WO2019162228A1 - Dérivés de 1-(imidazol-1-yl à substitution en position 5)but-3-ène et leur utilisation en tant que fongicides - Google Patents

Dérivés de 1-(imidazol-1-yl à substitution en position 5)but-3-ène et leur utilisation en tant que fongicides Download PDF

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WO2019162228A1
WO2019162228A1 PCT/EP2019/053952 EP2019053952W WO2019162228A1 WO 2019162228 A1 WO2019162228 A1 WO 2019162228A1 EP 2019053952 W EP2019053952 W EP 2019053952W WO 2019162228 A1 WO2019162228 A1 WO 2019162228A1
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alkyl
cycloalkyl
halogen
substituted
methyl
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PCT/EP2019/053952
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English (en)
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Robert Alan WEBSTER
Andreas GÖRTZ
Ruth Meissner
Sybille Lamprecht
Ricarda MILLER
David Bernier
Pierre-Yves Coqueron
Pierre Genix
Stephane Brunet
Philippe Kennel
Dominique Loque
Vincent Thomas
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Bayer Aktiengesellschaft
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Publication of WO2019162228A1 publication Critical patent/WO2019162228A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/68—Halogen atoms

Definitions

  • the present invention relates to novel l-(5-substituted imidazol-l-yl)but-3-en derivatives, preferably l-(5- substituted imidazol-l-yl)but-3-en-2-ol derivatives, to processes for preparing these compounds, to compositions comprising those, and to the use thereof as biologically active compounds and compositions, especially for control of harmful microorganisms in crop protection and in the protection of materials.
  • object of the invention is to serve this need by providing novel compounds useful for control of harmful microorganisms in crop protection and in the protection of materials, in particular compounds showing fungicidal efficacy.
  • R 1 represents hydrogen, Ci-Cs-alkyl, C2-Cs-alkenyl, C2-Cs-alkynyl, C3-Cs-cycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl, Ci-Cs-alkoxy, Ci-Cs-alkylthio, C6-Ci4-aryl, C6-Ci4-aryl-Ci-C4-alkyl, Ce-Cu- aryl-C2-C4-alkenyl or C6-Ci4-aryl-C2-C4-alkynyl, wherein the aliphatic moieties, excluding cycloalkyl moieties, of R 1 may carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R a which independently of one another are selected from halogen, CN, nitro, Ci-C4-alkoxy and Ci-C rhaloalkoxy, and wherein the cycloalky
  • R 2 represents hydrogen, halogen, cyano or -OR 2a , wherein
  • R 2a represents hydrogen, Ci-C -alkyl, -Si(R 6a )(R 6b )(R 6c ), -P(0)(0H) 3 ⁇ 4 -CH 2 -0-P(0)(0H) 2 , -C(0)- Ci-Cs-alkyl, -C(0)-C 3 -C 7 -cycloalkyl, -C(0)NH-Ci-Cs-alkyl, -C(0)N-di-Ci-Cs-alkyl, or - C(0)0-Ci-C 8 -alkyl, wherein the -C(0)-Ci-C 8 -alkyl, -C(0)-C 3 -C 7 -cycloalkyl, -C(0)NH-Ci- Cs-alkyl, -C(0)N-di-Ci-Cs-alkyl and -C(0)0-Ci-Cs-alkyl is non-substituted or substituted by one or more group(s
  • R 6a , R 613 , R 6C represent independently from each other phenyl or Ci-Cs-alkyl
  • R 3 represents halogen, hydroxyl, cyano, isocyano, amino, sulfanyl, pcntafluoro-/’-sulfanyl, carboxaldehyde, hydroxycarbonyl, C 2 -Cs-alkyl, Ci-Cs-haloalkyl, Ci-Cs-cyanoalkyl, Ci-Cs-alkyloxy, Ci-C 8 -haloalkyloxy, tri(Ci-C 8 -alkyl)silyl, tri(Ci-C 8 -alkyl)silyl-Ci-C 8 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 - halocycloalkyl, C 3 -C 7 -cycloalkenyl, C 3 -C 7 -halocycloalkenyl, C4-Cio-cycloalkylalkyl, C4-C10- halocycloal
  • R 5 represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-haloalkyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-Cs- alkylthio or Ci-Cs-haloalkylthio;
  • Q represents a 6-membered aromatic cycle of formula (Q-I)
  • U 1 represents CX 1 or N
  • U 2 represents CX 2 or N
  • U 3 represents CX 3 or N
  • U 4 represents CX 4 or N
  • U 5 represents CX 5 or N; wherein X 1 , X 2 , X 3 , X 4 , and X 5 independently from each other represent hydrogen, halogen, nitro, cyano, sulfanyl, pentafluoro ⁇ 6 -sulfanyl, Ci-Cs-alkyl, Ci-Cs-haloalkyl having 1 to 5 halogen atoms, C 3 -Cs-cycloalkyl, C 3 -Cs-halocycloalkyl having 1 to 5 halogen atoms, Ci-Cs- haloalkyl-C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkenyl, C 2 -Cs-alkenyl, C 2 -Cs-alkynyl, C 6 -C 12 - bicycloalkyl, C 3 -C 8 -cycloalkyl-C 2 -Cs-alkenyl, C 3
  • U 1 and U 2 or U 2 and U 3 or U 3 and U 4 form together an additional saturated or unsaturated 4 to 6-membered halogen- or Ci -CValkyl-substitutcd or non-substituted ring; and its salts and N-oxides.
  • R 1 preferably represents Ci-Cs-alkyl, C 3 -Cs-cycloalkyl, C 6 -Ci 4 -aryl or C 6 -Ci 4 -aryl-Ci-C 4 -alkyl, wherein the aliphatic moieties, excluding cycloalkyl moieties, of R 1 may carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R a which independently of one another are selected from halogen, CN, nitro, Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy; and wherein the cycloalkyl and/or aryl moieties of R 1 may carry 1, 2, 3, 4, 5 or up to the maximum number of identical or different groups R b which independently of one another are selected from halogen, CN, nitro, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy.
  • R 1 more preferably represents Ci-Cs-alkyl, Ci-Cs-haloalkyl, C3-Cs-cycloalkyl, C6-Ci4-aryl or Ce-Cu- aryl-Ci-C4-alkyl, wherein the cycloalkyl and/or aryl moieties of R 1 may carry 1 or 2 identical or different groups R b which independently of one another are selected from halogen, CN, nitro, C 1 -C 4 - alkyl, Ci-C4-alkoxy, Ci-C4-haloalkyl and Ci-C4-haloalkoxy.
  • R 1 more preferably represents optionally halogen-, or Ci-C4-alkyl-substituted C3-C7-cycloalkyl, optionally halogen-, or Ci-C4-alkyl-substituted phenyl or optionally halogen-, or Ci-C4-alkyl- substituted benzyl.
  • R 1 more preferably represents optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, h-butyl-, isobutyl-, or fert-butyl-substituted C3-C6-cycloalkyl, optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, h-butyl-, isobutyl-, or tert- butyl- substituted phenyl or optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, h-propyl-, isopropyl-, h-butyl-, isobutyl-, or /er/-butyl-substituted benzyl.
  • R 1 more preferably represents optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, h-butyl-, isobutyl-, or fer/-butyl-substituted cyclopropyl, optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, h-propyl-, isopropyl-, h-butyl-, isobutyl-, or fer/-butyl-substituted phenyl or optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, h-butyl-, isobutyl- , or ter/-butyl-substituted benzyl.
  • R 1 more preferably represents cyclopropyl, 1-fluorocyclopropyl, 1-chlorocyclopropyl, 1- bromocyclopropyl, 1-methylcyclopropyl, 1 -ethylcyclopropyl, optionally fluorine-, chlorine-, or bromine-substituted phenyl or optionally fluorine-, chlorine-, or bromine-substituted benzyl.
  • R 1 more preferably represents cyclopropyl, 1-fluorocyclopropyl, 1-chlorocyclopropyl, 1- bromocyclopropyl, 1-methylcyclopropyl, 1 -ethylcyclopropyl, phenyl, fluorine-substituted phenyl, benzyl or fluorine-substituted benzyl.
  • R 1 more preferably represents cyclopropyl, 1-fluorocyclopropyl, 1-chlorocyclopropyl, 1- bromocyclopropyl, 1-methylcyclopropyl, 1 -ethylcyclopropyl, phenyl, 2-fluorophenyl, 3- fluorophenyl, 4-fluorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6- difluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 2- fluoro-6-chlorophenyl, 2-chloro-3 -fluorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-fluorophenyl or benzyl.
  • R 1 most preferably represents l-fluorocycloprop
  • R 2 preferably represents hydrogen, fluorine, chlorine, cyano or -OR 2a .
  • R 2 more preferably represents -OR 2a .
  • R 2a preferably represents H, Ci-Cs-alkyl, or halogen- or Ci-Cs-alkoxy-substituted or non-substituted - C(0)-Ci-C 8 -alkyl.
  • R 2a more preferably represents H or Ci-Cs-alkyl.
  • R 2a more preferably represents H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl.
  • R 2a most preferably represents H.
  • R 2 most preferably represents -OH.
  • R 3 preferably represents halogen, hydroxyl, cyano, isocyano, nitro, carboxaldehyde, hydroxycarbonyl, Ci-Cs-alkyl, Ci-Cs-haloalkyl, Ci-Cs-cyanoalkyl, Ci-Cs-alkyloxy, Ci-Cs-haloalkyloxy, C 3 -C 7 - cycloalkyl, C 3 -C 7 -halocycloalkyl, C 2 -Cs-alkenyl, C 2 -Cs-alkynyl, C 2 -Cs-alkenyloxy, C 2 -C 8 - haloalkenyloxy, C 3 -Cs-alkynyloxy, Ci-Cs-halooalkynyloxy, Ci-Cs-alkylsulfanyl, Ci-Cs- haloalkylsulfanyl, Ci-Cs-alkylcarbonyl, Ci-Cs-
  • R 3 more preferably represents halogen, cyano, nitro, carboxaldehyde, hydroxycarbonyl, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -cyanoatkyl, Ci-C 4 -alkyloxy, Ci-C 4 -haloalkyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halocycloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -atkynyl, Ci-C 4 -atkylsulfanyl, Ci-C 4 -haloalkylsulfanyl, C 1 -C 4 - alkylcarbonyl, Ci-C 4 -haloalkylcarbonyl, aminothiocarbonyl, carbamoyl, Ci-C 4 -alkoxycarbonyl or Ci-C 4 -halogenoalkoxycarbonyl.
  • R 3 more preferably represents fluorine, chlorine, bromine, iodine, cyano, aminothiocarbonyl or C1-C4- haloalkyl.
  • R 3 more preferably represents fluorine, chlorine, bromine, iodine, cyano, aminothiocarbonyl, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, l-chloroethyl, 1- bromoethyl, l-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or l, l,l-trifluoroprop-2-yl.
  • R 3 more preferably represents fluorine, cyano or CF 3 .
  • R 3 most preferably represents cyano or CF 3 .
  • R 4 preferably represents hydrogen, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or fer/-butyl.
  • R 4 more preferably represents hydrogen, fluorine, methyl or ethyl.
  • R 4 more preferably represents hydrogen, fluorine or methyl.
  • R 4 more preferably represents hydrogen or methyl.
  • R 5 preferably represents hydrogen, fluorine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or fer/-butyl.
  • R 5 more preferably represents hydrogen, fluorine, methyl or ethyl.
  • R 5 more preferably represents hydrogen, fluorine or methyl.
  • R 5 more preferably represents hydrogen or methyl.
  • R 4 and R 5 represents hydrogen and the other one represents hydrogen or methyl.
  • Q preferably represents a substituted 6-membered aromatic heterocycle containing one or two nitrogen atoms or a substituted 6-membered aromatic carbocycle. Substituted meaning that the cycle of the given formula comprises at least one of X 1 , X 2 , X 3 , X 4 or X 5 not being hydrogen. More preferably represents a, preferably substituted, 6-membered aromatic cycle of formula (Q-I-l) to (Q-I-10)
  • X 1 , X 2 , X 3 , X 4 and X 5 have the same definition as given for formula (I) above. Preferred definitions of X 1 , X 2 , X 3 , X 4 and X 5 are given below. More preferably represents a, preferably substituted, phenyl, 3-pyridyl or 4-pyridyl of formula (Q-I- 1) to (Q-I-3)
  • X 1 , X 2 , X 3 , X 4 and X 5 have the same definition as given for formula (I) above. Preferred definitions of X 1 , X 2 , X 3 , X 4 and X 5 are given below. More preferably represents a, preferably substituted, phenyl or 3-pyridyl of formula (Q-I-l) or (Q-I-
  • X 1 , X 2 , X 3 , X 4 and X 5 have the same definition as given for formula (I) above. Preferred definitions of X 1 , X 2 , X 3 , X 4 and X 5 are given below.
  • Q most preferably represents a, preferably substituted, phenyl of formula (Q-I-l)
  • X 1 , X 2 , X 3 , X 4 and X 5 have the same definition as given for formula (I) above. Preferred definitions of X 1 , X 2 , X 3 , X 4 and X 5 are given below.
