic ition 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 istic composition, and crushing and drying to obtain the d granular particle.

Dusts containing the synergistic composition are ed 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 ly contain from about 1% to about 10% by weight of the synergistic composition/carrier combination.

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 ent 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, lated organosilicones, ethoxylated fatty amines and blends of surfactants with mineral or vegetable oils.

The ations may optionally include combinations that can comprise at least 1% by weight of one or more of the synergistic compositions with another pesticidal nd. Such additional pesticidal compounds may be fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides or combinations thereof that are compatible with the synergistic compositions of the t 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.

The t sure includes within its scope methods for the control or prevention of fungal attack. These methods comprise ng 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 plata a idally effective amount of the synergistic composition. The synergistic ation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm ed set by cassarm composition is suitable for treatment of various plants at fungicidal levels, while exhibiting low phytotoxicity. The synergistic ition 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 sing the synergistic composition. For example, the synergistic compositions may be applied to the roots, seeds or e 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 d in various known fashions.

The synergistic composition has been found to have significant fungicidal effect, particularly for agricultural use. The synergistic composition is ularly effective for use with agricultural crops and horticultural plants, or with wood, paint, leather or carpet backing.

] In particular, the synergistic composition is effective in lling a variety of undesirable fungi that infect useful plant crops. The istic composition may be used against a y ofAscomycete and Basidiomycete fungi, including for example the following entative fungi species: wheat brown rust (Puccinia triticina; Synonym Puccinia reconditaf Sp. tritici; Bayer code PUCCRT); stripe rust of wheat (Puccinia striz'formis; Bayer code PUCCST); leaf blotch of wheat (Mycosphaerella graminicola; anamorph: Septoria triticz’; Bayer code SEPTTR); glume blotch of wheat sphaeria m; 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 dicola); cucumber anthracnose (Giomerella Zagenarz'um; anamorph: Colletotrz'chum Zagenarz’um; Bayer code COLLLA) and black sigatoka disease of banana (Mycosphaerellafijiensis; 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.

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 s to be controlled, and the stage of growth thereof, as well as the part of the plant or othfioduct to be ted with the synergistic composition. Thus, formulations containing [Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by cassarm ation] cassarm Unmarked set by cassarm the synergistic composition may not be y effective at similar concentrations or against the same fungal species.

] 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 ation, the particular plant species, e conditions, and the like.

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.

The following examples are provided for rative purposes and should not be construed as tions to the disclosure.

Examples tion of Curative and Protectant Activity of Fungicide Mixtures vs. Leaf Blotch of Wheat M cos haerella raminicola' anamo h: Se toria tritici' Ba er code: SEPTTR 1: Wheat plants (variety Yuma) were grown from seed in a ouse in plastic pots with a surface area of 27.5 square centimeters (cmz) containing 50% mineral soil/50% soil-less Metro mix, with 8-12 seedlings per pot. The plants were employed for g 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 (l-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 d mist chamber) to permit spores to germinate and infect the leaf. The plants were then transferred to a greenhouse for disease to develop.

Treatments consisted of fungicide compounds ostrobin, fluoxastrobin, azoxystrobin, trifloxystrobin, picoxystrobin, kresoxim-methyl, fluxapyroxad, benzovindiflupyr, penthiopyrad, isopyrazam, boscalid, fluopyram, prothioconazole, epoxiconazole, onazole, myclobutanil, metconazole, difenoconazole, propiconazole, fluquinconazole, flutriafol, mancozeb and chlorothalonil, either using dually or as two— wafixtures with the compound of Formula I.

[Annotation] m None set by cassarm [Annotation] cassarm MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm 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 ECso values were ated using JMP Pro 9.0. With the exception of azam, 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 ECso values. nd I was mixed with each fungicide based on ECso 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 1 and its mixing partners.

Ten milliliter (mL) fungicide ons were applied onto 8 pots of plants using an ted 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 es. All sprayed plants were allowed to air dry prior to further handling. Control plants were d in the same manner with the solvent blank.

