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WO2024068655A1 - Compositions fongicides - Google Patents

Compositions fongicides Download PDF

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Publication number
WO2024068655A1
WO2024068655A1 PCT/EP2023/076582 EP2023076582W WO2024068655A1 WO 2024068655 A1 WO2024068655 A1 WO 2024068655A1 EP 2023076582 W EP2023076582 W EP 2023076582W WO 2024068655 A1 WO2024068655 A1 WO 2024068655A1
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WO
WIPO (PCT)
Prior art keywords
methyl
phenyl
trifluoromethyl
pyridyl
oxadiazol
Prior art date
Application number
PCT/EP2023/076582
Other languages
English (en)
Inventor
Matthias Weiss
Atul Mahajan
Indira SEN
Simon Williams
Valeria Grasso
Original Assignee
Syngenta Crop Protection Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Syngenta Crop Protection Ag filed Critical Syngenta Crop Protection Ag
Publication of WO2024068655A1 publication Critical patent/WO2024068655A1/fr

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, 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
    • A01N43/86Biocides, 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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18Halogen atoms or nitro radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D279/00Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/041,3-Thiazines; Hydrogenated 1,3-thiazines
    • C07D279/081,3-Thiazines; Hydrogenated 1,3-thiazines condensed with carbocyclic rings or ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/101,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12Oxygen or sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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.
  • Wheat is a grass cultivated for its seed, a cereal grain which is a worldwide staple food.
  • Septoria tritici blotch is caused by the ascomycete fungus Mycosphaerella graminicola (asexual stage: Septoria tritici) and is one of the most important diseases of wheat - it is one of the most economically damaging diseases of this crop (being currently the most economically relevant disease in Europe).
  • Certain fungicidal quinoline compounds are described in WO 2009/119089 and WO 2022/207665.
  • compositions comprising mixtures of different fungicidal compounds possessing different modes of action can address some of these outstanding needs (eg, 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 1 is hydrogen or fluoro
  • R 2 is chloro, bromo, methyl or methoxy
  • R 3 is hydrogen, chloro or methyl; or R 2 is fluoro and R 3 is methyl. or a salt, tautomer and/or an N-oxide thereof, and component (B) is a compound selected from the group consisting of:
  • 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 :20, from 15:1 to 1 :15, from 12:1 to 1 :12, from 10:1 to 1 :10, from 5:1 and 1 :5, from 3:1 to 1 :3 or from 2:1 to 1 :2.
  • the phytopathogenic fungi is (i) Mycosphaerella graminicola, (ii) Monographella nivalis (Microdochium nivale), (iii) Gibberella zeae (anamorph: Fusarium graminearurri) or (iv) Fusarium culmorum.
  • the useful plant is cereals, in particular, wheat.
  • 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 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 a 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 1 is hydrogen or fluoro
  • R 2 is chloro or methyl
  • R 3 is hydrogen
  • R 2 is fluoro and R 3 is methyl.
  • component (A) is a compound selected from compound no. X.1 , X.2, X.3, X.4, X.5, X.6, X.7, X.8, X.9, X.10, X.11 or X.12 as defined in the Table X below. More preferably, component (A) is a compound selected from compound no. X.1 , X.2, X.3, X.4, and X.7 as defined in the Table X below. Table X
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin.
  • component (B) is a compound selected from the group consisting of florylpicoxamid, prothioconazole, fenpropidin, azoxystrobin, cyprodinil, folpet, pydiflumetofen.
  • component (B) is difenoconazole. In certain embodiments of the invention, component (B) is mefentrifluconazole.
  • component (B) is prothioconazole.
  • component (B) is metconazole.
  • component (B) is folpet.
  • component (B) is pydiflumetofen. In certain embodiments of the invention, component (B) is isoflucypram.
  • component (B) is benzovindiflupyr.
  • component (B) is fluxapyroxad. In certain embodiments of the invention, component (B) is metyltetraprole.
  • component (B) is azoxystrobin.
  • component (B) is cyprodinil.
  • component (B) is florylpicoxamid.
  • component (B) is fenpropidin.
  • 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.
  • intermediate compounds selected from:
  • Such compounds may be useful synthesis intermediates for the compounds of component (A) of the compositions of the present invention.
  • component (A) is compound no. X.1 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.
  • component (A) is compound no. X.2 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.
  • component (A) is compound no. X.3 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.
  • component (A) is compound no. X.4 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.
  • component (A) is compound no. X.5 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.
  • component (A) is compound no. X.6 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.
  • component (A) is compound no. X.7 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.
  • component (A) is compound no. X.8 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.
  • component (A) is compound no. X.9 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.
  • component (A) is compound no. X.10 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.
  • component (A) is compound no. X.11 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.
  • component (A) is compound no. X.12 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1 :30.
  • component (A) is compound no. X.1 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, 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 :5).
  • component (A) is compound no. X.2 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, 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 :5).
  • component (A) is compound no. X.3 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, 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 :5).
  • component (A) is compound no. X.4 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, 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 :5).
  • component (A) is compound no. X.5 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, 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 :5).
  • component (A) is compound no. X.6 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, 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 :5).
  • component (A) is compound no. X.7 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, 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 :5).
  • component (A) is compound no. X.8 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, 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 :5).
  • component (A) is compound no. X.9 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, 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 :5).
  • component (A) is compound no. X.10 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, 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 :5).
  • component (A) is compound no. X.11 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, 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 :5).
  • component (A) is compound no. X.12 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, 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 :5).
  • component (A) is compound no. X.1 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is 2:1 to 1 :2.
  • component (A) is compound no. X.2 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is 2:1 to 1 :2.
  • component (A) is compound no. X.3 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is 2:1 to 1 :2.
  • component (A) is compound no. X.4 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is 2:1 to 1 :2.
  • component (A) is compound no. X.5 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is 2:1 to 1 :2.
  • component (A) is compound no. X.6 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is 2:1 to 1 :2.
