EP2928297A1 - Utilisation de 1-(aryléthinyl)-bicycloalcanols, 1-(hétéroaryléthinyl)-bicycloalcanols, 1-(hétérocyclyléthinyl)-bicycloalcanols et 1-(cyloalcényléthinyl)-bicycloalcanols substitués comme principes actifs contre le stress abiotique des plantes - Google Patents

Utilisation de 1-(aryléthinyl)-bicycloalcanols, 1-(hétéroaryléthinyl)-bicycloalcanols, 1-(hétérocyclyléthinyl)-bicycloalcanols et 1-(cyloalcényléthinyl)-bicycloalcanols substitués comme principes actifs contre le stress abiotique des plantes

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Publication number
EP2928297A1
EP2928297A1 EP13799047.9A EP13799047A EP2928297A1 EP 2928297 A1 EP2928297 A1 EP 2928297A1 EP 13799047 A EP13799047 A EP 13799047A EP 2928297 A1 EP2928297 A1 EP 2928297A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
aryl
alkoxycarbonyl
alkylaminocarbonyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP13799047.9A
Other languages
German (de)
English (en)
Inventor
Jens Frackenpohl
Thomas Müller
Jan Dittgen
Dirk Schmutzler
Juan Pedro RUIZ-SANTAELLA MORENO
Martin Jeffrey Hills
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Priority to EP13799047.9A priority Critical patent/EP2928297A1/fr
Publication of EP2928297A1 publication Critical patent/EP2928297A1/fr
Withdrawn legal-status Critical Current

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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
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    • C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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Definitions

