OA20876A - Fungicidal compositions - Google Patents

Fungicidal compositions Download PDF

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Publication number
OA20876A
OA20876A OA1202200355 OA20876A OA 20876 A OA20876 A OA 20876A OA 1202200355 OA1202200355 OA 1202200355 OA 20876 A OA20876 A OA 20876A
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OAPI
Prior art keywords
methyl
phenyl
methoxy
component
trifluoromethyl
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OA1202200355
Inventor
Stefano RENDINE
Farhan BOU HAMDAN
Laura Quaranta
Simon Williams
Matthias Weiss
Thomas James HOFFMAN
Ulrich Johannes Haas
David Beattie
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Syngenta Crop Protection Ag
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Publication of OA20876A publication Critical patent/OA20876A/en

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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.

Description

Fungicidal Compositions
The présent invention relates to novel fungicidal compositions, to their use in agriculture or horticulture for controlling diseases caused by phytopathogens, especiaily phytopathogenic fungi, and to methods 5 of controlling diseases on useful plants.
Whilst many fungicidal compounds and compositions, belonging to various different chemioal classes, hâve been/are being developed for use as fungicides in crops of useful plants, crop tolérance and activity against particular phytopathogenic fungi do not always satisfy the needs of agricultural practice in many 10 respects. Therefore, there is a continuing need to find new compounds and compositions having superior biological properties for use in controlling or preventing infestation of plants by phytopathogenic fungi. For example, compounds possessing a greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, increased biodegradabîlity. Or else, compositions possessing a broader spectrum of activity, improved crop tolérance, synergistic 15 interactions or potentiating properties, or compositions which display a more rapid onset of action or which hâve longer fasting residual activity or which enable a réduction in the number of applications and/or a réduction in the application rate of the compounds and compositions required for effective control of a phytopathogen, thereby enabling bénéficiai resistance-management practices, reduced environmental impact and reduced operator exposure.
The use of compositions comprising mixtures of different fungicidal compounds possessing different modes of action can address some of these needs (eg, by combining fungicides with differing spectrums of activity).
According to the présent invention, there is provided a fungicidal composition comprising a mixture of components (A) and (B) as active ingrédients, wherein component (A) is a compound of formula (I)
wherein
R1 is methyl;
R2 is hydrogen;
R3 is hydrogen;
R4 is Ca-CTcycloalkyl;
or an agrono mica lly acceptable sait thereof;
and component (B) is a compound selected from the group consisting of:
bixafen, sulfur, copper hydroxide, triclopyricarb, acibenzolar-S-methyl, copper oxychioride, cyproconazoie, difenoconazole, epoxicon-azole, flutriafol, hexaconazole, rpconazole, metconazole, paclobutrazole, prothioconazole, prochloraz, propiconazole, pyrisoxazole, tebucon-azole, fenpropidin, fenpropimorph, spiroxamine, cyprodinil, fludioxonil, metalaxyl, metalaxyl-M (mefenoxam), carbendazîm, penthiopyrad, azoxystrobin, dimoxystrobin, fenaminstrobin, flufenoxystrobin, fluoxastrobin, metomi-nostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraciostrobin, pyrametostrobin, pyraoxystrobin, mancozeb, folpet, chlorothalonil, fluazinam, fluxapyroxad, fenhexamid, fos-etylaluminium, pyribencart», tricyclazole, mandipropamid, flubeneteram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, isotianil, dipymetîtrone, fluindapyr, coumethoxystrobin (jiaxiangjunzhi), Ivbenmixianan, mandestrobin. oxathiapiprolin, pyraziflumjd, inpyrÎluxam, mefentrifluconazole, ipfentrifluconazole, aminopyrifen, (Z,2E)-5-[1-(4-ch1orophenyl)pyrazoi-3-yi]oxy-2methoxyimino-N,3-dîmethyl-pent-3-enamide, florylpicoxamid, fenpicoxamid, ipflufenoquîn, quinofumelin, benzothiostrobin, fluopyram, pyrapropoyne, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylindan-4-y!)pyridine-3-carboxaiïiîde1 4-[[6-[2-(2,4-difluorophenyi)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol1-yl)propyl]-3-pyridyl]oxy]benzonitrile, metyltetra proie, fluoxapiprolin, enoxastrobin, 4-((6-(2-(2,4difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3pyridyl]oxy]benzonitrîle, trinexapac, trinexapac-ethyl, coumoxystrobin, N'-[5-bromo-2-methyl-6-[(1S)-1methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyî-N-methyl-formamidfne, N'-[5-bromo-2-methy 1-6-((1 R)-1methyl-Z-propoxy-ethoxyl-S-pyridyiFN-ethyl-N-methyl-formamidîne, N’-[5-bromo-2-methyl-6-(1-methyl2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyf-fomnamidine, N’-[5-bromo-2-methyl-6-(1-methyl-2propoxy-ethoxyJ-S-pyridyn-N-isopropyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6~(2propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N-isopiOpyl-N'-fS-methoxy^-methyM(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)pheny[]-N-methyl-formamidfne, N’-[4-(1-cyclopropyl-2,2,2trifluOΓO-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-yf]phenyl]-N-methyl-fonnamidine, N-ethyl-N’-[5methoxy-2-methyl-4-[2-trifuoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine1 N-(2fluorophenyl)-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)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5 (tnfIuoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (28)-2-((4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)a min o(propanoa te, 1-methoxy-3-methyl-1-[[4[5-(tnf1uoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)1,2,4-oxadiazoi-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-((4-[5-(trifluoromethy 1)-1,2,4-oxadiazoi-3yi]phenyl]methyl]urea, N-[[4-[5-(trifIuoromethyl)-1,2,4-oxadiazo!-3-yl]phenyl]methyl]propanamide, 4,4dimethyl-2-[[4-[5-(trifluoromethyi)-1,2,4-oxadiazol-3-yl]phenyl)methyl]isoxazolidin-3-one, 5,5-dimethyl2-((4-(5-(trifluoromethyt)-l,2,4-oxadiazol-3-yl]phenyi]methyl]isoxazolidin-3-one, ethyl 1 -[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methy1]pyrazole-4-carboxylate, N, N-di methyl-1-((4-(5(trifluoromethyl)-1,2,4-oxadiazol-3-yllphenyl]methyl]-1,2,4-triazol-3-amine, 2-[6-(4-chlorophenoxy)-2(trifluoromethyl)-3-pyridy[]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)3-pyrîdyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-(2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, 3-(2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxypropyl]imidazole-4-carbonftnle, (4-phenoxyphenyi)methyl 2-amino-6-methyt-pyridine-3-carboxyiate, Nmethyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; N-methyf-4-[5(trifïuoromethyf)-1,2,4-oxadiazol-3-yl]benzamîde; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide, (5-methyl-2-pyridyi)-[4-[5-(trifluoromethyl)-1,2,4oxadiazoi-3-yl]phenyl]methanone, (3-methyiisoxazol-5-yi)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3yljphenyl]methanone, ethyl 1-n5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4carboxylate, 212-difluoro-N-methy)-2-[4-[5-(trifîuoromethyl)-1,2,4-oxadiazol-3-yl]phenylIacetamide, N[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-Cmethyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[3-(4-chlorophenyî)-4,5dihydroisoxazol-5-yl]-5-methyl-1,2,4-oxadiazole-3-carboxamide, 2-(difluoromethyl)-N-(1,1-dimethyl-3propyl-indan-4-yl)pyridine-3-carboxamide, E(1S,2S)-2-(4-fluoro-2-methyi-phenyl)-1,3-dimethyl-butyl] (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethyl-butyl] (2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2carbonyi]amino]propanoate, cis-jasmone, potassium phosphonate, calcium phosphonate, glyphosate (including the diammonium, isopropyiammonium and potassium salts thereof), 2,4-D (including the choline sait and 2-ethyihexyl ester thereof), dicamba (including the aluminium, aminopropyl, bisaminopropylmethyl, choline, dichloroprop, diglycoiamine, dimethylamine, dîmethylammonium, potassium and sodium salts thereof), glufosinate (including the ammonium sait thereof), thramethoxam, oyclobutrifluram, isocycloseram, spiropidion, abamectin, emamectin, cyantraniliproie, chlorantraniliprole, diafenthluron, brofianilide, 2-chloro-N-cyclopropyl-5-(1-{2,6-dichloro-4-[1,2,2,2tetrafluoro-1 -(trifiuoromethy!)ethyl]phenyl}-1 H-pyrazol-4-yl)-N-methylnicotinamide and fluxametamide.
In general, the weight ratio of component (A) to component (B) may preferably be from 100:1 to 1:100, from 50:1 to 1:50, from 20:1 to 1:50, from 15:1 to 1:50 from 15:1 to 1 ;30, from 12:1 to 1:25, from 10:1 to 1:20, from 5:1 and 1:15, from 3:1 to 1:10 or from 2:1 to 1:5.
Further according to the invention, there is provided a method of controtling or preventing phytopathogenic diseases, especiaily phytopathogenicfungi, on useful piants or on propagation material thereof, which comprises applying to the useful plants, the locus thereof or propagation material thereof a fungrcidal composition according to the invention.
The benefits provided by certain fungicidai mixture compositions according to the invention may also include, inter a!ia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingrédients (for example, greater biotogical activity, an advantageous spectrum of activity, an increased safety profile, improved 10 physico-chemical properties, or increased biodegradability).
Preferred groups and values for the substituents R1, R2, R3 and R4 in the compounds of formula (I) are, in any combination thereof, as set out below,
R1 is methyl.
R2 is hydrogen.
R3 is hydrogen.
R4 is Cs-Cïcycloalkyl.
Préférably, 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 (2)-2-(5-cyclopropyi-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), as defined in Table X below.
More preferably, component (A) is a compound selected from, methyl (Z)-2-(5-cyclopentyi-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), as defined in Table X below.
In one embodiment component (A) is methyl (2)-2-(5-cyciopentyl-2-methyl-phenoxy)-3-methoxy-prop2-enoate (compound X.02).
In another embodiment component (A) is methyl (2)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy~ 5 prop-2-enoate (compound X.04).
Table X
Compound number Compound structure 1UPAC name
X.01 °xr methyl (2)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxy-prop-2-enoate
X.02 xo methyl (2)-2-(5-cyctopentyl-2-methyl- phenoxy)-3-methoxy-prop-2-enoate
X.03 1¾ /°Λ 1________ meth yI (2)-2- (5-cyc[opropyl-2-methylphenoxy)-3-methoxy-prop-2-enoate
X.04 methyl (2)-2-(5-cyciohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate
Component (B) is a compound seiected from the group consistîng of:
bixafen, sulfur, copper hydroxide, triclopyrîcarb, acîbenzolar-S-methyl, copper oxychloride, cyproconazole, difenoconazole, epoxicon-azole, flutriafol, hexaconazole, ipconazole, metconazole, paciobutrazole, prothioconazole, prochloraz, propiconazole, pyrisoxazole, tebucon-azole, fenpropidin, fenpropimorph, spiroxamine, cyprodinil, fludioxonil, metalaxyi, metaiaxyl-M (mefenoxam), carbendazim, penthiopyrad, azoxystrobin, dimoxystrobin, fenammstrobm, flufenoxystrobin, fluoxastrobin, metomi-nostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxy St robin, mancozeb, folpet, chlorothaionii, fluazinam, fluxapyroxad, fenhexamid, fos-etyfaluminium, pyribencarb, tricyclazole, mandipropamid, flubeneteram, isopyrazam, sedaxane, benzovindifiupyr, pydiflumetofen, isoflucypram, isotianil, dipymetitrone, fluindapyr, coumethoxystrobin (jiaxiangjunzhi), Ivbenmixianan, mandestrobin, oxathiapiprolin, pyraziflumid, inpyrfluxam, mefentrifluconazole, ipfentrifluconazoie, aminopyrifen, (Z,2E)-5-[1-(4-chiorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-di!Tiethyf-pent-3-enamide, floryipicoxamid, fenpicoxamid, ipflufenoquin, quinofumelin, benzothiostrobin, fluopyram, pyrapropoyne, 2-(difiuoromethyl)-N-(3-ethyl·1,1-dimethylindan-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol1-yl)propyl]-3-pyridyl]oxy]benzonîtrile, metyltetra proie, fluoxapiprolin, enoxastrobin, 4-((6-(2-(2,4difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thloxo-4H-1,2,4-triazo!-1-yl)propylj-3pyridyt]oxy]benzonîtrile, trinexapac, trinexapac-ethyl, coumoxystrobin, N'-[5-bromo-2-methyl-6-[(1S)-1methyl-2-propoxy-ethoxy]-3-ρyΓidyl]-N-ethyl·N-methyl-formamidiπe, N'-[5-bromo-2-methyl-6-[(1 R)-1methyl-2-propoxy-ethoxy]-3-pyndyl]-N-ethyl-N-methyl-fomnamidine, N’-[5-bromo-2-methyl-6-(1-methyl2-propoxy-ethoxy)-3-pyridyl]-N-ethyl·N-methyl-formamidine, N'-[5-chlora-2-methyl-6-(1-methyl-2propoxy-ethoxy)-3-pyΓίdyl]-N-ethyl·N-methyl·formamidine, N’-[5-bromo-2-methy!-6-(1-methyl-2propoxy-ethoxy)-3-pyridylJ-N-iSOpropyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(2propoxypropoxy)-3-pyridyt]-N-ethyl-N-methyl-formamidine, N-isopropyl-N’-[5-nr)ethoxy-2-methyl-4(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-niéthyl-formamidine, N’-[4-(1-cyclopropyl-2,2,2trifluoro-1-hydΓoxy-ethyl)-5-Fnethoxy-2-methyl·phenyl]-N-isopropyl·N-methyl-formamidine, N-ethyi-N’[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-fomnamidine, N-ethyl-N’-[5methoxy-2-methyl-4-[2-trifuoronnethyl)tetrahydΓOfuran-2-yl]phenyl]-N-methy^-foΓmamidine1 N-(2fluorophenyl)-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(trifluoronnethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyi]propanamide, N-ethyi-2-methyl-N-[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyî]propanamide, [(1S,2S)-1-methyl-2-(o-toiyl)propy1] (2S)-2-[(4-methoxy-3'propanoyloxy-pyridine-2-carbonyl)aminûIpropanoate, 1-methoxy-3-methyl-1-([4' [5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyi]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyt)1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethy 1-1 -methoxy-1 -[[4-[5-(trifluoromethy 1)-1,2,4-oxadiazoL3yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yi]phenyl]methyl]propanamide, 4,4diπnethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol·3-yl3phenyl]methylJίsoxazo^idia-3-one, 5,5-dimethyl2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1 -[[4-[5(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]pher)yl]methyl]-1,2,4-triazof-3-amine, 2-[6-(4-chlorophenoxy)-2(trifluoromethyl)-3-pyndyl]-1 -(1,2,4-triazol-1 -yI)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)3-pyridyI]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonrtriie, 3-(2-(1-chlorocyclopropy!)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxypropyl]imidazole-4-carbonrtrrle, (4-phenoxyphenyl)methyl 2-amino-6-methyl·pyridine-3-carboxylate, Nmethyl-4-[5-(trîfluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; N-methyl-4-[520876 (trifIuoromethy[)-1,2,4-oxadîazol-3-yl]benzamide; (Z,2E)-5-[1-(2.4-dichlorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide, (5-methyl-2-pyridyl)-(4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazof-3yl]pheny!]methanone, ethyl 1-[[5-(5-(trifluoromethyi)-11214-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4carboxylate, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyllacetamide, Nj(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,214-oxadiazol-3-yl]benzamide, N-[N-methoxy-Cmethyl-carbonimidoyT4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide, N-[3-(4-chlorophenyi)-4,5dîhydroisoxazol-5-yl]-5-methyl-1,2]4-oxadiazole-3-carboxamide, 2-(difluoromethyl)-N-(1,1-dimethyl-3propyMndan-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-cart)onyl)amino}propanoate, [(1S,2S)-2-(4-fluoro-2-methylphenyi)-1,3-dimethyi-butyl] (2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2carbonyl]amino]propanoate, cis-jasmone, potassium phosphonate, calcium phosphonate, glyphosate (including the diammonium, isopropylammonium and potassium salts thereof), 2,4-D (including the choline sait and 2-ethylhexyl ester thereof), dicamba (including the aluminium, aminopropyl, bisaminopropylmethyl, choline, dichloroprop, digtycolamine, dîmethylamine, dimethylammonium, potassium and sodium saits thereof), glufosinate (including the ammonium sait thereof), thiamethoxam, cyclobutrifluram, isocycloseram, spiropidion, abamectin, emamectin, cyantraniliprole, chlorantranîliprole, diafenthiuron, broflanilide, 2-chloro-N-cyclopropyl-5-(1-{2,6-dichloro-4-[1,2,2,2tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}'1H-pyrazol-4-yl)-N-meîhylnicotinamide and fluxametamide.
Preferably component (B) is a compound selected from the group consrsting of, bixafen, sulfur, copper hydroxide, triclopyricarb, acibenzolar-S-methyl, copper oxychloride, cyproconazole, difenoconazole, epoxicon-azole, flutriafol, hexaconazole, ipconazole, metconazole, paclobutrazole, prothioconazoie, prochloraz, propiconazole, pynsoxazole, tebucon-azole, fenpropidin, fenpropimorph, spiroxamine, cyprodinil, fludioxonil, metalaxyl, metalaxyl-M (mefenoxam), 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, îsoflucypram, isotîanil, dipymetitrone, fluindapyr, coumethoxystrobin (jiaxiangjunzhi), Ivbenmixianan, 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, floryipicoxamid, fenpicoxamid, îpflufenoquin, quinofumelin, benzothiostrobin, fluopyram, pyrapropoyne, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yi)pyridine-3'Carboxamide, 4-[[6-[2-(2,4difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, metyltetraproie, fiuoxapiprolin, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydraxy-3-(5thioxo-4H-1,2,4-ίΓί3ζοΜ-γί)ρΓθργΙ]-3-ργπάγΙ]οχγ]5βπζοηίΐπΙθ, trinexapac, trinexapac-ethyl, coumoxystrobin, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine, N'-(5-bromo-2-methyl-6-[(1 R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl·N-methy^ formamidine, N'-[5-bromo-2-methyl-6-(1-methy^2-propoxy-ethoxy)-3-pyπdyl>N-ethyl-N-methylformamidine, N'-[5-chloro-2-methyl-6-(1-methy^2-propoxy-eihoxy)-3-pyπdyl]-N-ethyl-N-methylformamidine, N'-(5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidine, N'-[5-bromo-2-methyi~6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-fTnethyi-formamidine, Nisopropyl-N’-[5-methoxy-2-methyl-4-(2,2,2-trifIuoiO-1-hydiOxy-1-phenyl-ethyl)phenyl]-N-rTiethylformamidine, N’-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-Nisopropyl-N-methyl-formamidine, N-ethyl-N’-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2yllphenylJ-N-methyl-formamidine, N-ethyl·N'-[5-methoxy-2-methyl-4-[2-trifuoiΌmethyl)tetrahydrofuran2-yl]phenyl]-N-methyi-formamidine, N-methoxy-N4(4-[5-(trifluorornethyl)-1,2T4-oxadiazol-3yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(tnfluoromethyl)-1,2,4-oxadiazoî-3yl]phenyl]metbyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(triflLioromethyl)-1,2,4-oxadiazol-3yl]phenyl]methyl]propanamide, 1-methoxy-3-methy 1-1-((4-(5-(trifluoromethyl)-1,2,4-oxadîazol-3yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-eth yl-1 -methoxy-1 -[[4-[5-(trifIuoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5(trifluoromethyl)-l ,2,4-oxadiazoi-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethy 1-2-((4-(5(trifluoromethyl)-l ,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-3-amine, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3pyridyi]-1-(1,2,4-triazol-1-y!)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4triazol-1-yl)propan-2-ol, 3-(2-(1-chlorocyclopropyl)-3-(2-fIuorophenyl)-2-hydroxy-propyl]imidazole-4carbonitrile, 3-(2-(1 -chlorocyclopropyl)-3-(3-chk>ro-2-fluoro-phenyl)-2-hydroxy-propyl]innidazole-4carbonitrile, (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate, N-meth y 1-4-(5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; N-methyl-4-[5-(trifluoronnethyl)-1,2,4oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichloΓophenyi)pyrazol·3-yl]oxy-2-methoxy!mino-N,3dimethyl-pent-3-enamide, (5-methyf-2-pyrîdyl)-[4-£5-(trïfluoromethyl)-1,2,4-oxadiazol-3yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromeÎhyl)-1,2,4-oxadiazol-3yl]phenyl]methanone, ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadîazol-3-yl]-2-thienyl]methyi]pyrazole-4carboxylate, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyi]acetamide, N[(Z)-methoxyiminomethyl]-4-[5-(trifiuoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-(N-methoxy-Cmethyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamtde, N-[3-(4-chlorophenyl)-4,5dihydroisoxazol-5-yl]-5-methyl-1,2,4-oxadiazole-3-carboxamide, 2-(difluoromethyl)-N-(1,1-dimethy1-3propyl-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-methylphenyl)-1,3-dimethyl-butyl] (2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2carbonyl]amino]propanoate, cis-jasmone, potassium phosphonate, calcium phosphonate, glyphosate (including the diammonium, isopropylammonium and potassium salts thereof), 2,4-D (including the choline sait and 2-ethylhexyl ester thereof), dicamba (including the aluminium, aminopropyl, bisamînopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts thereof), glufosinate (including the ammonium sait thereof), thiamethoxam, k 9 cyclobutrifluram, isocycloseram, spiropidion, abamectin, emamectin, cyantraniliprole, chlorantraniliprole, diafenthiuron, broflanilide, 2-chloro-N-cyclopropyl-5-(1-{2,6-dichloro-4-[1,2,2,2tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-1H-pyrazol-4-yl)-N-methylnÎcotinamide and fluxametamide.
More preferably, component (B) is a compound selected from the group consisting of, bixafen, trïclopyricarb, cyproconazoie, difenoconazole, epoxicon-azole, flutriafol, hexaconazole, ipconazole, metconazole, prothioconazole, propiconazole, tebucon-azole, azoxystrobin, dimoxystrobin, fenaminstrobin, flufenoxystrobin, fluoxastrobin, metomi-nostrobin, trifloxystrobîn, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, mancozeb, chlorothalonil, fluxapyroxad, 10 pyribencarb, benzovindiflupyr, isoflucypram, coumethoxystrobin (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, metyltetra proie, enoxastrobin, coumoxystrobin, 2-[6-(4-chlorophenoxy)-2-(trifIuoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yi)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(tnfluoromethyi)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-(2-(1 chlorocyclopropyl)-3-(2-f1uorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile and 3-[2-(115 chlorocyclopropyt)-3-(3-chloro-2-fluoro-phenyÎ)-2-hydroxy-propyl]imidazole-4-carbonitrile.
Even more preferably, component (B) is a compound selected from the group consisting of, cyproconazoie, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobîn, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluxapyroxad, benzovindiflupyr, 20 isoflucypram and metyltetraprole.
Yet even more preferably, component (B) is a compound selected from the group consisting of cyproconazoie, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobîn, picoxystrobin, pyraclostrobin and metyltetraprole.
Yet furthermore more preferably still, component (B) is a compound selected from the group consisting of cyproconazoie, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobîn, pyraclostrobin and metyltetraprole.
Furthermore preferably still, component (B) is azoxystrobin or trifloxystrobîn.
Most preferably, component (B) is azoxystrobin.
in one embodiment, component (B) is a compound selected from the group consisting of cyproconazoie, 35 difenoconazole, hexaconazole, prothioconazole, propiconazole, fenpropidin, fenpropimorph, fludioxonil, azoxystrobin, trifloxystrobîn, picoxystrobin, pyraclostrobin, mancozeb, folpet, chlorothalonil, fluxapyroxad, benzovindiflupyr, isoflucypram, pydifiumetofen, mefentrifluconazole, florylpicoxamid, metyltetraprole, N-(2-fluorophenyi)-4-[5-(trifluoromethy!)-1,2,4-oxadiazol-3-yl]benzamide and [(1 S,2S)1-methyl-2-(o-tolyi)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate.
Preferably, component (B) is a compound selected from the group consisting of cyproconazoie, difenoconazole, prothioconazole, fenpropidin, fenpropimorph, fludioxonif, azoxystrobin, trifloxystrobin, pyraclostrobin, mancozeb, folpet, chlorothalonil, benzovindiflupyr, pydiflumetofen, mefentrifluconazole, florylpicoxamid, metyltetra proie, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3yl]benzamide and [(1 S,2S)-1~methyl-2-(o-tolyi)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate.
