WO2018177880A1 - Compositions fongicides - Google Patents

Compositions fongicides Download PDF

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Publication number
WO2018177880A1
WO2018177880A1 PCT/EP2018/057295 EP2018057295W WO2018177880A1 WO 2018177880 A1 WO2018177880 A1 WO 2018177880A1 EP 2018057295 W EP2018057295 W EP 2018057295W WO 2018177880 A1 WO2018177880 A1 WO 2018177880A1
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WIPO (PCT)
Prior art keywords
methyl
phenyl
compound
component
trifluoromethyl
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PCT/EP2018/057295
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English (en)
Inventor
Thomas James HOFFMAN
Daniel Stierli
Renaud Beaudegnies
Martin Pouliot
Ulrich Johannes Haas
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Syngenta Participations Ag
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Priority to BR112019020134-3A priority Critical patent/BR112019020134B1/pt
Publication of WO2018177880A1 publication Critical patent/WO2018177880A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles

Definitions

  • the present invention relates to novel fungicidal compositions, to their use in agriculture or horticulture for controlling diseases caused by phytopathogens, especially phytopathogenic fungi, and to methods of controlling diseases on useful plants.
  • oxadiazole derivatives are known as insecticidal and acaricidal agents, e.g., from CN 1927860.
  • WO 2013/064079, EP 0 276 432 and WO 2015/185485 describe the use of substituted oxadiazoles for combating phytopathogenic fungi.
  • compositions comprising mixtures of different fungicidal compounds possessing different modes of action can address some of these needs (e.g., by combining fungicides with differing spectrums of activity).
  • fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is a compound of formula (I):
  • R represents hydrogen or fluoro
  • R 2 represents hydrogen or fluoro; represents hydrogen;
  • Z represents -NR 5 R 6 , wherein R 5 is methyl, ethyl, methoxy or ethoxy;
  • R 6 is hydrogen, methyl or ethyl; or a salt or an N-oxide thereof; and component (B) is selected from the group consisting of: benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, flutriafol, mefentrifluconazole, ipconazole, paclobutrazol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metalaxyl-M, fenpropidin, fenpropimorph, cyprodinil, spiroxamine, mancozeb, chlorothalonil, oxa
  • 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 :40, 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.
  • 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 according to the invention.
  • fungicidal mixture compositions according to the invention may also include, inter alia, advantageous levels of biological activity for protecting plants against diseases that are caused by fungi or superior properties for use as agrochemical active ingredients (for example, greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased biodegradability).
  • the presence of one or more possible asymmetric carbon atoms in a compound of Formula (I) means that the compounds may occur in optically isomeric forms, i.e., enantiomeric or diastereomeric forms. Also atropisomers may occur as a result of restricted rotation about a single bond.
  • the present invention includes all those possible isomeric forms (e.g. geometric isomers) and mixtures thereof for a compound of Formula (I).
  • the present invention includes all possible tautomeric forms for a compound of Formula (I), and also a racemic compound, i.e., a mixture of at least two enantiomers in a ratio of substantially 50:50.
  • the compounds of Formula (I) according to the invention are in free form, in oxidized form as an N-oxide or in salt form, e.g. an agronomically usable salt form.
  • N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen containing heteroaromatic compounds. They are described for instance in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.
  • R and R 2 are each independently hydrogen or fluoro;
  • R 3 is hydrogen
  • Z is -NR 5 R 6 , wherein R 5 is methyl, ethyl, methoxy or ethoxy;
  • R 6 is hydrogen, methyl or ethyl
  • component (A) is a compound according to Formula (I) selected from:
  • component (A) is a compound according to Formula (I) selected from:
  • component (A) is a compound according to Formula (I) selected from:
  • component (A) is a compound according to Formula (I) which is N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (compound X.01 ).
  • component (B) is a compound selected from the group consisting of: benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, flutriafol, mefentrifluconazole, ipconazole, paclobutrazol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metalaxyl-M, fenpropidin, fenpropimorph, cyprodinil, spiroxamine, mancozeb, chlorothalonil, oxathiapiprolin, mandipropamid, fluazinam, fludi
  • component (B) is a compound selected from the group consisting of:
  • component (B) is a compound selected from the group consisting of: benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-nriethyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine).
  • the component (B) compounds are referred to herein and above by a so-called "ISO common 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.
  • component (A) is compound no. X.01 , N-
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl
  • component (A) is compound no. X.02, 2,2-dimethyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]but-3-ynamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N) is compound selected from the group consist
  • component (A) is compound no. X.03, N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5-bromo-2
  • component (A) is compound no. X.04, 3-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5-brovindiflupyr, fluxap
  • component (A) is compound no. X.05, 2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]prop-2-enamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5
  • component (A) is compound no. X.06, 2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5-brovindiflupyr, fluxap
  • component (A) is compound no. X.07, 2-methoxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5
  • component (A) is compound no. X.08 3,3,3-trifluoro-N-[[3-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil
  • component (A) is compound no. X.09, 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil
  • component (A) is compound no. X.10, N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'
  • component (A) is compound no. X.1 1 , N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro- propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancoze
  • component (A) is compound no. X.12, 2-(difluoromethoxy)-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and
  • component (A) is compound no. X.13, 2-methoxy-2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N')
  • component (A) is compound no. X.14, 1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5-bromo
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-
  • component (A) is compound no. X.16, 1-ethoxy-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5-brovindiflupyr, fluxap
  • component (A) is compound no. X.17, 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[
  • component (A) is compound no. X.18, 1 , 1-diethyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-
  • component (A) is compound no. X.01 , N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl- N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.02, 2,2-dimethyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]but-3-ynamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.03, N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl- N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.04, 3-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.05, 2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]prop-2-enamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.06, 2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.07, 2-methoxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.08, 3,3,3-trifluoro-N-[[3-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl- 6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15:1 to 1
  • component (A) is compound no. X.09, 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl- 6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :
  • component (A) is compound no. X.10, N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.1 1 , N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro- propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15
  • component (A) is compound no. X.12, 2-(difluoromethoxy)-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.13, 2-methoxy-2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl- 6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.14, 1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.15, 1-ethyl-1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.16, 1-ethoxy-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.17, 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.18, 1 , 1-diethyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 15: 1 to 1 :30.
