FUNGICIDAL COMPOSITIONS

Abstract

A fungicidal composition comprising a mixture of components (A) and (B), wherein components (A) and (B) are as defined in claim 1, and use of the compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.

Claims

1. A fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is a compound of formula (I): ##STR00028## wherein R.sup.1 is methyl; R.sup.2 is hydrogen; R.sup.3 is hydrogen; R.sup.4 is C.sub.3-C.sub.7cycloalkyl; or an agronomically acceptable salt thereof; and component (B) is a compound selected from the group consisting of: bixafen, sulfur, copper hydroxide, triclopyricarb, acibenzolar-S-methyl, copper oxychloride, cyproconazole, difenoconazole, epoxicon-azole, flutriafol, hexaconazole, ipconazole, metconazole, paclobutrazole, prothioconazole, prochloraz, propiconazole, pyrisoxazole, tebucon-azole, fenpropidin, fenpropimorph, spiroxamine, cyprodinil, fludioxonil, metalaxyl, metalaxyl-M, carbendazim, penthiopyrad, azoxystrobin, dimoxystrobin, fenaminstrobin, flufenoxystrobin, fluoxastrobin, metomi-nostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, mancozeb, folpet, chlorothalonil, fluazinam, fluxapyroxad, fenhexamid, fos-etyl-aluminium, pyribencarb, tricyclazole, mandipropamid, flubeneteram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, isotianil, dipymetitrone, fluindapyr, coumethoxystrobin, lvbenmixianan, mandestrobin, oxathiapiprolin, pyraziflumid, inpyrfluxam, mefentrifluconazole, ipfentrifluconazole, aminopyrifen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, florylpicoxamid, fenpicoxamid, ipflufenoquin, quinofumelin, benzothiostrobin, fluopyram, pyrapropoyne, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, metyltetraprole, fluoxapiprolin, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, trinexapac, trinexapac-ethyl, coumoxystrobin, N′-[5-bromo methyl-6-[(1 S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N′-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N′-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N′-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N′-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine, N′-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N-isopropyl-N′-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, N′-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine, N-ethyl-N′-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N′-[5-methoxy-2-methyl-4-[2-trifuoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2 S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol amine, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl] oxy-2-methoxyimino-N, 3-dimethyl-pent-3-enamide, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N—[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N—[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl]-5-methyl-1,2,4-oxadiazole-3-carboxamide, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl] (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]propanoate, cis-jasmone, potassium phosphonate, calcium phosphonate, glyphosate, 2,4-D, dicamba, glufosinate, thiamethoxam, cyclobutrifluram, isocycloseram, spiropidion, abamectin, emamectin, cyantraniliprole, chlorantraniliprole, diafenthiuron, broflanilide, 2-chloro-N-cyclopropyl-5-(1-{2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-1H-pyrazol-4-yl)-N-methylnicotinamide and fluxametamide.

2. A fungicidal composition according claim 1, wherein component (A) is a compound selected from: methyl (Z)-2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (compound X.01), methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (compound X.02), methyl (Z)-2-(5-cyclopropyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (compound X.03), or methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (compound X.04); or an agronomically acceptable salt thereof.

3. A fungicidal composition according to claim 1, wherein component (A) is: methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (compound X.02), or methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (compound X.04); or an agronomically acceptable salt thereof.

4. A fungicidal composition according to claim 1, wherein component (B) is a compound selected from the group consisting of bixafen, triclopyricarb, cyproconazole, difenoconazole, epoxicon-azole, flutriafol, hexaconazole, ipconazole, metconazole, prothioconazole, propiconazole, tebucon-azole, azoxystrobin, dimoxystrobin, fenaminstrobin, flufenoxystrobin, fluoxastrobin, metomi-nostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, mancozeb, chlorothalonil, fluxapyroxad, pyribencarb, benzovindiflupyr, isoflucypram, coumethoxystrobin, mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, metyltetraprole, enoxastrobin, coumoxystrobin, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol -1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile.

5. A fungicidal composition according to claim 1, wherein component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin mancozeb, chlorothalonil, fluxapyroxad, benzovindiflupyr, isoflucypram and metyltetraprole.

6. A fungicidal composition according to claim 1, wherein component (B) is azoxystrobin or trifloxystrobin.

7. A fungicidal composition according to claim 1, wherein the weight ratio of component (A) to component (B) is from 100:1 to 1:100.

8. A fungicidal composition according to claim 1, wherein the weight ratio of component (A) to component (B) is from 20:1 to 1:40.

9. A fungicidal composition according to claim 1, wherein the weight ratio of component (A) to component (B) is from 12:1 to 1:25.

10. A fungicidal composition according to claim 1, wherein the weight ratio of component (A) to component (B) is from 5:1 and 1:15.

11. A fungicidal composition according to claim 1, wherein the weight ratio of component (A) to component (B) is from 2:1 to 1:5.

12. A fungicidal composition according to claim 1, wherein the composition comprises one or more further pesticides selected from the group consisting of: a fungicide, selected from etridiazole, fluazinam, benzovindiflupyr, pydiflumetofen, benalaxyl, benalaxyl-M (kiralaxyl), furalaxyl, metalaxyl, metalaxyl-M (mefenoxam), dodicin, N′-(2,5-Dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N′-[4-(4,5-Dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, N′-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl] oxy]-2, 5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, ethirimol, 3′-chloro-2-methoxy-N-[(3RS)-tetrahydro-2-oxofuran-3-yl]acet-2′,6′-xylidide (clozylacon), cyprodinil, mepanipyrim, pyrimethanil, dithianon, aureofungin, blasticidin-S, biphenyl, chloroneb, dicloran, hexachlorobenzene, quintozene, tecnazene, (TCNB), tolclofos-methyl, metrafenone, 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, fluopicolide (flupicolide), tioxymid, flusulfamide, benomyl, carbendazim, carbendazim chlorhydrate, chlorfenazole, fuberidazole, thiabendazole, thiophanate-methyl, benthiavalicarb, chlobenthiazone, probenazole, acibenzolar, bethoxazin, pyriofenone (IKF-309), acibenzolar-S-methyl, pyribencarb (KIF-7767), butylamine, 3-iodo-2-propinyl n-butylcarbamate (IPBC), iodocarb (isopropanyl butylcarbamate), isopropanyl butylcarbamate (iodocarb), picarbutrazox, polycarbamate, propamocarb, tolprocarb, 3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-tetramethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide diclocymet, N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-[(2-isopropylphenyl)methyl]-1-methyl-pyrazole-4-carboxamide carpropamid, chlorothalonil, flumorph, oxine-copper, cymoxanil, phenamacril, cyazofamid, flutianil, thicyofen, chlozolinate, iprodione, procymidone, vinclozolin, bupirimate, dinocton, dinopenton, dinobuton, dinocap, meptyldinocap, diphenylamine, phosdiphen, 2,6-dimethyl-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetraone, azithiram, etem, ferbam, mancozeb, maneb, metam, metiram (polyram), metiram-zinc, nabam, propineb, thiram, vapam (metam sodium), zineb, ziram, dithioether, isoprothiolane, ethaboxam, fosetyl, fosetyl-aluminium (fosetyl-al), methyl bromide, methyl iodide, methyl isothiocyanate, cyclafuramid, fenfuram, validamycin, streptomycin, (2RS)-2-bromo-2-(bromomethyl)glutaronitrile (bromothalonil), dodine, doguadine, guazatine, iminoctadine, iminoctadine triacetate, 2,4-D, 2,4-DB, kasugamycin, dimethirimol, fenhexamid, hymexazole, hydroxyisoxazole imazalil, imazalil sulphate, oxpoconazole, pefurazoate, prochloraz, triflumizole, fenamidone, Bordeaux mixture, calcium polysulfide, copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulphate, copper tallate, cuprous oxide, sulphur, carbaryl, phthalide (fthalide), dingjunezuo (Jun Si Qi), oxathiapiprolin, fluoroimide, mandipropamid, KSF-1002, benzamorf, dimethomorph, fenpropimorph, tridemorph, dodemorph, diethofencarb, fentin acetate, fentin hydroxide, carboxin, oxycarboxin, drazoxolon, famoxadone, m-phenylphenol, p-phenylphenol, tribromophenol (TBP), 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, cyflufenamid, ofurace, oxadixyl, flutolanil, mepronil, isofetamid, fenpiclonil, fludioxonil, pencycuron, edifenphos, iprobenfos, pyrazophos, phosphorus acids, tecloftalam, captafol, captan, ditalimfos, triforine, fenpropidin, piperalin, osthol, 1-methylcyclopropene, 4-CPA, chlormequat, clofencet, dichlorprop, dimethipin, endothal, ethephon, flumetralin, forchlorfenuron, gibberellic acid, gibberellins, hymexazol, maleic hydrazide, mepiquat, naphthalene acetamide, paclobutrazol, prohexadione, prohexadione-calcium, thidiazuron, tribufos (tributyl phosphorotrithioate), trinexapac, uniconazole, α-naphthalene acetic acid, polyoxin D (polyoxrim), BLAD, chitosan, fenoxanil, folpet, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, fenpyrazamine, diclomezine, pyrifenox, boscalid, fluopyram, diflumetorim, fenarimol, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine ferimzone, dimetachlone (dimethaclone), pyroquilon, proquinazid, ethoxyquin, quinoxyfen, 4,4,5-trifluoro-3,3-dimethyl-1-(3-quinolyl)isoquinoline 4,4-difluoro-3,3-dimethyl-1-(3-quinolyl)isoquinoline 5-fluoro-3,3,4,4-tetramethyl-1-(3-quinolyl)isoquinoline 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine, tebufloquin, oxolinic acid, chinomethionate (oxythioquinox, quinoxymethionate), spiroxamine, (E)-N-methyl-2-[2-(2, 5-dimethylphenoxymethyl) phenyl]-2-methoxy-iminoacetamide, (mandestrobin), azoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, pyriotrobin, fenamistrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metaminostrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, triclopyricarb, trifloxystrobin, amisulbrom, dichlofluanid, tolylfluanid, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, dazomet, isotianil, tiadinil, thifluzamide, benthiazole (TCMTB), silthiofam, zoxamide, anilazine, tricyclazole, (.+-.)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol (huanjunzuo), 1-(5-bromo-2-pyridyl)-2-(2,4-difluorophenyl)-1, 1-difluoro-3-(1,2,4-triazol-1-yl)propan-2-ol 2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol (TCDP), (N′-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine), azaconazole, bitertanol (biloxazol), bromuconazole, climbazole, cyproconazole, difenoconazole, dimetconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, mefentrifluconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triazoxide, triticonazole, 2-[[(1R,5S)-5-[(4-fluorophenyl)methyl]-1-hydroxy-2,2-dimethyl-cyclopentyl]methyl]-4H-1,2,4-triazole-3-thione 2-[[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl]-4H-1,2,4-triazole-3-thione, ametoctradin (imidium), iprovalicarb, valifenalate, 2-benzyl-4-chlorophenol (Chlorophene), allyl alcohol, azafenidin, benzalkonium chloride, chloropicrin, cresol, daracide, dichlorophen (dichlorophene), difenzoquat, dipyrithione, N-(2-p-chlorobenzoylethyl)-hexaminium chloride, NNF-0721, octhilinone, oxasulfuron, a plant extract comprising tea tree oil Melaleuca alternifolia (Timorex Gold™), a biostimulant comprising organic carbon, nutrients and amino acids (Quantis™), propamidine and propionic acid; or an insecticide selected from abamectin, acephate, acetamiprid, amidoflumet (S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, broflanilide, buprofezin, carbofuran, cartap, chlorantraniliprole (DPX-E2Y45), chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, tau-fluvalinate, flufenerim (UR-50701), flufenoxuron, fonophos, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaflumizone, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, nitenpyram, nithiazine, novaluron, noviflumuron (XDE-007), oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, pymetrozine, pyrafluprole, pyrethrin, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen (BSN 2060), spirotetramat, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, trichlorfon and triflumuron; or a bactericide selected from streptomycin; or an acaricide selected from amitraz, chinomethionat, chlorobenzilate, cyenopyrafen, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; or a biological agent selected from Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.

13. A fungicidal composition according to claim 1, wherein the composition further comprises an agriculturally acceptable carrier and, optionally, a surfactant and/or formulation adjuvants.

14. A method of controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi, on useful plants or on propagation material thereof, which comprises applying to the useful plants, the locus thereof or propagation material thereof a fungicidal composition as defined in claim 1.

15. A method according to claim 14, wherein the composition components (A) and (B) are applied in a sequential manner.

Description

EXAMPLES

[0164] The Examples which follow serve to illustrate the invention.

[0165] The compounds (and compositions) of the invention may be distinguished from known compounds (and compositions) by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.2 ppm of active ingredient(s).

[0166] Throughout this description, temperatures are given in degrees Celsius and “m.p.” means melting point. LC/MS means Liquid Chromatography Mass Spectroscopy and the description of the apparatus and the methods is as follows:

Method G:

[0167] Spectra were recorded on a Mass Spectrometer from Waters (SQD, SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and negative ions), Capillary: 3.00 kV, Cone range: 30 V, Extractor: 2.00 V, Source Temperature: 150° C., Desolvation Temperature: 350° C., Cone Gas Flow: 50 I/h, Desolvation Gas Flow: 650 L/h, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment, diode-array detector and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm, Temp: 60° C., DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH, gradient: 10-100% B in 1.2 min; Flow (mL/min) 0.85

Method H:

[0168] Spectra were recorded on a Mass Spectrometer from Waters (SQD, SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and negative ions), Capillary: 3.00 kV, Cone range: 30V, Extractor: 2.00 V, Source Temperature: 150° C., Desolvation Temperature: 350° C., Cone Gas Flow: 50 L/h, Desolvation Gas Flow: 650 L/h, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment, diode-array detector and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm, Temp: 60° C., DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH, gradient: 10-100% B in 2.7 min; Flow (mL/min) 0.85

[0169] Where necessary, enantiomerically pure final compounds may be obtained from racemic materials as appropriate via standard physical separation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, eg, by using chiral starting materials.

FORMULATION EXAMPLES

[0170]

TABLE-US-00002 Wettable powders a) b) c) active ingredients [components (A) and (B)] 25%  50% 75% sodium lignosulfonate 5%  5% — sodium lauryl sulfate 3% —  5% sodium diisobutylnaphthalenesulfonate —  6% 10% phenol polyethylene glycol ether —  2% — (7-8 mol of ethylene oxide) highly dispersed silicic acid 5% 10% 10% Kaolin 62%  27% —

[0171] The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.

TABLE-US-00003 Powders for dry seed treatment a) b) C) active ingredients [components (A) and (B)] 25% 50% 75% light mineral oil  5%  5%  5% highly dispersed silicic acid  5%  5% — Kaolin 65% 40% — Talcum — — 20%

[0172] The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

TABLE-US-00004 Emulsifiable concentrate active ingredients [components (A) and (B)] 10% octylphenol polyethylene glycol ether (4-5 mol of ethylene oxide)  3% calcium dodecylbenzenesulfonate  3% castor oil polyglycol ether (35 mol of ethylene oxide)  4% Cyclohexanone 30% xylene mixture 50%

[0173] Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

TABLE-US-00005 Dusts a) b) C) active ingredients [components (A) and (B)]  5%  6%  4% talcum 95% — — Kaolin — 94% — mineral filler — — 96%

[0174] Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.