  • component (A) is compound no. X.7 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is 2:1 to 1 :2.
  • component (A) is compound no. X.8 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is 2:1 to 1 :2.
  • component (A) is compound no. X.9 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is 2:1 to 1 :2.
  • component (A) is compound no. X.10 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is 2:1 to 1 :2.
  • component (A) is compound no. X.1 1 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is 2:1 to 1 :2.
  • component (A) is compound no. X.12 or a salt, tautomer or N-oxide thereof
  • component (B) is a compound selected from the group consisting of difenoconazole, mefentrifluconazole, prothioconazole, metconazole, folpet, pydiflumetofen, isoflucypram, benzovindiflupyr, fluxapyroxad, metyltetraprole, azoxystrobin, cyprodinil, florylpicoxamid, fenpropidin, wherein the weight ratio of component (A) to component (B) is 2:1 to 1 :2.
  • 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.
  • 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 erythrose ptica; 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
  • 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, Cochliobolus sativus, Bipolaris cactivora, Venturia in
  • 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; as well as diseases caused by other species and genera closely related to those listed above.
  • the 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.
  • 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 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 beans
  • nuts for example almond
  • 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 RoundupReady®, 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 8-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 Mycosphaerella graminicola) on cereals, in particular, wheat.
  • 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 Mycosphaerella graminicola) on cereals (in particular wheat), may display a synergistic interaction between the active ingredients.
  • phytopathogenic diseases especially phytopathogenic fungi (such as Mycosphaerella graminicola) on cereals (in particular wheat)
  • cereals in particular wheat
  • Compounds of formula (I) can be prepared from thiophenols of formula (VII) by condensation with acetone or surrogates thereof such as acetals of formula (Villa), wherein R 21 is Ci-C4alkyl, in the presence of acid such as sulfuric acid and an optional dehydrating agent such as MgSC Closely related processes have been described in Tetrahedron 2001 , p.7501 -7506.
  • Thiophenols of formula (VII) can be prepared from thioethers of formula (VI), wherein R 22 is Ci-Ci2alkyl, benzyl or 2-trimethylsilylethyl, by treatment with a suitable deprotection agent as described in Greene's Protective Groups in Organic Synthesis, 4 th edition, Wiley&Sons 2006.
  • Thioethers of formula (VI), wherein R 22 is Ci-Ci2alkyl, benzyl or 2-trimethylsilylethyl can be prepared from ketones of formula (V), wherein R 22 is Ci-Ci2alkyl, benzyl or 2-trimethylsilylethyl, by treatment with an ammonia source such ammonia gas or bis(trimethylsilyl)amine in the presence of a Lewis acid such as zinc chloride or titanium ethoxide as described in ACIEE 2018, p. 5350-5354.
  • thioethers of formula (VI), wherein R 22 is Ci- Ci2alkyl, benzyl or 2-trimethylsilylethyl can be prepared from nitriles of formula (lllc), wherein R 22 is Ci- Ci2alkyl, benzyl or 2-trimethylsilylethyl, by treatment with an organometallic species generated from quinoline compounds of formula (II), wherein X is bromo or iodo, and a reagent such as magnesium turnings, isopropyl magnesium chloride or n-butyl lithium in an inert solvent such as THF.
  • Ketones of formula (V), wherein R 22 is Ci-Ci2alkyl, benzyl or 2-trimethylsilylethyl can be prepared from alcohols of formula (IV), wherein R 22 is Ci-Ci2alkyl, benzyl or 2-trimethylsilylethyl, by treatment with an oxidant such as MnC>2 in an inert solvent such as MeTHF.
  • ketones of formula (V), wherein R 22 is Ci- Ci2alkyl, benzyl or 2-trimethylsilylethyl can be prepared from carboxylic acid derivatives of formula (lllb), wherein R 22 is Ci-Ci2alkyl, benzyl or 2-trimethylsilylethyl and R 23 is N(CH3)OCH3, Ci-Cealkoxy, fluoro, chloro or imidazole, by treatment with an organometallic species generated from quinoline compounds of formula (II), wherein X is bromo or iodo, and a reagent such as magnesium turnings, zinc powder, isopropyl magnesium chloride or n-butyl lithium, an optional catalyst such as CuBr or bis(triphenylphosphine)nickel dichloride in an inert solvent such as THF.
  • Alcohols of formula (IV), wherein R 22 is Ci-Ci2alkyl, benzyl or 2-trimethylsilylethyl can be prepared from aldehydes of formula (Illa), wherein R 22 is Ci-Ci2alkyl, benzyl or 2-trimethylsilylethyl, by treatment with an organometallic species generated from quinoline compounds of formula (II), wherein X is bromo or iodo, and a reagent such as magnesium turnings, zinc powder, isopropyl magnesium chloride or n-butyl lithium, in an inert solvent such as THF.
  • Thioethers of formula (X-b) can be prepared from benzoic acids of formula (X-a) by treatment with lithium amides bases such as LDA or alkyl lithium bases such as sec-butyl lithium and a disulfide of formula (Xl-a), wherein R 22 is Ci-Ci2alkyl, benzyl or 2-trimethylsilylethyl, as described in J. Org. Chem. 2003, p.2030-2033.
  • Thioethers of formula (Illa), (X-b) and (X-c), wherein R 22 is Ci-Ci2alkyl, benzyl or 2- trimethylsilylethyl can be prepared from the corresponding halogenated compounds of formula (X-f), (X-e) and (X-d), wherein X is fluoro, chloro, bromo or iodo, and thiols of formula (Xl-b), wherein R 22 is Ci-Ci2alkyl, benzyl or 2-trimethylsilylethyl, in the presence of a base such as K2CO3 and an optional catalyst such as CU2O in an inert solvent as described in Synthesis 2007, p.3519-3527.
  • Thiophenols of formula (IX) can be prepared from benzamides of formula (X-d), where in X is fluoro, chloro, bromo or iodo, by treatment with a sulfide source such as sodium sulfide and an optional catalyst such as CU2O in an inert solvent such an N-methyl-2-pyrrolidone.