When disease fully developed on the control plants, infection levels were assessed on d 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 ve to control plants.

Colby’s equation was used to determine the fungicidal effects expected from the mixtures. (See Colby, S. R. Calculation of the istic and antagonistic response of herbicide combinations. Weeds 1967, 15, 20—22.) The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: Expected = A + B — (A x B/100) A = observed cy of active component A at the same concentration as used in the mixture; B = ed y of active component B at the same concentration as used in the mixture. £0118] Representative synergistic interactions are presented in Tables 1 and 2.

[Annotation] cassarm None set by cassarm [Annotation] m MigrationNone set by cassarm [Annotation] cassarm Unmarked set by cassarm Table l: Synergistic Interactions of the Compound of Formula 1 and Other Fungicides in 1- Da Protectant lDP Septorz‘a z' SEPTTR Tests.

SEPTTR" ition Rates* Synergism (ppm) Observed* Factor Cmod.1 -— Eooxiconazole 1.18+0.06 89 1.26 Cmd.1 -— c roconazole 1.18+0.26 91 1.13 Cmd.1 -— Metconazole 118—064 86 1.21 Cmod.1 + tanil 1.18+4.81 95 1.35 Cmod.1 -— Pr0oiconazole 118—004 96 1.43 Cmod.1 -— Prothioconazole 1.18-—0.64 90 1.29 Cm.d.1 + Picox strobin 1.18+3.08 85 1.14 Cmod.1 -— Triflox strobin 1.18+0.3 84 1.15 Cmod.1 -— Azox strobin 118—064 94 1.39 Cmpd.1 + Fluoxastrobin 1.18+0.17 89 74 1.20 Cmpd.1 -- Boscalid l.l8--l.56 79 67 1.18 Cmd.1" + Iso. razam 8.41+10.9 100 91 1.10 Cmpd.1" -- Fluxapyroxad 8.41+l.92 100 42 2.41 Cmpd.1b -— Penthiopyrad 2.56+4.98 100 59 1.68 Cmpdl + Benzovindiflupyr 1.18+0.15 49 32 1.50 Cmd.1 —— Fluuinconazole 1.18+0.007 39 31 1.25 Cmod.1 -— Difenoconazole 1.18+0.0015 46 1.38 Cmd.1 + P raclostrobin 1.18+0.028 46 1.16 Cmod.1 -— Fluo. ram 1.18+4.19 43 1.26 Cmod.1 -— Flutriafol 1.18+0.23 30 1.10 Cmod.1 -— Kresoxim-methl 1.18+25 51 1.45 Cmd.1 -— Chlorothalonil 1.18+258 41 1.30 Cmod.1 + Mancozeb 1.18+321 42 1.34 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 on ppm = Parts per million ism factor = %DC ed / %DC Expected Cmpd 1 a = An EC ation of compound 1 was used as b Cmpd 1 = An SC formulation of compound 1 was used [Annotation] cassarm None set by cassarm [Annotation] cassarm MigrationNone set by m ation] cassarm Unmarked set by cassarm Table 2: Synergistic Interactions of the Compound of Formula I and Other Fungicides in 3- Da Curative 3DC Seltoria triticz' SEPTTR Tests.