TABLE-US-00006 Extruder granules active ingredients [components (A) and (B)] 15% sodium lignosulfonate  2% carboxymethylcellulose  1% Kaolin 82%

[0175] The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

TABLE-US-00007 Coated granules active ingredients [components (A) and (B)] 8% polyethylene glycol (mol. wt. 200) 3% Kaolin 89% 

[0176] The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

TABLE-US-00008 Suspension concentrate active ingredients [components (A) and (B)] 40% propylene glycol 10% nonylphenol polyethylene glycol ether (15 mol of ethylene oxide)  6% Sodium lignosulfonate 10% carboxymethylcellulose  1% silicone oil (in the form of a 75% emulsion in water)  1% Water 32%

[0177] The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

TABLE-US-00009 Flowable concentrate for seed treatment active ingredients [components (A) and (B)] 40%  propylene glycol 5% copolymer butanol PO/EO 2% tristyrenephenole with 10-20 moles EO 2% 1,2-benzisothiazolin-3-one (in the form of a 20% solution in 0.5%.sup.  water) monoazo-pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2%.sup.  Water 45.3%  

[0178] The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

Slow Release Capsule Suspension

[0179] 28 parts of a combination of the active ingredients [components (A) and (B)] is mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51.6 parts of water until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

List of Abbreviations

[0180] Aq.=aqueous [0181] br s=broad singlet [0182] ° C.=degrees Celsius [0183] DCM=dichloromethane [0184] dd=doublet of doublet [0185] DMF=dimethylformamide [0186] DMSO=dimethyl sulfoxide [0187] DMSO-d.sub.6=deuterated dimethyl sulfoxide [0188] d=doublet [0189] EtOAc=ethyl acetate [0190] equiv.=equivalent [0191] h=hour(s) [0192] M=molar [0193] m=mulitplet [0194] min=minutes [0195] MHz=mega hertz [0196] mp=melting point [0197] Pd.sub.2(dba).sub.3=tris(dibenzylideneacetone)dipalladium(0) [0198] Pd(dppf)Cl.sub.2 DCM=[1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), DCM complex [0199] Pd(PPh.sub.3).sub.2Cl.sub.2=bis(triphenylphosphine) palladium (II) dichloride [0200] ppm=parts per million [0201] RT=room temperature [0202] Rt=retention time [0203] s=singlet [0204] t=triplet [0205] THF=tetrahydrofuran [0206] LC/MS=Liquid Chromatography Mass Spectrometry (description of the apparatus and the methods used for LC/MS analysis are given above) [0207] X-Phos Pd G2=chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)

PREPARATION EXAMPLES

Example 1: This example illustrates the preparation of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (compound X.04)

Step 1: Preparation of methyl 2-(5-bromo-2-methyl-phenoxy)acetate

[0208] ##STR00015##

[0209] To a solution of 5-bromo-2-methylphenol (53.47 mmol, 10.00 g) and methyl 2-bromoacetate (1.5 equiv., 80.20 mmol, 12.27 g, 7.44 mL) in tetrahydrofuran (0.5 mol/L, 106.9 mL) at room temperature was added potassium carbonate (2 equiv., 106.9 mmol, 14.78 g), and the light brown suspension was heated to 65° C. for 2 h and then allowed to cool down to room temperature overnight. The reaction mixture was diluted with EtOAc and washed with water. The aqueous phase was extracted with EtOAc, and the total combined organic layer was washed with water, brine, dried with Na.sub.2SO.sub.4, filtered and concentrated in vacuo to give methyl 2-(5-bromo-2-methyl-phenoxy)acetate (47.22 mmol, 15.89 g, 88% yield) as a brown liquid. The crude oil was slightly contaminated with residual methyl-2-bromoacetate, but was taken directly to the next step without further purification.

[0210] LCMS (Method H), Rt=1.59 min, MS: (M+1)=259, 261; .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm 2.25 (s, 3H) 3.84 (s, 3H) 4.66 (s, 2H) 6.84 (d, 1H) 7.05 (m, 2H)

Step 2: Preparation of methyl (Z)-2-(5-bromo-2-methyl-phenoxy)-3-methoxy-prop-2-enoate

[0211] ##STR00016##

[0212] Part 1: To a solution of 2-(5-bromo-2-methyl-phenoxy)acetate (20.8 g, 80.3 mmol) and methyl formate (6.0 equiv., 482 mmol, 29.5 g, 30.5 mL) in tetrahydrofuran (0.5 mol/L, 161 mL) at room temperature under argon was added sodium methoxide (20 equiv., 161 mmol, 9.13 g) portionwise. The reaction was slightly exothermic and was kept below 30° C. with the assistance of a room temperature water bath. The reaction mixture was stirred at room temperature for 1 h and quenched by the slow addition of an aqueous saturated solution of NaHCO.sub.3. The two phases were separated and the aqueous phase was extracted with EtOAc. The total combined organic layer was washed with aqueous saturated solution of NaHCO.sub.3, brine, dried with Na.sub.2SO.sub.4, filtered and concentrated in vacuo to give methyl-2-(5-bromo-2-methyl-phenoxy)-3-hydroxy-prop-2-enoate, which was taken directly to the next step without further purification.

[0213] LCMS (Method G), Rt=0.80 and 0.90 min, MS: (M+1)=287, 289

[0214] Part 2: To a solution of the crude methyl-2-(5-bromo-2-methyl-phenoxy)-3-hydroxy-prop-2-enoate and dimethyl sulfate (1.2 equiv., 93.2 mmol, 11.8 g, 8.8 mL) in DMF (0.5 mol/L, 155 mL) at room temperature under argon was added potassium carbonate (1.5 equiv., 117 mmol, 16.3 g), and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched by the slow addition of water, and the mixture was extracted with EtOAc. The total combined organic layer was washed with aqueous saturated solution of NaHCO.sub.3, brine, dried with Na.sub.2SO.sub.4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl (Z)-2-(5-bromo-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (59.6 mmol, 18.0 g, 75% yield) as an off-white solid. LCMS (Method G), Rt=1.02 min, MS: (M+1)=301, 303; .sup.1H NMR (400 MHz, CDCl.sup.3) δ ppm 2.31 (s, 3H) 3.74 (s, 3H) 3.91 (s, 3H) 6.86 (d, 1H) 7.05 (m, 2H) 7.35 (s, 1H)

Step 3: Preparation of methyl (Z)-2-[5-(cyclohexen-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate

[0215] ##STR00017##

[0216] To a solution of methyl (Z)-2-(5-bromo-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (203 mg, 0.67 mmol, 1.00 equiv.), in 1,4-dioxane (6 mL) and water (1 mL) was added cyclohexen-1-ylboronic acid (93.4 mg, 0.74 mmol, 1.10 equiv.), potassium phosphate (295 mg, 1.35 mmol, 2.00 equiv.) and X Phos Pd G2 (53.0 mg, 0.07 mmol, 0.10 equiv.). The reaction mixture was stirred at 100° C. for 15 min and the heating source was removed. After the contents reached RT, was diluted with EtOAc and a saturated aqueous NaHCO.sub.3 solution then extracted with EtOAc. The total combined organic fraction was washed with and a saturated aqueous NaHCO.sub.3 solution and brine, dried with Na.sub.2SO.sub.4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl (Z)-2-[5-(cyclohexen-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate as an amorphous solid.

[0217] LC-MS (Method G), Rt=1.17 min, MS: (M+H)=303; .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm 7.36 (s, 1H), 7.11 (d, 1H), 6.96 (dd, 1H), 6.77 (d, 1H), 6.04 (m, 1H), 3.90 (s, 3H), 3.74 (s, 3H), 2.36 (m, 5H), 2.17-2.25 (m, 2H), 1.74-1.83 (m, 2H), 1.63-1.71 (m, 2H).

Step 4: Preparation of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (Compound X.04)

[0218] ##STR00018##

[0219] To a solution of methyl (Z)-2-[5-(cyclohexen-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate (132 mg, 0.44 mmol, 1.00 equiv.), in hexane (0.87 mL) and EtOAc (2.18 mL) was added palladium on carbon (23.2 mg, 0.01 mmol, 0.02 equiv.). The reaction mixture was stirred under hydrogen atmosphere for 2 days. The reaction mixture was filtered over celite and concentrated in vacuo. The resultant crude residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as a white solid (mp: 131-132° C.).

[0220] LC-MS (Method G), R.sub.t=1.21 min, MS: (M+H)=305; .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm ppm 7.35 (s, 1H), 7.10 (d, 1H), 6.79 (dd, 1H), 6.58 (d, 1H), 3.90 (s, 3H), 3.74 (s, 3H), 2.38-2.47 (m, 1H), 2.34 (s, 3H), 1.80-1.89 (m, 4H), 1.75 (br, 1H), 1.33-1.42 (m, 4H), 1.22-1.32 (m, 1H).

Example 2: This example illustrates the preparation of methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (Compound X.02)

[0221] ##STR00019##

[0222] Under an argon atmosphere, a zinc chloride 1M THF solution (2.54 mmol) was added to a cyclopentyl magnesium bromide 2M THF solution (2.54 mmol) and the pale yellow suspension was stirred at RT for 10 min during time which a small exotherm was observed. After, a solution of methyl (Z)-2-(5-bromo-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (0.153 g, 0.51 mmol) in tetrahydrofuran (2.5 mL) and PdCl.sub.2(dppf) (0.19 g, 0.025 mmol) were added and the pale yellow suspension was heated at 50° C. for 3 hours. The reaction mixture was then allowed to reach RT, quenched with an aqueous saturated NH.sub.4Cl solution, and extracted with tert-butyl methylether. The total combined organic fraction was then washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resultant crude residue was purified by flash chromatography (cyclohexane:EtOAc gradient) to give 0.106 mg the title compound as a white solid (mp 80-83° C.).

[0223] LC-MS (Method G), R.sub.1=1.16 min, MS: (M+H)=291; .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm: 7.35 (s, 1H), 7.09 (d, 1H), 6.82 (d, 1H), 6.60 (s, 1H), 3.90 (s, 3H), 3.72 (s, 3H), 2.91 (m, 1H), 2.32 (s, 3H), 2.10-1.97 (m, 2H), 1.85-1.75 (m, 2H), 1.74-1.65 (m, 2H), 1.60-1.45 (m, 2H).

[0224] Using the synthetic techniques described both above and below, compounds of formula (I) may be prepared accordingly.

[0225] Where necessary, enantiomerically pure final compounds may be obtained from racemic materials as appropriate via standard physical separation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, (eg, by using chiral starting materials).

TABLE-US-00010 TABLE T1 Melting point (mp) data and/or retention times (Rt) for compounds X.01 to X.04 according to formula (I): Mass charge LCMS mp Entry Compound structure Compound name Rt (min) [M + H] Method (° C.) X.01 [00020] methyl (Z)-2-(5- cyclobutyl-2- methyl-phenoxy)- 3-methoxy-prop- 2-enoate 1.13 277 G X.02 [00021] methyl (Z)-2-(5- cyclopentyl-2- methyl-phenoxy)- 3-methoxy-prop- 2-enoate 80-83 X.03 [00022] methyl (Z)-2-(5- cyclopropyl-2- methyl-phenoxy)- 3-methoxy-prop- 2-enoate 1.04 263 G X.04 [00023] methyl (Z)-2-(5- cyclohexyl-2- methyl-phenoxy)- 3-methoxy-prop- 2-enoate 131-132

BIOLOGICAL EXAMPLES

General Examples of Leaf Disk Tests in Well Plates:

[0226] Leaf disks or leaf segments of various plant species are cut from plants grown in a greenhouse. The cut leaf disks or segments are placed in multiwell plates (24-well format) onto water agar. The leaf disks are sprayed with a test solution before (preventative) or after (curative) inoculation. Compounds to be tested are prepared as DMSO solutions (max. 10 mg/mL) which are diluted to the appropriate concentration with 0.025% Tween20 just before spraying. The inoculated leaf disks or segments are incubated under defined conditions (temperature, relative humidity, light, etc.) according to the respective test system. A single evaluation of disease level is carried out 3 to 14 days after inoculation, depending on the pathosystem. Percent disease control relative to the untreated check leaf disks or segments is then calculated.

General Examples of Liquid Culture Tests in Well Plates:

[0227] Mycelia fragments or conidia suspensions of a fungus prepared either freshly from liquid cultures of the fungus or from cryogenic storage, are directly mixed into nutrient broth. DMSO solutions of the test compound (max. 10 mg/mL) are diluted with 0.025% Tween20 by a factor of 50 and 10 μl of this solution is pipetted into a microtiter plate (96-well format). The nutrient broth containing the fungal spores/mycelia fragments is then added to give an end concentration of the tested compound. The test plates are incubated in the dark at 24° C. and 96% relative humidity. The inhibition of fungal growth is determined photometrically after 2 to 7 days, depending on the pathosystem, and percent antifungal activity relative to the untreated check is calculated.

Example A1: Fungicidal Activity Against Puccinia recondita f. sp. Tritici/Wheat/Leaf Disc Preventative (Brown Rust)

[0228] Wheat leaf segments are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf segments are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed 8 dpi (days after inoculation) as preventative fungicidal activity.

[0229] The following compounds gave at least 80% control of Puccinia recondita f. sp. tritici at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

[0230] Compounds (from Table T1): X.01, X.02. X.03, X.04

Example A2: Fungicidal Activity Against Puccinia recondita f. sp. Tritici/Wheat/Leaf Disc Curative (Brown Rust)

[0231] Wheat leaf segments are placed on agar in multiwell plates (24-well format). The leaf segments are inoculated with a spore suspension of the fungus and sprayed with test solutions 1 day after inoculation. After appropriate incubation the activity of a compound is assessed 8 dpi (days after inoculation) as curative fungicidal activity.

[0232] The following compounds gave at least 80% control of Puccinia recondita f. sp. tritici at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

[0233] Compounds (from Table T1): X.01, X.02, X.04

Example A3: Fungicidal Activity Against Phakopsora pachyrhizi Soybean/Leaf Disc Preventative (Asian Soybean Rust)

[0234] Soybean leaf disks are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed approx. 12 dpi (days after inoculation) as preventive fungicidal activity.

[0235] The following compounds gave at least 70% control of Phakopsora pachyrhizi at 60 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

[0236] Compounds (from Table T1): X.01, X.02. X.03, X.04

Example A4: Fungicidal Activity Against Glomerella lagenarium (Colletotrichum lagenarium) Liquid Culture/Cucumber/Preventative (Anthracnose)

[0237] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically after 72 hrs at 620 nm. The following compounds gave at least 80% control of Glomerella lagenarium at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development:

[0238] Compounds (from Table T1): X.01, X.02. X.03, X.04

Comparative Data:

[0239] The biological activity of compounds X.02 and X.04 of the invention are compared to the reference compounds Z-1 and Z-2. Reference compounds Z-1 and Z-2 are specifically disclosed on page 16 of WO 98/03464 and page 6 of EP 0 212 859 respectively.

Example B: Comparative Biological Activity Against Puccinia recondita (Brown Rust), Curative

[0240] Method; Wheat leaf segments are placed on agar in multiwell plates (24-well format). The leaf segments are inoculated with a spore suspension of the fungus and sprayed with test solutions 1 day after inoculation. After appropriate incubation the activity of a compound is assessed 8 dpi (days after inoculation) as curative fungicidal activity.

[0241] The data are presented as the percentage of disease control of each compound for the biological tests and testing rates described below in table B1.