  • sucrose synthase and proline transporters are involved here (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51: 463-499).
  • the stress control of plants against cold and Dryness partly uses the same molecular mechanisms.
  • LSA proteins Late Embryogenesis Abundant Proteins
  • These are chaperones that stabilize vesicles, proteins and membrane structures in stressed plants (Bray, 1993, Plant Physiol 103: 1035-1040).
  • induction of aldehyde dehydrogenases which detoxify the reactive oxygen species (ROS) produced by oxidative stress, is often used (Kirch et al., 2005, Plant Mol Biol 57: 315-332).
  • ROS reactive oxygen species
  • HSF Heat Shock Factors
  • HSP Heat Shock Proteins
  • Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589]. It is also known that chemical substances can increase the tolerance of plants to abiotic stress. Such substances are applied either by seed dressing, by foliar spraying or by soil treatment. Thus, an increase in the abioti stress tolerance of crops by treatment with systemic acquired resistance (SAR) or elicitors
  • SAR systemic acquired resistance
  • PA P poly-ADP-ribose polymerases
  • PARG poly (ADP-ribose) glycohydrolases
  • plants have several endogenous reaction mechanisms that can effectively prevent various harmful organisms and / or natural abiotic stress.
  • the object of the present invention was to provide further compounds which increase the tolerance to abiotic stress in plants, in particular to effect a strengthening of plant growth and / or contribute to increasing the plant yield.
  • R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 , R 30 , R 31 , R 32 , R 34 , R 35 and R 36 and A 1 to A 9 are each as defined below and wherein the arrow indicates a bond to the respective grouping CR 6 in the general formula (I) stands,
  • R 2 , R 3 and R 4 independently of one another represent hydrogen, alkyl, aryl, heteroaryl,
  • Trialkylsilylalkoxyalkyloxy stands, for nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, halogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, arylalkynyl, trialkylsilylalkynyl, aryl, arylalkyl, arylalkoxy, heteroaryl, haloalkyl, halocycloalkyl, haloalkenyl, alkoxy, haloalkoxy, aryloxy, heteroaryloxy , Cycloalkyloxy, cycloalkylalkoxy, alkenyloxy, alkynylalkyloxy, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl,
  • Haloalkylcarbonylamino alkoxycarbonylamino, alkylaminocarbonylamino, alkyl (alkyl) aminocarbonylamino, alkylsulfonylamino, cycloalkylsulfonylamino, arylsulfonylamino, hetarylsulfonylamino, sulfonylhaloalkylamino,
  • Aminoalkylsulfonyl aminohaloalkylsulfonyl, alkylaminosulfonyl,
  • Alkoxyalkoxycarbonyl alkenyloxyalkoxycarbonyl, alkylaminoalkoxycarbonyl, trisalkylsilyloxyalkoxycarbonyl, bis-alkylaminoalkoxycarbonyl,
  • Heterocyclylalkoxycarbonyl heterocyclyloxycarbonyl, alkenylalkoxycarbonyl, alkynylalkoxycarbonyl, arylalkynyloxycarbonyl, arylalkenyloxycarbonyl,
  • Aminocarbonyl alkylaminocarbonyl, bisalkylaminocarbonyl,
  • Heteroarylalkylaminocarbonyl cyanoalkylaminocarbonyl, Haloalkylaminocarbonyl, alkynylalkylaminocarbonyl,
  • Alkoxycarbonylheterocyclyl alkenyloxycarbonylheterocyclyl,
  • Arylalkylaminocarbonylheterocyclyl alkenylaminocarbonylheterocyclyl,
  • Aminosulfonyl alkoxyalkylaminocarbonyl, alkoxycarbonylheterocyclyl-N- carbonyl, alkoxycarbonylalkylheterocyclylidenaminocarbonyl,
  • Alkoxycarbonylalkyl (alkyl) aminocarbonyl
  • R 1 and R 11 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 5 to 7-membered ring form,
  • R 13 , R 14 , R 15 and R 16 are each independently hydrogen, halogen, nitro, amino, cyano, alkyl, aryl, heteroaryl, cycloalkyl, cycloalkenyl, alkenyl, alkynyl, alkenylalkyl, alkynylalkyl, hydroxy, alkoxy, alkoxyalkoxy, alkoxyalkyl,
  • Aminoalkylsulfonyl aminohaloalkylsulfonyl, alkylaminosulfonyl,
  • R 21 and R 22 are each independently hydrogen, halogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkoxy, haloalkyl, haloalkoxyalkyl, alkoxyhaloalkyl, haloalkoxyhaloalkyl, alkylthio, haloalkylthio, alkylthioalkyl, hydroxycarbonyl, alkoxycarbonyl .
  • R 3 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 7 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a grouping NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 33 is hydrogen, halogen, (DC 8) alkyl, aryl, heteroaryl, heterocyclyl, (Ca-C8) - cycloalkyl. (C 2 -C 8) alkenyl, (DC 8) alkoxy, (Ci-C 8) alkoxy (CrC 8) alkyl,
  • R 2 , R 3 and R 4 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl,
  • R 5 is hydroxy, (dC 7) alkoxy, aryloxy, (C 3 -C 7) cycloalkyloxy, (C 2 -C 7) alkenyloxy, (C 2 -C 7) alkenyl (CrC 7) - alkyioxy, (CrC 7) alkoxy (Ci-C7) alkyloxy, (C1-C7) - alkylcarbonyloxy, arylcarbonyloxy, Heteroarylcarbonyioxy, (C3-C7) - cycloalkylcarbonyloxy, (Ci-C7) alkoxycarbonyloxy, (C 2 -C 7) - Aikenyioxycarbonyloxy, Aryioxy- (Ci-C 7) -aikyloxy, aryl (Ci-C 7) -alkyioxy, (C1-C7) - alkoxy (Ci-C7) alkoxy (CrC 7) -acyloxy, (C
  • (C 1 -C 7 ) -alkylamino bis [(C 1 -C 7 ) -alkyl] -amino, (C 2 -C 7 ) -alkenylamino, (C 1 -C -cycloalkylamino, (C 1 -C 7 ) -alkylcarbonylamino, (C 3 -C7) - cycloalkylcarbonylamino, arylcarbonylamino, heteroarylcarbonylamino, formylamino, (C 1 -C 7 ) -haloalkylcarbonylamino, (C 1 -C 7 ) -alkoxycarbonylamino, (C 1 -C 7 ) -alkylaminocarbonylamino, (C 1 -C 7 ) -alkyl [(Ci-C 7 ) alkyl] aminocarbonylamino, (C 1 -C 7 ) -alkylsulfon
  • heteroaryloxycarbonyl heteroaryl- (C 1 -C 7) -alkoxycarbonyl, heterocyclyl- (C 1 -C 7) -alkoxycarbonyl, heterocyclyloxycarbonyL (C 2 -C 7) -alkenyl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkynyl- (C 1 -C 7) -alkoxycarbonyl , Aryl- (C 2 -C 7) -alkynyloxycarbonyl, aryl- (C 2 -C 7) -alkenyloxycarbonyl, aminocarbonyl, (C 1 -C 7) -alkylaminocarbonyl, bis [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C-C7) - Alkyl] aminocarbonyl, (C 1 -C 7)
  • R 3 and R 4 with the atom to which they are attached, an exo-alkylidene group or a fully saturated, optionally substituted by O (oxygen), S
  • R 1 and R 11 optionally form further substituted 3 to 6-membered ring, R 1 and R 11 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 5 to 7-membered ring form,
  • R 1 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 3 and R 7 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a grouping NH, NR 37 and optionally further substituted 5 to 7-membered ring form,
  • R 3 and R 11 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 1 and R 3 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 5 to 7-membered ring form,
  • R 7 and R 11 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a grouping NH, NR 37 and optionally further substituted 5 to 7-membered ring form,
  • R 3 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 3 to 7-membered ring form
  • R 7 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a grouping NH, NR 37 and optionally further substituted 3 to 7-membered ring form