SEPTTng . . Rates Synergism Composmon 4 4 (ppm) Factor Observed* Cmod.1 - azole 018—005 99 1.29 Cmd.1 - C roconazole 0.18--0.54 98 1.17 Cm.d.1 + Metconazole 0.18+0.08 93 1.38 Cmod.1 - M clobutanil 018-486 94 1.51 Cmod.1 - nazole 018—038 77 1.48 Cm-d.1 + Prothioconazole 0.18+3.89 58 1.18 Cmod.1 - Picox strobin .4 68 0.73 Cmod.1 - Triflox strobin 0.18+1.74 69 0.73 Cmod.1 - Azox strobin 0.18+0.83 61 0.77 Cmpd.1 - Fluoxastrobin 018—029 51 0.65 Cm.d.1 + Boscalid 0.18+2.37 43 93 0.46 Cmod.1" - Iso. razam 2.27—2.19 74 1.15 Cmpd.1" - Fluxapyroxad .36 71 53 1.33 Cmpd. 11’ + Penthiopyrad 0.2+0.86 77 61 1.25 Cmpd.1 - Benzovindiflupyr 0.18--0.54 72 56 1.29 Cmod.1 - Fluuinconazole 0.18+0.24 27 64 0.42 Cmpd.1 - Difenoconazole 0.18+0.0015 21 62 0.33 Cmpd.I - Pyraclostrobin 0.18+0.009 71 59 1.20 Cmod.1 + Fluo. ram 0.18+4.96 78 51 1.54 Cm.d.1 - Flutriafol 0.18+3.7 81 1.27 Cmd.1 - Kresoxim—methl 0.18+45 23 0.54 SEPTTR = Leaf Blotch of Wheat; Septorz’a triticz' DC Observed = Observed e 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 a = An EC formulation of compound 1 was used Cmpd 1 b = An SC formulation of compound 1 was used 1003772817

Claims (22)

WHAT IS CLAIMED:

1. A method for the control or prevention of fungal pathogen attack on a plant, the method comprising applying a synergistic fungicidal mixture, sing: as active ingredients, a fungicidally effective amount of the compound of Formula I: ; and at least one additional fungicide in which the at least one onal fungicide is (i) a fungicidal site inhibitor, wherein the concentration ratio of the compound of Formula I to fungicidal multi-site inhibitor is between 1:272 and 1:219 or (ii) a strobilurin fungicide, wherein the concentration ratio of the compound of Formula I to strobilurin fungicide is between 1:27 and 787:1.

2. The method of Claim 1, wherein a. the strobilurin fungicide is picoxystrobin and the concentration ratio of the compound of Formula I to picoxystrobin is between 2:1 and 1:2.5; or b. the strobilurin fungicide is azoxystrobin and the concentration ratio of Formula I compound to trobin is between 1:1 and 1:3.8; or c. the strobilurin fungicide is pyraclostrobin and the tration ratio of Formula I compound to pyraclostrobin is between 20:1 and 42:1; or d. the fungicidal multi-site inhibitor is mancozeb and the concentration ratio of Formula I compound to eb is between 1:1 and 1:20.

3. The method of Claim 1, n the mixture comprises at least one additional fungicide selected from the group consisting of captan, non, thiram, ziram, copper hydroxide, copper oxide, and copper oxychloride.

4. The method of any one of Claims 1-3, wherein the istic fungicidal mixture is effective in preventing diseases caused by fungal pathogens.

5. The method of any one of Claims 1-3, wherein the synergistic fungicidal mixture is effective in curing diseases caused by fungal pathogens.

6. The method of Claim 1, wherein the mixture is a tank mix. 1003772817

7. The method of any one of Claims 1-6, wherein the synergistic fungicidal mixture is applied to the roots, seeds or e of the plant.

8. The method of any one of Claims 1-7, wherein the plant is an agricultural crop.

9. The method of any one of Claims 1-8, wherein the synergistic fungicidal mixture is applied at a rate between 40 g/ha and 2600 g/ha relative to the compound of Formula I and (i) the fungicidal multi-site inhibitor or (ii) the strobilurin fungicide.

10. The method of any one of Claims 1-8, wherein the compound of Formula I is applied at a rate between 15 g/ha and 100 g/ha.

11. The method of any one of Claims 1-8, wherein: a. the multi-site inhibitor is applied at a rate between 1000 g/ha and 2600 g/ha; or b. the strobilurin fungicide is applied at a rate between 15 g/ha and 550 g/ha.

12. The method of any one of Claims 1-11, wherein: a. the strobilurin fungicide is picoxystrobin and the strobin is applied at a rate n 50 g/ha and 250 g/ha; or b. the strobilurin fungicide is trifloxystrobin and the trifloxystrobin is applied at a rate n 50 g/ha and 550 g/ha; or c. the strobilurin fungicide is azoxystrobin and the azoxystrobin is applied at a rate between 100 g/ha and 375 g/ha.

