[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

WO2024213720A1 - Compositions fongicides - Google Patents

Compositions fongicides Download PDF

Info

Publication number
WO2024213720A1
WO2024213720A1 PCT/EP2024/060005 EP2024060005W WO2024213720A1 WO 2024213720 A1 WO2024213720 A1 WO 2024213720A1 EP 2024060005 W EP2024060005 W EP 2024060005W WO 2024213720 A1 WO2024213720 A1 WO 2024213720A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
fluoro
carboxamide
quinoline
benzyl
Prior art date
Application number
PCT/EP2024/060005
Other languages
English (en)
Inventor
Stephane André Marie JEANMART
Mathias Blum
Alexandre Franco Jean Camille LUMBROSO
Nicolas Germain
Martin Pouliot
Camille LE CHAPELAIN
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 WO2024213720A1 publication Critical patent/WO2024213720A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides

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 more particularly oomycetes, and to methods of controlling diseases on useful plants.
  • many fungicidal compounds and compositions, belonging to various different chemical classes, have been/are being developed for use as fungicides in crops of useful plants, crop tolerance and activity against particular phytopathogenic fungi do not always satisfy the needs of agricultural practice in many respects. Therefore, there is a continuing need to find new compounds and compositions having superior biological properties for use in controlling or preventing infestation of plants by phytopathogenic fungi.
  • compositions possessing a greater biological activity, an advantageous spectrum of activity, an increased safety profile, improved physico-chemical properties, or increased biodegradability are also possible.
  • compositions comprising mixtures of different fungicidal compounds possessing different modes of action can address some of these needs (eg, by combining fungicides with differing spectrums of activity).
  • component (A) is a compound of formula (I): wherein Z is O; R 1 is selected from C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkylsulfonyl-C 1-6 alkyl, and C 3 - 6 cycloalkyl-C 1-4 alkyl, wherein each of the C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkylsulfonyl- C 1-6 alkyl, and C 3-6 cycloalkyl-C 1-4 alkyl groups is optionally substitute
  • R 1 is selected from C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkylsulfonyl-C 1-6 alkyl, and C 3 - 6 cycloalkyl-C 1-4 alkyl, wherein each of the C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkylsulfonyl- C 1-6 alkyl, and C 3-6 cycloalkyl-C 1-4 alkyl groups is optionally substituted with CN;
  • R 2a is selected from H, C 1-6 alkyl, C 3-6 cycloalkyl, and C 1-6 alkoxy-C 1-6 alkyl;
  • R 2b is selected from H, CN, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkoxy-C 1-6 alkyl, amino, and -NHC(
  • the component (A) is a compound of formula (I): wherein Z is O; R 1 is selected from C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkylsulfonyl-C 1-6 alkyl, and C 3 - 6 cycloalkyl-C 1-4 alkyl, wherein each of the C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkylsulfonyl- C 1-6 alkyl, and C 3-6 cycloalkyl-C 1-4 alkyl groups is optionally substituted with CN; R 2a is selected from H, C 1-6 alkyl, C 3-6 cycloalkyl, and C 1-6 alkoxy-C 1-6 alkyl; R 2b is selected from H, CN, C 1-6 alkyl, C 3-6 cycloalkyl, C 1-6 alkyl
  • Streptomyces chrestomyceticus comprises a nucleotide sequence which has at least 99.8 %, preferably at least 99.9%,, preferably at least 99.91%, 99.92%, 99.93%, 99.94%, 99.95%, 99.96%, 99.97%, 99.98%, or 99.99% identity to SEQ ID NO: 1.
  • the Streptomyces chrestomyceticus comprises a nucleotide sequence which has 100% identity to SEQ ID NO:1.
  • SEQ ID NO: 1 comprises the 16S RNA gene of Streptomyces chrestomyceticus Saigon413 deposited with the Westerdijk Institute under accession number CBS149411.
  • 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.
  • halogen refers to fluorine (fluoro or F), chlorine (chloro or Cl), bromine (bromo or Br) or iodine (iodo or I), and preferably fluoro or chloro.
  • amino refers to a -NH2 group.
  • Alkyl as used herein- in isolation or as part of a chemical group – represents straight-chain or branched hydrocarbons, preferably with 1 to 6 carbon atoms, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl, 1- methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2- dimethylpropyl, 1,1 -dimethylpropyl, 2,2- dimethylpropyl, 1 -ethylpropyl, hexyl, 1 -methylpentyl, 2- methylpentyl, 3-methylpentyl, 4- methylpentyl, 1,2-dimethylpropyl, 1,3-dimethylbutyl, 1,4-dimethylbutyl, 2,3-dimethylbutyl, 1,1- dimethylbutyl, 2,2-dimethylbutyl
  • Alkyl groups with 1 to 4 carbon atoms are preferred, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl.
  • cycloalkyl in isolation or as part of a chemical group - represents saturated or partially unsaturated mono-, bi- or tricyclic hydrocarbons, preferably with 3 to 10 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl or adamantyl. Cycloalkyls with 3, 4, 5, 6 or 7 carbon atoms are preferred, for example cyclopropyl or cyclobutyl.
  • alkoxy refers to a radical of the formula -OR a wherein R a is an alkyl radical as generally defined above. Examples of alkoxy include, but are not limited to methoxy, ethoxy, propoxy, iso-propoxy, and tert-butoxy.
  • alkoxyalkyl refers to an alkyl radical (as mentioned above) substituted with said alkoxy group. Examples are methoxymethyl, methoxyethyl, ethoxymethyl and propoxymethyl.
  • alkylamino refers to a radical of the formula RaNH- wherein Ra is an alkyl radical as generally defined above.
  • alkoxyamino refers to a radical of the formula RaNH-, wherein Ra is an alkoxy radical as generally defined above.
  • alkylsulfonyl refers to a radical of the formula -S(O) 2 R a wherein R a is an alkyl radical as generally defined above.
  • the weight ratio of component (A) to component (B) may preferably be from 100:1 to 1:100, from 50:1 to 1:50, from 20:1 to 1:40, from 15:1 to 1:30, from 12:1 to 1:25, from 10:1 to 1:20, from 5:1 to 1:15, from 3:1 to 1:10, or from 2:1 to 1:5.
  • fungicidal 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 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.
  • the compounds of formula (I) are, in any combination thereof, as set out below: - R 1 is selected from C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, and C 1-6 alkylsulfonyl-C 1-6 alkyl, wherein each of the C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl and C 1-6 alkylsulfonyl-C 1-6 alkyl groups is optionally substituted with CN, and preferably selected from CH 3 , CH 2 -CH 3 , CH 2 -O-CH 3 , CH 2 -SO 2 -CH 3 , and CH 2 CN; - R 2a is selected from H and C 1-6 alkyl, and preferably selected from H and CH 3 ; - R 2b is selected from H, C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, amino, and -NHC(O)C 1-6 alkyl
  • the compounds of formula (I) are, in any combination thereof, as set out below: - R 1 is selected from C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, and C 1-6 alkylsulfonyl-C 1-6 alkyl, wherein each of the C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl and C 1-6 alkylsulfonyl-C 1-6 alkyl groups is optionally substituted with CN, and preferably selected from CH 3 , CH 2 -CH 3 , CH 2 -O-CH 3 , CH 2 -SO 2 -CH 3 , and CH 2 CN; - R 2a is selected from H and C 1-6 alkyl, and preferably selected from H and CH 3 ; - R 2b is selected from H, C 1-6 alkyl, C 1-6 alkoxy-C 1-6 alkyl, amino, and -NHC(O)C 1-6 alkyl,
  • component (A) is a compound selected from compound no. X.01, X.02, X.03, X.04, X.05, X.06, X.07, X.08, X.09, X.10, X.11, X.12, X.13, X.14, X.15, X.16, X.17, X.18, X.19, X.20, X.21, X.22, and X.23, as defined in the Table X below. More preferably, component (A) is a compound selected from compound no. X.01, X.02, X.03, X.04, X.05, X.06, X.21, X.22, and X.23, as defined in the Table X below. Table X
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, oxathiapiprolin, picarbutrazox, pydiflumetofen, sedaxane, Streptomyces chrestomyceticus, zoxamide, N-[(1R)-1-benzyl-1,3-dimethyl- butyl]-8-fluoro-quinoline-3-carboxamide, and N-[(1R)-1
  • component (B) is a compound selected from the group consisting of acibenzolar-S- methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, oxathiapiprolin, picarbutrazox, pydiflumetofen, sedaxane, Streptomyces chrestomyceticus, zoxamide, and Compound Z (feneptamidoquin).
  • component (B) compounds are referred to herein and above by a so-called "ISO common name” or another "common name” being used in individual cases or a trademark name.
  • the component (B) compounds are known and are commercially available and/or can be prepared using procedures known in the art and/or procedures reported in the literature.
  • component (A) is compound no.
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis- Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, ethaboxam, fenpicoxamid, floryl
  • component (A) is compound no. X.02 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium
  • component (A) is compound no. X.03 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methoxymethyl)carbamoyl]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof, and component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole
  • component (A) is compound no. X.04 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methoxymethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium
  • component (A) is compound no. X.05 [methyl N-[4-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3- yl]phenyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, eth
  • component (A) is compound no. X.06 [3- [6-(cyclopropanecarbonylamino)-3-pyridyl]-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-imidazo[1,2- a]pyridine-6-carboxamide] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphon
  • component (A) is compound no. X.07 [methyl N-[4-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis- Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, ethaboxam, fenpic
  • component (A) is compound no. X.08 [methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3- yl]phenyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, ethabox
  • component (A) is compound no. X.09 [methyl N-[5-[6-[(4-fluoro-3-methyl-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate,
  • component (A) is compound no. X.10 [methyl N-[5-[6-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate,
  • component (A) is compound no. X.11 [methyl N-[5-[6-[(4-chloro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate
  • component (A) is compound no. X.12 [methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate,
  • component (A) is compound no. X.13 [methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]-7-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate,
  • component (A) is compound no. X.14 [methyl N-[5-[6-[cyanomethyl-(4-fluoro-3-methoxy-phenyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphon
  • component (A) is compound no. X.15 [methyl N-[5-[6-[(4-chloro-3-methoxy-phenyl)-(cyanomethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium
  • component (A) is compound no. X.16 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methylsulfonylmethyl)carbamoyl]imidazo[1,2-a]pyridin-3- yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole
  • component (A) is compound no. X.17 [N- (4-fluoro-3-methoxy-phenyl)-3-[6-(methoxycarbamoylamino)-3-pyridyl]-N-methyl-imidazo[1,2- a]pyridine-6-carboxamide] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate
  • component (A) is compound no. X.18 [methyl N-[5-[8-acetamido-6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphon
  • component (A) is compound no. X.19 [methyl N-[5-[6-[ethyl-(4-fluorophenyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis- Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, ethabox
  • component (A) is compound no. X.20 [methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3- yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole,
  • component (A) is compound no. X.21 [methyl ⁇ N ⁇ -[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-8-(methoxymethyl)imidazo[1,2- a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difeno
  • component (A) is compound no. X.22 [methyl N-[5-[6-[(2-methoxy-4-pyridyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphon
  • component (A) is compound no. X.23 [methyl N-[5-[6-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium
  • component (A) is compound no. X.01 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.02 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl
  • component (A) is compound no. X.03 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methoxymethyl)carbamoyl]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof, and component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metal
  • component (A) is compound no. X.04 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methoxymethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl
  • component (A) is compound no. X.05 [methyl N-[4-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3- yl]phenyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, oxathi
  • component (A) is compound no. X.06 [3-[6-(cyclopropanecarbonylamino)-3-pyridyl]-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-imidazo[1,2- a]pyridine-6-carboxamide] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.07 [methyl N-[4-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, oxathiapiprolin, picar
  • component (A) is compound no. X.08 [methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3- yl]phenyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, oxathiapipro
  • component (A) is compound no. X.09 [methyl N-[5-[6-[(4-fluoro-3-methyl-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, ox
  • component (A) is compound no. X.10 [methyl N-[5-[6-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, o
  • component (A) is compound no. X.11 [methyl N-[5-[6-[(4-chloro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.12 [methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, ox
  • component (A) is compound no. X.13 [methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]-7-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, ox
  • component (A) is compound no. X.14 [methyl N-[5-[6-[cyanomethyl-(4-fluoro-3-methoxy-phenyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.15 [methyl N-[5-[6-[(4-chloro-3-methoxy-phenyl)-(cyanomethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-