  • R 3, R 14, R 15 and R 16 are independently hydrogen, halogen, nitro, amino, cyano, (CrC 7) alkyl, aryl, heteroaryl, (C 3 -C 7) cycloalkyl, (C 4 -C 7) cycloalkenyl, (C2-C7) alkenyl, (C 2 -C 7) -alkynyl, (C2-C7) alkenyl (Ci-C7) alkyl, (C 2 -C 7) - Alkynyl- (C 1 -C 7 ) -alkyl, hydroxy, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (dC 7) alkyl, hydroxy (dC 7) alkyl, (dC 7) -haloalkoxy, (C1-C7)
  • R 17 and R 18 are independently hydrogen, halogen, (dC 7) alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7) cycloalkyl, (C 2 -C 7) alkenyl, (C 2 -C 7 ) alkynyl, (OO) alkoxy, (C 1 -C 7 ) alkoxy (C 1 -C 7 ) -alkyl, aryloxy (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) Haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 4) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -
  • a 5 represents S (sulfur), O (oxygen) or the groupings NH, N-CH 3 , N-CH 2 CH 3 , N-CH (CH 3 ) 2 , N-CO 2 t-Bu, N-aryl, N-heteroaryl, N-heterocyclyl is
  • R 19, R 20, R 23 and R 24 are independently hydrogen, (Ci-C7) alkyl, halogen, (C 3 -C 7) cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 7) alkenyl, (C 2 -C 7) - alkenyl, (C, -C7) alkyl, aryl (dC 7) alkyl, (dC 7) alkoxy, (Ci-C7) alkoxy (Ci -C 7) - alkoxy, (Ci-C7) alkoxy (Ci-C7) alkyl, hydroxy, (dC 7) -haloalkyl, (C1-C7) - haloalkylthio stand,
  • R 19 and R 23 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
  • a 6 , A 7 are identical or different and independently of one another represent O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 21 R 22 , where however, in no case are two N, O or S atoms adjacent, and wherein R 21 and R 22 in the group CR 21 R 22 are each the same or different
  • R 22 have meanings as defined below and R 22 and are independently hydrogen, halogen, (Ci-C 7) alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7) cycloalkyl, (C 2 -C 7) - Alkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 4 ) -haloalkoxy, (C 1 -C 4 ) -alkoxy C7) - haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 4 ) -haloalkyl, (C 1 -C 7 )
  • (C 1 -C 7) -alkylaminocarbonyl bis [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7) -alkyl] aminocarbonyl, (C 1 -C 7) -alkyl [(C 1 -C 7)] Alkoxy] aminocarbonyl, (C 2 -C 7) -alkenylaminocarbonyl, (C 3 -C 7) -cycloalkylaminocarbonyl,
  • R 30 , R 31 , R 32 , R 34 , R 35 and R 36 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, halogen, (C 3 -C 7 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, ( C 2 -C 7 ) -alkenyl, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (Ci-C7) haloalkyl, (Ci-C7) alkylthio, (CrC 7) are haloalkylthio,
  • a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the group CHR 33 , and wherein R 33 in the group CHR 33 has the meaning as defined below and
  • R 33 is hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (C 1 -C 7 ) -alkoxy, (Ci -C 7) alkoxy (Ci-C7) alkyl, aryloxy (Ci-C7) alkyl, (Ci-C7) haloalkoxy, (Ci-C7) haloalkyl, (Ci-C 7) Alkylthio, (C 1 -C 7) -haloalkylthio, hydroxycarbonyl, (C 1 -C 7) -alkoxycarbonyl, (C 3 -C 7) -cycloalkoxycarbonyl, aryl- (C 1 -C 7) -alkoxycarbonyl, (C 2 -C 7) -alkenyl
  • R 1 is (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) - Alkynyl, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkynyl- (C 1 -C 6 ) -alkyl,
  • R 2 , R 3 and R 4 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine,
  • R 5 is hydroxy, (C 1 -C 6 ) -alkoxy, aryloxy, (C 3 -C 6 ) -cycloalkyloxy, (C 2 -C 6 ) -alkenyloxy, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyloxy, ( C 1 -C 6 -alkoxy- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -G 3) -cycloalkylcarbonyloxy, (C 1 -C 6 ) -alkoxycarbonyloxy, (C 2 -C 6 ) Alkenyloxycarbonyloxy, aryloxy- (C 1 -C 6 ) -alkyloxy, aryl- (C 1 -C 6 ) -alkyl
  • R 6 for nitro, amino, hydroxy, hydrothio, thiocyanato, isothiocyanato, fluorine, chlorine,
  • heteroaryloxycarbonyl heteroaryl- (C 1 -C 6) -alkoxycarbonyl, heterocyclyl- (C 1 -C 6) -alkoxycarbonyl, heterocyclyloxycarbonyl, (C 2 -C 6) -alkenyl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkynyl- (Ci -C6) alkoxycarbonyl, aryl- (C2-Ce) alkynyloxycarbonyl, aryl- (C2-C6) -alkenyloxycarbonyl, aminocarbonyl, (d-Ce) -alkylaminocarbonyl, bis [(Ci-C6) -alkyl] aminocarbonyl, (Ci -C6) alkyl [(d-C6) alkyl] aminocarbonyl, (Ci-C6) alkyl [(CrC6) alkoxy] aminocarbonyl, (C 2
  • C3-C6) cycloalkyl (Ci-C 6) alkoxycarbonyl (Ci-C 6) alkyl, (C 2 -C 6) - alkenyloxycarbonyl (CRC6) alkyl, aryl (Ci-C6) - alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkylaminocarbonyl (C 1 -C 6) -alkyl, aminocarbonyl- (C 1 -C 6) -alkyl,
  • Aminoiminomethyl (C 1 -C 6) -alkoxyiminomethyl, (C 1 -C 6) -alkylaminoiminomethyl, bis [(C 1 -C 6) -alkyl] aminoiminomethyl, (C 3 -C 6) -cycloalkoxyiminomethyl, (C 3 -C 6) -cycloalkyl- (Ci -C6) -alkoximinomethyl, aryloximinomethyl, aryl- (Ci-CG) -alkoxyiminomethyl, aryl- (Ci-C6) -alkylaminoiminomethyl, (C2-C-6) -alkenyloxyiminomethyl, arylaminoiminomethyl, arylsulfonylaminoiminomethyl, heteroaryl- (Ci-C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl,
  • R 3 and R 4 with the atom to which they are attached, an exo-alkylidene group or a fully saturated, optionally substituted by O (oxygen), S
  • R 3 and R 7 with the atoms to which they are attached, a fully saturated or partially saturated, optionally by O (oxygen), S (sulfur) or form a group NH, NR 37 interrupted and optionally further substituted 5 to 7-membered ring,
  • R 3 and R 11 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 1 and R 3 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 5 to 7-membered ring form,
  • R 7 and R 11 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a grouping NH, NR 37 and optionally further substituted 5 to 7-membered ring form,
  • R 3 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 7 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a grouping NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 13, R 14, R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, (Ci-Ce) alkyl, optionally substituted phenyl, heteroaryl, (C 3 -C 6 ) cycloalkyl, (C 4 -C 6) -cycloalkenyl, (C 2 -C 6) alkenyl, (C 2 -C 6) - alkynyl, (C2-C6) alkenyl (Ci-C 6) - alkyl, (C 2 -C 6 ) -alkynyl- (C 1 -C 6 ) -alkyl, hydroxyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, ( Ci-C 6) alkoxy (Ci-C6) alkyl, hydroxy (Ci-
  • a 1 , A 2 , A 3 and A 4 are the same or different and are independently N
  • R 17 and R 18 independently of one another represent hydrogen, halogen, (C 1 -C 6 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -) C 6 ) -alkynyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, aryloxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy, ( C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -
  • R 19 , R 20 , R 23 and R 24 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, halogen, (C 3 -C 6 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 6 ) - alkenyl, (C 2 -C 6) - alkenyl, (CrC 6) alkyl, aryl (Ci-C 6) alkyl, (Ci-Ce) alkoxy, (Ci-C 6) alkoxy (Ci- C 6) - alkoxy, (Ci-C6) alkoxy (Ci-C 6) alkyl, hydroxy, (CrC 6) -haloalkyl, (dC 6) - haloalkylthio stand,