  • X 1 , X 2 , X 3 , X 4 , and X 5 independently from each other preferably represent hydrogen, halogen, nitro, cyano, sulfanyl, pentafluoro ⁇ 6 -sulfanyl, Ci-Cs-alkyl, Ci-Cs-haloalkyl having 1 to 5 halogen atoms, C 3 -C 8 - cycloalkyl, Cs-Cs-halocycloalkyl having 1 to 5 halogen atoms, Ci-Cs-haloalkyl-C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkenyl, C 2 -Cs-alkenyl, C 2 -Cs-alkynyl, Ce-Cn-bicycloatkyl, C 3 -Cs-cycloalkyl-C 2 -C 8 - alkenyl, C 3 -C 8 -cycloalkyl-C
  • X 1 , X 2 , X 3 , X 4 and X 5 independently from each other more preferably represent hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-haloalkyl having 1 to 5 halogen atoms, C 2 -Cs-alkenyl, C 2 -Cs-alkynyl, C 3 -C 8 - cycloalkyl-C 2 -C 8 -alkenyl, C 3 -C 8 -cycloalkyl-C 2 -C 8 -alkynyl, Ci-Cx-alkoxy, Ci-Cx-haloalkoxy having 1 to 5 halogen atoms, C 6 -Ci 4 -aryl, or C 6 -Ci 4 -aryloxy, wherein the C 6 -Ci 4 -aryl and C 6 -Ci 4 -aryloxy is non-substituted or substituted by one or more group(s) selected
  • X 1 , X 2 , X 3 , X 4 and X 5 independently from each other more preferably represent hydrogen, fluorine, chlorine, bromine, cyano, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl having 1 to 5 halogen atoms, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl-C 2 -C 4 -alkenyl, C 3 -C 6 -cycloalkyl-C 2 -C 4 -alkynyl, Ci-C 4 -alkoxy, Ci- C 4 -haloalkoxy having 1 to 5 halogen atoms, phenyl, or phenyloxy, wherein the phenyl and phenyloxy is non-substituted or substituted by one or more group(s) selected from fluorine, chlorine, bromine, Ci-C 4 -alky
  • X 1 , X 2 , X 3 , X 4 and X 5 independently from each other more preferably represent hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, fer/-butyl, CF 3 , vinyl, cyclopropyl-C 2 -C 4 -alkynyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert- butoxy, OCF 3 , phenyl, or phenyloxy, wherein the phenyl and phenyloxy is non-substituted or substituted by one or more group(s) selected from fluorine, chlorine, bromine, methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, fer/-but
  • X 1 , X 2 , X 3 , X 4 and X 5 independently from each other more preferably represent hydrogen, fluorine, chlorine, bromine, cyano, methyl, CF 3 , vinyl, cyclopropyl-ethynyl, methoxy, OCF 3 , phenyl, or phenyloxy, wherein the phenyl and phenyloxy is non-substituted or substituted by one or more group(s) selected from fluorine, and chlorine.
  • X 1 , X 2 , X 3 , X 4 , and X 5 independently from each other more preferably represent hydrogen, fluorine, chlorine, or bromine.
  • X 1 , X 2 , X 3 , X 4 , and X 5 independently from each other more preferably represent hydrogen, fluorine, or chlorine.
  • X 1 most preferably represents hydrogen, fluorine or chlorine.
  • X 2 most preferably represents hydrogen, fluorine or chlorine.
  • X 3 more preferably represents hydrogen, fluorine or chlorine, most preferably hydrogen or chlorine.
  • X 4 more preferably represents hydrogen, fluorine or chlorine, most preferably hydrogen or fluorine.
  • X 5 more preferably represents hydrogen, fluorine or chlorine, most preferably hydrogen.
  • the radical definitions and explanations given above in general terms or stated within preferred ranges can be combined with one another as desired, i.e. including between the particular ranges and preferred ranges. They apply both to the end products and correspondingly to educts and intermediates. In addition, individual definitions may not apply. Preference is given to those cases in which each of the radicals have the abovementioned preferred definitions.
  • R 1 represents optionally halogen-, or Ci-C 4 -alkyl-substituted C 3 -C 7 -cycloalkyl, optionally halogen-, or Ci-C 4 -alkyl-substituted phenyl or optionally halogen-, or Ci-C 4 -alkyl-substituted benzyl;
  • R 2 represents -OH
  • R 3 represents cyano or CF3
  • R 4 represents hydrogen or methyl
  • R 5 represents hydrogen or methyl
  • Q represents a 6-membered aromatic cycle of formula (Q-I-l) or (Q-I-2)
  • X 1 , X 2 , X 3 , X 4 , and X 5 independently from each other represent hydrogen, halogen, cyano, Ci-Cs- alkyl, Ci-Cs-haloalkyl having 1 to 5 halogen atoms, C 2 -Cs-alkenyl, C 2 -Cs-alkynyl, Cs-Cs-cycloalkyl- C 2 -C 8 -alkenyl, C 3 -Cs-cycloalkyl-C 2 -C 8 -alkynyl, Ci-Cs-alkoxy, Ci-Cx-haloalkoxy having 1 to 5 halogen atoms, C 6 -Ci 4 -aryl, or C 6 -Ci 4 -aryloxy, wherein the C 6 -Ci 4 -aryl and C 6 -Ci 4 -aryloxy is non- substituted or substituted by one or more group(s) selected from halogen, Ci -
  • R 1 represents optionally halogen-substituted cyclopropyl, optionally halogen-substituted phenyl or optionally halogen-substituted benzyl;
  • R 2 represents -OH
  • R 3 represents cyano or CF 3 ;
  • R 4 represents hydrogen or methyl
  • R 5 represents hydrogen or methyl
  • Q represents a 6-membered aromatic cycle of formula (Q-I-l)
  • X 1 , X 2 , X 3 , X 4 , and X 5 independently from each other represent hydrogen, fluorine or chlorine; and its salts and N-oxides.
  • R 1 represents optionally halogen-substituted cyclopropyl, optionally halogen-substituted phenyl or optionally halogen-substituted benzyl, preferably cyclopropyl, l-fluorocyclopropyl, 1- chlorocyclopropyl, 1 -bromocyclopropyl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2-fluoro-3- chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 2-fluoro-6-chlorophenyl, 2-chloro- 3-fluorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5
  • R 3 represents cyano or CF 3 ;
  • Q represents a 6-membered aromatic cycle of formula (Q-I-l)
  • X 1 , X 2 , X 3 , X 4 , and X 5 independently from each other represent hydrogen, fluorine or chlorine; preferably phenyl, 2-fluorophenyl, 3 -fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2- fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 2-fluoro-6-chlorophenyl, 2-chloro-3-fluorophenyl, 2-chloro-4-fluorophenyl or 2-chloro-5-fluorophenyl, more preferred phenyl, 2-fluorophenyl, 2-chloropheny
  • R 1 represents l-fluorocyclopropyl, 1 -chlorocyclopropyl, 2,4-difluorophenyl, or benzyl;
  • R 3 represents cyano or CF 3 ; and Q represents phenyl, 2-fluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 2,3-difluorophenyl, 2,5- difluorophenyl or 2-fluoro-3-chlorophenyl, preferably phenyl, 2-fluorophenyl, or 4-chlorophenyl; and its salts and N-oxides. ln the definitions of the symbols given in the above and below formulae, collective terms were used. Unless defined elsewhere those are generally representative of the following substituents: Halogen: fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. Halogen- substitution is generally indicated by the prefix halo, halogen or halogeno.
  • Alkyl saturated, straight-chain or branched hydrocarbyl radical having 1 to 8, preferably 1 to 6, and more preferably 1 to 4 carbon atoms, for example (but not limited to) Ci-C 6 -alkyl such as methyl, ethyl, propyl (n-propyl), 1 -methylethyl (iso-propyl), butyl (n-butyl), 1 -methylpropyl (sec-butyl), 2-methylpropyl (iso butyl), l,l-dimethylethyl (tert-butyl), pentyl, l-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- dimethylpropyl, l-ethylpropyl, l,l-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1 -methylpentyl, 2- methylpentyl, 3 -methylpentyl, 4-methylpentyl,
  • Ci- C4-alkyl group e.g. a methyl, ethyl, propyl, 1 -methylethyl (isopropyl), butyl, 1 -methylpropyl (sec-butyl), 2-methylpropyl (iso-butyl) or l,l-dimethylethyl (tert-butyl) group.
  • alkyl as part of a composite substituent, for example cycloalkylalkyl, hydroxyalkyl, unless defined elsewhere like, for example, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, haloalkyl or haloalkylsulfanyl.
  • Alkenyl unsaturated, straight-chain or branched hydrocarbyl radicals having 2 to 8, preferably 2 to 6, and more preferably 2 to 4 carbon atoms and one double bond in any position, for example (but not limited to) C2-C6-alkenyl such as vinyl, allyl, (E)-2-methylvinyl, (Z)-2-methylvinyl, isopropenyl, homoallyl, (E)-but- 2-enyl, (Z)-but-2-enyl, (E)-but-l-enyl, (Z)-but-l-enyl, 2-methylprop-2-enyl, l-methylprop-2-enyl, 2- methylprop- 1 -enyl, (E)-l-methylprop-l-enyl, (Z)- 1 -methylprop- 1 -enyl, pent-4-enyl, (E)-pent-3-enyl, (Z)- pent-3-enyl, (E)-pent-2
  • Alkynyl straight-chain or branched hydrocarbyl groups having 2 to 8, preferably 2 to 6, and more preferably 2 to 4 carbon atoms and one triple bond in any position, for example (but not limited to) C2-C6- alkynyl, such as ethynyl, prop-l-ynyl, prop-2 -ynyl, but-l-ynyl, but-2-ynyl, but-3-ynyl, l-methylprop-2- ynyl, pent- 1 -ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, 2-methylbut-3-ynyl, 1 -methylbut-3-ynyl, 1- methylbut-2-ynyl, 3-methylbut-l-yn
  • said alkynyl group is ethynyl, prop-l-ynyl, or prop-2-ynyl.
  • This definition also applies to alkynyl as part of a composite substituent, for example haloalkynyl, unless defined elsewhere.
  • Alkoxy saturated, straight-chain or branched alkoxy radicals having 1 to 8, preferably 1 to 6 and more preferably 1 to 4 carbon atoms, for example (but not limited to) Ci-C 6 -alkoxy such as methoxy, ethoxy, propoxy, 1 -methylethoxy, butoxy, 1 -methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1- methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, 1,1- dimethylpropoxy, 1 ,2-dimethylpropoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4- methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-eth
  • Alkylsulfanyl saturated, straight-chain or branched alkylsulfanyl radicals having 1 to 8, preferably 1 to 6 and more preferably 1 to 4 carbon atoms, for example (but not limited to) Ci-C 6 -alkylsulfanyl such as methylsulfanyl, ethylsulfanyl, propylsulfanyl, 1 -methylethylsulfanyl, butylsulfanyl, 1 -methylpropyl- sulfanyl, 2-methylpropylsulfanyl, 1,1-dimethylethylsulfanyl, pentylsulfanyl, 1-methylbutylsulfanyl, 2- methylbutylsulfanyl, 3-methylbutylsulfanyl, 2,2-dimethylpropylsulfanyl, 1 -ethylpropylsulfanyl, 1,1- dimethylpropylsulfanyl, 1,
  • Alkylsulfinyl saturated, straight-chain or branched alkylsulfinyl radicals having 1 to 8, preferably 1 to 6 and more preferably 1 to 4 carbon atoms, for example (but not limited to) Ci-C 6 -alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, l-methylethylsulfinyl, butylsulfinyl, 1 -methylpropylsulfinyl, 2-methylpropylsulfinyl, l, l -dimethylethylsulfinyl, pentylsulfinyl, 1 -methylbutylsulfinyl, 2- methylbutylsulfinyl, 3 -methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1 -ethylpropy
  • Alkylsulfonyl saturated, straight-chain or branched alkylsulfonyl radicals having 1 to 8, preferably 1 to 6 and more preferably 1 to 4 carbon atoms, for example (but not limited to) Ci-C 6 -alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1 -methylethylsulfonyl, butylsulfonyl, 1 -methylpropyl- sulfonyl, 2-methylpropylsulfonyl, 1 , 1-dimethylethylsulfonyl, pentylsulfonyl, 1 -methylbutylsulfonyl, 2- methylbutylsulfonyl, 3 -methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1 -ethylpropyl
  • Monoalkylamino represents an amino radical having one alkyl residue with 1 to 4 carbon atoms attached to the nitrogen atom.
  • Non-limiting examples include methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino and tert-butylamino.
  • Dialkylamino represents an amino radical having two independently selected alkyl residues with 1 to 4 carbon atoms each attached to the nitrogen atom.
  • Non-limiting examples include /V, /V- d i m c t h y 1 a m i n o , /V,/V-dicthylamino, /V, /V- d i i s o p ro py 1 a m i n o , /V- c t h y 1 - /V- m c t h y 1 a m i n o , /V- m c t h y 1 - /V- n - p ro p y 1 a m i n o , /V-iso- p ro p y 1 - /V- n - p ro p
  • Cycloalkyl monocyclic, saturated hydrocarbyl groups having 3 to 10, preferably 3 to 8 and more preferably 3 to 6 carbon ring members, for example (but not limited to) cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as part of a composite substituent, for example cycloalkylalkyl, unless defined elsewhere.
  • Cycloalkenyl monocyclic, partially unsaturated hydrocarbyl groups having 3 to 10, preferably 3 to 8 and more preferably 3 to 6 carbon ring members, for example (but not limited to) cyclopropenyl, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as part of a composite substituent, for example cycloalkenylalkyl, unless defined elsewhere.
  • Cycloalkoxy monocyclic, saturated cycloalkyloxy radicals having 3 to 10, preferably 3 to 8 and more preferably 3 to 6 carbon ring members, for example (but not limited to) cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as part of a composite substituent, for example cycloalkoxyalkyl, unless defined elsewhere.
  • Haloalkyl straight-chain or branched alkyl groups having 1 to 8, preferably 1 to 6 and more preferably 1 to 4 carbon atoms (as specified above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as specified above, for example (but not limited to) Ci-C3-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1- bromoethyl, 1 -fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2- chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluor
  • Haloalkenyl and haloalkynyl are defined analogously to haloalkyl except that, instead of alkyl groups, alkenyl and alkynyl groups are present as part of the substituent.