  • component (A) is compound no. X.16 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methylsulfonylmethyl)carbamoyl]imidazo[1,2-a]pyridin-3- yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metal
  • component (A) is compound no. X.17 [N-(4-fluoro-3-methoxy-phenyl)-3-[6-(methoxycarbamoylamino)-3-pyridyl]-N-methyl-imidazo[1,2- a]pyridine-6-carboxamide] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.18 [methyl N-[5-[8-acetamido-6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.19 [methyl N-[5-[6-[ethyl-(4-fluorophenyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, oxathiapi
  • component (A) is compound no. X.20 [methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3- yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metala
  • component (A) is compound no. X.21 [methyl ⁇ N ⁇ -[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-8-(methoxymethyl)imidazo[1,2- a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazo
  • component (A) is compound no. X.22 [methyl N-[5-[6-[(2-methoxy-4-pyridyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.23 [methyl N-[5-[6-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-
  • component (A) is compound no. X.01 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium
  • component (A) is compound no. X.02 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3- yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, dis
  • component (A) is compound no. X.03 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methoxymethyl)carbamoyl]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenocon
  • component (A) is compound no. X.04 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methoxymethyl)carbamoyl]imidazo[1,2-a]pyridin-3- yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, dis
  • component (A) is compound no. X.05 [methyl N-[4-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3- yl]phenyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate,
  • component (A) is compound no. X.06 [3-[6-(cyclopropanecarbonylamino)-3-pyridyl]-N-(4-fluoro-3-methoxy-phenyl)-N-methyl- imidazo[1,2-a]pyridine-6-carboxamide] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phospho
  • component (A) is compound no. X.07 [methyl N-[4-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis- Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, ethaboxam, f
  • component (A) is compound no. X.08 [methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3- yl]phenyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, eth
  • component (A) is compound no. X.09 [methyl N-[5-[6-[(4-fluoro-3-methyl-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate
  • component (A) is compound no. X.10 [methyl N-[5-[6-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphon
  • component (A) is compound no. X.11 [methyl N-[5-[6-[(4-chloro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phospho
  • component (A) is compound no. X.12 [methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate
  • component (A) is compound no. X.13 [methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]-7-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate
  • component (A) is compound no. X.14 [methyl N-[5-[6-[cyanomethyl-(4-fluoro-3-methoxy-phenyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium
  • component (A) is compound no. X.15 [methyl N-[5-[6-[(4-chloro-3-methoxy-phenyl)-(cyanomethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]- 2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium
  • component (A) is compound no. X.16 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methylsulfonylmethyl)carbamoyl]imidazo[1,2- a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenocon
  • component (A) is compound no. X.17 [N-(4-fluoro-3-methoxy-phenyl)-3-[6-(methoxycarbamoylamino)-3-pyridyl]-N-methyl-imidazo[1,2- a]pyridine-6-carboxamide] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium
  • component (A) is compound no. X.18 [methyl N-[5-[8-acetamido-6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium
  • component (A) is compound no. X.19 [methyl N-[5-[6-[ethyl-(4-fluorophenyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis- Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, eth
  • component (A) is compound no. X.20 [methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2- a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazo
  • component (A) is compound no. X.21 [methyl ⁇ N ⁇ -[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-8-(methoxymethyl)imidazo[1,2- a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, dif
  • component (A) is compound no. X.22 [methyl N-[5-[6-[(2-methoxy-4-pyridyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium
  • component (A) is compound no. X.23 [methyl N-[5-[6-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3- yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, diso
  • component (A) is compound no. X.01 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.02 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate ] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxy
  • component (A) is compound no. X.03 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methoxymethyl)carbamoyl]-8-methyl-imidazo[1,2- a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof, and component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metal
  • component (A) is compound no. X.04 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methoxymethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl
  • component (A) is compound no. X.05 [methyl N-[4-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3- yl]phenyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, oxathi
  • component (A) is compound no. X.06 [3-[6-(cyclopropanecarbonylamino)-3-pyridyl]-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-imidazo[1,2- a]pyridine-6-carboxamide] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.07 [methyl N-[4-[6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, oxathiapiprolin, picar
  • component (A) is compound no. X.08 [methyl N-[4-[6-[(4-chlorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3- yl]phenyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, oxathiapipro
  • component (A) is compound no. X.09 [methyl N-[5-[6-[(4-fluoro-3-methyl-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, ox
  • component (A) is compound no. X.10 [methyl N-[5-[6-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, o
  • component (A) is compound no. X.11 [methyl N-[5-[6-[(4-chloro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.12 [methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, ox
  • component (A) is compound no. X.13 [methyl N-[5-[6-[(4-fluorophenyl)-methyl-carbamoyl]-7-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, ox
  • component (A) is compound no. X.14 [methyl N-[5-[6-[cyanomethyl-(4-fluoro-3-methoxy-phenyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.15 [methyl N-[5-[6-[(4-chloro-3-methoxy-phenyl)-(cyanomethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-
  • component (A) is compound no. X.16 [methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methylsulfonylmethyl)carbamoyl]imidazo[1,2-a]pyridin-3- yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metal
  • component (A) is compound no. X.17 [N-(4-fluoro-3-methoxy-phenyl)-3-[6-(methoxycarbamoylamino)-3-pyridyl]-N-methyl-imidazo[1,2- a]pyridine-6-carboxamide] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.18 [methyl N-[5-[8-acetamido-6-[(4-fluorophenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.19 [methyl N-[5-[6-[ethyl-(4-fluorophenyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M, oxathiapi
  • component (A) is compound no. X.20 [methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3- yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metala
  • component (A) is compound no. X.21 [methyl ⁇ N ⁇ -[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-8-(methoxymethyl)imidazo[1,2- a]pyridin-3-yl]-2-pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazo
  • component (A) is compound no. X.22 [methyl N-[5-[6-[(2-methoxy-4-pyridyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-M,
  • component (A) is compound no. X.23 [methyl N-[5-[6-[(4-cyano-3-methoxy-phenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate] or a salt, or N-oxide thereof
  • component (B) is a compound selected from the group consisting of acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, chlorothalonil, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, florylpicoxamid, fluazinam, fludioxonil, fluopicolide, fluoxapiprolin, folpet, mandipropamid, mefentrifluconazole, metalaxyl-
  • the composition may comprise an additional active ingredient component (C), which is different to component (B), and is selected from the group consisting of acetamiprid, acibenzolar-S-methyl, ametoctradin, amisulbrom, azoxystrobin, Bacillus amyloliquefaciens, benzovindiflupyr, broflanilid, chlorothalonil, chlothianidin, chlorantraniliprole, Cis-Jasmone, cyantraniliprole, cyazofamid, cyclobutrifluram, cymoxanil, difenoconazole, disodium phosphonate, ethaboxam, fenpicoxamid, florylpicoxamid, fluazinam, fludioxonil, fluindapyr, fluopicolide, fluopyram, fluoxapiprolin, fluoxytioconazole, fluxamet
  • C additional active ingredient component
  • the composition according to the present invention can be used in the agricultural sector and related fields of use for controlling plant pests or on non-living materials for control of spoilage microorganisms or organisms potentially harmful to man.
  • the composition can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.
  • the term “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.
  • the composition according to the present invention can comprise a fungicidally effective amount of the component A and/or the component B.
  • locus as used herein 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.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits. It is also possible to use the composition according to the present invention as dressing agents for the treatment of plant propagation material for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.
  • the propagation material can be treated with a composition according to the present invention before planting: seed, for example, can be dressed before being sown.
  • the composition according to the present invention can also be applied to grains (coating), either by impregnating the seeds in a liquid formulation or by coating them with a solid formulation.
  • the composition can also be applied to the planting site when the propagation material is being planted, for example, to the seed furrow during sowing.
  • the invention relates also to such methods of treating plant propagation material and to the plant propagation material so treated.
  • plant propagation material is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There may be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion.
  • plant propagation material is understood to denote seeds.
  • Pesticidal agents referred to herein using their common name are known, for example, from "The Pesticide Manual", 19th Ed., British Crop Protection Council 2021.
  • the composition accorindg to the present invention can be used for controlling fungi in related areas, for example in the protection of technical materials, including wood and wood related technical products, in food storage, in hygiene management.
  • the invention could be used to protect non-living materials from fungal attack, e.g. lumber, wall boards and paint.
  • the composition according to the invention is effective against harmful microorganisms, such as microorganisms, that cause phytopathogenic diseases, in particular against phytopathogenic fungi and bacteria.
  • the composition of the invention may be used to control plant diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and/or Deuteromycete, Blasocladiomycete, Chrytidiomycete, Glomeromycete and/or Mucoromycete classes, and more preferably in the Oomycete classes.
  • the composition of the invention is effective in controlling a broad spectrum of plant diseases, such as foliar pathogens of ornamental, turf, vegetable, field, cereal, and fruit crops.
  • pathogens may include: Oomycetes, including Phytophthora diseases such as those caused by Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora and Phytophthora erythroseptica; Pythium diseases such as those caused by Pythium aphanidermatum, Pythium arrhenomanes, Pythium graminicola, Pythium irregulare, Pythium sylvaticum and Pythium ultimum; diseases caused by Peronosporales such as Peronospora destructor, Peronospora parasitica, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cubens
  • 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
  • composition accorindg to the present invention may also have activity against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scabies and other related species as well as certain protozoa.
  • bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scabies and other related species as well as certain protozoa.
  • target crops and/or useful plants to be protected typically comprise 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), millet, oats
  • Augustine grass and Zoysia grass herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for example grapes.
  • herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme
  • legumes for example beans, lentils, peas and soya beans
  • the useful plants and / or target crops in accordance with the invention include conventional as well as genetically enhanced or engineered varieties such as, for example, insect resistant (e.g. Bt. and VIP varieties) as well as disease resistant, herbicide tolerant (e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® and LibertyLink®) and nematode tolerant varieties.
  • suitable genetically enhanced or engineered crop varieties include the Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.
  • useful plants and/or “target crops” is to be understood as including also useful plants that have been rendered tolerant to herbicides like bromoxynil or classes of herbicides (such as, for example, HPPD inhibitors, ALS inhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5- enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors) as a result of conventional methods of breeding or genetic engineering.
  • herbicides like bromoxynil or classes of herbicides
  • EPSPS 5- enol-pyrovyl-shikimate-3-phosphate-synthase