  • component (A) is compound no. X.01 , N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5-brovindiflupyr, fluxapyrox
  • component (A) is compound no. X.02, 2,2-dimethyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]but-3- ynamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil,
  • component (A) is compound no. X.03, N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5-brom
  • component (A) is compound no. X.04, 3-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5
  • component (A) is compound no. X.05, 2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]prop-2- enamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N')
  • component (A) is compound no. X.06, 2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5
  • component (A) is compound no. X.07, 2-methoxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N')
  • component (A) is compound no. X.08, 3,3,3-trifluoro-N-[[3-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlor
  • component (A) is compound no. X.09, 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chloro
  • component (A) is compound no. X.10, N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and
  • component (A) is compound no. X.1 1 , N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3- trifluoro-propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, man
  • component (A) is compound no. X.12, 2-(difluoromethoxy)-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]acetamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalon
  • component (A) is compound no. X.13, 2-methoxy-2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and
  • component (A) is compound no. X.14, 1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5-brovindiflupyr, fluxapyrox
  • component (A) is compound no. X.15, 1-ethyl-1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N)
  • component (A) is compound no. X.16, 1-ethoxy-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N'-[5
  • component (A) is compound no. X.17, 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N)
  • component (A) is compound no. X.18, 1 , 1-diethyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, mefentrifluconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, and (N)
  • component (A) is compound no. X.01 , N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-nriethyl-6-(1-nriethyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl- N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10: 1 to 1 :10 (or even
  • component (A) is compound no. X.02, 2,2-dimethyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]but-3-ynamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10: 1 to 1 :10 (or even more
  • component (A) is compound no. X.03, N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl- N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10: 1 to 1 :10 (or even more preferably, 5:1 to 1
  • component (A) is compound no. X.04, 3-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10: 1 to 1 :10 (or even more preferably, 5: 1
  • component (A) is compound no. X.05, 2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]prop-2-enamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10: 1 to 1 : 10 (or even more preferably, 5
  • component (A) is compound no. X.06, 2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10: 1 to 1 :10 (or even more preferably, 5: 1
  • component (A) is compound no. X.07, 2-methoxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10: 1 to 1 :10 (or even more preferably, 5
  • component (A) is compound no. X.08, 3,3,3-trifluoro-N-[[3-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl- 6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10:1 to 1
  • component (A) is compound no. X.09, 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl- 6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10:1 to 1 :
  • component (A) is compound no. X.10, N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]butanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10:1 to 1 :10 (or even more
  • component (A) is compound no. X.1 1 , N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro- propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2- propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10
  • component (A) is compound no. X.12, 2-(difluoromethoxy)-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10:1 to 1 :10 (or
  • component (A) is compound no. X.13, 2-methoxy-2-methyl-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl- 6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10:1 to 1 : 10 (or even more
  • component (A) is compound no. X.14, 1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10:1 to 1 :10 (or even more preferably, 5: 1 to 1
  • component (A) is compound no. X.15, 1-ethyl-1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10:1 to 1 :10 (or even more preferably
  • component (A) is compound no. X.16, 1-ethoxy-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10:1 to 1 :10 (or even more preferably, 5: 1
  • component (A) is compound no. X.17, 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10: 1 to 1 : 10 (or even more preferably,
  • component (A) is compound no. X.18 1 , 1-diethyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]urea or a salt, enantiomer, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of benzovindiflupyr, pydiflumetofen, difenoconazole, cyproconazole, hexaconazole, prothioconazole, azoxystrobin, fenpropidin, and (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)- 3-pyridyl]-N-ethyl-N-methyl-formamidine) wherein the weight ratio of component (A) to component (B) is from 10: 1 to 1 : 10 (or even more preferably,
  • fungicide as used herein means a compound that controls, modifies, or prevents the growth of fungi.
  • fungicidally effective amount means the quantity 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 all deviation from natural development, such as killing, retardation and the like, and prevention includes barrier or other defensive formation in or on a plant to prevent fungal infection.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
  • plant propagation material denotes all generative parts of a plant, for example seeds or vegetative 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.
  • locus means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.
  • composition stands for the various mixtures or combinations of components (A) and (B) (including the above-defined embodiments), for example in a single “ready-mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a "tank-mix", and in a combined use of the single active ingredients 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 essential for working the present invention.
  • the composition according to the invention is effective against harmful microorganisms, such as microorganisms that cause phytopathogenic diseases, in particular against phytopathogenic fungi and bacteria.
  • the composition of the 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 ornamental, turf, vegetable, field, cereal, and fruit crops.
  • 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 citricola, Phytophthora citrophthora and Phytophthora erythroseptica; Pythium diseases such as those caused by Pythium aphanidermatum, Pythium arrhenomanes, Pythium graminicola, Pythium irregulare and Pythium ultimum; diseases caused by Peronosporales such as Peronospora destructor, Peronospora parasitica, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cubensis, Albugo Candida, Sclerophthora macrospora and Br
  • Ascomycetes including blotch, spot, blast or blight diseases and/or rots for example those caused by Pleosporales such as Stemphylium solani, Stagonospora tainanensis, Spilocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, Ophiosphaerella graminicola, Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus, Bi
  • Valsa ceratosperma and others such as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Asperisporium caricae, Blumeriella jaapii, Candida spp.
  • Gerlachia nivale Gibberella fujikuroi
  • Gibberella zeae Gibberella zeae
  • Gliocladium spp. Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride, Trichothecium 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, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp.
  • Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae
  • rusts for example those caused by Pucciniales such as Cerotelium fici, Chr
  • Puccinia striiformis f.sp. Secalis Pucciniastrum coryli, or Uredinales such as Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor and Uromyces viciae-fabae; and other rots and diseases such as those caused by Cryptococcus spp., Exobasidium vexans, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Tha
  • Blastocladiomycetes such as Physoderma maydis
  • Mucoromycetes such as Choanephora cucurbitarum.; Mucor spp.; Rhizopus arrhizus;
  • compositions may also have activity against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scabies and other related species as well as certain protozoa.
  • bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scabies and other related species as well as certain protozoa.
  • composition according to the invention is particularly effective against phytopathogenic fungi belonging to the following classes: Ascomycetes (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.
  • Ascomycetes 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, Septoria, 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 annual 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; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (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.
  • perennial and annual crops such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries
  • cereals for example barley, maize (corn), mille
  • Augustine grass and Zoysia grass herbs such as basil, borage, chives, coriander, lavender, 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, coconut, 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 vines for example grapes.
  • herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme
  • legumes for example beans, lentils, peas and soya beans
  • Crops are to be understood as being those which are naturally occurring, obtained by conventional methods of breeding, or obtained by genetic engineering. They include crops which contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour).
  • output traits e.g. improved storage stability, higher nutritional value and improved flavour.
  • Crops are to be understood as also including those crops which have been rendered tolerant to herbicides like bromoxynil or classes of herbicides such as ALS-, EPSPS-, GS-, HPPD- and PPO- inhibitors.
  • herbicides like bromoxynil or classes of herbicides such as ALS-, EPSPS-, GS-, HPPD- and PPO- inhibitors.
  • An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer canola.
  • crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names Round upReady®, Herculex I® and LibertyLink®.
  • Crops are also to be understood as being those which naturally are or have been rendered resistant 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 ⁇ -endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi.
  • Vip vegetative insecticidal proteins
  • insecticidal proteins of bacteria colonising nematodes and toxins produced by scorpions, arachnids, wasps and fungi.
  • An example of a crop that 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 insecticidal resistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds).
  • Crops or seed material thereof can also be resistant to multiple types of pests (so-called stacked transgenic events when created by genetic modification).
  • a plant can have the ability to express an insecticidal protein while at the same time being herbicide tolerant, for example Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).
  • the compounds of Formula (I) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) on soy bean plants.
  • transgenic soybean plants expressing toxins for example insecticidal proteins such as delta-endotoxins, e.g. CrylAc (Cry1 Ac Bt protein).
  • toxins for example insecticidal proteins such as delta-endotoxins, e.g. CrylAc (Cry1 Ac Bt protein).
  • 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 A1 (e.g., see paragraph [008] reference to Intacta RR2 PROTM soybean)), event MON87751 (US. Patent Application Publication No. 2014/0373191 ) or event DAS- 81419 (U.S. Patent No. 8632978 and related applications and patents).
  • event MON87701 see U.S. Patent No. 8,049,071 and related applications and patents, as well as WO 2014/170327 A1 (e.g., see paragraph [008
  • 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
  • event DAS-40278-9 - tolerance to 2,4- dichlorophenoxyacetic acid and aryloxyphenoxypropionate see WO 201 1/022469, WO 201 1/022470, WO 201 1/022471 , 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-68416-4- 2,4-dichlorophenoxyacetic acid and glufosinate tolerance
  • event FG72 - glyphosate and isoxaflutole tolerance event BPS-CV127-9 - ALS tolerance and GU262 - glufosinate tolerance or event SYHT04R
  • the compounds of Formula (I) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) on soy bean plants.