  • Haloalkoxy straight-chain or branched alkoxy groups having 1 to 8, preferably 1 to 6 and more preferably 1 to 4 carbon atoms (as specified above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as specified above, for example (but not limited to) Ci-C3-haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloro fluoromethoxy, dichloro fluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2- fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoro
  • Haloalkylsulfanyl straight-chain or branched alkylsulfanyl groups having 1 to 8, preferably 1 to 6 and more preferably 1 to 4 carbon atoms (as specified above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as specified above, for example (but not limited to) C1-C3- haloalkylsulfanyl such as chloromethylsulfanyl, bromomethylsulfanyl, dichloromethylsulfanyl, trichloromethylsulfanyl, fluoromethylsulfanyl, difluoromethylsulfanyl, trifluoromethylsulfanyl, chlorofluoromethylsulfanyl, dichlorofluoromethylsulfanyl, chlorodifluoromethylsulfanyl, 1 -chloro- ethylsulfanyl, 1 -bromoethylsulfanyl, l-
  • Aryl mono-, bi- or tricyclic aromatic or partially aromatic group having 6 to 14 carbon atoms, for example (but not limited to) phenyl, naphthyl, tetrahydronapthyl, indenyl and indanyl.
  • the binding to the superordinate general structure can be carried out via any possible ring member of the aryl residue.
  • Aryl is preferably selected from phenyl, 1 -naphthyl and 2-naphthyl. Phenyl is particularly preferred.
  • Heteroaryl 5 or 6-membered cyclic aromatic group containing at least 1, if appropriate also 2, 3, 4 or 5 heteroatoms, wherein the heteroatoms are each selected independently of one another from the group S, N and O, and which group can also be part of a bi- or tricyclic system having up to 14 ring members, wherein the ring system can be formed with one or two further cycloalkyl, cycloalkenyl, heterocyclyl, aryl and/or heteroaryl residues and wherein benzofused 5 or 6-membered heteroaryl groups are preferred.
  • the binding to the superordinate general structure can be carried out via any possible ring member of the heteroaryl residue.
  • Examples of 5-membered heteroaryl groups which are attached to the skeleton via one of the carbon ring members are fur-2-yl, fur-3-yl, thien-2-yl, thien-3-yl, pyrrol-2-yl, pyrrol-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, imidazol-2-yl, imidazole-4-yl, l,2,4-oxadiazol-3-yl, l,2,4-
  • Examples of 5- membered heteroaryl groups which are attached to the skeleton via a nitrogen ring member are pyrrol- 1-yl, pyrazol-l-yl, 1,2,4-triazol-l-yl, imidazol-l-yl, 1,2,3-triazol-l-yl and 1,3,4-triazol-l-yl.
  • 6-membered heteroaryl groups are pyridine-2-yl, pyridine-3-yl, pyridine-4-yl, pyridazin-3- yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazine-2-yl, l,3,5-triazin-2-yl, 1,2,4- triazin-3-yl and l,2,4,5-tetrazin-3-yl.
  • Examples of benzofused 5-membered heteroaryl groups are indol-
  • Examples of benzofused 6-membered heteroaryl groups are quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5- yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-l-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl.
  • This definition also applies to heteroaryl as part of a composite substituent, for example heteroarylalkyl, unless defined elsewhere.
  • the binding to the superordinate general structure can be carried out via a ring carbon atom or, if possible, via a ring nitrogen atom of the heterocyclic group.
  • Saturated heterocyclic groups in this sense are for example (but not limited to) oxiranyl, aziridinyl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, isoxazolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5- yl, isothiazolidin-3-yl, isothiazolidin-4-yl, isothiazolidin-5-yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, oxazolidin-2-yl, oxazolidin-4-yl, oxazolidin-5-yl, thiazolidin-4-yl, thiazolidin-4-yl,
  • benzofused heterocyclic groups are indolin-l- yl, indolin-2-yl, indolin-3-yl, isoindolin-l-yl, isoindolin-2-yl, 2,3-dihydrobenzofuran-2-yl and 2,3- dihydrobenzofuran-3-yl.
  • This definition also applies to heterocyclyl as part of a composite substituent, for example heterocyclylalkyl, unless defined elsewhere.
  • Oxo represents a doubly bonded oxygen atom.
  • Thiooxo represents a doubly bonded sulfur atom.
  • Optionally substituted groups may be mono- or polysubstituted, where the substituents in the case of polysubstitutions may be identical or different.
  • Ring structures having three or more adjacent oxygen atoms, for example, are excluded.
  • the compounds of the invention may be present in the form of different stereoisomers. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the invention encompasses both pure stereoisomers and any mixture of these isomers. Where a compound can be present in two or more tautomer forms in equilibrium, reference to the compound by means of one tautomeric description is to be considered to include all tautomer forms.
  • the present invention furthermore relates to processes for preparing compounds of formula (I), including compounds of formulae (la), (lb) and (Ic).
  • Compounds (I) can be obtained by various routes, in analogy to processes known in the prior art.
  • processes formerly described for the synthesis of the corresponding 1,2,4-triazole- containing analogues see e.g. EP-A 251086 ; WO-A 1989/005581 ; EP-A 32121 1 ; WO-A 1991/012000 ; Maurin et al. Pharmaceutical Research 1993, 10(2), 309-12; International Journal of Pharmaceutics 1993, 94(1-3), 11-14 ; DE-A 4419812 and references cited therein
  • radicals Q, R 1 , R 2 , R 2a , R 3 , R 4 and R 5 have the meanings given above for the compounds of formula (I). These definitions apply not only to the end products of the formula (I) but likewise to all intermediates.
  • ketones of formula (III) which can be obtained according to formerly described processes (e.g. according to WO-A 2016/156290, in particular according to processes J to L described therein), are reacted with derivatives (II), wherein G stands for halogen or hydrogen.
  • G stands for hydrogen
  • compounds (II) [the preparation of which is largely described using e.g. reactions such as Wittig, Homer- Wadsworth-Emmons or Julia olefinations, starting from carbonyl compounds] can be reacted with metallation reagents preferably under anhydrous conditions.
  • Suitable metallation reagents can be alkylmetal reagents such as e.g.
  • organometallic intermediates are subsequently reacted with ketones (HI), preferably under anhydrous conditions to obtain compounds of the general formula (I-OH).
  • compounds (II) [which are either commercially available or can be prepared by literature-known methods, e.g. by dibromination of the corresponding styrenes followed by base- promoted elimination as described in US2009/30238 or by Piou & Rovis, J. Am. Chem. Soc. 2014, 136(32), 1 1292-11295] can be first reacted either with metals (e.g. lithium, magnesium or zinc, in an appropriate form such as metallic powder or turnings) or with alkylmetal reagents (such as e.g.
  • metals e.g. lithium, magnesium or zinc, in an appropriate form such as metallic powder or turnings
  • alkylmetal reagents such as e.g.
  • the reaction is conducted in the presence on a solvent.
  • a solvent all common solvents inert under the reaction conditions, such as for example ethers (such as e.g. diethyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran), dichloromethane, or mixtures thereof can be used and the reaction can be effected in mixtures of two or more of these solvents.
  • the reaction is preferably performed at temperatures between -78°C and refluxing temperature of the solvent, more preferably between -50°C and 25°C.
  • epoxides of formula (IV) which can be obtained according to formerly described processes (e.g. according to EP-A 251086 ; WO-A 1989/005581 ; EP-A 32121 1 ; WO- A 1991/012000 ; DE-A 4419812), are reacted with imidazoles (V) which are commercially available or can be obtained by means of methods described in the literature, optionally in the presence of a base, such as potassium carbonate and/or potassium /crt-butoxidc, optionally in the presence of a Lewis acid, such as magnesium dichloride or BF 3 /Et 2 0.
  • a base such as potassium carbonate and/or potassium /crt-butoxidc
  • organomagnesium bases such as MeMgCl, TMPMgCl or analogues may also be employed (see Org. Lett., 2016, 18 (1), pp 16-19).
  • the reaction is conducted in the presence on a solvent.
  • solvent all common solvents inert under the reaction conditions, such as for example nitriles (such as e.g. acetonitrile, propionitrile) or amides (such as e.g. DMF, DMAc or NMP) can be used and the reaction can be effected in mixtures of two or more of these solvents.
  • the reaction is preferably performed at temperatures between -78°C and refluxing temperature of the solvent, more preferably between 25°C and l50°C.
  • compounds of the general structure (I-OH) can be reacted with alkylhalides, dialkylsulfates, anhydrides, acid chlorides, phosphorylchloride, alkylisocyanate, carbamoyl chlorides, carbono chloridates or imidocarbonates, preferably in the presence of a base to obtain compounds (I), wherein R 2 is different from OH.
  • Useful reaction auxiliaries are, as appropriate, inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogencarbonates, hydrides, hydroxides or alkoxides, for example sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate or calcium hydrogencarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, n-butyllithium, sec- butyllithium, tert-butyllithium, lithium diisopropylamide, lithium bis(trimethylsilyl)amide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxid
  • Useful reaction auxiliaries are, as appropriate, inorganic or organic acids. These preferably include inorganic acids, for example hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulphuric acid, phosphoric acid and nitric acid, and acidic salts such as NaHSCU and KHSO4, or organic acids, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or diunsaturated C6-C20 fatty acids, alkylsulphuric monoesters, alkylsulphonic acids (sulphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylsulphonic acids or aryld
  • the processes A to B are optionally performed using one or more diluents.
  • Useful diluents are virtually all inert organic solvents. Unless otherwise indicated for the above described processes, these preferably include aliphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl ether, dibutyl ether and methyl tert-butyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl ketone, methyl isoprop
  • reaction temperatures can be varied within a relatively wide range.
  • the temperatures employed are between -78°C and 250°C, preferably temperatures between -78°C and 150°C.
  • the reaction time varies as a function of the scale of the reaction and of the reaction temperature, but is generally between a few minutes and 48 hours.
  • the processes are generally performed under standard pressure. However, it is also possible to work under elevated or reduced pressure.
  • the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use one of the components used in each case in a relatively large excess.
  • the compounds are optionally separated from the reaction mixture by one of the customary separation techniques. If necessary, the compounds are purified by recrystallization or chromatography.
  • salts and/or N-oxides of the starting compounds can be used.
  • the compounds of the invention may be present in the form of the free compound and/or an agriculturally acceptable salt thereof.
  • agriculturally acceptable salt refers to a salt of a compound of the invention with acids or bases which are agriculturally acceptable.
  • the compounds of formula (I) may have acidic or basic properties and can form salts, if appropriate also inner salts, or adducts with inorganic or organic acids or with bases or with metal ions. If the compounds carry amino, alkylamino or other groups which induce basic properties, these compounds can be reacted with acids to give salts, or they are directly obtained as salts in the synthesis. If the compound carries hydroxyl, carboxyl or other groups which induce acidic properties, these compounds can be reacted with bases to give salts.
  • Suitable bases are, for example, hydroxides, carbonates, bicarbonates of the alkali metals and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines having (Ci-C -alkyl groups, mono-, di- and trialkanolamines of (Ci-C4)-alkanols, choline and also chlorocholine.
  • the salts obtainable in this manner also have fungicidal properties.
  • inorganic acids examples include hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulphuric acid, phosphoric acid and nitric acid, and acidic salts, such as NaHSC and KHSO 4 .
  • Suitable organic acids are, for example, formic acid, carbonic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, maleic acid, fumaric acid, tartaric acid, sorbic acid oxalic acid, alkylsulphonic acids (sulphonic acids having straight- chain or branched alkyl radicals of 1 to 20 carbon atoms), arylsulphonic acids or aryldisulphonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two sulphonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals of 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as
  • Suitable metal ions are in particular the ions of the elements of the second main group, in particular calcium and magnesium, of the third and fourth main group, in particular aluminium, tin and lead, and also of the first to eighth transition group, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc and others. Particular preference is given to the metal ions of the elements of the fourth period.
  • the metals can be present in various valencies that they can assume.
  • the acid addition salts of the compounds of the formula (1) can be obtained in a simple manner by customary methods for forming salts, for example by dissolving a compound of the formula (1) in a suitable inert solvent and adding the acid, for example hydrochloric acid, and be isolated in a known manner, for example by filtration, and, if required, be purified by washing with an inert organic solvent.
  • Suitable anions of the salts are those which are preferably derived from the following acids: hydrohalic acids, such as, for example, hydrochloric acid and hydrobromic acid, furthermore phosphoric acid, nitric acid and sulphuric acid.
  • the metal salt complexes of compounds of the formula (1) can be obtained in a simple manner by customary processes, for example by dissolving the metal salt in alcohol, for example ethanol, and adding the solution to the compound of the formula (1).
  • Metal salt complexes can be isolated in a known manner, for example by filtration, and, if required, be purified by recrystallization.
  • Salts of the intermediates can also be prepared according to the processes mentioned above for the salts of compounds of formula (1).
  • N-oxides of compounds of the formula (1) or intermediates thereof can be obtained in a simple manner by customary processes, for example by N-oxidation with hydrogen peroxide (H2O2), peracids, for example peroxy sulfuric acid or peroxy carboxylic acids, such as meta-chloroperoxybenzoic acid or peroxymonosulfuric acid (Caro's acid).
  • H2O2 hydrogen peroxide
  • peracids for example peroxy sulfuric acid or peroxy carboxylic acids, such as meta-chloroperoxybenzoic acid or peroxymonosulfuric acid (Caro's acid).
  • the compound of the invention may exist in multiple crystalline and/or amorphous forms.
  • Crystalline forms include unsolvated crystalline forms, solvates and hydrates.
  • the present invention further relates to a composition for controlling harmful microorganisms, preferably for controlling phytopathogenic harmful fungi, comprising at least one compound of formula (1) and at least one carrier and/or surfactant.
  • the compositions may be applied to the microorganisms and/or in their habitat.
  • a carrier is a solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert.
  • the carrier generally improves the application of the compounds, for instance, to plants, plants parts or seeds.
  • suitable solid carriers include, but are not limited to, ammonium salts, natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, and synthetic rock flours, such as finely divided silica, alumina and silicates.
  • typically useful solid carriers for preparing granules include, but are not limited to crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks.
  • suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof.
  • suitable solvents include polar and nonpolar organic chemical liquids, for example from the classes of aromatic and nonaromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may optionally also be substituted, etherified and/or esterified, such as butanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (such as dimethylformamide), lactams (such as N-alkylpyrrolidones) and lactones, sulf
  • the carrier may also be a liquefied gaseous extender, i.e. liquid which is gaseous at standard temperature and under standard pressure, for example aerosol propellants such as halohydrocarbons, butane, propane, nitrogen and carbon dioxide.