The component (B) compounds are referred to herein and above by a so-called ISO commun name or another common name being used in individual cases or a trademark name. The component (B) compounds are known and are commercially available and/or can be prepared using procedures known in the art and/or procedures reported in the literature.
1n a preferred composition according to the invention component (A) is compound no. X.01 methyl (Z)2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop~2-enoate or a sait or tautomer thereof, and 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 (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, metyltetra proie, enoxastrobin, coumoxystrobin, 2-(6-(4chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-tnazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-tnazol-1-yl)propan-2-ol, 3-(2-(1-chlorocyclopropyl)-3-(2fluorophenyi)-2-hydroxy-propyl]imîdazole-4-carboniirile and 3-{2-(1-chîorocyclopropyl)-3-(3-chloro-2fluoro-phenyi)-2-hydroxy-propyl]imidazole-4-carbonitrite, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.
In another preferred composition according to the invention, component (A) is compound no. Χ.02 methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and 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 (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, metyltetra proie, enoxastrobin, coumoxystrobin, 2-(6-(4chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)2-(trifluoromethyf)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-(2-(1-ch lorocyclopropy 1)-3-(2fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile and 3-(2-(1 -chlorocyclopropyl)-3-(3-chloro-2fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.
In another preferred composition according to the invention, component (A) is compound no. X.03 methyi (Z)-2-(5-cyc!opropyl-2-methy!-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and 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 (jiaxiangjunzhi), mandestrobin, mefentriftuconazole, ipfentrifluconazole, benzothiostrobin, metyltetraprole, enoxastrobin, coumoxystrobin, 2-(6-(4ch]orophenoxy)-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-(2fiuorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2fluoro-phenyl)-2-hydroxy-propyl]imidazo!e-4-carbonitrile, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.
!n another preferred composition according to the invention, component (A) js compound no. X.04 methyi (Z)-2-(5-cyciohexyl-2-methyi-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and 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 (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, metyltetraprole, enoxastrobin, coumoxystrobin, 2-(6-(4chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl}-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-(6-(4-bromoph en oxy)2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-(2-(1-chlorocyclopropyl)-3-(2fluorophenyi)-2-hydroxy-propyl]imidazole-4-carbonitrile and 3-(2-(1-chlorocyclopropyl)-3-(3-chloro-2fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.
In a more preferred composition according to the invention component (A) is compound no. X.01 methyi (Z)-2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and 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, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.
In a more preferred composition according to the invention component (A) is compound no. X.02 methyi (Z)-2-(5-cyclopentyl·2-methyl-phenoxy)-3-methoxy-pΓop-2-enoate or a sait or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazofe, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin mancozeb, chlorothalonil, fluxapyroxad, benzovindiflupyr, isoflucypram and metyltetra proie, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.
In a more preferred composition according to the invention component (A) is compound no. X.03 methyl (Z)-2-(5-cyclopropyl-2-methyi-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and 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 metyltetraproie, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.
In a more preferred composition according to the invention component (A) is compound no. X.04 methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and 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 metyltetraproie, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.
In a preferred composition according to the invention component (A) is compound no. X.01 methyl (Z)2-(5-cyclobutyl·2-methyl·phenoxy)-3-methoxy-proρ-2-enoate or a sait or tautomer thereof, and component (B) is a compound selected from the group consisting of bixafen, triclopyricarb, cyproconazole, difenoconazole, epoxicon-azoie, 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 (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, metyltetraprole, enoxastrobin, coumoxystrobin, 2-(6-(4chlorophenoxy)-2-(trifluoromethyl)-3-pyridylï-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-chlorocyclopropy 1)-3-(2fluorophenyi)-2-hydroxy-propyl]imidazole-4-carbonitrile and 3-(2-(1-chlorocyclopropy l)-3-(3-chloro-2fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, wherein the weight ratio of component (A) to component (B) is from 10:1 to T.10 (oreven more preferably, 7.5:1 to 1:7.5).
In another preferred composition according to the invention, component (A) is compound no. X.02 methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and 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 (jîsxisngjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, metyltetraprole, enoxastrobin, coumoxystrobin, 2-(6-(4chlorophenoxy)-2-(trifluoromethyl)-3-pyridyJ]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)5 2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-(2-(1 -ch lorocyclopropy 1)-3-(2fluorophenyl)-2-hydroxy-propyÎ]imidazole-4-carbonitrile and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2fluoro-phenyl)-2-hydroxy-propyl]imidazote-4-carbo nitrite, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
In another preferred composition according to the invention, component (A) is compound no. X.03 methyl (Z)-2-(5-cyclopropyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and component (B) is a compound selected from the group consisting of bixafen, triclopyricarb, cyproconazole, difenoconazole, epoxîcon-azote, flutriafol, hexaconazole, ipconazole, metconazole, prothiocon azote, propiconazole, tebucon-azole, azoxystrobin, dimoxystrobin, fenaminstrobin, 15 flufenoxystrobin, fluoxastrobin, metomi-nostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, mancozeb, chlorothalonil, fluxapyroxad, pyribencarb, benzovindiflupyr, isoflucypram, coumethoxystrobin (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, metyltetraprole, enoxastrobin, coumoxystrobin, 2-(6-(4chlorophenoxy)-2-(trifluoromethyl)-3-pyridyll-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)20 2-(trifluoromethyt)-3-pyridyl]-1-(1l2,4-triazol-1-yl)propan-2-oi, 3-(2-(1-chlorocyclopropyl)-3-(2iluorophenyl)-2-hydroxy-propyl]imÎdazote~4-carbonitrite and 3-(2-(1 -chîorocyclopropyl)-3-(3-chloro-2fluoro-phenyl)-2-hydroxy-propyl]imidazote-4-carbonitrile, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
In another preferred composition according to the invention, component (A) is compound no. X.04 methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and 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, 30 flufenoxystrobin, fluoxastrobin, metomi-nostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, mancozeb, chlorothalonil, fluxapyroxad, pyribencarb, benzovindiflupyr, isoflucypram, coumethoxystrobin (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, metyltetraprole, enoxastrobin, coumoxystrobin, 2-(6-(4chlorophenoxy)-2-(trifluoromethyi)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-o(, 2-[6-(4-bromophenoxy)35 2-(trifluoromethyl)-3-pyridyî]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-(2-(1 -chlorocyclopropy 1)-3-(2fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrite and 3-(2-(1-chlorocyclopropyl)-3-(3-chloro-2fluoro-phenyl)-2-hydroxy-propyi]imidazole-4-carbonitrile, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
In a preferred composition according to the invention component (A) is compound no. X.ui methyl (Z)2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and component (B) is a compound selected from the group consistîng of cyproconazole, difenoconazole, hexaconazoie, prothioconazoie, propice nazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin maneozeb, chforothalonil, fluxapyroxad, benzovindiflupyr, isoflucypram and metyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
In another preferred composition according to the invention, component (A) is compound no. X.02 methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and component (B) îs a compound selected from the group consistîng of cyproconazole, difenoconazole, hexaconazoie, prothioconazoie, propiconazoie, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin maneozeb, chlorothalonil, fluxapyroxad, benzovindiflupyr, isoflucypram and metyltetraprole, wherein the weight ratio of component (A) to component (B) îs from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
In another preferred composition according to the invention, component (A) îs compound no. X.03 methyl (Z)-2-(5-cyclopropyl·2-methyl·phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and component (B) is a compound selected from the group consistîng of cyproconazole, difenoconazole, hexaconazoie, prothioconazoie, propiconazoie, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin maneozeb, chlorothalonil, fluxapyroxad, benzovindiflupyr, isoflucypram and metyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
în another preferred composition according to the invention, component (A) is compound no. X.04 methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and component (B) is a compound selected from the group consistîng of cyproconazole, difenoconazole, hexaconazoie, prothioconazoie, propiconazoie, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin maneozeb, chlorothalonil, fluxapyroxad, benzovindiflupyr, isoflucypram and metyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
In a preferred composition according to the invention component (A) is compound no, X.01 methyl (Z)2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and component (B) is a compound selected from the group consistîng of cyproconazole, difenoconazole, prothioconazoie, azoxystrobin, trifloxystrobin, pyraclostrobin and metyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
In another preferred composition according to the invention, component (A) is compound no. X.02 methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and component (B) is a compound selected from the group consisting ofcyproconazole, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobin, pyraclostrobin and metyftetraproie, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
In another preferred composition according to the invention, component (A) is compound no. X.03 methyl (Z)-2-(5-cyciopropyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobin, pyraclostrobin and metyltetraproie, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7,5:1 to 1:7.5).
In another preferred composition according to the invention, component (A) is compound no, X.04 methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a sait or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobin, pyraclostrobin and metyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
In one embodiment ofthe invention there is provided a synergistic fungicidal composition comprising a mixture of components (A) and (B) as active ingrédients, wherein component (A) is:
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-cyclopΓopyl-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 sait thereof;
and component (B) is a compound selected from the group consisting of:
cyproconazole, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobin, pyraclostrobin and metyltetraprole,
Preferably, in an embodiment of the invention there is provided a synergistic fungicidal composition comprising a mixture of components (A) and (B) as active ingrédients, wherein component (A) is: methyl (Z)-2-(5-cyclopentyl-2-meth yl-ph e noxy)-3-meth oxy-prop-2-en oate (compound X.02), or methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (compound X.04);
or an agronomically acceptable sait thereof;
and component (B) is a compound selected from the group consisting of: cyproconazole, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobin, pyraclostrobin and metyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
More preferably, in an embodiment ofthe invention there is provided a synergîsticfungicidal composition comprising a mixture of components (A) and (B) as active ingrédients, 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-metl^yl·phenoxy)-3-methoxy-prop-2-enαate (compound X.04);
or an agronomicafly acceptable sait thereof;
and component (B) is azoxystrobin ortrifloxystrobin. wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
Even more preferably, in an embodiment of the invention there is provided a synergistic fungicidal composition comprising a mixture of components (A) and (B) as active ingrédients, 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-cyclohexyi-2-methyl*phenoxy)-3-methoxy-prop-2-enoate (compound X.04);
or an agronomically acceptable sait thereof;
and component (B) rs azoxystrobin, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).
In another preferred embodiment ofthe invention there is provided a synergistic fungicidal composition comprising a mixture of components (A) and (B) as active ingrédients, 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 sait thereof;
and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothiocon azote, propiconazole, fenpropidin, fenpropimorph, fludioxonil, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobln, mancozeb, folpet, chlorothalonil, fluxapyroxad, benzovindiflupyr, isoflucypram, pydiflumetofen, mefentrifluconazoie, florylpicoxamid, metyltetra proie, N(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol·3-y(]benzamide and [(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate (preferably, wherein the weight ratio of component (A) to component (B) is from 100:1 to 1:100).
Preferably, in this embodiment of the invention there is provided a synergistic fungicidal composition comprising a mixture of components (A) and (B) as active ingrédients, 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 sait thereof; and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, prothioconazote, fenpropidin, fenpropimorph, fludioxonil, azoxystrobin, trifloxystrobin, pyraclostrobin, mancozeb, folpet, chlorothalonil, benzovindiflupyr, pydiflumetofen, mefentrifluconazole, florylpicoxamid, metyltetraproie, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-y!]benzamide and [(1S,2S)1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate, wherein the weight ratio of component (A) to component (B) is from 100:1 to 1:100 (preferably from 15:1 to 1:50, more preferably from 10:1 to 1:10)
The term fongicide” as used herein means a compound that Controls, modifies, or preventsthe growth of fungi. The term “fungicidally effective amount” means the quantîty of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi, Controlling or modifying effects include al! déviation from natural development, such as killing, retardation and the like, and prévention includes barrier or other défensive formation in or on a plant to prevent fungal infection,
The term “plants” refers to ail physical parts ofa plant, inciuding seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits,
The term plant propagation material dénotés ail generative parts of a plant, for example seeds or végétative parts of plants such as cuttings and tubers. it includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes, and parts of plants.
The term locus as used herein means frelds m or on which plants are growing, or where seeds of cultîvated plants are sown, or where seed will be placed into the soil. It includes soii, seeds, and seedlings, as well as established végétation.
Throughoutthis document the expression “composition” stands for the various mixtures or combinations of components (A) and (B) (including the above-defined embodiments), for example in a single “readymix” form, in a combined spray mixture composed from separate formulations of the single active ingrédient components, such as a “tank-mix, and in a combined use of the single active ingrédients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the components (A) and (B) is not essentiel for working the présent invention.
The composition according to the invention is effective against harmfui microorganisms, such as mîcroorganisms, that cause phytopathogenic diseases, in particular against phytopathogenic fungi and bacteria.
The composition ofthe invention may be used to control plant diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and/or Deuteromycete, Blasocladiomycete, Chrytidiomycete, Glomeromycete and/or Mucoromycete classes.
The composition is effective in controlling a broad spectrum of plant diseases, such as foliar pathogens of omamental, turf, vegetable, field, cereal, and fruit crops.
These pathogens may include:
Oomycetes, including Phytophthora diseases such as those caused by Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora cltricola, Phytophthora citrophthora and Phytophthora erythroseptica; Pythium diseases such as those caused by Pythium aphanidermatum, Pythium arrhenomanes, Pythium graminicoia, Pythium imegulare and Pythium ultimum; diseases caused by Péronés pora les such as Peronospora destructor, Peronospora parasitica, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cubensis, Albugo candida, Sclerophthora macrospora and Bremia lactucae; and others such as Aphanomyces cochtioides, Labyrinthuia zosterae, Peronosclerospora sorghi and Scierospora graminicoia;
Ascomycètes, including blotch, spot, biast or blight diseases and/or rots for example those caused by Pleosporales such as Stemphyiium solani, Stagonospora tainanensis, Spilocaea oleaginea, Setosphaeria turcica, Pyrenochaeta fycoperisici, Pieospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, Ophiosphaereila graminicoia, Ophioboius graminis, Leptosphaeria maculans, Hendersonia creberrima, Heiminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycioconium oleagineum,
Corynespora cassiicola, Cochliobolus sativus, Bipolaris c activera, Ventuna inaequahs, Pyrenophora tares, Pyrenophora triticFrepentis, Altemaha alternata, Altemaria brassicicoia, Altemaria soiani and Alternaria tomatophila, Capnodiales such as Septoria tritici, Septoria nodorum, Septoria glycines, Cercospora arachidicola, Cercospora sojina, Cercospora zeae-maydis, Cercosporelia capseilae and Cercosporella herpofrichoides, Cladosporium carpophîium, Cladosporium effusum, Passaiora fulva, Cladosporium oxysporum, Dothisfroma septosporum, Isanopsis clavispora, Mycosphaerella Ujiensis, Mycosphaerella graminicola, Mycovellosiella koepkeii, Phaeoisariopsis bataticola, Pseudocercospora vitis, Pseudocercosporella herpofrichoides, Ramufaria beticoia, Ramuiaria colio-cygni, Magnaporthales such as Gaeumannomyces graminis, Magnaporthe grisea, Pyricularia oryzae, Diaporthales such as Anisogramma anomala, Apiognomonia errabunda, Cytospora ptatani, Diaporthe phaseolorum, Discuta destructive, Gnomonia fructicola, Greeneria uvicola, Melanconium juglandinum, Phomopsis viticola, Sirococcus clavigignenti-juglandacearum, Tubakia dryina, Dicarpelia spp., Valsa ceratosperma, and others such as Actinothyrium graminis, Ascochyta pisi, Aspergilius flavus, Aspergillus fumigatus, Aspergillus nidulans, Asperisporium caricae, Blumeriella jaapii, Candide spp., Capnodium ramosum, Cephaloascus spp., Cephalosporium gramineum, Ceratocystis paradoxa, Chaetomium spp., Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum, Epidermophyton spp., Eutypa lata, Geotrichum candidum, Gibeilina cereaüs, Gioeocercospora sorghi, Gloeodes pomigena, Gloeosporium perennans; Gloeotinia temulenta, Griphospaeria corticola, Kabatiella Uni, Leptographium microsporum, Leptosphaerulinia crassiasca, Lophodermium seditiosum, Marssonina graminicola, Microdochium nivale, Monilinia fructicola, Monographella albescens, Monosporascus cannonbalius, Naemacycius spp., Ophiostoma novo-ulmi, Paracoccidioides brasiliensis, Pénicillium expansum, Pestalotia rhododendri, Petriellidium spp., Pezicuia spp., Phialophora gregata, Phyliachora pomigena, Phymatotrichum omnivora, Physatospora abdita, Plectosporium tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis, Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdocline pseudotsugae, Rhynchosporium secalis, Sacrocladium oryzae, Scedosporium spp., Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor, Sclerotium spp., Typhula ishikariensis, Seimatosporium mariae, Lepteutypa cupressi, Sepfocyta ruborum, Sphaceloma perseae, Sporonema phacidioides, Stigmina pafmivora, Tapesia yaliundae, Taphrina bullata, ThieMopsis basicoia, Trichoseptoria fructigena, Zygophiala jamaicensis; powdery mildew diseases for exampie those caused by Erysiphales such as Biumeria graminis, Erysiphe polygoni, Uncinuia necator, Sphaerotheca fuligena, Podosphaera leucotricha, Podospaera macularis Golovinomyces cichoracearum, Leveilluia taurica, Microsphaera diffusa, Oidiopsis gossypii, Phyllactinia guttata and Oidium arachidis-, moids for exampie those caused by Botryosphaeriales such as Dothiorefta aromatîca, Dipiodia seriata, Guignardia bidwellii, Botrytis cinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdaii, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, Phyilosticta cucurbltacearum', anthracnoses for example those caused by Glommerelaies such as CoHetotrichum gloeosporioides, Colietotrichum lagenarium, Colietotrichum gossypii, Glomereila cingulata, and Colietotrichum graminicola·, and wilts or blights for example those caused by Hypocreales such as Acremonium strictum, Claviceps purpurea, Fusarium culmorum, Fusarium graminearum, Fusarium virgutiforme, Fusarium oxysporum, Fusarium subglutinans, Fusarium oxysporum f.sp. cubense, Gerlachia nivale, Gibberella fujikuroi, Gibbereila zeae, Gliociadium spp., Myrothecium verrucaria, Nectria ramulariae, Trichoderma vîride, Tnchothecium roseum, and Verticillium theobromae;
Basidiomycetes, including smuts for example those caused by Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, rusts for example those caused by Pucciniales such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosponum ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia stniformis f.sp. Hordei, Puccinia stniformis f.sp. Secalis, Pucciniastrum coryli, or Uredinales such as Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopelia ampelosidis, Tranzscheiia discolor and Uromyces viciae-fabae; and other rots and diseases such as those caused by Cryptococcus spp., Exobasidium vexans, Marasmielfus inoderma, Mycena spp., Sphaceiotheca reffiana, Typhuia ishikanensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonie sotani, Thanetephorus cucurmeris, Entyloma dahiiae, Entylomella microspora, Neovossia moiiniae and Tilletia caries;
Blastocladiomycetes, such as Physoderma maydis;
Mucoromycetes, such as Choanephora cucurbitarum.; Mucorspp. : Rhizopus arrhizus; as well as diseases caused by other species and généra closely related to those listed above. In addition to their fungicidal activity, the compositions may also hâve activity against bacteria such as Erwinia amylovora, Envinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scabies and other related species as weil as certain protozoa.
The composition according to the invention is particularly effective against phytopathogenic fungi belonging to the following classes: Ascomycètes (e.g. Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula); Basidiomycetes (e.g. the genus Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); Fungi imperfecti (also known as Deuteromycetes; e.g. Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septorîa, Cercospora, Alternaria, Pyricularia and Pseudocercosporella); Oomycetes (e.g. Phytophthora, Peronospora, Pseudoperonospora, Albugo, Bremia, Pythium, Pseudosclerospora, Plasmopara).
Crops of useful plants in which the composition according to the invention can be used include perennial and annuai crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; fieid crops for example sugar and fodder beet, coffee, hops, mustard, oilseed râpe (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass; herbs such as basil, borage, chives, corsander, iavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees;
other trees, for example cacao, cocon ut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vin es for example grapes.
Crops are to be understood as being those which are naturally occurring, obtained by conventional 10 methods of breeding, or obtained by genetic engineering. They include crops which contain so-called output traits (e.g. improved storage stability, higher nutritîonal value and improved flavour).
Crops are to be understood as also including those crops which hâve been rendered tolérant to herbicides like bromoxynil or classes of herbicides such as ALS-, EPSPS-, GS-, HPPD- and PPO15 înhibitors. An example of a cropthat has been rendered tolérant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer canola. Examples of crops that hâve been rendered tolérant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.
Crops are also to be understood as being those which naturally are or hâve been rendered résistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include 525 endotoxins, végétative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi.
An example of a cropthat has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut® (Syngenta Seeds). An example of a crop comprising more than one gene that codes for 30 insecticidal résistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds). Crops or seed material thereof can also be résistant to multiple types of pests (so-called stacked transgenic events when created by genetic modification). For example, a plant can hâve the ability to express an insecticidal protein while at the same time being herbicide tolérant, for example Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).
The compounds of Formula (I) (including any one of compounds X.01 toX.04) orfungicidal compositions according to the présent invention comprising a compound of Formula (I) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) on soy bean plants.
In particular, transgenic soybean plants expressing toxins, for exampie insecticida! proteins such as deita-endotoxins, e.g, CrylAc (CrylAc Bt protein). Accordingly, this may include transgenic soybean plants comprising event MON87701 (see U.S. Patent No. 8,049,071 and related applications and patents, as well as WO 2014/170327 Al (eg, see paragraph [008] reference to Intacta RR2 PRO™ soybean)), event MON87751 (US. Patent Application Publication No. 2014/0373191) or event DAS81419 (U.S. Patent No. 8632978 and related applications and patents).
Other transgenic soybean plants may comprise event SYHT0H2 - HPPD tolerance (U.S. Patent Application Publication No. 2014/0201860 and related applications and patents), event MON89788 glyphosate tolerance (U.S. Pat. No. 7,632,985 and related applications and patents), event MON87708 -dicamba tolerance (U.S. Patent Application Publication No. US 2011/0067134 and related applications and patents), event DP-356043-5 - glyphosate and ALS tolerance (U.S. Patent Application Publication No. US 2010/0184079 and related applications and patents), event A2704-12 - glufosinate tolerance (U.S. Patent Application Publication No. US 2008/0320616 and related applications and patents), event DP-305423-1 - ALS tolerance (U.S. Patent Application Publication No. US 2008/0312082 and related applications and patents), event A5547-127 - glufosinate tolerance (U.S. Patent Application Publication No. US 2008/0196127 and related applications and patents), event DAS-40278-9 - tolerance to 2,4dichlorophenoxyacetic acid and aryîoxyphenoxypropionate (see WO 2011/022469, WO 2011/022470, WO 2011/022471, and related applications and patents), event 127 - ALS tolerance (WO 2010/080829 and related applications and patents), event GTS 40-3-2 - glyphosate tolerance, event DAS-68416-42,4-dfchlorophenoxyacetic acid and glufosinate tolerance, event FG72 - glyphosate and isoxaflutole tolerance, event BPS-CV127-9 - ALS tolerance and GU262 - glufosinate tolerance or event SYHT04R - HPPD tolerance.
The compounds of Formula (I) (including any one of compounds X.01 toX.04) orfungicidal compositions according to the présent invention comprising a compound of Formula (I) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizî) on soy bean plants. In particular, there are known in the scientific literature certain Elite soybean plant varieties where R-gene stacks, conferring a degree of immunity or résistance to spécifie Phakopsora pachyrhizi, hâve been been introgressed in the plant genome, see for example: “Fighting Asian Soybean Rust, Langenbach C, et al, Front Plant Science 7(797) 2016).