  • R 25 , R 26 , R 28 and R 29 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, halogen, (C 3 -C 6 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 6 ) - alkenyl, aryl (Ci-Ce) - alkyl, (Ci-Ce) alkoxy, (Ci-C6) alkoxy (Ci-C 6) alkoxy, (Ci-C 6) alkoxy (Ci- C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl,
  • a 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 27 , and wherein R 27 in the moiety CHR 27 has the meaning as defined below,
  • R 27 is hydrogen, halogen, (Ci-CeJ-alkyl, aryl, heteroaryl, heterocyclyl, (C3-Ce) - cycloalkyl, (C 2 -C 6) alkenyl, (Ci-C 6) alkoxy, (Ci- C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, aryloxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 6 ) -haloalkyl.
  • (C 1 -C 6) -alkylaminocarbonyl bis [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkyl] aminocarbonyl, (C 1 -C 6) -alkyl [(C 1 -C 6) -alkoxy] aminocarbonyl, (C 2 -C 6) -alkenylaminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl,
  • R 30 , R 31 , R 32 , R 34 , R 35 and R 36 are each independently hydrogen.
  • a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the group CHR 33 and wherein R 33 in the group CHR 33 has the meaning as defined below and
  • R 33 is hydrogen, halogen, (C 1 -C 6 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 1 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 1 -C 6 ) -alkoxy, ( C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, aryloxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 6 ) -haloalkyl, (C 1 -C 4) - Alkylthio, (C 1 -C 6) -haloalkylthio, hydroxycarbonyl, (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -cycloalkoxycarbonyl, aryl- (C 1 -C 6)
  • R 37 is (Ci-C 6) alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 6) -cycloalkyl, (C 2 -C 6) alkenyl, (Ci-C 6) alkoxy, (Ci- C 6) alkoxy- (Ci-C 6) alkyl, aryloxy (Ci-Cr>) alkyl, (Ci-C6) - alkoxycarbonyl, (C3-C6) - cycloalkoxycarbonyl, aryl (Ci-C6) alkoxycarbonyl, (C 2 -C 6) alkenyloxycarbonyl, (C 2 -C 6) alkynyloxycarbonyl, (C 1 -C 6) alkylcarbonyl, (C 3 -C 18) cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl.
  • R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 , R 30 , R 31 , R 32 , R 34 , R 35 and R 36 and A 1 to A 9 each have the meaning as defined below and wherein the arrow for a bond to the respective group CR 6 in the aforementioned formulas (la) to (lo) .
  • R 5 is hydroxy, (C 1 -C 6 ) -alkoxy, aryloxy, (C 3 -C 8) -cycloalkyloxy, (C 2 -C 6 ) -alkenyloxy, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (Ca-Ce) -cycloalkylcarbonyloxy, (d-CeJ-alkoxycarbonyloxy, (Cz-Ce Alkenyloxycarbonyloxy, aryloxy- (C 1 -C 6 ) -alkyloxy, aryl- (C 1 -C 6 ) -alkyloxy, (C 1 -
  • R 6 represents nitro, amino, hydroxy, Hydrothio, thiocyanato, isothiocyanato, fluorine, chlorine, bromine, iodine, (CrC 6) alkyl, (C 3 -C 6) -cycloalkyl, (C 2 -C 6) alkenyl, (C 4 -C 6) - cycloalkenyl, (C 2 -C 6) alkynyl, aryl (C2-C6) -alkynyl, tris [(Ci-C6) alkyl] silyl (C2-C 6) - alkynyl, aryl, aryl (Ci-C 6) alkyl, aryl (Ci-C 6) alkoxy, heteroaryl, (dC 6) - haloalkyl, (C 3 -C 6) halocycloalkyl, (C 2 - C 6) haloalkenyl, (Ci-C 6) alk
  • R 31 , R 32 , R 34 , R 35 and R 36 independently of one another represent hydrogen, (C 1 -C 5) -alkyl, fluorine, chlorine, bromine, iodine, (C 1 -C 6 -cycloalkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 2 -C 5) alkenyl, (Ci-C 5) alkoxy, (C1-C5) - haloalkyl, (CrC 5) alkylthio, (Ci-C 5) are haloalkylthio,
  • a 9 is O (oxygen), S (sulfur), NH, N-CH 3, N -OCH 3 or the group CHR and wherein R 33 in the group CHR 33 has the meaning as defined below and
  • R 33 is hydrogen, halogen, (C 1 -C 8 -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 5 ) -alkenyl, (C 1 -C 5 ) -alkoxy, (Ci -C r>) alkoxy (Ci-C 5) alkyl, (CrC 5) haloalkoxy, (Ci-C5) haloalkyl, (C1-C5) - alkylthio, (Ci-C5) haloalkylthio , Hydroxycarbonyl, (C 1 -C 5) -alkoxycarbonyl, (C 3 -C 6) -cycloalkoxycarbonyl, aryl- (C 1 -C 5) -alkoxycarbonyl, (C 2 -C 5) -alkenyloxycarbonyl, (C 2
  • Ethylaminosulfonyl n-propylaminosulfonyl, iso-propylaminosulfonyl, n-butylaminosulfonyl, tert-butylaminosulfonyl, iso-butylaminosulfonyl,
  • Aminoiminomethyl (Ci-C5) -alkoxyiminomethyl, (Ci-C5) -alkylaminoiminomethyl, bis [(Ci-C5) -alkyl] aminoiminomethyl, (C3-C6) -cycloalkoxyiminomethyl, (CS-CG) -cycloalkyl- (Ci-Cr ») -alkoximinomethyl, Aryloximinomethyl, aryl (Ci-Cr>) - alkoxyiminomethyl, aryl (Ci-C5) -alkylaminoiminomethyl, (C2-C5) - Alkenyloxyiminomethyl, Arylaminoiminomethyl, Arylsulfonylaminoiminomethyl, heteroaryl (CrCr>) alkyl, heterocyclic - (C 1 -C 5 ) -alkyl,
  • R 13 , R 14 , R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert. Butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
  • R 17 and R 18 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, optionally substituted phenyl, heteroaryl,
  • R 19 , R 2Ü , R 23 and R 24 are each independently hydrogen, methyl, ethyl, iso-propyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl, cyclopentyl,
  • Cyclohexyl optionally substituted phenyl, heteroaryl, heterocyclyl, trifluoromethyl, difluoromethyl,
  • R 19 and R 23 with the atoms to which they are attached form a completely saturated or partially saturated, optionally further substituted 5 to 7-membered ring,
  • a 6 , A 7 are identical or different and independently of one another represent O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 2 R 22 , but in no case are two N , O or S atoms are adjacent, and wherein R 21 and R 22 in the group CR 21 R 22 are each the same or different
  • R 21 and R 22 independently of one another are hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, n-propyl, optionally substituted phenyl, heteroaryl, heterocyclyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, Trifluoromethyl, difluoromethyl, trifluoromethoxy, methylthio,
  • Aminocarbonyl methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, iso-propylaminocarbonyl, dimethylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl,
  • R 25 , R 26 , R 28 and R 29 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, fluorine, chlorine, bromine , iodine, optionally substituted phenyl, heteroaryl, heterocyclyl, methoxy, ethoxy, trifluoromethyl, difluoromethyl,
  • R 30 , R 31 , R 32 , R 34 , R 35 and R 36 independently of one another are hydrogen, methyl, ethyl, n-propyl, isopropyl, fluorine, chlorine, bromine, iodine, cyclopropyl, optionally substituted phenyl, heteroaryl, Heterocyclyl, methoxy, ethoxy, n-propyloxy, iso-propyloxy, trifluoromethyl, difluoromethyl, methylthio, trifluoromethylthio,
  • a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the group CHR and wherein R 33 in the group CHR 33 has the meaning as defined below, and
  • Residue definitions apply both to the end products of the general formula (I) and correspondingly to the starting material or preparation required in each case for the preparation
  • R 1 is (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl, (C 4 -C 7) cycloalkenyl, (C2-C7) alkenyl, (C 2 -C 7) alkynyl , (C 2 -C 7) alkenyl (Ci-C7) alkyl, (C 2 -C 7) alkynyl (Ci-C7) alkyl,