  • the amount of carrier typically ranges from 1 to 99.99%, preferably from 5 to 99.9%, more preferably from 10 to 99.5%, and most preferably from 20 to 99% by weight of the composition.
  • the surfactant can be an ionic (cationic or anionic) or non-ionic surfactant, such as ionic or non-ionic emulsifier(s), foam former(s), dispersant(s), wetting agent(s) and any mixtures thereof.
  • surfactants include, but are not limited to, salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene and/or propylene oxide with fatty alcohols, fatty acids or fatty amines (polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols and derivatives of compounds containing sulfates, sulfonates, phosphates (for example, alkylsulfonates, alkyl sulfates, arylsulfonates) and protein hydroly
  • a surfactant is typically used when the compound of the invention and/or the carrier is insoluble in water and the application is made with water. Then, the amount of surfactants typically ranges from 5 to 40% by weight of the composition.
  • the composition may comprise at least one other suitable auxiliary.
  • auxiliaries include water repellents, siccatives, binders (adhesive, tackifier, fixing agent, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone and tylose), thickeners, stabilizers (e.g. cold stabilizers, preservatives, antioxidants, light stabilizers, or other agents which improve chemical and/or physical stability), dyes or pigments (such as inorganic pigments, e.g.
  • iron oxide, titanium oxide and Prussian Blue ; organic dyes, e.g. alizarin, azo and metal phthalocyanine dyes), antifoams (e.g. silicone antifoams and magnesium stearate), preservatives (e.g.
  • dichlorophene and benzyl alcohol hemiformal secondary thickeners (cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica), stickers, gibberellins and processing auxiliaries, mineral and vegetable oils, perfumes, waxes, nutrients (including trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc), protective colloids, thixotropic substances, penetrants, sequestering agents and complex formers.
  • secondary thickeners cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica
  • stickers gibberellins and processing auxiliaries
  • mineral and vegetable oils perfumes
  • waxes including trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc
  • protective colloids including trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molyb
  • auxiliaries are related to the intended mode of application of the compound of the invention and/or on the physical properties. Furthermore, the auxiliaries may be chosen to impart particular properties (technical, physical and/or biological properties) to the compositions or use forms prepared therefrom. The choice of auxiliaries may allow customizing the compositions to specific needs.
  • composition of the invention may be in any customary form, such as solutions (e.g aqueous solutions), emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural or synthetic products impregnated with the compound of the invention, fertilizers and also microencapsulations in polymeric substances.
  • solutions e.g aqueous solutions
  • emulsions e.g. aqueous solutions
  • emulsions e.g. aqueous solutions
  • emulsions e.g. aqueous solutions
  • emulsions e.g. aqueous solutions
  • emulsions e.g. aqueous solutions
  • emulsions e.g. aqueous solutions
  • emulsions e.g., wettable powders, water- and oil-based suspensions
  • composition of the invention may be provided to the end user as ready-for-use formulation, i.e. the compositions may be directly applied to the plants or seeds by a suitable device, such as a spraying or dusting device.
  • a suitable device such as a spraying or dusting device.
  • the compositions may be provided to the end user in the form of concentrates which have to be diluted, preferably with water, prior to use.
  • composition of the invention can be prepared in conventional manners, for example by mixing the compound of the invention with one or more suitable auxiliaries, such as disclosed herein above.
  • composition according to the invention contains generally from 0.01 to 99% by weight, from 0.05 to 98% by weight, preferably from 0.1 to 95% by weight, more preferably from 0.5 to 90% by weight, most preferably from 1 to 80% by weight of the compound of the invention. It is possible that a composition comprises two or more compounds of the invention. In such case the outlined ranges refer to the total amount of compounds of the present invention. Mixtures /Combinations
  • the compound and the composition of the invention can be mixed with other active ingredients like fungicides, bactericides, acaricides, nematicides, insecticides, herbicides, fertilizers, growth regulators, safeners or semiochemicals. This may allow to broaden the activity spectrum or to prevent development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides and bactericides are disclosed in the Pesticide Manual, l7th Edition.
  • Inhibitors of the ergosterol biosynthesis for example (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) Pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) t
  • Inhibitors of the respiratory chain at complex I or II for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr, (2.009) Isofetamid, (2.010) isopyrazam (anti-epimeric enantiomer lR,4S,9S), (2.01 1) isopyrazam (anti-epimeric enantiomer lS,4R,9R), (2.012) isopyrazam (anti-epimeric racemate lRS,4SR,9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate lRS,4SR,9RS and anti-epimeric racemate lRS,4SR,9SR), (2.014) isopyrazam (syn-epimeric enantiomer
  • Inhibitors of the respiratory chain at complex III for example (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2- ⁇ 2-[( ⁇ [(lE)-l-(3- ⁇ [((l
  • Inhibitors of the mitosis and cell division for example (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate- methyl, (4.008) zoxamide, (4.009) 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010)
  • Inhibitors of the amino acid and/or protein biosynthesis for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-l-yl)quinoline.
  • Inhibitors of the ATP production for example (8.001) silthiofam.
  • Inhibitors of the cell wall synthesis for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-one, (9.009) (2Z)-3- (4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)- 1 -(morpholin-4-yl)prop-2-en- 1 -one.
  • Inhibitors of the lipid and membrane synthesis for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.
  • Inhibitors of the melanin biosynthesis for example (1 1.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl ⁇ 3-methyl-l-[(4-methylbenzoyl)amino]butan-2-yl ⁇ carbamate.
  • Inhibitors of the nucleic acid synthesis for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).
  • Inhibitors of the signal transduction for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.
  • the compound and the composition of the invention may also be combined with one or more biological control agents.
  • biological control agents which may be combined with the compound and the composition of the invention are:
  • Antibacterial agents selected from the group of:
  • (Al) bacteria such as (Al. l) Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRU Accession No. B2l66land described in U.S. Patent No. 6,060,051);
  • amyloliquefaciens strain FZB24 (available as Taegro® from Novozymes, US); (A1.5) a Paenibacillus sp. strain having Accession No. NRRL B-50972 or Accession No. NRRL B-67129 and described in International Patent Publication No. WO 2016/154297; and
  • (A2) fungi such as (A2.1) Aureobasidium pullulans, in particular blastospores of strain DSM14940; (A2.2) Aureobasidium pullulans blastospores of strain DSM 14941 ; (A2.3) Aureobasidium pullulans, in particular mixtures of blastospores of strains DSM14940 and DSMl494l ;
  • (Bl) bacteria for example (B 1.1) Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B2166 land described in U.S. Patent No. 6,060,051); (B1.2) Bacillus pumilus, in particular strain QST2808 (available as SONATA® from Bayer CropScience LP, US, having Accession No. NRRL B-30087 and described in U.S. Patent No.
  • Bacillus pumilus in particular strain GB34 (available as Yield Shield® from Bayer AG, DE);
  • Bacillus amyloliquefaciens in particular strain D747 (available as Double NickelTM from Certis, US, having accession number FERM BP-8234 and disclosed in US Patent No. 7,094,592);
  • Bacillus subtilis Y1336 available as BIOBAC ® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos.
  • Bacillus amyloliquefaciens strain MBI 600 (available as SUBTILEX from BASF SE); (B1.8) Bacillus subtilis strain GB03 (available as Kodiak® from Bayer AG, DE); (B1.9) Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes Biologicals Inc., Salem, Virginia or Syngenta Crop Protection, LLC, Greensboro, North Carolina as the fungicide TAEGRO ® or TAEGRO ® ECO (EPA Registration No.
  • Bacillus mycoides, isolate J available as BmJ TGAI or WG from Certis USA
  • Bacillus licheniformis in particular strain SB3086 (available as EcoGuard TM Biofungicide and Green Releaf from Novozymes)
  • Bacillus licheniformis in particular strain SB3086 (available as EcoGuard TM Biofungicide and Green Releaf from Novozymes)
  • B1.12 a Paenibacillus sp. strain having Accession No. NRRL B-50972 or Accession No. NRRL B-67129 and described in International Patent Publication No. WO 2016/154297.
  • the biological control agent is a Bacillus subtilis or Bacillus amyloliquefaciens strain that produces a fengycin or plipastatin-type compound, an iturin-type compound, and/or a surfactin- type compound.
  • Bacillus subtilis or Bacillus amyloliquefaciens strain that produces a fengycin or plipastatin-type compound, an iturin-type compound, and/or a surfactin- type compound.
  • Bacillus strains capable of producing lipopeptides include Bacillus subtilis QST713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B21661and described in U.S. Patent No. 6,060,051), Bacillus amyloliquefaciens strain D747 (available as Double NickelTM from Certis, US, having accession number FERM BP-8234 and disclosed in US Patent No. 7,094,592); Bacillus subtilis MBI600 (available as SUBTILEX ® from Becker Underwood, US EPA Reg. No.
  • Bacillus suhtihs Y 1336 (available as BIOBAC ® WP from Bion- Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos. 4764, 5454, 5096 and 5277); Bacillus amyloliquefaciens, in particular strain FZB42 (available as RHIZOVITAL ® from ABiTEP, DE); and Bacillus subtilis var. amyloliquefaciens FZB24 (available from Novozymes Biologicals Inc., Salem, Virginia or Syngenta Crop Protection, LLC, Greensboro, North Carolina as the fungicide TAEGRO ® or TAEGRO ® ECO (EPA Registration No. 70127-5); and
  • (B2) fungi for example: (B2.1) Coniothyrium minitans, in particular strain CON/M/91-8 (Accession No. DSM-9660; e.g. Contans ® from Bayer); (B2.2) Metschnikowia fructicola, in particular strain NRRL Y- 30752 (e.g. Shemer®); (B2.3) Microsphaeropsis ochracea (e.g. Microx® from Prophyta); (B2.5) Trichoderma spp., including Trichoderma atroviride, strain SC1 described in International Application No.
  • Trichoderma atroviride from Kumiai Chemical Industry
  • Trichoderma atroviride strain CNCM 1-1237 (e.g. Esquive® WP from Agrauxine, FR);
  • Trichoderma atroviride strain no. V08/002387;
  • B2.40 Trichoderma atroviride, strain NMI no. V08/002388;
  • B2.41 Trichoderma atroviride, strain NMI no. V08/002389;
  • B2.42 Trichoderma atroviride, strain NMI no. V08/002390;
  • Trichoderma atroviride strain LC52 (e.g.
  • Trichoderma atroviride Trichoderma atroviride, strain ATCC 20476 (IMI 206040); (B2.45) Trichoderma atroviride, strain Tl l (IMI352941/ CECT20498); (B2.46) Trichoderma harmatum, (B2.47) Trichoderma harzianum, (B2.48) Trichoderma harzianum rifai T39 (e.g. Trichodex® from Makhteshim, US); (B2.49) Trichoderma harzianum, in particular, strain KD (e.g.
  • Trichoplus from Biological Control Products, SA (acquired by Becker Underwood)); (B2.50) Trichoderma harzianum, strain ITEM 908 (e.g. Trianum-P from Koppert); (B2.51) Trichoderma harzianum, strain TH35 (e.g. Root-Pro by Mycontrol); (B2.52) Trichoderma virens (also known as Gliocladium virens), in particular strain GL-21 (e.g. SoilGard 12G by Certis, US); (B2.53) Trichoderma viride, strain TVl(e.g. Trianum-P by Koppert); (B2.54) Ampelomyces quisqualis, in particular strain AQ 10 (e.g.
  • Botector® by bio-ferm, CH (B2.64) Cladosporium cladosporioides, strain H39 (by Stichting Divichting Diviching Diviching Diviching Diviching Diviching Diviching Diviching Diviching Diviching Diviching Diviching Divichoek); (B2.69) Gliocladium catenulatum (Synonym: Clonostachys rosea f catenulate) strain J1446 (e.g. Prestop ® by AgBio Inc. and also e.g. Primastop® by Kemira Agro Oy); (B2.70) Lecanicillium lecanii (formerly known as Verticillium lecanii) conidia of strain KV01 (e.g.
  • Vertalec® by Koppert/Arysta (B2.71) Penicillium vermiculatum; (B2.72) Pichia anomala, strain WRL-076 (NRRL Y-30842); (B2.75) Trichoderma atroviride, strain SKT-1 (FERM P-16510); (B2.76) Trichoderma atroviride, strain SKT-2 (FERM P-1651 1); (B2.77) Trichoderma atroviride, strain SKT-3 (FERM P-17021); (B2.78) Trichoderma gamsii (formerly I viride), strain ICC080 (IMI CC 392151 CABI, e.g. BioDerma by AGROBIOSOL DE MEXICO, S.A.
  • strain WCS850 CBS 276.92; e.g. Dutch Trig by Tree Care Innovations
  • Verticillium chlamydosporium Verticillium chlamydosporium
  • mixtures of Trichoderma asperellum strain ICC 012 and Trichoderma gamsii strain ICC 080 product known as e.g. BIO-TAMTM from Bayer CropScience LP, US).
  • biological control agents which may be combined with the compound and the composition of the invention are: bacteria selected from the group consisting of Bacillus cereus, in particular B. cereus strain CNCM 1-1562 and Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582), Bacillus subtilis strain OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), B. thuringiensis subsp.
  • Bacillus cereus in particular B. cereus strain CNCM 1-1562 and Bacillus firmus
  • strain 1-1582 accesion number CNCM 1-1582
  • Bacillus subtilis strain OST 30002 accesion No. NRRL B-50421
  • viruses selected from the group consisting of Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV, and Spodoptera littoralis (African cotton leafworm) NPV.
  • Adoxophyes orana sumr fruit tortrix
  • GV Cydia pomonella (codling moth) granulosis virus
  • NPV nuclear polyhedrosis virus
  • Spodoptera exigua beet armyworm
  • Spodoptera frugiperda fall armyworm
  • mNPV Spodoptera littoralis
  • bacteria and fungi which can be added as 'inoculanf to plants or plant parts or plant organs and which, by virtue of their particular properties, promote plant growth and plant health.