An elite plant is any plant from an elite line, such that an elite plant is a représentative plant from an elite variety. Non-iimiting examples of elite soybean varieties that are commercially available to farmers or soybean breeders include: AG00802, A0868, AG0902, A1923, AG2403, A2824, A3704, A4324, A5404, AG5903, AG6202 AG0934; AG1435; AG2031 ; AG2035; AG2433; AG2733; AG2933; AG3334; AG3832; AG4135; AG4632; AG4934; AG5831; AG6534; and AG7231 (Asgrow Seeds, Des Moines, lowa, USA); BPR0144RR, BPR 4077NRR and BPR4390NRR (Bio Plant Research, Camp Point, HL, USA); DKB1751 and DKB37-51 (DeKalb Genetics, DeKalb, 111., USA); DP 4546 RR, and DP 7870 RR (Delta & Fine
Land Company, Lubbock, Tex., USA); JG 03R501, JG 32R606C ADD and JG 55R503C (JGL Inc., Greencastle, Ind., USA); NKS 13-K2 (NK Division of Syngenta Seeds, Golden Valley, Minnesota, USA); 90M01,91M30, 92M33, 93M11,94M30, 95M30, 97B52, P008T22R2; P16T17R2; P22T69R; P25T51R; P34T07R2; P35T58R; P39T67R; P47T36R; P46T21R; and P56T03R2 (Pioneer Hi-Bred International, Johnston, lowa, USA); SG4771NRR and SG5161NRR/STS (Soygenetics, LLC, Lafayette, Ind., USA); S00-K5, S11-L2, S28-Y2, S43-B1, S53-A1, S76-L9, S78-G6, S0009-M2; S007-Y4; S04-D3; S14-A6; S20-T6; S21-M7; S26-P3; S28-N6; S30-V6; S35-C3; S36-Y6; S39-C4; S47-K5; S48-D9; S52-Y2; S58Z4; S67-R6; S73-S8; and S78-G6 (Syngenta Seeds, Henderson, Ky., USA); Richer (Northstar Seed Ltd. Alberta, CA); 14RD62 (Stine Seed Co. la., USA); orArmor4744 (Armor Seed, LLC, Ar., USA).
Thus, in a further preferred embodîment, fungicidal compositions according to the présent invention comprising a compound of formula (I) (including any one of compounds X.01 to X.04), are used to control Phakopsora pachyrhizi, (including fungicidally-résistant strains thereof, as outlined below) on Elite soybean plant varieties where R-gene stacks, conferring a degree of immunity or résistance to spécifie Phakopsora pachyrhizi, hâve been been introgressed in the plant genome. Nu mérous benefits may be expected to ensue from said use, e.g. improved biological activity, an advantageous or broader spectrum of activity (inc. sensitive and résistant strains of Phakopsora pachyrhizi), an increased safety profile, improved crop tolérance, synergistic interactions or potentiating properties, improved onset of action or a longer fasting residual activity, a réduction in the number of applications and/or a réduction in the application rate of the compounds and compositions required for effective control of the phytopathogen (Phakopsora pachyrhizi), thereby enabling bénéficiai resistance-management practices, reduced environmental impact and reduced operator exposure.
Under certain circumstances, fungicidal compositions according to the présent invention comprising a compound of Formula (!) when used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) on soy bean plants (in particular any of the transgenic soybean plants as described above), may display a synergistic interaction between the active ingrédients.
The fungicidal compositions according to the présent invention comprising a compound of formula (I) (including any one of compounds X.01 to X.04) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (in particular, Phakopsora pachyrhizi) on soybean plants.
Additionally, to date, no cross-resîstance has been observed between the fungicidal compositions according to the présent invention comprising a compound of formula (I) (including any one of compounds X.01 to X.04) and the current fungicidal solutions used to control Phakopsora pachyrhizi.
Indeed, fungicidal-resistant strains of Phakopsora pachyrhizi hâve been reported m the scientific literature, with strains résistant to one or more fungicides from at least each of the following fungicidal mode of action classes being observed: sterol demethylation-inhibitors (DMl), quinone-outside-inhibitors (Qo1) and succinate dehydrogenase inhibitors (SDHI). See for example: “Sensitivity of Phakopsora pachyrhizi towards quinone-outside-inhibitors and demethylation-inhibitors, and corresponding résistance mechanisms. Schmitz HK et ai, Pest Manag Sci (2014) 70: 378-388; “First détection of a SDH variant with reduced SDHI sensitivity in Phakopsora pachyrhizi' Simôes K et ai, J Plant Dis Prot (2018) 125: 21-2; “Compétitive fitness of Phakopsora pachyrhizi isolâtes with mutations in the CYP51 and CYTB genes. Klosowski AC et ai, Phytopathoiogy (2016) 106: 1278-1284; “Détection ofthe F129L mutation in the cytochrome b gene in Phakopsora pachyrhizi Klosowski AC et al, Pest Manag Sci (2016) 72:1211-1215.
Thus, in a preferred embodiment, the fungicidal compositions according to the présent invention comprising a compound of formula (I) (including any one of compounds X.01 toX.04), are usedto control Phakopsora pachyrhizi which are résistant to one or more fungicides from any ofthe following fungicidal MoA classes: sterol demethylation-inhibitors (DMl), quinone-outside-inhibitors (Qol) and succinate dehydrogenase inhibitors (SDHI).
The compounds comprising component A of the présent invention, wherein R1, R2, R3 and R4 are as defined for formula (I), can be made as shown in the following schemes.
The compounds of formula (I) wherein R’, R2, R3 and R4 are as defined above, can be obtained via cross coupling transformation between compounds of formula (II), wherein R1, R2 and R3 are as defined for compounds of formula (I) and R11 is a halide or pseudohalide such as chloro, bromo, iodo, -OSO2CF3 or-OSOatCFahCFs, and compounds of formula (III), wherein R4 is as defined for compounds of formula (I) and M is a metalloid species or pseudometailoid species (e.g. M includes but is not limited to MgCI, ZnCI or Β(ΟΗ)ζ), optionally in the presence of a métal sait such as LiCI or ZnCh, and a suitable meta! catalyst complex, such as chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1’-biphenyl)[2-(2'amino-1 ,T-biphenyl)]palladium(ll), in an organic solvent such as tetrahydrofuran or 1,4-dioxane at températures between 20°C - 150°C. For related examples, see: Journal of Organic Chemistry, 2010, 75, 6677 - 6680, Journal ofthe American Chemical Society, 2009, 131, 7532-7533, Européen Journal of Médicinal Chemistry, 2018, 147, 238-252, and “Cross-Couplîng Reactions: A Practical Guide (Topics in Current Chemistry), edited by Norio Miyaura und S. L. Buchwald (éditions Springer), or “MetalCatalyzed Cross-Coupling Reactions, edited by Armin de Meijere and François Diederich (éditions WILEY-VCH). This is shown in scheme 1.
Scheme 1
Alternative^ compounds of formula (I) can be obtained by reacting compounds of formula (IV), wherein 5 R1, R2 and R3 are as defined for compounds of formula (I) and R12 is a partially unsaturated, optionally substituted, Ca-Cycycloalkenyi, via a réduction method, such as hydrogénation using a hydrogen source in the presence of a catalyst compiex such as, palladium on carbon, in an organic solvent such as methanol, tetra hydroforan orethyl acetate at températures between O’C- 150°C. For related examples, see: ACS Médicinal Chemistry Letters, 2016 , 7, 508-51, 'Handbook of Heterogeneous Cataîytic 10 Hydrogénation for Organic Synthesis’ by Shigeo Nishimura (published by Wiley-VCH), or 'The
Handbook of Homogeneous Hydrogénation’ ed. Johannes de Vries and Cornelis Elsevier (published by Wiley-VCH). This is shown in scheme 2.
Scheme 2
Compounds of formula (IV), wherein R1, R2 and R3 are as defined for compounds of formula (I) and R12 is a partially saturated, and optionally substituted, Cs-Cvcycloalkenyi, can be obtained via a cross coupling reaction between compounds of formula (II), wherein R1’ is a halide or pseudohalide such as chloro, bromo, iodo, -OSO2CF3 or -OSOafCFîJsCFa, and compounds of formula (V), wherein M represents a metalloid or pseudometalloid species (e.g. M includes but is not limited to, B(OH)2, BPin, SnBus) or hydrogen. using a suitable catalyst compiex, such as palladium(tetrakistriphenylphosphine), in a solvent such as 1,4-dioxane, dimethylformamtde or tetrahydrofuran at températures between O’C 150°C, and optionally in the presence of a base (e.g. potassium phosphate). For related examples, see; ÂCS Médicinal Chemistry Letters, 2016, 7, 508-513 and Cross-Coupling Reactions: A Practical Guide (Topics in Current Chemistry)”, edited by Norio Miyaura and S.L. Buchwald (éditions Springer), or
LiMetal-Catalyzed Cross-Coupling Reactions”, edited by Amnin de Meijere and François Diederich (éditions WILEY-VCH). This is shown in scheme 3.
Scheme 3
Compounds of formula (II), wherein R1, R2 and R3 are as defined for compounds of formula (l) and R11 is a halide or pseudohalide such as chloro, bromo, iodo, -OSO2CF3 or-OS02(CF2)3CF3, can be obtained from compounds of formula (VI), wherein R1, R2 and R3 are as defined for compounds of formula (I), R11 is as defined above and R13 is H or Ci-CaS Ikyl, via treatment with a suitable base, such as sodium 10 methoxide, and a formylating agent, such as methyl formate, optionally in a suitable solvent (e.g.
tetrahydrofuran) to generate compounds of formula (Via), wherein R1, R2 and R3 are as defined for compounds of formula (I), R is as defined above and R14 is H or methyl, followed by méthylation with a reagent, such dimethyl sulfate, optionally in the presence of a base such as K2CO3. For related examples, see: Journal of Agriculture! and Food Chemistry, 2007, 55, 5697-5700, Molécules, 2010, 15, 15 9024-9034 and Organic Process Research and Development, 2015, 19, 639-645, This is shown in scheme 4.
(VI) (Via) (il)
Scheme 4
Compounds of formula (VI), wherein R1, R2 and R3 are as defined for compounds of formula (I), R’1 is as defined above and R13 is H orCi-C4 alkyl, can be obtained from compounds of formula (VII) wherein R’, R2 and R3 are as defined for compounds of formula (i) and R11 is as defined above, by treatment with a base such as K2CO3 and an alkylation agent of formula (VIII), wherein R13 is H or C1-C4 alkyl, in an organic solvent such asdimethylformamide or N-methyl pyrrolidone. Compounds of formula (VII) are
commercially avaiiable or readily prepared from commercially avaiiable compounds by standard functional group transformations as described in March’s Advanced Organic Chemistry, Smith and March, 6lh édition, Wiley, 2007. This is shown in scheme 5.
Scheme 5
Compounds of formula (I) wherein R1, R2, R3 and R4 are as defined for compounds of formula (I), can also be obtained from compounds of formula (IX) wherein R1, R3, R3 and R4 are as defined for 10 compounds of formula (I) and R13 is H orCi-C^ alkyl, by treatment with a base such as sodium methoxide and a formylating agent such as methyl formate to generate compounds of formula (X), wherein R1, R2, R3 and R4 are as defined for compounds of formula (I) and R14 is H or methyl, followed by méthylation with a reagent such dimethyl sulfate in the presence of a base such as K2CO3. For related examples, see: Journal of Agriculturai and Food Chemistry, 2007, 55, 5697-5700, Molécules, 2010, 15, 9024-9034 15 and Organic Process Research and Development, 2015, 19, 639-645. This is shown in scheme 6.
Scheme 6
Compounds of formula (IX), wherein R1, R3 and R3 are as defined for compounds of formula (I) and R4 is an optionally substituted cyclopropyl group, can be prepared from compounds of formula (XI), wherein R1, R2 and R3 are as defined for compounds of formula (i) and R15 represents an optionally substituted alkenyl group, by treatment with dnodomethane wrth an organozmc reagent such as diethyl zinc, optionally in the presence of an acid source, such as trifluoroacetic acid, and in an organic solvent such as dichloro methane. For related examples, see: Organic Reactions, 2001, 58, 1. This is shown in scheme 7.
Compounds of formula (XI), wherein R1, R2 and R3 are as defined for compounds of formula (I), R15is as defined above and R13 is H or Ci-C< alkyl, can be obtained from compounds of formula (XII) wherein R1, R2 and R3 are as defined for compounds of formula (I) and R15 is as defined above, by treatment with a base such as K2CO3 and an alkylation agent of formula (VIII), wherein R13 is H or C1-C+ alkyl, in an organic solvent such as dimethylformamide or N-methyl pyrrolidone, This is shown in scheme 8. For related examples, see: European Journal of Organic Chemistry, 2015, 2197-2204 Compounds of formula (VIII) are commerciaily available or readily prepared from commerciaily available compounds by standard functional group transformations as described in March’s Advanced Organic Chemistry, Smith and March, 6lh édition, Wiley, 2007.
Compounds of formula (XII), wherein R1, R2 and R3 are as defined for compounds of formula (I) and R15 is as defined above, can be prepared via coupling transformation between compounds of formula (VII), wherein R1, R2 and R3 are as defined for compounds of formula (I) and R11 is a halide or pseudohalide such aschloro, bromo, iodo, -OSOzCFa or-OSO2(CF2>3CF3, and compounds of formula (XIII), wherein R15 is as defined above and M represents a metalloid species or pseudometalloîd species (e.g. M includes but is not limited to, B(OH)2, BPin, SnBua) or hydrogen, usng a suitable catalyst compiex, such as palladium(tetrakistriphenylphosphine), in a suitable solvent such as dioxane, dimethylformamide or tetrahydrofuran at températures between 0°C - 150’C and optionally a base, such as potassium phosphate or potassium carbonate. For related examples, see: Journal of Médicinal Chemistry, 2015, 58, 9258-9272 and Journal of Médicinal Chemistry, 2014, 57,1252-1275.This is shown in scheme 9.
HO -, RHO + r15-m —*11 R>^>\R3pçjip
1212
RR (Vil)(XII)
Scheme 9
Functional group interconversions as described in the previous schemes are known to the persons skilled in the art. Extensive lists of reaction conditions can be found in: Comprehensive Organic Functional Group Transformations, Edited by A. R. Katritzky, O. Meth-Cohn and C. W. Rees. Pergamon Press (Elsevier Science Ltd.), Tarrytown, NY, 1995; or in: Comprehensive Organic Transformations: A Guide to Functional Group Préparations, Edited by Richard C. Larock, Wiley-VCH, New York 1999.
If the synthesis yields mixtures of isomers, a séparation is generally not necessarîly required because in some cases the individual isomère can be interconverted during work-up for use or during application (e.g, under the action of light, acids or bases). Such conversions may also take place after use, e. g, in the treatment of plants in the treated plant, or in the harmful fungus to be controlled.
Compositions of this invention, including all of the above disclosed embodiments and preferred examples thereof, can be mixed with one or more further pesticides including further fongicides, insecticides, nematocides, bactéricides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
Examples ofsuch agricultural protectants with which the composition of this invention can be fomiulated are:
Fungicides such as etridiazole, fluazinam, benalaxyl, benalaxyl-M (kiralaxyl), foralaxyl, metaiaxyl, metalaxyl-M (mefenoxam), dodicin, N'-(2,5-dimethyl-4-phenoxy-phenyl)'N'ethyl-N-methylformamidine, N’-[4-(4,5-dichlOΓO-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl·N-methyl-foΓmamidine, N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl forma midi ne, ethirimol, S'-chloro^-methoxy-N-KSRSHetrahydro^-oxofuran-S-ylJacet-^.S-xyhdtde (clozylacon), cyprodinil, mepanipyrim, pyrimethanil, dithianon, aureofungin, blasticidin-S, biphenyl, chloroneb, dicioran, benzovindiflupyr, pydiflumetofen, hexachlorobenzene, quintozene, tecnazene, (TC N B), 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, acibenzoiar, 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-(dffiuoromethyl)-N-(7-fiuoro-1,1,3,3-tetramethyf-rndan-4-yl)-1-methylpyrazole-4-carboxamide diclocymet, N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3(difluoromethyl)“54luoro-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, phosetyl-AI (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, fluoroimrde, mandipropamid, KSF-1002, benzamorf, dimethomorph, fenpropimorph, tridemorph, dodemorph, diethofencarb, fentin acetate, fentin hydroxide, carboxin, oxycarboxin, drazoxolon, famoxadone, mphenylphenol, p-phenylphenol, tribromophenol (TBP), 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6Îluoro-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-methy!cyclopropene, 4-CPA, chlormequat, clofencet, dichlorprop, dimethipin, endothal, ethephon, flumetralin, forchlorfenuron, gibberellic acid, grbberellins, hymexazol, maleic hydrazide, mepiquat, naphthalene acetamide, paclobutrazol, prohexadione, prohexadione-calcium, thidiazuron, tribufos (tributyl phosphorotrithioate), trinexapac, unîconazole, α-naphthaiene acetic acid, polyoxin D (polyoxrim), BLAD, chitosan, fenoxanil, folpet, 3-(difuoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4carboxamide, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, fenpyrazamine, diclomezine, pynfenox, boscalid, fluopyram, diflumetorim, fenarimol, 5-fluoro-2-(p tolylmethoxy)pyrimidin-4-amine ferimzone, dimetachlone (dimethaclone), pyroquiton, proquinazîd, ethoxyquin, quînoxyfen, 4,4,5-trifluoro-3,3-dimethyl-1-(3-quinolyl)isoquinoline, 4,4-difluoro-3,3dimethyf-1-(3-quinolyl)isoquinoline 5-fluoro-3,3,4,4-tetramethy!-1-(3-quinolyl)isoquinoline 9-fluoro-2,2dimethyl-5-(3-quinolyi)-3H-1,4-benzoxazepine, tebufloquin, oxolinic acid, chinomethionate 5 (oxythioquinox, quinoxymethionate), spiroxamine, (E)-N-methyl-2- [2- (2, 5-dimethylphenoxymethyl) phenyl]-2-methoxy-iminoacetamide, (mandestrobin), azoxystrobin, coumoxystrobin, dîmoxystrobin, enestroburin, enoxastrobin, fenamistrobin, tlufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metaminostrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, triclopyricarb, trifloxystrobin, amisulbrom, dîchlofluanid, tolylfluanid, 10 but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, dazomet, isotianil, tiadinil, thifluzamide, benthiazoie (TCMTB), silthiofam, zoxamide, anilazine, tricyclazole, (.+-.)-cis-1-(4-ch!orophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol (huanjunzuo), 1-(5bromo-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), azaconazole, bitertanol (biloxazol), 15 bromuconazole, ciimbazole, cyproconazole, difenoconazole, dimetconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, ipfentrifluconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetra conazo le, triadimefon, triadimenol, triazoxide, triticonazole, mefentrifluconazole, 2-(((1 R,5S)-5-[(420 fluorophenyl)methyl]-1-hydroxy-2,2-dimethyî-cydopentyl]methyî]-4H-1,2,4-triazoîe-3-thione, 2-((3-(2chloropheny 1)-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, chloropîcrin, cresol, daracide, dichlorophen (dichlorophene), difenzoquat, dipyrithione, N-(2-p-chlorobenzoylethyl)-hexaminium chloride, NNF-0721, octhilinone, oxasulfuron, 25 propamidine and propionic acid.
Insecticides such as abamectin, acephate, acetamiprid, amidoflumet (S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, buprofezin, carbofuran, cartap, chiorantranitiprole (DPX-E2Y45), chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, 30 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, fipronii, flonicamid, flubendiamide, flucythrinate, tau-fluvalinate, flufenerim (UR-50701), flufenoxuron, fonophos, halofenozide, hexaflumuron, hydramethylnon, imidacloprid, 35 indoxacarb, isofenphos, tufenuron, 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, pyridalyi, pyrifluquinazon, pyriprole, pyriproxyfen, rotenone, 40 ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen (BSN 2060), spirotetramat, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, trichlorfon and triflumuron;
Bactéricides such as streptomycin;
Acaricides such as amitraz, chinomethionat, chlorobenzilate, cyenopyrafen, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and
Biological agents such as Bacilfus thuringiensis, Bacilius thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.