  • I 3 and R 4 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkyl,
  • R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are independently hydrogen.
  • R 3 and R 4 with the atom to which they are attached, an exo-alkylidene group or a fully saturated, optionally substituted by O (oxygen), S
  • R 1 and R 11 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 5 to 7-membered ring form,
  • R 1 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 3 to 7-membered ring form
  • R 3 and R 7 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a grouping NH, NR 37 and optionally further substituted 5 to 7-membered ring form
  • R 3 and R 11 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 1 and R 3 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 5 to 7-membered ring form,
  • R 7 and R 11 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a grouping NH, NR 37 and optionally further substituted 5 to 7-membered ring form,
  • R 3 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 7 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a grouping NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 13 , R 14 , R 5 and R 16 independently represent hydrogen, halogen, nitro, amino, cyano.
  • Alkylaminocarbonyl bis [(Ci-C 7) alkyl] aminocarbonyl, (Ci-C 7) alkyl [(Ci-C 7) - Alkyljaminocarbonyl, (CrC 7) alkyl [(Ci-C7) alkoxy] aminocarbonyl , (C 2 -C 7 ) alkenylaminocarbonyl, (C 3 -C 7 ) -cycloalkylaminocarbonyl, arylaminocarbonyl, aryl- (C 1 -C 7 ) -alkylaminocarbonyl,
  • R 20, R 23 and R 24 are independently hydrogen, (Ci-C7) alkyl, halogen, (C 3 -C 7) cycloalkyl, aryl, heteroaryl, heterocyclyl, (C2-C7) alkenyl, ( C2-C7) - alkenyl (-C 7) alkyl, aryl (-C 7) alkyl, (dC 7) alkoxy, (Ci-C7) alkoxy (CrC 7) - alkoxy, (Ci-C 7 ) alkoxy- (C 1 -C 7 ) -alkyl, hydroxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkylthio, and R 23 having the atoms to which they are attached, a fully saturated or partially saturated, optionally form further substituted 5 to 7-membered ring,
  • a 6 , A 7 are identical or different and independently of one another represent O (oxygen), S (sulfur), NH, N-OCH 3, N-CH 3 or the group CR 21 R 22 , but in no case are two N , O or S atoms are adjacent, and wherein R 21 and R 22 in the group CR 21 R 22 are each the same or different
  • R 27 represents hydrogen, halogen, (C 1 -C 7 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 7 ) -cycloalkyl, (C 2 -C 7 ) -alkenyl, (C 1 -C 7 ) -alkoxy, (Ci-C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -alkoxy (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -haloalkyl, (C 1
  • R 30 , R 31 , R 32 , R 34 , R 35 and R 36 independently of one another are hydrogen, (C 1 -C 7 ) -alkyl, halogen, (C 3 -C 7 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 4 ) -cycloalkyl, C7) alkenyl, (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkoxy, (Ci-C7) alkoxy (Ci-C7) alkyl, (dC 7) -haloalkyl , (C 1 -C 7 ) -alkylthio, (C 1 -C 4 ) -haloalkylthio,
  • a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the group CHR 33 and wherein R 33 in the group CHR 33 has the meaning as defined below and
  • R 33 is hydrogen, halogen, (dC 7) alkyl, aryl, heteroaryl, heterocyclyl, (C3-C7) - cycloalkyl, (C 2 -C 7) alkenyl, (Ci-C7) alkoxy, (C -C 7) alkoxy (Ci-C7) alkyl, aryloxy (Ci-C7) alkyl, (Ci-C7) haloalkoxy, (Ci-C7) haloalkyl, (Ci-C 7 ) -Alkylthio, (C 1 -C 7 ) -haloalkylthio, hydroxycarbonyl, (C 1 -C 4 ) -alkoxycarbonyl, (C 3 -C 7 ) -cycloalkoxycarbonyl, aryl- (C 1 -C 7 ) -alkoxycarbonyl, (C 2 -C 7 ) -alkenyloxycarbonyl, (C 2
  • R 37 is (Ci-C /) -alkyl.
  • R 8 , R 9 , R 10 , R 11 and R 12 are not hydrogen and
  • R 3 and R 4 with the atom to which they are attached, an exo-alkylidene group or a fully saturated, optionally substituted by O (oxygen), S
  • R 1 and R 11 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 5 to 7-membered ring form,
  • R 1 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 3 and R 7 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a grouping NH, NR 37 and optionally further substituted 5 to 7-membered ring form,
  • R 3 and R 11 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 1 and R 3 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 5 to 7-membered ring form
  • R 7 and R 11 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a grouping NH, NR 37 and optionally further substituted 5 to 7-membered ring form
  • R 3 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a group NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 7 and R 9 with the atoms to which they are attached, a fully saturated or partially saturated, optionally interrupted by O (oxygen), S (sulfur) or a grouping NH, NR 37 and optionally further substituted 3 to 7-membered ring form,
  • R 13 , R 14 , R 15 and R 16 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, amino, cyano, (C 1 -C 6 ) -alkyl, optionally substituted phenyl, heteroaryl, (C 3 -C 6 ) cycloalkyl, (C 4 -C 6) -cycloalkenyl, (C 2 -C 6) alkenyl, (C 2 -C 6) - alkynyl, (C2-C6) alkenyl (Ci-C 6) - alkyl, (C 2 -C 6 ) -alkynyl (C 1 -C 6 ) -alkyl, hydroxy, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy, C 6 ) -alkoxy- (C 1 -C 6 )
  • a 1 , A 2 , A 3 and A 4 are the same or different and are independently N
  • R 17 and R 18 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6 ) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (C 1 -C 6 ) -cycloalkyl, (C 2 -C 6 ) - Alkenyl, (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, aryloxy- (C 1 -C 6 ) -alkyl, C 6 ) -haloalkoxy, (C 1 -C 6 ) -haloalkyl,
  • a 6 , A 7 are the same or different and are each independently O (oxygen), S (sulfur), NH, N-OCH 3 , N-CH 3 or the group CR 21 R 22 , but in no case two N -, O or S atoms are adjacent, and wherein R 21 and R 22 in the group CR 21 R 22 are identical or different
  • R 21 and R 22 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (d-Co) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (Ca-Ce) -cycloalkyl, (C 2 -C 6) -alkenyl, (Ci-Cr,) - alkoxy, (Ci-C6) -alkoxy- (Ci-Cc,) - alkyl,
  • a 8 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the moiety CHR 27 , and wherein R 27 in the moiety CHR 27 has the meaning as defined below,
  • R 30 , R 31 , R 32 , R 34 , R 35 and R 36 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, halogen, (C 3 -C 6 ) -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 6) Alkenyl, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkylthio,
  • a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the group CHR 33 , and wherein R 33 in the group CHR 33 has the meaning as defined below and
  • R 33 represents hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -alkyl, if appropriate
  • R 5 is hydroxy, (d-CeJ) alkoxy, aryloxy, (C 1 -C 12 -cycloalkyloxy, (C 2 -C 6) -alkenyloxy, (C 2 -C 6 ) -alkenyl- (C 1 -C 6 ) -alkyloxy, ( C 1 -C 6 -alkoxy- (C 1 -C 6 ) -alkyloxy, (C 1 -C 6 ) -alkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, (C 1 -C 6 ) -cycloalkylcarbonyloxy, (C 1 -C 6 -alkoxycarbonyloxy, (C 2 -C 6 ) - Alkenyloxycarbonyloxy, aryloxy- (C 1 -C 6 ) -alkyloxy, aryl- (C 1 -C 6 ) -alkyloxy, (d-C