  • GS glutamine synthetase
  • PPO protoporphyrinogen-oxidase
  • An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (Canola).
  • crops that have been rendered tolerant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady® , Herculex I® and LibertyLink®.
  • the term "useful plants" and/or “target crops” is to be understood as including those which naturally are or have been rendered resistant to harmful insects.
  • toxins which can be expressed include ⁇ -endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi.
  • An example of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut® (Syngenta Seeds).
  • VipCot ® Surgera 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).
  • useful plants and/or “target crops” is to be understood as including also useful plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0392225).
  • PRPs pathogenesis-related proteins
  • Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0392225, WO 95/33818, and EP-A-0353191.
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as ⁇ - endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonising nematodes, for example Photorhabdus spp.
  • insecticidal proteins from Bacillus cereus or Bacillus popilliae such as ⁇ - endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative
  • Xenorhabdus spp. such as Photorhabdus luminescens, Xenorhabdus nematophilus
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins
  • toxins produced by fungi such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins
  • agglutinins proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors
  • ribosome- inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecd
  • ⁇ -endotoxins for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1, Vip2, Vip3 or Vip3A
  • Vip vegetative insecticidal proteins
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701).
  • Truncated toxins for example a truncated Cry1Ab, are known.
  • modified toxins one or more amino acids of the naturally occurring toxin are replaced.
  • preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G- recognition sequence is inserted into a Cry3A toxin (see WO03/018810).
  • More examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0374753, WO93/07278, WO95/34656, EP-A-0427529, EP-A-451878 and WO03/052073.
  • transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0367 474, EP-A-0401979 and WO 90/13651.
  • the toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects.
  • Such insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).
  • Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard ® (maize variety that expresses a Cry1Ab toxin); YieldGard Rootworm ® (maize variety that expresses a Cry3Bb1 toxin); YieldGard Plus ® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin); Starlink ® (maize variety that expresses a Cry9C toxin); Herculex I ® (maize variety that expresses a Cry1Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B ® (cotton variety that expresses a Cry1Ac toxin); Bollgard I
  • transgenic crops are: 1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium. 2. Bt176 Maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31790 St.
  • This toxin is Cry3A055 modified by insertion of a cathepsin-G- protease recognition sequence.
  • the preparation of such transgenic maize plants is described in WO 03/018810.
  • MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9.
  • MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects. 5.
  • NK603 ⁇ MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • CP4 EPSPS obtained from Agrobacterium sp. strain CP4
  • Rup® contains glyphosate
  • Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • Compounds of formula (I) used in accordance with the present invention can be made as shown in the following schemes 1 to 19, in which, unless otherwise stated, the definition of each variable is as defined in the present invention.
  • Compounds of formula (I) can be prepared via Suzuki cross coupling of compounds of formula (II), wherein X is chloro (Cl), bromo (Br) or iodo (I), and a compound of formula (III), wherein either R 7 is independently from each other hydrogen, C 1 -C 6 alkyl or wherein two R 7 together can form a C 3 -C 8 cycloalkyl, in the presence of a base, such as Cs 2 CO 3 , K 2 CO 3 or NaOtBu, and a suitable palladium catalyst, such as tetrakistriphenylphosphinepalladium, palladium dichloride, [1,1- bis(diphenylphosphino)ferrocene]dichloropalladium(II), palladium acetate or bis(diphenylphosphine)palladium(II) chloride), in a suitable solvent, such as dimethylformamide, dioxane, tetrahydrofuran
  • the outcome of the reaction can be improved by using a base, such as sodium bicarbonate or potassium carbonate, or by using an acid, such as p-toluenesulfonic acid or hydrogen bromide.
  • a base such as sodium bicarbonate or potassium carbonate
  • an acid such as p-toluenesulfonic acid or hydrogen bromide.
  • this transformation can be utilized to prepare compounds of formula (VII), wherein R 8 is a C 1 -C 6 alkyl, from a compound of formula (XII), wherein R 8 is a C 1 -C 6 alkyl, and to prepare compounds of formula (XIII) from a compound of formula (XIV).
  • compounds of formula (I) can be prepared by the reaction of a compound of formula (XV), with a compounds of formula (V) and a coupling agent, such as N,N'-dicyclohexylcarbodiimide, bis(2- oxo-3-oxazolidinyl)phosphinic chloride, 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphophonic anhydride or cyanuric chloride, and, optionally, a base such as triethylamine, ethyldiisopropylamine or N-methylmorpholine in a suitable solvent such ethyl acetate, dimethylformamide, tetrahydrofuran or dichloromethane.
  • a coupling agent such as N,N'-dic
  • Scheme 8 Compound of formula (XV) can be prepared by the saponification of compounds of formula (XVI), wherein R 8 is a C 1 -C 6 alkyl, using a base such as NaOH or LiOH, in a suitable solvent such as methanol, ethanol or water at temperature between room temperature and reflux. This transformation is depicted in Scheme 9.
  • compounds of formula (II), wherein X is Cl, Br or I can be prepared by the reaction of a compound of formula (XVII) and a halogenating agent, such as N-chlorosuccinimide, N- bromosuccinimide, N-iodosuccinimide or bromine in a suitable solvent, such as dichloromethane, chloroform, tetrahydrofuran or acetonitrile. This transformation is depicted in schem 11.
  • a halogenating agent such as N-chlorosuccinimide, N- bromosuccinimide, N-iodosuccinimide or bromine
  • a suitable solvent such as dichloromethane, chloroform, tetrahydrofuran or acetonitrile.
  • Compounds of formula (XVII) can be prepared by the reaction of a compound of formula (XIII), with a compounds of formula (V) and a coupling agent, such as N,N'-dicyclohexylcarbodiimide, bis(2-oxo-3- oxazolidinyl)phosphinic chloride, 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphophonic anhydride or cyanuric chloride, and, optionally, a base such as triethylamine, ethyldiisopropylamine or N-methylmorpholine in a suitable solvent such ethyl acetate, dimethylformamide, tetrahydrofuran or dichloromethane.
  • a coupling agent such as N,
  • compounds of formula (II) can be prepared by the reaction of a compound of formula (XVIII), with a compounds of formula (XIX), wherein Y is Cl, Br, I, OSO 2 CF 3 , OSO 2 C 6 H4CH 3 or OSO 2 CH 3 , in the presence of a base, such as Cs 2 CO 3 , K 2 CO 3 or NaOtBu. This transformation is depicted in scheme 14.
  • Scheme 15 compounds of formula (I) can be synthesized by reacting compounds of formula (XXI), wherein X is Cl, Br or I, with amines of formula (V) and carbon monoxide in the presence of a catalyst such as [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II), and, optionally, a base such as triethylamine or sodium carbonate.
  • a catalyst such as [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II)
  • a base such as triethylamine or sodium carbonate.
  • compounds of formula (I) can be prepared by the reaction of a compound of formula (XXIII) with a compound of formula (XXIV), wherein Y is OH, and a coupling agent, such as N,N'- dicyclohexylcarbodiimide, bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 2-(1H-benzotriazole-1-yl)- 1,1,3,3-tetramethyluronium hexafluorophosphate, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, propylphosphonic anhydride or cyanuric chloride, and, optionally, a base such as triethylamine, ethyldiisopropylamine or N-methylmorpholine in a suitable solvent such ethyl acetate, dimethylformamide, tetrahydrofuran or dichloromethane.
  • the transformation can also be accomplished by the reaction of a compound of formula (XXIII) with a compound of formula (XXIV), wherein Y is Cl, and, optionally, a base such as, triethylamine, ethyldiisopropylamine or pyridine in a suitable solvent such as ethyl acetate, pyridine or tetrahydrofuran.
  • a base such as, triethylamine, ethyldiisopropylamine or pyridine
  • a suitable solvent such as ethyl acetate, pyridine or tetrahydrofuran.
  • the compounds of formula (I) according to the present invention can be obtained by using standard synthesis techniques known to the person skilled in the art.
  • Non-exhaustive examples include oxidation reactions, reduction reactions, hydrolysis reactions, coupling reactions, aromatic nucleophilic or electrophilic substitution reactions, nucleophilic substitution reactions, nucleophilic addition reactions, olefination reactions, oxime formation, alkylation and halogenation reactions.
  • the present invention also provides intermediates useful for the preparation of the compound of formula (I) according to the present invention. The below intermediate forms a further aspect of the invention.
  • R 2a , R 2b and R 2c independently selected from H, hydroxy, halogen, CN, C 1-6 alkyl, C 3-6 cycloalkyl, C 1 - 6 alkoxy-C 1-6 alkyl, C 3-6 cycloalkyl-C 1-4 alkyl, C 1-6 alkylsulfanyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyl, C 1-6 alkoxy, amino, and NHC(O)C 1-6 alkyl; and preferably R 2a , R 2b and R 2c are independently selected from H, halogen, CN, C 1-4 alkyl and C 1-4 alkoxy; and more preferably R 2a is selected from H, C 1-6 alkyl, C 3- 6 cycloalkyl, and C 1-6 alkoxy-C 1-6 alkyl, R 2b is selected from H, CN, C 1-6 alkyl, C 3-6 cyclo
  • composition according to the present invention may be used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they may be conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomising, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
  • Suitable carriers and/or adjuvants e.g. for agricultural use, can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.
  • Suspension concentrates are aqueous formulations in which finely divided solid particles of the active compound are suspended.
  • Such formulations include anti-settling agents and dispersing agents and may further include a wetting agent to enhance activity as well an anti-foam and a crystal growth inhibitor.
  • these concentrates are diluted in water and normally applied as a spray to the area to be treated.
  • the amount of active ingredient may range from 0.5% to 95% of the concentrate.
  • Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers. The particles contain the active ingredient retained in a solid matrix. Typical solid matrices include fuller’s earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain from 5% to 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.
  • Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.
  • Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which treatment is required.
  • Typical carriers for granular formulations include sand, fuller’s earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate and other organic or inorganic materials which absorb or which can be coated with the active compound.
  • Granular formulations normally contain 5% to 25% of active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and/or stickers such as dextrins, glue or synthetic resins.
  • Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.
  • Microcapsules are typically droplets or granules of the active ingredient enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates. Encapsulated droplets are typically 1 to 50 microns in diameter.
  • the enclosed liquid typically constitutes 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound.
  • Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores.
  • Granules typically range from 1 millimetre to 1 centimetre and preferably 1 to 2 millimetres in diameter.
  • Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and granular carbon.
  • Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.
  • Other useful formulations for agrochemical applications include simple solutions of the comopnents A and B in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents.
  • Pressurised sprayers wherein the active ingredient is dispersed in finely-divided form as a result of vaporisation of a low boiling dispersant solvent carrier, may also be used.
  • Liquid carriers that can be employed include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide,
  • Water is generally the carrier of choice for the dilution of concentrates.
  • suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller’s earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin.
  • a broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation.
  • Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C.sub.
  • soaps such as sodium stearate
  • alkylnaphthalenesulfonate salts 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 lauryl trimethylammonium chloride
  • polyethylene glycol esters of fatty acids such as polyethylene glycol stearate
  • block copolymers of ethylene oxide and propylene oxide and salts of mono and dialkyl phosphate esters.
  • adjuvants commonly utilized in agricultural compositions include crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, anti- foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and sticking agents.
  • 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 active ingredient component (C) are as follows, wherein the term “TX” represents a compound according to the definition of component (A) of the composition of the present invention selected from compound no.
  • Israelensis + TX Bacillus thuringiensis subsp. Japonensis + TX, Bacillus thuringiensis subsp. Kurstaki + TX, Bacillus thuringiensis subsp. Tenebrionis + TX, Bacillus thuringiensis subspec.