Other examples of “reference mixture compositions are as foltows (wherein the term “TX represents a compound (according to the définition of component (A) ofthe compositions of the présent invention) selected from compound no. X.01, X.02, X.03 or X.04 as defined in the Table X above): a compound selected from the group of substances consisting of petroleum oils + TX, 1,1-bis(4-chloro-phenyl)-2ethoxyethanol + TX, 2,4-dichtorophenyl benzenesulfonate + TX, 2-fluoro-N-methyl-N-1naphthylacetamide + TX, 4-chlorophenyl phenyl sulfone + TX, acetoprole + TX, aldoxycarb + TX, amidithîon + TX, amidothioate + TX, amiton + TX, amiton hydrogen oxaiate + TX, amitraz + TX, aram'rte + TX, arsenous oxide + TX, azobenzene + TX, azothoate + TX, benomyl + TX, benoxa-fos + TX, benzyl benzoate + TX, bixafen + TX, brofenvalerate + TX, broflanilide + TX, bromo-cycien + TX, bromophos + TX, bromopropylate + TX, buprofezin + TX, butocarboxim + TX, butoxycarboxim + TX, butyl pyridaben + TX, calcium polysulfide + TX, camphechlor + TX, carbanolate + TX, carbophenothion + TX, cymiazole + TX, chino-methionat + TX, chlorbenside + TX, chlordimeform + TX, chlordimeform hydrochloride + TX, chlorfenethol + TX, chlorfenson + TX, chlorfensulfide + TX, chlorobenzilate + TX, chloromebuform + TX, chloromethiuron + TX, chloropropylate + TX, chiorthiophos + TX, cinerin I + TX, cinerin II + TX, cinerins + TX, closantel + TX, coumaphos + TX, crotamiton + TX, crotoxyphos + TX, cufraneb + TX, cyanthoate + TX, DCPM + TX, DDT + TX, demephion + TX, demephion-0 + TX, demephion-S + TX, demeton-methyl + TX, demeton-O + TX, demeton-O-methyl + TX, demeton-S + TX, demeton-S-methyl + TX, demeton-S-methylsulfon + TX, dichlofluanid + TX, dichlorvos + TX, dicliphos + TX, dienochlor + TX, dimefox + TX, dinex + TX, dinex-diclexine + TX, dinocap-4 + TX, dinocap-6 + TX, dinocton + TX, dino-penton + TX, dinosulfon + TX, dinoterbon + TX, dioxathion + TX, diphenyl sulfone + TX, disulfiram + TX, DNOC + TX, dofenapyn + TX, doramectin + TX, endothion + TX, eprinomectin + TX, ethoatemethyl + TX, etrimfos + TX, fenazaflor + TX, fenbutatin oxide + TX, fenothiocarb + TX, fenpyrad + TX, fen-pyroximate + TX, fenpyrazamlne + TX, fenson + TX, fentrifanil + TX, flubenzimine + TX, flucycloxuron + TX, fluenetil + TX, fluorbenside + TX, FMC 1137 + TX, formetanate + TX, formetanate hydrochloride + TX, formparanate + TX, gamma-HCH + TX, glyodin + TX, halfenprox + TX, hexadecyl cyclopropanecarboxylate + TX, isocarbophos + TX, jasmolin l + TX, jasmolin II + TX, jodfenphos + TX, lindane + TX, malonoben + TX, mecarbam + TX, mephosfolan + TX, mesulfen + TX, methacrifos + TX, methyl bromide + TX, metolcarb + TX, mexacarbate + TX, milbemycin oxime + TX, mipafox + TX, monocrotophos + TX, morphothion + TX, moxidectin + TX, naied + TX, 4-chloro-2-(2-chioro-2-methylpropyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, nifluridide + TX, nikkomycins + TX, nitrilacarb + TX, nîtrilacarb 1:1 zinc chloride complex + TX, omethoate + TX, oxydeproios + TX, oxydisuifoton + TX, pp'-DDT + TX, parathion + TX, permethrin + TX, phenkapton + TX, phosalone + TX, phosfoian + TX, phosphamidon + TX, polychloroterpenes + TX, polynactins + TX, proclonol + TX, promacyl + TX, propoxur + TX, prothidathion + TX, prothoate + TX, pyrethrin i + TX, pyrethrin II + TX, pyrethrins + TX, pyridaphenthion + TX, pyrimitate + TX, quinalphos + TX, quintiofos + TX, R-1492 + TX, phosglycin + TX, rotenone + TX, schradan + TX, sebufos + TX, selamectïn + TX, sophamide + TX, SSl121 + TX, sulfiram + TX, sulfluramid + TX, sulfotep + TX, sulfur + TX, diflovidazin + TX, tau-fluvalinate + TX, TEPP + TX, terbam + TX, tetradifon + TX, tetrasul + TX, thiafenox + TX, thiocarboxime + TX, thiofanox + TX, thîometon + TX, thioquinox + TX, thuringiensin + TX, triamiphos + TX, triarathene + TX, triazophos + TX, triazuron + TX, trifenofos + TX, trinactin + TX, vamidothion + TX, vaniliprole + TX, bethoxazin + TX, copper dioctanoate + TX, copper sulfate + TX, cybulryne + TX, dichlone + TX, dichlorophen + TX, endothal + TX, fentin + TX, hydrated lime + TX, nabam + TX, quinociamine + TX, quinonamîd + TX, simazine + TX, triphenyitin acetate + TX, triphenyltin hydroxide + TX, crufomate + TX, piperazine + TX, thiophanate + TX, chloralose + TX, fenthion + TX, pyridin-4-amine + TX, strychnine + TX, 1-hydroxy-1 H-pyridine-2-thione + TX, 4-(quinoxalin-2-ylamtno)benzenesu!fonamide + TX, 8hydroxyquinoline sulfate + TX, bronopol + TX, copper hydroxide + TX, cresol + TX, dipyrithione + TX, dodicin + TX, fenaminosulf + TX, formaldéhyde + TX, hydrargaphen + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, nickel bis(dimethyldithiocarbamate) + TX, nitrapyrin + TX, octhilinone + TX, oxolinic acid + TX, oxytetracycline + TX, potassium hydroxyquinoline sulfate + TX, probenazole + TX, streptomycin + TX, streptomycin sesquisulfate + TX, tecloftalam + TX, thiomersal + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, Amblyseius spp. + TX, Anagrapha falcifera NPV + TX, Anagrus atomus + TX, Aphelinus abdominalis + TX, Aphîdius colemani + TX, Aphidoletes aphidimyza + TX, Autographa californica NPV + TX, Bacillus sphaericus Neide + TX, Beauveria brongniartii + TX, Chrysoperla carnea + TX, Cryptolaemus montrouzieri + TX, Cydia pomonella GV + TX, Dacnusa sibirica + TX, Diglyphus isaea + TX, Encarsia formosa + TX, Eretmocerus eremicus + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hippodamia convergeas + TX, Leptomastix dactylopii + TX, Macrolophus caliginosus + TX, Mamestra brassicae NPV + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, Orius spp. + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilts + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, Trichogramma spp. + TX, Typhlodromus occidentalis + TX , Verticillium lecanii + TX, apholate + TX, bisazir + TX, busulfan + TX, dimatif + TX, hemei + TX, hempa + TX, metepa + TX, methiotepa + TX, methyi apholate + TX, morzid + TX, penfluron + TX, tepa + TX, thiohempa + TX, thiotepa + TX, tretamine + TX, uredepa + TX, (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E)-6methylhept-2-en-4-ol + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-11-en-1-yl acetate + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-icos-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (2)-tetradec-9-en-1-ol + TX, (Z)tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-tetradeca-9,11dien-1-yl acetate + TX, (9Z,12E)’tetradeca-9,12-dien-1-yl acetate + TX, 14-methyloctadec-1-ene + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one + TX, alpha-multistriatin + TX, brevicomin + TX, codlelure + TX, codlemone + TX, cuelure * TX, disparlure + TX, dodec-8-en-1-yl acetate + TX, dodec-9-en-1-yl acetate + TX, dodeca-8 + TX, 10-dien-1-yl acetate + TX, dominicalure + TX, ethyl 4-methyloctanoate + TX, eugenol + TX, frontaiin + TX, grandlure + TX, grandiure I + TX, grandlure II + TX, grandlure III + TX, grandlure IV + TX, hexalure + TX, ipsdîenol + TX, ipsenol + TX, japonilure + TX, lineatin + TX, litlure + TX, looplure + TX, mediure + TX, megatomoic acid + TX, methyl eugenol + TX, muscalure + TX, octadeca-2,13-dien-1-yl acetate + TX, octadeca-3,13-dien-1-yl acetate + TX, orfralure + TX, oryctalure + TX, ostramone + TX, siglure + TX, sordidin + TX, sulcatol + TX, tetradec-11-en-1-yl acetate + TX, trimedlure + TX, trimedture A + TX, trimedlure Bi + TX, trimedlure B2 + TX, trimedlure C + TX, trunc-call + TX, 2-(octylthio)-ethanol + TX, butopyronoxyl + TX, butoxy(polypropylene glycol) + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, diethyltoluamide + TX, dimethyl carbate + TX, dimethyl phthalate + TX, ethyl hexanediol + TX, hexamide + TX, methoquin-butyl + TX, methylneodecanamide + TX, oxamate + TX, picaridin + TX, 1-dichloro-1-nitroethane + TX, 1,1 -dichloro2,2-bis(4-ethylphenyl)-ethane + TX, 1,2-dichloropropane with 1,3-drchloropropene + TX, 1-bromo-2chloroethane + TX, 2,2,2-trichloro-1-(3,4-dichloro-phenyl)ethyi acetate + TX, 2,2-dichlorovinyl 2ethylsulfinylethyl methyl phosphate + TX, 2-(1,3-dithioian-2-yl)phenyl dimethylcarbamate + TX, 2<2butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyl diethyl phosphate + TX, 2-imidazolidone + TX, 2isovalerylindan-1,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate + TX, 2thiocyanatoethyl laurate + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-methyl-1-phenylpyrazol-5-yl dimethyl-carbamate + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate + TX, 5,5-dimethyî-3~ oxocyclohex-1-enyl dimethylcarbamate + TX, acethion + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX, allyxycarb + TX, alpha-ecdysone + TX, aluminium phosphide + TX, aminocarb + TX, anabasine + TX, athidathion + TX, azamethiphos + TX, Bacillus thuringiensis delta endotoxins + TX, barium hexafluorosiîicate + TX, barium polysulfide + TX, barthrin + TX, Bayer 22/190 + TX, Bayer 22408 + TX, beta-cyfluthrin + TX, beta-cypermethrin + TX, bioethanomethrin + TX, biopenmethrin + TX, bis(2chloroethyl) ether + TX, borax + TX, bromfenvinfos + TX, bromo-DDT + TX, bufencarb + TX, butacarb + TX, butathiofos + TX, butonate + TX, calcium arsenate + TX, calcium cyanide + TX, carbon disulfide + TX, carbon tetrachloride + TX, cartap hydrochloride + TX, cevadine + TX, chlorbicyclen + TX, chlordane + TX, chlordecone + TX, chloroform + TX, chloropicrin + TX, chlorphoxim + TX, chlorprazophos + TX, cis-resmethrin + TX, cismethrin + TX, clocythrin + TX, copper acetoarsenite + TX, copper arsenate + TX, copper oleate + TX, coumithoate + TX, cryolite + TX, CS 708 + TX, cyanofenphos + TX, cyanophos + TX, cyclethrin + TX, cythioate + TX, d-tetramethrin + TX, DAEP + TX, dazomet + TX, decarbofuran + TX, diamrdafos + TX, dicapthon + TX, dichlofenthion + TX, dicresyl + TX, drcyclanil + TX, dieldrin + TX, diethyl 5-methylpyrazol-3-yl phosphate + TX, dilor + TX, dimefluthrin + TX, dimetan + TX, dimethrin + TX, dimethylvinphos + TX, dimetilan + TX, dinoprop + TX, dinosam + TX, dinoseb + TX, diofenolan + TX, dioxabenzofos + TX, dithicrofos + TX, DSP + TX, ecdysterone + TX, El 1642 + TX,
EMPC + TX, EPBP + TX, etaphos + TX, ethiofencarb + TX, ethyl formate + TX, ethylene dibromide + TX, ethylene drchloride + TX, ethylene oxide + TX, EXD + TX, fenchlorphos + TX, fenethacarb + TX, fenitrothion + TX, fenoxacrim + TX, fenpirithrin + TX, fensulfothion + TX, fenthion-ethyl + TX, flucofuron + TX, fosmethilan + TX, fospirate + TX, fosthietan + TX, furathiocarb + TX, furethrin + TX, guazatine + TX, guazatine acétates + TX, sodium tetrathiocarbonate + TX, halfenprox + TX, HCH + TX, HEOD + TX, heptachlor + TX, heterophos + TX, HHDN + TX, hydrogen cyanide + TX, hyquincarb + TX, IPSP + TX, isazofos + TX, isobenzan + TX, isodrin + TX, isofenphos + TX, isolane + TX, isoprothiolane + TX, isoxathion + TX, juvénile hormone I + TX, juvénile hormone 11 + TX, juvénile hormone III + TX, kelevan + TX, kinoprene + TX, lead arsenate + TX, îeptophos + TX, lirimfos + TX, lythidathion + TX, m-cumenyl methylcarbamate + TX, magnésium phosphide + TX, mazidox + TX, mecarphon + TX, menazon + TX, mercurous chloride + TX, mesulfenfos + TX, metam + TX, metam-potassium + TX, metam-sodium + TX, methanesulfonyl fluoride + TX, methocrotophos + TX, methoprene + TX, methothrin + TX, methoxychtor + TX, methyl isothiocyanate + TX, methylchioroform + TX, methylene chloride + TX, metoxadiazone + TX, mirex + TX, naftalofos + TX, naphthalene + TX, NC-170 + TX, nicotine + TX, nicotine sulfate + TX, nithiazine + TX, nomicotine + TX, 0-5-dichtoro-4-todophenyl O-ethyl ethylphosphonothioate + TX, 0,0-diethyl 0-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate + TX, Ο,Ο-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate + TX, Ο,Ο,Ο',Ο'-tetrapropyl dithiopyrophosphate + TX, oleic acid + TX, para-dichlorobenzene + TX, parathion-methyl + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, PH 60-38 + TX, phenkapton +TX, phosnichlor + TX, phosphine + TX, phoxim-methyl + TX, pirimetaphos + TX, polychlorodicyclopentadiene isomers + TX, potassium arsenite + TX, potassium thiocyanate + TX, precocene I + TX, precocene U + TX, precocene III + TX, primidophos + TX, profluthrin + TX, promecarb + TX, prothiofos + TX, pyrazophos + TX, pyresmethrin + TX, quassia + TX, quinalphos-methyl + TX, quinothion + TX, rafoxanide + TX, resmethrin + TX, rotenone + TX, kadethrin + TX, ryania + TX, ryanodine + TX, sabadilla) + TX, schradan + TX, sebufos + TX, SI-0009 + TX, thiapronil + TX, sodium arsenite + TX, sodium cyanide + TX, sodium fluoride + TX, sodium hexafluorosilicate + TX, sodium pentachlorophenoxide + TX, sodium selenate + TX, sodium thiocyanate + TX: sulcofuron + TX, sulcofuron-sodtum + TX, sulfuryl fluoride + TX, sulprofos + TX, tar oils + TX, tazimcarb + TX, TDE + TX, tebupirimfos + TX, temephos + TX, terallethrin + TX, tetrachloroethane + TX, thicrofos + TX, thiocyclam + TX, thiocyclam hydrogen oxalate + TX, thionazin + TX, thiosultap + TX, thiosultap-sodium + TX, tralomethrin + TX, transpermethrin + TX, triazamate + TX, trichlormetaphos-3 + TX, trichloronat + TX, trimethacarb + TX, tolprocarb + TX, triclopyricarb + TX, triprene + TX, veratridine + TX, veratrine + TX, XMC + TX, zetamethrin + TX, zinc phosphide + TX, zolaprofos + TX, and meperfluthnn + TX, tetramethylfluthrin + TX, bis(tributyltin) oxide + TX, bromoacetamide + TX, ferrie phosphate + TX, niclosamide-olamine + TX, tributyltin oxide + TX, pyrimorph + TX, trifenmorph + TX, 1,2-dibromo-3-chloropropane + TX, 1,3-dichloropropene + TX, 3,4dichlorotetrahydrothio-phene 1,1-dioxide + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 5-methyl-6thioxo-1,3,5-thiadiazinan-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, 2-fluoro-N-(3methoxyphenyl)-9H-purin-6-amine + TX, benclothiaz + TX, cytokinins + TX, DCIP + TX, furfural + TX, isamidofos + TX, kinetin + TX, Myrothecium verrucaria composition + TX, tetrachlorothiophene + TX, xylenols + TX, zeatin + TX, potassium ethylxanthate + TX .acibenzolar + TX, acibenzolar-S-methyl +
TX, Reynoutria sachalinensis extract + TX, alpha-chlorohydrin + TX, antu + TX, barium carbonate + TX, bisthiosemi + TX, brodifacoum + TX, bromadiolone + TX, bromethalin + TX, chlorophacinone + TX, cholecalciferol + TX, coumachlor + TX, coumafuryl + TX, coumatetralyl + TX, crimidine + TX, difenacoum + TX, difethialone + TX, diphacinone + TX, ergocalciferol + TX, flocoumafen + TX, fluoraacetamide + TX, flupropadine + TX, flupropadine hydrochloride + TX, norbormide + TX, phosacetim + TX, phosphoms + TX, pindone + TX, pyrinuron + TX, scilliroside + TX, -sodium fluoroacetate + TX, thallium sulfate + TX, warfarin + TX, -2-(2-butoxyethoxy)ethyl piperonylate + TX, 5-(1,3-benzodioxol-5-yl)-3hexylcyclohex-2-enone + TX, famesol with nerolidol + TX, verbutin + TX, MGK 264 + TX, piperonyl butoxide + TX, piprotaI + TX, propyl isomer + TX, S421 + TX, sesamex + TX, sesasmolin + TX, sulfoxide + TX, anthraquinone + TX, copper naphthenate + TX, copper oxychloride + TX, dicyclopentadiene + TX, thiram <- TX, zinc naphthenate + TX, ziram + TX, imanin + TX, ribavirin + TX, chloroinconazide + TX, mercuric oxide + TX, thiophanate-methyi + TX, azaconazole + TX, bitertano! + TX, bromuconazole + TX, cyproconazole + TX, difenoconazole + TX, diniconazole -+ TX, epoxiconazole + TX, fenbuconazole + TX, fluquinconazole + TX, flusilazole + TX, flutriafol + TX, furametpyr + TX, hexaconazole + TX, imazaliî- + TX, imiben-conazole + TX, ipconazole + TX, metconazole + TX, myclobutanil + TX, paclobutrazole + TX, pefurazoate + TX, penconazole + TX, prothioconazole + TX, pyrifenox + TX, prochloraz + TX, propiconazole + TX, pyrîsoxazole + TX, -simeconazole + TX, tebucon-azole + TX, tetraconazole + TX, triadimefon + TX, triadimenol + TX, triflumizole + TX, triticonazole + TX, ancymidol + TX, fenarimol + TX, nuarimol + TX, bupirimate + TX, dimethirimol + TX, ethirimol * TX, dodemorph + TX, fenpropidin + TX, fenpropimorph + TX, spiroxamine + TX, tridemorph + TX, cyprodinii + TX, mepanipyrim + TX, pyrimethanil + TX, fenpiclonil + TX, fludioxonil + TX, benalaxyl + TX, furalaxyl + TX, -metalaxyl -+ TX, Rmetalaxy] + TX, ofurace + TX, oxadixyl + TX, carbendazim + TX, debacarb + TX, fuberidazole -+ TX, thiabendazole + TX, chlozolinate + TX, dichlozoline + TX, myclozoline- + TX, procymidone + TX, vinclozoline + TX, boscalid + TX, carboxin + TX, fenfuram + TX, flutolanil + TX, mepronil + TX, oxycarboxin + TX, penthîopyrad + TX, thifluzamide + TX, dodine + TX, iminoctadine + TX, azoxystrobin + TX, dimoxystrobin + TX, enestroburin + TX, fenaminstrobin + TX, flufenoxystrobin + TX, fluoxastrobin + TX, kresoxim-methyl + TX, metominostrobin + TX, trifloxystrobin + TX, orysastrobin + TX, picoxystrobin + TX, pyraclostrobin + TX, pyrametostrobin + TX, pyraoxystrobin + TX, ferbam + TX, mancozeb + TX, maneb + TX, metiram + TX, propineb + TX, zineb + TX, captafol + TX, captan + TX, fluoroimide + TX, folpet + TX, tolyîfluanid + TX, bordeaux mixture + TX, copper oxide + TX, mancopper + TX, oxine-copper + TX, nîtrothal-isopropyl + TX, edifenphos + TX, iprobenphos + TX, phosdiphen + TX, tolclofos-methyl + TX, aniiazine + TX, benthiavaticarb + TX, blasticidin-S + TX, chloroneb -+ TX, chloro-tha-ionil + TX, cyflufenamid + TX, cymoxanil + TX, cyclobutrifluram + TX, diclocymet + TX, diclomezine -+ TX, dicloran + TX, diethofencarb + TX, dimethomorph -+ TX, flumorph + TX, dithianon + TX, ethaboxam + TX, etridiazole + TX, famoxadone + TX, fenamidone + TX, fenoxanil + TX, ferimzone + TX, fluazinam + TX, fiuopicolide + TX, flusuifamide + TX, fluxapyroxad + TX, -fenhexamid + TX, fosetyl-aluminium -+ TX, hymexazol + TX, iprovalicarb + TX, cyazofamid + TX, methasulfocarb + TX, metrafenone + TX, pencycuron + TX, phthalide + TX, polyoxins + TX, propamocarb + TX, pyribencarb + TX, proquinazid + TX, pyroquilon + TX, pyriofenone + TX, quinoxyfen + TX, quintozene + TX, tiadinil + TX, triazoxide + TX, tricyclazole + TX, triforine + TX, validamycin + TX, valîfenalate + TX, zoxamide + TX, mandipropamid + TX, flubeneteram + TX, isopyrazam + TX, sedaxane + TX, benzovindiflupyr + TX, pydiflumetofen + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5’-trifluoro-biphenyl-2-yl)-amide + TX, isoflucypram + TX, isotianil + TX, dipymetitrone + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile + TX, 2-(difluoromethyl)-N-[3ethyl-1,1-dimethy1-indan-4-yl]pyridine-3-carboxamide + TX, 4-(2,6-difluorophenyl)-6-methyl·5-phenylpyridazine-3-carbonitrile + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4carboxamide + TX, 4-(2-bromo-4-fluoro-phenyl)-N-¢2-chloro-6-fluoΓO-phenyl)-2,5-dimethyl-pyrazol·3amine + TX, 4- (2- brome- 4- fluorophenyl) - N- (2- chloro- 6- fluorophenyl) -1,3- dimethyl-1 H- pyrazol5- amine + TX, fluindapyr + TX, coumethoxystrobin (jiaxiangjunzhi) + TX, ivbenmixianan + TX, dichlobentiazox + TX, mandestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1yl)quinolone + TX, 2-[2-fIuoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, oxathiapiprolin + TX, tert-butyl N-[6-[[[(1-methy itetrazol-5-yl)-phenyl-methylene]amino]oxy methy l]-2pyridyl]carbamate + TX, pyraziflumid + TX, inpyrflÎtxam + TX, trolprocarb + TX, mefentrifluconazole + TX, ipfentrifluconazole+ TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3carboxamide + TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyf-N-methyl-formamidine + TX, N’-[4-(4,5dichlorothiazol·2~yl)oxy-2,5-dimethyl·phenyl]-N-ethyl-N-methyl-foΓmamidine + TX, [2-[3-[2-[1-[2-[3,5bis(dif]uoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dîhydroisoxazol-5-yl]-3-chforophenyl) methanesulfonate + TX, but-3-ynyl N-[6-i[(Z)-[(1-methyltetrazol-5-yl)-phenylmethylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2yl]-2-methyl·phenyl]methyl]carbamate + TX, 3-ch loro-6-methyl-5-pheny 1-4-(2,4,6tnfiuorophenyl)pyridazine + TX, pyridachlometyl + TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, aminopyrifen + TX, ametoctradin + TX, amisuibrom + TX, penflufen + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyiminoN,3-dimethyl-pent-3-enamide + TX, florytpicoxamid + TX, fenpicoxamid + TX, tebufloquin + TX, ipfiufenoquin + TX, quinofumelin + TX, isofetamid + TX, N-[2-[2,4-dîchloro-phenoxy]phenyl]-3(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N-[2-[2-chloro-4(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-nnethyl-pyrazole-4-carboxannide + TX, benzothiostrobin + TX, phenamacril + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc sait (2:1) + TX, fluopyram + TX, flutianil + TX, fluopimomide + TX, pyrapropoyne + TX, picarbutrazox + TX, 2(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide + TX, 2- (difluoromethyl) N- ((3R) -1, 1,3- trimethylindan- 4- yl) pyridine- 3- carboxamide + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, metyltetraproie + TX, 2(difluoromethyl) - N- ((3R) - 1, 1, 3- trimethylindan- 4- yl) pyridine- 3- carboxamide + TX, a- (1, 1dimethylethyl) - a- [4- (trifluoromethoxy) [1, T- biphenylj - 4- yl] -5- pyrimidinemethanoi + TX, fluoxapiprolin + TX, enoxastrobin + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4triazol-1-yl)propyl]-3~pyridyl]oxy] benzonitrile + TX, 4-[[6-[2-(2,4-difluoropheny 1)-1,1-difluoro-2-hyd roxyS-fS-sulfanyl-I^A-triazol-l-ylipropyO-S-pyridylloxy] benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, trinexapac +
TX, coumoxystrobin + ΤΧ, zhongshengmycin + ΤΧ, thiodiazole copper + TX, zinc thiazole + TX, amectotractin + TX, iprodione + TX, N-octyl-N'-[2-(octylamino)ethyl]ethane-1,2-diamine + TX; N'-[5bramo-2-methyl-6-[<1S)-1-methyi-2-propoxy-ethoxy]-3-pyridyi]-N-ethyl-N-methyl-formamidine + TX, N'[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl·2-propoxy-etlΊoxy)-3-pyΓidyl]-N-ethyl·N-methy1-formamidine + TX, N’[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5bramo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds may be prepared from the methods described in WO2015/155075); N'-[5-bromo-2methyt-6-(2-propoxypropoxy)-3-pyridyi]-N-ethyl-N-methyl-formamidine + TX (this compound may be prepared from the methods described in IPCOM000249876D); N-isopropyl-N’-[5-methoxy-2-methyl-4(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyi)phenyl]-N-methyl-formamidine+ TX, N’-[4-(1-cyclopropyl2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds may be prepared from the methods described in WO2018/228896); N-ethyl-N’-[5methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + TX, N-ethyl-N’-[5methoxy-2-methyl-4-[2-trifuoromethyl)tetrahydrofuran-2-yl]phenyί]-N-methyl·formamidine + TX (these compounds may be prepared from the methods described in WO2019/110427); N-[(1 R)-1-benzyi-3chloro-Tmethyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-Tbenzyi-3,3,3-trifluoro-1-methyl· propyl]-8-fluoro-quînoline-3-carboxamide + TX, N-I(1S)-1-benzyl-3,3,3-trifluoro-1-methyi-propyl]-8fluoro-quinoline-3-carboxamide + TX, N-[(1 R)-1-benzyl-1,3-dîmethyl-butyl]-7,8-difluoro-quinoline-3carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyi]-7,8-difluoro-quinoline-3-carboxamide + TX, 8fluoro-N-KIRTI-KS-fluorophenyOmethyil-TS-dimethyl-butyllquirioline-S-carboxannide + TX, 8-fluoro-N[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyi-butyl]quinoline-3-carboxamide + TX, N-[(1 R)-1-benzyl1,3-dimethyl·butyl]-8-fiuOΓO-quίnoline-3-carboxaιnide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyi]-8fluoro-quinoline-3-carboxamide + TX, N-((1R)-1-benzyl-3-chforo-1-methyl-but-3-enyl)-8-fiuoroquinoline-3-carboxamide + TX, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fiuoro-quinoline-3carboxamide + TX (these compounds may be prepared from the methods described in WO2017/153380);
1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(6,7dimethylpyrazolo[1,5-a]pyridin-3-y!)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX, 4,4-difluoro-3,3dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yi)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-T(7methy)pyrazolo[1 .S-aJpyridin-S-ylJisoquinoline + TX, 1-(6-chloro-7-methyl-pyrazoio[1,5-a] py rid in-3-y I)4,4-difluoro-3,3-dimethy!-isoquinoline + TX (these compounds may be prepared from the methods described in WO2017/025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethylisoquinoline + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 6chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 4,4-difluoro-1-(5fluoro-4-methyl-benzimidazol-1-y!)-3,3-dimethyl-isoquino!ine + TX, 3-(4,4-difluoro-3,3-d!methyl-1isoquinolyi)-7,8-dîhydro-6H-cycJopentaIe]benzimidazole + TX (these compounds may be prepared from the methods described in WO2016/156085); [(1S,2S)-1-methyi-2-(o-tolyl)propyl] (2S)-2-[(3-hydroxy-4 methoxy-pyndine-2-carbonyl)amino]propanoate + TX, [(1S,2S)-1-methyl-2-(o-tolyi)propylJ (2S)-2-[(3acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + TX, [(1 S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyndine-2-carbonyt)amino]propanoate + TX, [(1 S,2S)-2-(4-fluoro2-methyl-phenyl)-1,3-dimethyl-butyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2carbonyl)amino]propanoate + TX, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl] (2S)-2-[(3acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + TX, [(1 S,2S)-2-(4-fIuoro-2-methyl-phenyl)1,3-dimethyl-butyl] (2S)-2-[(4-methoxy'3-propanoyioxy-pyridine-2-carbonyi)amino]propanoaÎe + TX, Nmethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl|cyclopropanecarboxamide + TX, N,2-dimethoxy-N-[[445-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-ethyl2-methyl-N4[4-[5-(trifluoromethyl)-1 ,214-oxadiazol·3-yl]pheίΊyl]methy^]propanamide + TX, 1 -methoxy-3methyl-1-[[4-[5-(trifluoromeihyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1,3-dimethoxy-1 -[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yi]phenyl]methyl]îjrea + TX, 3-ethyt-1-methoxy“1-[[4-[5(trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, N-[[4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]phenyl]methyÎ]propanamîde + TX, 4,4-dimethyl-2-[[4-I5-(trifluoromethyl)-1,2,4-oxadiazol3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3yl]phenyt]methyl]isoxazoiidin-3-one + TX, ethyl 1-[[4-[5-(trif!uoromethyi)-1,2,4-oxadiazo[-3y)]phenyi]methyl]pyrazoie-4-carboxyiate + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadtazol-3yl]phenyl]methyl]-1,2,4-triazol-3-amine + TX. The compounds in this paragraph may be prepared from the methods described in WO 2017/055473, WO 2017/055469, WO 2017/093348 and WO 2017/118689; 2-[6-(4-chlorophenoxy)-2-(trifiuoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound may be prepared from the methods described in WO 2017/029179); 2-[6-(4bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound may be prepared from the methods described in WO 2017/029179); 342-(1-chlorocyclopropyl)-3-(2fluoropheny1)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (this compound may be prepared from the methods described in WO 2016/156290); 3-[2-(1-chiorocyc!opropyl)-3-(3-chloro-2-fluoro-phenyi)-2hydroxy-propyl]imidazole-4-carbonitriie + TX (this compound may be prepared from the methods described in WO 2016/156290); (4-phenoxyphenyl)methyl 2~amino-6-methyl-pyridine-3-carboxylate + TX (this compound may be prepared from the methods described in WO 2014/006945); 2,6-Dimethyl1H,5H-[1,4]dithiino[2,3-c:5,6-c'ldipyrro!e-1,3,5,7(2H,6H)-tetrone + TX (this compound may be prepared from the methods described in WO 2011/138281); N-methyi-4-[5-(tnfIuoromethyl)-1,2,4-oxadiazol-3yl]benzenecarbothioamide + TX; N-methyl-4-[54trifluoromethyl)-1,2,4-oxadiazol-3-y[]benzamîde + TX; (Z,2E)-5-[1-(2,4~dichlorophenyi)pyrazol-3-yi]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX (this compound may be prepared from the methods described in WO 2018/153707); N'-(2-chloro-5methyl-4-phenoxy-phenyl)*N-ethyl-N-methyl-formamidine + TX; N'-[2-chloro-4-(2-fluorophenoxy)-5methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX (this compound may be prepared from the methods described in WO 2016/202742); 2-(difluoromethy!)-N-((3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3carboxamide + TX (this compound may be prepared from the methods described in WO 2014/095675); (5-methyL2-pyridylH4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX, (3 methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX (these compounds may be prepared from the methods described in WO 2017/220485); 2-oxo-N-propyl-2-[4[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX (this compound may be prepared from the methods described in WO 2018/065414); ethyl 1-[[5-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2thienyl]methyl]pyrazole-4-carboxylate + TX (this compound may be prepared from the methods described in WO 2018/158365) ; 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3yi]phenyl]acetamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2l4-oxadiazol-3yl]benzamide + TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[N-methoxy-C-methyl-carbonimidoyI]-4-[5-(trÎfluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX (these compounds may be prepared from the methods described in WO 2018/202428), a biostimulant comprising organic carbon, nutrients and amino acids (Quantis™) + TX.