  • phytopathogenic diseases especially phytopathogenic fungi (such as Phakopsora pachyrhizi)
  • soy bean plants there are known in the scientific literature certain Elite soybean plant varieties where R-gene stacks, conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, have been been introgressed in the plant genome, see for example: “Fighting Asian Soybean Rust", Langenbach C, ef al, Front Plant Science 7(797) 2016).
  • An elite plant is any plant from an elite line, such that an elite plant is a representative plant from an elite variety.
  • 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, Iowa, USA); BPR0144RR, BPR 4077NRR and BPR 4390NRR (Bio Plant Research, Camp Point, III., USA); DKB17-51 and DKB37-51 (DeKalb Genetics, DeKalb, III., USA); DP 4546 RR, and DP 7870 RR (Delta & Pine Land Company, Lubbock,
  • the compounds of Formula (I) are used to control Phakopsora pachyrhizi, (including fungicidally-resistant strains thereof, as outlined above) on Elite soybean plant varieties where R-gene stacks, conferring a degree of immunity or resistance to specific Phakopsora pachyrhizi, have been been introgressed in the plant genome. Numerous benefits may be expected to ensue from said use, e.g. improved biological activity, an advantageous or broader spectrum of activity (inc.
  • Phakopsora pachyrhizi sensitive and resistant strains of Phakopsora pachyrhizi
  • an increased safety profile improved crop tolerance, synergistic interactions or potentiating properties, improved onset of action or a longer lasting residual activity, a reduction in the number of applications and/or a reduction in the application rate of the compounds and compositions required for effective control of the phytopathogen (Phakopsora pachyrhizi), thereby enabling beneficial resistance-management practices, reduced environmental impact and reduced operator exposure.
  • fungicidal compositions according to the present invention comprising a compound of Formula (I) 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 ingredients.
  • phytopathogenic diseases especially phytopathogenic fungi (such as Phakopsora pachyrhizi) on soy bean plants (in particular any of the transgenic soybean plants as described above)
  • soy bean plants in particular any of the transgenic soybean plants as described above
  • the compounds of Formula (I) may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (in particular, Phakopsora pachyrhizi) on soybean plants.
  • fungicidal-resistant strains of Phakopsora pachyrhizi have been reported in the scientific literature, with strains resistant to one or more fungicides from at least each of the following fungicidal mode of action classes being observed: sterol demethylation-inhibitors (DMI), quinone-outside-inhibitors (Qol) and succinate dehydrogenase inhibitors (SDHI).
  • DMI sterol demethylation-inhibitors
  • Qol quinone-outside-inhibitors
  • SDHI succinate dehydrogenase inhibitors
  • the compounds of Formula (I) are used to control Phakopsora pachyrhizi which are resistant to one or more fungicides from any of the following fungicidal MoA classes: sterol demethylation-inhibitors (DMI), quinone-outside- inhibitors (Qol) and succinate dehydrogenase inhibitors (SDHI).
  • DMI sterol demethylation-inhibitors
  • Qol quinone-outside- inhibitors
  • SDHI succinate dehydrogenase inhibitors
  • the compounds of Formula (I) according to the invention may be present in a reversible equilibrium with the corresponding covalently hydrated forms (i.e., the compounds of Formula (l-la) and Formula (l-lla) as shown below, which may exist in tautomeric form as the compounds of Formula (l-lb) and Formula (l-llb)) at the CF3-oxadiazole motif.
  • This dynamic equilibrium may be important for the biological activity of the compounds of Formula (I).
  • R , R 2 , R 3 , Z, R 4 , R 5 , and R 6 with reference to the compounds of Formula (I) of the present invention apply generally to the compounds of Formula (l-la), Formula (l-lla), Formula (l-lb), and Formula (l-llb), as well as to the specific disclosures of combinations of, R , R 2 , R 3 , Z, R 4 , R 5 , and R 6 as represented in the compounds X.01 to X.18 described in Table X (above) or Table T1 (below).
  • the compounds of Formula (I) can be obtained via coupling transformations with compounds of Formula (II) and compounds of Formula (III), wherein X is halogen, ester [e.g., OMe or OEt)], anhydride [e.g., OC(H)0, or OAc], or OH, preferably halogen, in a suitable solvent (e.g., dimethylformamide, dichloromethane, or tetrahydrofuran), preferably at temperatures between 25°C and 100°C, and optionally in the presence of a base (e.g., NaHC03, Na2C03, K2CO3, NaOH, triethylamine or N,N- diisopropylethylamine), or under conditions described in the literature for an amide or urea coupling, for example by using BOP-CI or HATU.
  • a suitable solvent e.g., dimethylformamide, dichloromethane, or tetrahydrofuran
  • a base
  • compounds of Formula (I), wherein Z represents R 4 can optionally be obtained via coupling transformations with compounds of Formula (II) and compounds of Formula (III), wherein X is OH, via processes that convert the OH into an improved halide leaving group, such as a chloride, for example by using triphosgene, diphosgene, phosgene, (COCI)2, or SOCI2, prior to treatment with the compounds of Formula (II).
  • Compounds of Formula (III) are commercially available or prepared using known methods. For related examples, see Nelson, T. D ef al Tetrahedron Lett.
  • compounds of Formula (I), wherein Z represents R 4 can be prepared via reactions of compounds of Formula (II) with triphosgene, diphosgene, or phosgene in a suitable solvent (e.g., ethyl acetate, chloroform, acetone, or toluene), followed by a reaction with nucleophiles of Formula (IV), wherein Z-Nu represents an R 4 -Metal organometallic reagent (e.g., an organomagnesium, organozinc, or organolithium), in a suitable solvent (e.g., toluene, diethyl ether or tetrahydrofuran), at temperatures between -78°C and 25°C.
  • a suitable solvent e.g., ethyl acetate, chloroform, acetone, or toluene
  • compounds of Formula (I), wherein Z represents -NR 6 R 7 can be prepared via reactions of compounds of Formula (II) with triphosgene, diphosgene, or phosgene in a suitable solvent (e.g., 1 ,2-dichloroethane, acetonitrile, ethyl acetate, chloroform, or toluene) followed by the addition of nucleophiles of Formula (IV), wherein Z-Nu represents HNR 6 R 7 , in the presence of a suitable base, such as pyridine, K2CO3, or trieth lamine.
  • a suitable base such as pyridine, K2CO3, or trieth lamine.
  • compounds of Formula (I) can be prepared from compounds of Formula (V) by treatment with trifluoroacetic acid, trifluoroacetic ester, trifluoroacetic anhydride, or trifluoroacetyl halide (including trifluoroacetyl fluoride, trifluoroacetyl chloride and trifluoroacetyl bromide), optionally in the presence of a base (e.g., pyridine or 4-dimethylaminopyridine) in a suitable solvent, (e.g., toluene, ethyl acetate, tetrahydrofuran, 2-methyl tetrahydrofuran, or ethanol), at temperatures between 0°C and 75°C.
  • a base e.g., pyridine or 4-dimethylaminopyridine
  • a suitable solvent e.g., toluene, ethyl acetate, tetrahydrofuran, 2-methyl tetrahydr
  • Compounds of Formula (V) can be prepared from compounds of Formula (VI) by treatment with a hydroxylamine hydrochloride salt or a hydroxylamine solution in water, in the presence of a base, such as triethylamine or potassium carbonate, in a suitable solvent, such as methanol or ethanol, at temperatures between 0°C and 80°C.
  • a catalyst e.g., 8-hydroxyquinoline.