TABLE-US-00011 TABLE B1 Biological activity against Puccinia recondita (Brown rust), curative: Concentration Compound Compound structure (PPm) control (%) Compound X.04 [00024] 200  60  20 100 100  90 Compound X.02 [00025] 200  60  20 100   0   0 Reference Compound Z-1 (WO 98/03464) [00026] 200  60  20   0   0   0 Reference Compound Z-2 (EP 0 212 859) [00027] 200  60  20   0   0   0

[0242] Further biological test examples relating to fungicidal compositions comprising a mixture of components (A) and (B) as active ingredients:

Example C1 Fungicidal Activity Against Mycosphaerella arachidis syn. Cercospora arachidicola (Brown Leaf Spot)

[0243] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically after approximately 5-6 days at 620 nm

[0244] The following compound mixtures gave at least 80% control Mycosphaerella arachidis at rates cited in the table when compared to untreated control under the same conditions, which showed extensive disease development:

TABLE-US-00012 TABLE C1-1 Fungicidal activity >80% (% of untreated) against Mycosphaerella arachidis Conc. Ratio (ppm) Component A Component B A:B (A:B) X.02 glyphosate 1:1 0.1 + 0.1 X.02 glyphosate 1:3 0.1 + 0.3 X.02 chlorothalonil 1:1 0.1 + 0.1 X.02 chlorothalonil 1:3 0.1 + 0.3 X.02 chlorothalonil  1:10 0.03 + 0.3  X.02 mancozeb 1:1 0.1 + 0.1 X.02 mancozeb 1:3 0.1 + 0.3 X.02 2,4-D 1:1 0.1 + 0.1 X.02 2,4-D 1:3 0.1 + 0.3 X.02 propiconazole 1:1 0.1 + 0.1 X.02 propiconazole 1:3 0.1 + 0.3 X.02 propiconazole  3:10 0.03 + 0.1  X.02 propiconazole  1:10 0.03 + 0.3  X.02 disodium phosphonate 1:1 0.1 + 0.1 X.02 disodium phosphonate 1:3 0.1 + 0.3 X.02 fenpropimorph 1:1 0.1 + 0.1 X.02 fenpropimorph 1:3 0.1 + 0.3 X.02 fenpropimorph  3:10 0.03 + 0.1  X.02 fenpropimorph  1:10 0.03 + 0.3  X.02 fenpropidin 1:1 0.1 + 0.1 X.02 fenpropidin 1:3 0.1 + 0.3 X.02 fenpropidin  1:10 0.03 + 0.3  X.02 hexaconazole 1:1 0.1 + 0.1 X.02 hexaconazole 1:3 0.1 + 0.3 X.02 hexaconazole  3:10 0.03 + 0.1  X.02 hexaconazole  1:10 0.03 + 0.3  X.02 paclobutrazol 1:1 0.1 + 0.1 X.02 paclobutrazol 1:3 0.1 + 0.3 X.02 trinexapac-ethyl 1:1 0.1 + 0.1 X.02 trinexapac-ethyl 1:3 0.1 + 0.3 X.02 flutriafol 1:1 0.1 + 0.1 X.02 flutriafol 1:3 0.1 + 0.3 X.02 difenoconazole 1:1 0.1 + 0.1 X.02 difenoconazole 1:3 0.1 + 0.3 X.02 difenoconazole  3:10 0.03 + 0.1  X.02 difenoconazole  1:10 0.03 + 0.3  X.02 cyproconazole 1:1 0.1 + 0.1 X.02 cyproconazole 1:3 0.1 + 0.3 X.02 cyproconazole  1:10 0.03 + 0.3  X.02 acibenzolar S-methyl 1:1 0.1 + 0.1 X.02 acibenzolar S-methyl 1:3 0.1 + 0.3 X.02 trifloxystrobin 1:1 0.1 + 0.1 X.02 trifloxystrobin 1:3 0.1 + 0.3 X.02 trifloxystrobin  3:10 0.03 + 0.1  X.02 trifloxystrobin  1:10 0.03 + 0.3  X.02 folpet 1:1 0.1 + 0.1 X.02 folpet 1:3 0.1 + 0.3 X.02 azoxystrobin 1:1 0.1 + 0.1 X.02 azoxystrobin 1:3 0.1 + 0.3 X.02 azoxystrobin  3:10 0.03 + 0.1  X.02 azoxystrobin  1:10 0.03 + 0.3  X.02 pyraclostrobin 1:1 0.1 + 0.1 X.02 pyraclostrobin 1:3 0.1 + 0.3 X.02 pyraclostrobin  3:10 0.03 + 0.1  X.02 pyraclostrobin  1:10 0.03 + 0.3  X.02 picoxystrobin 1:1 0.1 + 0.1 X.02 picoxystrobin 1:3 0.1 + 0.3 X.02 picoxystrobin  3:10 0.03 + 0.1  X.02 picoxystrobin  1:10 0.03 + 0.3  X.02 sulphur 1:1 0.1 + 0.1 X.02 sulphur 1:3 0.1 + 0.3 X.02 tebuconazole 1:1 0.1 + 0.1 X.02 tebuconazole 1:3 0.1 + 0.3 X.02 tebuconazole  1:10 0.03 + 0.3  X.02 prothioconazole 1:1 0.1 + 0.1 X.02 prothioconazole 1:3 0.1 + 0.3 X.02 prothioconazole  3:10 0.03 + 0.1  X.02 prothioconazole  1:10 0.03 + 0.3  X.02 fluopyram 1:1 0.1 + 0.1 X.02 fluopyram 1:3 0.1 + 0.3 X.02 fluopyram  1:10 0.03 + 0.3  X.02 copper oxychloride 1:1 0.1 + 0.1 X.02 copper oxychloride 1:3 0.1 + 0.3 X.02 benzovindiflupyr 1:1 0.1 + 0.1 X.02 benzovindiflupyr 1:3 0.1 + 0.3 X.02 benzovindiflupyr  3:10 0.03 + 0.1  X.02 benzovindiflupyr  1:10 0.03 + 0.3  X.02 isopyrazam 1:1 0.1 + 0.1 X.02 isopyrazam 1:3 0.1 + 0.3 X.02 isopyrazam  3:10 0.03 + 0.1  X.02 isopyrazam  1:10 0.03 + 0.3  X.02 pydiflumetofen 1:1 0.1 + 0.1 X.02 pydiflumetofen 1:3 0.1 + 0.3 X.02 pydiflumetofen  3:10 0.03 + 0.1  X.02 pydiflumetofen  1:10 0.03 + 0.3  X.02 fluxapyroxad 1:1 0.1 + 0.1 X.02 fluxapyroxad 1:3 0.1 + 0.3 X.02 fluxapyroxad  3:10 0.03 + 0.1  X.02 fluxapyroxad  1:10 0.03 + 0.3  X.02 quinofumelin 1:1 0.1 + 0.1 X.02 quinofumelin 1:3 0.1 + 0.3 X.02 isoflucypram 1:1 0.1 + 0.1 X.02 isoflucypram 1:3 0.1 + 0.3 X.02 isoflucypram  3:10 0.03 + 0.1  X.02 isoflucypram  1:10 0.03 + 0.3  X.02 mefentrifluconazole 1:1 0.1 + 0.1 X.02 mefentrifluconazole 1:3 0.1 + 0.3 X.02 mefentrifluconazole  3:10 0.03 + 0.1  X.02 mefentrifluconazole  1:10 0.03 + 0.3  X.02 ipflufenoquin 1:1 0.1 + 0.1 X.02 ipflufenoquin 1:3 0.1 + 0.3 X.02 metyltetraprole 1:1 0.1 + 0.1 X.02 metyltetraprole 1:3 0.1 + 0.3 X.02 metyltetraprole  3:10 0.03 + 0.1  X.02 metyltetraprole  1:10 0.03 + 0.3  X.02 aminopyrifen 1:1 0.1 + 0.1 X.02 aminopyrifen 1:3 0.1 + 0.3 X.02 aminopyrifen  3:10 0.03 + 0.1  X.02 aminopyrifen  1:10 0.03 + 0.3  X.02 florylpicoxamid 1:1 0.1 + 0.1 X.02 florylpicoxamid 1:3 0.1 + 0.3 X.02 florylpicoxamid  3:10 0.03 + 0.1  X.02 florylpicoxamid  1:10 0.03 + 0.3  X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1- 1:1 0.1 + 0.1 (1,2,4-triazol-1-yl)propan-2-ol X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1- 1:3 0.1 + 0.3 (1,2,4-triazol-1-yl)propan-2-ol X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-  3:10 0.03 + 0.1  (1,2,4-triazol-1-yl)propan-2-ol X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-  1:10 0.03 + 0.3  (1,2,4-triazol-1-yl)propan-2-ol X.02 fenpicoxamid 1:1 0.1 + 0.1 X.02 fenpicoxamid 1:3 0.1 + 0.3 X.02 fenpicoxamid  3:10 0.03 + 0.1  X.02 fenpicoxamid  1:10 0.03 + 0.3  X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:1 0.1 + 0.1 methoxyimino-N,3-dimethyl-pent-3-enamide X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:3 0.1 + 0.3 methoxyimino-N,3-dimethyl-pent-3-enamide X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  3:10 0.03 + 0.1  methoxyimino-N,3-dimethyl-pent-3-enamide X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  1:10 0.03 + 0.3  methoxyimino-N,3-dimethyl-pent-3-enamide X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 50:3    1 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 25:3   0.5 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 25:6  0.25 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 25:12 0.125 + 0.06  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 25:24 0.0625 + 0.06  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 25:48 0.03125 + 0.06   methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 100:3    1 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 50:3   0.5 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 50:6  0.25 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 50:12 0.125 + 0.03  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 50:24 0.0625 + 0.03  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 50:48 0.03125 + 0.03   methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:20  1 + 20 oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:40 0.5 + 20  oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:80 0.25 + 20.sup.  oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:160 0.125 + 20   oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:320 0.0625 + 20    oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:10  1 + 10 oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:20 0.5 + 10  oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:40 0.25 + 10.sup.  oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:80 0.125 + 10   oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:160 0.0625 + 10    oxadiazol-3-yl]benzamide X.02 Florylpicoxamid 50:1    1 + 0.02 X.02 Florylpicoxamid 25:1   0.5 + 0.02 X.02 Florylpicoxamid 25:2  0.25 + 0.02 X.02 Florylpicoxamid 25:4  0.125 + 0.02  X.02 Florylpicoxamid 25:8  0.0625 + 0.02  X.02 Florylpicoxamid 25:16 0.03125 + 0.02   X.02 Florylpicoxamid 100:1    1 + 0.01 X.02 Florylpicoxamid 50:1   0.5 + 0.01 X.02 Florylpicoxamid 25:1  0.25 + 0.01 X.02 Florylpicoxamid 25:2  0.125 + 0.01  X.02 Florylpicoxamid 25:4  0.0625 + 0.01  X.02 Florylpicoxamid 25:8  0.03125 + 0.01  

TABLE-US-00013 TABLE C1-2 Fungicidal activity >80% (% of untreated) against Mycosphaerella arachidis Conc. Ratio (ppm) Component A Component B A:B (A:B) X.04 glyphosate 1:1 0.1 + 0.1 X.04 glyphosate 1:3 0.1 + 0.3 X.04 glyphosate  3:10 0.03 + 0.1  X.04 glyphosate  1:10 0.03 + 0.3  X.04 chlorothalonil 1:1 0.1 + 0.1 X.04 chlorothalonil 1:3 0.1 + 0.3 X.04 chlorothalonil  3:10 0.03 + 0.1  X.04 chlorothalonil  1:10 0.03 + 0.3  X.04 mancozeb 1:1 0.1 + 0.1 X.04 mancozeb 1:3 0.1 + 0.3 X.04 mancozeb  3:10 0.03 + 0.1  X.04 mancozeb  1:10 0.03 + 0.3  X.04 2,4-D 1:1 0.1 + 0.1 X.04 2,4-D 1:3 0.1 + 0.3 X.04 2,4-D  3:10 0.03 + 0.1  X.04 2,4-D  1:10 0.03 + 0.3  X.04 propiconazole 1:1 0.1 + 0.1 X.04 propiconazole 1:3 0.1 + 0.3 X.04 propiconazole  3:10 0.03 + 0.1  X.04 propiconazole  1:10 0.03 + 0.3  X.04 disodium phosphonate 1:1 0.1 + 0.1 X.04 disodium phosphonate 1:3 0.1 + 0.3 X.04 disodium phosphonate  3:10 0.03 + 0.1  X.04 disodium phosphonate  1:10 0.03 + 0.3  X.04 fenpropimorph 1:1 0.1 + 0.1 X.04 fenpropimorph 1:3 0.1 + 0.3 X.04 fenpropimorph  3:10 0.03 + 0.1  X.04 fenpropimorph  1:10 0.03 + 0.3  X.04 fenpropidin 1:1 0.1 + 0.1 X.04 fenpropidin 1:3 0.1 + 0.3 X.04 fenpropidin  1:10 0.03 + 0.3  X.04 hexaconazole 1:1 0.1 + 0.1 X.04 hexaconazole 1:3 0.1 + 0.3 X.04 hexaconazole  3:10 0.03 + 0.1  X.04 hexaconazole  1:10 0.03 + 0.3  X.04 paclobutrazol 1:1 0.1 + 0.1 X.04 paclobutrazol 1:3 0.1 + 0.3 X.04 paclobutrazol  3:10 0.03 + 0.1  X.04 paclobutrazol  1:10 0.03 + 0.3  X.04 trinexapac-ethyl 1:1 0.1 + 0.1 X.04 trinexapac-ethyl 1:3 0.1 + 0.3 X.04 trinexapac-ethyl  3:10 0.03 + 0.1  X.04 trinexapac-ethyl  1:10 0.03 + 0.3  X.04 flutriafol 1:1 0.1 + 0.1 X.04 flutriafol 1:3 0.1 + 0.3 X.04 difenoconazole 1:1 0.1 + 0.1 X.04 difenoconazole 1:3 0.1 + 0.3 X.04 difenoconazole  3:10 0.03 + 0.1  X.04 difenoconazole  1:10 0.03 + 0.3  X.04 fludioxonil 1:1 0.1 + 0.1 X.04 fludioxonil 1:3 0.1 + 0.3 X.04 cyproconazole 1:1 0.1 + 0.1 X.04 cyproconazole 1:3 0.1 + 0.3 X.04 cyproconazole  1:10 0.03 + 0.3  X.04 acibenzolar S-methyl 1:1 0.1 + 0.1 X.04 acibenzolar S-methyl 1:3 0.1 + 0.3 X.04 acibenzolar S-methyl  3:10 0.03 + 0.1  X.04 acibenzolar S-methyl  1:10 0.03 + 0.3  X.04 trifloxystrobin 1:1 0.1 + 0.1 X.04 trifloxystrobin 1:3 0.1 + 0.3 X.04 trifloxystrobin  3:10 0.03 + 0.1  X.04 trifloxystrobin  1:10 0.03 + 0.3  X.04 folpet 1:1 0.1 + 0.1 X.04 folpet 1:3 0.1 + 0.3 X.04 folpet  3:10 0.03 + 0.1  X.04 folpet  1:10 0.03 + 0.3  X.04 azoxystrobin 1:1 0.1 + 0.1 X.04 azoxystrobin 1:3 0.1 + 0.3 X.04 azoxystrobin  3:10 0.03 + 0.1  X.04 azoxystrobin  1:10 0.03 + 0.3  X.04 pyraclostrobin 1:1 0.1 + 0.1 X.04 pyraclostrobin 1:3 0.1 + 0.3 X.04 pyraclostrobin  3:10 0.03 + 0.1  X.04 pyraclostrobin  1:10 0.03 + 0.3  X.04 picoxystrobin 1:1 0.1 + 0.1 X.04 picoxystrobin 1:3 0.1 + 0.3 X.04 picoxystrobin  3:10 0.03 + 0.1  X.04 picoxystrobin  1:10 0.03 + 0.3  X.04 sulphur 1:1 0.1 + 0.1 X.04 sulphur 1:3 0.1 + 0.3 X.04 sulphur  3:10 0.03 + 0.1  X.04 sulphur  1:10 0.03 + 0.3  X.04 tebuconazole 1:1 0.1 + 0.1 X.04 tebuconazole 1:3 0.1 + 0.3 X.04 tebuconazole  1:10 0.03 + 0.3  X.04 prothioconazole 1:1 0.1 + 0.1 X.04 prothioconazole 1:3 0.1 + 0.3 X.04 prothioconazole  3:10 0.03 + 0.1  X.04 prothioconazole  1:10 0.03 + 0.3  X.04 fluopyram 1:1 0.1 + 0.1 X.04 fluopyram 1:3 0.1 + 0.3 X.04 fluopyram  3:10 0.03 + 0.1  X.04 fluopyram  1:10 0.03 + 0.3  X.04 copper oxychloride 1:1 0.1 + 0.1 X.04 copper oxychloride 1:3 0.1 + 0.3 X.04 copper oxychloride  3:10 0.03 + 0.1  X.04 copper oxychloride  1:10 0.03 + 0.3  X.04 benzovindiflupyr 1:1 0.1 + 0.1 X.04 benzovindiflupyr 1:3 0.1 + 0.3 X.04 benzovindiflupyr  3:10 0.03 + 0.1  X.04 benzovindiflupyr  1:10 0.03 + 0.3  X.04 isopyrazam 1:1 0.1 + 0.1 X.04 isopyrazam 1:3 0.1 + 0.3 X.04 isopyrazam  3:10 0.03 + 0.1  X.04 isopyrazam  1:10 0.03 + 0.3  X.04 pydiflumetofen 1:1 0.1 + 0.1 X.04 pydiflumetofen 1:3 0.1 + 0.3 X.04 pydiflumetofen  3:10 0.03 + 0.1  X.04 pydiflumetofen  1:10 0.03 + 0.3  X.04 fluxapyroxad 1:1 0.1 + 0.1 X.04 fluxapyroxad 1:3 0.1 + 0.3 X.04 fluxapyroxad  3:10 0.03 + 0.1  X.04 fluxapyroxad  1:10 0.03 + 0.3  X.04 quinofumelin 1:1 0.1 + 0.1 X.04 quinofumelin 1:3 0.1 + 0.3 X.04 quinofumelin  3:10 0.03 + 0.1  X.04 quinofumelin  1:10 0.03 + 0.3  X.04 isoflucypram 1:1 0.1 + 0.1 X.04 isoflucypram 1:3 0.1 + 0.3 X.04 isoflucypram  3:10 0.03 + 0.1  X.04 isoflucypram  1:10 0.03 + 0.3  X.04 mefentrifluconazole 1:1 0.1 + 0.1 X.04 mefentrifluconazole 1:3 0.1 + 0.3 X.04 mefentrifluconazole  3:10 0.03 + 0.1  X.04 mefentrifluconazole  1:10 0.03 + 0.3  X.04 ipflufenoquin 1:1 0.1 + 0.1 X.04 ipflufenoquin 1:3 0.1 + 0.3 X.04 ipflufenoquin  3:10 0.03 + 0.1  X.04 ipflufenoquin  1:10 0.03 + 0.3  X.04 metyltetraprole 1:1 0.1 + 0.1 X.04 metyltetraprole 1:3 0.1 + 0.3 X.04 metyltetraprole  3:10 0.03 + 0.1  X.04 metyltetraprole  1:10 0.03 + 0.3  X.04 aminopyrifen 1:1 0.1 + 0.1 X.04 aminopyrifen 1:3 0.1 + 0.3 X.04 aminopyrifen  3:10 0.03 + 0.1  X.04 aminopyrifen  1:10 0.03 + 0.3  X.04 florylpicoxamid 1:1 0.1 + 0.1 X.04 florylpicoxamid 1:3 0.1 + 0.3 X.04 florylpicoxamid  3:10 0.03 + 0.1  X.04 florylpicoxamid  1:10 0.03 + 0.3  X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]- 1:1 0.1 + 0.1 1-(1,2,4-triazol-1-yl)propan-2-ol X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]- 1:3 0.1 + 0.3 1-(1,2,4-triazol-1-yl)propan-2-ol X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-  3:10 0.03 + 0.1  1-(1,2,4-triazol-1-yl)propan-2-ol X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-  1:10 0.03 + 0.3  1-(1,2,4-triazol-1-yl)propan-2-ol X.04 fenpicoxamid 1:1 0.1 + 0.1 X.04 fenpicoxamid 1:3 0.1 + 0.3 X.04 fenpicoxamid  3:10 0.03 + 0.1  X.04 fenpicoxamid  1:10 0.03 + 0.3  X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:1 0.1 + 0.1 methoxyimino-N,3-dimethyl-pent-3-enamide X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:3 0.1 + 0.3 methoxyimino-N,3-dimethyl-pent-3-enamide X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  3:10 0.03 + 0.1  methoxyimino-N,3-dimethyl-pent-3-enamide X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  1:10 0.03 + 0.3  methoxyimino-N,3-dimethyl-pent-3-enamide X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:3   0.2 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate[(1S,2S)-1 -methyl-2-(o- tolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy- pyridine-2-carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 5:3  0.1 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 5:6 0.05 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-  5:12 0.025 + 0.06  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-  5:24 0.0125 + 0.06  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-  5:48 0.00625 + 0.06   methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 20:3   0.2 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:3   0.1 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:6  0.05 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:12 0.025 + 0.03  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:24 0.0125 + 0.03  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:48 0.00625 + 0.03   methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4- .sup. 1 :100 0.2 + 20  oxadiazol-3-yl]benzamideN-(2-fluorophenyl)-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:200 0.1 + 20  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:400 0.05 + 20.sup.  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:800 0.025 + 20   oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:50 0.2 + 10  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:100 0.1 + 10  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:200 0.05 + 10.sup.  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:400 0.025 + 10   oxadiazol-3-yl]benzamide X.04 Florylpicoxamid 10:1   0.2 + 0.02 X.04 Florylpicoxamid 5:1  0.1 + 0.02 X.04 Florylpicoxamid 5:2 0.05 + 0.02 X.04 Florylpicoxamid 5:4 0.025 + 0.02  X.04 Florylpicoxamid 5:8 0.0125 + 0.02  X.04 Florylpicoxamid  5:16 0.006125 + 0.02   X.04 Florylpicoxamid 20:1   0.2 + 0.01 X.04 Florylpicoxamid 10:1   0.1 + 0.01 X.04 Florylpicoxamid 5:1 0.05 + 0.01 X.04 Florylpicoxamid 5:2 0.025 + 0.01  X.04 Florylpicoxamid 5:4 0.0125 + 0.01  X.04 Florylpicoxamid 5:8 0.006125 + 0.01  