  • Examples are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suill
  • plant extracts and products formed by microorganisms including proteins and secondary metabolites which can be used as biological control agents such as Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up ( Chenopodium quinoa saponin extract), Pyrethrum/Pyrethrins, Qpassia amara, Quercus, Quillaja, Regalia, "Requiem TM Insecticide", rotenone, ?ya «za/ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brass
  • insecticides examples include insecticides, acaricides and nematicides, respectively, which could be mixed with the compound and the composition of the invention, are:
  • Acetylcholinesterase (AChE) inhibitors such as, for example, carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifo
  • GABA-gated chloride channel blockers such as, for example, cyclodiene-organochlorines, for example chlordane and endosulfan or phenylpyrazoles (fiproles), for example ethiprole and fipronil.
  • Sodium channel modulators such as, for example, pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR)-trans-isomer], deltamethrin, empenthrin [(EZ)-(lR)-i
  • Nicotinic acetylcholine receptor (nAChR) competitive modulators such as, for example, neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • neonicotinoids e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
  • Nicotinic acetylcholine receptor (nAChR) allosteric modulators such as, for example, spinosyns, e.g. spinetoram and spinosad.
  • Glutamate-gated chloride channel (GluCl) allosteric modulators such as, for example, avermectins/milbemycins, for example abamectin, emamectin benzoate, lepimectin and milbemectin.
  • Juvenile hormone mimics such as, for example, juvenile hormone analogues, e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
  • Miscellaneous non-specific (multi-site) inhibitors such as, for example, alkyl halides, e.g. methyl bromide and other alkyl halides; or chloropicrine or sulphuryl fluoride or borax or tartar emetic or methyl isocyanate generators, e.g. diazomet and metam.
  • alkyl halides e.g. methyl bromide and other alkyl halides
  • chloropicrine or sulphuryl fluoride or borax or tartar emetic or methyl isocyanate generators e.g. diazomet and metam.
  • Mite growth inhibitors such as, for example clofentezine, hexythiazox and diflovidazin or etoxazole.
  • Microbial disruptors of the insect gut membrane such as, for example Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and B.t. plant proteins: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Abl/35Abl .
  • Inhibitors of mitochondrial ATP synthase such as, ATP disruptors such as, for example, diafenthiuron or organotin compounds, for example azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon.
  • ATP disruptors such as, for example, diafenthiuron or organotin compounds, for example azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon.
  • Nicotinic acetylcholine receptor channel blockers such as, for example, bensultap, cartap hydrochloride, thiocylam, and thiosultap-sodium.
  • Inhibitors of chitin biosynthesis type 0, such as, for example, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • Inhibitors of chitin biosynthesis type 1, for example buprofezin.
  • Moulting disruptor in particular for Diptera, i.e. dipterans, such as, for example, cyromazine.
  • Ecdysone receptor agonists such as, for example, chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
  • Octopamine receptor agonists such as, for example, amitraz.
  • Mitochondrial complex III electron transport inhibitors such as, for example, hydramethylnone or acequinocyl or fluacrypyrim.
  • Mitochondrial complex I electron transport inhibitors such as, for example from the group of the METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).
  • METI acaricides e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).
  • Voltage-dependent sodium channel blockers such as, for example indoxacarb or metaflumizone.
  • Inhibitors of acetyl CoA carboxylase such as, for example, tetronic and tetramic acid derivatives, e.g. spirodiclofen, spiromesifen and spirotetramat.
  • Mitochondrial complex IV electron transport inhibitors such as, for example, phosphines, e.g. aluminium phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, e.g. calcium cyanide, potassium cyanide and sodium cyanide.
  • Mitochondrial complex II electron transport inhibitors such as, for example, Acto-kctonitrilc derivatives, e.g. cyenopyrafen and cyflumetofen and carboxanilides, such as, for example, pyflubumide.
  • Ryanodine receptor modulators such as, for example, diamides, e.g. chlorantraniliprole, cyantraniliprole and flubendiamide, further active compounds such as, for example, Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, Chloroprallethrin, Cryolite, Cyclaniliprole, Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon- Momfluthrin, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxamet
  • safeners which could be mixed with the compound and the composition of the invention are, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (- ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-( ⁇ 4-[(methylcarbamoyl)amino]phenyl ⁇ - sulphonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-l-oxa-4-azaspiro[4.5]decane (CAS 71526- 07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-l,3-oxazolidine (
  • herbicides which could be mixed with the compound and the composition of the invention are:
  • plant growth regulators are:
  • the compounds and compositions of the invention have potent microbicidal activity and/or plant defense modulating potential. They can be used for controlling unwanted microorganisms, such as unwanted fungi and bacteria. They can be particularly useful in crop protection (they control microorganisms that cause plants diseases) or for protecting materials (e.g. industrial materials, timber, storage goods) as described in more details herein below. More specifically, the compounds and compositions of the invention can be used to protect seeds, germinating seeds, emerged seedlings, plants, plant parts, fruits, harvest goods and/or the soil in which the plants grow from unwanted microorganisms.
  • the invention further relates to a method for controlling harmful microorganisms, preferably phytopathogenic harmful fungi, in crop protection and in the protection of materials, wherein at least one compound of formula (I) or a composition comprising such compound is applied to the harmful microorganisms and/or their habitat.
  • the invention further relates to the use of at least one compound of formula (I) or a composition comprising such compound for control of harmful microorganisms, preferably phytopathogenic harmful fungi, in crop protection and in the protection of materials.
  • the invention also relates to the use of at least one compound of formula (I) or a composition comprising such compound for treatment of a transgenic plant or for treatment of seed, preferably seed of a transgenic plant.
  • Control or controlling as used herein encompasses protective, curative and eradicative treatment of unwanted microorganisms.
  • Unwanted microorganisms may be pathogenic bacteria, pathogenic virus, pathogenic oomycetes or pathogenic fungi, more specifically phytopathogenic bacteria, phytopathogenic virus, phytopathogenic oomycetes or phytopathogenic fungi. As detailed herein below, these phytopathogenic microorganims are the causal agents of a broad spectrum of plants diseases.
  • the compound and the composition of the invention can be used as fungicides.
  • fungicide refers to a compound or composition that can be used in crop protection for the control of unwanted fungi, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and/or for the control of Oomycetes.
  • the compound and the composition of the invention may also be used as antibacterial agent.
  • they may be used in crop protection, for example for the control of unwanted bacteria, such as Pseudomonadaceae, Rhizobiaceae, Xanthomonadaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • the compound and the composition of the invention may also be used as antiviral agent in crop protection.
  • the compound and the composition of the invention may have effects on diseases from plant viruses, such as the tobacco mosaic vims (TMV), tobacco rattle vims, tobacco stunt vims (TStuV), tobacco leaf curl vims (VLCV), tobacco nervilia mosaic vims (TVBMV), tobacco necrotic dwarf vims (TNDV), tobacco streak vims (TSV), potato vims X (PVX), potato vimses Y, S, M, and A, potato acuba mosaic vims (PAMV), potato mop-top vims (PMTV), potato leaf-roll vims (PLRV), alfalfa mosaic vims (AMV), cucumber mosaic vims (CMV), cucumber green mottlemosaic vims (CGMMV), cucumber yellows vims (CuYV), watermelon mosaic vims (WMV), tomato spotted wilt vims (TSWV), tomato ringspot vim
  • the present invention also relates to a method for controlling unwanted microorganisms, such as unwanted fungi, oomycetes and bacteria, comprising the step of applying at least one compound of the invention or at least one composition of the invention to the microorganisms and/or their habitat (to the plants, plant parts, seeds, fruits or to the soil in which the plants grow).
  • unwanted microorganisms such as unwanted fungi, oomycetes and bacteria
  • Suitable substrates that may be used for cultivating plants include inorganic based substrates, such as mineral wool, in particular stone wool, perlite, sand or gravel; organic substrates, such as peat, pine bark or sawdust; and petroleum based substrates such as polymeric foams or plastic beads.
  • Effective and plant-compatible amount means an amount that is sufficient to control or destroy the fungi present or liable to appear on the cropland and that does not entail any appreciable symptom of phytotoxicity for said crops. Such an amount can vary within a wide range depending on the fungus to be controlled, the type of crop, the crop growth stage, the climatic conditions and the respective compound or composition of the invention used. This amount can be determined by systematic field trials that are within the capabilities of a person skilled in the art.
  • the compound and the composition of the invention may be applied to any plants or plant parts.
  • Plants mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the genetically modified plants (GMO or transgenic plants) and the plant cultivars which are protectable and non-protectable by plant breeders’ rights.
  • GMO Genetically modified plants
  • GMO Genetically modified plants
  • heterologous gene essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome. This gene gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology, RNA interference - RNAi - technology or microRNA - miRNA - technology).
  • a heterologous gene that is located in the genome is also called a transgene.
  • a transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
  • Plant cultivars are understood to mean plants which have new properties ("traits") and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.
  • Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoots, leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes.
  • the plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.
  • Plants which may be treated in accordance with the methods of the invention include the following: cotton, flax, grapevine, fruit, vegetables, such as Rosaceae sp. (for example pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and soft fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp.
  • Rosaceae sp. for example pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and soft fruits such as strawberries
  • Rosaceae sp. for example pome fruits such as apples and pears, but also
  • Rubiaceae sp. for example coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. for example lemons, oranges and grapefruit
  • Solanaceae sp. for example tomatoes
  • Liliaceae sp. Aster aceae sp.
  • Umbelliferae sp. for example lettuce
  • Umbelliferae sp. for example lettuce
  • Cicurbitaceae sp. for example cucumber
  • Alliaceae sp. for example leek, onion
  • peas for example peas
  • major crop plants such as Gramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (for example soya bean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard, beetroot); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.
  • Plants and plant cultivars which may be treated by the above disclosed methods include plants and plant cultivars which are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.
  • Plants and plant cultivars which may be treated by the above disclosed methods include those plants which are resistant to one or more abiotic stresses.
  • Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.
  • Plants and plant cultivars which may be treated by the above disclosed methods include those plants characterized by enhanced yield characteristics lncreased yield in said plants may be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation.
  • Yield may furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, intemode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance.
  • Further yield traits include seed composition, such as carbohydrate content and composition for example cotton or starch, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability.
  • Plants and plant cultivars which may be treated by the above disclosed methods include plants and plant cultivars which are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses.
  • Plants and plant cultivars obtained by plant biotechnology methods such as genetic engineering
  • plants and plant cultivars which are herbicide- tolerant plants i.e. plants made tolerant to one or more given herbicides.
  • Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.
  • Plants and plant cultivars obtained by plant biotechnology methods such as genetic engineering
  • plants and plant cultivars which are insect-resistant transgenic plants i.e. plants made resistant to attack by certain target insects.
  • Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.
  • Plants and plant cultivars obtained by plant biotechnology methods such as genetic engineering
  • plants and plant cultivars which are disease- resistant transgenic plants i.e. plants made resistant to attack by certain target insects.
  • Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.
  • Plants and plant cultivars obtained by plant biotechnology methods such as genetic engineering
  • Plants and plant cultivars which may be treated by the above disclosed methods include plants and plant cultivars which are tolerant to abiotic stresses.
  • Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance.
  • Plants and plant cultivars obtained by plant biotechnology methods such as genetic engineering which may be treated by the above disclosed methods include plants and plant cultivars which show altered quantity, quality and/or storage-stability of the harvested product and/or altered properties of specific ingredients of the harvested product.
  • Plants and plant cultivars obtained by plant biotechnology methods such as genetic engineering which may be treated by the above disclosed methods include plants and plant cultivars, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics.
  • Plants and plant cultivars obtained by plant biotechnology methods such as genetic engineering
  • plants and plant cultivars which may be treated by the above disclosed methods include plants and plant cultivars, such as oilseed rape or related Brassica plants, with altered oil profile characteristics.
  • Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered oil profile characteristics.
  • Plants and plant cultivars obtained by plant biotechnology methods such as genetic engineering which may be treated by the above disclosed methods include plants and plant cultivars, such as oilseed rape or related Brassica plants, with altered seed shattering characteristics.
  • Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered seed shattering characteristics and include plants such as oilseed rape plants with delayed or reduced seed shattering.
  • Plants and plant cultivars obtained by plant biotechnology methods such as genetic engineering which may be treated by the above disclosed methods include plants and plant cultivars, such as Tobacco plants, with altered post-translational protein modification patterns.
  • Non-limiting examples of pathogens of fungal diseases which may be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis; Podosphaera species, for example Podosphaera leucotricha; Sphaerotheca species, for example Sphaerotheca fuliginea; Uncinula species, for example Uncinula necator; diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis; Uromyces species, for example Uromyces appendiculat
  • Phytophthora species for example Phytophthora infestans ; Plasmopara species, for example Plasmopara viticola; Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example Pythium ultimum; leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, for example Colletotrichum lindemuthan
  • Pseudomonas species for example Pseudomonas syringae pv. lachrymans
  • Erwinia species for example Erwinia amylovora
  • Liberibacter species for example Liberibacter asiaticus
  • Xyella species for example Xylella fastidiosa
  • Ralstonia species for example Ralstonia solanacearum
  • Dickeya species for example Dickeya solani
  • Clavibacter species for example Clavibacter michiganensis
  • Streptomyces species for example Streptomyces scabies. diseases of soya beans:
  • Rhizoctonia solani phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot ( Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off ( Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight ( Sclerotinia rolfsii), thielaviopsis root rot ( Thielaviopsis basicola).
  • the compound and the composition of the invention may reduce the mycotoxin content in the harvested material and the foods and feeds prepared therefrom.
  • Mycotoxins include particularly, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2- toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec., such as F.
  • Penicillium spec. such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec., such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotrys spec and others.
  • the compound and the composition of the invention may also be used in the protection of materials, especially for the protection of industrial materials against attack and destruction by phytopathogenic fungi.
  • the compound and the composition of the invention may be used as antifouling compositions, alone or in combinations with other active ingredients.
  • Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry.
  • industrial materials which are to be protected from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms.