  • Compounds of Formula (VI) are commercially available or can be prepared from compounds of Formula (VII), wherein Y is formyl, CI, Br, or I, via a metal-promoted reactions with a suitable cyanide reagent, such as acetone cyanohydrin, dimethylmalononitrile, K4[Fe(CN)6] , Zn(CN)2, NaCN, or CuCN, in a suitable solvent (e.g., dimethylformamide or N-methylpyrrolidone) at elevated temperatures between 80°C and 120°C, and optionally in the presence of a metal catalyst (e.g., Pd or Ni) or a Grignard or organolithium reagent.
  • a metal catalyst e.g., Pd or Ni
  • a Grignard or organolithium reagent for related examples, see Reeves, J.
  • compounds of Formula (VI) can be prepared from compounds of Formula (VII), wherein Y is NH2, via a radical-nucleophilic aromatic substitution reactions in the presence of a nitrite source (e.g., NaN02 or /so-amylnitrite), an acid (e.g., hydrochloric acid or HBF4), and a copper source (e.g., CuCN) in an acceptable solvent system, such as aqueous acetonitrile, at suitable temperatures between 0°C to 100°C.
  • a nitrite source e.g., NaN02 or /so-amylnitrite
  • an acid e.g., hydrochloric acid or HBF4
  • a copper source e.g., CuCN
  • an acceptable solvent system such as aqueous acetonitrile
  • Compounds of Formula (II) can be prepared from aldehyde compounds of Formula (IX), via reactions with compounds of Formula (VIII), in a suitable solvent, (e.g., tetrahydrofuran) at temperatures between 25°C and 75°C followed by the addition of a reducing reagent, such as NaBh CN, in a suitable solvent, (e.g., tetrahydrofuran or ethanol) at temperatures between 0°C and 25°C.
  • a suitable solvent e.g., tetrahydrofuran
  • a suitable solvent e.g., tetrahydrofuran or ethanol
  • compounds of Formula (II) can be prepared from compounds of Formula (X), wherein X is CI, Br, I, or OS02Me, via reactions with amines of Formula (VIII) in a suitable solvent (e.g., tetrahydrofuran) at temperatures between 25°C and 60°C.
  • a suitable solvent e.g., tetrahydrofuran
  • Compounds of Formula (X) can be prepared from compounds of Formula (XI), wherein X is CI or 5 Br, via reactions with a halogen source [e.g., N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS)] and a radical initiator [e.g., (PhC02)2 or azobisisobutyronitrile (AIBN)] in a suitable solvent, such as tetrachloromethane, at temperatures between 55°C and 100°C, optionally in the presence of ultraviolet light.
  • a halogen source e.g., N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS)
  • a radical initiator e.g., (PhC02)2 or azobisisobutyronitrile (AIBN)
  • suitable solvent such as tetrachloromethane
  • halogen ester [e.g., OMe or OEt)], anhydride [e.g., OC(H)0, or OAc], or OH, preferably halogen, in a suitable solvent (e.g., dimethylformamide, dichloromethane, tetrahydrofuran, or 2-methyl tetrahydrofuran), preferably at temperatures between 0°C and 100°C, and optionally in the presence of a base (e.g., NaHC03, Na2C03, K2CO3, NaOH, triethylamine or A/,A/-diisopropylethylamine), or under conditions described in the literature for an amide or urea coupling, for example by using BOP-CI or
  • compounds of Formula (VII), wherein Z represents R 4 can optionally be obtained via coupling transformations with compounds of Formula (XII) and compounds of Formula (III), wherein X is OH, in a process that converts the -OH into an improved halide leaving group, such as a chloride, for example by using triphosgene, diphosgene, or phosgene, (COCI)2, or SOCI2, prior to treatment with the compounds of Formula (XII).
  • an improved halide leaving group such as a chloride
  • compounds of Formula (VII), wherein Y is NH2, CI, Br, I, or CN and Z represents - R 4 can be prepared via reactions of compounds of Formula (XII) with triphosgene, diphosgene, or phosgene in a suitable solvent (e.g., ethyl acetate, acetone, chloroform, or toluene), followed by a reaction with nucleophiles of Formula (IV), wherein Z-Nu represents an R 4 -Metal organometallic reagent (e.g., an organomagnesium, organozinc, or organolithium), in a suitable solvent (e.g., toluene, diethyl ether, or tetrahydrofuran), at temperatures between -78°C and 25°C.
  • a suitable solvent e.g., ethyl acetate, acetone, chloroform, or toluene
  • compounds of Formula (VII), wherein Z represents -NR 6 R 7 can be prepared via reactions of compounds of Formula (XII) with triphosgene, diphosgene, or phosgene in a suitable solvent (e.g., 1 ,2-dichloroethane, water, acetonitrile, ethyl acetate, chloroform, or toluene), followed by the addition of suitable nucleophiles of Formula (IV), wherein Z-Nu represents HNR 6 R 7 , and in the presence of a suitable base, such as pyridine, K2CO3, or triethylamine.
  • a suitable solvent e.g., 1 ,2-dichloroethane, water, acetonitrile, ethyl acetate, chloroform, or toluene
  • suitable nucleophiles of Formula (IV) wherein Z-Nu represents HNR 6 R 7
  • a suitable base such as pyridine, K2CO3, or triethy
  • Compounds of Formula (XII), wherein Y is formyl, NH2, CI, Br, I, or CN can be prepared from compounds of Formula (XIII), wherein X is CI, Br, I, or OSCteMe, via reactions with amines of Formula (VIII), in the presence of a suitable base (e.g., NaHCCh, Na2C03, K2CO3, or NaH) in a suitable solvent, (e.g., dimethylformamide, N-methylpyrolidine, or acetonitrile) at temperatures between 0°C and 100°C.
  • a suitable base e.g., NaHCCh, Na2C03, K2CO3, or NaH
  • a suitable solvent e.g., dimethylformamide, N-methylpyrolidine, or acetonitrile
  • an improved reaction performance may be gained via the use of a catalyst (e.g., BU4NHSO4, Bu4NBr, BU4NI, Nal, or 4-dimethylaminopyridine) or optionally with microwaves irradiation.
  • a catalyst e.g., BU4NHSO4, Bu4NBr, BU4NI, Nal, or 4-dimethylaminopyridine
  • microwaves irradiation See Miyawaki, K. ef al. Heterocycles (2001 ), 54, 887. This reaction is shown in Scheme 1 1.
  • compounds of Formula (XIII), wherein X is CI, Br, I, or OSCteMe and Y is formyl, NH2, CI, Br, I, CN, or 5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl are either commercially available or can be prepared from compounds of formula (XV), via reactions with an acid source (e.g., hydrochloric acid, hydrobromic acid, or hydroiodic acid) or a halogen source (e.g., tetrabromomethane, tetrachloromethane, or iodine) in the presence of triphenylphosphine, or with methanesulfonyl chloride (CISC Me), in a suitable solvent (e.g., dichloromethane), optionally in the presence of a base (e.g., triethylamine), at temperatures between 0°C and 100°C.
  • an acid source e.g., hydrochloric
  • compounds of Formula (VII), wherein Y is formyl, NH2, CI, Br, I, CN, or 5- (trifluoromethyl)-1 ,2,4-oxadiazol-3-yl can be prepared from compounds of Formula (XIII), wherein X is a suitable leaving group (e.g., CI, Br, I, OH, or OSCteMe) via reactions with amides or ureas of Formula (XVI) in the presence of a base (e.g., triethylamine, A/,A/-diisopropylethylamine, K2CO3, NaHCCh, or Na2C03) in a suitable solvent (e.g., dimethylacetamide, tetrahydrofuran, 2-methyltetrahydrofuran, acetone, or acetonitrile) at temperatures between 0°C and 90°C.