[0245] The following mixture compositions at the reported concentration (in ppm) in tables C1-3 and C1-4 gave the following disease control in this test Mycosphaerella arachidis syn. Cercospora arachidicola (Brown leaf spot of peanut). Fungicidal activity was evaluated on a 100-0 scale (100=no disease growth; 0=well completely covered by mycelium).

TABLE-US-00014 TABLE C1-3 Conc. COLBY (ppm) Ratio Activity (expected Component A Component B (A:B) A:B (%) activity %) X.02  0.03 50 chlorothalonil 0.1 20 X.02 chlorothalonil 0.03 + 0.1 3:10 70 60 mancozeb 0.1 0 mancozeb 0.3 0 X.02 mancozeb 0.03 + 0.1 3:10 70 50 X.02 mancozeb 0.03 + 0.3 1:10 70 50 folpet 0.3 20 X.02 folpet 0.03 + 0.3 1:10 70 60 ipflufenoquin 0.3 0 X.02 ipflufenoquin 0.03 + 0.3 1:10 70 50

TABLE-US-00015 TABLE C1-4 Conc. COLBY (ppm) Ratio Activity (expected Component A Component B (A:B) A:B (%) activity %) X.04 0.0125 50 X.04 0.00625 0 [(1S,2S)-1-methyl-2-(o- 0.03 70 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-  0.0125 + 0.03 12:5  100 85 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o- 0.00625 + 0.03 24:5  100 70 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate Florylpicoxamid 0.02 90 Florylpicoxamid 0.01 50 X.04 Florylpicoxamid  0.0125 + 0.02 5:8 100 95 X.04 Florylpicoxamid 0.00625 + 0.02  5:16 100 90 X.04 Florylpicoxamid  0.0125 + 0.01 5:4 100 75 X.04 Florylpicoxamid 0.00625 + 0.01 5:8 100 50 X.02 0.03125 70 X.02 Florylpicoxamid 0.03125 + 0.02 25:16 100 97 X.02 Florylpicoxamid 0.03125 + 0.01 25:8  100 85

Example C2—Fungicidal Activity Against Septoria tritici (Leaf Blotch)

[0246] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically after 72 hrs. The following compound mixtures gave at least 80% control Septoria tritici at rates cited in the table when compared to untreated control under the same conditions, which showed extensive disease development.

TABLE-US-00016 TABLE C2-1 Fungicidal activity >80% (% of untreated) against Septoria tritici Conc. Ratio (ppm) Component A Component B A:B (A:B) X.02 chlorothalonil 1:1 0.1 + 0.1 X.02 chlorothalonil 1:3 0.1 + 0.3 X.02 chlorothalonil  1:10 0.03 + 0.3  X.02 propiconazole 1:3 0.1 + 0.3 X.02 propiconazole  1:10 0.03 + 0.3  X.02 hexaconazole 1:1 0.1 + 0.1 X.02 hexaconazole 1:3 0.1 + 0.3 X.02 hexaconazole  3:10 0.03 + 0.1  X.02 hexaconazole  1:10 0.03 + 0.3  X.02 difenoconazole 1:1 0.1 + 0.1 X.02 difenoconazole 1:3 0.1 + 0.3 X.02 difenoconazole  3:10 0.03 + 0.1  X.02 difenoconazole  1:10 0.03 + 0.3  X.02 cyproconazole 1:3 0.1 + 0.3 X.02 trifloxystrobin 1:1 0.1 + 0.1 X.02 trifloxystrobin 1:3 0.1 + 0.3 X.02 trifloxystrobin  3:10 0.03 + 0.1  X.02 trifloxystrobin  1:10 0.03 + 0.3  X.02 azoxystrobin 1:1 0.1 + 0.1 X.02 azoxystrobin 1:3 0.1 + 0.3 X.02 azoxystrobin  3:10 0.03 + 0.1  X.02 azoxystrobin  1:10 0.03 + 0.3  X.02 pyraclostrobin 1:1 0.1 + 0.1 X.02 pyraclostrobin 1:3 0.1 + 0.3 X.02 pyraclostrobin  3:10 0.03 + 0.1  X.02 pyraclostrobin  1:10 0.03 + 0.3  X.02 picoxystrobin 1:1 0.1 + 0.1 X.02 picoxystrobin 1:3 0.1 + 0.3 X.02 picoxystrobin  3:10 0.03 + 0.1  X.02 picoxystrobin  1:10 0.03 + 0.3  X.02 prothioconazole 1:1 0.1 + 0.1 X.02 prothioconazole 1:3 0.1 + 0.3 X.02 prothioconazole  3:10 0.03 + 0.1  X.02 prothioconazole  1:10 0.03 + 0.3  X.02 benzovindiflupyr 1:1 0.1 + 0.1 X.02 benzovindiflupyr 1:3 0.1 + 0.3 X.02 benzovindiflupyr  1:10 0.03 + 0.3  X.02 isopyrazam 1:1 0.1 + 0.1 X.02 isopyrazam 1:3 0.1 + 0.3 X.02 isopyrazam  1:10 0.03 + 0.3  X.02 pydiflumetofen 1:1 0.1 + 0.1 X.02 pydiflumetofen 1:3 0.1 + 0.3 X.02 pydiflumetofen  3:10 0.03 + 0.1  X.02 pydiflumetofen  1:10 0.03 + 0.3  X.02 fluxapyroxad 1:1 0.1 + 0.1 X.02 fluxapyroxad 1:3 0.1 + 0.3 X.02 fluxapyroxad  1:10 0.03 + 0.3  X.02 quinofumelin 1:3 0.1 + 0.3 X.02 isoflucypram 1:1 0.1 + 0.1 X.02 isoflucypram 1:3 0.1 + 0.3 X.02 isoflucypram  3:10 0.03 + 0.1  X.02 isoflucypram  1:10 0.03 + 0.3  X.02 mefentrifluconazole 1:1 0.1 + 0.1 X.02 mefentrifluconazole 1:3 0.1 + 0.3 X.02 mefentrifluconazole  3:10 0.03 + 0.1  X.02 mefentrifluconazole  1:10 0.03 + 0.3  X.02 ipflufenoquin 1:1 0.1 + 0.1 X.02 ipflufenoquin 1:3 0.1 + 0.3 X.02 metyltetraprole 1:1 0.1 + 0.1 X.02 metyltetraprole 1:3 0.1 + 0.3 X.02 metyltetraprole  3:10 0.03 + 0.1  X.02 metyltetraprole  1:10 0.03 + 0.3  X.02 aminopyrifen 1:1 0.1 + 0.1 X.02 aminopyrifen 1:3 0.1 + 0.3 X.02 aminopyrifen  3:10 0.03 + 0.1  X.02 aminopyrifen  1:10 0.03 + 0.3  X.02 florylpicoxamid 1:1 0.1 + 0.1 X.02 florylpicoxamid 1:3 0.1 + 0.3 X.02 florylpicoxamid  3:10 0.03 + 0.1  X.02 florylpicoxamid  1:10 0.03 + 0.3  X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1- 1:1 0.1 + 0.1 (1,2,4-triazol-1-yl)propan-2-ol X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1- 1:3 0.1 + 0.3 (1,2,4-triazol-1-yl)propan-2-ol X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-  3:10 0.03 + 0.1  (1,2,4-triazol-1-yl)propan-2-ol X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-  1:10 0.03 + 0.3  (1,2,4-triazol-1-yl)propan-2-ol X.02 fenpicoxamid 1:1 0.1 + 0.1 X.02 fenpicoxamid 1:3 0.1 + 0.3 X.02 fenpicoxamid  3:10 0.03 + 0.1  X.02 fenpicoxamid  1:10 0.03 + 0.3  X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:1 0.1 + 0.1 methoxyimino-N,3-dimethyl-pent-3-enamide X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:3 0.1 + 0.3 methoxyimino-N,3-dimethyl-pent-3-enamide X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  3:10 0.03 + 0.1  methoxyimino-N,3-dimethyl-pent-3-enamide X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  1:10 0.03 + 0.3  methoxyimino-N,3-dimethyl-pent-3-enamide X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 50:3    1 + 0.06 3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 25:3   0.5 + 0.06 3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 25:6  0.25 + 0.06 3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 25:12 0.125 + 0.06  3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 25:24 0.0625 + 0.06  3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 25:48 0.03125 + 0.06   3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 100:3    1 + 0.03 3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 50:3   0.5 + 0.03 3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 50:6  0.25 + 0.03 3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 50:12 0.125 + 0.03  3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 50:24 0.0625 + 0.03  3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 50:48 0.03125 + 0.03   3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:20  1 + 20 oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:40 0.5 + 20  oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:80 0.25 + 20.sup.  oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:160 0.125 + 20   oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:10  1 + 10 oxadiazol-3-yl] benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:20 0.5 + 10  oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:40 0.25 + 10.sup.  oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:80 0.125 + 10   oxadiazol-3-yl]benzamide X.02 Florylpicoxamid 50:1    1 + 0.02 X.02 Florylpicoxamid 25:1   0.5 + 0.02 X.02 Florylpicoxamid 25:2  0.25 + 0.02 X.02 Florylpicoxamid 25:4  0.125 + 0.02  X.02 Florylpicoxamid 25:8  0.0625 + 0.02  X.02 Florylpicoxamid 25:16 0.03125 + 0.02   X.02 Florylpicoxamid 100:1    1 + 0.01 X.02 Florylpicoxamid 50:1   0.5 + 0.01 X.02 Florylpicoxamid 25:1  0.25 + 0.01 X.02 Florylpicoxamid 25:2  0.125 + 0.01  X.02 Florylpicoxamid 25:4  0.0625 + 0.01  X.02 Florylpicoxamid 25:8  0.03125 + 0.01  