The référencés in brackets behind the active ingrédients, e.g. [3878-19-1] refer to the Chemical Abstracts Registry number. The above described mixing partners are known. Where the active ingrédients are included in The Pesticide Manual (The Pesticide Manual - A World Compendium; Thrrteenth Edition; Editor: C. D. S. TomLin; The British Crop Protection Council], they are described therein under the entry number given in round brackets hereinabove for the particular compound; for example, the compound abamectin is described under entry number (1). Where [CCN] is added hereinabove to the particular compound, the compound in question is included in the Compendium of Pesticide Common Names, which is accessible on the internet [A. Wood, Compendium of Pesticide Common Names. Copyright © 1995-2004]; for example, the compound acetoprofe is described under the internet address http://www.alanwood.net/pesticides/acetoprole.html
Most ofthe active ingrédients described above are referred to hereinabove by a so-called common name, the relevant ISO common name or another common name being used in individual cases. If the désignation is not a common name, the nature ofthe désignation used instead is given in round brackets for the particular compound; in that case, the IUPAC name, the lUPAC/Chemical Abstracts name, a Chemical name, a traditional name, a compound name or a develoment code is used or, if neither one of those désignations nor a common name is used, an alternative name is employed. “CAS Reg. No” means the Chemical Abstracts Registry Number.
In the reference” mixture compositions the mixtures of compounds of formula (I) (selected from Table X (above)) with active ingrédients described above comprise a compound selected from Table X (above) and an active ingrédient as described above preferably in a mixing ratio of from 100:1 to 1:100, especially from 50:1 to 1:50, more especially in a ratio of from 20:1 to 1:20, even more especially from 10:1 to 1:10, yet even more especially from 7.5:1 to 1:7.5, very especially from 5:1 and 1:5, spécial preference being given to a ratio of from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 being likewise preferred, above ail in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. Those mixing ratios are by weight.
The mixture compositions as described above (both according to the ivnetion and the “reference mixture compositions) can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests ortheir environment.
The mixtures comprising a compound of formula (l) selected from Table X (above) and one or more 10 active ingrédients as described above can be applied, for example, in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingrédient components, such as a tank-mix”, and in a combined use of the single active ingrédients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. The order of applying the compounds of formula (I) selected from Table X (above) and the active 15 ingrédients as described above is not essential for working the présent invention.
The compositions ofthe présent invention may also be used in crop enhancement. According to the présent invention, ‘crop enhancement’ means an improvement in plant vigour, an improvement in plant quality, improved tolerance to stress factors, and/or improved input use efficiency.
According to the présent invention, an ‘improvement in plant vigour' means that certain traits are improved qualitatively or quantitatively when compared with the same trait in a control plant which has been grown under the same conditions in the absence of the method of the invention. Such traits indude, but are not limited to, early and/or improved germination, improved emergence, the ability to 25 use less seeds, increased root growth, a more developed root System, increased root nodulation, increased shoot growth, increased tillering, stronger tillers, more productive tillers, increased or improved plant stand, less plant verse (lodging), an increase and/or improvement in plant height, an increase in plant weight (fresh or dry), bigger leaf blades, greener leaf colour, increased pigment content, increased photosynthetic activity, earlierfiowering, longer panicles, early grain maturity, increased seed, 30 fruit or pod size, increased pod or ear number, increased seed number per pod orear, increased seed mass, enhanced seed filling, less dead basal leaves, deîay ofsenescence, improved vitality ofthe plant, increased levels of amino acids in storage tissues and/or less inputs needed (e.g. less fertiliser, water and/or labour needed). A plant with improved vigour may hâve an increase in any ofthe aforementioned traits or any combination ortwo or more ofthe aforementioned traits.
According to the présent invention, an ‘improvement in plant quality’ means that certain traits are improved qualitatively or quantitatively when compared with the same trait in a control plant which has been grown under the same conditions in the absence of the method of the invention. Such traits include, but are not limited to, improved visual appearance of the plant, reduced ethylene (reduced production and/or inhibition of réception), improved quality of harvested material, e.g. seeds, fruits, leaves, végéta blés (such improved quality may manifest as improved Visual appearance of the harvested material), improved carbohydrate content (e.g. increased quantifies of sugar and/or starch, improved sugar acid ratio, réduction of reducing sugars, increased rate of development of sugar), improved protein content, improved oil content and composition, improved nutritional value, réduction in anti-nutritionaI compounds, improved organoleptic properties (e.g. improved taste) and/or improved consumer health benefrts (e.g. increased levels of vitamins and anti-oxidants)), improved post-harvest characteristics (e.g. enhanced shelf-life and/or storage stabifity, easier processability, easier extraction of compounds), more homogenous crop development (e.g. synchronised germination, flowering and/or fruiting of plants), and/or improved seed quality (e.g. for use in following seasons). A plant with improved quality may hâve an increase in any ofthe aforementioned traits or any combination ortwo or more ofthe aforementioned traits.
According to the présent invention, an ‘improved tolerance to stress factors' means that certain traits are improved qualitatively or quantitatively when compared with the same trait in a control plant which has been grown under the same conditions in the absence ofthe method ofthe invention. Such traits include, but are not limited to, an increased tolerance and/or résistance to a biotic stress factors which cause sub-optimal growing conditions such as drought (e.g. any stress which leads to a lack of water content in plants, a lack of water uptake potentiai or a réduction in the water supply to plants), cold exposure, heat exposure, osmotic stress, UV stress, flooding, increased salinity (e.g. in the soit), increased minerai exposure, ozone exposure, high light exposure and/or limited availability of nutrients (e.g. nitrogen and/or phosphorus nutrients). A plant with improved tolerance to stress factors may hâve an increase in any ofthe aforementioned traits or any combination ortwo or more ofthe aforementioned traits. In the case of drought and nutrient stress, such improved tolérances may be due to, for example, more efficient uptake, use or rétention of water and nutrients.
According to the présent invention, an 'improved input use efficiency1 means that the plants are able to grow more effectively using given levels of in puis compared to the grown of control plants which are grown under the same conditions in the absence ofthe method ofthe invention. In particular, the inputs include, but are not limited to fertiliser (such as nitrogen, phosphorous, potassium, micronutrients), light and water. A plant with improved input use efficiency may hâve an improved use of any of the aforementioned inputs or any combination oftwo or more ofthe aforementioned inputs.
Other crop enhancements of the présent invention include a decrease in plant height, or réduction in tillering, which are bénéficiai features in crops or conditions where it is désirable to hâve less biomass and fewer tillers,
Any or ail of the above crop enhancements may lead to an improved yield by improving e.g. plant physiology, plant growth and development and/or plant architecture. In the context of the présent invention ‘yield’ includes, but is not limited to, (i) an increase in biomass production, grain yield, starch content, oil content and/or protein content, which may resuit from (a) an increase in the amount produced by the plant per se or (b) an improved ability to harvest plant matter, (ü) an improvement in the composition of the harvested material (e.g. improved sugar acid ratios, improved oil composition, increased nutritional value, réduction of anti-nutritionai compounds, increased consumer heaith benefits) and/or (iii) an increased/facilitated ability to harvest the crop, improved processability of the crop and/or better storage stability/shelf life. Increased yield of an agricultural plant means that, where it is possible to take a quantitative measurement, the yield of a product of the respective plant is increased by a measurable amount overthe yield ofthe same product ofthe plant produced underthe same conditions, but without application of the présent invention. According to the présent invention, it is preferred that the yield be increased by at least 0.5%, more preferred at least 1%, even more preferred at least 2%, still more preferred at least 4% , preferably 5% or even more.
Any or ail ofthe above crop enhancements may also lead to an improved utilisation of land, i.e. land which was previously unavailable or sub-optimal for cultivation may become available. For example, plants which show an increased ability to survive in drought conditions, may be able to be cuitivated în areas of sub-optimal rainfall, e.g. perhaps on the fringe of a desert or even the desert itself.
In one aspect of the présent invention, crop enhancements are made in the substantial absence of pressure from pests and/or diseases and/or abiotic stress. In a further aspect of the présent invention, improvements in plant vigour, stress tolérance, quality and/or yield are made in the substantial absence of pressure from pests and/or diseases. For example pests and/or diseases may be controlled by a pesticidal treatmentthat is applied prior to, or at the same time as, the method ofthe présent invention. In a still further aspect of the présent invention, improvements in plant vigour, stress tolérance, quality and/or yield are made în the absence of pest and/or disease pressure. In a further embodîment, improvements in plant vigour, quality and/or yield are made in the absence, or substantial absence, of abiotic stress.
The compositions of the present invention may also be used in the field of protecting storage goods against attack of fungi. According to the present invention, the term “storage goods” is understood to dénoté natural substances of vegetable and/or animal origin and their processed forms, which hâve been taken from the natural life cycle and for which long-term protection is desired. Storage goods of vegetable origin, such as plants or parts thereof, for example stalks, ieafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested State or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted. Also falling under the définition of storage goods is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form offinished articles, such as fumiture or objects made from wood. Storage goods of animal origin are hides, leather, furs, hairs and the like. The composition according the present invention can prevent disadvantageous effects such as decay, discoloration or mold. Preferably “storage goods” is understood to dénoté natural substances of vegetable origin and/or their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and cîtrus fruits and their processed forons. In another preferred embodiment of the invention “storage goods is understood to dénoté wood.
Therefore a further aspect of the présent invention is a method of protecting storage goods, which 5 comprises applyîng to the storage goods a composition according to the invention.
The composition of the présent invention may also be used in the fieid of protecting technical material against attack of fungi. According to the present invention, the terrn “technical material includes paper; carpets; constructions; cooling and heating Systems; wall-boards, ventilation and air conditioning 10 Systems and the like; preferably “technical material” is understood to dénoté wall-boards. The composition according the present invention can prevent disadvantageous effects such as decay, discoloration or mold.
The composition according to the invention is generally formulated in various ways using formulation 15 adjuvants, such as carriers, solvents and surface-active substances. The formulations can be in various physical forms, e.g. in the form of dusting powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrâtes, microemulsifiable concentrâtes, oil-in-water émulsions, oil-flowables, aqueous dispersions, oily dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrâtes 20 (with water or a water-miscible organic solvent as carrier), impregnated polymer films or in other forms known e.g. from the Manual on Development and Use of FAO and WHO Spécifications for Pesticides, United Nations, First Edition, Second Révision (2010). Such formulations can either be used directly or diluted prior to use. The dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.
The formulations can be prepared e.g. by mixing the active ingrédient with the formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or émulsions. The active ingrédients can also be formulated with other adjuvants, such as finely divided solids, minerai oils, oils of vegetable or animal origin, modified oils of vegetabte or animal origin, organic 30 solvents, water, surface-active substances or combinations thereof.
The active ingrédients can also be contained in microcapsules. Microcapsules contain the active ingrédients in a porous carrier. This enables the active ingrédients to be released into the environment in controlled amounts (e.g. slow-release). Microcapsules usually hâve a diameter of from 0.1 to 500 35 microns. They contain active ingrédients in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingrédients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrife, polyacrylate, polyesters, polyamides, poiyureas, potyurethane or chemicaHy modified 40 polymers and starch xanthates or other polymers that are known to the person skilled in the art.
Alternatively, veryfine microcapsules can be formed în which the active ingrédient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.
The formulation adjuvants that are suitable for the préparation of the formulations according to the invention are known per se. As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylène carbonate, chlorobenzene, cyciohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p10 diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, /V,/V-dimethylformamide, dimethyl sulfoxide, 1,4dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, alpha-pinene, d-fimonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol 15 methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesîtyl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, 20 oleylamine, o-xylene, phénol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, minerai oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, éthanol, îsopropanol, and alcohols of higher molecular weight, such as amyl alcohol, tetrahydrofurfuryl alcohol, 25 hexanol, octanol, ethylene glycol, propylene glycol, glycerol, /V-methyl-2-pyrrolidone and the like.
Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, sifica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.
A large number of surface-active substances can advantageously be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use. Surfaceactive substances may be an Ionie, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, 35 for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide addition Products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(240 ethylhexyl)sulfosuccinate; sorbitoi esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stéarate; biock copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkylphosphate esters; and also further substances described e.g. in McCutcheon's Détergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New Jersey (1981).
Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffets, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers.
The formulations according to the invention can include an additive comprising an oil of vegetable or animal origin, a minerai oil, alkyl esters of such oils or mixtures of such oils and oil dérivatives. The amount of oil additive in the formulation according to the invention is generally from 0.01 to 10 %, based on the mixture to be applied. For example, the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared. Preferred oil additives comprise minerai oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl dérivatives, or an oil of animal origin, such as fish oil or beeftallow. Preferred oil additives comprise alkyl esters of C8-C22 fatty acids, especially the methyl dérivatives of Ci2-Cts fatty acids, for example the methyl esters of iauric acid, palmitic acid and oleic acid (methyl laurate, methyl paimitate and methyl oleate, respectively). Many oil dérivatives are known from the Compendium of Herbicide Adjuvants, 10tr· Edition, Southern Illinois University, 2010.
The formulations generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of compounds of component (A) and component (B) and from 1 to 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance. Whereas commercial products may preferably be formulated as concentrâtes, the end user will normally employ dilute formulations.
The rates of application vary within wîde limits and dépend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. As a general guideline compounds may be applied at a rate of from 1 to 2000 l/ha, especially from 10 to 1000 l/ha.
Certain mixture compositions comprising a compound of formula (I) described above may show a synergistic effect. This occurs wheneverthe action of an active ingrédient combination is greater than the sum of the actions ofthe individual components. The action to be expected E for a given active ingrédient combination obeys the so-called COLBY formula and can be calculated as follows (COLBY, S.R. Calculating synergistic and antagonistic responses of herbicide combination. Weeds, Vol. 15, pages 20-22; 1967):
ppm = milligrams of active ingrédient (= a.i.) per iiter of spray mixture
X = % action by active ingrédient A) using p ppm of active ingrédient
Y = % action by active ingrédient B) using q ppm of active ingrédient.
According to COLBY, the expected (additive) action of active ingrédients A)+B) using p+q ppm of active ingrédient is:
If the action actually observed (O) is greater than the expected action (E), then the action of the combination is super-additive, i.e. there is a synergistic effect. In mathematical terms, synergism corresponds to a positive value forthe différence of (O-E). In the case of purely complementary addition of activities (expected activity), said différence (O-E) is zéro. A négative value of said différence (O-E) signais a loss of activity compared to the expected activity.
However, besides the actual synergistic action with respect to fungicidal activity, the composition according to the invention may also hâve further surprising advantageous properties. Examples of such advantageous properties that may be mentioned are: more advantageous degradability; improved toxicological and/or ecotoxicological behaviour; or improved characteristics of the useful plants including: emergence, crop yields, more developed root System, tilîering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf colour, less fertilizers needed, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigor, and early germination.
The composition according to the invention can be applied to the phytopathogenic microorganisms, the useful plants, the locus thereof, the propagation material thereof, storage goods or technical materials threatened by microorganism attack.
The composition according to the invention may be applied before orafter infection ofthe useful plants, the propagation material thereof, storage goods or technical materials by the microorganisms.
The amount of a composition according to the invention to be applied, will dépend on various factors, such as the compounds employed; the subject of the treatment, such as, for example plants, soil or seeds; the type of treatment, such as, for example spraying, dusting or seed dressing; the purpose of the treatment, such as, for example prophylactic or therapeutîc; the type of fungi to be controlled or the application time.
When applied to the useful plants component (A) is typically applied at a rate of 5 to 2000 g aJ./ha, particutarly 10 to 1000 g a.i./ha, e.g. 50, 75, 100 or 200 g a.i./ha, typically in association with 1 to 5000 g a.i./ha, particularly 2 to 2000 g a.i./ha, e.g. 100, 250, 500, 800, 1000,1500 g a.i./ha of component (B).
In agricultural practice the appiication rates ofthe composition according to the invention dépend on the type of effect desired, and typically range from 20 to 4000 g of total composition per hectare.
When the composition according to the invention is used for treating seed, rates of 0.001 to 50 g of a compound of component (A) per kg of seed, preferabiy from 0.01 to 10g per kg of seed, and 0.001 to 50 g of a compound of component (8), per kg of seed, preferabiy from 0.01 to 10g per kg of seed, are generally sufficient.
For the avoidance of doubt, where a literary reference, patent application, or patent, is cited within the text of this application, the entire text of said citation is herein incorporated by reference.
EXAMPLES
The Examples which follow serve to illustrate the invention.
The compounds (and compositions) ofthe invention may be distrnguished from known compounds (and compositions) by virtue of greater effîcacy 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 ingrédient (s).
Throughout this description, températures are given in degrees Celsius and “m.p.” means melting point LC/MS means Liquid Chromatography Mass Spectroscopy and the description ofthe apparatus and the methods is as follows:
Method G:
Spectra were recorded on a Mass Spectrometer from Waters (SQD, SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and négative ions), Capillary; 3.00 kV, Cône range: 30 V, Extractor: 2.00 V, Source Température: 150’C, Desolvation Température: 350°C, Cône 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 pm, 30 x2.1 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:
Spectra were recorded on a Mass Spectrometer from Waters (SQD, SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and négative ions), Capillary: 3.00 kV, Cône range: 3ÛV, Extractor: 2,00 V, Source Température: 150°C, Desolvation Température:
350^0, Cône 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 pm, 30 x 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 în 2.7 min; Flow (mL/min) 0.85
Where necessary, enantiomerîcalty pure final compounds may be obtained from racemic materials as appropriate via standard physical séparation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, eg, by using chiral starting materials.
Formulation Examples
Wettable powders a) b) c)
active ingrédients [components (A) and (B)] 25 % 50 % 75%
sodium lignosulfonate 5% 5% -
sodium lauryl sulfate 3 % - 5 %
sodium diisobutylnaphthalenesulfonate - 6% 10 %
phénol polyethylene glycol ether - 2% -
(7-8 mol of ethylene oxide)
highfy dispersed siiicic acid 5% 10 % 10%
Kaolin 62 % 27 % -
The active ingrédient is thoroughly mîxed with the adjuvants and the mixture is thoroughly ground in a 15 suitable mill, affording wettable powders that can be diluted with waterto givesuspensions ofthe desired concentration.
Powders for dry seed treatment a) b) C)
active ingrédients [components (A) and (B)] 25% 50% 75 %
light minerai oil 5% 5 % 5 %
highly dispersed siiicic acid 5% 5% -
Kaolin 65 % 40 % -
Talcum - - 20%
The active ingrédient 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.
Emulsifiable concentrate active ingrédients [components (A) and (B)] 10 % octylphenol polyethylene glycol ether 3 % (4-5 mol of ethylene oxide)
calcium dodecylbenzenesulfonate 3%
castor oil polyglycol ether (35 mol of ethylene oxide) 4 %
Cyclohexanone 30 %
xylene mixture 50 %
Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.
Dusts a) b) C)
active ingrédients [components (A) and (B)] 5 % 6 % 4%
talcum 95 % - -
Kaolin - 94 % -
minerai filler - - 96 %
Ready-for-use dusts are obtained by mixing the active ingrédient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
Extruder granules active ingrédients [components (A) and (B)] sodium lignosulfonate ca rboxy methylcel lulose Kaolin 15% 2% 1 % 82 %
The active ingrédient is mixed and g round with the adjuvants, and the mixture is moistened with water.
The mixture is extruded and then dried in a stream of air.
Coated granules active ingrédients [components (A) and (B)] 8 % polyethylene glycol (mol. wt. 200)
Kaolin
3%
89%
The finely ground active ingrédient is unifomnly applied, in a mixer, to the kaolin moistened with polyethylene giycol. Non-dusty coated granules are obtained in this manner.