  • a base e.g., triethylamine, A/,A/-diiso
  • a better reaction performance may be gained from the use of a catalyst (e.g., BU4NHSO4, Bu4NBr, BU4NI, Nal, or 4- dimethylaminopyridine) or optionally with microwaves irradiation.
  • a catalyst e.g., BU4NHSO4, Bu4NBr, BU4NI, Nal, or 4- dimethylaminopyridine
  • microwaves irradiation e.g., BU4NHSO4, Bu4NBr, BU4NI, Nal, or 4- dimethylaminopyridine
  • compounds of Formula (XVII) can be prepared from compounds of Formula (XII), wherein Y is NH2, via radical-nucleophilic aromatic substitutions reaction using a nitrite source (e.g., NaN02 or iso-amylnitrite), an acid (e.g., hydrochloric acid or HBF4), and a copper source (e.g., CuCN) in an acceptable solvent, such as aqueous acetonitrile, at temperatures between 0°C to 100°C.
  • a nitrite source e.g., NaN02 or iso-amylnitrite
  • an acid e.g., hydrochloric acid or HBF4
  • a copper source e.g., CuCN
  • Compounds of Formula (XIX), wherein T is CH3, CH2OH, NH2, CN, CI, Br, or I, can be prepared from compounds of Formula (XX), via reactions with a hydroxylamine hydrochloride salt or a hydroxylamine solution in water in the presence of a base, such as triethylamine or potassium carbonate, in a suitable solvent, such as methanol or ethanol, at temperatures between 0°C and 80°C.
  • a base such as triethylamine or potassium carbonate
  • suitable solvent such as methanol or ethanol
  • Compounds of Formula (XII), wherein Y is CN, CI, Br, or I, can be prepared from aldehyde compounds of Formula (XXI), via condensation reactions with amines of Formula (VIII), in a suitable solvent (e.g., tetrahydrofuran or methanol) at temperatures between 25°C and 75°C, followed by the addition of a reducing reagent, such as NaBh CN, in a suitable solvent (e.g., tetrahydrofuran or ethanol) at temperatures between 0°C and 25°C.
  • a suitable solvent e.g., tetrahydrofuran or ethanol
  • compositions of this invention can be mixed with one or more further pesticides including further fungicides, insecticides, nematocides, bactericides, 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.
  • further pesticides including further fungicides, insecticides, nematocides, bactericides, 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.
  • Fungicides such as etridiazole, fluazinam, benalaxyl, benalaxyl-M (kiralaxyl), furalaxyl, metalaxyl, metalaxyl-M (mefenoxam), dodicin, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl- formamidine, N'-[4-(4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, N'-[4-[[3-[(4-chlorophenyl)methyl]-1 , 2, 4-th iadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-m ethyl- formamidine, ethirimol, 3'-chloro-2-methoxy-N
  • Insecticides such as abamectin, acephate, acetamiprid, amidoflumet (S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, buprofezin, carbofuran, cartap, chlorantraniliprole (DPX-E2Y45), chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimethoate, dinote
  • Bactericides 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 Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.
  • TX represents a compound (according to the definition of component (A) of the compositions of the present invention) selected from compound no. X.01 , X.02, X.03, X.04, X.05, X.06, X.07, X.08, X.09, X.10, X.1 1 , X.12, X.13, X.14, X.15, X.16, X.17 or X.18, as defined in the Table X above or Table T1 below):
  • an adjuvant selected from the group of substances consisting of petroleum oils (alternative name) (628) + TX,
  • an acaricide selected from the group of substances consisting of 1 ,1-bis(4-chlorophenyl)-2- ethoxyethanol (lUPAC name) (910) + TX, 2,4-dichlorophenyl benzenesulfonate (lUPAC/Chemical Abstracts name) (1059) + TX, 2-fluoro-A/-methyl-A/-1-naphthylacetamide (lUPAC name) (1295) + TX, 4- chlorophenyl phenyl sulfone (lUPAC name) (981 ) + TX, abamectin (1 ) + TX, acequinocyl (3) + TX, acetoprole [CCN] + TX, acrinathrin (9) + TX, aldicarb (16) + TX, aldoxycarb (863) + TX, alpha- cypermethrin (202) + TX, amidithion (870) + TX, amid
  • an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (lUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347) + TX,
  • an anthelmintic selected from the group of substances consisting of abamectin (1 ) + TX, crufomate (101 1 ) + TX, doramectin (alternative name) [CCN] + TX, emamectin (291 ) + TX, emamectin benzoate (291 ) + TX, eprinomectin (alternative name) [CCN] + TX, ivermectin (alternative name) [CCN] + TX, milbemycin oxime (alternative name) [CCN] + TX, moxidectin (alternative name) [CCN] + TX, piperazine [CCN] + TX, selamectin (alternative name) [CCN] + TX, spinosad (737) and thiophanate (1435) + TX,
  • an avicide selected from the group of substances consisting of chloralose (127) + TX, endrin (1 122) + TX, fenthion (346) + TX, pyridin-4-amine (lUPAC name) (23) and strychnine (745) + TX, a bactericide selected from the group of substances consisting of 1 -hydroxy- 1 /- -pyridine-2- thione (lUPAC name) (1222) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, 8-hydroxyquinoline sulfate (446) + TX, bronopol (97) + TX, copper dioctanoate (lUPAC name) (170) + TX, copper hydroxide (lUPAC name) (169) + TX, cresol [CCN] + TX, dichlorophen (232) + TX, dipyrithione (1 105) + TX, dodicin (1 1
  • a biological agent selected from the group of substances consisting of Adoxophyes orana GV (alternative name) (12) + TX, Agrobacterium radiobacter (alternative name) (13) + TX, Amblyseius spp. (alternative name) (19) + TX, Anagrapha falcifera NPV (alternative name) (28) + TX, Anagrus atomus (alternative name) (29) + TX, Aphelinus abdominalis (alternative name) (33) + TX, Aphidius colemani (alternative name) (34) + TX, Aphidoletes aphidimyza (alternative name) (35) + TX, Autographa californica NPV (alternative name) (38) + TX, Bacillus firmus (alternative name) (48) + TX, Bacillus sphaericus Neide (scientific name) (49) + TX, Bacillus thuringiensis Hopkins (scientific name) (
  • a soil sterilant selected from the group of substances consisting of iodomethane (lUPAC name)
  • a chemosterilant selected from the group of substances consisting of apholate [CCN] + TX, bisazir (alternative name) [CCN] + TX, busulfan (alternative name) [CCN] + TX, diflubenzuron (250) + TX, dimatif (alternative name) [CCN] + TX, hemel [CCN] + TX, hempa [CCN] + TX, metepa [CCN] + TX, methiotepa [CCN] + TX, methyl apholate [CCN] + TX, morzid [CCN] + TX, penfluron (alternative name) [CCN] + TX, tepa [CCN] + TX, thiohempa (alternative name) [CCN] + TX, thiotepa (alternative name) [CCN] + TX,
  • an insect pheromone selected from the group of substances consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol (lUPAC name) (222) + TX, (E)-tridec-4-en-1-yl acetate (lUPAC name) (829) + TX, (E)-6-methylhept-2-en-4-ol (lUPAC name) (541 ) + TX, (E,Z)-tetradeca-4,10-dien-1-yl acetate (lUPAC name) (779) + TX, (Z)-dodec-7-en-1-yl acetate (lUPAC name) (285) + TX, (Z)-hexadec- 11-enal (lUPAC name) (436) + TX, (Z)-hexadec-l 1-en-1-yl acetate (lUPAC name) (437) + TX, (Z)- hexade
  • an insect repellent selected from the group of substances consisting of 2-(octylthio)ethanol (lUPAC name) (591 ) + TX, butopyronoxyl (933) + TX, butoxy(polypropylene glycol) (936) + TX, dibutyl adipate (lUPAC name) (1046) + TX, dibutyl phthalate (1047) + TX, dibutyl succinate (lUPAC name) (1048) + TX, diethylamide [CCN] + TX, dimethyl carbate [CCN] + TX, dimethyl phthalate [CCN] + TX, ethyl hexanediol (1137) + TX, hexamide [CCN] + TX, methoquin-butyl (1276) + TX, methylneodecanamide [CCN] + TX, oxamate [CCN] and picaridin [CCN] + TX, an insecticide selected from the group