TABLE-US-00017 TABLE C2-2 Fungicidal activity >80% (% of untreated) against Septoria tritici Conc. Ratio (ppm) Component A Component B A:B (A:B) X.04 chlorothalonil 1:1 0.1 + 0.1 X.04 chlorothalonil 1:3 0.1 + 0.3 X.04 chlorothalonil  1:10 0.03 + 0.3  X.04 propiconazole 1:3 0.1 + 0.3 X.04 propiconazole  1:10 0.03 + 0.3  X.04 hexaconazole 1:1 0.1 + 0.1 X.04 hexaconazole 1:3 0.1 + 0.3 X.04 hexaconazole  3:10 0.03 + 0.1  X.04 hexaconazole  1:10 0.03 + 0.3  X.04 difenoconazole 1:1 0.1 + 0.1 X.04 difenoconazole 1:3 0.1 + 0.3 X.04 difenoconazole  3:10 0.03 + 0.1  X.04 difenoconazole  1:10 0.03 + 0.3  X.04 fludioxonil 1:3 0.1 + 0.3 X.04 cyproconazole 1:3 0.1 + 0.3 X.04 cyproconazole  1:10 0.03 + 0.3  X.04 trifloxystrobin 1:1 0.1 + 0.1 X.04 trifloxystrobin 1:3 0.1 + 0.3 X.04 trifloxystrobin  3:10 0.03 + 0.1  X.04 trifloxystrobin  1:10 0.03 + 0.3  X.04 folpet 1:3 0.1 + 0.3 X.04 azoxystrobin 1:1 0.1 + 0.1 X.04 azoxystrobin 1:3 0.1 + 0.3 X.04 azoxystrobin  3:10 0.03 + 0.1  X.04 azoxystrobin  1:10 0.03 + 0.3  X.04 pyraclostrobin 1:1 0.1 + 0.1 X.04 pyraclostrobin 1:3 0.1 + 0.3 X.04 pyraclostrobin  3:10 0.03 + 0.1  X.04 pyraclostrobin  1:10 0.03 + 0.3  X.04 picoxystrobin 1:1 0.1 + 0.1 X.04 picoxystrobin 1:3 0.1 + 0.3 X.04 picoxystrobin  3:10 0.03 + 0.1  X.04 picoxystrobin  1:10 0.03 + 0.3  X.04 prothioconazole 1:1 0.1 + 0.1 X.04 prothioconazole 1:3 0.1 + 0.3 X.04 prothioconazole  3:10 0.03 + 0.1  X.04 prothioconazole  1:10 0.03 + 0.3  X.04 fluopyram 1:3 0.1 + 0.3 X.04 benzovindiflupyr 1:1 0.1 + 0.1 X.04 benzovindiflupyr 1:3 0.1 + 0.3 X.04 benzovindiflupyr  1:10 0.03 + 0.3  X.04 isopyrazam 1:1 0.1 + 0.1 X.04 isopyrazam 1:3 0.1 + 0.3 X.04 isopyrazam  1:10 0.03 + 0.3  X.04 pydiflumetofen 1:1 0.1 + 0.1 X.04 pydiflumetofen 1:3 0.1 + 0.3 X.04 pydiflumetofen  3:10 0.03 + 0.1  X.04 pydiflumetofen  1:10 0.03 + 0.3  X.04 fluxapyroxad 1:1 0.1 + 0.1 X.04 fluxapyroxad 1:3 0.1 + 0.3 X.04 fluxapyroxad  1:10 0.03 + 0.3  X.04 quinofumelin 1:3 0.1 + 0.3 X.04 isoflucypram 1:1 0.1 + 0.1 X.04 isoflucypram 1:3 0.1 + 0.3 X.04 isoflucypram  3:10 0.03 + 0.1  X.04 isoflucypram  1:10 0.03 + 0.3  X.04 mefentrifluconazole 1:1 0.1 + 0.1 X.04 mefentrifluconazole 1:3 0.1 + 0.3 X.04 mefentrifluconazole  3:10 0.03 + 0.1  X.04 mefentrifluconazole  1:10 0.03 + 0.3  X.04 ipflufenoquin 1:1 0.1 + 0.1 X.04 ipflufenoquin 1:3 0.1 + 0.3 X.04 ipflufenoquin  1:10 0.03 + 0.3  X.04 metyltetraprole 1:1 0.1 + 0.1 X.04 metyltetraprole 1:3 0.1 + 0.3 X.04 metyltetraprole  3:10 0.03 + 0.1  X.04 metyltetraprole  1:10 0.03 + 0.3  X.04 aminopyrifen 1:1 0.1 + 0.1 X.04 aminopyrifen 1:3 0.1 + 0.3 X.04 aminopyrifen  3:10 0.03 + 0.1  X.04 aminopyrifen  1:10 0.03 + 0.3  X.04 florylpicoxamid 1:1 0.1 + 0.1 X.04 florylpicoxamid 1:3 0.1 + 0.3 X.04 florylpicoxamid  3:10 0.03 + 0.1  X.04 florylpicoxamid  1:10 0.03 + 0.3  X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]- 1:1 0.1 + 0.1 1-(1,2,4-triazol-1-yl)propan-2-ol X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]- 1:3 0.1 + 0.3 1-(1,2,4-triazol-1-yl)propan-2-ol X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-  3:10 0.03 + 0.1  1-(1,2,4-triazol-1-yl)propan-2-ol X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-  1:10 0.03 + 0.3  1-(1,2,4-triazol-1-yl)propan-2-ol X.04 fenpicoxamid 1:1 0.1 + 0.1 X.04 fenpicoxamid 1:3 0.1 + 0.3 X.04 fenpicoxamid  3:10 0.03 + 0.1  X.04 fenpicoxamid  1:10 0.03 + 0.3  X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:1 0.1 + 0.1 methoxyimino-N,3-dimethyl-pent-3-enamide X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:3 0.1 + 0.3 methoxyimino-N,3-dimethyl-pent-3-enamide X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  3:10 0.03 + 0.1  methoxyimino-N,3-dimethyl-pent-3-enamide X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  1:10 0.03 + 0.3  methoxyimino-N,3-dimethyl-pent-3-enamide X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:3   0.2 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 5:3  0.1 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 5:6 0.05 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-  5:12 0.025 + 0.06  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-  5:24 0.0125 + 0.06  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-  5:48 0.00625 + 0.06   methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 20:3   0.2 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:3   0.1 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:6  0.05 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:12 0.025 + 0.03  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:24 0.0125 + 0.03  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:48 0.00625 + 0.03   methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:100 0.2 + 20  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:200 0.1 + 20  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:400 0.05 + 20.sup.  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:800 0.025 + 20   oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:50 0.2 + 10  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:100 0.1 + 10  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:200 0.05 + 10.sup.  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:400 0.025 + 10   oxadiazol-3-yl]benzamide X.04 Florylpicoxamid 10:1   0.2 + 0.02 X.04 Florylpicoxamid 5:1  0.1 + 0.02 X.04 Florylpicoxamid 5:2 0.05 + 0.02 X.04 Florylpicoxamid 5:4 0.025 + 0.02  X.04 Florylpicoxamid 5:8 0.0125 + 0.02  X.04 Florylpicoxamid  5:16 0.006125 + 0.02   X.04 Florylpicoxamid 20:1   0.2 + 0.01 X.04 Florylpicoxamid 10:1   0.1 + 0.01 X.04 Florylpicoxamid 5:1 0.05 + 0.01 X.04 Florylpicoxamid 5:2 0.025 + 0.01 

[0247] The following mixture compositions at the reported concentration (in ppm) in tables C2-3 to C2-5 gave the following disease control in this test Septoria tritici (leaf blotch). Fungicidal activity was evaluated on a 100-0 scale (100=no disease growth; 0=well completely covered by mycelium).

TABLE-US-00018 TABLE C2-3 Conc. COLBY (ppm) Ratio Activity (expected Component A Component B (A:B) A:B (%) activity %) X.02 0.1 70 X.02  0.03 0 chlorothalonil 0.1 20 chlorothalonil 0.3 50 X.02 chlorothalonil 0.1 + 0.1 1:1 90 76 X.02 chlorothalonil 0.1 + 0.3 1:3 100 85 X.02 chlorothalonil 0.03 + 0.3   1:10 90 50 propiconazole 0.3 70 X.02 propiconazole 0.03 + 0.3   1:10 90 70 hexaconazole 0.1 70 X.02 hexaconazole 0.1 + 0.1 1:1 100 91 X.02 hexaconazole 0.03 + 0.1   3:10 90 70 cyproconazole 0.3 50 X.02 cyproconazole 0.1 + 0.3 1:3 90 85 X.02 cyproconazole 0.03 + 0.3   1:10 70 50 benzovindiflupyr 0.1 50 benzovindiflupyr 0.3 70 X.02 benzovindiflupyr 0.1 + 0.1 1:1 90 85 X.02 benzovindiflupyr 0.1 + 0.3 1:3 100 91 X.02 benzovindiflupyr 0.03 + 0.3   1:10 90 70 isopyrazam 0.1 50 isopyrazam 0.3 70 X.02 isopyrazam 0.1 + 0.1 1:1 90 85 X.02 isopyrazam 0.1 + 0.3 1:3 100 91 X.02 isopyrazam 0.03 + 0.3   1:10 90 70 quinofumelin 0.3 0 X.02 quinofumelin 0.1 + 0.3 1:3 90 70 ipflufenoquin 0.1 20 ipflufenoquin 0.3 20 X.02 ipflufenoquin 0.1 + 0.1 1:1 90 76 X.02 ipflufenoquin 0.1 + 0.3 1:3 100 76 X.02 ipflufenoquin 0.03 + 0.3   1:10 50 20

TABLE-US-00019 TABLE C2-4 Conc. COLBY (ppm) Ratio Activity (expected Component A Component B (A:B) A:B (%) activity %) X.04 0.1 70 X.04 0.03 50 chlorothalonil 0.1 20 chlorothalonil 0.3 50 X.04 chlorothalonil 0.1 + 0.1 1:1 100 76 X.04 chlorothalonil 0.1 + 0.3 1:3 100 85 X.04 chlorothalonil 0.03 + 0.1   3:10 70 60 X.04 chlorothalonil 0.03 + 0.3   1:10 100 75 propiconazole 0.3 70 X.04 propiconazole 0.1 + 0.3 1:3 100 91 X.04 propiconazole 0.03 + 0.3   1:10 100 85 hexaconazole 0.1 70 X.04 hexaconazole 0.1 + 0.1 1:1 100 91 X.04 hexaconazole 0.03 + 0.1   3:10 100 85 fludioxonil 0.3 20 X.04 fludioxonil 0.1 + 0.3 1:3 90 76 X.04 fludioxonil 0.03 + 0.3   1:10 70 60 cyproconazole 0.3 50 X.04 cyproconazole 0.1 + 0.3 1:3 90 85 X.04 cyproconazole 0.03 + 0.3   1:10 90 75 folpet 0.3 20 X.04 folpet 0.1 + 0.3 1:3 90 76 quinofumelin 0.3 0 X.04 quinofumelin 0.1 + 0.3 1:3 90 70 X.04 quinofumelin 0.03 + 0.3   1:10 70 50 ipflufenoquin 0.1 20 ipflufenoquin 0.3 20 X.04 ipflufenoquin 0.1 + 0.1 1:1 90 76 X.04 ipflufenoquin 0.1 + 0.3 1:3 100 76 X.04 ipflufenoquin 0.03 + 0.1   3:10 70 60 X.04 ipflufenoquin 0.03 + 0.3   1:10 90 60

TABLE-US-00020 TABLE C2-5 Conc. COLBY (ppm) Ratio Activity (expected Component A Component B (A:B) A:B (%) activity %) X.02 0.0625 90 X.02 0.03125 20 [(1S,2S)-1-methyl-2-(o- 0.06 70 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate [(1S,2S)-1-methyl-2-(o- 0.03 50 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o- 0.0625 + 0.06 25:24 100 97 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o- 0.03125 + 0.06  50:24 100 76 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o- 0.0625 + 0.03 50:24 100 95 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o- 0.03125 + 0.03  25:24 100 60 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.02 Florylpicoxamid 0.0625 + 0.02 25:8  100 99 X.02 Florylpicoxamid 0.03125 + 0.02  25:16 100 92 X.02 Florylpicoxamid 0.0625 + 0.01 25:4  100 97 X.02 Florylpicoxamid 0.03125 + 0.01  25:8  90 76 X.04 0.025 70 X.04 0.0125 20 X.04 0.00625 0 X.04 [(1S,2S)-1-methyl-2-(o-  0.025 + 0.06  5:12 100 91 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o- 0.0125 + 0.06  5:24 100 76 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o- 0.00625 + 0.06   5:48 90 70 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-  0.025 + 0.03 10:12 100 85 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o- 0.0125 + 0.03 10:24 90 60 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o- 0.00625 + 0.03  10:48 70 50 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate N-(2-fluorophenyl)-4-[5- 20 0 (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide N-(2-fluorophenyl)-4-[5- 10 0 (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-  0.025 + 20  1:800 90 70 (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-  0.025 + 10  1:400 90 70 (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide Florylpicoxamid 0.02 90 Florylpicoxamid 0.01 70 X.04 Florylpicoxamid  0.025 + 0.02 5:4 100 97 X.04 Florylpicoxamid 0.0125 + 0.02 5:8 90 92 X.04 Florylpicoxamid 0.006125 + 0.02   5:16 90 90 X.04 Florylpicoxamid  0.025 + 0.01 5:2 100 91

Example C3—Fungicidal Activity Against Septoria glycines (Brown Spot)

[0248] Conidia of the fungus harvested from a fresh culture grown on artificial media, were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically after 72 hrs.

[0249] The following compound mixtures gave at least 80% control Septoria glycines at rates cited in the table when compared to untreated control under the same conditions, which showed extensive disease development:

TABLE-US-00021 TABLE C3-1 Fungicidal activity >80% (% of untreated) against Septoria glycines Conc. Ratio (ppm) Component A Component B A:B (A:B) X.02 chlorothalonil 1:1 0.1 + 0.1 X.02 chlorothalonil 1:3 0.1 + 0.3 X.02 chlorothalonil  1:10 0.03 + 0.3  X.02 mancozeb 1:1 0.1 + 0.1 X.02 mancozeb 1:3 0.1 + 0.3 X.02 propiconazole 1:1 0.1 + 0.1 X.02 propiconazole 1:3 0.1 + 0.3 X.02 propiconazole  3:10 0.03 + 0.1  X.02 propiconazole  1:10 0.03 + 0.3  X.02 fenpropimorph 1:1 0.1 + 0.1 X.02 fenpropimorph 1:3 0.1 + 0.3 X.02 fenpropimorph  3:10 0.03 + 0.1  X.02 fenpropimorph  1:10 0.03 + 0.3  X.02 fenpropidin 1:1 0.1 + 0.1 X.02 fenpropidin 1:3 0.1 + 0.3 X.02 hexaconazole 1:1 0.1 + 0.1 X.02 hexaconazole 1:3 0.1 + 0.3 X.02 hexaconazole  3:10 0.03 + 0.1  X.02 hexaconazole  1:10 0.03 + 0.3  X.02 paclobutrazol 1:1 0.1 + 0.1 X.02 paclobutrazol 1:3 0.1 + 0.3 X.02 trinexapac-ethyl 1:3 0.1 + 0.3 X.02 flutriafol 1:1 0.1 + 0.1 X.02 flutriafol 1:3 0.1 + 0.3 X.02 flutriafol  1:10 0.03 + 0.3  X.02 difenoconazole 1:1 0.1 + 0.1 X.02 difenoconazole 1:3 0.1 + 0.3 X.02 difenoconazole  3:10 0.03 + 0.1  X.02 difenoconazole  1:10 0.03 + 0.3  X.02 fludioxonil 1:1 0.1 + 0.1 X.02 fludioxonil 1:3 0.1 + 0.3 X.02 cyproconazole 1:1 0.1 + 0.1 X.02 cyproconazole 1:3 0.1 + 0.3 X.02 cyproconazole  1:10 0.03 + 0.3  X.02 trifloxystrobin 1:1 0.1 + 0.1 X.02 trifloxystrobin 1:3 0.1 + 0.3 X.02 trifloxystrobin  3:10 0.03 + 0.1  X.02 trifloxystrobin  1:10 0.03 + 0.3  X.02 folpet 1:1 0.1 + 0.1 X.02 folpet 1:3 0.1 + 0.3 X.02 azoxystrobin 1:1 0.1 + 0.1 X.02 azoxystrobin 1:3 0.1 + 0.3 X.02 azoxystrobin  3:10 0.03 + 0.1  X.02 azoxystrobin  1:10 0.03 + 0.3  X.02 pyraclostrobin 1:1 0.1 + 0.1 X.02 pyraclostrobin 1:3 0.1 + 0.3 X.02 pyraclostrobin  3:10 0.03 + 0.1  X.02 pyraclostrobin  1:10 0.03 + 0.3  X.02 picoxystrobin 1:1 0.1 + 0.1 X.02 picoxystrobin 1:3 0.1 + 0.3 X.02 picoxystrobin  3:10 0.03 + 0.1  X.02 picoxystrobin  1:10 0.03 + 0.3  X.02 sulphur 1:3 0.1 + 0.3 X.02 tebuconazole 1:1 0.1 + 0.1 X.02 tebuconazole 1:3 0.1 + 0.3 X.02 tebuconazole  3:10 0.03 + 0.1  X.02 tebuconazole  1:10 0.03 + 0.3  X.02 prothioconazole 1:1 0.1 + 0.1 X.02 prothioconazole 1:3 0.1 + 0.3 X.02 prothioconazole  3:10 0.03 + 0.1  X.02 prothioconazole  1:10 0.03 + 0.3  X.02 fluopyram 1:1 0.1 + 0.1 X.02 fluopyram 1:3 0.1 + 0.3 X.02 benzovindiflupyr 1:1 0.1 + 0.1 X.02 benzovindiflupyr 1:3 0.1 + 0.3 X.02 benzovindiflupyr  3:10 0.03 + 0.1  X.02 benzovindiflupyr  1:10 0.03 + 0.3  X.02 isopyrazam 1:1 0.1 + 0.1 X.02 isopyrazam 1:3 0.1 + 0.3 X.02 isopyrazam  3:10 0.03 + 0.1  X.02 isopyrazam  1:10 0.03 + 0.3  X.02 pydiflumetofen 1:1 0.1 + 0.1 X.02 pydiflumetofen 1:3 0.1 + 0.3 X.02 pydiflumetofen  3:10 0.03 + 0.1  X.02 pydiflumetofen  1:10 0.03 + 0.3  X.02 fluxapyroxad 1:1 0.1 + 0.1 X.02 fluxapyroxad 1:3 0.1 + 0.3 X.02 fluxapyroxad  3:10 0.03 + 0.1  X.02 fluxapyroxad  1:10 0.03 + 0.3  X.02 isoflucypram 1:1 0.1 + 0.1 X.02 isoflucypram 1:3 0.1 + 0.3 X.02 isoflucypram  3:10 0.03 + 0.1  X.02 isoflucypram  1:10 0.03 + 0.3  X.02 mefentrifluconazole 1:1 0.1 + 0.1 X.02 mefentrifluconazole 1:3 0.1 + 0.3 X.02 mefentrifluconazole  3:10 0.03 + 0.1  X.02 mefentrifluconazole  1:10 0.03 + 0.3  X.02 ipflufenoquin 1:1 0.1 + 0.1 X.02 ipflufenoquin 1:3 0.1 + 0.3 X.02 ipflufenoquin  3:10 0.03 + 0.1  X.02 ipflufenoquin  1:10 0.03 + 0.3  X.02 metyltetraprole 1:1 0.1 + 0.1 X.02 metyltetraprole 1:3 0.1 + 0.3 X.02 metyltetraprole  3:10 0.03 + 0.1  X.02 metyltetraprole  1:10 0.03 + 0.3  X.02 aminopyrifen 1:1 0.1 + 0.1 X.02 aminopyrifen 1:3 0.1 + 0.3 X.02 aminopyrifen  3:10 0.03 + 0.1  X.02 aminopyrifen  1:10 0.03 + 0.3  X.02 florylpicoxamid 1:1 0.1 + 0.1 X.02 florylpicoxamid 1:3 0.1 + 0.3 X.02 florylpicoxamid  3:10 0.03 + 0.1  X.02 florylpicoxamid  1:10 0.03 + 0.3  X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]- 1:1 0.1 + 0.1 1-(1,2,4-triazol-1-yl)propan-2-ol X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]- 1:3 0.1 + 0.3 1-(1,2,4-triazol-1-yl)propan-2-ol X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-  3:10 0.03 + 0.1  1-(1,2,4-triazol-1-yl)propan-2-ol X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-  1:10 0.03 + 0.3  1-(1,2,4-triazol-1-yl)propan-2-ol X.02 fenpicoxamid 1:1 0.1 + 0.1 X.02 fenpicoxamid 1:3 0.1 + 0.3 X.02 fenpicoxamid  3:10 0.03 + 0.1  X.02 fenpicoxamid  1:10 0.03 + 0.3  X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:1 0.1 + 0.1 methoxyimino-N,3-dimethyl-pent-3-enamide X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:3 0.1 + 0.3 methoxyimino-N,3-dimethyl-pent-3-enamide X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  3:10 0.03 + 0.1  methoxyimino-N,3-dimethyl-pent-3-enamide X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  1:10 0.03 + 0.3  methoxyimino-N,3-dimethyl-pent-3-enamide X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 50:3    1 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 25:3   0.5 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 25:6  0.25 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 25:12 0.125 + 0.06  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 25:24 0.0625 + 0.06  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 25:48 0.03125 + 0.06   methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 100:3    1 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 50:3   0.5 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 50:6  0.25 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1 S,2S)-1 -methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 50:12 0.125 + 0.03  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 50:24 0.0625 + 0.03  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 50:48 0.03125 + 0.03   methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:20  1 + 20 oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:40 0.5 + 20  oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:80 0.25 + 20.sup.  oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:160 0.125 + 20   oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:320 0.0625 + 20    oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:10  1 + 10 oxadiazol-3-yl] benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:20 0.5 + 10  oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:40 0.25 + 10.sup.  oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:80 0.125 + 10   oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:160 0.0625 + 10    oxadiazol-3-yl]benzamide X.02 Florylpicoxamid 50:1    1 + 0.02 X.02 Florylpicoxamid 25:1   0.5 + 0.02 X.02 Florylpicoxamid 25:2  0.25 + 0.02 X.02 Florylpicoxamid 25:4  0.125 + 0.02  X.02 Florylpicoxamid 25:8  0.0625 + 0.02  X.02 Florylpicoxamid 25:16 0.03125 + 0.02   X.02 Florylpicoxamid 100:1    1 + 0.01 X.02 Florylpicoxamid 50:1   0.5 + 0.01 X.02 Florylpicoxamid 25:1  0.25 + 0.01 X.02 Florylpicoxamid 25:2  0.125 + 0.01  X.02 Florylpicoxamid 25:4  0.0625 + 0.01  X.02 Florylpicoxamid 25:8  0.03125 + 0.01  