  • lecontei NPV + TX nickel bis(dimethyldithiocarbamate) + TX, niclosamide + TX, niclosamide-olamine + TX, nicofluprole + TX, nitenpyram + TX, nithiazine + TX, nitrapyrin + TX, octadeca-2,13-dien-1-yl acetate + TX, octadeca- 3,13-dien-1-yl acetate + TX, octhilinone + TX, omethoate + TX, orfralure + TX, Orius spp.
  • TX trifenmorph + TX, trifluenfuronate + TX, triflumezopyrim + TX, trimedlure + TX, trimedlure A + TX, trimedlure B1 + TX, trimedlure B2 + TX, trimedlure C + TX, trimethacarb + TX, triphenyltin acetate + TX, triphenyltin hydroxide + TX, trunc-call + TX, tyclopyrazoflor + TX, Typhlodromus occidentalis + TX, uredepa + TX, Verticillium lecanii + TX, Verticillium spp.
  • acridum + TX Metarhizium anisopliae var. anisopliae + TX, metarylpicoxamid + TX, metconazole + TX, metepa + TX, methacrifos + TX, methanesulfonyl fluoride + TX, methasulfocarb + TX, methiotepa + TX, methocrotophos + TX, methoprene + TX, methoquin-butyl + TX, methothrin + TX, methoxychlor + TX, methyl (Z)-2-(5- cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate + TX, methyl (Z)-2-(5-cyclopentyl-2-methyl- phenoxy)-3-methoxy-prop-2-enoate (these compounds may be prepared from the methods described in WO2020/193387) + TX,
  • Bacillus subtilis strain AQ178 + TX Bacillus subtilis strain AQ153 + TX, Bacillus subtilis strain AQ743 + TX, Bacillus subtilis strain QST 713 (CEASE®, Serenade®, Rhapsody®) + TX, Bacillus subtilis strain QST 714 (JAZZ®) + TX, Bacillus subtilis strain QST3002 + TX, Bacillus subtilis strain QST3004 + TX, Bacillus subtilis var.
  • amyloliquefaciens strain FZB24 (Taegro®, Rhizopro®) + TX, Bacillus thuringiensis aizawai GC 91 (Agree®) + TX, Bacillus thuringiensis Cry 2Ae + TX, Bacillus thuringiensis Cry1Ab + TX, Bacillus thuringiensis israelensis (BMP123®, Aquabac®, VectoBac®) + TX, Bacillus thuringiensis kurstaki (Javelin®, Deliver®, CryMax®, Bonide®, Scutella WP®, Turilav WP ®, Astuto®, Dipel WP®, Biobit®, Foray®) + TX, Bacillus thuringiensis kurstaki BMP 123 (Baritone®) + TX, Bacillus thuringiensis kurstaki HD-1 (Bioprotec-CAF / 3P®) + TX
  • TX Botrytis cineria + TX, Bradyrhizobium japonicum (TerraMax®) + TX, Brevibacillus brevis + TX, Burkholderia cepacia (Deny®, Intercept®, Blue Circle®) + TX, Burkholderia gladii + TX, Burkholderia gladioli + TX, Burkholderia spp.
  • TX Canadian thistle fungus (CBH Canadian Bioherbicide®) + TX, Candida butyri + TX, Candida famata + TX, Candida fructus + TX, Candida glabrata + TX, Candida guilliermondii + TX, Candida melibiosica + TX, Candida oleophila strain O + TX, Candida parapsilosis + TX, Candida pelliculosa + TX, Candida pulcherrima + TX, Candida reuêtii + TX, Candida saitoana (Bio-Coat®, Biocure®) + TX, Candida sake + TX, Candida spp.
  • TX Cladosporium tenuissimum + TX, Clonostachys rosea (EndoFine®) + TX, Colletotrichum acutatum + TX, Coniothyrium minitans (Cotans WG®) + TX, Coniothyrium spp.
  • TX Filobasidium floriforme + TX, Fusarium acuminatum + TX, Fusarium chlamydosporum + TX, Fusarium oxysporum (Fusaclean®, Biofox C®) + TX, Fusarium proliferatum + TX, Fusarium spp. + TX, Galactomyces geotrichum + TX, Gliocladium catenulatum (Primastop®, Prestop®) + TX, Gliocladium roseum + TX, Gliocladium spp.
  • TX Lagenidium giganteum (Laginex®) + TX, Lecanicillium lecanii (formerly known as Verticillium lecanii (Mycotal®) conidia of strain KV01 (e.g. Vertalec® by Koppert/Arysta) + TX, Lecanicillium longisporum (Vertiblast®) + TX, Lecanicillium muscarium (Vertikil®) + TX, Lymantria Dispar nucleopolyhedrosis virus (Disparvirus®) + TX, Marinococcus halophilus + TX, Meira geulakonigii + TX, Metarhizium anisopliae (Destruxin WP®) + TX, Metarhizium anisopliae (Met52®) + TX, Metschnikowia fruticola (Shemer®) + TX, Metschnikowia pulcherrima + TX, Microdochium dimerum (Antibot®) + TX
  • NRRL 305408 + TX, Mycorrhizae spp. (AMykor®, Root Maximizer®) + TX, Myrothecium verrucaria strain AARC-0255 (DiTera®, BROS PLUS®) + TX, Ophiostoma piliferum strain D97 (Sylvanex®) + TX, Paecilomyces farinosus + TX, Paecilomyces lilacinus strain 251 (MeloCon WG®) + TX, Paecilomyces linacinus (Biostat WP®) + TX, Paenibacillus polymyxa + TX, Pantoea agglomerans (BlightBan C9-1®) + TX, Pantoea spp.
  • TX Pasteuria nishizawae in particular strain Pn1 (CLARIVA from Syngenta/ChemChina); + TX, Pasteuria spp. (Econem®) + TX, Penicillium aurantiogriseum + TX, Penicillium billai (Jumpstart®, TagTeam®) + TX, Penicillium brevicompactum + TX, Penicillium frequentans + TX, Penicillium griseofulvum + TX, Penicillium purpurogenum + TX, Penicillium spp.
  • TX Penicillium viridicatum + TX, Phlebiopsis gigantean (Rotstop®) + TX, phosphate solubilizing bacteria (Phosphomeal®) + TX, Phytophthora cryptogea + TX, Phytophthora palmivora (Devine®) + TX, Pichia anomala + TX, Pichia guilliermondii + TX, Pichia membranaefaciens + TX, Pichia onychis + TX, Pichia stipites + TX, Pseudomonas aeruginosa + TX, Pseudomonas aureofasciens (Spot-Less Biofungicide®) + TX, Pseudomonas cepacia + TX, Pseudomonas chlororaphis (AtEze®) + TX, Pseudomonas corrugate + TX, P
  • TX Pseudomonas syringae (Bio-Save®) + TX, Pseudomonas viridiflava + TX, Pseudozyma flocculosa strain PF-A22 UL (Sporodex L®) + TX, Puccinia canaliculata + TX, Puccinia thlaspeos (Wood Warrior®) + TX, Pythium paroecandrum + TX, Pythium oligandrum (Polygandron®, Polyversum®) + TX, Pythium periplocum + TX, Rhanella aquatilis + TX, Rhanella spp.
  • Rhizobia Distal®, Vault®
  • Rhizoctonia + TX Rhodococcus globerulus strain AQ719 + TX, Rhodosporidium diobovatum + TX, Rhodosporidium toruloides + TX, Rhodotorula glutinis + TX, Rhodotorula graminis + TX, Rhodotorula mucilagnosa + TX, Rhodotorula rubra + TX, Rhodotorula spp.
  • Trichoderma asperellum T34 Biocontrol®
  • TX Trichoderma atroviride
  • Trichoderma gamsii TX
  • Trichoderma hamatum TH 382 + TX Trichoderma harzianum rifai (Mycostar®) + TX
  • Trichoderma harzianum T-22 Trianum- P®, PlantShield HC®, RootShield®, Trianum-G® + TX, Trichoderma harzianum T-39 (Trichodex®) + TX, Trichoderma inhamatum + TX, Trichoderma koningii + TX, Trichoderma lignorum + TX, Trichoderma longibrachiatum + TX, Trichoderma polysporum (Binab T®) + TX, Trichoderma spp.
  • LC 52 (Sentinel®) + TX, Trichoderma taxi + TX, Trichoderma virens (formerly Gliocladium virens GL-21) (SoilGuard®) + TX, Trichoderma virens + TX, Trichoderma viride + TX, Trichoderma viride strain ICC 080 (Remedier®) + TX, Trichosporon pullulans + TX, Trichosporon spp. + TX, Trichothecium roseum + TX, Trichothecium spp.
  • TX maydis + TX, various bacteria and supplementary micronutrients (Natural II®) + TX, various fungi (Millennium Microbes®) + TX, Verticillium chlamydosporium + TX, Vip3Aa20 (VIPtera®) + TX, Virgibaclillus marismortui + TX, Xanthomonas campestris pv.
  • TX Bombus terrestris (Beeline®, Tripol®) + TX, Bombus terrestris (Natupol Beehive®) + TX, Cephalonomia stephanoderis + TX, Chilocorus nigritus + TX, Chrysoperla carnea (Chrysoline®, Chrysopa®) + TX, Chrysoperla rufilabris + TX, Cirrospilus ingenuus + TX, Cirrospilus quadristriatus + TX, Citrostichus phyllocnistoides + TX, Closterocerus chamaeleon + TX, Closterocerus spp.
  • TX Coccidoxenoides perminutus (Planopar®) + TX, Coccophagus cowperi + TX, Coccophagus lycimnia + TX, Cotesia flavipes + TX, Cotesia plutellae + TX, Cryptolaemus montrouzieri (Cryptobug®, Cryptoline®) + TX, Cybocephalus nipponicus + TX, Dacnusa sibirica (Minusa®, DacDigline®, Minex®) + TX, Delphastus catalinae (Delphastus®) + TX, Delphastus pusillus + TX, Diachasmimorpha krausii + TX, Diachasmimorpha longicaudata + TX, Diaparsis jucunda + TX, Diaphorencyrtus aligarhensis + TX, Diglyphus isaea (Diminex®, Miglyphus,
  • TX Steinernematid spp. (Guardian Nematodes®) + TX, Stethorus punctillum (Stethorus®) + TX, Tamarixia radiate + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Trichogramma brassicae (Tricholine b®) + TX, Trichogramma brassicae (Tricho-Strip®) + TX, Trichogramma evanescens + TX, Trichogramma minutum + TX, Trichogramma ostriniae + TX, Trichogramma platneri + TX, Trichogramma pretiosum + TX, Xanthopimpla stemmator + TX; abscisic acid + TX, Aminomite® + TX, BioGain® + TX, bioSea® + TX, CAS Number: 2643947-26-4 + TX, Chondroster
  • NCAIM (P) B001389) (WO 2013/034938) from Certis USA LLC + TX
  • Bacillus pumilus in particular strain BU F-33, having NRRL Accession No. 50185 (CARTISSA® from BASF, EPA Reg. No.71840-19) + TX
  • Bacillus subtilis CX-9060 from Certis USA LLC
  • Bacillus sp. in particular strain D747 (available as DOUBLE NICKEL® from Kumiai Chemical Industry Co., Ltd.), having Accession No. FERM BP-8234, U.S.
  • Patent No.7,094,592 + TX Bacillus subtilis strain BU1814, (VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA from BASF SE) + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 having Accession No. DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA Registration No.70127-5)) + TX, Bacillus subtilis, in particular strain QST713/AQ713 (having NRRL Accession No. B-21661 and described in U.S.
  • Patent No.6,060,051 available as SERENADE® OPTI or SERENADE® ASO from Bayer CropScience LP, US
  • TX Paenibacillus polymyxa
  • strain AC-1 e.g. TOPSEED® from Green Biotech Company Ltd.
  • TX Paenibacillus sp. strain having Accession No. NRRL B-50972 or Accession No. NRRL B-67129, WO 2016/154297 + TX, Pantoea agglomerans, in particular strain E325 (Accession No.
  • NRRL B-21856 (available as BLOOMTIME BIOLOGICALTM FD BIOPESTICIDE from Northwest Agri Products) + TX, Pseudomonas proradix (e.g. PRORADIX® from Sourcon Padena) + TX; Aureobasidium pullulans, in particular blastospores of strain DSM14940, blastospores of strain DSM 14941 or mixtures of blastospores of strains DSM14940 and DSM14941 (e.g., BOTECTOR® and BLOSSOM PROTECT® from bio-ferm, CH) + TX, Pseudozyma aphidis (as disclosed in WO2011/151819 by Yissum Research Development Company of the Hebrew University of Jerusalem) + TX, Saccharomyces cerevisiae, in particular strains CNCM No.1-3936, CNCM No.1-3937, CNCM No.1-3938 or CNCM No.1-3939 (WO 2010/086790) from
  • DSM 23117 (available as RHIZOVITAL® from ABiTEP, DE) + TX
  • Bacillus amyloliquefaciens in particular strain D747 (available as Double NickelTM from Kumiai Chemical Industry Co., Ltd., having accession number FERM BP-8234, US Patent No.7,094,592) + TX
  • Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® (WP) from FMC Corporation) + TX
  • Bacillus licheniformis in particular strain SB3086, having Accession No.
  • ATCC 55406, WO 2003/000051 (available as ECOGUARD® Biofungicide and GREEN RELEAFTM from Novozymes) + TX, Bacillus methylotrophicus strain BAC-9912 (from Chinese Academy of Sciences’ Institute of Applied Ecology) + TX, Bacillus mycoides, isolate, having Accession No. B-30890 (available as BMJ TGAI® or WG and LifeGardTM from Certis USA LLC) + TX, Bacillus pumilus, in particular strain GB34 (available as Yield Shield® from Bayer AG, DE) + TX, Bacillus pumilus, in particular strain QST2808 (available as SONATA® from Bayer CropScience LP, US, having Accession No.
  • Patent No.5,061,495 + TX Bacillus subtilis strain Y1336 (available as BIOBAC® WP from Bion- Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos.4764, 5454, 5096 and 5277) + TX, Bacillus subtilis var. amyloliquefaciens strain FZB24 having Accession No. DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA Registration No.70127-5)) + TX, Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos.
  • NRRL B-50897, WO 2017/019448 e.g., HOWLERTM and ZIO® from AgBiome Innovations, US
  • TX Pseudomonas chlororaphis
  • strain MA342 e.g. CEDOMON®, CERALL®, and CEDRESS® by Bioagri and Koppert
  • TX Pseudomonas fluorescens strain A506 (e.g. BLIGHTBAN® A506 by NuFarm) + TX
  • Pseudomonas proradix e.g.
  • PRORADIX® from Sourcon Padena + TX
  • Streptomyces griseoviridis strain K61 also known as Streptomyces galbus strain K61
  • DSM 7206 Streptomyces galbus strain K61
  • MYCOSTOP® from Verdera, PREFENCE® from BioWorks, cf.
  • BIOKUPRUMTM by AgriLife + TX
  • Chaetomium globosum available as RIVADIOM® by Rivale
  • TX Cladosporium cladosporioides
  • strain H39 having Accession No. CBS122244, US 2010/0291039 (by Stichting Moowgrass Onderzoek) + TX
  • Coniothyrium minitans in particular strain CON/M/91-8 (Accession No. DSM9660, e.g.
  • strain ICC 080 having Accession No. IMI 392151 (e.g., BIO-TAMTM from Isagro USA, Inc. or BIODERMA® by Agrobiosol de Mexico, S.A. de C.V.) + TX, Penicillium vermiculatum + TX, Phlebiopsis gigantea strain VRA 1992 (ROTSTOP® C from danstar Ferment) + TX, Pseudozyma flocculosa, strain PF-A22 UL (available as SPORODEX® L by Plant Products Co., CA) + TX, Saccharomyces cerevisiae strain LAS117 cell walls (CEREVISANE® from Lesaffre, ROMEO® from BASF SE) + TX, Saccharomyces cerevisiae strains CNCM No.1-3936, CNCM No.1-3937, CNCM No.1-3938, CNCM No.1-3939 (WO 2010/086790) from Lesaffre et Compag
  • T- Gro from Andermatt Biocontrol + TX
  • Trichoderma atroviride strain 77B T77 from Andermatt Biocontrol
  • Trichoderma atroviride strain ATCC 20476 IMI 206040
  • Trichoderma atroviride strain LC52 e.g. Tenet by Agrimm Technologies Limited
  • Trichoderma atroviride strain LU132 e.g. Sentinel from Agrimm Technologies Limited
  • TX Trichoderma atroviride strain NMI no. V08/002388 + TX
  • Trichoderma atroviride strain NMI no. V08/002389 + TX Trichoderma atroviride strain NMI no.
  • Patent No.8,431,120 (from Bi-PA)) + TX, Trichoderma atroviride,strain CNCM 1-1237 (e.g. Esquive® WP from Agrauxine, FR) + TX, Trichoderma fertile (e.g. product TrichoPlus from BASF) + TX, Trichoderma gamsii (formerly T. viride) + TX, Trichoderma gamsii (formerly T. viride) strain ICC 080 (IMI CC 392151 CABI) (available as BIODERMA® by AGROBIOSOL DE MEXICO, S.A.
  • Trichoderma gamsii strain ICC080 IMI CC 392151 CABI, e.g. BioDerma by AGROBIOSOL DE MEXICO, S.A. DE C.V.
  • + TX Trichoderma harmatum + TX
  • Trichoderma harmatum having Accession No. ATCC 28012 + TX, Trichoderma harzianum + TX, Trichoderma harzianum rifai T39 (e.g.
  • Trichodex® from Makhteshim, US + TX, Trichoderma harzianum strain Cepa SimbT5 (from Simbiose Agro), + TX, Trichoderma harzianum strain DB 103 (available as T-GRO® 7456 by Dagutat Biolab) + TX, Trichoderma harzianum strain ITEM 908 (e.g. Trianum-P from Koppert) + TX, Trichoderma harzianum strain T-22 (e.g. Trianum-P from Andermatt Biocontrol or Koppert) + TX, Trichoderma harzianum strain TH35 (e.g.
  • Trichoderma polysporum strain IMI 206039 e.g. Binab TF WP by BINAB Bio- Innovation AB, Sweden
  • TX Trichoderma stromaticum having Accession No. Ts3550 (e.g. Tricovab by CEPLAC, Brazil) + TX
  • Trichoderma virens also known as Gliocladium virens