Suspension concentrate active ingrédients [components (A) and (B)] propylene glycol nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) Sodium lignosulfonate ca rboxy methylcell u lose 40 % 10 % 6 % 10 % 1 %
silicone oil (m the form of a 75 % émulsion in water) %
Water
32%
The finely ground active ingrédient 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, tiving plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
Flowabie concentrate for seed treatment active ingrédients [components (A) and (B)] 40 % propylene glycol 5 % copolymer butanol PO/EO 2 % trîstyrenephenole with 10-20 moles EO 2 %
1,2-benzisothîazolin-3-one (in the form of a 20% solution in water) 0.5 % monoazo-pigment calcium sait 5 %
Silicone oil (in the form of a 75 % émulsion in water) 0.2 %
Water
45.3 %
The finely ground active ingrédient 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 parts of a combination ofthe active ingrédients [components (A) and (B)] is mixed with 2 parts of an aromatic solvent and 7 parts of toluenediisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1.2 paris of polyvinylalcohol, 0.05 parts of a defoamerand 51.6 parts of water until the desired particle size is achieved. To this émulsion a mixture of 2.8 parts 1,6diaminohexane in 5,3 parts of water is added. The mixture is agitated until the polymerization reaction is compieted. 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% ofthe active ingrédients. 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:
Aq. = aqueous br s = broad singlet CC = degrees Celsius
DCM = dichloromethane dd = doublet of doublet
DMP = dimethylformamide
DMSO - dimethyl suifoxide
DMSO-de = deuterated dimethyl suifoxide d = doublet
EtOAc = ethyl acetate equiv. = équivalent h = hour(s)
M = molar m = mulitpfet min = minutes
MHz = mega hertz mp = melting point
Pd2(dba)3 = tris(dibenzylideneacetone)dipalladium(0)
Pd(dppf)Ch DCM = [1,r-bis(diphenylphosphino)fenOcene]dichloropalladium(li), DCM complex Pd(PPh3)2Ch = bis(triphenylphosphine) palladium (II) dichloride ppm = parts per million
RT = room température
Rt = rétention time s = singlet t = triplet
THF = tetra hydrofuran
LC/MS = Liquid Chromatography Mass Spectrometry (description of the apparatus and the methods used for LC/MS analysis are given above)
X-Phos Pd G2 = chloro(2-dicyclohexyiphosphino-2',4',6'-triisopropyM ,1 '-biphenyl)[2-(2'-amino-1,1 biphenyl)]palladium(ll)
Préparation examples:
Example 1 : This example illustrâtes the préparation of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy) 3-methoxy-prop-2-enoate (compound X.04)
Steo 1 : Préparation of methyl 2-(5-bromo-2-methvl-phenoxv)acetaÎe
To a solution of 5-bromo-2-methy! phénol (53.47 mmol, 10.00 g) and methyi 2-bromo acetate (1.5 equiv., 80.20 mmol, 12.27 g, 7.44 mL) in tetrahydrofuran (0.5 mol/L, 106.9 mL) at room température 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 aiiowed to cool down to room température ovemight. 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 N32SO4, filtered and concentrated in vacuo to give methyi 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.
LCMS (Method H), Rt = 1.59 min, MS: (M+1) = 259, 261; 1H NMR (400 MHz, CDCIa) δ ppm 2.25 (s, 3 H) 3.84 (s, 3 H) 4.66 (s, 2 H) 6.84 (d, 1 H) 7.05 (m, 2 H)
Step 2: Préparation of methyi (Z)-2-(5-bromo-2-methvl-phenoxv)-3-methoxy-prop-2-enoate
Part 1: To a solution of 2-(5-bromo-2-methyl-phenoxy)acetate (20.8 g, 80.3 mmol) and methyi formate (6.0 equiv., 482 mmol, 29.5 g, 30.5 mL) in tetrahydrofuran (0.5 mol/L, 161 mL) at room température underargon 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 température water bath. The reaction mixture was stirred at room température for 1 h and quenched by the slow addition of an aqueous saturated solution of NaHCOs. 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 NaHCOs, brine, dried with Na2SO«, filtered and concentrated in vacuo to give methyl-2-(5-bromo-2methyl-phenoxy)“3-hydroxy-prop-2-enoate, which was taken directly to the next step without further purification.
LCMS (Method G), Rt = 0.80 and 0.90 min, MS: (M+1) = 287, 289
Part 2: To a solution of the crude methyl-2-(5-bronno-2-methyi-phenoxy)-3-bydroxy-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 roomtempérature under argon was added potassium carbonate (1.5 equiv., 117 mmol, 16.3 g), and the reaction mixture was stirred at room température 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 NaHCOs, brine, dried with Na2SO+, filtered and concentrated in vacuo.
The residue was purified by flash chromatography (cyclohexane: EtOAc) to give methyl (Z)-2-(5-bromo2-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; 1H NMR (400 MHz, CDCP) δ ppm 2.31 (s, 3
H) 3.74 (s, 3 H) 3.91 (S, 3 H) 6.86 (d, 1 H) 7.05 (m, 2 H) 7.35 (s, 1 H)
Step 3: Préparation of methyl (Z)-245-(cvclohexen-1-vl)-2-methvi-phenoxvl-3-methoxv-prop-2-enoate
To a solution of methyl (Z)-2-(5-bromo-2-methy1-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 réaction 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 NaHCOs solution then extracted with EtOAc. The total combined organic fraction was washed with and a saturated aqueous NaHCOs solution and brine, dried with NaaSO4, 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.
LC-MS (Method G), Rt = 1.17 min, MS: (M+H) = 303; 1H NMR (400 MHz, CDCh) 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: Préparation of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (Compound X.04)
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 atmosphère for 2 days. The réaction mixture was filtered over celite and concentrated in vacuo. The résultant crude residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl (Z)-2-(5-cyclohexyl2-methyl-phenoxy)-3-methoxy-prop-2-enoate as a white solid (mp: 131-132eC).
LC-MS (Method G), Ri = 1.21 min, MS: (M+H) = 305; ήΗ NMR (400 MHz, CDCls) 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 illustrâtes the préparation of methyl (Z)-2-(5-cyclopentyi-2-methyl-phenoxy)3-methoxy-prop-2-enoate (Compound X.02)
Under an argon atmosphère, a zinc chloride 1M THF solution (2.54 mmol) was added to a cyclopentyl magnésium 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-2methy1-phenoxy)-3-methoxy-prop-2-enoate (0.153 g, 0.51 mmol) in tetrahydrofuran (2.5 mL) and PdCh(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 NH4CI solution, and extracted with tert-butyf methylether. The total combined organic fraction was then washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure, The résultant 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).
LC-MS (Method G), Ri = 1.16 min, MS: (M+H) =291; Ή NMR (400 MHz, CDC h) Ô ppm: 7.35 (s, 1H), 7.09 (d, 1H), 6.82 (d, 1 H), 6.60 (s, 1H), 3.90 (s, 3H), 3.72 (s, 3H), 2.91 (m, 1 H), 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).
Using the synthetic techniques described both above and below, compounds of formula (I) may be prepared accordingly.
Where necessary, enantiomerically pure final compounds may be obtained from racemic materials as appropriate via standard physical séparation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, (eg, by using chiral starting materials).
Table Tl: Meltinq point (mp) data and/or rétention times (Rt) for compounds X.01 to X.04 according to formula (I):
Entry Compound structure Compound name Rt (min) Mass charge [M+H] LC MS Method mp (°C)
X.01 q< I methyl (2)-2-(5cycîobutyl-2methyl-phenoxy)3-methoxy-prop2-enoate 1.13 277 G
X.02 xo methyl (2)-2-(5cyclopentyl-2methyl-phenoxy)3-methoxy-prop2-enoate 80- 83
X.03 [x. methyl (2)-2-(5cyclopropyl-2methyl-phenoxy)3-methoxy-prop2-enoate 1.04 263 G
X.04 y/ CH methyl (2)-2-(5cyclohexyl-2methyl-phenoxy)3-methoxy-prop2-enoate 131- 132
BIOLOGICAL EXAMPLES:
General examples of leaf disk tests in weil plates:
Leaf disks or leaf segments of various plant species are eut from plants grown in a greenhouse, The eut 10 leaf disks or segments are piaced 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 (température, relative humidity, light, etc.) according to the respective test System. A single évaluation of disease level is carried out 3 to 14 days after inoculation, dependmg on the pathosystem. Percent disease control relative to the untreated check leaf disks or segments is then calculated.
General exemples of liquid culture tests in well plates:
Mycelia fragments or conidîa suspensions of a fungus prepared either freshly from liquid cultures ofthe fungus or from cryogénie 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 μΙ 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 darkat24°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 : Funqicidal activity against Puccinia recondita f. sp. tritici ! wheat / leaf dise preventative (Brown rust)
Wheat leaf segments are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. Afler 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.
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:
Compounds (from Table T1): X.01, X.02. X.03, X.04
Example A2: Funqicidal activity against Puccinia recondita f. sp. fripe//wheat / leaf dise curative (Brown rust)
Wheat leaf segments are placed on agar in multiwell plates (24-well format). The leaf segments are inoculated with a spore suspension ofthe 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.
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:
Compounds (from Table T1): X.01, X.02, X.04
Example A3: Fungicidal activity against Phakopsora pachyrhizi/ soybean i leaf dise preventative (Asian sovbean rust)
Soybean leaf disks are pîaeed 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 préventive fungicidal activity.
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:
Compounds (from Table T1 ): X.01, X.02. X.03, X.04
Example A4: Fungicidal activity against Glomerelia lacienarium (Colletotrichum lagenarium} liquid culture / cuGumber/ preventative (Anthracnose)
Conidia of the fungus from cryogénie 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 containîng 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 620nm. The following compounds gave at least 80% control of Glomerelia lagenarium at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development:
Compounds (from Table T1): X.01, X.02. X.03, X.04
Comparative Data:
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 Puccinie recondita (Brown rust), curative:
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.
The data are presented as the percentage of disease control of each compound for the biological tests 5 and testing rates described below in table B1.
Table B1 - Biological activity against Puccinia recondita (Brown rust), curative:
Compound Compound structure Concentration (ppm) control (%)
Compound X.04 V es ° \=/ X 200 100
60 100
20 90
Compound X.Û2 - 200 100
60 0
20 0
Reference Compound Z-1 (WO 98/03464) A > O K 200 0
60 0
20 0
Reference Compound Z-2 (EP 0 212 859) Cl , O. 200 0
60 0
20 0
Further biolgicaI test examples relating to fungicidal compositions comprising a mixture of components (A) and (B) as active ingrédients:
Example Cl Funqicidal activity against Mycosphaenella arachidis syn. Cercospora arachidicoia (Brown leaf spot)
Conidia of the tungus from cryogénie storage were directly mixed into nutrîent 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 5 incubated at 24 °C and the inhibition of growth was determined photometrically after approximately 5-6 days at 620nm
The following compound mixtures gave at least 80% control Mycosphaerelia arachidis at rates cited in the table when compared to untreated control under the same conditions, which showed extensive disease development:
Table C1-1 - Fungicidal activity > 80 % (% of untreated) against Mvcosohaereila arachidis
Component A Component B Ratio A: B Conc. (ppm) (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
Component A Component B Ratio A:B Conc. (ppm) (A: B)
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 fol pet 1 : 1 0.1 + 0.1
X.02 fol pet 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
Component A Component B Ratio A:B Conc. (ppm) (A : B)
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 oxy chloride 1 : 1 0.1 + 0.1
X.02 copper oxy chloride 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 isofiucypram 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
Component A Component B Ratio A:B Conc. (ppm) (A: B)
X.02 mefentrifluconazole 3 : 10 0.03 + 0.1
X.02 mefentrifluconazole 1 : 10 0.03 + 0.3
X.02 ipfiufenoquin 1 : 1 0.1 + 0.1
X.Û2 ipfiufenoquin 1 : 3 0.1 + 0.3
X.02 metyltetra proie 1 : 1 0.1 + 0.1
X.02 metyltetra proie 1 : 3 0.1 + 0.3
X.02 metyltetra proie 3 : 10 0.03 + 0.1
X.02 metyltetra proie 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-(trÎfluoromethyl)-3-pyridyf]-1(1,2,4-triazol-1-yl)propan-2-ol 1 : 1 0.1 + 0.1
X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1(1,2,4-triazol-1-yl)propan-2-ol 1 : 3 0.1 + 0.3
X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyi]-1(1,2,4-triazol-1-yl)propan-2-ol 3 ; 10 0.03 + 0.1
X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1(1,2,44riazol-1'yl)propan-2-ol 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-2methoxylmino-N,3-dimethyl-pent-3-enamide 1 : 1 0.1 + 0.1
X.02 (Z,2E)-5-[1'(2,4-djchlorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 3 0.1 + 0.3
X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2methoxyîmino-N,3-dimethyi-pent-3-enamide 3 : 10 0.03 + 0.1
X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 10 0.03 + 0.3
Component A Component B Ratio A: B Conc. (ppm)
(A: B)
X.02 {(1S.2S)-1-methy[-2-(o-tolyt)propyl] methoxy-3-propanoyloxy-pyridine-2carbonyl)ami no] propan oate (2S)-2-[(4- 50 : 3 1 + 0.06
X.02 [(IS^Sj-l-methyt-Z-Co-tolylÎpropyl] methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate (28)-2-((4- 25 : 3 0.5 + 0.06
X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] m et h oxy-3- p ro p a n oy loxy- p y rid î n e- 2carbonyl)amino]propanoate (2S)-2-[(4- 25 : 6 0.25 + 0.06
X.02 [(1 S,2S)-1 -methyl-2-(o-tolyl)propyl] methoxy-3-propanoy loxy-py rid in e-2carbonyl)amino]propanoate (2S)-2-[(4- 25 : 12 0.125 + 0.06
X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate (2S)-2-[(4- 25 : 24 0.0625+0.06
X.02 [(1 S,2S)-1 -methyl-2-(o-tolyl)propyl] methoxy-3-propanoyloxy-pyr!dine-2carbonyl)amino]propanoate (2S)-2-[(4- 25 : 48 0.03125+0.06
X.Û2 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate (2S)-2-[(4- 100 : 3 1 + 0.03
X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] methoxy-3-pro panoy loxy-py ridine-2carbonyl)amino]propanoate (2S)-2-[(4- 50 : 3 0.5 + 0.03
X.02 [(1S,2S)-1-methyt-2-(o-tolyl)propyl] methoxy-3-propanoyloxy-pyridîne-2carbonyl)amino]propanoate (2S)-2-[(4- 50 : 6 0.25 + 0.03
X.02 [(1 S,2S)-1 -methyi-2-(o-tolyl)propyl] methoxy-3-propanoyïoxy-pyridine-2carbonyl)amino]propanoate (2S)-2-[(4- 50 : 12 0.125 + 0.03
X.02 [(1 S,2S)-1 -methyl-2-(Otolyl)propyJ] methoxy-3-propanoyioxy-pyridine-2carbony!)amino]propanoate (2S)-2-[(4- 50 : 24 0.0625 + 0.03
X.02 [(1 S,2S)-1 -methyl-2-(o-tolyl)propyl] methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate (2S)-2-[(4- 50 : 48 0.03125+0.03
Component A Component B Ratio A:B Conc. (ppm) (A: B)
X.02 N-(2-fluoropheny!)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 20 1+20
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 40 0.5+20
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyJ)-1,2,4oxadiazol-3-yl]benzamide 1 : 80 0.25+20
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 160 0.125+20
X.02 N-(2-fluorophenyl)-4-[5-(tnfluoromethyl)-1,2,4oxadiazol-S-yObenzamide 1 : 320 0.0625+20
X.02 N-(2-ffuorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 10 1 + 10
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 20 0.5+10
X.02 N-(2-fluorophenyf)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yllbenzamide 1 : 40 0.25+10
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2I4oxadiazol-3-yl]benzamide 1 : 80 0.125+10
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 160 0.0625+10
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 C1-2 - Fungicidal activity > 80 % (% of untreated) against Mvcosphaerelia arachidis
Component A Component B Ratio A:B Conc. (ppm) (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
Component A Component B Ratio A:B Conc. (ppm) (A: B)
X.04 paclobutrazol 1 : 3 0,1 + 0.3
X.04 paclobutrazol 3 : 10 0.03 + 0.1
X.04 paciobutrazol 1 : 10 0.03 + 0.3
X.04 trinexapac-ethyf 1 : 1 0.1 +0.1
X.04 trinexapac-ethyi 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 fludioxonii 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 acibenzoiar S-methyl 1 : 1 0.1 +0.1
X.04 acibenzoiar S-methyl 1 : 3 0.1 +0.3
X.04 acibenzolar S-methyl 3 : 10 0.03 + 0.1
X.04 acibenzoiar 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
Component A Component B Ratio A:B Conc. (ppm) (A: B)
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 fiuopyram 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 copperoxychloride 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
Component A Component B Ratio A: B Conc. (ppm) (A: B)
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 quinofumeiin 1 : 1 0.1 +0.1
X.04 quinofumeîin 1 : 3 0.1 +0.3
X.04 quinofumeiin 3 : 10 0.03 + 0.1
X.04 quinofumeiin 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 metyltetra proie 1 : 1 0.1 + 0 1
X.04 metyltetra proie 1 : 3 0.1 +0.3
X.04 metyltetraprole 3 : 10 0.03 + 0.1
X.04 metyltetra proie 1 : 10 0.03 + 0.3
X.04 amlnopyrifen 1 : 1 0.1 +0.1
X.04 amrnopyrifen 1 : 3 0.1 +0.3
X.04 aminopyrifen 3 : 10 0.03 + 0.1
X.04 amlnopyrifen 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-(trifïuoromethyl)-3-pyridyl]1-(1,2,4-triazol-1-yi)propan-2-ol 1 : 1 0.1 +0.1
Component A Component B Ratio A:B Conc. (ppm)
(A: B)
X.04 2-[6- (4-bromophenoxy)-2-(trifluorornethyl)-3-pyridy Ο- Ι -(1,2,4-triazol-1-yl)propan-2-ol 1 : 3 0.1 +0.3
X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]- 1 -(1,2,4-triazol-1-yl)propan-2-ol 3 : 10 0.03 + 0.1
X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]- 1 -(1,2,4-triazol-1-yl)propan-2-ol 1 ; 10 0.03 + 0.3
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-dichiorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 1 0.1 + 0.1
X.04 (Z,2E)-5“[1-(2,4-dichlorophenyl)pyrazoi-3-yl]oxy-2methoxyimino-N,3-d!mettiyl-pent-3-enamide l : 3 0.1 + 0.3
X.04 (Z,2E)-5-[1-(2,4-dicfiiofophenyl)pyrazo!-3-yt]oxy-2methoxyimino-N,3-dimetfiyl-pent-3-enamide 3 : 10 0.03 + 0.1
X.04 (Z,2E)-5-[1-(2,4-dichloropfienyl)pyrazo!-3-yi]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 10 0.03 + 0.3
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate[(1 S,2S)-1-methyl-2-(o- tolyl)propyl] (2S)-2-[(4-methdxy-3-propanoyloxy- pyridine-2-carbonyî)amino]piOpanoate 10 : 3 0.2+0.06
X.04 [(1S,2S)-1-metfiyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate 5 : 3 0.1+0.06
X.04 E(1S,2S)-1-methyl-2-(o-tolyi)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate 5 : 6 0.05+0.06
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy’3-propanôyloxy-pyridine-2carbonyl)amino]propanoate 5 : 12 0.025+0.06
X.04 E(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate 5 : 24 0.0125+0.06
Component A Component B Ratio A: B Conc. (ppm)
(A: B)
X.04 [(1 S,2S)-1 -methyl-2-(o-tolyl)propyl] methoxy-3-propanoyloxy-pyridine-2carbony!)amino]propanoate (2S)-2-[(4- 5 : 48 0.00625+0.06
X.04 [(1 S,2S)-1-methyl-2-(o-tolyl)propyl] methoxy-3-propanoyloxy-pyridine-2carbonyl)aminojpropanoate (2S)-2-[(4- 20 : 3 0.2+0.03
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] methoxy-3-propanoyloxy-pyrîdine-2carbonyl)amino]propanoate (2S)-2-[(4- 10 : 3 0.1+0.03
X.04 ((1 S,2S)-1 -methyl-2-(o-tolyl)propyl] methoxy-3-pro pa noy loxy- py ridine-2carbonyl)amino]propanoate (23)-2-((4- 10 : 6 0.05+0.03
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl) methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate (2S)-2-[(4- 10 ; 12 0.025+0.03
X.04 [(1 S,2S)-1 -methyl-2-(o-tolyl)propyl] methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate (2S)-2-[(4- 10 : 24 0.0125+0.03
X.04 [(1 S,2S)-1-methyl-2-(o-tolyl)propyl] methoxy-3-propanoyloxy-pyridine-2carbonyl)amino)propanoate (2S)-2-[(4- 10 : 48 0.00625+0.03
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,214oxadiazol-3-yl]benzamideN-(2-fluorophenyl)-4-[5(tritluoromethyl)-l ,2,4-oxadiazol“3-yl] benzamid e 1 : 100 0.2+20
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazo!-3-yl]benzamide 1 : 200 0.1+20
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxad iazo l-3-y I] benzamid e 1 : 400 0.05+20
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 800 0.025+20
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 50 0.2+10
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl] benzamid e 1 : 100 0.1+10
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2I4oxadiazo!-3-yl]benzamide 1 : 200 0.05+10
Component A Component B Ratio A:B Conc. (ppm) (A: B)
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyi)-1,2,4oxadiazol-3-y1]benzamid e 1 ; 400 0.025+10
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+0.0 2
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+0.0 1
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 Mycosphaerelia arachidis syn. Cercospora arachidicoia (Brown leaf spot of peanut). Fungicidal activity was evaluated on a 100-0 scale (100 = no disease growth; 0 = wel! completely covered by mycélium).
Table C1-3
Component A Component B Conc. (ppm) Ratio A:B Activity (%) COLBY
(A: B) (expected 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
Component A Component B Conc. (ppm) Ratio A:B Activity (%) COLBY
(A: B) (expected activity %)
X.02 mancozeb 0.03 + 0.1 3 : 10 70 50
X.02 mancozeb 0.03 + 0.3 1 : 10 70 50
fol pet 0.3 20
X.02 fol pet 0.03 + 0.3 1 : 10 70 60
ipflufenoquin 0.3 0
X.02 ipflufenoquin 0.03 + 0.3 1 : 10 70 50
Table C1-4
Component A Component B Conc. (ppm) Ratio A: B Activity (%) COLBY
(A: B) (expected activity %)
X.04 0.0125 50
X.04 0.00625 0
[(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amîno]propanoate 0.03 70
X.04 [(lS,2S)-1-methyl-2-(o- tolyl)propyl] (2S)-2-[(4methoxy-3- propa noyloxypyridine-2carbonyl)amino]propanoate 0.0125+0.03 12 : 5 100 85
X.04 [(1S,2S)-1-methyl-2-(o- tolyl)propyl} (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.00625+0.03 24 : 5 100 70
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
Component A Component B Conc. (ppm) Ratio A:B Activity (%) COLBY
(A: B) (expected activity %)
X.02 0.03125 70
X.02 Florylpicoxamîd 0.03125+0.02 25:16 100 97
X.02 Florylpicoxamid 0.03125+0.01 25:8 100 85
Example C2 - Fungicidal activity against Seotoria tritici (leaf blotch)
Conidia of the fungus from cryogénie storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plaie (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 phoîometrically after 72 hrs.
The following compound mixtures gave at least 80% control Septoria tntici at rates cited in the table when compared to untreated control under the same conditions, which showed extensive disease development.