TABLE-US-00022 TABLE C3-2 Fungicidal activity >80% (% of untreated) against Septoria glycines Conc. Ratio (ppm) Component A Component B A:B (A:B) X.04 glyphosate 1:1 0.1 + 0.1 X.04 glyphosate 1:3 0.1 + 0.3 X.04 chlorothalonil 1:1 0.1 + 0.1 X.04 chlorothalonil 1:3 0.1 + 0.3 X.04 chlorothalonil  1:10 0.03 + 0.3  X.04 mancozeb 1:1 0.1 + 0.1 X.04 mancozeb 1:3 0.1 + 0.3 X.04 2,4-D 1:1 0.1 + 0.1 X.04 2,4-D 1:3 0.1 + 0.3 X.04 propiconazole 1:1 0.1 + 0.1 X.04 propiconazole 1:3 0.1 + 0.3 X.04 propiconazole  3:10 0.03 + 0.1  X.04 propiconazole  1:10 0.03 + 0.3  X.04 disodium phosphonate 1:1 0.1 + 0.1 X.04 disodium phosphonate 1:3 0.1 + 0.3 X.04 fenpropimorph 1:1 0.1 + 0.1 X.04 fenpropimorph 1:3 0.1 + 0.3 X.04 fenpropimorph  3:10 0.03 + 0.1  X.04 fenpropimorph  1:10 0.03 + 0.3  X.04 fenpropidin 1:1 0.1 + 0.1 X.04 fenpropidin 1:3 0.1 + 0.3 X.04 fenpropidin  3:10 0.03 + 0.1  X.04 fenpropidin  1:10 0.03 + 0.3  X.04 hexaconazole 1:1 0.1 + 0.1 X.04 hexaconazole 1:3 0.1 + 0.3 X.04 hexaconazole  3:10 0.03 + 0.1  X.04 hexaconazole  1:10 0.03 + 0.3  X.04 paclobutrazol 1:1 0.1 + 0.1 X.04 paclobutrazol 1:3 0.1 + 0.3 X.04 paclobutrazol  1:10 0.03 + 0.3  X.04 trinexapac-ethyl 1:1 0.1 + 0.1 X.04 trinexapac-ethyl 1:3 0.1 + 0.3 X.04 flutriafol 1:1 0.1 + 0.1 X.04 flutriafol 1:3 0.1 + 0.3 X.04 flutriafol  3:10 0.03 + 0.1  X.04 flutriafol  1:10 0.03 + 0.3  X.04 difenoconazole 1:1 0.1 + 0.1 X.04 difenoconazole 1:3 0.1 + 0.3 X.04 difenoconazole  3:10 0.03 + 0.1  X.04 difenoconazole  1:10 0.03 + 0.3  X.04 fludioxonil 1:1 0.1 + 0.1 X.04 fludioxonil 1:3 0.1 + 0.3 X.04 fludioxonil  3:10 0.03 + 0.1  X.04 fludioxonil  1:10 0.03 + 0.3  X.04 cyproconazole 1:1 0.1 + 0.1 X.04 cyproconazole 1:3 0.1 + 0.3 X.04 cyproconazole  3:10 0.03 + 0.1  X.04 cyproconazole  1:10 0.03 + 0.3  X.04 acibenzolar S-methyl 1:1 0.1 + 0.1 X.04 acibenzolar S-methyl 1:3 0.1 + 0.3 X.04 trifloxystrobin 1:1 0.1 + 0.1 X.04 trifloxystrobin 1:3 0.1 + 0.3 X.04 trifloxystrobin  3:10 0.03 + 0.1  X.04 trifloxystrobin  1:10 0.03 + 0.3  X.04 folpet 1:1 0.1 + 0.1 X.04 folpet 1:3 0.1 + 0.3 X.04 folpet  3:10 0.03 + 0.1  X.04 folpet  1:10 0.03 + 0.3  X.04 azoxystrobin 1:1 0.1 + 0.1 X.04 azoxystrobin 1:3 0.1 + 0.3 X.04 azoxystrobin  3:10 0.03 + 0.1  X.04 azoxystrobin  1:10 0.03 + 0.3  X.04 pyraclostrobin 1:1 0.1 + 0.1 X.04 pyraclostrobin 1:3 0.1 + 0.3 X.04 pyraclostrobin  3:10 0.03 + 0.1  X.04 pyraclostrobin  1:10 0.03 + 0.3  X.04 picoxystrobin 1:1 0.1 + 0.1 X.04 picoxystrobin 1:3 0.1 + 0.3 X.04 picoxystrobin  3:10 0.03 + 0.1  X.04 picoxystrobin  1:10 0.03 + 0.3  X.04 sulphur 1:1 0.1 + 0.1 X.04 sulphur 1:3 0.1 + 0.3 X.04 tebuconazole 1:1 0.1 + 0.1 X.04 tebuconazole 1:3 0.1 + 0.3 X.04 tebuconazole  3:10 0.03 + 0.1  X.04 tebuconazole  1:10 0.03 + 0.3  X.04 prothioconazole 1:1 0.1 + 0.1 X.04 prothioconazole 1:3 0.1 + 0.3 X.04 prothioconazole  3:10 0.03 + 0.1  X.04 prothioconazole  1:10 0.03 + 0.3  X.04 fluopyram 1:1 0.1 + 0.1 X.04 fluopyram 1:3 0.1 + 0.3 X.04 fluopyram  1:10 0.03 + 0.3  X.04 copper oxychloride 1:1 0.1 + 0.1 X.04 copper oxychloride 1:3 0.1 + 0.3 X.04 benzovindiflupyr 1:1 0.1 + 0.1 X.04 benzovindiflupyr 1:3 0.1 + 0.3 X.04 benzovindiflupyr  3:10 0.03 + 0.1  X.04 benzovindiflupyr  1:10 0.03 + 0.3  X.04 isopyrazam 1:1 0.1 + 0.1 X.04 isopyrazam 1:3 0.1 + 0.3 X.04 isopyrazam  3:10 0.03 + 0.1  X.04 isopyrazam  1:10 0.03 + 0.3  X.04 pydiflumetofen 1:1 0.1 + 0.1 X.04 pydiflumetofen 1:3 0.1 + 0.3 X.04 pydiflumetofen  3:10 0.03 + 0.1  X.04 pydiflumetofen  1:10 0.03 + 0.3  X.04 fluxapyroxad 1:1 0.1 + 0.1 X.04 fluxapyroxad 1:3 0.1 + 0.3 X.04 fluxapyroxad  3:10 0.03 + 0.1  X.04 fluxapyroxad  1:10 0.03 + 0.3  X.04 quinofumelin 1:1 0.1 + 0.1 X.04 quinofumelin 1:3 0.1 + 0.3 X.04 isoflucypram 1:1 0.1 + 0.1 X.04 isoflucypram 1:3 0.1 + 0.3 X.04 isoflucypram  3:10 0.03 + 0.1  X.04 isoflucypram  1:10 0.03 + 0.3  X.04 mefentrifluconazole 1:1 0.1 + 0.1 X.04 mefentrifluconazole 1:3 0.1 + 0.3 X.04 mefentrifluconazole  3:10 0.03 + 0.1  X.04 mefentrifluconazole  1:10 0.03 + 0.3  X.04 ipflufenoquin 1:1 0.1 + 0.1 X.04 ipflufenoquin 1:3 0.1 + 0.3 X.04 ipflufenoquin  3:10 0.03 + 0.1  X.04 ipflufenoquin  1:10 0.03 + 0.3  X.04 metyltetraprole 1:1 0.1 + 0.1 X.04 metyltetraprole 1:3 0.1 + 0.3 X.04 metyltetraprole  3:10 0.03 + 0.1  X.04 metyltetraprole  1:10 0.03 + 0.3  X.04 aminopyrifen 1:1 0.1 + 0.1 X.04 aminopyrifen 1:3 0.1 + 0.3 X.04 aminopyrifen  3:10 0.03 + 0.1  X.04 aminopyrifen  1:10 0.03 + 0.3  X.04 florylpicoxamid 1:1 0.1 + 0.1 X.04 florylpicoxamid 1:3 0.1 + 0.3 X.04 florylpicoxamid  3:10 0.03 + 0.1  X.04 florylpicoxamid  1:10 0.03 + 0.3  X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1- 1:1 0.1 + 0.1 (1,2,4-triazol-1-yl)propan-2-ol X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1- 1:3 0.1 + 0.3 (1,2,4-triazol-1-yl)propan-2-ol X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-  3:10 0.03 + 0.1  (1,2,4-triazol-1-yl)propan-2-ol X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-  1:10 0.03 + 0.3  (1,2,4-triazol-1-yl)propan-2-ol X.04 fenpicoxamid 1:1 0.1 + 0.1 X.04 fenpicoxamid 1:3 0.1 + 0.3 X.04 fenpicoxamid  3:10 0.03 + 0.1  X.04 fenpicoxamid  1:10 0.03 + 0.3  X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:1 0.1 + 0.1 methoxyimino-N,3-dimethyl-pent-3-enamide X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:3 0.1 + 0.3 methoxyimino-N,3-dimethyl-pent-3-enamide X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  3:10 0.03 + 0.1  methoxyimino-N,3-dimethyl-pent-3-enamide X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  1:10 0.03 + 0.3  methoxyimino-N,3-dimethyl-pent-3-enamide X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:3   0.2 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 5:3  0.1 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 5:6 0.05 + 0.06 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-  5:12 0.025 + 0.06  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-  5:24 0.0125 + 0.06  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 20:3   0.2 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:3   0.1 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:6  0.05 + 0.03 methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- 10:12 0.025 + 0.03  methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino]propanoate X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:100 0.2 + 20  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:200 0.1 + 20  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:400 0.05 + 20.sup.  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:800 0.025 + 20   oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:50 0.2 + 10  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:100 0.1 + 10  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:200 0.05 + 10.sup.  oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-  1:400 0.025 + 10   oxadiazol-3-yl]benzamide X.04 Florylpicoxamid 10:1   0.2 + 0.02 X.04 Florylpicoxamid 5:1  0.1 + 0.02 X.04 Florylpicoxamid 5:2 0.05 + 0.02 X.04 Florylpicoxamid 5:4 0.025 + 0.02  X.04 Florylpicoxamid 5:8 0.0125 + 0.02  X.04 Florylpicoxamid 20:1   0.2 + 0.01 X.04 Florylpicoxamid 10:1   0.1 + 0.01 X.04 Florylpicoxamid 5:1 0.05 + 0.01 X.04 Florylpicoxamid 5:2 0.025 + 0.01  X.04 Florylpicoxamid 5:4 0.0125 + 0.01 

[0250] The following mixture compositions at the reported concentration (in ppm) in tables C3-3 to C3-5 gave the following disease control in this test Septoria glycines (brown spot). Fungicidal activity was evaluated on a 100-0 scale (100=no disease growth; 0=well completely covered by mycelium).