  • Scheme 2 :
  • Imines of formula (XIII), wherein R 25 is chloro, bromo, iodo or -OSO 2 CF 3 are prepared from compounds of formula (XIV) in the presence of a suitable activating agent such as Vilsmeier salt or triflic anhydride and an optional base such as 2,6-lutidine in an inert solvent such as DCM or toluene.
  • a suitable activating agent such as Vilsmeier salt or triflic anhydride
  • an optional base such as 2,6-lutidine in an inert solvent such as DCM or toluene.
  • Compounds of formula (XIV) are prepared from thiophenols of formula (IV) and acetone or surrogates thereof such as acetals of formula (Villa), wherein R 21 is Ci-C4alkyl, in the presence of an acidic catalyst such as p-toluene sulfonic acid, a dehydrating agent such as MgSC and optionally a nucleophilic amin catalyst such as pyrrolidine. This is shown in scheme 3.
  • Scheme 3 Alternatively, compounds of formula (I) can be obtained by transformation of another, closely related, compound of formula (I) (or analogue thereof) using standard synthesis techniques known to the person skilled in the art.
  • Non-exhaustive examples include oxidation reactions, oxygenation reactions, reduction reactions, hydrogenation reactions, hydrolysis reactions, coupling reactions, aromatic nucleophilic or electrophilic substitution reactions, nucleophilic substitution reactions, deoxyfluorination reactions, alkylation reactions, radical additions, nucleophilic addition reactions, condensation and halogenation reactions.
  • 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.
  • compositions of this invention may be formulated are:
  • suitable additional active ingredients also include the following: a compound selected from the group of substances consisting of petroleum oils, 1 ,1-bis(4-chlorophenyl)-2- ethoxyethanol, 2,4-dichlorophenyl benzenesulfonate, 2-fluoro-N-methyl-N-1 -naphthylacetamide, 4- chlorophenyl phenyl sulfone, acetoprole, aldoxycarb, amidithion, amidothioate, amiton, amiton hydrogen oxalate, amitraz, aramite, arsenous oxide, azobenzene, azothoate, benomyl, benoxafos, benzyl benzoate, bixafen, brofenvalerate, bromocyclen, bromophos, bromopropylate, buprofezin, butocarboxim, butoxycarboxim, butylpyridaben, calcium poly
  • Cryptolaemus montrouzieri Cydia pomonella GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formos a, Eretmocerus eremicus, Heterorhabditis bacteriophora and H. megidis,
  • Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus, Mamestra brassicae NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, Ne odiprion sertifer NPV and N.
  • lecontei NPV, Orius spp. Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steiner nema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema sp p., Trichogramma spp., Typhlodromus occidentalis, Verticillium lecanii, apholate, bisazir, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl apholate, morzid, penfluron, tepa, thiohempa, thiotepa, tretamine, uredepa, (E)-dec-5-en-1-yl
  • XMC zetamethrin, zinc phosphide, zolaprofos, and meperfluthrin, tetramethylfluthrin, bis(tributyltin) oxide, bromoacetamide, ferric phosphate, niclosamide-olamine, tributyltin oxide, pyrimorph, trifenmorph, 1 ,2-dibromo-3-chloropropane, 1 ,3-dichloropropene, 3,4- dichlorotetrahydrothiophene 1 ,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo- 1 ,3,5-thiadiazinan-3-ylacetic acid, 6-isopentenylaminopurine, 2-fluoro-N-(3-methoxyphenyl)-9H-purin- 6-amine, benclothiaz, cytokinins, DCIP, furf
  • the compounds of the invention may also be used in combination with anthelmintic agents.
  • anthelmintic agents include, compounds selected from the macrocyclic lactone class of compounds such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives as described in EP- 357460, EP- 444964 and EP-594291 .
  • Additional anthelmintic agents include semisynthetic and biosynthetic avermectin/milbemycin derivatives such as those described in US-5015630, WO-9415944 and WO- 9522552. Additional anthelmintic agents include the benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include flukicides, such as triclabendazole and clorsulon and the cestocides, such as praziquantel and epsiprantel.
  • the compounds of the invention may be used in combination with derivatives and analogues of the paraherquamide/marcfortine class of anthelmintic agents, as well as the antiparasitic oxazolines such as those disclosed in US-5478855, US- 4639771 and DE-19520936.
  • the compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO 96/15121 and also with anthelmintic active cyclic depsipeptides such as those described in WO 96/1 1945, WO 93/19053, WO 93/25543, EP 0 626 375, EP 0 382 173, WO 94/19334, EP 0 382 173, and EP 0 503 538.
  • the compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.
  • ectoparasiticides for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide and the like; neonicotinoids such as imidacloprid and the like.
  • the compounds of the invention may be used in combination with terpene alkaloids, for example those described in International Patent Application Publication Numbers WO 95/19363 or WO 04/72086, particularly the compounds disclosed therein.
  • Organophosphates acephate, azamethiphos, azinphos-ethyl, azinphos- methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, me
  • Carbamates alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801 , isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.
  • Pyrethroids acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl (E)-(1 R)-cis-2,2-dimethyl- 3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, a- cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, ethofenprox, fenfluthrin, fenpropathrin, fenvaler
  • Arthropod growth regulators a) chitin synthesis inhibitors: benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole, chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) juvenoids: pyriproxyfen, methoprene (including S-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors: spirodiclofen.
  • antiparasitics acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloden, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, ethofenprox, fenazaquin, flumite, MTI- 800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox, fluproxyfen, halofenprox, hydr
  • Biological agents Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, virus and fungi.
  • Bactericides chlortetracycline, oxytetracycline, streptomycin.