  • a molluscicide selected from the group of substances consisting of bis(tributyltin) oxide (lUPAC name) (913) + TX, bromoacetamide [CCN] + TX, calcium arsenate [CCN] + TX, cloethocarb (999) + TX, copper acetoarsenite [CCN] + TX, copper sulfate (172) + TX, fentin (347) + TX, ferric phosphate (lUPAC name) (352) + TX, metaldehyde (518) + TX, methiocarb (530) + TX, niclosamide (576) + TX, niclosamide-olamine (576) + TX, pentachlorophenol (623) + TX, sodium pentachlorophenoxide (623) + TX, tazimcarb (1412) + TX, thiodicarb (799) + TX, tributyltin oxide (913)
  • a nematicide selected from the group of substances consisting of AKD-3088 (compound code) + TX, 1 ,2-dibromo-3-chloropropane (lUPAC/Chemical Abstracts name) (1045) + TX, 1 ,2- dichloropropane (lUPAC/ Chemical Abstracts name) (1062) + TX, 1 ,2-dichloropropane with 1 ,3- dichloropropene (lUPAC name) (1063) + TX, 1 ,3-dichloropropene (233) + TX, 3,4- dichlorotetrahydrothiophene 1 , 1-dioxide (lUPAC/Chemical Abstracts name) (1065) + TX, 3-(4- chlorophenyl)-5-methylrhodanine (lUPAC name) (980) + TX, 5-methyl-6-thioxo-1 ,3,5-thiadiazinan-3- ylacetic acid (lUPAC name) (1286)
  • a nitrification inhibitor selected from the group of substances consisting of potassium ethylxanthate [CCN] and nitrapyrin (580) + TX,
  • a plant activator selected from the group of substances consisting of acibenzolar (6) + TX, acibenzolar-S-methyl (6) + TX, probenazole (658) and Reynoutria sachalinensis extract (alternative name) (720) + TX,
  • a rodenticide selected from the group of substances consisting of 2-isovalerylindan-1 ,3-dione (lUPAC name) (1246) + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide (lUPAC name) (748) + TX, alpha-chlorohydrin [CCN] + TX, aluminium phosphide (640) + TX, antu (880) + TX, arsenous oxide (882) + TX, barium carbonate (891 ) + TX, bisthiosemi (912) + TX, brodifacoum (89) + TX, bromadiolone (91 ) + TX, bromethalin (92) + TX, calcium cyanide (444) + TX, chloralose (127) + TX, chlorophacinone (140) + TX, cholecalciferol (alternative name) (850) + TX, coumachlor (1004) + TX, co
  • a synergist selected from the group of substances consisting of 2-(2-butoxyethoxy)ethyl piperonylate (lUPAC name) (934) + TX, 5-(1 ,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (lUPAC name) (903) + TX, farnesol with nerolidol (alternative name) (324) + TX, MB-599 (development code) (498) + TX, MGK 264 (development code) (296) + TX, piperonyl butoxide (649) + TX, piprotal (1343) + TX, propyl isomer (1358) + TX, S421 (development code) (724) + TX, sesamex (1393) + TX, sesasmolin (1394) and sulfoxide (1406) + TX,
  • an animal repellent selected from the group of substances consisting of anthraquinone (32) + TX, chloralose (127) + TX, copper naphthenate [CCN] + TX, copper oxychloride (171 ) + TX, diazinon (227) + TX, dicyclopentadiene (chemical name) (1069) + TX, guazatine (422) + TX, guazatine acetates (422) + TX, methiocarb (530) + TX, pyridin-4-amine (lUPAC name) (23) + TX, thiram (804) + TX, trimethacarb (840) + TX, zinc naphthenate [CCN] and ziram (856) + TX,
  • a virucide selected from the group of substances consisting of imanin (alternative name) [CCN] and ribavirin (alternative name) [CCN] + TX,
  • a wound protectant selected from the group of substances consisting of mercuric oxide (512) + TX, octhilinone (590) and thiophanate-methyl (802) + TX,
  • N-[(5-chloro-2-isopropyl- phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide can be prepared according to the procedures described in WO 2010/130767) + TX, 2,6-Dimethyl-1 H,5H- [1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetrone (can be prepared according to the procedures described in WO 2011/138281 ) + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1 ,4]dithiino[1 ,2-c]isothiazole-3- carbonitrile + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoramide
  • the mixtures of compounds of Formula (I) [selected from Table X (above)] with active ingredients described above comprise a compound selected from Table X (above) and an active ingredient as described above preferably in a mixing ratio of from 100:1 to 1 :6000, 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, very especially from 5: 1 and 1 :5, special 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 all 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, or 2:1 , 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 :
  • mixture compositions as described above can be used in a method for controlling pests, which comprises applying a composition comprising a mixture as described above to the pests or their environment.
  • the mixtures comprising a compound of Formula (I) selected from Table X (above) and one or more active ingredients 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 ingredient components, such as a "tank-mix", and in a combined use of the single active ingredients 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 ingredients as described above is not essential for working the present invention.
  • compositions of the present invention may also be used in crop enhancement.
  • 'crop enhancement' means an improvement in plant vigour, an improvement in plant quality, improved tolerance to stress factors, and/or improved input use efficiency.
  • 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 include, but are not limited to, early and/or improved germination, improved emergence, the ability to 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, earlier flowering, longer panicles, early grain maturity, increased seed, fruit or pod size, increased pod or ear number, increased seed number per pod or ear, increased seed mass, enhanced seed filling, less dead basal leaves, delay of senescence, improved vitality of the plant, increased levels of amino acids in storage tissues and/or
  • 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 reception), improved quality of harvested material, e.g. seeds, fruits, leaves, vegetables (such improved quality may manifest as improved visual appearance of the harvested material), improved carbohydrate content (e.g.
  • a plant with improved quality may have an increase in any of the aforementioned traits or any combination or two or more of the aforementioned traits.
  • 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 of the method of the invention.
  • Such traits include, but are not limited to, an increased tolerance and/or resistance to abiotic 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 potential or a reduction in the water supply to plants), cold exposure, heat exposure, osmotic stress, UV stress, flooding, increased salinity (e.g. in the soil), increased mineral exposure, ozone exposure, high light exposure and/or limited availability of nutrients (e.g.
  • a plant with improved tolerance to stress factors may have an increase in any of the aforementioned traits or any combination or two or more of the aforementioned traits. In the case of drought and nutrient stress, such improved tolerances may be due to, for example, more efficient uptake, use or retention of water and nutrients.
  • an 'improved input use efficiency' means that the plants are able to grow more effectively using given levels of inputs compared to the grown of control plants which are grown under the same conditions in the absence of the method of the invention.
  • 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 have an improved use of any of the aforementioned inputs or any combination of two or more of the aforementioned inputs.