TABLE-US-00023 TABLE C3-3 Conc. COLBY (ppm) Ratio Activity (expected Component A Component B (A:B) A:B (%) activity %) X.02 0.1 70 X.02  0.03 50 chlorothalonil 0.1 0 chlorothalonil 0.3 20 X.02 chlorothalonil 0.1 + 0.1 1:1 90 70 X.02 chlorothalonil 0.1 + 0.3 1:3 100 76 X.02 chlorothalonil 0.03 + 0.3   1:10 100 60 mancozeb 0.1 0 mancozeb 0.3 0 X.02 mancozeb 0.1 + 0.1 1:1 90 70 X.02 mancozeb 0.1 + 0.3 1:3 90 70 fenpropimorph 0.1 50 fenpropimorph 0.3 70 X.02 fenpropimorph 0.1 + 0.1 1:1 100 85 X.02 fenpropimorph 0.1 + 0.3 1:3 100 91 X.02 fenpropimorph 0.03 + 0.1   3:10 100 75 X.02 fenpropimorph 0.03 + 0.3   1:10 100 85 fenpropidin 0.1 0 fenpropidin 0.3 50 X.02 fenpropidin 0.1 + 0.1 1:1 90 70 X.02 fenpropidin 0.1 + 0.3 1:3 100 85 paclobutrazol 0.1 0 paclobutrazol 0.3 50 X.02 paclobutrazol 0.1 + 0.1 1:1 90 70 X.02 paclobutrazol 0.1 + 0.3 1:3 90 85 trinexapac-ethyl 0.3 0 X.02 trinexapac-ethyl 0.1 + 0.3 1:3 90 70 flutriafol 0.1 20 flutriafol 0.3 70 X.02 flutriafol 0.1 + 0.1 1:1 100 76 X.02 flutriafol 0.1 + 0.3 1:3 100 91 X.02 flutriafol 0.03 + 0.1   3:10 70 60 X.02 flutriafol 0.03 + 0.3   1:10 100 85 fludioxonil 0.1 0 fludioxonil 0.3 20 X.02 fludioxonil 0.1 + 0.1 1:1 90 70 X.02 fludioxonil 0.1 + 0.3 1:3 100 76 cyproconazole 0.1 20 X.02 cyproconazole 0.1 + 0.1 1:1 100 76 X.02 cyproconazole 0.03 + 0.1   3:10 70 60 folpet 0.1 0 folpet 0.3 0 X.02 folpet 0.1 + 0.1 1:1 90 70 X.02 folpet 0.1 + 0.3 1:3 100 70 sulphur 0.3 0 X.02 sulphur 0.1 + 0.3 1:3 90 70 tebuconazole 0.1 70 X.02 tebuconazole 0.1 + 0.1 1:1 100 91 X.02 tebuconazole 0.03 + 0.1   3:10 100 85 fluopyram 0.1 0 fluopyram 0.3 50 X.02 fluopyram 0.1 + 0.1 1:1 90 70 X.02 fluopyram 0.1 + 0.3 1:3 100 85 benzovindiflupyr 0.1 70 X.02 benzovindiflupyr 0.1 + 0.1 1:1 100 91 X.02 benzovindiflupyr 0.03 + 0.1   3:10 90 85 isopyrazam 0.1 70 isopyrazam 0.3 70 X.02 isopyrazam 0.1 + 0.1 1:1 100 91 X.02 isopyrazam 0.1 + 0.3 1:3 100 91 X.02 isopyrazam 0.03 + 0.1   3:10 100 85 X.02 isopyrazam 0.03 + 0.3   1:10 100 85 fluxapyroxad 0.1 50 fluxapyroxad 0.3 70 X.02 fluxapyroxad 0.1 + 0.1 1:1 100 85 X.02 fluxapyroxad 0.1 + 0.3 1:3 100 91 X.02 fluxapyroxad 0.03 + 0.1   3:10 90 75 X.02 fluxapyroxad 0.03 + 0.3   1:10 90 85 ipflufenoquin 0.1 0 ipflufenoquin 0.3 20 X.02 ipflufenoquin 0.1 + 0.1 1:1 100 70 X.02 ipflufenoquin 0.1 + 0.3 1:3 100 76 X.02 ipflufenoquin 0.03 + 0.1   3:10 100 50 X.02 ipflufenoquin 0.03 + 0.3   1:10 100 60 fenpicoxamid X.02 fenpicoxamid 0.1 + 0.1 1:1 100 70 X.02 fenpicoxamid 0.03 + 0.1   3:10 90 50

TABLE-US-00024 TABLE C3-4 Conc. COLBY (ppm) Ratio Activity (expected Component A Component B (A:B) A:B (%) activity %) X.04  0.03 70 chlorothalonil 0.3 20 X.04 chlorothalonil 0.03 + 0.3 1:10 100 76 fenpropimorph 0.1 50 fenpropimorph 0.3 70 X.04 fenpropimorph 0.03 + 0.1 3:10 100 85 X.04 fenpropimorph 0.03 + 0.3 1:10 100 91 fenpropidin 0.1 0 fenpropidin 0.3 50 X.04 fenpropidin 0.03 + 0.1 3:10 90 70 X.04 fenpropidin 0.03 + 0.3 1:10 100 85 paclobutrazol 0.3 50 X.04 paclobutrazol 0.03 + 0.3 1:10 90 85 flutriafol 0.1 20 0.3 70 X.04 flutriafol 0.03 + 0.1 3:10 90 76 X.04 flutriafol 0.03 + 0.3 1:10 100 91 fludioxonil 0.1 0 fludioxonil 0.3 20 X.04 fludioxonil 0.03 + 0.1 3:10 90 70 X.04 fludioxonil 0.03 + 0.3 1:10 90 76 cyproconazole 0.1 20 X.04 cyproconazole 0.03 + 0.1 3:10 90 76 folpet 0.1 0 folpet 0.3 0 X.04 folpet 0.03 + 0.1 3:10 90 70 X.04 folpet 0.03 + 0.3 1:10 90 70 tebuconazole 0.1 70 X.04 tebuconazole 0.03 + 0.1 3:10 100 91 fluopyram 0.3 50 X.04 fluopyram 0.03 + 0.3 1:10 90 85 benzovindiflupyr 0.1 70 X.04 benzovindiflupyr 0.03 + 0.1 3:10 100 91 isopyrazam 0.1 70 isopyrazam 0.3 70 X.04 isopyrazam 0.03 + 0.1 3:10 100 91 X.04 isopyrazam 0.03 + 0.3 1:10 100 91 fluxapyroxad 0.1 50 fluxapyroxad 0.3 70 X.04 fluxapyroxad 0.03 + 0.1 3:10 100 85 X.04 fluxapyroxad 0.03 + 0.3 1:10 100 91 ipflufenoquin 0.1 0 ipflufenoquin 0.3 20 X.04 ipflufenoquin 0.03 + 0.1 3:10 100 70 X.04 ipflufenoquin 0.03 + 0.3 1:10 100 76

TABLE-US-00025 TABLE C3-5 Conc. COLBY (ppm) Ratio Activity (expected Component A Component B (A:B) A:B (%) activity %) X.02 0.03125 70 [(1S,2S)-1-methyl-2-(o- 0.06 0 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate [(1S,2S)-1-methyl-2-(o- 0.03 0 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o- 0.03125 + 0.06 50:24 90 70 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o- 0.03125 + 0.03 25:24 90 70 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 0.025 90 X.04 0.0125 50 X.04 0.00625 0 X.04 [(1S,2S)-1-methyl-2-(o-  0.025 + 0.06  5:12 100 90 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-  0.0125 + 0.06  5:24 90 50 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o- 0.00625 + 0.06  5:48 70 0 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o-  0.0125 + 0.03 10:24 70 50 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o- 0.00625 + 0.03 10:48 50 0 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate Florylpicoxamid 0.02 0 Florylpicoxamid 0.01 0 X.04 Florylpicoxamid  0.025 + 0.02 5:4 100 90 X.04 Florylpicoxamid  0.0125 + 0.02 5:8 90 50 X.04 Florylpicoxamid 0.006125 + 0.02   5:16 70 0 X.04 Florylpicoxamid  0.025 + 0.01 5:2 100 90 X.04 Florylpicoxamid  0.0125 + 0.01 5:4 90 50

Example C4—Fungicidal Activity Against Glomerella lagenarium syn. Colletotrichum lagenarium (Anthracnose)

[0251] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically after 72 hrs at 620 nm.

[0252] The following compound mixtures gave at least 80% control Glomerella lagenarium at rates cited in the table when compared to untreated control under the same conditions, which showed extensive disease development:

TABLE-US-00026 TABLE C4-1 Fungicidal activity >80% (% of untreated) against Glomerella lagenarium Conc. Ratio (ppm) Component A Component B A:B (A:B) X.02 chlorothalonil 1:1 0.1 + 0.1 X.02 chlorothalonil 1:3 0.1 + 0.3 X.02 chlorothalonil  1:10 0.03 + 0.3  X.02 trifloxystrobin 1:1 0.1 + 0.1 X.02 trifloxystrobin 1:3 0.1 + 0.3 X.02 trifloxystrobin  3:10 0.03 + 0.1  X.02 trifloxystrobin  1:10 0.03 + 0.3  X.02 folpet 1:3 0.1 + 0.3 X.02 folpet  1:10 0.03 + 0.3  X.02 azoxystrobin 1:1 0.1 + 0.1 X.02 azoxystrobin 1:3 0.1 + 0.3 X.02 azoxystrobin  3:10 0.03 + 0.1  X.02 azoxystrobin  1:10 0.03 + 0.3  X.02 pyraclostrobin 1:1 0.1 + 0.1 X.02 pyraclostrobin 1:3 0.1 + 0.3 X.02 pyraclostrobin  3:10 0.03 + 0.1  X.02 pyraclostrobin  1:10 0.03 + 0.3  X.02 picoxystrobin 1:1 0.1 + 0.1 X.02 picoxystrobin 1:3 0.1 + 0.3 X.02 picoxystrobin  3:10 0.03 + 0.1  X.02 picoxystrobin  1:10 0.03 + 0.3  X.02 prothioconazole 1:3 0.1 + 0.3 X.02 prothioconazole  1:10 0.03 + 0.3  X.02 benzovindiflupyr 1:1 0.1 + 0.1 X.02 benzovindiflupyr 1:3 0.1 + 0.3 X.02 benzovindiflupyr  1:10 0.03 + 0.3  X.02 quinofumelin 1:1 0.1 + 0.1 X.02 quinofumelin 1:3 0.1 + 0.3 X.02 quinofumelin  3:10 0.03 + 0.1  X.02 quinofumelin  1:10 0.03 + 0.3  X.02 ipflufenoquin 1:1 0.1 + 0.1 X.02 ipflufenoquin 1:3 0.1 + 0.3 X.02 ipflufenoquin  1:10 0.03 + 0.3  X.02 metyltetraprole 1:1 0.1 + 0.1 X.02 metyltetraprole 1:3 0.1 + 0.3 X.02 metyltetraprole  3:10 0.03 + 0.1  X.02 metyltetraprole  1:10 0.03 + 0.3  X.02 aminopyrifen 1:3 0.1 + 0.3 X.02 florylpicoxamid 1:1 0.1 + 0.1 X.02 florylpicoxamid 1:3 0.1 + 0.3 X.02 florylpicoxamid  3:10 0.03 + 0.1  X.02 florylpicoxamid  1:10 0.03 + 0.3  X.02 fenpicoxamid 1:1 0.1 + 0.1 X.02 fenpicoxamid 1:3 0.1 + 0.3 X.02 fenpicoxamid  3:10 0.03 + 0.1  X.02 fenpicoxamid  1:10 0.03 + 0.3  X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:1 0.1 + 0.1 methoxyimino-N,3-dimethyl-pent-3-enamide X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:3 0.1 + 0.3 methoxyimino-N,3-dimethyl-pent-3-enamide X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  3:10 0.03 + 0.1  methoxyimino-N,3-dimethyl-pent-3-enamide X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  1:10 0.03 + 0.3  methoxyimino-N,3-dimethyl-pent-3-enamide

TABLE-US-00027 TABLE C4-2 Fungicidal activity >80% (% of untreated) against Glomerella lagenarium Conc. Ratio (ppm) Component A Component B A:B (A:B) X.04 glyphosate 1:1 0.1 + 0.1 X.04 glyphosate 1:3 0.1 + 0.3 X.04 chlorothalonil 1:1 0.1 + 0.1 X.04 chlorothalonil 1:3 0.1 + 0.3 X.04 chlorothalonil  3:10 0.03 + 0.1  X.04 chlorothalonil  1:10 0.03 + 0.3  X.04 mancozeb 1:1 0.1 + 0.1 X.04 mancozeb 1:3 0.1 + 0.3 X.04 2,4-D 1:1 0.1 + 0.1 X.04 2,4-D 1:3 0.1 + 0.3 X.04 propiconazole 1:1 0.1 + 0.1 X.04 propiconazole 1:3 0.1 + 0.3 X.04 disodium phosphonate 1:1 0.1 + 0.1 X.04 disodium phosphonate 1:3 0.1 + 0.3 X.04 fenpropimorph 1:1 0.1 + 0.1 X.04 fenpropimorph 1:3 0.1 + 0.3 X.04 fenpropidin 1:1 0.1 + 0.1 X.04 fenpropidin 1:3 0.1 + 0.3 X.04 hexaconazole 1:1 0.1 + 0.1 X.04 hexaconazole 1:3 0.1 + 0.3 X.04 paclobutrazol 1:1 0.1 + 0.1 X.04 paclobutrazol 1:3 0.1 + 0.3 X.04 trinexapac-ethyl 1:1 0.1 + 0.1 X.04 trinexapac-ethyl 1:3 0.1 + 0.3 X.04 flutriafol 1:1 0.1 + 0.1 X.04 flutriafol 1:3 0.1 + 0.3 X.04 difenoconazole 1:1 0.1 + 0.1 X.04 difenoconazole 1:3 0.1 + 0.3 X.04 fludioxonil 1:1 0.1 + 0.1 X.04 fludioxonil 1:3 0.1 + 0.3 X.04 cyproconazole 1:1 0.1 + 0.1 X.04 cyproconazole 1:3 0.1 + 0.3 X.04 acibenzolar S-methyl 1:1 0.1 + 0.1 X.04 acibenzolar S-methyl 1:3 0.1 + 0.3 X.04 trifloxystrobin 1:1 0.1 + 0.1 X.04 trifloxystrobin 1:3 0.1 + 0.3 X.04 trifloxystrobin  3:10 0.03 + 0.1  X.04 trifloxystrobin  1:10 0.03 + 0.3  X.04 folpet 1:1 0.1 + 0.1 X.04 folpet 1:3 0.1 + 0.3 X.04 folpet  1:10 0.03 + 0.3  X.04 azoxystrobin 1:1 0.1 + 0.1 X.04 azoxystrobin 1:3 0.1 + 0.3 X.04 azoxystrobin  3:10 0.03 + 0.1  X.04 azoxystrobin  1:10 0.03 + 0.3  X.04 pyraclostrobin 1:1 0.1 + 0.1 X.04 pyraclostrobin 1:3 0.1 + 0.3 X.04 pyraclostrobin  3:10 0.03 + 0.1  X.04 pyraclostrobin  1:10 0.03 + 0.3  X.04 picoxystrobin 1:1 0.1 + 0.1 X.04 picoxystrobin 1:3 0.1 + 0.3 X.04 picoxystrobin  3:10 0.03 + 0.1  X.04 picoxystrobin  1:10 0.03 + 0.3  X.04 sulphur 1:1 0.1 + 0.1 X.04 sulphur 1:3 0.1 + 0.3 X.04 tebuconazole 1:1 0.1 + 0.1 X.04 tebuconazole 1:3 0.1 + 0.3 X.04 prothioconazole 1:1 0.1 + 0.1 X.04 prothioconazole 1:3 0.1 + 0.3 X.04 prothioconazole  1:10 0.03 + 0.3  X.04 fluopyram 1:1 0.1 + 0.1 X.04 fluopyram 1:3 0.1 + 0.3 X.04 copper oxychloride 1:1 0.1 + 0.1 X.04 copper oxychloride 1:3 0.1 + 0.3 X.04 benzovindiflupyr 1:1 0.1 + 0.1 X.04 benzovindiflupyr 1:3 0.1 + 0.3 X.04 benzovindiflupyr  3:10 0.03 + 0.1  X.04 benzovindiflupyr  1:10 0.03 + 0.3  X.04 isopyrazam 1:1 0.1 + 0.1 X.04 isopyrazam 1:3 0.1 + 0.3 X.04 pydiflumetofen 1:1 0.1 + 0.1 X.04 pydiflumetofen 1:3 0.1 + 0.3 X.04 fluxapyroxad 1:1 0.1 + 0.1 X.04 fluxapyroxad 1:3 0.1 + 0.3 X.04 quinofumelin 1:1 0.1 + 0.1 X.04 quinofumelin 1:3 0.1 + 0.3 X.04 quinofumelin  3:10 0.03 + 0.1  X.04 quinofumelin  1:10 0.03 + 0.3  X.04 isoflucypram 1:1 0.1 + 0.1 X.04 isoflucypram 1:3 0.1 + 0.3 X.04 mefentrifluconazole 1:1 0.1 + 0.1 X.04 mefentrifluconazole 1:3 0.1 + 0.3 X.04 ipflufenoquin 1:1 0.1 + 0.1 X.04 ipflufenoquin 1:3 0.1 + 0.3 X.04 ipflufenoquin  3:10 0.03 + 0.1  X.04 ipflufenoquin  1:10 0.03 + 0.3  X.04 metyltetraprole 1:1 0.1 + 0.1 X.04 metyltetraprole 1:3 0.1 + 0.3 X.04 metyltetraprole  3:10 0.03 + 0.1  X.04 metyltetraprole  1:10 0.03 + 0.3  X.04 aminopyrifen 1:1 0.1 + 0.1 X.04 aminopyrifen 1:3 0.1 + 0.3 X.04 florylpicoxamid 1:1 0.1 + 0.1 X.04 florylpicoxamid 1:3 0.1 + 0.3 X.04 florylpicoxamid  3:10 0.03 + 0.1  X.04 florylpicoxamid  1:10 0.03 + 0.3  X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1- 1:1 0.1 + 0.1 (1,2,4-triazol-1-yl)propan-2-ol X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1- 1:3 0.1 + 0.3 (1,2,4-triazol-1-yl)propan-2-ol X.04 fenpicoxamid 1:1 0.1 + 0.1 X.04 fenpicoxamid 1:3 0.1 + 0.3 X.04 fenpicoxamid  3:10 0.03 + 0.1  X.04 fenpicoxamid  1:10 0.03 + 0.3  X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:1 0.1 + 0.1 methoxyimino-N,3-dimethyl-pent-3-enamide X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2- 1:3 0.1 + 0.3 methoxyimino-N,3-dimethyl-pent-3-enamide X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  3:10 0.03 + 0.1  methoxyimino-N,3-dimethyl-pent-3-enamide X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-  1:10 0.03 + 0.3  methoxyimino-N,3-dimethyl-pent-3-enamide

[0253] The following mixture compositions at the reported concentration (in ppm) in tables C.sub.4-3 and C.sub.4-4 gave the following disease control in this test (Glomerella lagenarium syn. Colletotrichum lagenarium). Fungicidal activity was evaluated on a 100-0 scale (100=no disease growth; 0=well completely covered by mycelium).