  • 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.1 , X.2, X.3, X.4, X.5, X.6, X.7, X.8, X.9, X.10, X.11 or X.12 as defined in the Table X above: a compound selected from the group of substances consisting of petroleum oils + TX, 1 , 1 -bis(4- chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenyl benzenesulfonate + TX, 2-fluoro-N-methyl-N- 1 -naphthylacetamide + TX, 4-chlorophenyl phenyl sulfone + TX, acetoprole + TX, aldoxycarb + TX, amidithion + TX, amid
  • TX Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema feltiae + TX, Steinernema glaseri + TX, Steinernema riobrave + TX, Steinernema riobravis + TX, Steinernema scapterisci + TX, Steinernema spp. + TX, Trichogramma spp.
  • TX (these compounds may be prepared from the methods described in WO2019/110427); N-[(1 R)-1- benzyl-3-chloro-1 -methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1 S)-1 -benzyl-3- chloro-1 -methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1 R)-1 -benzyl-3,3,3-trifluoro-1 - methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1 S)-1 -benzyl-3,3,3-trifluoro-1 -methyl- propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1 R)-1-benzyl-1 ,3-dimethyl-butyl]-7,8-difluoro- quinoline-3-carboxamide +
  • the compounds in this paragraph may be prepared from the methods described in WO 2017/055473, WO 2017/055469, WO 2017/093348 and WO 2017/118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol + TX (this compound may be prepared from the methods described in WO 2017/029179); 2-[6-(4- bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1-yl)propan-2-ol + TX (this compound may be prepared from the methods described in WO 2017/029179); 3-[2-(1-chlorocyclopropyl)-3-(2- fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + TX (this compound may be prepared from the methods described in WO 2016
  • 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 :100, especially from 50:1 to 1 :50, more especially in a ratio of from 20:1 to 1 :20, even more especially from 10:1 to 1 :10, 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 :2,
  • 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 less
  • 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.
  • 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.
  • 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. in the form of dusting powders, gels, wettable powders, water- dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, micro- emulsifiable concentrates, oil-in-water emulsions, oil-flowables, aqueous dispersions, oily dispersions, suspo-emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water-miscible organic solvent as carrier), impregnated polymer films or in other forms known 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, /V,/V-dimethylformamide, dimethyl sulfoxide, 1 ,4- dioxane,
  • 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 alkylnaphthalenesulfonates, 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 esters of
  • 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.
  • a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance.
  • 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.
  • 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.
  • 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.
  • compositions 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 (and compositions) of the invention may be distinguished from known compounds (and compositions) by virtue of greater efficacy at low application rates, which can be verified by the person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.2 ppm of active ingredients).
  • Compounds (and compositions) may possess any number of benefits including, 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 (including improved crop tolerance), improved physico-chemical properties, or increased biodegradability).
  • 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 (including improved crop tolerance), improved physico-chemical properties, or increased biodegradability).
  • LC/MS Liquid Chromatography Mass Spectrometry and the description of the apparatus and the method is as follows:
  • Spectra were recorded on a Mass Spectrometer from Waters (SQD, SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and negative ions), Capillary: 3.00 kV, Cone range: 30 V, Extractor: 2.00 V, Source Temperature: 150 °C, Desolvation Temperature: 350 °C, Cone Gas Flow: 50 l/h, Desolvation Gas Flow: 650 l/h, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment , diode-array detector and ELSD detector.
  • Spectra were recorded on a Mass Spectrometer from Waters (SQD, SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive and negative ions), Capillary: 0.8 kV, Cone range: 25 V, Source Temperature: 120°C, Desolvation Temperature: 600°C, Cone Gas Flow: 50 l/h, Desolvation Gas Flow: 1000 l/h, Mass range: 110 to 850 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment , diode-array detector and ELSD detector.
  • Wettable powders a) b) c) active ingredients [components (A) and (B)] 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate 6 % 10 % phenol polyethylene glycol ether 2 % (7-8 mol of ethylene oxide) highly dispersed silicic acid 5 % 10 % 10 %
  • 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 waterto give suspensions of the desired concentration.
  • Powders for dry seed treatment a) b) c) active ingredients [components (A) and (B)] 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 %
  • Talcum 20 % 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.
  • Emulsifiable concentrate active ingredients [components (A) and (B)] 10 % octylphenol polyethylene glycol ether 3 %
  • 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.
  • Extruder granules active ingredients [components (A) and (B)] 15 % sodium lignosulfonate 2 % carboxymethylcellulose 1 %
  • 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.
  • Coated granules active ingredients [components (A) and (B)] 8 % polyethylene glycol (mol. wt. 200) 3 %
  • 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.
  • Suspension concentrate active ingredients [components (A) and (B)] 40 % propylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %
  • 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.
  • Flowable concentrate for seed treatment active ingredients [components (A) and (B)] 40 % propylene glycol 5 % copolymer butanol PO/EO 2 % tristyrenephenole with 10-20 moles EO 2 %
  • Silicone oil (in the form of a 75 % emulsion in water) 0.2 % Water 45.3 %
  • 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.
  • 4-carboxylate may be prepared according to the methods described in WO 2017/055469, WO 2017/055473, WO 2017/093348, WO 2017/118689, WO 2017/220485, WO 2018/065414, WO 2018/158365, WO 2018/177894, WO 2018/177880, WO 2018/219773 and WO 2019/002151 .
  • the compound methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1 ,2,4-triazol-1- ylmethyl)cyclopentanecarboxylate may be prepared according to the methods described in WO 2012/169516.
  • the compound 4-[[6-[2-(2,4-difluorophenyl)-1 ,1-difluoro-2-hydroxy-3-(tetrazol-1- yl)propyl]-3-pyridyl]oxy]benzonitrile may be prepared according to the methods described in WO 2012/177638.
  • the compound methyl 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-hydroxy-3- (1 ,2,4-triazol-1-yl)propanoate may be prepared according to the methods described in WO 2019/093522.