  • crop enhancements of the present invention include a decrease in plant height, or reduction in tillering, which are beneficial features in crops or conditions where it is desirable to have less biomass and fewer tillers.
  • any or all 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.
  • '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 result from (a) an increase in the amount produced by the plant per se or (b) an improved ability to harvest plant matter, (ii) an improvement in the composition of the harvested material (e.g.
  • Improved sugar acid ratios 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 over the yield of the same product of the plant produced under the same conditions, but without application of the present invention. According to the present 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 all of the 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.
  • land i.e. land which was previously unavailable or sub-optimal for cultivation
  • plants which show an increased ability to survive in drought conditions may be able to be cultivated in areas of sub-optimal rainfall, e.g. perhaps on the fringe of a desert or even the desert itself.
  • crop enhancements are made in the substantial absence of pressure from pests and/or diseases and/or abiotic stress.
  • improvements in plant vigour, stress tolerance, quality and/or yield are made in the substantial absence of pressure from pests and/or diseases.
  • pests and/or diseases may be controlled by a pesticidal treatment that is applied prior to, or at the same time as, the method of the present invention.
  • improvements in plant vigour, stress tolerance, quality and/or yield are made in the absence of pest and/or disease pressure.
  • improvements in plant vigour, quality and/or yield are made in the absence, or substantial absence, of abiotic stress.
  • compositions of the present invention may also be used in the field of protecting storage goods against attack of fungi.
  • the term "storage goods” is understood to denote natural substances of vegetable and/or animal origin and their processed forms, which have 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, leafs, 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.
  • timber whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture 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.
  • storage goods is understood to denote 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 citrus fruits and their processed forms.
  • “storage goods” is understood to denote wood.
  • a further aspect of the present invention is a method of protecting storage goods, which comprises applying to the storage goods a composition according to the invention.
  • composition of the present invention may also be used in the field of protecting technical material against attack of fungi.
  • the term "technical material” includes paper; carpets; constructions; cooling and heating systems; wall-boards; ventilation and air conditioning systems and the like; preferably “technical material” is understood to denote 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 adjuvants, such as carriers, solvents and surface-active substances.
  • the formulations can be in various physical forms, e.g.
  • 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 ingredient with the formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions.
  • the active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof.
  • the active ingredients can also be contained in microcapsules.
  • Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release).
  • Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight.
  • the active ingredients 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, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art.
  • very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.
  • 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, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2-dichloropropane, diethanolamine, p- diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, A/,A/-dimethylformamide, dimethyl sulfoxide, 1 ,4- dioxane, di
  • Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, 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.
  • Surface-active substances may be anionic, 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, 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 alkylnaphthalenesulfonat.es, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2- ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol est
  • 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 buffers, 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 mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives.
  • 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.
  • 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 mineral 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 derivatives, or an oil of animal origin, such as fish oil or beef tallow.
  • Preferred oil additives comprise alkyl esters of C8-C22 fatty acids, especially the methyl derivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively).
  • Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10 th 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 concentrates, the end user will normally employ dilute formulations.
  • the rates of application vary within wide limits and depend 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.
  • a general guideline compounds may be applied at a rate of from 1 to 2000 l/ha, especially from 10 to 1000 l/ha.
  • compositions comprising a compound of Formula (I) described above may show a synergistic effect. This occurs whenever the action of an active ingredient combination is greater than the sum of the actions of the individual components.
  • the action to be expected E for a given active ingredient 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):
  • synergism corresponds to a positive value for the difference of (O-E).
  • expected activity said difference (O-E) is zero.
  • a negative value of said difference (O-E) signals a loss of activity compared to the expected activity.
  • composition according to the invention may also have further surprising advantageous properties.
  • advantageous properties 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, tillering 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.
  • 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.
  • composition according to the invention may be applied before or after infection of the 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 depend 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 therapeutic; the type of fungi to be controlled or the application time.
  • component (A) When applied to the useful plants component (A) is typically applied at a rate of 5 to 2000 g a.i./ha, particularly 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).
  • the application rates of the composition according to the invention depend on the type of effect desired, and typically range from 20 to 4000 g of total composition per hectare.
  • composition according to the invention 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, preferably from 0.01 to 10g per kg of seed, and 0.001 to 50 g of a compound of component (B), per kg of seed, preferably from 0.01 to 10g per kg of seed, are generally sufficient.
  • the compounds of the invention can be distinguished from known compounds by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.
  • Type of column Waters ACQUITY UPLC HSS T3; Column length: 30 mm; Internal diameter of column: 2.1 mm; Particle Size: 1 .8 micron; Temperature: 60°C.
  • enantiomerically pure final compounds may be obtained from racemic materials as appropriate via standard physical separation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, e.g., by using chiral starting materials.
  • active ingredients [components (A) and (B)] 25 % 50 % 75 %
  • the active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
  • active ingredients [components (A) and (B)] 25 % 50 % 75 %
  • the active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
  • 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 ingredients [components (A) and (B)] 5 % 6 % 4 % talcum 95 %
  • Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
  • Kaolin 82 % The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.
  • polyethylene glycol (mol. wt. 200) 3 %
  • Kaolin 89 % The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
  • nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %
  • silicone oil (in the form of a 75 % emulsion in water) 1 %
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion. Flowable concentrate for seed treatment
  • Silicone oil (in the form of a 75 % emulsion in water) 0.2 %
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • the obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent.
  • the capsule suspension formulation contains 28% of the active ingredients.
  • the medium capsule diameter is 8-15 microns.
  • the resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.
  • AIBN azobisisobutyronitrile
  • BOP-CI phosphoric acid bis(2-oxooxazolidide) chloride
  • CDI carbonyl diimidazole
  • DIPEA N,N-diisopropylethylamine
  • HATU 1-[bis(dimethylamino)methylene]-1 H-1 ,2,3-triazolo[4,5-b]pyridinium 3-oxid- hexafluorophosphate
  • NBS A/-bromosuccinimide
  • Timorex GoldTM active ingredient tea tree (Melaleuca alternifolia) oil
  • Stockton Group http://www.stockt.on- ag.com/products/timorex-gold/).
  • Example 1 This example illustrates the preparation of 2-(difluoromethoxy)-N-[[4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide (Compound X.12 of Table T1 )
  • Step 2 Preparation of 3-(p-tolyl)-5-(trifluoromethyl)-1 ,2,4-oxadiazole
  • Step 3a Preparation of 3-[4-(bromomethyl)phenyll-5-(trifluoromethyl)-1 ,2,4-oxadiazole
  • Step 3b Preparation of 3-[4-(bromomethyl)phenyll-5-(trifluoromethyl)-1 ,2,4-oxadiazole from 3-[4-
  • the resultant white slurry was extracted with dichloromethane and the total combined organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure.
  • the resultant crude was purified by flash chromatography over silica gel (cyclohexane/EtOAc eluent gradient 99: 1 to 9: 1 ) to afford 7.10 g of the title compound as a white solid, mp: 58-63°C.