  • strain GL-21 e.g. SoilGard by Certis, US
  • Trichoderma virens strain G-41 formerly known as Gliocladium virens (Accession No.
  • ATCC 20906 (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP from BioWorks, US) + TX, Trichoderma viride in particular strain B35 (Pietr et al., 1993, Zesz. Nauk. A R w Szczecinie 161: 125-137) + TX, Trichoderma viride strain TV1(e.g. Trianum-P by Koppert) + TX, Ulocladium oudemansii strain U3, having Accession No.
  • NM 99/06216 e.g., BOTRY-ZEN® by Botry-Zen Ltd, New Zealand and BOTRYSTOP® from BioWorks, Inc.
  • TX Verticillium albo-atrum (formerly V. dahliae) strain WCS850 having Accession No.
  • WCS850 deposited at the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® by Tree Care Innovations) + TX, Verticillium chlamydosporium + TX; a mixture of Azotobacter vinelandii and Clostridium pasteurianum (available as INVIGORATE® from Agrinos) + TX, a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available as QUARTZO® (WG), PRESENCE® (WP) from FMC Corporation) + TX, Azorhizobium caulinodans, in particular strain ZB-SK-5 + TX, Azospirillum brasilense (e.g., VIGOR® from KALO, Inc.) + TX, Azospirillum lipoferum (e.g., VERTEX-IFTM from TerraMax, Inc.) + TX, Azotobacter chroococcum, in particular strain H
  • NRRL B-5015 + TX
  • Bacillus amyloliquefaciens in particular strain FZB42 e.g. RHIZOVITAL® from ABiTEP, DE
  • Bacillus amyloliquefaciens in particular strain IN937a + TX Bacillus amyloliquefaciens pm414 (LOLI-PEPTA® from Biofilm Crop Protection) + TX
  • Bacillus amyloliquefaciens SB3281 ATCC # PTA-7542, WO 2017/205258
  • Bacillus amyloliquefaciens TJ1000 available as QUIKROOTS® from Novozymes
  • Bacillus cereus family member EE128 NRRL No.
  • YIELD SHIELD® from Bayer Crop Science, DE
  • + TX Bacillus pumilus in particular strain QST2808 (Accession No. NRRL No. B-30087) + TX, Bacillus siamensis in particular strain KCTC 13613T + TX, Bacillus subtilis in particular strain AQ30002 (Accession No. NRRL No. B-50421 and described in U.S. Patent Application No.13/330,576) + TX, Bacillus subtilis in particular strain AQ30004 (NRRL No. B-50455 and described in U.S. Patent Application No. 13/330,576) + TX, Bacillus subtilis in particular strain MBI 600 (e.g.
  • BIOBOOST® from Brett Young Seeds + TX, Lactobacillus sp. (e.g. LACTOPLANT® from LactoPAFI) + TX, Mesorhizobium cicer (e.g., NODULATOR from BASF SE) + TX, Paenibacillus polymyxa in particular strain AC-1 (e.g. TOPSEED® from Green Biotech Company Ltd.) + TX, Pseudomonas aeruginosa in particular strain PN1 + TX, Pseudomonas proradix (e.g.
  • PRORADIX® from Sourcon Padena + TX, Rhizobium leguminosarium biovar viciae (e.g., NODULATOR from BASF SE) + TX, Rhizobium leguminosarum in particular bv. viceae strain Z25 (Accession No. CECT 4585) + TX, Serratia marcescens in particular strain SRM (Accession No. MTCC 8708), + TX, Sinorhizobium meliloti strain NRG-185-1 (NITRAGIN® GOLD from Bayer CropScience) + TX, Thiobacillus sp. (e.g.
  • Trichoderma atroviride strain SC 1 (described in WO2009/116106) + TX, Trichoderma harzianum strain 1295-22 + TX, Trichoderma harzianum strain ITEM 908 + TX, Trichoderma harzianum strain T-22 (e.g. Trianum-P from Andermatt Biocontrol or Koppert) + TX, Trichoderma harzianum strain TSTh20, + TX, Trichoderma virens strain GI-3 + TX, Trichoderma virens strain GL-21 (e.g.
  • aizawai in particular serotype H-7 (e.g. FLORBAC® WG from Valent BioSciences, US) + TX, Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372, e.g. XENTARI® from Valent BioSciences) + TX, Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 (Accession No. ATCC 1276) (e.g. VECTOBAC® by Valent BioSciences, US) + TX, Bacillus thuringiensis subsp.
  • serotype H-7 e.g. FLORBAC® WG from Valent BioSciences, US
  • TX Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372, e.g. XENTARI® from Valent BioSciences) + TX
  • israeltaki strain ABTS 351 + TX Bacillus thuringiensis subsp. kurstaki strain BMP 123 (from Becker Microbial Products, IL, BARITONE from Bayer CropScience) + TX, Bacillus thuringiensis subsp. kurstaki strain EG 2348 (LEPINOX from Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain EG 7841 (CRYMAX from Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain HD-1 (e.g. DIPEL® ES from Valent BioSciences, US) + TX, Bacillus thuringiensis subsp.
  • BMP 123 from Becker Microbial Products, IL, BARITONE from Bayer CropScience
  • TX Bacillus thuringiensis subsp. kurstaki strain EG 2348 (LEPINOX from Certis, US) + TX
  • israeltaki strain PB 54 + TX Bacillus thuringiensis subsp. kurstaki strain SA 11 (JAVELIN from Certis, US) + TX, Bacillus thuringiensis subsp. kurstaki strain SA 12 (THURICIDE from Certis, US) + TX, Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428, e.g. NOVODOR® FC from BioFa DE) + TX, Bacillus thuringiensis var. Colmeri (e.g. TIANBAOBTC by Changzhou Jianghai Chemical Factory) + TX, Bacillus thuringiensis var.
  • SD-5428 e.g. NOVODOR® FC from BioFa DE
  • Bacillus thuringiensis var. Colmeri e.g. TIANBAOBTC by Changzhou Jianghai Chemical Factory
  • MBI206 TGAI and ZELTO® from Marrone Bio Innovations + TX
  • Chromobacterium subtsugae in particular strain PRAA4-1T e.g. MBI-203, e.g. GRANDEVO® from Marrone Bio Innovations
  • TX Chromobacterium subtsugae in particular strain PRAA4-1T
  • MBI-203 e.g. GRANDEVO® from Marrone Bio Innovations
  • TX Lecanicillium muscarium Ve6 (MYCOTAL from Koppert) + TX
  • Paenibacillus popilliae (formerly Bacillus popilliae, e.g. MILKY SPORE POWDERTM or MILKY SPORE GRANULARTM from St. Gabriel Laboratories) + TX
  • Serratia entomophila e.g.
  • ATCC74250 e.g. BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation
  • TX Metarhizium anisopliae 3213-1 (deposited under NRRL accession number 67074 disclosed in WO 2017/066094, Pioneer Hi-Bred International) + TX, Metarhizium robertsii 15013-1 (deposited under NRRL accession number 67073) + TX, Metarhizium robertsii 23013-3 (deposited under NRRL accession number 67075) + TX, Paecilomyces lilacinus strain 251 (MELOCON from Certis, US) + TX; Cydia pomonella (codling moth) granulosis virus (GV) + TX, Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV) + TX, of Adoxophyes orana (summer fruit tortrix) granul
  • Burkholderia cepacia (formerly known as Pseudomonas cepacia) + TX, Gigaspora spp. + TX, Glomus spp. + TX, Laccaria spp. + TX, LactoBacillus buchneri + TX, Paraglomus spp. + TX, Pisolithus tinctorus + TX, Pseudomonas spp. + TX, Rhizobium spp. in particular Rhizobium trifolii + TX, Rhizopogon spp. + TX, Scleroderma spp. + TX, Streptomyces spp. + TX, Suillus spp.
  • the weight ratio of component (A) to component (C) may preferably be from 100:1 to 1:100, from 50:1 to 1:50, from 20:1 to 1:40, from 15:1 to 1:30, from 12:1 to 1:25, from 10:1 to 1:20, from 5:1 yo 1:15, from 3:1 to 1:10, or from 2:1 to 1:5.
  • a further aspect of invention is related to a method of controlling or preventing an infestation of plants, e.g. useful plants such as crop plants, propagation material thereof, e.g. seeds, harvested crops, e.g.
  • Controlling or preventing means reducing infestation by insects or by phytopathogenic or spoilage microorganisms or organisms potentially harmful to man, especially fungal organisms, to such a level that an improvement is demonstrated.
  • a preferred method of controlling or preventing an infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, which comprises the application of a composition according to the present invention is foliar application.
  • the frequencies of application and the rate of application will depend on the risk of infestation by the corresponding pathogen or insect.
  • the compounds A and/or B of the composition according to the present invention can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying said compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field.
  • the compounds A and B as defined in the present invention may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.
  • composition according to the present invention may be prepared in a known manner, typically by intimately mixing and/or grinding the compound with extenders, for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • extenders for example solvents, solid carriers and, optionally, surface active compounds (surfactants).
  • surfactants surface active compounds
  • the application methods for the compositions that is the methods of controlling pests of the abovementioned type, such as spraying, atomizing, dusting, brushing on, dressing, scattering or pouring - which are to be selected to suit the intended aims of the prevailing circumstances - and the use of the composition for controlling pests of the abovementioned type are other subjects of the invention.
  • Typical rates of concentration are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm, of active ingredient.
  • the rate of application per hectare is preferably 1g to 2000 g of active ingredient per hectare, more preferably 10 to 1000 g/ha, most preferably 10 to 600 g/ha.
  • convenient dosages are from 10mg to 1g of active substance per kg of seeds.
  • rates of 0.001 to 50 g of a compound of formula (I) per kg of seed preferably from 0.01 to 10g per kg of seed are generally sufficient.
  • the composition according to the present invention can be applied either preventative, meaning prior to disease development or curative, meaning after disease development.
  • compositions of the invention may be employed in any conventional form, for example in the form of a twin pack, a powder for dry seed treatment (DS), an emulsion for seed treatment (ES), a flowable concentrate for seed treatment (FS), a solution for seed treatment (LS), a water dispersible powder for seed treatment (WS), a capsule suspension for seed treatment (CF), a gel for seed treatment (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK
  • compositions may be produced in conventional manner, e.g. by mixing the active ingredients with appropriate formulation inerts (diluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects).
  • appropriate formulation inerts diiluents, solvents, fillers and optionally other formulating ingredients such as surfactants, biocides, anti-freeze, stickers, thickeners and compounds that provide adjuvancy effects.
  • conventional slow release formulations may be employed where long lasting efficacy is intended.
  • Particularly formulations to be applied in spraying forms such as water dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents and other compounds that provide adjuvancy effects, e.g.
  • a seed dressing formulation is applied in a manner known per se to the seeds employing the combination of the invention and a diluent in suitable seed dressing formulation form, e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • suitable seed dressing formulation form e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • seed dressing formulations are known in the art.
  • Seed dressing formulations may contain the single active ingredients or the combination of active ingredients in encapsulated form, e.g.
  • the formulations include from 0.01 to 90% by weight of active ingredients, from 0 to 20% agriculturally acceptable surfactant and 10 to 99.99% solid or liquid formulation inerts and adjuvant(s), the active ingredients consisting of at least the components A and B as defined in the present invention, and optionally other active agents, particularly microbiocides or conservatives or the like.
  • Concentrated forms of compositions generally contain in between about 2 and 80%, preferably between about 5 and 70% by weight of active ingredients.
  • Application forms of formulation may for example contain from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active ingredients. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ diluted formulations.
  • Wettable powders a) b) c) active ingredients [components (A) and (B)] 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % - sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate - 6 % 10 % phenol polyethylene glycol ether - 2 % - (7-8 mol of ethylene oxide) highly dispersed silicic acid 5 % 10 % 10 % Kaolin 62 % 27 % -
  • the active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
  • Powders for dry seed treatment a) b) c) active ingredients [components (A) and (B)] 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 % - Kaolin 65 % 40 % - Talcum - - 20 %
  • 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 % (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 3 % castor oil polyglycol ether (35 mol of ethylene oxide) 4 % Cyclohexanone 30 % xylene mixture 50 % Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • Dusts a) b) c) active ingredients [components (A) and (B)] 5 % 6 % 4 % talcum 95 % - - Kaolin - 94 % - mineral filler - - 96 % 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 % Kaolin 82 % The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water.
  • Coated granules active ingredients [components (A) and (B)] 8 % polyethylene glycol (mol. wt.200) 3 % Kaolin 89 %
  • the finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol.
  • Non-dusty coated granules are obtained in this manner.
  • Suspension concentrate active ingredients [components (A) and (B)] 40 % propylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 % Sodium lignosulfonate 10 % carboxymethylcellulose 1 % silicone oil (in the form of a 75 % emulsion in water) 1 % Water 32 %
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • Flowable concentrate for seed treatment active ingredients [components (A) and (B)] 40 % propylene glycol 5 % copolymer butanol PO/EO 2 % tristyrenephenole with 10-20 moles EO 2 % 1,2-benzisothiazolin-3-one (in the form of a 20% solution in water) 0.5 % monoazo-pigment calcium salt 5 % 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 mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts of water is added.
  • the mixture is agitated until the polymerization reaction is completed.
  • the obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent.
  • the capsule suspension formulation contains 28% of the active ingredients.
  • the medium capsule diameter is 8-15 microns.
  • the resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.
  • Example 1 This example illustrates the preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy- phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X.01 of Table T1)
  • Step 1 Preparation of 3-bromo-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-imidazo[1,2-a]pyridine-6- carboxamide