  • DIBAL diisobutyl aluminium hydride
  • PdCI 2 (dtbpf) [1 ,T-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(ll)
  • CataxiumA Pd G3 [(Di(1-adamantyl)-butylphosphine)-2-(2'-amino-1 ,1 '-biphenyl)]palladium(ll) methanesulfonate
  • PdCl2(dppf)-DCM [1 ,1 '-Bis(diphenylphosphino)ferrocene]dichloropalladium(ll), complex with dichloromethane
  • Pd XPhos G2 Chloro(2-dicyclohexylphosphino-2',4',6'-tri-i-propyl-1 ,1 '-biphenyl)(2'-amino-
  • LC/MS Liquid Chromatography Mass Spectrometry (description of the apparatus and the methods used for LC/MS analysis are given above)
  • Example B1 8-chloro-4-(8-fluoro-3-quinolyl)-2,2-dimethyl-1 ,3-benzothiazine (compound X.1)
  • Step 1
  • reaction mixture was stirred for 2h at -30°C and then a solution of 2-tert-butylsulfanyl-3-chloro- benzaldehyde (5.0 g, 22 mmol) in toluene (20 mL) was added drop wise.
  • the temperature of the reaction mixture was gradually raised to 0°C over 2h and then the reaction was quenched by addition of icewater.
  • the resulting suspension was neutralized with aq. HCI and extracted with EtOAc. The organic layer was washed with water, dried over MgSO4, filtrated and concentrated in vacuo.
  • Step 1
  • a solution of sodium sulfide (2.49 g, 31 .6 mmol) in 1-methyl-2-pyrrolidine (150 mL) was aged for 2 h at 190° C under a gentle stream of nitrogen.
  • the resulting solution was cooled to 130 °C, 2,3- dichlorobenzamide (5.0 g, 26.3 mmol) was added, the mixture was warmed to 175 °C and aged for 4 h at this temperature.
  • the mixture was then cooled to 70 °C and MgSO4 (3.23 g, 26.3 mmol), p-toluene sulfonic acid (5.50 g, 28.9 mmol) and 2,2-dimethoxypropane ( 17 mL, 131 mmol) was added.
  • Example B3 4-(8-fluoro-3-quinolyl)-2,2,8-trimethyl-1 ,3-benzothiazine (compound X.3)
  • Step 1
  • Example B4 8-fluoro-4-(8-fluoro-3-quinolyl)-2, 2, 7-trimethyl-1 ,3-benzothiazine (compound X.7) step 1 :
  • Example B5 8-chloro-4-(8-fluoro-3-quinolyl)-2, 2, 7-trimethyl-1 ,3-benzothiazine (compound X.5)
  • Step 1 A solution of 3-chloro-4-methyl benzoic acid (3.0 g, 17.6 mmol) in dry THF (90 mL) under Ar at - 70°C was treated with nBuLi (2.5M in hexanes, 21 mL, 52.8 mmol) and the resulting yellow solution was aged for 2h at -70°C. Dimethyldisulfide (3.15 mL, 35.2 mmol) was then added and the reaction was gradually warmed to RT over 2.5h. The reaction mixture was diluted with TBME and extracted with water. The aqueous layer was acidified with 2M HCI and extracted with TBME.
  • Example B6 4-(8-fluoro-3-quinolyl)-2,2,7,8-tetramethyl-1 ,3-benzothiazine (compound X.9)
  • Step 1
  • DMSO DMSO
  • 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 3-4 days after application. The following compounds gave at least 80% control of Colletotrichum lagenarium at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development:
  • 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 determined photometrically 3-4 days after application.
  • nutrient broth PDB potato dextrose broth
  • Wheat spikelets cv. Monsun are placed on agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water.
  • the spikelets are inoculated with a spore suspension of the fungus.
  • the inoculated test leaf disks are incubated at 20 °C and 60% rh under a light regime of 72 h semi darkness followed by 12 h light / 12 h darkness in a climate chamber, the activity of a compound is assessed as percent disease control compared to untreated when an appropriate level of disease damage appears on untreated check spikelets (6 - 8 days after application).
  • 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 determined photometrically 4-5 days after application.
  • nutrient broth PDB potato dextrose broth
  • Rice leaf segments cv. Ballila are placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water.
  • the leaf segments are inoculated with a spore suspension of the fungus 2 days after application.
  • the inoculated leaf segments are incubated at 22 °C and 80% rh under a light regime of 24 h darkness followed by 12 h light / 12 h darkness in a climate cabinet and 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 segments (5 - 7 days after application).
  • Conidia of the fungus from cryogenic storage are directly mixed into nutrient broth (Vogel’s medium). 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 determined photometrically 4-5 days after application.
  • DMSO fetal sulfate
  • Mycosphaerella graminicola (Septoria tritici) on wheat / preventative
  • 2-week old wheat plants cv. Riband are sprayed in a spray chamber with formulated test compound diluted in water.
  • the test plants are inoculated by spraying a spore suspension on them one day after spray application and then kept at 22°C/21 °C (day/night) in a greenhouse. Disease damage is assessed directly when an appropriate level of disease appears on untreated check plants and efficacy was calculated compare to untreated controls (16 to 19 days after application).
  • Mycosphaerella graminicola (Septoria tritici) on wheat / preventative
  • 2-week old wheat plants cv. Riband are sprayed in a spray chamber with the test compound formulated as emulsifiable concentrate diluted in water.
  • the test plants are inoculated by spraying a spore suspension on them one day after application and then kept at 22°C/21 °C (day/night) in a greenhouse.
  • Disease damage is assessed directly when an appropriate level of disease appears on untreated check plants and efficacy was calculated compared to untreated controls (16 to 19 days after application).
  • test plants cv. Wisconsin 1-week old cucumber plants cv. Wisconsin are sprayed in a spray chamber with the test compound formulated as emulsifible concentrate diluted in water.
  • the test plants are inoculated by spraying them with a spore suspension one day after application. After an incubation period of 30 h in darkness at 23° C and 100% rh, the inoculated test plants are kept at 23° C / 21 ° C (day/night) and 70% rh in a greenhouse.