  • R 6 is (C 1 -C 6 ) -alkylsulfonylaminocarbonyl, (Ca-Ce) -
  • R 21 and R 22 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 5 ) -alkyl, optionally substituted phenyl, heteroaryl, heterocyclyl, (Ca-Ce) -cycloalkyl, (C 2 -C 5 ) - Alkenyl, (C 1 -C 5 ) -alkoxy, (C 1 -C 5 ) -alkoxy- (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -haloalkoxy.
  • R 25 , R 26 , R 28 and R 29 independently of one another represent hydrogen, (C 1 -C 5) -alkyl, fluorine, chlorine, bromine, iodine, (C 1 -C 6 -cycloalkyl, aryl, heteroaryl, heterocyclyl, (C 2 -C 5) - alkenyl, aryl- (-C 5) alkyl, (CrC 5) alkoxy, (Ci-C 5) -haloalkyl stand,
  • R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 23 , R 24 , R 25 , R 26 , R 28 , R 29 , R 30 , R 31 , R 32 , R 34 , R 35 and R 36 and A 1 to A 9 each have the meaning as defined below and wherein the arrow for a bond to the respective group CR 6 in the aforementioned formulas (la) to (lo) , for hydroxy, methoxy, ethoxy, n-propyloxy, methylcarbonyloxy,
  • Arylaminoiminomethyl, arylsulfonylaminoiminomethyl, hydroxyaminocarbonyl, (C 1 -C 5) -alkoxyaminocarbonyl, aryl- (C 1 -C 6) -alkoxyaminocarbonyl, R 13 , R 14 , R 15 and R 16 are each independently hydrogen, fluoro, chloro, bromo, iodo, nitro , Amino, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert. Butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
  • Heteroarylcarbonylamino trifluoromethylcarbonylamino, methoxycarbonyiamino, ethoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n-propylsulfonylamino, cyclopropylsulfonylamino, cyclobutylsulfonylamino, cyclopentylsulfonylamino, cyclohexylsulfonylamino, arylsulfonylamino,
  • a 1 , A 2 , A 3 and A 4 are the same or different and are independently N
  • R 17 and R 18 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, optionally substituted phenyl, heteroaryl,
  • R 19 , R 20 , R 23 and R 24 are each independently hydrogen, methyl, ethyl, iso-propyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl, cyclopentyl,
  • R 21 and R 22 independently of one another are hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, n-propyl, optionally substituted phenyl, heteroaryl, heterocyclyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, Trifluoromethyl, difluoromethyl, trifluoromethoxy, methylthio,
  • Aminocarbonyl methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, iso-propylaminocarbonyl, dimethylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl,
  • R 25 , R 26 , R 28 and R 29 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, fluorine, chlorine, bromine , iodine, optionally substituted phenyl, heteroaryl, heterocyclyl, methoxy, ethoxy, trifluoromethyl, difluoromethyl,
  • a 8 is O (oxygen), S (sulfur), NH, N-CH 3, N -OCH 3 or the moiety CHR 27 and wherein R 27 in the moiety CHR 27 has the meaning as defined below,
  • R 27 is hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, n-propyl,
  • R 30 , R 31 , R 32 , R 34 , R 35 and R 36 independently of one another are hydrogen, methyl, ethyl, n-propyl, isopropyl, fluorine, chlorine, bromine, iodine, cyclopropyl, optionally substituted phenyl, heteroaryl, Heterocyclyl, methoxy, ethoxy, n-propyloxy, iso-propyloxy, trifluoromethyl, difluoromethyl, methylthio, trifluoromethylthio.
  • a 9 is O (oxygen), S (sulfur), NH, N-CH 3 , N-OCH 3 or the group CHR and wherein R 33 in the group CHR 33 has the meaning as defined below, and
  • R 33 is hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, n-propyl,
  • Alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups
  • 3-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl.
  • Heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazole-1 or 3 or 4 or 5-yl; 2,3-dihydro-1H-pyrazole-1 - or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1 - or 2- or 3- or 4-yl; 2,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1 - or 2- or 4- or 5-yl; Hexahydropyridazine-1 - or 2- or 3- or 4-yl; 1, 2,3,4-tetrahydropyridazine-1
  • 6- or 7-yl 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; isothiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazole-2- or 3- or 4- or 5-yl; 2.5-
  • quinazoline cinnoline; 1,5-naphthyridine; 1, 6-naphthyridine; 1,7-naphthyridine; 1 .8- naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
  • a suitable base e.g., 2,6-lutidine
  • a suitable polar aprotic solvent e.g., dichloromethane
  • this reaction is described in Scheme 3 using triethylsilyl trifluoromethanesulfonate.
  • a suitable gold catalyst for example gold (III) bromide, gold (III) chloride
  • the substituted (E) -configured 1-arylvinyl-, 1-heteroarylvinyl-, 1-cycloalkenylvinylbicycloalkanols (I.5) can be prepared by reduction of the Aicyruppe of the corresponding substituted 1- (arylethynyl) -, 1 - (heteroarylethynyl) -, 1 - (Heterocyclylethynyl) - and 1 - (cycloalkenylethynyl) bicycloalkanols (1.1)
  • Transition metal catalyst such as Lindlar's catalyst with hydrogen in a suitable polar-apro tic solvent (such as n-butanol) perform (see Tetrahedron 1987, 43, 4107, Tetrahedron 1983, 39, 2315, J. Org. 1983, 48, 4436 and J. Am. Chem. Soc., 1984, 106, 2735) (Scheme 5).
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , 7, R 8 , R 9 , R 10 , R 11 , R 12 and Q in Scheme 5 have the meanings defined above.
  • Fenchone (1500 mg, 9.85 mmol) was dissolved in a round bottom flask under argon in abs.
  • Tetra hydrofu ran (5 ml) and added dropwise to a solution of a lithium acetylide-ethylenediamine complex (1474 mg, 12.81 mmol, 80% content) in abs. Tetrahydrofuran (10 ml) was added. The reaction solution was stirred for 2 h after the addition at room temperature, then treated with water and concentrated under reduced pressure. The remaining residue was mixed with water and dichloromethane and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • Tetra hydrofu ran (5 ml) and added dropwise to a solution of a lithium acetylide-ethylenediamine complex (1474 mg, 12.81 mmol, 80% content) in abs. Tetrahydrofuran (10 ml) was added. The reaction solution was stirred for 2 h after the addition at room temperature, then treated with water and concentrated under reduced pressure. The remaining residue was mixed with water and dichloromethane and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • reaction mixture was stirred for 1 h at 0 ° C and then washed with sat.
  • Tetra hydrofu ran (5 ml) and added dropwise to a solution of a Lithiumacetylid-ethylenediamine complex (1962 mg, 9.41 mmol, 90% content) in abs. Tetrahydrofuran (3 ml).
  • the reaction solution was stirred for 4 h after the addition at room temperature, then treated with water and concentrated under reduced pressure. The remaining residue was mixed with water and dichloromethane and the aqueous phase extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.