  • Parts of production plants and buildings, for example cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected.
  • Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.
  • the compound and the composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • the compound and the composition of the invention may also be used against fungal diseases liable to grow on or inside timber.
  • Timber means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood.
  • the compound and the composition of the invention may be used to protect objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, from fouling.
  • Storage goods are understood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired.
  • Storage goods of vegetable origin for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, may be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting.
  • Storage goods also include timber, both unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture.
  • Storage goods of animal origin are, for example, hides, leather, furs and hairs.
  • the compound and the composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.
  • Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms.
  • the compound and the composition of the invention preferably act against fungi, especially moulds, wood-discoloring and wood-destroying fungi ( Ascomycetes , Basidiomycetes, Deuteromycetes and Zygomycetes ), and against slime organisms and algae.
  • microorganisms of the following genera Alternaria, such as Alternaria tenuis, Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria
  • the compound and the composition of the invention may also be used to protect seeds from unwanted microorganisms, such as phytopathogenic microorganisms, for instance phytopathogenic fungi or phytopathogenic oomycetes.
  • phytopathogenic microorganisms for instance phytopathogenic fungi or phytopathogenic oomycetes.
  • sccd(s) as used herein include dormant seeds, primed seeds, pregerminated seeds and seeds with emerged roots and leaves.
  • the present invention also relates to a method for protecting seeds from unwanted microorganisms which comprises the step of treating the seeds with the compound or the composition of the invention.
  • the treatment of seeds with the compound or the composition of the invention protects the seeds from phytopathogenic microorganisms, but also protects the germinating seeds, the emerging seedlings and the plants after emergence from the treated seeds. Therefore, the present invention also relates to a method for protecting seeds, germinating seeds and emerging seedlings.
  • the seeds treatment may be performed prior to sowing, at the time of sowing or shortly thereafter.
  • the seeds treatment may be performed as follows: the seeds may be placed into a mixer with a desired amount of the compound or the composition of the invention, the seeds and the compound or the composition of the invention are mixed until an homogeneous distribution on seeds is achieved. If appropriate, the seeds may then be dried.
  • the invention also relates to seeds coated with the compound or the composition of the invention.
  • the seeds are treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment.
  • seeds can be treated at any time between harvest and shortly after sowing. It is customary to use seeds which have been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seeds which have been harvested, cleaned and dried down to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seeds which, after drying, for example, have been treated with water and then dried again, or seeds just after priming, or seeds stored in primed conditions or pre-germinated seeds, or seeds sown on nursery trays, tapes or paper.
  • the amount of the compound or the composition of the invention applied to the seeds is typically such that the germination of the seed is not impaired, or that the resulting plant is not damaged. This must be ensured particularly in case the the compound of the invention would exhibit phytotoxic effects at certain application rates.
  • the intrinsic phenotypes of transgenic plants should also be taken into consideration when determining the amount of the compound of the invention to be applied to the seed in order to achieve optimum seed and germinating plant protection with a minimum amount of compound being employed.
  • the compound of the invention can be applied as such, directly to the seeds, i.e. without the use of any other components and without having been diluted. Also the composition of the invention can be applied to the seeds.
  • the compound and the composition of the invention are suitable for protecting seeds of any plant variety.
  • Preferred seeds are that of cereals (such as wheat, barley, rye, millet, triticale, and oats), oilseed rape, maize, cotton, soybean, rice, potatoes, sunflower, beans, coffee, peas, beet (e.g. sugar beet and fodder beet), peanut, vegetables (such as tomato, cucumber, onions and lettuce), lawns and ornamental plants. More preferred are seeds of wheat, soybean, oilseed rape, maize and rice.
  • the compound and the composition of the invention may be used for treating transgenic seeds, in particular seeds of plants capable of expressing a polypeptide or protein which acts against pests, herbicidal damage or abiotic stress, thereby increasing the protective effect.
  • Seeds of plants capable of expressing a polypeptide or protein which acts against pests, herbicidal damage or abiotic stress may contain at least one heterologous gene which allows the expression of said polypeptide or protein.
  • These heterologous genes in transgenic seeds may originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • These heterologous genes preferably originate from Bacillus sp., in which case the gene product is effective against the European com borer and/or the Western com rootworm.
  • the heterologous genes originate from Bacillus thuringiensis.
  • the compound and the composition of the invention may also have very good antimycotic effects. They have a very broad antimycotic activity spectrum, especially against dermatophytes and yeasts, moulds and diphasic fungi (for example against Candida species, such as Candida albicans, Candida glabrata), and Epidermophyton floccosum, Aspergillus species, such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species, such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • the enumeration of these fungi by no means constitutes a restriction of the mycotic spectrum covered, and is merely of illustrative character.
  • the compound and the composition of the invention may also be used to control important fungal pathogens in fish and cmstacea farming, e.g. saprolegnia diclina in trouts, saprolegnia parasitica in crayfish.
  • the compound and the composition of the invention may therefore be used both in medical and in non medical applications.
  • the compound and the composition of the invention may, at particular concentrations or application rates, also be used as herbicides, safeners, growth regulators or agents to improve plant properties, or as microbicides, for example as bactericides, viricides (including compositions against viroids) or as compositions against MLO (Mycoplasma-like organisms) and RLO (Rickettsia-like organisms).
  • the compound and the composition of the invention may intervene in physiological processes of plants and may therefore also be used as plant growth regulators.
  • Plant growth regulators may exert various effects on plants. The effect of the substances depends essentially on the time of application in relation to the developmental stage of the plant, and also on the amounts of active ingredient applied to the plants or their environment and on the type of application. In each case, growth regulators should have a particular desired effect on the crop plants.
  • Growth regulating effects comprise earlier germination, better emergence, more developed root system and/or improved root growth, increased ability of tillering, more productive tillers, earlier flowering, increased plant height and/or biomass, shorting of stems, improvements in shoot growth, number of kemels/ear, number of ears/m 2 , number of stolons and/or number of flowers, enhanced harvest index, bigger leaves, less dead basal leaves, improved phyllotaxy, earlier maturation / earlier fruit finish, homogenous riping, increased duration of grain filling, better fruit finish, bigger fruit/vegetable size, sprouting resistance and reduced lodging.
  • Increased or improved yield is referring to total biomass per hectare, yield per hectare, kemel/fiuit weight, seed size and/or hectolitre weight as well as to improved product quality, comprising: improved processability relating to size distribution (for example kernel, fruit), homogenous riping, grain moisture, better milling, better vinification, better brewing, increased juice yield, harvestability, digestibility, sedimentation value, falling number, pod stability, storage stability, improved fiber length/strength/uniformity, increase of milk and/or meet quality of silage fed animals, adaptation to cooking and frying; improved marketability relating to improved fruit/grain quality, size distribution (for example kernel, fruit), increased storage / shelf-life, firmness / softness, taste (aroma, texture), grade (for example size, shape, number of berries), number of berries/fruits per bunch, crispness, freshness, coverage with wax, frequency of physiological disorders, colour; increased desired ingredients such as e.g.
  • protein content fatty acids, oil content, oil quality, aminoacid composition, sugar content, acid content (pH), sugar/acid ratio (Brix), polyphenols, starch content, nutritional quality, gluten content/index, energy content, taste; decreased undesired ingredients such as e.g. less mycotoxines, less aflatoxins, geosmin level, phenolic aromas, lacchase, polyphenol oxidases and peroxidases, nitrate content.
  • Plant growth-regulating compounds can be used, for example, to slow down the vegetative growth of the plants.
  • Such growth depression is of economic interest, for example, in the case of grasses, since it is thus possible to reduce the frequency of grass cutting in ornamental gardens, parks and sport facilities, on roadsides, at airports or in fruit crops.
  • Also of significance is the inhibition of the growth of herbaceous and woody plants on roadsides and in the vicinity of pipelines or overhead cables, or quite generally in areas where vigorous plant growth is unwanted.
  • growth regulators for inhibition of the longitudinal growth of cereal. This reduces or completely eliminates the risk of lodging of the plants prior to harvest.
  • growth regulators in the case of cereals can strengthen the culm, which also counteracts lodging.
  • the employment of growth regulators for shortening and strengthening culms allows the deployment of higher fertilizer volumes to increase the yield, without any risk of lodging of the cereal crop.
  • vegetative growth depression allows denser planting, and it is thus possible to achieve higher yields based on the soil surface.
  • Another advantage of the smaller plants obtained in this way is that the crop is easier to cultivate and harvest.
  • Reduction of the vegetative plant growth may also lead to increased or improved yields because the nutrients and assimilates are of more benefit to flower and fruit formation than to the vegetative parts of the plants.
  • growth regulators can also be used to promote vegetative growth. This is of great benefit when harvesting the vegetative plant parts. However, promoting vegetative growth may also promote generative growth in that more assimilates are formed, resulting in more or larger fruits.
  • beneficial effects on growth or yield can be achieved through improved nutrient use efficiency, especially nitrogen (N)-use efficiency, phosphorous (P)-use efficiency, water use efficiency, improved transpiration, respiration and/or CO 2 assimilation rate, better nodulation, improved Ca- metabolism.
  • nitrogen (N)-use efficiency especially nitrogen (N)-use efficiency, phosphorous (P)-use efficiency, water use efficiency, improved transpiration, respiration and/or CO 2 assimilation rate, better nodulation, improved Ca- metabolism.
  • growth regulators can be used to alter the composition of the plants, which in turn may result in an improvement in quality of the harvested products. Under the influence of growth regulators, parthenocarpic fruits may be formed. In addition, it is possible to influence the sex of the flowers. It is also possible to produce sterile pollen, which is of great importance in the breeding and production of hybrid seed.
  • growth regulators can control the branching of the plants.
  • by breaking apical dominance it is possible to promote the development of side shoots, which may be highly desirable particularly in the cultivation of ornamental plants, also in combination with an inhibition of growth.
  • side shoots which may be highly desirable particularly in the cultivation of ornamental plants, also in combination with an inhibition of growth.
  • the amount of leaves on the plants can be controlled such that defoliation of the plants is achieved at a desired time.
  • defoliation plays a major role in the mechanical harvesting of cotton, but is also of interest for facilitating harvesting in other crops, for example in viticulture.
  • Defoliation of the plants can also be undertaken to lower the transpiration of the plants before they are transplanted.
  • growth regulators can modulate plant senescence, which may result in prolonged green leaf area duration, a longer grain filling phase, improved yield quality.
  • Growth regulators can likewise be used to regulate fruit dehiscence. On the one hand, it is possible to prevent premature fruit dehiscence. On the other hand, it is also possible to promote fruit dehiscence or even flower abortion to achieve a desired mass (“thinning”). In addition it is possible to use growth regulators at the time of harvest to reduce the forces required to detach the fruits, in order to allow mechanical harvesting or to facilitate manual harvesting.
  • Growth regulators can also be used to achieve faster or else delayed ripening of the harvested material before or after harvest. This is particularly advantageous as it allows optimal adjustment to the requirements of the market. Moreover, growth regulators in some cases can improve the fruit colour. In addition, growth regulators can also be used to synchronize maturation within a certain period of time. This establishes the prerequisites for complete mechanical or manual harvesting in a single operation, for example in the case of tobacco, tomatoes or coffee.
  • growth regulators By using growth regulators, it is additionally possible to influence the resting of seed or buds of the plants, such that plants such as pineapple or ornamental plants in nurseries, for example, germinate, sprout or flower at a time when they are normally not inclined to do so. In areas where there is a risk of frost, it may be desirable to delay budding or germination of seeds with the aid of growth regulators, in order to avoid damage resulting from late frosts.
  • growth regulators can induce resistance of the plants to frost, drought or high salinity of the soil. This allows the cultivation of plants in regions which are normally unsuitable for this purpose.
  • the compound and the composition of the invention may also exhibit a potent strengthening effect in plants. Accordingly, they may be used for mobilizing the defences of the plant against attack by undesirable microorganisms.
  • Plant-strengthening (resistance-inducing) substances in the present context are substances capable of stimulating the defence system of plants in such a way that the treated plants, when subsequently inoculated with undesirable microorganisms, develop a high degree of resistance to these microorganisms.
  • plant physiology effects comprise the following:
  • Abiotic stress tolerance comprising tolerance to high or low temperatures, drought tolerance and recovery after drought stress, water use efficiency (correlating to reduced water consumption), flood tolerance, ozone stress and UV tolerance, tolerance towards chemicals like heavy metals, salts, pesticides.
  • Biotic stress tolerance comprising increased fungal resistance and increased resistance against nematodes, viruses and bacteria.
  • biotic stress tolerance preferably comprises increased fungal resistance and increased resistance against nematodes and bacteria
  • Increased plant vigor comprising plant health / plant quality and seed vigor, reduced stand failure, improved appearance, increased recovery after periods of stress, improved pigmentation (e.g. chlorophyll content, stay-green effects) and improved photosynthetic efficiency.
  • the compounds of the invention can be applied as such, or for example in the form of as ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettable powders, pastes, soluble powders, dusts, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural products impregnated with the compound of the invention, synthetic substances impregnated with the compound of the invention, fertilizers or microencapsulations in polymeric substances.
  • Application is accomplished in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming, spreading-on and the like. It is also possible to deploy the compound of the invention by the ultra-low volume method, via a drip irrigation system or drench application, to apply it in- furrow or to inject it into the soil stem or trunk. It is further possible to apply the compound of the invention by means of a wound seal, paint or other wound dressing.
  • the effective and plant-compatible amount of the compound of the invention which is applied to the plants, plant parts, fruits, seeds or soil will depend on various factors, such as the compound/composition employed, the subject of the treatment (plant, plant part, fruit, seed or soil), the type of treatment (dusting, spraying, seed dressing), the purpose of the treatment (curative and protective), the type of microorganisms, the development stage of the microorganisms, the sensitivity of the microorganisms, the crop growth stage and the environmental conditions.
  • the application rates can vary within a relatively wide range, depending on the kind of application.
  • the application rate may range from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, more preferably from 50 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rockwool or perlite are used).