  • the percentage leaf area covered by disease is assessed when an appropriate level of disease appears on untreated check plants (6 - 8 days after application).
  • the compounds according to this invention display excellent control of Mycosphaerella graminicola (Septoria tritici) without compromising the spectrum of other diseases controlled by the compounds of the prior art.
  • Example A1 In vitro activity against Septoria tritici (leaf blotch):
  • Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (Vogel’s medium).
  • 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.
  • Example A2 In vitro activity against Fusarium culmorum (root rot): 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 48 hrs. The following mixture compositions (A:B) at the reported concentration (in ppm) gave at least
  • Example A3 In vitro activity against Monographella nivalis syn. Microdochium nivale, Fusarium nivale (snow mould, foot rot of cereals):
  • 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.
  • the following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 80% disease control in this test.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne une composition fongicide comprenant un mélange de composants (A) et (B), les composants (A) et (B) étant tels que définis dans la revendication 1, et l'utilisation des compositions en agriculture ou en horticulture pour lutter contre des micro-organismes phytopathogènes, de préférence des champignons, ou prévenir l'infestation de plantes par ceux-ci.
PCT/EP2023/076582 2022-09-28 2023-09-26 Compositions fongicides WO2024068655A1 (fr)

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Citations (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4639771A (en) 1984-10-31 1987-01-27 Kabushiki Kaisha Toshiba Image processing system
EP0382173A2 (fr) 1989-02-07 1990-08-16 Meiji Seika Kaisha Ltd. Substance PF 1022, procédé pour sa préparation et composition anthelmintique contenant cette substance
US5015630A (en) 1989-01-19 1991-05-14 Merck & Co., Inc. 5-oxime avermectin derivatives
EP0503538A1 (fr) 1991-03-08 1992-09-16 Meiji Seika Kaisha Ltd. Composition médicale contenant un dépepsipeptide cyclique ayant une activité anthelminthique
WO1993019053A1 (fr) 1992-03-17 1993-09-30 Fujisawa Pharmaceutical Co., Ltd. Derive de depsipeptide, production et utilisation
WO1993025543A2 (fr) 1992-06-11 1993-12-23 Bayer Aktiengesellschaft Enniatines et derives d'enniatines utilises dans la lutte contre les endoparasites
WO1994015944A1 (fr) 1993-01-18 1994-07-21 Pfizer Limited Nouveaux agents antiparasitaires apparentes aux milbemycines et aux avermectines
WO1994019334A1 (fr) 1993-02-19 1994-09-01 Meiji Seika Kaisha, Ltd. Derive du pf 1022 utilise comme depsipeptide cyclqiue
EP0626375A1 (fr) 1993-05-26 1994-11-30 Bayer Ag Octacyclodepsipeptides ayant une activité endoparasiticide
WO1995019363A1 (fr) 1994-01-14 1995-07-20 Pfizer Inc. COMPOSéS ANTIPARASITAIRES A BASE DE PYRROLOBENZOXAZINE
WO1995022552A1 (fr) 1994-02-16 1995-08-24 Pfizer Limited Agents antiparasitaires
US5478855A (en) 1992-04-28 1995-12-26 Yashima Chemical Industry Co., Ltd. 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline
WO1996011945A2 (fr) 1994-10-18 1996-04-25 Bayer Aktiengesellschaft Procede de sulfonylation, de sulfenylation et de phosphorylation de depsipeptides cycliques
WO1996015121A1 (fr) 1994-11-10 1996-05-23 Bayer Aktiengesellschaft Utilisation de dioxomorpholines pour lutter contre les endoparasites, nouvelles dioxomorpholines et leur procede de production
DE19520936A1 (de) 1995-06-08 1996-12-12 Bayer Ag Ektoparasitizide Mittel
WO2004072086A2 (fr) 2003-02-14 2004-08-26 Pfizer Limited Terpene alcaloides antiparasitiques
WO2009119089A1 (fr) 2008-03-27 2009-10-01 日本曹達株式会社 Composé hétérocyclique contenant de l’azote et bactéricide pour utilisation agricole et horticole
JP2011148714A (ja) * 2010-01-19 2011-08-04 Nippon Soda Co Ltd 病害防除方法
WO2011138281A2 (fr) 2010-05-06 2011-11-10 Bayer Cropscience Ag Procédé de production de dithiine-tétracarboxy-diimides
WO2012169516A1 (fr) 2011-06-07 2012-12-13 株式会社クレハ Dérivé azole, son procédé de fabrication, composé intermédiaire et agent chimique agricole ou horticole et agent de protection de matière industrielle
WO2012177638A1 (fr) 2011-06-19 2012-12-27 Viamet Pharmaceuticals, Inc. Composés inhibiteurs de métalloenzymes
WO2014006945A1 (fr) 2012-07-04 2014-01-09 アグロカネショウ株式会社 Dérivé d'ester d'acide 2-aminonicotinique et bactéricide le contenant comme principe actif
WO2014095675A1 (fr) 2012-12-19 2014-06-26 Bayer Cropscience Ag Utilisation de carboxamides difluorométhyl-nicotinique-indanyle comme fongicides
WO2015155075A1 (fr) 2014-04-11 2015-10-15 Syngenta Participations Ag Dérivés fongicide de n'- [2-méthyl -6- [2-alcoxy-éthoxy]-3-pyridyl]-n-alkyl-formamidine destinés à être utilisés dans l'agriculture
WO2016156085A1 (fr) 2015-03-27 2016-10-06 Syngenta Participations Ag Dérivés hétérobicycliques microbiocides
WO2016156290A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5
WO2016202742A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