13. The method of any one of Claims 1-12, wherein the fungal pathogen is Leaf Blotch of Wheat (Mycosphaerella graminicola; anamorph: Septoria i), Wheat Brown Rust (Puccinia ina), Stripe Rust (Puccinia striiformis f. sp. tritici), Scab of Apple (Venturia inaequalis), Blister Smut of Maize (Ustilago maydis), Powdery Mildew of Grapevine (Uncinula r), 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), y Mildew of Barley (Blumeria graminis f. sp. hordei), y Mildew of Cucurbits (Erysiphe cichoracearum), Anthracnose of Cucurbits (Glomerella lagenarium), Leaf Spot of Beet (Cercospora la), Early Blight of Tomato (Alternaria solani), or Net Blotch of Barley (Pyrenophora teres).

14. The method of any one of Claims 1-12, wherein the fungal pathogen is Leaf Blotch of Wheat phaerella graminicola; anamorph: Septoria tritici).

15. The method of any one of Claims 1-14, wherein the synergistic fungicidal mixture is d in a composition, wherein the composition further comprises an agriculturally acceptable adjuvant or carrier. 1003772817

16. The method of Claim 15, wherein the ition is ated as a solution, dust, granular, wettable powder, flowable concentrate, emulsifiable concentrate, aqueous suspension, or emulsion.

17. The method of Claim 16, n: a. the concentration of the composition in the wettable powder is from about 10% to about 90% by weight; b. the concentration of the composition in the emulsifiable concentrate is from about 10% to about 50% by weight; c. the concentration of the composition in the granular is from about 0.5% to about 10% by weight; d. the concentration of the composition in the dust is from about 1% to about 10% by weight; or e. the concentration of the composition in the aqueous suspension is from about 5% to about 70% by weight.

18. The method of any one of Claims 1-17, wherein the synergistic fungicidal mixture is applied using a ground r or a granule applicator.

19. The method of any one of Claims 1-18, n the istic fungicidal mixture is applied as an additive to one or more additional fungicides or in a formulation with one or more additional fungicides.

20. A synergistic fungicidal composition comprising as active ingredients: a fungicidally effective amount of the compound of Formula I: and at least one onal fungicide in which the at least one additional fungicide is (i) a fungicidal multi-site inhibitor, wherein the concentration ratio of the compound of Formula I to fungicidal multi-site inhibitor is between 1:272 and about 1:219 or (ii) a strobilurin ide, wherein the tration ratio of the compound of Formula I to strobilurin fungicide is between 1:27 and about 787:1; and an agriculturally acceptable adjuvant or carrier.

21. The synergistic fungicidal composition of claim 20, wherein: 1003772817 a) the strobilurin fungicide is picoxystrobin and the concentration ratio of the compound of Formula I to picoxystrobin is between 2:1 and 1:2.5; or b) the strobilurin fungicide is azoxystrobin and the concentration ratio of Formula I compound to azoxystrobin is between 1:1 and 1:3.8; or c) the strobilurin fungicide is pyraclostrobin and the concentration ratio of Formula I compound to pyraclostrobin is between 20:1 and 42:1; or d) the fungicidal multi-site inhibitor is mancozeb and the tration ratio of a I compound to mancozeb is between 1:1 and 1:20. 22. A method for the control or prevention of fungal attack on a plant, the method comprising applying the istic fungicidal composition of Claim 20 or 21 to a locus of the fungus, to a locus in which the infestation is to be controlled or prevented, and/or to the plant.

22. Use of a synergistic fungicidal mixture of Claims 20 or 21 for the manufacturing of a fungicidal composition for controlling or preventing fungal attack on a plant, wherein the synergistic fungicidal ition is formulated for application on the plant, an area nt to the plant, soil adapted to support growth of the plant, a root of the plant, e of the plant, and/or a seed adapted to produce the plant.