  • the application rate may range from 0.1 to 200 g per 100 kg of seeds, preferably from 1 to 150 g per 100 kg of seeds, more preferably from 2.5 to 25 g per 100 kg of seeds, even more preferably from 2.5 to 12.5 g per 100 kg of seeds.
  • the application rate may range from 0.1 to 10 000 g/ha, preferably from 1 to 5000 g/ha.
  • h LogP value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
  • LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% phosphoric acid and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
  • 1 H-NMR data of selected examples are written in form of 1 H-NMR-pcak lists. To each signal peak are listed the d-value in ppm and the signal intensity in round brackets. Between the d-value - signal intensity pairs are semicolons as delimiters.
  • the peak list of an example has therefore the form: di (intensityi); d2 (intensity2); . ; d; (intensity;); . ; d h (intensity n )
  • Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.
  • tetramethylsilane For calibrating chemical shift for 1 H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilane peak can occur but not necessarily.
  • the 1 H-NMR peak lists are similar to classical 1 H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.
  • peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90%).
  • Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore their peaks can help to recognize the reproduction of our preparation process via“side-products-fingerprints”.
  • Example A in vivo preventive test on Alternaria brassicae (leaf spot on radish or cabbage!
  • Emulsifier Im ⁇ of Tween ® 80 per mg of active ingredient
  • the active ingredients were made soluble and homogenized in a mixture of dimethyl sulfoxide/acetone/ /Tween ® 80 and then diluted in water to the desired concentration.
  • the young plants of radish or cabbage were treated by spraying the active ingredient prepared as described above.
  • Control plants were treated only with an aqueous solution of acetone/dimethyl sulfoxide/ Tween ® 80.
  • the plants were contaminated by spraying the leaves with an aqueous suspension of Alternaria brassicae spores.
  • the contaminated radish or cabbage plants were incubated for 6 days at 20°C and at 100% relative humidity.
  • the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: 1-01 ; 1-02; 1-03; 1-05; 1-06; 1-07; 1-08; 1-09; 1-10; 1-11; 1-16; 1-17; 1-20.
  • Example B in vivo preventive test on Botrytis cinerea (grey mould!
  • Emulsifier Im ⁇ of Tween ® 80 per mg of active ingredient
  • the active ingredients were made soluble and homogenized in a mixture of dimethyl sulfoxide/acetone/ /Tween ® 80 and then diluted in water to the desired concentration.
  • the young plants of gherkin were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone/dimethyl sulfoxide/ Tween ® 80.
  • the plants were contaminated by spraying the leaves with an aqueous suspension of Botrytis cinerea spores.
  • the contaminated gherkin plants were incubated for 4 to 5 days at l7°C and at 90% relative humidity.
  • the test was evaluated 4 to 5 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.
  • the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: 1-01 ; 1-02; 1-03; 1-05; 1-06; 1-08; 1-09; 1-10; 1-11 ; 1-16; 1-20.
  • Example C in vivo preventive test on Puccinia recondita thrown rust on wheat!
  • Emulsifier 1 m ⁇ of Tween ® 80 per mg of active ingredient
  • the active ingredients were made soluble and homogenized in a mixture of dimethyl sulfoxide/acetone/ /Tween ® 80 and then diluted in water to the desired concentration.
  • the young plants of wheat were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone/dimethyl sulfoxide/ Tween ® 80.
  • the plants were contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores.
  • the contaminated wheat plants were incubated for 24 hours at 20°C and at 100% relative humidity and then for 10 days at 20°C and at 70-80% relative humidity.
  • the test was evaluated 1 1 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.
  • the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: 1-01 ; 1-02; 1-03; 1-05; 1-06; 1-07; 1-08; 1-09; 1-10; 1-11; 1-12; 1-13; 1-14; 1-16; 1-17; 1-18; 1-19; 1-20.
  • Example D in vivo preventive test on Pyrenophora teres (net blotch on barley)
  • Emulsifier 1 m ⁇ of Tween ® 80 per mg of active ingredient
  • the active ingredients were made soluble and homogenized in a mixture of dimethyl sulfoxide/acetone/ /Tween ® 80 and then diluted in water to the desired concentration.
  • the young plants of barley were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone/dimethyl sulfoxide/ Tween ® 80.
  • the plants were contaminated by spraying the leaves with an aqueous suspension of Pyrenophora teres spores.
  • the contaminated barley plants were incubated for 48 hours at 20°C and at 100% relative humidity and then for 12 days at 20°C and at 70-80% relative humidity.
  • the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: 1-09; 1-16; 1-17. In this test, the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: 1-01 ; 1-02; 1-03; 1-06; 1-08; 1-10; 1-11 ; 1-13; 1-14; 1-20.
  • Example E in vivo preventive test on Septoria tritici (leaf spot on wheat!
  • Emulsifier Im ⁇ of Tween ® 80 per mg of active ingredient
  • the active ingredients were made soluble and homogenized in a mixture of dimethyl sulfoxide/acetone/ /Tween ® 80 and then diluted in water to the desired concentration.
  • the young plants of wheat were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone/dimethyl sulfoxide/ Tween ® 80.
  • the plants were contaminated by spraying the leaves with an aqueous suspension of Septoria tritici spores.
  • the contaminated wheat plants were incubated for 72 hours at l 8°C and at 100% relative humidity and then for 21 days at 20°C and at 90% relative humidity.
  • the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: 1-01 ; 1-02; 1-03; 1-05; 1-06; 1-07; 1-08; 1-09; 1-10; 1-11; 1-13; 1-14.
  • Example F in vivo preventive test on Sphaerotheca fulisinea (powdery mildew on cucurbits!
  • Emulsifier Im ⁇ of Tween ® 80 per mg of active ingredient
  • the active ingredients were made soluble and homogenized in a mixture of dimethyl sulfoxide/acetone/ /Tween ® 80 and then diluted in water to the desired concentration.
  • the young plants of gherkin were treated by spraying the active ingredient prepared as described above.
  • Control plants were treated only with an aqueous solution of acetone/dimethyl sulfoxide/ Tween ® 80.
  • the plants were contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuliginea spores.
  • the contaminated gherkin plants were incubated for 8 days at 20°C and at 70-80% relative humidity.
  • the test was evaluated 8 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.
  • the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: 1-01; 1-02; 1-03; 1-04; 1-05; 1-06; 1-07; 1-08; 1-09; 1-10; 1-11 ; 1-12; 1-13; 1-14; 1-15; 1-16; 1-17; 1-18; 1-19; 1-20.
  • Example G in vivo preventive test on Uromyces avvendiculatus (bean rust)
  • Emulsifier Im ⁇ of Tween ® 80 per mg of active ingredient
  • the active ingredients were made soluble and homogenized in a mixture of dimethyl sulfoxide/acetone/ /Tween ® 80 and then diluted in water to the desired concentration.
  • the young plants of bean were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone/dimethyl sulfoxide/ Tween ® 80.
  • the plants were contaminated by spraying the leaves with an aqueous suspension of Uromyces appendiculatus spores.
  • the contaminated bean plants were incubated for 24 hours at 20°C and at 100% relative humidity and then for 10 days at 20°C and at 70-80% relative humidity.
  • the test was evaluated 1 1 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.
  • the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: 1-01; 1-02; 1-03; 1-05; 1-06; 1-07; 1-08; 1-09; 1-10; 1-11; 1-12; 1-13; 1-14; 1-16; 1-17; 1-18; 1-19; 1-20.
  • Example H in vivo preventive test on Colletotrichum lindemuthianum (leaf spot on beanl
  • Emulsifier 1 m ⁇ of Tween ® 80 per mg of active ingredient
  • the active ingredients were made soluble and homogenized in a mixture of dimethyl sulfoxide/acetone/ /Tween ® 80 and then diluted in water to the desired concentration.
  • the young plants of bean were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone/dimethyl sulfoxide/ Tween ® 80.
  • the plants were contaminated by spraying the leaves with an aqueous suspension of Colletotrichum lindemuthianum spores.
  • the contaminated bean plants were incubated for 24 hours at 20°C and at 100% relative humidity and then for 6 days at 20°C and at 90% relative humidity.
  • the test was evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.
  • the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: 1-01; 1-02; 1-03; 1-06; 1-09; 1-10; 1-11 ; 1-12; 1-13; 1-14; 1-16; 1-17; 1-18; 1-20.
  • Example I in vivo preventive test on Venturia test (apples!
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 100 ppm of active ingredient: 1-01 ; 1-02; 1-05; 1-06; 1-08; 1-10; 1-11 ; 1-14; 1-16; 1-17.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • the plants were placed in the greenhouse at a temperature of approximately l 8°C and a relative atmospheric humidity of approximately 80% to promote the development of mildew pustules.

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

Abstract

La présente invention concerne des composés de formule (I), (I), dans laquelle Q représente un cycle aromatique à 6 chaînons tel que défini dans la description, et R1, R2, R3, R4 et R5 sont tels que définis dans la description, des compositions comprenant de tels composés et l'utilisation desdits composés, en particulier en tant que fongicides.
PCT/EP2019/053952 2018-02-21 2019-02-18 Dérivés de 1-(imidazol-1-yl à substitution en position 5)but-3-ène et leur utilisation en tant que fongicides WO2019162228A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111624268A (zh) * 2020-04-30 2020-09-04 上海市质量监督检验技术研究院 一种纺织品中异味化合物的检测方法

Citations (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3202604A1 (de) 1982-01-27 1983-08-04 Bayer Ag, 5090 Leverkusen Ether-derivate von substituierten 1-hydroxyalkyl-azolen, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren
EP0225739A2 (fr) 1985-12-10 1987-06-16 Imperial Chemical Industries Plc Dérivés de 2-2-diméthyl-3-hydroxy-3-propargyl-4-(1,2,4-triazol-1-yl)-butane comme régulateurs de croissance des plantes
EP0251086A2 (fr) 1986-06-23 1988-01-07 The Du Pont Merck Pharmaceutical Company Carbinols fongicides
DE3639877A1 (de) 1986-11-21 1988-05-26 Bayer Ag Hetarylalkyl substituierte 5- und 6-ringheterocyclen
EP0321211A1 (fr) 1987-12-17 1989-06-21 E.I. Du Pont De Nemours And Company Carbinols antifongiques
WO1989005581A1 (fr) 1987-12-17 1989-06-29 E.I. Du Pont De Nemours And Company Carbinols antifongiques
JPH02101067A (ja) 1988-10-07 1990-04-12 Kureha Chem Ind Co Ltd 新規アシル化トリアゾール誘導体、その製造法及び該誘導体を活性成分として含有する農園芸用殺菌剤
WO1991012000A1 (fr) 1990-02-13 1991-08-22 E.I. Du Pont De Nemours And Company DERIVES ANILINIQUES DE CARBINOLS DE STYRYLE-α EN TANT QU'AGENTS ANTIFONGIQUES
DE4419812A1 (de) 1993-09-16 1995-03-23 Bayer Ag Hydroxyethyl-azolyl-Derivate
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
FR2802772A1 (fr) 1999-12-22 2001-06-29 Agronomique Inst Nat Rech Utilisation d'un complexe elicitine-lipide pour la protection des plantes contre les pathogenes
WO2003106457A1 (fr) 2002-06-14 2003-12-24 Syngenta Limited Derives de spiroindolinepiperidine
WO2004099160A1 (fr) 2003-05-12 2004-11-18 Sumitomo Chemical Company, Limited Composes de pyrimidine et compostion de lutte contre les animaux nuisibles contenant ces composes
WO2006003494A2 (fr) 2004-06-28 2006-01-12 Syngenta Participations Ag Composes chimiques
WO2006043635A1 (fr) 2004-10-20 2006-04-27 Kumiai Chemical Industry Co., Ltd. Dérivé de 3-triazolylphénylsulfide et insecticide/acaricide/nématicide incluant ledit dérivé au titre de principe actif
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
WO2007040282A1 (fr) 2005-10-06 2007-04-12 Nippon Soda Co., Ltd. Compose d'amine cyclique et agent pesticide
CN101337940A (zh) 2008-08-12 2009-01-07 国家农药创制工程技术研究中心 具杀虫活性的含氮杂环二氯烯丙醚类化合物
CN101337937A (zh) 2008-08-12 2009-01-07 国家农药创制工程技术研究中心 具有杀虫活性的n-苯基-3-取代氨基吡唑类化合物
US20090030238A1 (en) 2007-07-23 2009-01-29 Burke Martin D System for controlling the reactivity of boronic acids
JP2010018586A (ja) 2008-07-14 2010-01-28 Meiji Seika Kaisha Ltd Ｐｆ１３６４物質、その製造方法、生産菌株、及び、それを有効成分とする農園芸用殺虫剤
WO2010052161A2 (fr) 2008-11-06 2010-05-14 Syngenta Participations Ag Compositions herbicides
WO2010051926A2 (fr) 2008-11-05 2010-05-14 Bayer Cropscience Aktiengesellschaft Nouveaux composés substitués par halogène
CN101715774A (zh) 2008-10-09 2010-06-02 浙江化工科技集团有限公司 一个具有杀虫活性化合物制备及用途