WO2017025510A1 (fr) 2015-08-12 2017-02-16 Syngenta Participations Ag Dérivés hétérobicycliques microbiocides
WO2017029179A1 (fr) 2015-08-14 2017-02-23 Bayer Cropscience Aktiengesellschaft Dérivés de triazole, leurs intermédiaires et leur utilisation comme fongicides
WO2017055473A1 (fr) 2015-10-02 2017-04-06 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017055469A1 (fr) 2015-10-02 2017-04-06 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017063973A1 (fr) 2015-10-14 2017-04-20 Syngenta Participations Ag Compositions fongicides
WO2017093348A1 (fr) 2015-12-02 2017-06-08 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017102635A1 (fr) 2015-12-15 2017-06-22 Syngenta Participations Ag Dérivés de phénylamidine microbiocides
WO2017118689A1 (fr) 2016-01-08 2017-07-13 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017153380A1 (fr) 2016-03-10 2017-09-14 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2017220485A1 (fr) 2016-06-21 2017-12-28 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2018065414A1 (fr) 2016-10-06 2018-04-12 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2018153707A1 (fr) 2017-02-22 2018-08-30 Basf Se Formes cristallines d'un composé de type strobilurine pour lutter contre des champignons phytopathogènes
WO2018158365A1 (fr) 2017-03-03 2018-09-07 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2018172133A1 (fr) 2017-03-20 2018-09-27 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2018177880A1 (fr) 2017-03-31 2018-10-04 Syngenta Participations Ag Compositions fongicides
WO2018177894A1 (fr) 2017-03-31 2018-10-04 Syngenta Participations Ag Compositions fongicides
WO2018202428A1 (fr) 2017-05-02 2018-11-08 Basf Se Mélange fongicide comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués
WO2018219773A1 (fr) 2017-06-02 2018-12-06 Syngenta Participations Ag Compositions fongicides
WO2018228896A1 (fr) 2017-06-14 2018-12-20 Syngenta Participations Ag Compositions fongicides
WO2019002151A1 (fr) 2017-06-28 2019-01-03 Syngenta Participations Ag Compositions fongicides
WO2019093522A1 (fr) 2017-11-13 2019-05-16 株式会社クレハ Dérivé d'azole, composé intermédiaire, procédé de production d'un dérivé d'azole, agent à usage agricole et horticole, et agent de protection de matériau à usage industriel
WO2019110427A1 (fr) 2017-12-04 2019-06-13 Syngenta Participations Ag Dérivés de phénylamidine microbiocides
WO2020079111A1 (fr) 2018-10-18 2020-04-23 Syngenta Crop Protection Ag Composés microbiocides
WO2020109509A1 (fr) 2018-11-30 2020-06-04 Syngenta Participations Ag Dérivés de thiazole microbiocides
WO2020109511A1 (fr) 2018-11-30 2020-06-04 Syngenta Crop Protection Ag Dérivés de 2-acylamino-thiazole-4-carboxamide microbiocides
WO2020165403A1 (fr) 2019-02-15 2020-08-20 Syngenta Crop Protection Ag Dérivés de thiazole substitués par phényle en tant que composés microbiocides
WO2020193387A1 (fr) 2019-03-22 2020-10-01 Syngenta Crop Protection Ag Composés fongicides
WO2022207665A1 (fr) 2021-03-31 2022-10-06 Syngenta Crop Protection Ag Dérivés de quinoline/quinoxaline benzothiazine microbiocides

Patent Citations (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4639771A (en) 1984-10-31 1987-01-27 Kabushiki Kaisha Toshiba Image processing system
US5015630A (en) 1989-01-19 1991-05-14 Merck & Co., Inc. 5-oxime avermectin derivatives
EP0382173A2 (fr) 1989-02-07 1990-08-16 Meiji Seika Kaisha Ltd. Substance PF 1022, procédé pour sa préparation et composition anthelmintique contenant cette substance
EP0503538A1 (fr) 1991-03-08 1992-09-16 Meiji Seika Kaisha Ltd. Composition médicale contenant un dépepsipeptide cyclique ayant une activité anthelminthique
WO1993019053A1 (fr) 1992-03-17 1993-09-30 Fujisawa Pharmaceutical Co., Ltd. Derive de depsipeptide, production et utilisation
US5478855A (en) 1992-04-28 1995-12-26 Yashima Chemical Industry Co., Ltd. 2-(2,6-difluorophenyl)-4-(2-ethoxy-4-tert-butylphenyl)-2-oxazoline
WO1993025543A2 (fr) 1992-06-11 1993-12-23 Bayer Aktiengesellschaft Enniatines et derives d'enniatines utilises dans la lutte contre les endoparasites
WO1994015944A1 (fr) 1993-01-18 1994-07-21 Pfizer Limited Nouveaux agents antiparasitaires apparentes aux milbemycines et aux avermectines
WO1994019334A1 (fr) 1993-02-19 1994-09-01 Meiji Seika Kaisha, Ltd. Derive du pf 1022 utilise comme depsipeptide cyclqiue
EP0626375A1 (fr) 1993-05-26 1994-11-30 Bayer Ag Octacyclodepsipeptides ayant une activité endoparasiticide
WO1995019363A1 (fr) 1994-01-14 1995-07-20 Pfizer Inc. COMPOSéS ANTIPARASITAIRES A BASE DE PYRROLOBENZOXAZINE
WO1995022552A1 (fr) 1994-02-16 1995-08-24 Pfizer Limited Agents antiparasitaires
WO1996011945A2 (fr) 1994-10-18 1996-04-25 Bayer Aktiengesellschaft Procede de sulfonylation, de sulfenylation et de phosphorylation de depsipeptides cycliques
WO1996015121A1 (fr) 1994-11-10 1996-05-23 Bayer Aktiengesellschaft Utilisation de dioxomorpholines pour lutter contre les endoparasites, nouvelles dioxomorpholines et leur procede de production
DE19520936A1 (de) 1995-06-08 1996-12-12 Bayer Ag Ektoparasitizide Mittel
WO2004072086A2 (fr) 2003-02-14 2004-08-26 Pfizer Limited Terpene alcaloides antiparasitiques