Table C2-1 - Fungicidal activity > 80 % (% of untreated) against Seotoria tritici
Component A Component B Ratio A:B Conc. (ppm) (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 propiconazoie 1 : 3 0.1 + 0.3
X.02 propiconazoie 1 : 10 0.03 + 0.3
X.02 hexaconazoie 1 : 1 0.1 + 0.1
X.02 hexaconazoie 1 : 3 0.1 + 0.3
X.02 hexaconazoie 3 : 10 0.03 + 0.1
X.02 hexaconazoie 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
Component A Component B Ratio A:B Conc. (ppm)
(A: B)
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 proth ioconazole 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
Component A Component B Ratio A:B Conc. (ppm)
(A: B)
X.02 isoflucypram 3 ; 10 0.03 + 0.1
X.02 isoflucypram 1 : 10 0.03 + 0.3
X.02 mefentriflucon azole 1 : 1 0.1 +0.1
X.02 mefentriflucon azote 1 : 3 0.1 +0.3
X.02 mefentriflucon azote 3 : 10 0.03 + 0.1
X.02 mefentriflucon azote 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 metyltetraprote 1 : 3 0.1 + 0.3
X.02 metyltetraprole 3 : 10 0.03 + 0.1
X.02 metyltetraprote 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-(trifluorometliyl)-3-pyridyl]-1(1,2T4-triazol-1-yl)propan-2-ol 1 : 1 0.1 + 0.1
X.02 2-[6-(4-bromophenoxy)-2-(trifluorometliyl)-3-pyridyi]-1(1,2,4-triazol-1-yl)propan-2-o! 1 ; 3 0.1 + 0.3
X.02 2-[6-(4-bromophenoxy)-2-(trifluoromettiyl)-3-pyridyl]-1(1,2,4-triazol-1-yl)propan-2-oi 3 : 10 0.03 + 0.1
X.02 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyf]-1(1,2,4-triazol-1-yl)propan-2-ol 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,2Ë)-5-[1-'(2,4-dichlorophenyl)pyrazol·3-yl]oxy-2methoxyfminc^-NΊ3-dίmethyl·pent-3-eπamide 1 : 1 0.1 +0.1
X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 3 0.1 +0.3
Component A Component B Ratio A:B Conc. (ppm) (A; B)
X.02 (Z,2E)-5-[1-(2,4-dichtorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 3 : 10 0.03 + 0.1
X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 10 0.03 + 0.3
X.02 Î(1S,2S)-1-methyl-2-(o-toiyl)propyl] (2S)-2-[(4-methoxy3-propanoyloxy-pyridine-2-carbonyl)amino]piOpanoate 50:3 1+0.06
X.02 ((1S,2S)-1-methyl-2-(o-tofyl)propyl] (2S)-2-[(4-methoxy3-propanoy loxy-py ridine-2-ca rbony 1) a mino]propanoate 25:3 0.5+0.06
X.02 [(IS^SJ-l-methyl-Z-io-tolyljpropyl] (2S)-2-[(4-methoxy- 3-propa noy loxy-py rid i n e-2-ca rbony 1) amino]pro pan oate 25:6 0.25+0.06
X.02 [(1S,2S)-1-methyl-2-(o4olyl)propyl] (2S)-2-[(4-methoxy3-propa noy loxy-py rid ine-2-ca rbony l)amino]propanoate 25:12 0.125+0.06
X.02 [(1 S,2S)-1-methyl-2-(o-tolyl)propyi] (2S)-2-[(4-methoxy3-propa noy loxy-py rid ine-2~carbonyl)amino]propanoate 25:24 0.0625+0.06
X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy- 3-propanoyioxy-pyridine-2-carbonyl)amino]propanoate 25:48 0.03125+0.06
X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4-methoxy3-propa noyfoxy- py rid i ne-2-carbon y l)amin o]pro panoate 100:3 1+0.03
X.02 [(1S,2S)-1-methyl-2-(o-tolyt)propyl] (2S)-2-[(4-methoxy3-propa noyfoxy-py rid ine-2-carbonyl)amino]propanoate 50:3 0.5+0.03
X.02 [(1S,2S)-1-methyt-2-(o-tolyi)propyl] (2S)-2-[(4-methoxy3-propanoyfoxy-pyridine-2-carbonyl)amino]propanoate 50:6 0.25+0.03
X.02 [(1S,2S)-1-methyl-2-(o-tolyi)propyl] (2S)-2-[(4-methoxy3-propa noy loxy-py rid ine-2-carbonyl)amino]propanoate 50:12 0.125+0.03
X.02 [(1S,2S)-1-methyl-2-(o-tolyi)propyl] (2S)-2-[(4-methoxy- 3-propanûyloxy-pyridine-2-carbonyl)amino]propanoate 50:24 0.0625+0.03
X.02 [(1 S,2S)-1 -metl^yl·2-(o-tolyi)pΓOpyl] (2S)-2-[(4-methoxy3-propanoy loxy-py ridine-2-carbonyl)a min ojpropanoate 50:48 0.03125+0.03
X.02 N-(2-f!uorophenyl)-4-[5-(trifluoromettiyl)-1I2,4oxadiazol-S-yObenzamide 1:20 1+20
X.02 N-(2-fluoroptienyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yi]benzamide 1:40 0.5+20
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1:80 0.25+20
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazo!-3-yl]benzamide 1:160 0.125+20
Component A Component B Ratio A:B Conc. (ppm) (A: B)
X.02 N-(2-fluoropheny 1)-4-(5-(trifluoromethy 1)-1,2,4oxadiazoi-3-yl]benzamide 1:10 1+10
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1l2,4oxadîazol-3-yl]benzamide 1:20 0.5+10
X.02 N-(2-fiuorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxad iazol-3-y l]benza mide 1:40 0.25+10
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2t4oxadiazol-3-yl]benzamide 1:80 0.125+10
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 C2-2 - Fungicidal activity > 80 % (% of untreated) against Septoria tritici
Component A Component B Ratio A:B Conc. (ppm) (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
Component A Component B Ratio A:B Conc. (ppm)
(A: B)
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 pyraclost robin 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
Component A Component B Ratio A:B Conc. (ppm) (A: B)
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 metyttetraprole 1 : 1 0.1 + 0.1
X.04 metyltetra proie 1 : 3 0.1 + 0.3
X.04 metyltetraproie 3 : 10 0.03 + 0.1
X.04 metyltetra proie 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-(tnfluoromethyi)-3-pyridyl]1-(1,2,4-triazoî-1-yÎ)propan-2-ol 1 : 1 0.1 +0.1
X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl)1-(1,2,4-triazol-1-yl)propan-2-ol 1 : 3 0.1 + 0.3
X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]- 1 -(1,2,4-triazol-1-yl)propan-2-ol 3 : 10 0.03 + 0.1
Component A Component B Ratio A:B Conc. (ppm) (A: B)
X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]- 1 -(1,2,4-triazol-1-yl)propan-2-ol 1 : 10 0.03 + 0.3
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-dichiorophenyi)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 1 0.1 + 0.1
X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 3 0.1 + 0.3
X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3’dimethyl-pent-3-enamide 3 : 10 0.03 + 0.1
X.04 (ZT2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3'dimethyl-pent-3-enamide 1 : 10 0.03 + 0.3
X.04 l(1S,2S)-1-methyl-2-(o4olyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate 10:3 0.2+0.06
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy- 3- propa noy loxy-py ridine-2carbonyl)amino]propanoate 5:3 0.1+0.06
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyll (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate 5:6 0.05+0.06
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate 5:12 0.025+0.06
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- meth oxy-3-propa n oyioxy-pyrid in e-2carbonyi)amino]propanoate 5:24 0.0125+0.06
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-((4- methoxy-3-propan oyioxy-pyrid ine-2carbonyl)amino]propanoate 5:48 0.00625+0.06
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyioxy-pyridine-2carbonyi)amino]propanoate 20:3 0.2+0.03
Comportent A Component B Ratio A: B Conc. (ppm)
(A: B)
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propylJ methoxy-3-propa noy loxy- pyridine-2carbonyl) amino] propanoate (23)-2-((4- 10:3 0.1+0.03
X.04 [(1 S,2S)-1-methyl-2-(o-tolyl) propyl] methoxy-3-propanoyloxy-pyridine-2carbonyl)amino] propanoate (23)-2-((4- 10:6 0.05+0.03
X.04 [(1 S,2S)-1 -methyl-2-(o-tolyl)propyl] methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate (25)-2-((4- 10:12 0.025+0.03
X.04 [(1S ,2S)-1 -methyl-2-(o-tolyl) propyl] methoxy-3-propanoytoxy-pyridine-2carbonyl)amirîo]propanoate (23)-2-((4- 10:24 0.0125+0.03
X.04 [(1 S, 2S)-1 -methyl-2-(o-tolyl) propyl] methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate (25)-2-((4- 10:48 0.00625+0.03
X.04 N-(2-fluorophenyl)-4-[5-(tnfluoromethyl)-1,2,4oxadiazo!-3-yl]benzamide 1:100 0.2+20
X.04 N-(2-fluorophenyl)-4-[5-(tnfiuoromethyl)-1,2,4oxadiazol-3-y IJbenzam ide 1:200 0.1+20
X.04 N-(2-fliJorophenyt)-4-[5-0rifiuoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1:400 0.05+20
X.04 N-(2-fluoropheny [)-4-(5- (trifluoromethy 1)-1,2,4oxadiazol-3-yl]benzamide 1:800 0.025+20
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1:50 0.2+10
X.04 N-(2-fluorophenyl)-4-[5-(trifluoro methyl)-1,2,4oxadiazol-3-yl]benzamide 1:100 0.1+10
X.04 N-(2-fluoropheny1)-4-[5-(trifluoromethyi)-1,2,4oxadiazol-3-yl]benzamide 1:200 0.05+10
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyf)-1,2,4oxadiazol-3-yl]benzamide 1:400 0.025+10
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
Component A Component B Ratio A:B Conc. (ppm) (A: B)
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
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 açtivity was evaluated on a 100-0 scale (100 = no disease growth; 0 = well completely covered by mycélium).
Table C2-3
Component A Component B Conc. (ppm) (A: B) Ratio A:B Açtivity (%) COLBY (expected açtivity %)
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
Component A Component B Conc. (ppm) (A: B) Ratio A: B Activity (%) COLBY (expected activity %)
isopyrazam 0.3 70
X.02 isopyrazam 0.1 + 0.1 1 : 1 90 85
X.02 îsopyrazam 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 C2-4
Component A Component B Conc. (ppm) (A: B) Ratio A:B Activity (%) COLBY (expected 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
Component A Component B Conc. (ppm) (A : B) Ratio A:B Activity (%> COLBY (expected activity %)
X.04 cyproconazole 0.1 +0.3 1 : 3 90 85
X.04 cyproconazole 0.03 + 0.3 1 ; 10 90 75
fol pet 0.3 20
X.04 fol pet 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 C2-5
Component A Component B Conc. (ppm) (A: B) Ratio A:B Activity (%) COLBY (expected activity %)
X.02 0.0625 90
X.02 0.03125 20
[(1S,2S)-1-methyi-2-(o- tolyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.06 70
[(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.03 50
X.02 [(1ST2S)’1-methyL2-(o- tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy- 0.0625+0.06 25:24 100 97
pyridine-2carbonyl)amino]propanoate
X.02 [(1S,2S)-1-methyl-2-(otoly1)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.03125+0.06 50:24 100 76
X.02 [(1S,2S)-1-methyl-2-(otolyl)propylj (2S)-2-[(4mettioxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.0625+0.03 50:24 100 95
X.02 [(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoale 0.03125+0.03 25:24 100 60
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- tolyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.025+0.06 5:12 100 91
X.04 [(1S,2S)-1-methyl-2-(o- tolyl)propyl] (23)-2-((4methoxy-3-propanoyîoxypyridine-2carbonyl)amino]propanoate 0.0125+0.06 5:24 100 76
X.04 [(1S,2S)-1-methyi-2-(otolyl)propyl] (2S)-2-[(4methoxy-3-propa n oy loxypyridine-2carbonyi)amino]propanoate 0.00625+0.06 5:48 90 70
X.04 [(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-f(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.025+0.03 10:12 100 85
X.04 [(1S,2S)-1-methyl-2-(otolyljpropyl) (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.0125+0.03 10:24 90 60
X.04 [(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.00625+0.03 10:48 70 50
N-(2-fluorophenyl)-4-[5(trifluoro methyl)-1,2,4oxadiazol-3-ylJbenzamide 20 0
N-(2-fluorophenyl)-4-[5(trifluoro methyl)-1,2,4oxadiazol-3-yl]benzamide 10 0
X.04 N-(2-fluorophenyl)-4-[5(trifluoromethyl)-l ,2,4oxadiazol-3-yi]benzamide 0.025+20 1:800 90 70
X.04 N-(2-fluorophenyl)-4-[5(trifluoromethyl)-! ,2,4oxadiazol-3-yl]benzamide 0.025+10 1:400 90 70
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 açtivity against Septoria glycines (brown spot):
Conidia ofthe fungus harvested from a fresh culture grown on artificial media, were directly mixed into 5 nutrient broth (PDB potato dextrose broth). A DMSO solution ofthe 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 tirs.
The following compound mixtures gave at least 80% control Septoria glycines at rates cited in the table 10 when compared to untreated control under the same conditions, which showed extensive disease development:
Table C3-1 - Fungicidal activity > 80 % (% of untreated) against Septoria glycines
Component A Component B Ratio A:B Conc. (ppm) (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
Component A Component B Ratio A; B Conc. (ppm) (A: B)
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
Component A Component B Ratio A: B Conc. (ppm) (A: B)
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 -(1,2,4-triazol-1 -yl)propan-2-ol 1 :1 0.1 + 0.1
Component A Component B Ratio A:B Conc. (ppm) (A: B)
X.02 2-[6-(4'bromophenoxy)-2-(trifIuoromettiyl)-3-pyridyl]1-(1,2,4-triazol-1-yi)propan-2-ol 1 ; 3 0.1 + 0.3
X.02 2-[6-(4“bromophenoxy)-2-(trifluoromethyt)-3-pyridyl]1 -(1,2,4-triazol-1 -yi)propan-2-ol 3 : 10 0.03 + 0.1
X.02 2-[6’(4-bromophenoxy)-2-(trifluoromethyi)-3-pyridyl]- 1-(1,2,4-triazoM-yi)propan-2-ol 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 (Ζ,2Ε)-5-[1-(2,4-ΡίοΡΙθΓθρΜβηνΙ)ργΓ3ζοΙ-3-νΙ]οχγ-2methoxyimino-N,3-dimethyi-pent-3-enamide 1 : 1 0.1 + 0.1
X.02 (Z,2E)-541(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 1 ; 3 0.1 + 0.3
X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2methoxy i mino-N, 3-d imethyi-pent-3-e namide 3 : 10 0.03 + 0.1
X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy'2methoxyimino«N,3-dimethyl-pent-3-enamide 1 : 10 0.03 + 0.3
X.02 [(1 S,2S> 1 -methyl-2-(o4olyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl)a min a] propanoate 50 : 3 1+0,06
X.02 [(1 S,2S)-1 -methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate 25 : 3 0.5+0.06
X.02 [(1 S,2S)-1 -methyl-2-(o-tolyi)propyi] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2” carbonyl)amino]propanoate 25 : 6 0.25+0.06
X.02 [(1 S,2S)-1 -methyl-2-(o-toly!)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2ca rbony l)amino]propa noate 25 : 12 0.125+0.06
X.02 [(1 S^SJ-l-methyl-Z-io-tolyiJpropyi] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2- ca rbony 1) aminojpropa noate 25 : 24 0.0625+0.06
X.02 [(1Sl2S)-1’methyl·2-(o-tolyl)propylJ (2S)-2-[(4- m et h oxy-3- propa η o y I o xy- py rid i n e-2ca rbony l)amino]propa noate 25 : 48 0.03125+0.06
Component A Component B Ratio A:B Conc. (ppm) (A: B)
X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propylJ (2S)-2-[(4- meth oxy-3-propanoy loxy-pyrid ine-2carbonyl)amino]propanoate 100 : 3 1+0.03
X.02 [(1S.2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbony!)amino]propanoate 50 : 3 0.5+0.03
X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyndine-2carbonyi)amino]propanoate 50 : 6 0.25+0.03
X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbony l)a min o] propanoate 50 : 12 0.125+0.03
X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoytoxy-pyridine-2carbonyl)amino] propanoate 50 ; 24 0.0625+0.03
X.02 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2- carbonyl)amino] propanoate 50 : 48 0.03125+0.03
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyi)-1,2,4oxadiazol-3-yl]benzamide 1 : 20 1+20
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 40 0.5+20
X.02 N-(2-fluorophen y t)-4-[5-(trifluoro methyl)-1,2,4oxadiazo!-3-yl]benzamide 1 : 80 0.25+20
X.02 N-(2-fliiorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 160 0,125+20
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 320 0.0625+20
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 10 1+10
X.02 N-(2-fluoro phenyl)-4-[5-(trifluoromethy 1)-1,2,4oxadiazol-3-yl]benzamide 1 : 20 0.5+10
X.02 N-(2-fl uorophenyl)-4-[5-(tnfiuoromethy 1)-1,2,4oxadiazol~3-yl]benzamide 1 : 40 0.25+10
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1t2,4oxadiazol-3-yl]benzamide 1 ; 80 0.125+10
Component A Component B Ratio A:B Conc. (ppm) (A: B)
X.02 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 160 0.0625+10
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 C3-2 - Fungicidal activity > 80 % (% of untreated) against Septoria glycines
Component A Component B Ratio A:B Conc, (ppm) (A: B)
X.04 glyphosate 1 : 1 0.1 +0,1
X.04 glyphosate 1 : 3 0.1 +0.3
X.04 chiorothalonil 1 : 1 0.1 +0.1
X.04 chlorothalonil 1 : 3 0.1 +0.3
X.04 chiorothalonil 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
Comportent A Component B Ratio A: B Conc. (PPm) (A: B)
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 fenpropidîn 1 : 1 0.1 +0.1
X.04 fenpropidîn 1 : 3 0.1 +0.3
X.04 fenpropidîn 3 : 10 0.03 + 0.1
X.04 fenpropidîn 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 trînexapac-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
Component A Component B Ratio A:B Conc. (ppm) (A: B)
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 foipet 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 tebuconazote 1 : 1 0.1 +0.1
X.04 tebuconazote 1 : 3 0.1 +0.3
X.04 tebuconazote 3 : 10 0.03 + 0.1
X.04 tebuconazole 1 : 10 0.03 + 0.3
X.04 prothioconazoie 1 : 1 0.1 + 0.1
X.04 prothioconazole 1 : 3 0.1 + 0.3
X.04 prothioconazoie 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 copperoxychloride 1 : 3 0.1 + 0.3
X.04 benzovindiflupyr 1 : 1 0.1 + 0.1
Component A Component B Ratio A: B Conc. (ppm) (A: B)
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 mefentriflu con azote 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
Component A Component B Ratio A:B Conc. (ppm) (A: B)
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-(trifltJoromethyl)-3-pyridyl]-1(1,2,4-triazol-1-yl)propan-2-ol 1 : 1 0.1 +0.1
X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1(1,2,4-triazol-1-yl)propan-2-ol 1 : 3 0.1 + 0.3
X.04 2-[6-(4-bromophenoxy)-2-(tnfluoromethyl)-3-pyridy1]-1(1,2,4-triazol-1 -yl)propan-2-ol 3 : 10 0.03 + 0.1
X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1(1,2,4-triazol-1-yl)propan-2-ol 1 : 10 0.03 + 0.3
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-2methoxyimino-N,3-dimethyf-pent-3-enamide 1 : 1 0.1 +0.1
X.04 (Z ,2 E)-5-[1 -(2,4-d ich lorophenyl)pyrazoi-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 3 0.1 + 0.3
X.04 (Z,2E)-5-[1-(2,4-dichlorophenyi)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethy!-penl·3-eπamide 3 : 10 0.03 + 0.1
X.04 (Z.2E)-5-[1-(2,4-dich!orophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimelhyl-pent-3-enamide 1 : 10 0.03 + 0.3
X.04 [(1S,2S)-1-methy!-2-(0-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoy!oxy-pyridine-2- carbonyl)amino] propanoate 10 : 3 0.2+0.06
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyll (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl) amino] propanoate 5 : 3 0.1+0.06
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyioxy-pyridine-2- carbonyl) amino] propanoate 5 : 6 0.05+0.06
Component A Component B Ratio A:B Conc. (ppm) (A: B)
X.04 [(1 S,2S)-1 -methyl-2-(o-tolyl)propyll (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl)a min o] propanoate 5 : 12 0.025+0.06
X.04 [(1 S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyi)amino]propanoate 5 : 24 0.0125+0.06
X.04 [(1S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy’pyridine-2carbonyl)amino]propanoate 20 : 3 0.2+0.03
X.04 ((1 S,2S)-1-methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl)amino] propanoate 10 ; 3 0.1+0.03
X.04 [(1 S,2S)-1 -methyl-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyioxy-pyridine-2carbonyl)a min o] propanoate 10 : 6 0.05+0.03
X.04 [(1S,2S)-1-methy!-2-(o-tolyl)propyl] (2S)-2-[(4- methoxy-3-propanoyloxy-pyridine-2carbonyl)amino]propanoate 10 : 12 0.025+0.03
X.04 N-(2-fl uorophenyl)-4-[5-(triflu oromethy 1)-1,2,4oxadiazol-3-yl]benzamide 1 : 100 0.2+20
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyi)-1,2,4oxadiazol-3-yl]benzamide 1 : 200 0.1+20
X.04 N-(2-fiuorophenyl)-4-[5-(tnfiuoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 :400 0.05+20
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxad iazol-3-y Ijbenzam ide 1 : 800 0.025+20
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 50 0.2+10
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 100 0.1+10
X.04 N-(2-fiuorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]benzamide 1 : 200 0.05+10
X.04 N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4oxad iazo l-3-y IJbenzam ide 1 ; 400 0.025+10
X.04 Florylpicoxamid 10:1 0.2+0.02
Component A Component B Ratio A:B Conc. (ppm) (A: B)
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
The following mixture compositions atthe 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 mycélium).
Table C3-3
Component A Component B Conc. (ppm) (A : B) Ratio A:B Activity (%) COLBY (expected 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
Component A Component B Conc. (ppm) (A: B) Ratio A: B Activity (%) COLBY (expected activity %)
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 Û.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-ethyî 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
101
Component A Component B Conc. (ppm) (A: B) Ratio A:B Activîty (%) COLBY (expected activîty %)
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 C3-4
102
Component A Component B Conc. (ppm) (A: B) Ratio A:B Activity (%) COLBY (expected 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 i 10 90 76
cyproconazoîe 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
103
Component A Component B Conc. (ppm) (A: B) Ratio A: B Activîty (%) COLBY (expected activîty %)
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 C3-5
Component A Component B Conc. (ppm) (A: B) Ratio A:B Activîty W COLBY (expected activîty %)
X.02 0.03125 70
[(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.06 0
[(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoafe 0.03 0
X.02 [(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-((4methoxy-3-propanoyloxypyridine-2carbonyl)amino] propanoate 0.03125+0.06 50 : 24 90 70
X.02 [(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxy- 0.03125+0.03 25 : 24 90 70
104
pyridine-2carbonyl)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- toiyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.025+0.06 5 : 12 100 90
X.04 [(1 S,2S)-1-methy 1-2-(0- tolyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.0125+0.06 5 : 24 90 50
X.04 {(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-[(4methoxy-3-propa noy loxypyridine-2carbonyl)amino]propanoate 0.00625+0.06 5:48 70 0
X.04 [(1S,2S)-1-methyl-2-(otoly!)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.0125+0.03 10 : 24 70 50
X.04 [(1ST2S)-1-methyl-2-(o- tolyî)propyl] (2S)-2-[(4- methoxy-3- propa noyioxypyridine-2carbonyl)amino]propanoate 0.00625+0.03 10 : 48 50 0
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 Glomerelia lagenarium syn. Colietotrichum lagenarium (anthracnose):
105
Conid ia of the fungus from cryogénie storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtîter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were 5 incubated at 24 ’C and the inhibition of growth was determined photometrically after 72 tirs at 620nm.
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 C4-1 - Funoicidal activity >80 % (% of untreated) against Glomerella lagenarium
Component A Component B Ratio A:B Conc. (ppm) (A: B)
X.02 chlorothatonil 1 : 1 0.1 + 0.1
X.02 chlorothatonil 1 : 3 0.1 + 0.3
X.02 chlorothatonil 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 pyraciostrobin 1 : 1 0.1 + 0.1
X.02 pyracîostrobin 1 : 3 0.1 + 0.3
X.02 pyraciostrobin 3 : 10 0.03 + 0.1
X.02 pyraciostrobin 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
106
Component A Component S Ratio A:B Conc. (ppm) (A: B)
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 quinofumeiin 1 : 1 0.1 +0.1
X.02 quinofumeiin 1 : 3 0.1 + 0.3
X.02 quinofumeiin 3 : 10 0.03 + 0.1
X.02 quinofumeiin 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 metyltetra proie 1 : 1 0.1 +0.1
X.02 metyltetra proie 1 : 3 0.1 +0.3
X.02 metyltetra p rôle 3 : 10 0.03 + 0.1
X.02 metyltetra p rôle 1:10 0.03 + 0.3
X.02 amlnopyrifen 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,2 E)-5-[1 -(2,4-d ichtorophe n y I) pyrazo l-3-y l]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 1 0.1 + 0.1
X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2' methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 3 0.1 + 0.3
107
Component A Component B Ratio A: B Conc. (ppm) (A : B)
X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2methoxyimino-N,3-dimethy1-pent-3-enamide 3 : 10 0.03 + 0.1
X.02 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2mefhoxyimino-N,3-dimethyl-pent-3-enamide 1: 10 0.03 + 0.3
Table C4-2 - Fungicidal activity > 80 % (% of untreated) against Glomerella lagenarium
Component A Component B Ratio A: B Conc. (ppm) (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 maneozeb 1 : 1 0.1 +0.1
X.04 maneozeb 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 propiconazoie 1 : 1 0.1 + 0.1
X.04 propiconazoie 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 fenpropîmorph 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 hexaconazoie 1 : 1 0.1 + 0.1
X.04 hexaconazoie 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
108
Component A Component B Ratio A:B Conc. (ppm) (A: B)
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
109
Component A Component B Ratio A:B Conc. (ppm) (A: B)
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 oxyctilorîde 1 : 1 0.1 + 0.1
X.04 copper oxyctilorîde 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 isofïucypram 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
Component A Component B Ratio A:B Conc. (Ppm) (A: B)
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(1,2,4-triazol-1-yl)propan-2-ol 1 : 1 0.1 + 0.1
X.04 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1(1,2,4-triazol-1-yl)propan-2-ol 1 : 3 0.1 + 0.3
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-2methoxyimino-N,3-dimethyl·pent-3-enamide 1 : 1 0.1 + 0.1
X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazoi-3-y!]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 3 0.1 + 0.3
X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazoi-3-yl]oxy-2methoxyimino-N,3-dimethyl-pent-3-enamide 3 : 10 0.03 + 0.1
X.04 (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3“yt]oxy-2‘ methoxyimino-N,3-dimethyl-pent-3-enamide 1 : 10 0.03 + 0.3
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 (Glomerella lagenarium syn. Colietotrichum iagenanum). Fungicidal activity was evaluated on a 100-0 scale (100 = no disease growth; 0 = well completely 5 covered by mycélium).