  • 4-fluoro-3-methoxy-N-methyl-aniline 0.712 g, 4.36 mmol
  • N-ethyl-N-isopropyl-propan-2-amine (1.88 g, 2.49 mL
  • the reaction mixture was stirred for 1 hour at 50 °C. The mixture was then poured into ice water, and then extracted with ethyl acetate. The combined organic layers were washed with saturated NaHCO3 aq. and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was treated with diisopropylether and a precipitation occurred. The precipitate was filtered and washed with diisopropylether to afford 3-bromo-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-imidazo[1,2-a]pyridine-6- carboxamide as a white solid.
  • Step 2 Preparation of N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3- yl]-2-pyridyl]carbamate (Compound X.01) A mixture of 3-bromo-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide (0.809 g, 2.14 mmol, 1equiv.), methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl- carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (0.877 g, 3.00 mmol, 1.4 equiv.) and cesium carbonate (1.045 g, 3.21 mmol, 1.5 equiv.) in water (4.3) and
  • Tetrakis(triphenylphosphine)palladium(0) (0.127 g, 0.107 mmol, 0.05 equiv.) was then added and the reaction mixture was heated under microwave irradiation at 100 °C for 1 hour. The reaction mixture was cooled down to room temperature and then water was added. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure.
  • Example 2 This example illustrates the preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy- phenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X.02 of Table T1)
  • Step 1 Preparation of methyl 6-amino-5-chloro-pyridine-3-carboxylate To an ice-cooled solution of methyl 6-aminopyridine-3-carboxylate (5.00 g, 32.9 mmol) in tetrahydrofuran (20.0 mL) was added N-chlorosuccinimide (4.39 g, 32.9 mmol, 1.00 equiv.).
  • Step 2 Preparation of methyl 8-chloroimidazo[1,2-a]pyridine-6-carboxylate
  • methyl 6-amino-5-chloro-pyridine-3-carboxylate (4.50 g, 21.7 mmol) in ethanol (90.0 mL) was added 2-chloroacetaldehyde (17.0 g, 109 mmol, 5.00 equiv.) at room temperature.
  • the reaction mixture was stirred at 80 oC for 16 hours.
  • the reaction mixture was then cooled, concentrated under reduced pressure, and the resulting concentrated solution was poured into a cold solution of saturated sodium carbonate and stirred for an additional 5 min.
  • Step 3 Preparation of 8-chloro-N-(4-fluoro-3-methoxy-phenyl)imidazo[1,2-a]pyridine-6-carboxamide
  • methyl 8-chloroimidazo[1,2-a]pyridine-6-carboxylate (0.500 g, 2.14 mmol) and 4- fluoro-3-methoxy-aniline (0.377 g, 2.67 mmol, 1.25 equiv.) in dry toluene (20.0 mL) under a nitrogen atmosphere was added trimethylaluminium (2 mol/L, 3.20 mL, 6.41 mmol, 3.00 equiv.).
  • the resulting mixture was stirred at 100 oC for 6 hours and then cooled to 0 oC.
  • the reaction mixture was quenched with a saturated aqueous solution of sodium sulfite, methanol was added, and the mixture further diluted with ethyl acetate.
  • the reaction mixture was filtered through a pad of celite, the filtrate was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure.
  • Step 4 Preparation of N-(4-fluoro-3-methoxy-phenyl)-8-methyl-imidazo[1,2-a]pyridine-6-carboxamide
  • 8-chloro-N-(4-fluoro-3-methoxy-phenyl)imidazo[1,2-a]pyridine-6-carboxamide 2.8 g, 7.88 mmol, 1.00 equiv.
  • methylboronic acid 0.963 g, 15.8 mmol, 2.00 equiv.
  • tetrahydrofuran 50.0 mL
  • potassium carbonate 2.78g, 19.7 mmol, 2.50 equiv.
  • the reaction mixture was flushed with argon for 5 min, and chloro(2-dicyclohexylphosphino- 2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-
  • Iodomethane (0.395 mL, 6.35 mmol, 2.00 equiv.) was then added dropwise and the resulting mixture was stirred at room temperature for 3 hours.
  • the mixture was diluted with ethyl acetate and treated with a saturated solution of ammonium chloride.
  • the desired material was extracted with ethyl acetate, the combined organic layers were washed with water, brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure.
  • Step 6 Preparation of N-(4-fluoro-3-methoxy-phenyl)-3-iodo-N,8-dimethyl-imidazo[1,2-a]pyridine-6- carboxamide
  • N-(4-fluoro-3-methoxy-phenyl)-N,8-dimethyl-imidazo[1,2-a]pyridine-6- carboxamide 95.0 %, 80.0 mg, 0.243 mmol, 1.00equiv.) in dimethylformamide (2.00 mL) was added N-iodosuccinimide (66 mg, 0.29 mmol, 1.2 equiv.) and the resulting mixture was stirred at room temperature for 3 hours.
  • Step 7 Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-8-methyl- imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate
  • the mixture was purged with a stream of argon for 2 minutes after which cataCXium® A Pd G3 (48.2 mg, 0.0649 mmol, 0.05 equiv.) was added.
  • the resulting reaction mixture was irradiated under microwave irradiation at 100 oC for 1 hour. After cooling down to room temperature, the reaction mixture was filtered through a pad of celite. The filtrate was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure.
  • Example 3 This example illustrates the preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy- phenyl)-(methoxymethyl)carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X.03 of Table T1)
  • Step 1 Preparation of N-(4-fluoro-3-methoxy-phenyl)-N-(methoxymethyl)-8-methyl-imidazo[1,2- a]pyridine-6-carboxamide
  • N-(4-fluoro-3-methoxy-phenyl)-8-methyl-imidazo[1,2-a]pyridine-6- carboxamide (1.00 g, 3.01 mmol, 1.00 equiv.) in dry tetrahydrofuran (20.0 mL) was added sodium hydride (60% in oil, 0.361 g, 15.0 mmol, 5.00 e
  • Step 2 Preparation of N-(4-fluoro-3-methoxy-phenyl)-3-iodo-N-(methoxymethyl)-8-methyl-imidazo[1,2- a]pyridine-6-carboxamide
  • N-(4-fluoro-3-methoxy-phenyl)-N-(methoxymethyl)-8-methyl-imidazo[1,2-a]pyridine-6- carboxamide 300 mg, 0.786 mmol, 1.00equiv.
  • dimethylformamide 2.00 mL
  • N- iodosuccinimide 195 mg, 0.865 mmol, 1.10 equiv.
  • Step 3 Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-(methoxymethyl)carbamoyl]-8- methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate
  • the mixture was purged with a stream of argon for 2 minutes after which cataCXium® A Pd G3 (0.140 g, 0.192 mmol, 0.05 equiv.) was added.
  • the resulting mixture was heated under microwave irradiation at 100 oC for 1 hour.
  • the reaction mixture was filtered through a Celite pad and washed with ethyl acetate. The filtrate was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure.
  • Example 4 This example illustrates the preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy- phenyl)-(methoxymethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X.04 of Table T1)
  • Step 1 Preparation of N-(4-fluoro-3-methoxy-phenyl)imidazo[1,2-a]pyridine-6-carboxamide
  • 4-fluoro-3-methoxy-aniline (2.74 g, 19.4 mmol, 1.20 equiv.
  • the resulting reaction mixture was stirred at 80 oC for 3 hours.
  • the reaction mixture was cooled to 0 oC, quenched with aqueous Rochelle's salt, filtered through a Celite pad and washed with ethyl acetate.
  • the filtrate was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure.
  • the crude residue was purified over a silica gel cartridge (cyclohexane / ethyl acetate) to afford N-(4-fluoro-3-methoxy-phenyl)imidazo[1,2-a]pyridine-6-carboxamide as a white solid.
  • Step 2 Preparation of N-(4-fluoro-3-methoxy-phenyl)-N-(methoxymethyl)imidazo[1,2-a]pyridine-6- carboxamide
  • N-(4-fluoro-3-methoxy-phenyl)imidazo[1,2-a]pyridine-6-carboxamide 2.3 g, 7.66 mmol, 1.00 equiv.
  • sodium hydride 60% in oil, 0.919 g, 23.0 mmol, 3.00 eq).
  • chloro(methoxy)methane (1.3 g, 15.3 mmol, 2.00 equiv.) was added and the reaction mixture was stirred for 30 minutes at 0°C and then warmed up. After completion, the mixture was cooled down, diluted with ethyl acetate, and treated with crushed ice. The aqueous phase was extracted with ethyl acetate, the combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure.
  • Step 3 Preparation of N-(4-fluoro-3-methoxy-phenyl)-3-iodo-N-(methoxymethyl)imidazo[1,2- a]pyridine-6-carboxamide
  • N-(4-fluoro-3-methoxy-phenyl)-N-(methoxymethyl)imidazo[1,2-a]pyridine-6- carboxamide 2.4 g, 6.9 mmol, 1.0 equiv.
  • dimethylformamide 40.0 mL
  • N-iodosuccinimide (1.75 g, 7.62 mmol, 1.10 equiv.
  • Step 4 Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)- (methoxymethyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (Compound X.04) To a solution of N-(4-fluoro-3-methoxy-phenyl)-3-iodo-N-(methoxymethyl)imidazo[1,2-a]pyridine-6- carboxamide (0.600 g, 1.25 mmol, 1.00 equiv.) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-2-pyridyl]carbamate (0.426 g, 1.50 mmol, 1.20 equiv.) in 1,4-dioxane/ water (3/1, 16.0 mL) was added cesium carbonate (0.833 g, 2.50
  • the mixture was then purged with a stream of argon for 2 minutes and cataCXium® A Pd G3 (46.5 mg, 0.0626 mmol, 0.05 equiv.) was added.
  • the resulting reaction mixture was heated under microwave irradiation at 100 oC for 1 hour. After cooling down to room temperature, the mixture was filtered through a celite pad and washed with ethyl acetate. The filtrate was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure.
  • Example 5 This example illustrates the preparation of methyl N-[4-[6-[(4-fluoro-3-methoxy- phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate (compound X.05 of Table T1)
  • Step 1 Preparation of methyl N-[4-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2- a]pyridin-3-yl]phenyl]carbamate (Compound X.05) To a mixture of 3-bromo-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-imidazo[1,2-a]pyridine-6- carboxamide (0.425 g, 1.12 mmol, 1.00 equiv.), methyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-
  • the suspension was purged with a stream of argon by three freeze-pump-thaw cycles and heated under microwave irration at 100 °C for 60 minutes. After cooling down to room temperature, the mixture was filtered through a celite pad. The filtrate was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified over a silica gel cartridge (cyclohexane / ethyl acetate) to afford methyl N-[4-[6-[(4-fluoro-3-methoxy-phenyl)-methyl- carbamoyl]imidazo[1,2-a]pyridin-3-yl]phenyl]carbamate.
  • Example 6 This example illustrates the preparation of 3-[6-(cyclopropanecarbonylamino)-3- pyridyl]-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide (compound X.06 of Table T1)
  • Step 1 Preparation of N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2- pyridyl]cyclopropanecarboxamide
  • 2-aminopyridine-5-boronic acid pinacolester (1.00 g, 4.32 mmol, 1.00 equiv.
  • pyridine (1.42 mL, 17.3 mmol, 4.00 equiv.
  • ethyl acetate (40 mL) at 10 °C was added, dropwise, cyclopropanecarbonyl chloride (1.40 g, 13.0 mmol, 3
  • reaction mixture was slowly warmed to room temperature and stirred until full conversion.
  • the mixture was then diluted with ethyl acetate and treated with a saturated solution of sodium bicarbonate.
  • the aqueous phase was extracted with ethyl acetate, the combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford N-[5-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-2-pyridyl]cyclopropanecarboxamide as a white solid.
  • the crude material was used in the next step without further purification.
  • Step 2 Preparation of 3-[6-(cyclopropanecarbonylamino)-3-pyridyl]-N-(4-fluoro-3-methoxy-phenyl)-N- methyl-imidazo[1,2-a]pyridine-6-carboxamide
  • Compound X.06 A mixture of 3-bromo-N-(4-fluoro-3-methoxy-phenyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide (0.200 g, 0.513 mmol, 1.00 equiv.), N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2- pyridyl]cyclopropanecarboxamide (0,222 g, 0,769 mmol, 1.50 equiv.) and sodium carbonate (0.163 g, 1.54 mmol, 3.00 equiv.) in a
  • Example 7 This example illustrates the preparation of methyl N-[5-[6-[ethyl-(4- fluorophenyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X.19 of Table T1)
  • Step 1 Preparation of 6-bromo-3-iodo-imidazo[1,2-a]pyridine To a solution of 6-bromoimidazo[1,2-a]pyridine (2.00 g, 10.0 mmol) in acetonitrile (41 mL) was added N-iodosuccinimide (2.3 g, 10 mmol, 1.0 equiv.).
  • reaction mixture was stirred at 80 °C for 48 hours.
  • the reaction mixture was filtered off.
  • the solid was washed with 2-methyltetrahydrofuran and water, then dried under reduced pressure to afford methyl N- [5-(6-bromoimidazo[1,2-a]pyridin-3-yl)-2-pyridyl]carbamate.
  • Step 3 Preparation of methyl N-[5-[6-[ethyl-(4-fluorophenyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2- pyridyl]carbamate (compound X.19) (Compound X.19) To a solution of methyl N-[5-(6-bromoimidazo[1,2-a]pyridin-3-yl)-2-pyridyl]carbamate (0.175 g, 0.479 mmol) in toluene (1.20 mL) under argon were added N-ethyl-4-fluoro-aniline (0.078 mL, 0.60 mmol, 1.3 equiv.) followed by XantPhos Pd G3 (CAS 1445085-97-1) (0.0239 g, 0.0239 mmol, 0.0500 equiv.) and triethylamine (0.0974 g, 0.958
  • the vial was flushed with nitrogen, then filled with CO gas and pressurized with CO gas to 10 bar.
  • the vessel was heated to 110 °C for 18 hours.
  • the reaction mixture was then concentrated under reduced pressure.
  • the residue was purified by flash chromatography over silica gel (eluting with cyclohexane/ethyl acetate/ethanol) to afford methyl N-[5-[6- [ethyl-(4-fluorophenyl)carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate as a brown oil.
  • Example 8 This example illustrates the preparation of methyl N-[5-[8-acetamido-6-[(4-fluoro-3- methoxy-phenyl)-methyl-carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X.20 of Table T1)
  • Step 1 Preparation of 6-bromoimidazo[1,2-a]pyridin-8-amine Chloroacetaldehyde (50% in water) (0.84 mL, 6.6 mmol, 1.25 equiv.) was added to a solution of 5- bromopyridine-2,3-diamine (1.00 g, 5.32 mmol) in ethanol (21 mL).
  • the vial was flushed with nitrogen, then filled with CO gas and pressurized with CO gas to 10 bar.
  • the vessel was heated to 110 °C for 6 hours.
  • the reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure.
  • the residue was purified by flash chromatography over silica gel (eluting cyclohexane/ethyl acetate) to afford 8-acetamido-N-(4-fluoro-3-methoxy-phenyl)-N-methyl- imidazo[1,2-a]pyridine-6-carboxamide as a brown solid.
  • Step 5 Preparation of methyl N-[5-[8-acetamido-6-[(4-fluoro-3-methoxy-phenyl)-methyl- carbamoyl]imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X.20)
  • Compound X.20 8-acetamido-N-(4-fluoro-3-methoxy-phenyl)-3-iodo-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide (0.360 g, 0.747 mmol) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2- pyridyl]carbamate (0.311 g, 1.12 mmol, 1.50 equiv.) were dissolved in acetonitrile (5.97 mL).