  • Step 4 Preparation of [4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yllphenyllmethanamine hydrochloride
  • Step 5 Preparation of 2-hvdroxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yllphenyllmethyll acetamide
  • Step 6 Preparation of 2-(difluoromethoxy)-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yll phenyllmethyllacetamide 2-hydroxy-N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide (418 mg,
  • Example 2 This example illustrates the preparation of 1-methyl-3-[[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl]methyl]urea (Compound X.14 of Table T1 )
  • Example 3 This example illustrates the preparation of the intermediate [2,3-difluoro-4-[5- (trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methanamine
  • Example 4 This example illustrates the preparation of N-[[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide Compound X.01 of Table T1 )
  • Protocol A Portions of triphosgene (6 mg) in DCE (0.3 mL) were transferred at 0°C to a 96 slot deep well plate (DWP96) containing compounds of Formula (IV) (0.05 mmol), wherein Z-Nu is an amine derivative [HNR 5 R 6 , and triethylamine (0.12 mmol) in 200 [it DMA. The reaction mixtures were stirred at room temperature for 30 minutes. [4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]aryl]methanamine derivatives of Formula (II) (0.05 mmol) and triethylamine (0.12 mmol) in 200 ⁇ _ DMA were then added.
  • DWP96 96 slot deep well plate
  • Protocol B The amine derivative [HNR 5 R 6 ] of Formula (IV) (0.05 mmol) and DIPEA (0.25 mmol) in 300 ⁇ _ DMA were transferred at room temperature to a 96 slot deep well plate (DWP96). CDI (0.10 mmol) in DMA (300 ⁇ _) was added and the contents stirred until solubilization. [4-[5-(trifluoromethyl)- 1 ,2,4-oxadiazol-3-yl]aryl]methanamine derivatives of Formula (II) (0.05 mmol) and triethylamine (0.12 mmol) in 200 ⁇ _ DMA were then added. The DWP was sealed and stirred at room temperature for 18 hours.
  • enantiomerically pure final compounds may be obtained from racemic materials as appropriate via standard physical separation techniques, such as reverse phase chiral chromatography, or through stereoselective synthetic techniques, (e.g., by using chiral starting materials).
  • Table T1 Melting point (mp) data and/or retention times (Rt) for compounds X.01 to X.018 according to Formula (I):
  • Leaf disks or leaf segments of various plant species are cut from plants grown in a greenhouse.
  • the cut leaf disks or segments are placed in multiwell plates (24-well format) onto water agar.
  • the leaf disks are sprayed with a test solution before (preventative) or after (curative) inoculation.
  • Compounds to be tested are prepared as DMSO solutions (max. 10 mg/mL) which are diluted to the appropriate concentration with 0.025% Tween20 just before spraying.
  • the inoculated leaf disks or segments are incubated under defined conditions (temperature, relative humidity, light, etc.) according to the respective test system.
  • a single evaluation of disease level is carried out 3 to 14 days after inoculation, depending on the pathosystem. Percent disease control relative to the untreated check leaf disks or segments is then calculated.
  • General examples of liquid culture tests in well plates :
  • Mycelia fragments or conidia suspensions of a fungus prepared either freshly from liquid cultures of the fungus or from cryogenic storage, are directly mixed into nutrient broth.
  • DMSO solutions of the test compound (max. 10 mg/mL) are diluted with 0.025% Tween20 by a factor of 50 and 10 ⁇ _ of this solution is pipetted into a microtiter plate (96-well format).
  • the nutrient broth containing the fungal spores/mycelia fragments is then added to give an end concentration of the tested compound.
  • the test plates are incubated in the dark at 24°C and 96% relative humidity. The inhibition of fungal growth is determined photometrically after 2 to 7 days, depending on the pathosystem, and percent antifungal activity relative to the untreated check is calculated.
  • Example A1 Fungicidal activity against Puccinia recondita f. sp. tritici I wheat / leaf disc preventative (Brown rust) Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks were inoculated with a spore suspension of the fungus 1 day after application.
  • the inoculated leaf segments were incubated at 19 C and 75% relative humidity (rh) under a light regime of 12 hours light / 12 hours darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (7 to 9 days after application).
  • the following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.
  • Example A2 Fungicidal activity against Puccinia recondita f. sp. tritici I wheat / leaf disc curative (Brown rust)
  • Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates (24-well format). The leaf segments are then inoculated with a spore suspension of the fungus. Plates were stored in darkness at 19°C and 75% relative humidity. The formulated test compound diluted in water was applied 1 day after inoculation. The leaf segments were incubated at 19°C and 75% relative humidity under a light regime of 12 hours light / 12 hours darkness in a climate cabinet and the activity of a compound was assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf segments (6 to 8 days after application).
  • the following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.
  • Compounds (from Table T1 ) X.01 , X.02, X.03, X.04, X.05, X.06, X.07, X.08, X.09, X.10, X.1 1 , X.12, X.13, X.14, X.15, X.16, X.17 and X.18.
  • Example A3 Fungicidal activity against Phakopsora pachyrhizi I soybean / leaf disc preventative
  • Soybean leaf disks are placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water.
  • leaf discs are inoculated by spraying a spore suspension on the lower leaf surface.
  • the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears in untreated check leaf disks (12 to 14 days after application).
  • the following compounds at 200 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control leaf disks under the same conditions, which show extensive disease development.
  • Example A4 Fungicidal activity against Glomerella lagenarium (Colletotrichum lagenarium) liguid culture / cucumber / preventative (Anthracnose)
  • Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (PDB - potato dextrose broth). After placing a (DMSO) solution of test compound into a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 C and the inhibition of growth is measured photometrically 3 to 4 days after application.
  • nutrient broth PDB - potato dextrose broth
  • the following compounds at 20 ppm in the applied formulation give at least 80% disease control in this test when compared to untreated control under the same conditions, which show extensive disease development.
  • Soybean leaf disks are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed approx.12 dpi (days after inoculation) as preventive fungicidal activity.
  • the following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 80% disease control in this test.
  • Example B2 Glomerella lagenarium (Colletotrichum lagenarium) I cucumber / preventive -> COLLCUM/fo-pr-S Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24°C and the inhibition of growth was determined photometrically after 72 hrs at 620nm
  • Example B3 Puccinia recondita / wheat / preventive (Brown rust on wheat) -> PUCCTRZ/fo-pr-P + PUCCTRZ/fo-pr-S Wheat leaf segments are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with a spore suspension of the fungus. After appropriate incubation the activity of a compound is assessed 8 dpi (days after inoculation) as preventive fungicidal activity.

Abstract

L'invention concerne une composition fongicide comprenant un mélange de constituants (A) et (B), les constituants (A) et (B) étant tels que définis dans la revendication 1, ainsi que l'utilisation de ces compositions en agriculture ou en horticulture pour lutter contre ou empêcher l'infestation de plantes par des micro-organismes phytopathogènes, de préférence des champignons.
PCT/EP2018/057295 2017-03-31 2018-03-22 Compositions fongicides WO2018177880A1 (fr)

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WO2020209220A1 (fr) * 2019-04-09 2020-10-15 Sumitomo Chemical Company, Limited Procédé de protection d'un soja déterminé contre les dommages causés par un pathogène végétal
WO2021251274A1 (fr) * 2020-06-08 2021-12-16 日本曹達株式会社 Procédé de réduction ou de prévention de l'effet de stress non biologique sur une plante
CN114302646A (zh) * 2019-06-15 2022-04-08 Jdm科学研究组织私人有限公司 协同杀菌组合物
WO2022117650A1 (fr) 2020-12-02 2022-06-09 Syngenta Crop Protection Ag Compositions fongicides
WO2022117653A1 (fr) 2020-12-02 2022-06-09 Syngenta Crop Protection Ag Compositions fongicides
EP4091451A1 (fr) 2021-05-17 2022-11-23 BASF Agro B.V. Compositions comprenant du méfentrifluconazole
EP4094579A1 (fr) 2021-05-28 2022-11-30 Basf Se Mélanges de pesticides comprenant le métyltétraprole
WO2024068655A1 (fr) 2022-09-28 2024-04-04 Syngenta Crop Protection Ag Compositions fongicides
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