WO2009119089A1 (fr) 2008-03-27 2009-10-01 日本曹達株式会社 Composé hétérocyclique contenant de l’azote et bactéricide pour utilisation agricole et horticole
JP2011148714A (ja) * 2010-01-19 2011-08-04 Nippon Soda Co Ltd 病害防除方法
WO2011138281A2 (fr) 2010-05-06 2011-11-10 Bayer Cropscience Ag Procédé de production de dithiine-tétracarboxy-diimides
WO2012169516A1 (fr) 2011-06-07 2012-12-13 株式会社クレハ Dérivé azole, son procédé de fabrication, composé intermédiaire et agent chimique agricole ou horticole et agent de protection de matière industrielle
WO2012177638A1 (fr) 2011-06-19 2012-12-27 Viamet Pharmaceuticals, Inc. Composés inhibiteurs de métalloenzymes
WO2014006945A1 (fr) 2012-07-04 2014-01-09 アグロカネショウ株式会社 Dérivé d'ester d'acide 2-aminonicotinique et bactéricide le contenant comme principe actif
WO2014095675A1 (fr) 2012-12-19 2014-06-26 Bayer Cropscience Ag Utilisation de carboxamides difluorométhyl-nicotinique-indanyle comme fongicides
WO2015155075A1 (fr) 2014-04-11 2015-10-15 Syngenta Participations Ag Dérivés fongicide de n'- [2-méthyl -6- [2-alcoxy-éthoxy]-3-pyridyl]-n-alkyl-formamidine destinés à être utilisés dans l'agriculture
WO2016156085A1 (fr) 2015-03-27 2016-10-06 Syngenta Participations Ag Dérivés hétérobicycliques microbiocides
WO2016156290A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5
WO2016202742A1 (fr) 2015-06-15 2016-12-22 Bayer Cropscience Aktiengesellschaft Phénoxyphénylamidines à substitution halogène et utilisation de celles-ci en tant que fongicides
WO2017025510A1 (fr) 2015-08-12 2017-02-16 Syngenta Participations Ag Dérivés hétérobicycliques microbiocides
WO2017029179A1 (fr) 2015-08-14 2017-02-23 Bayer Cropscience Aktiengesellschaft Dérivés de triazole, leurs intermédiaires et leur utilisation comme fongicides
WO2017055473A1 (fr) 2015-10-02 2017-04-06 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017055469A1 (fr) 2015-10-02 2017-04-06 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017063973A1 (fr) 2015-10-14 2017-04-20 Syngenta Participations Ag Compositions fongicides
WO2017093348A1 (fr) 2015-12-02 2017-06-08 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017102635A1 (fr) 2015-12-15 2017-06-22 Syngenta Participations Ag Dérivés de phénylamidine microbiocides
WO2017118689A1 (fr) 2016-01-08 2017-07-13 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017153380A1 (fr) 2016-03-10 2017-09-14 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2017220485A1 (fr) 2016-06-21 2017-12-28 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2018065414A1 (fr) 2016-10-06 2018-04-12 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2018153707A1 (fr) 2017-02-22 2018-08-30 Basf Se Formes cristallines d'un composé de type strobilurine pour lutter contre des champignons phytopathogènes
WO2018158365A1 (fr) 2017-03-03 2018-09-07 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2018172133A1 (fr) 2017-03-20 2018-09-27 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
WO2018177880A1 (fr) 2017-03-31 2018-10-04 Syngenta Participations Ag Compositions fongicides
WO2018177894A1 (fr) 2017-03-31 2018-10-04 Syngenta Participations Ag Compositions fongicides
WO2018202428A1 (fr) 2017-05-02 2018-11-08 Basf Se Mélange fongicide comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués
WO2018219773A1 (fr) 2017-06-02 2018-12-06 Syngenta Participations Ag Compositions fongicides
WO2018228896A1 (fr) 2017-06-14 2018-12-20 Syngenta Participations Ag Compositions fongicides
WO2019002151A1 (fr) 2017-06-28 2019-01-03 Syngenta Participations Ag Compositions fongicides
WO2019093522A1 (fr) 2017-11-13 2019-05-16 株式会社クレハ Dérivé d'azole, composé intermédiaire, procédé de production d'un dérivé d'azole, agent à usage agricole et horticole, et agent de protection de matériau à usage industriel
WO2019110427A1 (fr) 2017-12-04 2019-06-13 Syngenta Participations Ag Dérivés de phénylamidine microbiocides
WO2020079111A1 (fr) 2018-10-18 2020-04-23 Syngenta Crop Protection Ag Composés microbiocides
WO2020109509A1 (fr) 2018-11-30 2020-06-04 Syngenta Participations Ag Dérivés de thiazole microbiocides
WO2020109511A1 (fr) 2018-11-30 2020-06-04 Syngenta Crop Protection Ag Dérivés de 2-acylamino-thiazole-4-carboxamide microbiocides
WO2020165403A1 (fr) 2019-02-15 2020-08-20 Syngenta Crop Protection Ag Dérivés de thiazole substitués par phényle en tant que composés microbiocides
WO2020193387A1 (fr) 2019-03-22 2020-10-01 Syngenta Crop Protection Ag Composés fongicides
WO2022207665A1 (fr) 2021-03-31 2022-10-06 Syngenta Crop Protection Ag Dérivés de quinoline/quinoxaline benzothiazine microbiocides

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
"Synthesis", 2006, WILEY&SONS
ACIEE, 2018, pages 5350 - 5354
COLBY, S.R.: "Calculating synergistic and antagonistic responses of herbicide combination", WEEDS, vol. 15, 1967, pages 20 - 22, XP001112961
J. ORG. CHEM., 2003, pages 2030 - 2033
MCCUTCHEON: "Detergents and Emulsifiers Annual", 1981, MC PUBLISHING CORP.
SYNTHESIS, 2007, pages 3519 - 3527
TETRAHEDRON, 2001, pages 7501 - 7506
TETRAHEDRON, 2017, pages 1618 - 1632

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