  • Example 9 This example illustrates the preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy- phenyl)-methyl-carbamoyl]-8-(methoxymethyl)imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X.21 of Table T1)
  • Step 1 Preparation of methyl 6-bromoimidazo[1,2-a]pyridine-8-carboxylate
  • Chloroacetaldehyde (50% in water) (11.0 mL, 86.5 mmol, 2 equiv.) was added to a solution of methyl 2- amino-5-bromo-pyridine-3-carboxylate (10.00 g, 43.3 mmol) in ethanol (173 mL).
  • the resulting solution was stirred at 100 °C for 9 hours and then at 55 °C for 12 hours.
  • the reaction mixture was cooled down and diluted with saturated aqueous sodium bicarbonate solution.
  • the aqueous layer was extracted with ethyl acetate.
  • the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford methyl 6-bromoimidazo[1,2-a]pyridine-8- carboxylate.
  • Step 2 Preparation of (6-bromoimidazo[1,2-a]pyridin-8-yl)methanol To a mixture of calcium chloride (12.0 g, 110 mmol, 10.0 equiv) and sodium borohydride (4.20 g, 110 mmol, 10.0 equiv) in tetrahdrofuran (150 mL) was added a mixture of methyl 6-bromoimidazo[1,2- a]pyridine-8-carboxylate (3.70 g, 11.0 mmol) in tetrahydrofuran at 0 °C. Then the mixture was stirred at room temperature for 16 hours.
  • reaction mixture was cooled down to 0 °C, and diluted with saturated aqueous ammonium chloride solution.
  • the aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford (6-bromoimidazo[1,2-a]pyridin-8-yl)methanol as an off-white solid.
  • Step 4 Preparation of N-(4-fluoro-3-methoxy-phenyl)-8-(methoxymethyl)-N-methyl-imidazo[1,2- a]pyridine-6-carboxamide Bis(benzonitrile)palladium chloride (73.7 mg, 0.183 mmol, 0.10 equiv.) and 4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene (108 mg, 0.183 mmol, 0.10 equiv) were added to a mixture of 6-bromo-8- (methoxymethyl)imidazo[1,2-a]pyridine (440 mg, 1.825 mmol), 4-fluoro-3-methoxy-N-methyl-aniline (297 mg, 1.92 mmol, 1.05 equiv.) and triethylamine (0.38 mL, 2.7 mmol, 1.5 equiv.) in toluene (4.6 mL).
  • the vial was flushed with nitrogen, then filled with CO gas and pressurized with CO gas to 10 bar.
  • the vessel was heated to 110 °C for 6 hours.
  • the reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure.
  • the residue was purified by flash chromatography over silica gel (eluting cyclohexane/ethyl acetate) to afford N-(4-fluoro-3-methoxy-phenyl)-8-(methoxymethyl)-N- methyl-imidazo[1,2-a]pyridine-6-carboxamide as a brown solid.
  • Step 5 Preparation of N-(4-fluoro-3-methoxy-phenyl)-3-iodo-8-(methoxymethyl)-N-methyl-imidazo[1,2- a]pyridine-6-carboxamide N-(4-fluoro-3-methoxy-phenyl)-8-(methoxymethyl)-N-methyl-imidazo[1,2-a]pyridine-6-carboxamide (0.560 g, 1.63 mmol) was added to a solution of N-iodosuccinimide (0.374 g, 1.63 mmol, 1.00 equiv.) in acetonitrile (6.5 mL). the mixture was stirred at room temperature for one hour.
  • Step 6 Preparation of methyl N-[5-[6-[(4-fluoro-3-methoxy-phenyl)-methyl-carbamoyl]-8- (methoxymethyl)imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate
  • Compound X.21 Compound X.21
  • N-(4-fluoro-3-methoxy-phenyl)-3-iodo-8-(methoxymethyl)-N-methyl-imidazo[1,2-a]pyridine-6- carboxamide (100 mg, 0.213 mmol) and methyl N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2- pyridyl]carbamate 88.9 mg, 0.320 mmol, 1.50 equiv.
  • Example 10 This example illustrates the preparation of methyl N-[5-[6-[(2-methoxy-4-pyridyl)- methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X.22 of Table T1)
  • Step 1 Preparation of methyl 8-methylimidazo[1,2-a]pyridine-6-carboxylate A pressure reactor was charged with 6-bromo-8-methyl-imidazo[1,2-a]pyridine (CAS 217435-65-9) (12.0 g, 56.9 mmol), methanol (200.0 mL), 1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (2.30 g, 2.84 mmol, 0.05 eq) and triethylamine (17.3 g, 171 mmol, 3.00 eq.).
  • the reactor was then flushed with nitrogen, then carbon monoxide, sealed, and pressurized to 2.5 MPa with carbon monoxide.
  • the reaction was stirred at 100 °C for 8 hours.
  • the vessel was then cooled to room temperature and the pressure released.
  • the reaction mixture was concentrated under reduced pressure.
  • the residue was purified by flash chromatography over silica gel (eluting dichloromethane/methanol) to obtain methyl 8-methylimidazo[1,2-a]pyridine-6-carboxylate as a light brown solid.
  • Step 2 Preparation of methyl 3-bromo-8-methyl-imidazo[1,2-a]pyridine-6-carboxylate
  • methyl 8-methylimidazo[1,2-a]pyridine-6-carboxylate (1.70 g, 8.94 mmol) in dimethylformamide (20 mL) was added at room temperature N-bromosuccinimide (1.91 g, 10.7 mmol, 1.2 eq).
  • the reaction mixture was stirred for 2 hours at room temperature.
  • the reaction mixture was diluted with water.
  • the precipitate was collected by filtration, washed with water and dried under reduced pressure to afford methyl 3-bromo-8-methyl-imidazo[1,2-a]pyridine-6-carboxylate as a brown solid.
  • Example 11 This example illustrates the preparation of methyl N-[5-[6-[(4-cyano-3-methoxy- phenyl)-methyl-carbamoyl]-8-methyl-imidazo[1,2-a]pyridin-3-yl]-2-pyridyl]carbamate (compound X.23 of Table T1)
  • Step 1 Preparation of 3-bromo-N-(4-cyano-3-methoxy-phenyl)-8-methyl-imidazo[1,2-a]pyridine-6- carboxamide
  • 4-amino-2-methoxy-benzonitrile 0.550 g, 3.71 mmol
  • 3-bromo-8-methyl- imidazo[1,2a]pyridine-6-carboxylic acid (1.04 g, 4.08 mmol, 1.1 eq) in pyridine (15.0 mL) at 0 °C was added dropwise phosphoryl trichloride (1.71 g, 11.1 mmol, 3.0
  • reaction mixture was stirred at 75 °C for 2 hours.
  • the reaction mixture was then diluted with water and extracted with ethyl acetate.
  • the combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure.
  • the residue was purified by flash chromatography over silica gel (eluting petroleum ether/ethyl acetate) to afford 3-bromo-N-(4-cyano-3- methoxy-phenyl)-N,8-dimethyl-imidazo[1,2-a]pyridine-6-carboxamide as a yellow solid.
  • LC/MS Liquid Chromatography Mass Spectrometry and the description of the apparatus and the method is as follows: The LC/MS apparatus and method: Method A: 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.
  • Method B Spectra were recorded on a ACQUITY Mass Spectrometer from Waters Corporations (SQD or SQDII Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.0 kV, Cone: 30V, Extractor: 3.00 V, Source Temperature: 150°C, Desolvation Temperature: 400°C, Cone Gas Flow: 60 L/hr, Desolvation Gas Flow: 700 L/hr, Mass range: 140 to 800 Da) and an ACQUITY UPLC from Waters Corporations with solvent degasser, binary pump, heated column compartment and diode-array detector.
  • an electrospray source Polarity: positive or negative ions, Capillary: 3.0 kV, Cone: 30V, Extractor: 3.00 V, Source Temperature: 150°C, Desolvation Temperature: 400°C, Cone Gas Flow: 60 L/hr, Desolvation Gas Flow: 700 L/h
  • Method C Spectra were recorded on a Mass Spectrometer from Waters (Acquity QDa Mass Spectrometer) equipped with an electrospray source (Polarity: Positive and Negative Polarity Switch), Capillary: 0.8 kV, Cone range: 25 V, Extractor: V (No extractor voltage for QDa detector) 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: Quaternary solvent manager, heated column compartment , diode-array detector.
  • Method D Equipment: Shimadzu LCMS 2020 Mass Spectrometer; Column: HALO C 1 82.7 ⁇ m, 3.0 mm ⁇ 30 mm; Mobile Phase: MeCN (with either 0.05% HCOOH or 0.05% TFA) - Water (with either 0.05% HCOOH or 0.05% TFA); Gradient: MeCN from 5% to 95% over 1.4 min, hold 0.6 min, total run time is 2.5 min; Flow rate: 1.8 mL/min; Column temperature: 50 °C; Wavelength: 214 and 254 nm PDA.
  • Table T1 gathers for compounds of formula X.01 to X.23 according to formula (I): - LC/MS data, such as retention time (RT), [M+H] + , - the type of method, and/or - melting point (MP).
  • Table T1 MP °C 208 - 210 od MP °C 160 - 165 90 - 95 208 - 210 106 - 108 105 - 110 d MP °C 140 - 145 180 - 185 d MP °C 218 - 220 216 - 218 178 - 180 167 - 169 197 - 199 BIOLOGICAL EXAMPLES: General examples of leaf disk tests in well plates: Leaf disks or leaf segments of various plant species are cut from plants grown in a greenhouse. The cut leaf disks or segments are placed in multiwell plates (24-well format) onto water agar. The leaf disks are sprayed with a test solution before (preventative) or after (curative) inoculation.
  • DMSO solutions of the test compound (max.10 mg/ml) are diluted with 0.025% Tween20 by a factor of 50 and 10 ⁇ l of this solution is pipetted into a microtiter plate (96-well format). The nutrient broth containing the fungal spores/mycelia fragments is then added to give an end concentration of the tested compound. The test plates are incubated in the dark at 24°C and 96% relative humidity. The inhibition of fungal growth is determined photometrically after 2 to 7 days, depending on the pathosystem, and percent antifungal activity relative to the untreated check is calculated.
  • Example A1 Activity against Phytophthora infestans / tomato / leaf disc preventative (late blight) Tomato leaf disks are placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf disks are incubated at 16 °C and 75% 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 disks (5 - 7 days after application).
  • the following compounds gave at least 80% control of Phytophthora infestans at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: X.01, X.02, X.03, X.04, X.05, X.06, X.07, X.08, X.09, X.10, X.11, X.12, X.13, X.14, X.15, X.16, X.17, X.18, X.19, X.20, X.21, X.22, and X.23.
  • Example A2 Activity against Plasmopara viticola / grape / leaf disc preventative (late blight) Grape vine leaf disks are placed on water agar in multiwell plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf disks are inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf disks are incubated at 19 °C and 80% rh under a light regime of 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 disks (6 - 8 days after application).
  • the following compounds gave at least 80% control of Plasmopara viticola at 200 ppm when compared to untreated control under the same conditions, which showed extensive disease development: X.01, X.02, X.03, X.04, X.05, X.06, X.07, X.08, X.09, X.10, X.11, X.12, X.13, X.14, X.15, X.18, X.19, X.20, X.21, X.22, and X.23.
  • Example A3 Activity against Pythium ultimum / liquid culture (seedling damping off) Mycelia fragments and oospores of a newly grown liquid culture of the fungus 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 mycelia/spore mixture is added. The test plates are incubated at 24 °C and the inhibition of growth is determined photometrically 2-3 days after application.
  • DMSO DMSO
  • the following compounds gave at least 80% control of Pythium ultimum at 20 ppm when compared to untreated control under the same conditions, which showed extensive disease development: X.01, X.02, X.03, X.04, X.05, X.06, X.07, X.08, X.09, X.10, X.11, X.12, X.13, X.14, X.15, X.16, X.17, X.18, X.19, X.20, X.21, X.22, and X.23.
  • Streptomyces chrestomyceticus CBS149411 (used as Component B) are as follows: - Fermentation of Streptomyces sp.: Streptomyces sp. Saigon413, isolated in Vietnam before 1961, was deposited at the Westerdijk institute under accession number CBS149411. The deposit was made by Syngenta Ltd., Jealott’s Hill Research International Centre, Bracknell, Berkshire, RG426EY, UK under the terms of the Budapest Treaty on the International Recognition of the Deposit of Microorganisms for the Purposes of Patent Procedure.
  • the Streptomyces was cultivated in Erlenmeyer flasks with a liquid medium consisting of (g / l) casein hydrolysate 10, glucose 40, K2HPO41.25, soytone 2, tryptone, 8 and incubated at 28oC in an incubator shaking 150 rpm with 25 mm throw for 4 days.
  • a liquid medium consisting of (g / l) casein hydrolysate 10, glucose 40, K2HPO41.25, soytone 2, tryptone, 8 and incubated at 28oC in an incubator shaking 150 rpm with 25 mm throw for 4 days.
  • Large scale fermentations For large scale production, standard procedures were applied for cultivating Streptomyces chrestomyceticus CBS149411 to high cell density using fed-batch fermentation. After harvesting, the broth was spray dried or freeze dried according to methods known to a person skilled in the art.
  • TGAI The final product (TGAI) after spray- or freeze drying had a cell count of 1*10 5 to 1*10 13 CFU/g dry mass.
  • TGAI technical grade active ingredient (unformulated product).
  • Example B1 Activity against Pythium ultimum (Damping off) Mycelial fragments of the pathogen, prepared from a fresh liquid culture, were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. 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 80% disease control in this test.
  • Example B2 Activity against Phytophthora capsici (vegetable blight) Sporangia of the pathogen, harvested from a fresh culture grown on artificial media were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the sporangia was added. 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 80% disease control in this test.
  • DMSO DMSO
  • Example B3 Activity against Phytophthora infestans (late blight of potato/tomato) Sporangia of the pathogen from cryogenic storage were directly mixed into nutrient broth (pea medium). After placing a (DMSO) solution of the test compounds into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24 °C and the inhibition of growth was determined photometrically after 5 days. The following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 80% disease control in this test.
  • DMSO DMSO
  • Example B4 Activity against Phytophthora infestans (late blight of potato/tomato): Tomato leaf disks are placed on water agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with a spore suspension of the pathogen. After appropriate incubation the activity of a compound is assessed 4 dpi (days after inoculation) as preventive fungicidal activity. The following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 80% disease control in this test.
  • Example B5 Activity against Plasmopara viticola (downy mildew of grapevine) Grape vine leaf disks are placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf disks are inoculated with a spore suspension of the pathogen. After appropriate incubation the activity of a compound is assessed 7 dpi (days after inoculation) as preventive fungicidal activity. The following mixture compositions (A:B) at the reported concentration (in ppm) gave at least 80% disease control in this test. X.02 Cyclobutrifluram 3:1 60:20