Table C4-3
Component A Component B Conc. (ppm) (A: B) Ratio A:B Activity W COLBY (expected 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
111
Component A Component B Conc. (ppm) (A : B) Ratio A:B Activity (%) COLBY (expected activity %)
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
prothiocon azole 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
ipfiufenoquin 0.1 50
X.02 ipfiufenoquin 0.1 + 0.1 1 : 1 90 60
X.02 ipfiufenoquin 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- bromophenoxy)-2- (tnfluoromethyf)-3- 0.3 0
112
Component A Component B Conc. (ppm) (A : B) Ratio A:B Activity (%) COLBY (expected activity %)
pyridyl]-1 -(1,2,4-triazol1-yl)propan-2-ol
X.02 2-16-(4- bromophenoxy)-2(trifluoromethyl)-3pyridyl]-1-(1,2,4-triazol1-yl)propan-2-ol 0.03 + 0.3 1 : 10 20 0
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 C4-4
Component A Component B Conc. (PPm) (A: B) Ratio A:B Activity (%) COLBY (expected 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
fofpet 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
113
Component A Component B Conc. (ppm) (A: B) Ratio A: B Activity (%) COLBY (expected activity %)
benzovindiflupyr 0.1 50
X.04 benzovindiflupyr 0.03 + 0.1 3 : 10 90 50
mefentrifluconazole 0.3 0
X.04 mefe ntriflucon azole 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- bromophenoxy)-2(trifluoromethyl)-3pyridyl]-1-(1,2,4-triazol1-yl)propan-2-ol 0.3 0
X.04 2-(6-(4- bromophenoxy)-2- (trifluoromethyl)-3pyridyl]-1-(1,2,4-triazol- 1-yl)propan-2-ol 0.03 + 0.3 1 : 10 20 0
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 (taraet leaf spot):
Conidia ofthe fungus from cryogéniestorage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-weil 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 620nm.
114
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 cassiicota). Fungicidal activîty was evaluated on a 100-0 scale (100 = no disease growth; 0 = well completely covered by mycélium).
Table C5-1
Component A Component B Conc. (ppm) (A: B) Ratio A:B Activîty (%) COLBY (expected activîty %)
X.02 1 20
X.02 [(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 1+0.06 50 : 3 50 20
X.02 [(1S,2S)-1-methyl-2-(otolyl)propyI) (2S)-2-[(4methoxy-3-propanoyioxypyridine-2carbonyl)amino]propanoate 1+0.03 100 : 3 50 20
N-(2-fluorophenyl)-4-[5(trifluoromethyl)-l ,2,4oxadiazol-3-yl]benzamide 20 0
N-(2-fluorophenyl)-4-[5(triflu oromethy l)-1,2,4oxadiazol-3-yl]benzamide 10 0
X.02 N-(2-fiuorophenyl)-4-[5(triflu oromethy l)-1,2,4oxadiazol-3-yl]benzamide 1+20 1:20 50 20
X.02 N-(2-fluorophenyl)-4-[5(trifluoromethyl)-l ,2,4oxadiazol-3-yl]benzamide 1 + 10 1:10 50 20
X.04 0.2 20
[(1 S,2S)-1-methy 1-2-(0- tolyt)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2ca rbo ny l)amino]propanoate 0.06 0
[(1S,2S)-1-methyl-2-(otolyljpropyl] (28)-2-((4methoxy-3-propanoyloxypyridine-2carbonyljamino] propan oate 0.03 0
115
X.04 [(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.2+0.06 10 : 3 50 20
X.04 [(1S,2S)-1-methyl-2-(otolyljpropyl] (2S)-2-[(4methoxy-3-propanoyloxypyridine-2carbonyl)amino]propanoate 0.2+0.03 20 : 3 20 20
N-(2-fluoropheny 1)-4-(5(trifluoromethyl)-l ,2,4oxadiazol-3-yl]benzamide 20 0
N-(2-fluoropheny 1)-4-(5(trifluoromethyl)-l ,2,4oxadîazol-3-yl]benzamide 10 0
X.04 N-(2-fiuorophe ny 1)-4-(5(trifluoromethyO-IZ^oxadiazol-3-yl]benzamide 0.2+20 1:100 50 20
X.04 N-(2-fluorophenyl)-4-[5(trifluoromethyl)-l ,2,4oxadiazol-3-yl]benzamide 0.2+10 1:50 50 20
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 5
Whole soybean plants are treated with the recited active ingrédients 4 weeks after planting. 1 day after spraying leaf disks are eut from the first trifoliate leaf, Five répétitions 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 10 the relation ofthe treated vs untreated, infested check. (100 = no disease, no damage to the leaf, 0 = high infestation, leaf damaged heavily). The rates ofthe active ingrédients used are given in the tables as g active ingrédient (a.i.)/ha.
The results are shown in the tables below:
Table D1 - Activity (% of untreated) against Phakopsora pachyrhizi
116
Compound X.02 (g/ha) Fenpropimorph (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 D2 - Activity (% of untreated) against Phakopsora oachvrhizi
Compound X.02 (g/ha) Fenpropidin (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 1200 93 70
1.13 225 1 1200 89 64
1.13 450 1 :400 88 61
Table D3 - Activity (% of untreated) against Phakopsora pachyrhizî 5
Compound X.02 (g/ha) T rifloxystrobin (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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
117
Compound X.02 (g/ha) Trifloxystrobin (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
4.50 9 1 :2 88 23
2.25 4.5 1 :2 62 14
2.25 9 1 :4 74 15
Table D4 - Activity (% of untreated) against Phakopsora pachvrhizi
Compound X.02 (g/ha) Azoxystrobin (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 D5 - Activity (% of untreated) against Phakopsora pachvrhizi
Compound X.02 (g/ha) Metyltetra proie (g/ha) Compound ; Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 D6 - Activity (% of untreated) against Phakopsora pachvrhizi
118
Compound X.02 (g/ha) Pyraclostrobin (g/ha) Compound : Mixing partner Observed Activîty (%) COLBY Expected Activîty (%)
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 D7 - Actîvitv (% of untreated) against Phakopsora pachvrhizi
Compound X.02 (g/ha) (Z,2E)-5-[1-(2,4dichlorophenyl)pyrazol-3yl]oxy-2'methoxyimino-N,3dimethyl-pent-3-enamide (g/ha) Compound : Mixing partner Observed Activîty (%) COLBY Expected Activîty (%)
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 D8 - Activîty (% of untreated) against Phakoosora pachvchizi
Compound X.02 (g/ha) Benzovindiflupyr (g/ha) Compound : Mixing partner Observed Activîty (%) COLBY Expected Activîty (%)
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
119
Table D9 - Açtivity (% of untreated) against Phakopsora pachyrhizi
Compound X.02 (g/ha) Pydiflumetofen (g/ha) Compound : Mixing partner Observed Açtivity (%) COLBY Expected Açtivity (%)
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 D10 - Açtivity (% of untreated) against Phakopsora pachyrhizi
Compound X.02 (g/ha) Prothioconazole (g/ha) Compound : Mixing partner Observed Açtivity (%) COLBY Expected Açtivity (%)
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 D11 - Açtivity (% of untreated) against Phakopsora pachyrhizi
Compound X.02 (g/ha) Difenoconazole (g/ha) Compound : Mixing partner Observed Açtivity (%) COLBY Expected Açtivity (%)
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 D12 - Açtivity (% of untreated) against Phakopsora pachyrhizi
120
Compound X.02 (g/ha) Cyproconazole (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 D13 - Activity (% of untreated) against Phakopsora pachyrhizî
Compound X.04 (g/ha) Fenpropimorph (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 D14 - Activity (% of untreated) against Phakopsora pachyrhizî
Compound X.04 (g/ha) Fenpropidin (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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
121
Compound X.04 (g/ha) Fenpropîdin (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
1.13 450 1 : 400 90 68
Table D15 - Activity (% of untreated) against Phakopsora oachyrhizi
Compound X.04 (g/ha) Mancozeb (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 D16 - Activity (% of untreated) against Phakopsora pachyrhizi
Compound X.04 (g/ha) Chlorothalonil (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 D17 - Activity (% of untreated) against Phakopsora pachyrhizi
Compound X.04 (g/ha) Folpet (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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
122
Table D18 - Activity (% of untreated) against Phakopsora pachvrhizi
Compound X.04 (g/ha) Trifloxystrobin (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 DI9 - Activity (% of untreated) against Phakopsora pachvrhizi
Compound X.04 (g/ha) Azoxystrobin (g/ha) Compound : Mixing partner Observed Activity (%) Expected Activity (%)
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 D20 - Activity (% of untreated) against Phakopsora pachvrhizi
123
Compound X.04 (g/ha) Metyltetra proie (g/ha) Compound : Mixing partner Observed Açtivity (%) COLBY Expected Açtivity (%)
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 D21 - Açtivity (% of untreated) against Phakopsora pachyrhizi
Compound X.04 (g/ha) Pyraclostrobin (g/ha) Compound : Mixing partner Observed Açtivity (%) COLBY Expected Açtivity (%)
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 D22 - Açtivity (% of untreated) against Phakopsora pachyrhizi
124
Compound X.04 (g/ha) (Z,2E)-5-[1-(2,4dichlorophenyl)pyrazol3-yl]oxy-2methoxyimino-N,3dimethyl-pent-3enamide (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 D23 - Activity (% of untreated) against Phakopsora pachyrhizî
Compound X.04 (g/ha) Benzovindiflupyr (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 D24 - Activity (% of untreated) against Phakopsora nachvrhizi
Compound X.04 (g/ha) Pydiflumetofen (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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
125
Table D25 - Activity (% of untreated) against Phakopsora pachyrhizi
Compound X.04 (g/ha) Prothioconazole (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 D26 - Activity (% of untreated) against Phakopsora pachyrhizi
Compound X.04 (g/ha) Difenoconazole (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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 D27 - Activity (% of untreated) against Phakopsora pachyrhizi
Compound X.04 (g/ha) Cyproconazole (g/ha) Compound : Mixing partner Observed Activity (%) COLBY Expected Activity (%)
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

Claims (15)

1. A fungicidal composition comprising a mixture of components (A) and (B) as active ingrédients, wherein component (A) is a compound of formula (I):
wherein
R1 is methyl;
R2 is hydrogen;
R3 is hydrogen;
R4 is Cs-Cycycioatkyl;
or an agronomically acceptable sait thereof;
and component (B) is a compound selected from the group consisting of:
bixafen, sutfur, copper hydroxide, triclopyricarb, acibenzolar-S-methyl, copper oxychloride, cyproconazole, difenoconazole, epoxîcon-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-etyt-aluminium, pyribencarb, tricyclazole, mandipropamid, flubeneteram, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isofiucypram, isotianil, dipymetitrone, flumdapyr, coumethoxystrobin, Ivbenmixianan, mandestrobin, oxathiapiprohn, pyraziflumid, inpyrfluxam, mefentrifluconazole, ipfentrifluconazole, aminopyrifen, (Z,2E)-5-[1-(420876
127 ch lorophen yl)pyrazo l-3-y l]oxy-2- methoxy imino-N, 3-dimethy I- pent-3-ena mide, fenpicoxamid, ipflufenoquin, quinofumelin, benzothiostrobin, fluopyram, (difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, florylpicoxamid, pyrapropoyne, 24-((6-(2-(2,4difluorophenyl)-1,1-difluoro-2-hydiOxy-3-(1,2l4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, metyltetra proie, fluoxapiprolin, enoxastrobin, 4-[[6-[2-(2,4-dif]uorophenyl)-1,1-difluoro-2-hydroxy3-(5-thioxo-4H-112,4-triazol-1-yl)propyl]-3-pyridy!]oxy]benzonitrile, trinexapac, trinexapac-ethyl, coumoxystrobin, N'-[5-bromo-2-methy1-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-Nmethyl-fonmamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N~ ethyl-N-methyl-formamidine, ethyl-N-methyl-formamidine, ethyl-N-methyl-formamidine,
N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-NN'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-NN'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-Nisopropyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethylN-methyi-formamidine,
N-isopropyl-N’-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1pheny!-ethyl)phenyi]-N-methyl-formamidine, N’-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)5-methoxy-2-methyl-pheny1]-N-isopropyî-N-methyl-formamidine, N-ethyl-N’-[5-methoxy-2methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl·formamidine1 N-ethyl-N'-[5-methoxy-2methyl-4-[2-trifuoromethyl)tetrahydrofuran-2-yl]pheny[]-N-methyl-formamidine, N-(2fluorophen y 1)-4-(5- (trifluoro methyl)-1,2,4-oxadiazol-3-yl]benzamide, N-methoxy-N-[[4-(5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyi]cyclopropanecarboxamide, N,2-dimethoxyN-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N([4-[5-(trifiuoromethyl)-1,2,4-oxadiazoi-3-yi]phenyl]methyl]propanamide, [(1S,2S)-1-methyl-2-(otolyl)propyl] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate, 1meth oxy-3-methy I-1 - [[4- [5-(trifluo romethy l)-1,2,4-oxadiazol-3-y I] ph eny I] meth yl] urea, 1,3dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl] phenyl] meth y!]urea, N-([4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl] phenyl] meth yl]propanamide, 4,4-dimethyl·2-((4-[5-(trifluoro methyl)-1,2,4oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyî-2-((4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]phenyi]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(tnfluoromethyi)-1,2,4-oxadiazol3-yi]phenyl]methyl]pyrazole-4-carboxy!ate, N,N-dimethyl-1-((4-[5-(trifluoromethyi)-1,2,4oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3pyrid y 1)-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluo romethyl)-3-pyridyl]-1 (1,2,4-triazoi-1-yl)propan-2-ol, 3-(2-(1-chlorocyclopropyl)-3-(2-fluorophen y t)-2-hydroxypropyl]imidazole-4-carbonitrile, 3-[2-(1-chlorocyclopropyî)-3-(3-chloro-2-fluoro-phenyl)-2hydroxy-propyl]imidazo!e-4-carbonitrile, (4-phenoxyphenyl)methyt 2-amino-6-methyi-pyridine-3carboxylate, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; Nmethyl·4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamrde, (5-methyf-2pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methytisoxazol-5-yl)-[4(5-(trifluoromethyl)-1,2,4-oxadiazof-3-yl]phenyl)methanone, ethyl 1-H5-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]-2-thienyl]methyt]pyrazole-4-carboxylate, 2,2-difluoro-N-methy 1-2-(4-(5
128 (trifluoromethyl)-1,2t4-oxadiazol-3-yllphenyl]acetamide, N-[(Z)-methoxyiminomethyl]-445(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5(trifluoromethylj-l^^-oxadiazol-S-yllbenzamide, N-[3-(4-chlorophenyl)-4,5-dthydroisoxazol-5yl]-5-methyl-1,2,4-oxadiazoie-3-carboxamide, 2-(difluoromethyl)-N-(1[1-dimethyl-3-propyl-indan4-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-methylphenyl)-1,3-dimethyl-butyl] (2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2carbonyl]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-chioro-N-cydopropyl-5-(1-{2,6-dichloro-4-[1l2,2,2’tetrafluoro-1(trifluoromethyl)ethyi]phenyl}'1 H-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-cydopentyl-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-cyclohexy!-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (compound X.04);
or an agronomically acceptable sait thereof.
3. A fungicidal composition according to claim 1 or claim 2, 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-cydohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (compound X.04);
or an agronomically acceptable sait thereof.
4. A fungicidal composition according to any one of daims 1 to 3, wherein component (B) is a compound selected from the group consisting of bixafen, triclopyricarb, cyproconazole,
129 difenoconazole, epoxîcon-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, coumethoxystrabin, mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, metyltetra proie, enoxastrobin, coumoxystrobin, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyll-1-(1I2,4-triazol-1yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan2-ol, 3-(2-(1-chlorocyclopropyl)-3-(2-fluorophenyt)-2-hydroxy-propyl]imidazole-4-carbonitrile and 3-(2-(1-ch lorocyclopropyl)-3-(3-chloro-2-fiuoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile.
5. A fungicidal composition according to any one of claims 1 to 4, 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 metyltetraproie.
6. A fungicidal composition according to any one of claims 1 to 5, wherein component (B) is azoxystrobin or trifloxystrobin.
7. A fungicidal composition according to to any one of claims 1 to 6, wherein the weight ratio of component (A) to component (B) is from 100:1 to 1:100.
8. A fungicidal composition according to to any one of claims 1 to 7, wherein the weight ratio of component (A) to component (B) is from 20:1 to 1:40.
9. A fungicidal composition according to to any one of claims 1 to 8, wherein the weight ratio of component (A) to component (B) is from 12:1 to 1:25.
10. A fungicidal composition according to to any one of claims 1 to 9, wherein the weight ratio of component (A) to component (B) is from 5:1 and 1:15.
11. A fungicidal composition according to to any one of claims 1 to 10, wherein the weight ratio of component (A) to component (B) is from 2:1 to 1:5.
12. A fungicidal composition according to any of claims 1 to 11, wherein the composition comprises one or more further pesticides selected from the group consisting of:
a fungicide, selected from etridiazole, fluazinam, benzovindiflupyr, pydiflumetofen, benalaxyi, benalaxyl-M (kiralaxyl), furalaxyl, metalaxyl, metalaxyl-M (mefenoxam), dodicin, N'-(2,5Dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-Dichloro-thiazol-2-yloxy)
130
2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, N’-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4thiadiazol-5-yl]oxy]-2,5-dimethyi-phenyl]-N-ethyl-N-methyl-formamidine, ethirimol, 3’-chloro-2methoxy-N-[(3RS)-tetrahydro-2-oxofuran-3-yl]acet-2',6'-xylidide (dozylacon), cyprodinil, mepanipyrim, pyrimethanil, dithianon, aureofungin, blasticidin-S, biphenyl, chloroneb, dicloran, hexachlorobenzene, quintozene, tecnazene, (TC NB), tolcîofos-methyl, metrafenone, 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, fluopicoiide (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-4carboxamide diclocymet, N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide N-cyclopropyl-3-(difluoromethyl)-5fluoro-N-[(2-isopropylphenyl)methyl]-Tmethylpyrazole-4-carboxamide carpropamid, chlorothalonil, flumorph, oxine-copper, cymoxanil, phenamacril, cyazofamid, flutianii, thicyofen, chlozolinate, iprodione, procymidone, vinclozolin, bupirimate, dinocton, dinopenton, dinobuton, dinocap, meptyldinocap, diphenylamine, phosdiphen, 2,6-dimethyl-[1,4]dithiino[2,3c: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), zi ne b, ziram, dithioether, isoprothiolane, ethaboxam, fosetyl, fosetyl-aîu minium (fosetyl-al), methyl bromide, methyl iodide, methyl isothîocyanate, cyciafuramid, 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, fenamîdone, Bordeaux mixture, calcium polysulfide, copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulphate, copper tailate, cuprous oxide, sulphur, carbaryl, phthalide (fthalide), dingjunezuo (Jun Si Qi), oxathiapiprolin, fluoroimide, mandipropamid, KSF-1002, benzamorf, dimethomorph, fenpropimorph, tridemorph, dodemorph, dfethofencarb, fentin acetate, fentin hydroxide, carboxin, oxycarboxin, drazoxolon, famoxadone, m-phenylphenol, p-phenylphenol, tribromopheno! (TBP), 2-[2-[(7,8difluoro-2-methyl-3-quinolyl)oxy]-6-fIuoro-phenyl]propan-2-ol 2-[2-fluoro-6-[(8-fluoro-2-methyl-3quinolyl)oxy]phenyl]propan-2-ol, cyflufenamid, ofurace, oxadixyl, flutolanil, mepronil, isofetamid, fenpiclonil, fludroxonil, 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 hydrazîde, mepiquat, naphthalene acetamide, paclobutrazol, prohexadione, prohexadione-calcium, thidiazuron, tribufos (tributyl phosphorotrithioate), trinexapac,
131 uniconazole, α-naphthalene acetic acid, polyoxin D (polyoxrim), BLAD, chitosan, fenoxaml, fofpet, 3-(dîfluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6trichlorophenyl)ethyl]pyrazole-4-carboxamide, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, fenpyrazamine, diclomezine, pyrifenox, boscalid, fluopyram, diflumetorim, fenarimoi, 5-fluoro-2-(p-tolylmethoxy)pynmidin-4-amine ferimzone, dimetachlone (dimethaclone), pyroquilon, proquinazid, ethoxyquin, quînoxyfen, 4,4,5-trifluoro3,3-dimethy!-1-(3-quinolyl)isoquinoline 4,4-difluoro-3,3-dimethyM-(3-quinolyl)isoquinoline 5fluoro-3,3,4,4-tetramethyl-1-(3-quinolyl)isoquinoline 9-fluoro-2,2“dimethy!-5-(3-quinolyl)-3H-1,4benzoxazepine, tebufloquin, oxolinic acid, chinomethionate (oxythîoquinox, quinoxymethionate), spiroxamine, (E)-N-methyk2- [2- (2, 5-dimethylphenoxymethyl) phenyi]-2-methoxyiminoacetamîde, (mandestrobin), azoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, pyriotrobin, fenamistrobin, fiufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metaminostrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, triclopyricarb, trifloxystrobin, amisulbrom, dichlofluanid, tolylfluanid, but-3-ynyl ^^[6-[((Z)-[(1-rneti^yltetrazol·5-yl)-phenyl-methylenejamino]oxymethyl]-2pyridyljcarbamate, dazomet, isotianil, tiadinil, thifluzamide, benthiazole (TCMTB), silthiofam, zoxamide, anilazine, tricyciazole, (.+-.)-cis-T(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cyctoheptanol (huanjunzuo), l-(5-bromo-2-pyridyl)-2-(2,4-difiuorophenyi)-1,1-difluoro-3-(1,2,4triazol-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-mettiyl-2“propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine), azaconazole, bitertanol (biloxazol), bromuconazole, ciimbazole, 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-[[(1 R,5S)-5-[(4-fluorophenyl)methyl]-1-hydroxy-2,2-dimethylcyclopentyl]methyl]-4H-1I214-triazo!e-34hione 2-[[3-(2-chlorophenyl)-2-(2,4difluorophenyl)oxiran-2-yl]methyl]-4H-1,2,4-tnazole-3-thione, ametoctradin (imidium), iprovalicarb, valifenalate, 2-benzyl-4-chlorophenoi (Chlorophene), allyl alcohol, azafenidin, benzalkonium chloride, chloropicrin, cresol, daracide, dichtorophen (dichlorophene), difenzoquat, dipyrithione, N-(2-p-chlorobenzoylethyl)-hexaminium chloride, NNF-0721, octhilinone, oxasulfuron, a plant extract comprising tea tree oil Metaieuca aitemifolia (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-methyi, chromafenozide, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhatothrin, lambda-cyhalothrin, cypemnethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieidrin, diflubenzuron, dimefluthrin, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan,
132 esfenvaierate, ethiprole, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, tau-fluvalinate, flufenerim (UR-50701), flufenoxuron, fonophos, haiofenozrde, hexaflumuron, hydramethylnon, imidacloprid, îndoxacarb, isofenphos, lufenuron, malathion, metaflumizone, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, nitenpyram, nithiazine, novaluron, noviflumuron (XDE-007), oxamyi, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, pymetrozine, pyrafluprole, pyrethrin, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, retenons, 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 bactéricide selected from streptomycin; or an acaricide selected from amitraz, chinomethionat, chlorobenzilate, cyenopyrafen, cyhexatin, dicofol, dienochlor, etoxazote, 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 any one of daims 1 to 12, wherein the composition further comprises an agriculturally acceptable carrier and, optîonally, 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 any one of daims 1 to 12.
15. A method according to daim 14, wherein the composition components (A) and (B) are appiied in a sequential manner.
OA1202200355 2020-03-05 2021-03-05 Fungicidal compositions OA20876A (en)

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