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Abstract

L'invention concerne l'utilisation de 1-(aryléthinyl)-bicycloalcanols, 1-(hétéroaryléthinyl)-bicycloalcanols, 1-(hétérocyclyléthinyl)-bicycloalcanols et 1-(cyloalcényléthinyl)-bicycloalcanols substitués ou de leurs sels, représentés par la formule générale (I), dans laquelle les groupes sont tels que définis dans la description, pour accroître la tolérance des plantes au stress abiotique et/ou augmenter le rendement des plantes.
EP13799047.9A 2012-12-05 2013-12-02 Utilisation de 1-(aryléthinyl)-bicycloalcanols, 1-(hétéroaryléthinyl)-bicycloalcanols, 1-(hétérocyclyléthinyl)-bicycloalcanols et 1-(cyloalcényléthinyl)-bicycloalcanols substitués comme principes actifs contre le stress abiotique des plantes Withdrawn EP2928297A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP13799047.9A EP2928297A1 (fr) 2012-12-05 2013-12-02 Utilisation de 1-(aryléthinyl)-bicycloalcanols, 1-(hétéroaryléthinyl)-bicycloalcanols, 1-(hétérocyclyléthinyl)-bicycloalcanols et 1-(cyloalcényléthinyl)-bicycloalcanols substitués comme principes actifs contre le stress abiotique des plantes