TABLE-US-00028 TABLE C4-3 Conc. COLBY (ppm) Ratio Activity (expected Component A Component B (A:B) A:B (%) activity %) X.02 0.1 20 X.02  0.03 0 chlorothalonil 0.1 50 X.02 chlorothalonil 0.1 + 0.1 1:1 90 60 mancozeb 0.1 0 mancozeb 0.3 20 X.02 mancozeb 0.1 + 0.1 1:1 50 20 X.02 mancozeb 0.1 + 0.3 1:3 70 36 folpet 0.1 20 folpet 0.3 70 X.02 folpet 0.1 + 0.1 1:1 50 36 X.02 folpet 0.1 + 0.3 1:3 100 76 X.02 folpet 0.03 + 0.1   3:10 50 20 X.02 folpet 0.03 + 0.3   1:10 90 70 prothioconazole 0.1 20 prothioconazole 0.3 70 X.02 prothioconazole 0.1 + 0.1 1:1 50 36 X.02 prothioconazole 0.1 + 0.3 1:3 90 76 X.02 prothioconazole 0.03 + 0.3   1:10 90 70 benzovindiflupyr 0.1 50 X.02 benzovindiflupyr 0.1 + 0.1 1:1 90 60 X.02 benzovindiflupyr 0.03 + 0.3   1:10 70 50 mefentrifluconazole 0.3 0 X.02 mefentrifluconazole 0.03 + 0.3   1:10 20 0 ipflufenoquin 0.1 50 X.02 ipflufenoquin 0.1 + 0.1 1:1 90 60 X.02 ipflufenoquin 0.03 + 0.1   3:10 70 50 aminopyrifen 0.1 20 aminopyrifen 0.3 50 X.02 aminopyrifen 0.1 + 0.1 1:1 70 36 X.02 aminopyrifen 0.1 + 0.3 1:3 90 60 X.02 aminopyrifen 0.03 + 0.1   3:10 50 20 X.02 aminopyrifen 0.03 + 0.3   1:10 70 50 florylpicoxamid 0.1 20 X.02 florylpicoxamid 0.1 + 0.1 1:1 100 36 X.02 florylpicoxamid 0.03 + 0.1   3:10 90 20 2-[6-(4- 0.3 0 bromophenoxy)-2- (trifluoromethyl)-3- pyridyl]-1-(1,2,4-triazol- 1-yl)propan-2-ol X.02 2-[6-(4- 0.03 + 0.3   1:10 20 0 bromophenoxy)-2- (trifluoromethyl)-3- pyridyl]-1-(1,2,4-triazol- 1-yl)propan-2-ol fenpicoxamid 0.1 20 fenpicoxamid 0.3 70 X.02 fenpicoxamid 0.1 + 0.1 1:1 100 36 X.02 fenpicoxamid 0.1 + 0.3 1:3 100 76 X.02 fenpicoxamid 0.03 + 0.1   3:10 90 20 X.02 fenpicoxamid 0.03 + 0.3   1:10 100 70

TABLE-US-00029 TABLE C4-4 Conc. COLBY (ppm) Ratio Activity (expected Component A Component B (A:B) A:B (%) activity %) X.04  0.03 0 chlorothalonil 0.1 0 X.04 chlorothalonil 0.03 + 0.1 3:10 90 0 mancozeb 0.1 0 X.04 mancozeb 0.03 + 0.1 3:10 20 0 folpet 0.1 20 folpet 0.3 70 X.04 folpet 0.03 + 0.1 3:10 50 20 X.04 folpet 0.03 + 0.3 1:10 100 70 prothioconazole 0.1 20 prothioconazole 0.3 70 X.04 prothioconazole 0.03 + 0.1 3:10 70 20 X.04 prothioconazole 0.03 + 0.3 1:10 100 70 benzovindiflupyr 0.1 50 X.04 benzovindiflupyr 0.03 + 0.1 3:10 90 50 mefentrifluconazole 0.3 0 X.04 mefentrifluconazole 0.03 + 0.3 1:10 20 0 ipflufenoquin 0.1 50 X.04 ipflufenoquin 0.03 + 0.1 3:10 90 50 aminopyrifen 0.1 20 aminopyrifen 0.3 50 X.04 aminopyrifen 0.03 + 0.1 3:10 50 20 X.04 aminopyrifen 0.03 + 0.3 1:10 70 50 florylpicoxamid 0.1 20 X.04 florylpicoxamid 0.03 + 0.1 3:10 100 20 2-[6-(4- 0.3 0 bromophenoxy)-2- (trifluoromethyl)-3- pyridyl]-1-(1,2,4-triazol- 1-yl)propan-2-ol X.04 2-[6-(4- 0.03 + 0.3 1:10 20 0 bromophenoxy)-2- (trifluoromethyl)-3- pyridyl]-1-(1,2,4-triazol- 1-yl)propan-2-ol fenpicoxamid 0.1 20 fenpicoxamid 0.3 70 X.04 fenpicoxamid 0.03 + 0.1 3:10 100 20 X.04 fenpicoxamid 0.03 + 0.3 1:10 100 70

Example C5—Fungicidal Activity Against Corynespora cassiicola (Target Leaf Spot)

[0254] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24 C and the inhibition of growth was determined photometrically after 3-4 days at 620 nm.

[0255] The following mixture compositions at the reported concentration (in ppm) in tables C4-3 and C4-4 gave the following disease control in this test (Corynespora cassiicola). Fungicidal activity was evaluated on a 100-0 scale (100=no disease growth; 0=well completely covered by mycelium).

TABLE-US-00030 TABLE C5-1 Conc. COLBY (ppm) Ratio Activity (expected Component A Component B (A:B) A:B (%) activity %) X.02 1 20 X.02 [(1S,2S)-1-methyl-2-(o-   1 + 0.06 50:3 50 20 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.02 [(1S,2S)-1-methyl-2-(o-   1 + 0.03 100:3  50 20 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate N-(2-fluorophenyl)-4-[5- 20 0 (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide N-(2-fluorophenyl)-4-[5- 10 0 (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5- 1 + 20  1:20 50 20 (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide X.02 N-(2-fluorophenyl)-4-[5- 1 + 10  1:10 50 20 (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide X.04 0.2 20 [(1S,2S)-1-methyl-2-(o- 0.06 0 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate [(1S,2S)-1-methyl-2-(o- 0.03 0 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o- 0.2 + 0.06 10:3 50 20 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate X.04 [(1S,2S)-1-methyl-2-(o- 0.2 + 0.03 20:3 20 20 tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- pyridine-2- carbonyl)amino]propanoate N-(2-fluorophenyl)-4-[5- 20 0 (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide N-(2-fluorophenyl)-4-[5- 10 0 (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5- 0.2 + 20     1:100 50 20 (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide X.04 N-(2-fluorophenyl)-4-[5- 0.2 + 10    1:50 50 20 (trifluoromethyl)-1,2,4- oxadiazol-3-yl]benzamide Florylpicoxamid 0.02 0 X.02 Florylpicoxamid   1 + 0.02 50:1 50 20 X.02 Florylpicoxamid   1 + 0.01 100:1  50 20

Example D: Preventative Activity Against Phakopsora pachyrhizi on Soybean

[0256] Whole soybean plants are treated with the recited active ingredients 4 weeks after planting. 1 day after spraying leaf disks are cut from the first trifoliate leaf. Five repetitions at each rate are conducted. The leaf disks are inoculated with Phakopsora pachyrhizi (Asian soybean rust) one day after treatment. Evaluation of the leaf disks is conducted 11 to 14 days after inoculation and the activity is derived from the relation of the treated vs untreated, infested check. (100=no disease, no damage to the leaf, 0=high infestation, leaf damaged heavily). The rates of the active ingredients used are given in the tables as g active ingredient (a.i.)/ha.

[0257] The results are shown in the tables below:

TABLE-US-00031 TABLE D1 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.02 Fenpropimorph pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.5 0 33 2.25 0 23 1.13 0 1 0 900 76 0 450 43 0 225 8 4.5 900 1:200 94 84 2.25 450 1:200 94 56 1.13 225 1:200 78 9 1.13 450 1:400 83 44

TABLE-US-00032 TABLE D2 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.02 Fenpropidin pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.5 0 33 2.25 0 23 1.13 0 1 0 900 82 0 450 61 0 225 64 4.5 900 1:200 96 88 2.25 450 1:200 93 70 1.13 225 1:200 89 64 1.13 450 1:400 88 61

TABLE-US-00033 TABLE D3 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.02 Trifloxystrobin pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 9.0 0 38 4.50 0 22 2.25 0 14 0 18 33 0 9 1 0 4.5 0 9.0 18 1:2 92 59 4.50 9 1:2 88 23 2.25 4.5 1:2 62 14 2.25 9 1:4 74 15

TABLE-US-00034 TABLE D4 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.02 Azoxystrobin pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 9.0 0 38 4.50 0 22 2.25 0 14 0 18 26 0 9 2 0 4.5 0 9.0 18 1:2 96 54 4.50 9 1:2 89 24 2.25 4.5 1:2 57 14 2.25 9 1:4 85 16

TABLE-US-00035 TABLE D5 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.02 Metyltetraprole pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 9.0 0 38 4.50 0 22 2.25 0 14 0 18 2 0 9 2 9.0 18 1:2 78 39 4.50 9 1:2 31 24 2.25 9 1:4 21 16

TABLE-US-00036 TABLE D6 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.02 Pyraclostrobin pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 9.0 0 38 4.50 0 22 2.25 0 14 0 18 0 0 9 1 0 4.5 1 9.0 18 1:2 92 38 4.50 9 1:2 75 23 2.25 4.5 1:2 40 15 2.25 9 1:4 34 15

TABLE-US-00037 TABLE D7 Activity (% of untreated) against Phakopsora pachyrhizi (Z,2E)-5-[1-(2,4- dichlorophenyl)pyrazol-3- COLBY Compound yl]oxy-2-methoxyimino-N,3- Com- Observed Expected X.02 dimethyl-pent-3-enamide pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 9.0 0 38 4.50 0 22 0 18 3 0 9 2 9.0 18 1:2 92 40 4.50 9 1:2 68 24

TABLE-US-00038 TABLE D8 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.02 Benzovindiflupyr pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.50 0 20 2.25 0 13 0 4.50 94 0 2.25 92 4.50 4.50 1:1 99 95 2.25 2.25 1:1 93 93 2.25 4.50 1:2 99 95

TABLE-US-00039 TABLE D9 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.02 Pydiflumetofen pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.50 0 20 2.25 0 13 0 45 4 0 22.5 0 4.50 45 1:10 70 24 2.25 22.5 1:10 40 13 2.25 45 1:20 63 17

TABLE-US-00040 TABLE D10 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.02 Prothioconazole pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.50 0 20 2.25 0 13 0 45 76 0 22.5 74 4.50 45 1:10 97 81 2.25 22.5 1:10 98 77 2.25 45 1:20 96 79

TABLE-US-00041 TABLE D11 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.02 Difenoconazole pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.50 0 20 2.25 0 13 0 45 0 0 22.5 0 4.50 45 1:10 68 20 2.25 22.5 1:10 52 13 2.25 45 1:20 23 13

TABLE-US-00042 TABLE D12 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.02 Cyproconazole pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.50 0 20 2.25 0 13 0 45 52 0 22.5 51 4.50 45 1:10 97 62 2.25 22.5 1:10 88 57 2.25 45 1:20 95 59

TABLE-US-00043 TABLE D13 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Fenpropimorph pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.5 0 67 2.25 0 22 1.13 0 20 0 900 76 0 450 43 0 225 8 4.5 900 1:200 95 92 2.25 450 1:200 95 56 1.13 225 1:200 83 26 1.13 450 1:400 93 55

TABLE-US-00044 TABLE D14 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Fenpropidin pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.5 0 67 2.25 0 22 1.13 0 20 0 900 82 0 450 61 0 225 64 4.5 900 1:200 93 94 2.25 450 1:200 91 69 1.13 225 1:200 89 71 1.13 450 1:400 90 68

TABLE-US-00045 TABLE D15 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Mancozeb pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 2.25 0 22 1.13 0 20 0 450 39 0 225 27 2.25 450 1:200 65 53 1.13 225 1:200 50 41 1.13 450 1:400 53 51

TABLE-US-00046 TABLE D16 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Chlorothalonil pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 2.25 0 22 1.13 0 20 0 900 7 0 450 8 2.25 900 1:400 52 28 1.13 450 1:400 37 26 1.13 900 1:800 52 25

TABLE-US-00047 TABLE D17 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Folpet pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 2.25 0 22 1.13 0 20 0 900 13 0 450 4 2.25 900 1:400 52 32 1.13 450 1:400 35 23 1.13 900 1:800 33 30

TABLE-US-00048 TABLE D18 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Trifloxystrobin pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 18 0 74 9 0 81 4.5 0 34 2.25 0 35 0 18 19 0 9 0 0 4.5 3 0 2.25 0 9 9 1:1 92 81 4.5 4.5 1:1 83 35 2.25 2.25 1:1 42 35

TABLE-US-00049 TABLE D19 Activity (% of untreated) against Phakopsora pachyrhizi Compound Com- Observed Expected X.04 Azoxystrobin pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 18 0 74 9 0 81 4.5 0 34 2.25 0 35 0 18 9 0 9 23 0 4.5 15 0 2.25 0 9 9 1:1 98 85 4.5 4.5 1:1 92 43 2.25 2.25 1:1 86 35

TABLE-US-00050 TABLE D20 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Metyltetraprole pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 9.0 0 59 4.50 0 49 2.25 0 17 0 18 2 0 9 2 9.0 18 1:2 78 60 4.50 9 1:2 51 50 2.25 9 1:4 56 18

TABLE-US-00051 TABLE D21 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Pyraclostrobin pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 9.0 0 59 4.50 0 49 2.25 0 17 0 18 0 0 9 1 0 4.5 1 9.0 18 1:2 92 59 4.50 9 1:2 86 49 2.25 4.5 1:2 82 18 2.25 9 1:4 88 18

TABLE-US-00052 TABLE D22 Activity (% of untreated) against Phakopsora pachyrhizi (Z,2E)-5-[1-(2,4- dichlorophenyl)pyrazol- 3-yl]oxy-2- methoxyimino-N,3- COLBY Compound dimethyl-pent-3- Com- Observed Expected X.04 enamide pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 9.0 0 59 4.50 0 49 2.25 0 17 0 18 3 0 9 2 9.0 18 1:2 90 61 4.50 9 1:2 89 50 2.25 9 1:4 83 19

TABLE-US-00053 TABLE D23 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Benzovindiflupyr pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.50 0 53 2.25 0 22 0 4.50 94 0 2.25 92 4.50 4.50 1:1 100 97 2.25 2.25 1:1 98 94 2.25 4.50 1:2 99 95

TABLE-US-00054 TABLE D24 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Pydiflumetofen pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.50 0 53 2.25 0 22 0 45 4 0 22.5 0 4.50 45 1:10 81 55 2.25 22.5 1:10 70 22 2.25 45 1:20 66 25

TABLE-US-00055 TABLE D25 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Prothioconazole pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.50 0 53 2.25 0 22 0 45 76 0 22.5 74 4.50 45 1:10 92 89 2.25 22.5 1:10 96 80 2.25 45 1:20 94 81

TABLE-US-00056 TABLE D26 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Difenoconazole pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 4.50 0 53 2.25 0 22 0 45 0 0 22.5 0 4.50 45 1:10 75 53 2.25 22.5 1:10 65 22 2.25 45 1:20 71 22

TABLE-US-00057 TABLE D27 Activity (% of untreated) against Phakopsora pachyrhizi COLBY Compound Com- Observed Expected X.04 Cyproconazole pound:Mixing Activity Activity (g/ha) (g/ha) partner (%) (%) 2.25 0 22 0 45 52 0 22.5 51 2.25 22.5 1:10 89 62 2.25 45 1:20 96 63