WO2010066780A1 (fr) 2008-12-12 2010-06-17 Syngenta Participations Ag N-oxypipéridines spirohétérocycliques utilisées comme pesticides
CN101824002A (zh) 2010-05-13 2010-09-08 南京华威医药科技开发有限公司 水溶性三唑类化合物及其合成方法
WO2011085575A1 (fr) 2010-01-15 2011-07-21 江苏省农药研究所股份有限公司 Composés de formanilide hétérocyclique, leurs procédés de synthèse et leur utilisation
WO2011105506A1 (fr) 2010-02-25 2011-09-01 日本曹達株式会社 Composé amine cyclique et acaricide
WO2011151146A1 (fr) 2010-05-31 2011-12-08 Syngenta Participations Ag Procédé d'amélioration du rendement d'un produit cultivé
WO2012029672A1 (fr) 2010-08-31 2012-03-08 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Agent de lutte contre des organismes nuisibles
WO2012034403A1 (fr) 2010-09-14 2012-03-22 中化蓝天集团有限公司 Composés de fluorométhoxypyrazole et d'anthranilamide, leurs procédés de synthèse et leurs utilisations
CN102391261A (zh) 2011-10-14 2012-03-28 上海交通大学 一种n-取代噁二嗪类化合物及其制备方法和应用
WO2012175119A1 (fr) 2011-06-22 2012-12-27 Isochem Procédé d'élaboration de solifénacine et de sels de solifénacine
WO2013050317A1 (fr) 2011-10-03 2013-04-11 Syngenta Limited Formes polymorphes d'un dérivé d'isoxazoline
CN103109816A (zh) 2013-01-25 2013-05-22 青岛科技大学 硫代苯甲酰胺类化合物及其应用
CN103232431A (zh) 2013-01-25 2013-08-07 青岛科技大学 一种二卤代吡唑酰胺类化合物及其应用
WO2013115391A1 (fr) 2012-02-01 2013-08-08 日本農薬株式会社 Dérivé d'arylalkyloxy pyrimidine, pesticide à usage agricole et horticole contenant le dérivé d'arylalkyloxy pyrimidine comme ingrédient actif, et son utilisation
CN103265527A (zh) 2013-06-07 2013-08-28 江苏省农用激素工程技术研究中心有限公司 邻氨基苯甲酰胺化合物及其制备方法和应用
WO2013144213A1 (fr) 2012-03-30 2013-10-03 Basf Se Composés de pyridylidène n-substitués et dérivés destinés à lutter contre les animaux nuisibles
EP2647626A1 (fr) 2012-04-03 2013-10-09 Syngenta Participations AG. Dérivés de 1-aza-spiro[4.5]déc-3-ène and 1,8-diaza-spiro[4.5]déc-3-ène en tant que pesticides
WO2013162716A2 (fr) 2012-04-27 2013-10-31 Dow Agrosciences Llc Compositions pesticides et procédés correspondants
CN103524422A (zh) 2013-10-11 2014-01-22 中国农业科学院植物保护研究所 苯并咪唑衍生物及其制备方法和用途
US20140213448A1 (en) 2012-04-27 2014-07-31 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
US20140275503A1 (en) 2013-03-13 2014-09-18 Dow Agrosciences Llc Process for the preparation of certain triaryl rhamnose carbamates
WO2014187846A1 (fr) 2013-05-23 2014-11-27 Syngenta Participations Ag Formulations de mélange en cuve
WO2015058021A1 (fr) 2013-10-17 2015-04-23 Dow Agrosciences Llc Procédés de préparation de de composés pesticides
WO2015058028A1 (fr) 2013-10-17 2015-04-23 Dow Agrosciences Llc Procédés de préparation de composés pesticides
WO2016005276A1 (fr) 2014-07-07 2016-01-14 Bayer Cropscience Aktiengesellschaft Procédé de préparation de composés fluorés d'iminopyridine
WO2016133011A1 (fr) 2015-02-17 2016-08-25 日本曹達株式会社 Composition agrochimique
WO2016154297A1 (fr) 2015-03-26 2016-09-29 Bayer Cropscience Lp Nouvelle souche de paenibacillus, composés antifongiques et procédés d'utilisation associés
WO2016156290A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5

Patent Citations (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3202604A1 (de) 1982-01-27 1983-08-04 Bayer Ag, 5090 Leverkusen Ether-derivate von substituierten 1-hydroxyalkyl-azolen, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren
EP0225739A2 (fr) 1985-12-10 1987-06-16 Imperial Chemical Industries Plc Dérivés de 2-2-diméthyl-3-hydroxy-3-propargyl-4-(1,2,4-triazol-1-yl)-butane comme régulateurs de croissance des plantes
EP0251086A2 (fr) 1986-06-23 1988-01-07 The Du Pont Merck Pharmaceutical Company Carbinols fongicides
DE3639877A1 (de) 1986-11-21 1988-05-26 Bayer Ag Hetarylalkyl substituierte 5- und 6-ringheterocyclen
EP0321211A1 (fr) 1987-12-17 1989-06-21 E.I. Du Pont De Nemours And Company Carbinols antifongiques
WO1989005581A1 (fr) 1987-12-17 1989-06-29 E.I. Du Pont De Nemours And Company Carbinols antifongiques
JPH02101067A (ja) 1988-10-07 1990-04-12 Kureha Chem Ind Co Ltd 新規アシル化トリアゾール誘導体、その製造法及び該誘導体を活性成分として含有する農園芸用殺菌剤
WO1991012000A1 (fr) 1990-02-13 1991-08-22 E.I. Du Pont De Nemours And Company DERIVES ANILINIQUES DE CARBINOLS DE STYRYLE-α EN TANT QU'AGENTS ANTIFONGIQUES
DE4419812A1 (de) 1993-09-16 1995-03-23 Bayer Ag Hydroxyethyl-azolyl-Derivate
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
FR2802772A1 (fr) 1999-12-22 2001-06-29 Agronomique Inst Nat Rech Utilisation d'un complexe elicitine-lipide pour la protection des plantes contre les pathogenes
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
WO2003106457A1 (fr) 2002-06-14 2003-12-24 Syngenta Limited Derives de spiroindolinepiperidine
WO2004099160A1 (fr) 2003-05-12 2004-11-18 Sumitomo Chemical Company, Limited Composes de pyrimidine et compostion de lutte contre les animaux nuisibles contenant ces composes
WO2006003494A2 (fr) 2004-06-28 2006-01-12 Syngenta Participations Ag Composes chimiques
WO2006043635A1 (fr) 2004-10-20 2006-04-27 Kumiai Chemical Industry Co., Ltd. Dérivé de 3-triazolylphénylsulfide et insecticide/acaricide/nématicide incluant ledit dérivé au titre de principe actif
WO2007040282A1 (fr) 2005-10-06 2007-04-12 Nippon Soda Co., Ltd. Compose d'amine cyclique et agent pesticide
WO2007040280A1 (fr) 2005-10-06 2007-04-12 Nippon Soda Co., Ltd. Cyclic amine compound and pest control agent
US20090030238A1 (en) 2007-07-23 2009-01-29 Burke Martin D System for controlling the reactivity of boronic acids
JP2010018586A (ja) 2008-07-14 2010-01-28 Meiji Seika Kaisha Ltd Ｐｆ１３６４物質、その製造方法、生産菌株、及び、それを有効成分とする農園芸用殺虫剤
CN101337940A (zh) 2008-08-12 2009-01-07 国家农药创制工程技术研究中心 具杀虫活性的含氮杂环二氯烯丙醚类化合物
CN101337937A (zh) 2008-08-12 2009-01-07 国家农药创制工程技术研究中心 具有杀虫活性的n-苯基-3-取代氨基吡唑类化合物
CN101715774A (zh) 2008-10-09 2010-06-02 浙江化工科技集团有限公司 一个具有杀虫活性化合物制备及用途
WO2010051926A2 (fr) 2008-11-05 2010-05-14 Bayer Cropscience Aktiengesellschaft Nouveaux composés substitués par halogène
WO2010052161A2 (fr) 2008-11-06 2010-05-14 Syngenta Participations Ag Compositions herbicides
WO2010066780A1 (fr) 2008-12-12 2010-06-17 Syngenta Participations Ag N-oxypipéridines spirohétérocycliques utilisées comme pesticides
WO2011085575A1 (fr) 2010-01-15 2011-07-21 江苏省农药研究所股份有限公司 Composés de formanilide hétérocyclique, leurs procédés de synthèse et leur utilisation
WO2011105506A1 (fr) 2010-02-25 2011-09-01 日本曹達株式会社 Composé amine cyclique et acaricide
CN101824002A (zh) 2010-05-13 2010-09-08 南京华威医药科技开发有限公司 水溶性三唑类化合物及其合成方法
WO2011151146A1 (fr) 2010-05-31 2011-12-08 Syngenta Participations Ag Procédé d'amélioration du rendement d'un produit cultivé
WO2012029672A1 (fr) 2010-08-31 2012-03-08 Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 Agent de lutte contre des organismes nuisibles
WO2012034403A1 (fr) 2010-09-14 2012-03-22 中化蓝天集团有限公司 Composés de fluorométhoxypyrazole et d'anthranilamide, leurs procédés de synthèse et leurs utilisations
WO2012175119A1 (fr) 2011-06-22 2012-12-27 Isochem Procédé d'élaboration de solifénacine et de sels de solifénacine
WO2013050317A1 (fr) 2011-10-03 2013-04-11 Syngenta Limited Formes polymorphes d'un dérivé d'isoxazoline
CN102391261A (zh) 2011-10-14 2012-03-28 上海交通大学 一种n-取代噁二嗪类化合物及其制备方法和应用
WO2013115391A1 (fr) 2012-02-01 2013-08-08 日本農薬株式会社 Dérivé d'arylalkyloxy pyrimidine, pesticide à usage agricole et horticole contenant le dérivé d'arylalkyloxy pyrimidine comme ingrédient actif, et son utilisation
WO2013144213A1 (fr) 2012-03-30 2013-10-03 Basf Se Composés de pyridylidène n-substitués et dérivés destinés à lutter contre les animaux nuisibles
EP2647626A1 (fr) 2012-04-03 2013-10-09 Syngenta Participations AG. Dérivés de 1-aza-spiro[4.5]déc-3-ène and 1,8-diaza-spiro[4.5]déc-3-ène en tant que pesticides
US20140213448A1 (en) 2012-04-27 2014-07-31 Dow Agrosciences Llc Pesticidal compositions and processes related thereto
WO2013162716A2 (fr) 2012-04-27 2013-10-31 Dow Agrosciences Llc Compositions pesticides et procédés correspondants
WO2013162715A2 (fr) 2012-04-27 2013-10-31 Dow Agrosciences Llc Compositions pesticides et procédés correspondants
CN103109816A (zh) 2013-01-25 2013-05-22 青岛科技大学 硫代苯甲酰胺类化合物及其应用
CN103232431A (zh) 2013-01-25 2013-08-07 青岛科技大学 一种二卤代吡唑酰胺类化合物及其应用
US20140275503A1 (en) 2013-03-13 2014-09-18 Dow Agrosciences Llc Process for the preparation of certain triaryl rhamnose carbamates
WO2014187846A1 (fr) 2013-05-23 2014-11-27 Syngenta Participations Ag Formulations de mélange en cuve
CN103265527A (zh) 2013-06-07 2013-08-28 江苏省农用激素工程技术研究中心有限公司 邻氨基苯甲酰胺化合物及其制备方法和应用
CN103524422A (zh) 2013-10-11 2014-01-22 中国农业科学院植物保护研究所 苯并咪唑衍生物及其制备方法和用途
WO2015058021A1 (fr) 2013-10-17 2015-04-23 Dow Agrosciences Llc Procédés de préparation de de composés pesticides
WO2015058028A1 (fr) 2013-10-17 2015-04-23 Dow Agrosciences Llc Procédés de préparation de composés pesticides
WO2016005276A1 (fr) 2014-07-07 2016-01-14 Bayer Cropscience Aktiengesellschaft Procédé de préparation de composés fluorés d'iminopyridine
WO2016133011A1 (fr) 2015-02-17 2016-08-25 日本曹達株式会社 Composition agrochimique
WO2016154297A1 (fr) 2015-03-26 2016-09-29 Bayer Cropscience Lp Nouvelle souche de paenibacillus, composés antifongiques et procédés d'utilisation associés
WO2016156290A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5

Non-Patent Citations (53)

* Cited by examiner, † Cited by third party
Title
"Database", Database accession no. 564025
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, pages 7207 - 7213
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1105672-77-2
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1108184-52-6
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1181213-14-8
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1204776-60-2
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1225292-17-0
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1226889-14-0
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1229023-00-0
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1229023-34-0
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1232543-85-9
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1233882-22-8
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1253850-56-4
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1268277-22-0
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 129531-12-0
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1332628-83-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1332838-17-1
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1363400-41-2
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1370358-69-2
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1440516-42-6
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1449021-97-9
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1449220-44-3
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1452877-50-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1461743-15-6
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1477919-27-9
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1477923-37-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1542271-46-4
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1638765-58-8
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1689566-03-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1702305-40-5
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 52836-31-4
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 637360-23-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 71526-07-3
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 792914-58-0
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 872999-66-1
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 885026-50-6
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 933798-27-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 934001-66-8
HATANO ET AL., J. ORG. CHEM., vol. 75, no. 15, 2010, pages 5008 - 5016
IMAMOTO ET AL., J. AM. CHEM. SOC., vol. 111, no. 12, 1989, pages 4392 - 4398
INTERNATIONAL JOURNAL OF PHARMACEUTICS, vol. 94, no. 1-3, 1993, pages 11 - 14
JOURNAL OF ORGANIC CHEMISTRY, 2012, pages 9458 - 9472
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, pages 15556
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, pages 19358 - 19361
KRASOVSKIY ET AL., ANGEW. CHEM. INT. ED., vol. 45, no. 3, 2006, pages 497 - 500
MAURIN ET AL., PHARMACEUTICAL RESEARCH, vol. 10, no. 2, 1993, pages 309 - 12
METZGER ET AL., ANGEW. CHEM. INT. ED., vol. 49, no. 27, 2010, pages 4665 - 4668
ONGENA, M. ET AL.: "Bacillus Lipopeptides: Versatile Weapons for Plant Disease Biocontrol", TRENDS IN MICROBIOLOGY, vol. 16, no. 3, March 2008 (2008-03-01), pages 115 - 125, XP022509718, DOI: doi:10.1016/j.tim.2007.12.009
ORG. LETT., vol. 18, no. 1, 2016, pages 16 - 19
ORGANIC LETTERS, 2013, pages 554 - 557
PIOU; ROVIS, J. AM. CHEM. SOC., vol. 136, no. 32, 2014, pages 11292 - 11295
QUINIO ET AL., SYNLETT, vol. 26, no. 04, 2015, pages 514 - 518
WEIDMANN; SEEBACH, ANGEW. CHEM. INT. ED., vol. 22, no. 1, 1983, pages 31 - 45

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