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP12195676 2012-12-05
PCT/EP2013/075267 WO2014086723A1 (fr) 2012-12-05 2013-12-02 Utilisation de 1-(aryléthinyl)-bicycloalcanols, 1-(hétéroaryléthinyl)-bicycloalcanols, 1-(hétérocyclyléthinyl)-bicycloalcanols et 1-(cyloalcényléthinyl)-bicycloalcanols substitués comme principes actifs contre le stress abiotique des plantes
EP13799047.9A EP2928297A1 (fr) 2012-12-05 2013-12-02 Utilisation de 1-(aryléthinyl)-bicycloalcanols, 1-(hétéroaryléthinyl)-bicycloalcanols, 1-(hétérocyclyléthinyl)-bicycloalcanols et 1-(cyloalcényléthinyl)-bicycloalcanols substitués comme principes actifs contre le stress abiotique des plantes

Publications (1)

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EP2928297A1 true EP2928297A1 (fr) 2015-10-14

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EP13799047.9A Withdrawn EP2928297A1 (fr) 2012-12-05 2013-12-02 Utilisation de 1-(aryléthinyl)-bicycloalcanols, 1-(hétéroaryléthinyl)-bicycloalcanols, 1-(hétérocyclyléthinyl)-bicycloalcanols et 1-(cyloalcényléthinyl)-bicycloalcanols substitués comme principes actifs contre le stress abiotique des plantes

Country Status (7)

Country Link
US (1) US20150315146A1 (fr)
EP (1) EP2928297A1 (fr)
JP (1) JP2016504300A (fr)
CN (1) CN104955327A (fr)
AR (1) AR093820A1 (fr)
BR (1) BR112015013056A2 (fr)
WO (1) WO2014086723A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201617310A (zh) * 2014-07-18 2016-05-16 拜耳作物科學公司 作為用於抵抗非生物性植物逆境之活性成分的經取代之乙烯基－及炔基－氰基環烷醇與乙烯基－及炔基－氰基雜環烷醇
TWI735416B (zh) 2014-10-06 2021-08-11 美商維泰克斯製藥公司 囊腫纖維化症跨膜傳導調節蛋白之調節劑
PL3436446T3 (pl) 2016-03-31 2023-09-11 Vertex Pharmaceuticals Incorporated Modulatory mukowiscydozowego przezbłonowego regulatora przewodnictwa
CN109803962B (zh) 2016-09-30 2022-04-29 弗特克斯药品有限公司 囊性纤维化跨膜传导调控蛋白的调节剂、以及药物组合物
MA54847A (fr) 2016-12-09 2021-12-08 Vertex Pharma Forme crystalline d'un n-(pyrazol-4-yl)sulfonyl-6-(pyrazol-1-yl)-2-(pyrrolidin-1-yl)pyridine-3-carboxamide pour traiter la mucoviscidose
EP3634402A1 (fr) 2017-06-08 2020-04-15 Vertex Pharmaceuticals Incorporated Méthodes de traitement de la fibrose kystique
WO2019018395A1 (fr) 2017-07-17 2019-01-24 Vertex Pharmaceuticals Incorporated Méthodes de traitement de la fibrose kystique
ES2912657T3 (es) 2017-08-02 2022-05-26 Vertex Pharma Procesos para preparar compuestos de pirrolidina
AU2018351533B2 (en) 2017-10-19 2023-02-02 Vertex Pharmaceuticals Incorporated Crystalline forms and compositions of CFTR modulators
KR20200097293A (ko) 2017-12-08 2020-08-18 버텍스 파마슈티칼스 인코포레이티드 낭포성 섬유증 막횡단 전도 조절자의 조정제의 제조 방법
TWI810243B (zh) 2018-02-05 2023-08-01 美商維泰克斯製藥公司 用於治療囊腫纖化症之醫藥組合物
US11414439B2 (en) 2018-04-13 2022-08-16 Vertex Pharmaceuticals Incorporated Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator

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CA2647900C (fr) * 2008-12-23 2017-05-16 National Research Council Of Canada Inhibiteurs de 9-cis-epoxycarotenoide-dioxygenase
AR090010A1 (es) * 2011-04-15 2014-10-15 Bayer Cropscience Ag 5-(ciclohex-2-en-1-il)-penta-2,4-dienos y 5-(ciclohex-2-en-1-il)-pent-2-en-4-inos sustituidos como principios activos contra el estres abiotico de las plantas, usos y metodos de tratamiento
AR085585A1 (es) * 2011-04-15 2013-10-09 Bayer Cropscience Ag Vinil- y alquinilciclohexanoles sustituidos como principios activos contra estres abiotico de plantas

Non-Patent Citations (1)

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See references of WO2014086723A1 *

Also Published As

Publication number Publication date
WO2014086723A1 (fr) 2014-06-12
CN104955327A (zh) 2015-09-30
US20150315146A1 (en) 2015-11-05
JP2016504300A (ja) 2016-02-12
BR112015013056A2 (pt) 2017-07-11
AR093820A1 (es) 2015-06-24

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