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne une composition fongicide comprenant les 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 ou prévenir l'infestation de plantes par des micro-organismes phytopathogènes, de préférence des champignons.
PCT/EP2024/060005 2023-04-13 2024-04-12 Compositions fongicides WO2024213720A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP23167798 2023-04-13
EP23167798.0 2023-04-13

Publications (1)

Publication Number Publication Date
WO2024213720A1 true WO2024213720A1 (fr) 2024-10-17

Family

ID=86007248

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2024/060005 WO2024213720A1 (fr) 2023-04-13 2024-04-12 Compositions fongicides

Country Status (1)

Country Link
WO (1) WO2024213720A1 (fr)

Citations (64)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0353191A2 (fr) 1988-07-29 1990-01-31 Ciba-Geigy Ag Séquences d'ADN codant des polypeptides avec activité béta-1,3-glucanase
EP0367474A1 (fr) 1988-11-01 1990-05-09 Mycogen Corporation Souche de bacillus thuringiensis appelée b.t. ps81gg, active contre les lépidoptères nuisibles et gène codant une toxine active contre les lépidoptères.
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
EP0392225A2 (fr) 1989-03-24 1990-10-17 Ciba-Geigy Ag Plantes transgéniques résistantes aux maladies
WO1990013651A1 (fr) 1989-05-09 1990-11-15 Imperial Chemical Industries Plc Genes bacteriens
EP0401979A2 (fr) 1989-05-18 1990-12-12 Mycogen Corporation Souches de bacillus thuringiensis actives contre les lépidoptères nuisibles, et gènes codant pour des toxines actives contre les lépidoptères
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
US5061495A (en) 1988-03-07 1991-10-29 Agricultural Genetics Company Limited Antibiotic derived from b. subtilis
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
WO1995033818A2 (fr) 1994-06-08 1995-12-14 Ciba-Geigy Ag Genes pour la synthese des substances antipathogenes
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
WO1997033890A1 (fr) 1996-03-11 1997-09-18 Novartis Ag Derives de pyrimidine-4-one utilises comme pesticide
JPH11253151A (ja) 1997-11-13 1999-09-21 Kumiai Chem Ind Co Ltd イネの育苗時病害防除剤
US6060051A (en) 1997-05-09 2000-05-09 Agraquest, Inc. Strain of bacillus for controlling plant diseases and corn rootworm
US6245551B1 (en) 1999-03-30 2001-06-12 Agraquest, Inc. Strain of Bacillus pumilus for controlling plant diseases caused by fungi
WO2002015701A2 (fr) 2000-08-25 2002-02-28 Syngenta Participations Ag Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis)
EP1229028A1 (fr) * 1996-06-28 2002-08-07 Dow AgroSciences LLC N-Acétonylbenzamides hétérocycliques et leur utilisation comme fongicides
WO2003000051A2 (fr) 2001-06-22 2003-01-03 Drahos David J Nouveau biofongicide
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
US7094592B2 (en) 2001-11-26 2006-08-22 Kumiai Chemical Industry Co., Ltd. Bacillus sp. D747 strain, plant disease controlling agents and insect pest controlling agents using the same and control method using the agents
US7579183B1 (en) 2006-12-01 2009-08-25 The United States Of America As Represented By The Secretary Of Agriculture Saprophytic yeast, Pichia anomala
WO2009116106A1 (fr) 2008-03-21 2009-09-24 Trentino Sviluppo S.P.A. Trichoderma atroviride sc1 pour la lutte biologique contre les maladies fongiques des végétaux
WO2010086790A1 (fr) 2009-01-27 2010-08-05 Lesaffre Et Compagnie Souches de saccharomyces cerevisiae a aptitudes phytosanitaires
US20100291039A1 (en) 2007-12-14 2010-11-18 Kohl Jurgen Anton Novel micro-organisms controlling plant pathogens
WO2011138281A2 (fr) 2010-05-06 2011-11-10 Bayer Cropscience Ag Procédé de production de dithiine-tétracarboxy-diimides
WO2011151819A2 (fr) 2010-06-01 2011-12-08 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Pseudozyma aphidis en tant qu'agent de biocontrôle contre différents pathogènes de plantes
WO2013032693A2 (fr) 2011-08-27 2013-03-07 Marrone Bio Innovations, Inc. Souche bactérienne isolée du gène burkholderia et métabolites pesticides dérivés de cette souche, formulations et utilisations
WO2013034938A2 (fr) 2011-09-08 2013-03-14 Szegedi Tudományegyetem Souche de bacillus mojavensis produisant de la fengycine résistante au cuivre pour réguler les pathogènes des légumes, utilisations de cette souche et composition la contenant
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
WO2014028521A1 (fr) 2012-08-14 2014-02-20 Marrone Bio Innovations, Inc. Souche de bacillus sp. avec activité antifongique, antibactérienne et de stimulation de la croissance
WO2014078813A1 (fr) * 2012-11-19 2014-05-22 Irm Llc Composés et compositions pour le traitement de maladies parasitaires
WO2014095675A1 (fr) 2012-12-19 2014-06-26 Bayer Cropscience Ag Utilisation de carboxamides difluorométhyl-nicotinique-indanyle comme fongicides
WO2015067800A1 (fr) 2013-11-11 2015-05-14 Basf Se Souches de penicillium antifongiques, extrolites fongicides de celles-ci, et leur utilisation
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
WO2016020371A1 (fr) 2014-08-04 2016-02-11 Basf Se Souches de paenibacillus anti-fongiques, composés de type fusaricidine et leur utilisation
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
WO2017019448A1 (fr) 2015-07-24 2017-02-02 AgBiome, Inc. Agents de lutte biologique modifiés et leurs utilisations
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
WO2017055469A1 (fr) 2015-10-02 2017-04-06 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017055473A1 (fr) 2015-10-02 2017-04-06 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017066094A1 (fr) 2015-10-12 2017-04-20 Pioneer Hi-Bred International, Inc. Produits biologiques et leur utilisation dans des plantes
WO2017093348A1 (fr) 2015-12-02 2017-06-08 Syngenta Participations Ag Dérivés d'oxadiazole 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
WO2017205258A1 (fr) 2016-05-26 2017-11-30 Novozymes Bioag A/S Bacillus et lipo-chito-oligosaccharide pour améliorer la croissance de plantes
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
WO2018202428A1 (fr) 2017-05-02 2018-11-08 Basf Se Mélange fongicide comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués
WO2018228896A1 (fr) 2017-06-14 2018-12-20 Syngenta Participations Ag Compositions fongicides
WO2019110427A1 (fr) 2017-12-04 2019-06-13 Syngenta Participations Ag Dérivés de phénylamidine microbiocides
WO2020056090A1 (fr) 2018-09-14 2020-03-19 Fmc Corporation Halométhyl cétones et hydrates fongicides
WO2020079111A1 (fr) 2018-10-18 2020-04-23 Syngenta Crop Protection Ag Composés microbiocides
WO2020097012A1 (fr) 2018-11-06 2020-05-14 Fmc Corporation Tolyles substitués utilisés en tant que fongicides
WO2020109391A1 (fr) 2018-11-28 2020-06-04 Bayer Aktiengesellschaft Pyridazine (thio)amides servant de composés fongicides
WO2020193387A1 (fr) 2019-03-22 2020-10-01 Syngenta Crop Protection Ag Composés fongicides
WO2023061838A1 (fr) * 2021-10-14 2023-04-20 Syngenta Crop Protection Ag Dérivés d'imidazo[1,2-a]pyridine
WO2024126404A1 (fr) * 2022-12-14 2024-06-20 Syngenta Crop Protection Ag Dérivés d'imidazo[1,2-a]pyridine

Patent Citations (65)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
US5061495A (en) 1988-03-07 1991-10-29 Agricultural Genetics Company Limited Antibiotic derived from b. subtilis
EP0353191A2 (fr) 1988-07-29 1990-01-31 Ciba-Geigy Ag Séquences d'ADN codant des polypeptides avec activité béta-1,3-glucanase
EP0367474A1 (fr) 1988-11-01 1990-05-09 Mycogen Corporation Souche de bacillus thuringiensis appelée b.t. ps81gg, active contre les lépidoptères nuisibles et gène codant une toxine active contre les lépidoptères.
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
EP0392225A2 (fr) 1989-03-24 1990-10-17 Ciba-Geigy Ag Plantes transgéniques résistantes aux maladies
WO1990013651A1 (fr) 1989-05-09 1990-11-15 Imperial Chemical Industries Plc Genes bacteriens
EP0401979A2 (fr) 1989-05-18 1990-12-12 Mycogen Corporation Souches de bacillus thuringiensis actives contre les lépidoptères nuisibles, et gènes codant pour des toxines actives contre les lépidoptères
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
WO1995033818A2 (fr) 1994-06-08 1995-12-14 Ciba-Geigy Ag Genes pour la synthese des substances antipathogenes
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
WO1997033890A1 (fr) 1996-03-11 1997-09-18 Novartis Ag Derives de pyrimidine-4-one utilises comme pesticide
EP1229028A1 (fr) * 1996-06-28 2002-08-07 Dow AgroSciences LLC N-Acétonylbenzamides hétérocycliques et leur utilisation comme fongicides
US6060051A (en) 1997-05-09 2000-05-09 Agraquest, Inc. Strain of bacillus for controlling plant diseases and corn rootworm
JPH11253151A (ja) 1997-11-13 1999-09-21 Kumiai Chem Ind Co Ltd イネの育苗時病害防除剤
US6245551B1 (en) 1999-03-30 2001-06-12 Agraquest, Inc. Strain of Bacillus pumilus for controlling plant diseases caused by fungi
WO2002015701A2 (fr) 2000-08-25 2002-02-28 Syngenta Participations Ag Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis)
WO2003000051A2 (fr) 2001-06-22 2003-01-03 Drahos David J Nouveau biofongicide
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
US7094592B2 (en) 2001-11-26 2006-08-22 Kumiai Chemical Industry Co., Ltd. Bacillus sp. D747 strain, plant disease controlling agents and insect pest controlling agents using the same and control method using the agents
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
US7579183B1 (en) 2006-12-01 2009-08-25 The United States Of America As Represented By The Secretary Of Agriculture Saprophytic yeast, Pichia anomala
US20100291039A1 (en) 2007-12-14 2010-11-18 Kohl Jurgen Anton Novel micro-organisms controlling plant pathogens
US8431120B2 (en) 2008-03-21 2013-04-30 Trentino Sviluppo S.P.A. Trichoderma atroviride SC1 for biocontrol of fungal diseases in plants
WO2009116106A1 (fr) 2008-03-21 2009-09-24 Trentino Sviluppo S.P.A. Trichoderma atroviride sc1 pour la lutte biologique contre les maladies fongiques des végétaux
WO2010086790A1 (fr) 2009-01-27 2010-08-05 Lesaffre Et Compagnie Souches de saccharomyces cerevisiae a aptitudes phytosanitaires
WO2011138281A2 (fr) 2010-05-06 2011-11-10 Bayer Cropscience Ag Procédé de production de dithiine-tétracarboxy-diimides
WO2011151819A2 (fr) 2010-06-01 2011-12-08 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Pseudozyma aphidis en tant qu'agent de biocontrôle contre différents pathogènes de plantes
WO2013032693A2 (fr) 2011-08-27 2013-03-07 Marrone Bio Innovations, Inc. Souche bactérienne isolée du gène burkholderia et métabolites pesticides dérivés de cette souche, formulations et utilisations
WO2013034938A2 (fr) 2011-09-08 2013-03-14 Szegedi Tudományegyetem Souche de bacillus mojavensis produisant de la fengycine résistante au cuivre pour réguler les pathogènes des légumes, utilisations de cette souche et composition la contenant
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
WO2014028521A1 (fr) 2012-08-14 2014-02-20 Marrone Bio Innovations, Inc. Souche de bacillus sp. avec activité antifongique, antibactérienne et de stimulation de la croissance
WO2014078813A1 (fr) * 2012-11-19 2014-05-22 Irm Llc Composés et compositions pour le traitement de maladies parasitaires
WO2014095675A1 (fr) 2012-12-19 2014-06-26 Bayer Cropscience Ag Utilisation de carboxamides difluorométhyl-nicotinique-indanyle comme fongicides
WO2015067800A1 (fr) 2013-11-11 2015-05-14 Basf Se Souches de penicillium antifongiques, extrolites fongicides de celles-ci, et leur utilisation
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
WO2016020371A1 (fr) 2014-08-04 2016-02-11 Basf Se Souches de paenibacillus anti-fongiques, composés de type fusaricidine et leur utilisation
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
WO2017019448A1 (fr) 2015-07-24 2017-02-02 AgBiome, Inc. Agents de lutte biologique modifiés et leurs utilisations
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
WO2017055469A1 (fr) 2015-10-02 2017-04-06 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017055473A1 (fr) 2015-10-02 2017-04-06 Syngenta Participations Ag Dérivés d'oxadiazole microbiocides
WO2017066094A1 (fr) 2015-10-12 2017-04-20 Pioneer Hi-Bred International, Inc. Produits biologiques et leur utilisation dans des plantes
WO2017093348A1 (fr) 2015-12-02 2017-06-08 Syngenta Participations Ag Dérivés d'oxadiazole 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
WO2017205258A1 (fr) 2016-05-26 2017-11-30 Novozymes Bioag A/S Bacillus et lipo-chito-oligosaccharide pour améliorer la croissance de plantes
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
WO2018202428A1 (fr) 2017-05-02 2018-11-08 Basf Se Mélange fongicide comprenant des 3-phényl-5-(trifluorométhyl)-1,2,4-oxadiazoles substitués
WO2018228896A1 (fr) 2017-06-14 2018-12-20 Syngenta Participations Ag Compositions fongicides
WO2019110427A1 (fr) 2017-12-04 2019-06-13 Syngenta Participations Ag Dérivés de phénylamidine microbiocides
WO2020056090A1 (fr) 2018-09-14 2020-03-19 Fmc Corporation Halométhyl cétones et hydrates fongicides
WO2020079111A1 (fr) 2018-10-18 2020-04-23 Syngenta Crop Protection Ag Composés microbiocides
WO2020097012A1 (fr) 2018-11-06 2020-05-14 Fmc Corporation Tolyles substitués utilisés en tant que fongicides
WO2020109391A1 (fr) 2018-11-28 2020-06-04 Bayer Aktiengesellschaft Pyridazine (thio)amides servant de composés fongicides
WO2020193387A1 (fr) 2019-03-22 2020-10-01 Syngenta Crop Protection Ag Composés fongicides
WO2023061838A1 (fr) * 2021-10-14 2023-04-20 Syngenta Crop Protection Ag Dérivés d'imidazo[1,2-a]pyridine
WO2024126404A1 (fr) * 2022-12-14 2024-06-20 Syngenta Crop Protection Ag Dérivés d'imidazo[1,2-a]pyridine

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
"The Pesticide Manual", 2021, BRITISH CROP PROTECTION COUNCIL
CAN JOUR PLANT SCI, vol. 83, no. 3, 2003, pages 519 - 524
CROP PROTECTION, vol. 25, no. 2643947-26-4, 2006, pages 468 - 475
JENSEN DF ET AL.: "Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain 'IK726", AUSTRALASIAN PLANT PATHOL., vol. 36, no. 2, 2007, pages 95 - 101
PIETR ET AL., ZESZ. NAUK. A R W SZCZECINIE, vol. 161, 1993, pages 125 - 137
WEINREB, S. M ET AL., TETRAHEDRON LETT, vol. 48, 1977, pages 4171
WOODWARD S ET AL., ORG. PROCESS RES. DEV, vol. 19, 2015, pages 831
WOODWARD, S ET AL., TETRAHEDRON LETTERS, vol. 47, 2006, pages 5767

Similar Documents

Publication Publication Date Title
WO2023061838A1 (fr) Dérivés d&#39;imidazo[1,2-a]pyridine
WO2020208096A1 (fr) Compositions fongicides
CA3169015A1 (fr) Compositions fongicides
WO2024126404A1 (fr) Dérivés d&#39;imidazo[1,2-a]pyridine
US20240334934A1 (en) Fungicide mixture
WO2021244951A9 (fr) Compositions fongicides
WO2024213720A1 (fr) Compositions fongicides
WO2024213650A1 (fr) Dérivés d&#39;imidazo[1,2-a]pyridine
WO2024213651A1 (fr) Dérivés d&#39;imidazo[1,2-a]pyridine
WO2025021537A1 (fr) Dérivés de benzimidazole
WO2024213659A1 (fr) Dérivés d&#39;imidazo[1,2-a]pyrazine
WO2024213664A1 (fr) Dérivés bicycliques imidazo
WO2024213653A1 (fr) Dérivés d&#39;imidazo[1,2-a]pyridine
WO2024213663A1 (fr) Dérivés de pyrazolo[1,5-a]pyridine
WO2024126407A1 (fr) Dérivés benzimidazoles
WO2024213656A1 (fr) Dérivés d&#39;imidazo[1,2-a]pyrazine
WO2024213662A1 (fr) Dérivés de pyrazolo[1,5-a]pyridine
WO2024068838A1 (fr) Compositions fongicides
WO2024017788A1 (fr) Forme solide d&#39;un dérivé d&#39;amide hétérocyclique
US20230131427A1 (en) Fungicidal compositions
US20240306639A1 (en) Use of fluazifop-p-butyl for insect control
US20230098569A1 (en) Methods of controlling or preventing infestation of plants by the phytopathogenic microorganism corynespora cassiicola
EP4117438A1 (fr) Procédés de lutte ou de prévention de l&#39;infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola
EP4117435A1 (fr) Procédés pour lutter contre ou prévenir l&#39;infestation de plantes par le micro-organisme phytopathogène corynespora cassiicola
EP4161273A1 (fr) Compositions fongicides

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24721532

Country of ref document: EP

Kind code of ref document: A1