EP3172187A1 - Substituierte cyano-cycloalkylpenta-2,4-diene, cyano-cycloalkylpent-2-en-4-ine, cyano-heterocyclylpenta-2,4-diene und cyano-heterocyclylpent-2en-4-ine als wirkstoffe gegen abiotischen pflanzenstress - Google Patents
Substituierte cyano-cycloalkylpenta-2,4-diene, cyano-cycloalkylpent-2-en-4-ine, cyano-heterocyclylpenta-2,4-diene und cyano-heterocyclylpent-2en-4-ine als wirkstoffe gegen abiotischen pflanzenstressInfo
- Publication number
- EP3172187A1 EP3172187A1 EP15738663.2A EP15738663A EP3172187A1 EP 3172187 A1 EP3172187 A1 EP 3172187A1 EP 15738663 A EP15738663 A EP 15738663A EP 3172187 A1 EP3172187 A1 EP 3172187A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- cycloalkyl
- bis
- alkoxy
- aryl
- 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- Withdrawn
Links
- -1 cyano cycloalkyl penta-2,4-dienes Chemical class 0.000 title claims abstract description 1017
- 239000013543 active substance Substances 0.000 title description 2
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 48
- 230000001965 increasing effect Effects 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 230000036579 abiotic stress Effects 0.000 claims abstract description 26
- 230000035882 stress Effects 0.000 claims abstract description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 212
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 145
- 239000007983 Tris buffer Substances 0.000 claims description 128
- 229910052739 hydrogen Inorganic materials 0.000 claims description 108
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 107
- 239000001257 hydrogen Substances 0.000 claims description 107
- 125000000623 heterocyclic group Chemical group 0.000 claims description 92
- 125000003118 aryl group Chemical group 0.000 claims description 83
- 229910052760 oxygen Inorganic materials 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 67
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 60
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 57
- 239000001301 oxygen Substances 0.000 claims description 57
- 229910052736 halogen Inorganic materials 0.000 claims description 50
- 150000002367 halogens Chemical class 0.000 claims description 50
- 239000000243 solution Substances 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 150000002431 hydrogen Chemical class 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 42
- 125000004434 sulfur atom Chemical group 0.000 claims description 40
- 229920006395 saturated elastomer Polymers 0.000 claims description 39
- 229910052717 sulfur Inorganic materials 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 35
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 34
- 125000005842 heteroatom Chemical group 0.000 claims description 34
- 125000001188 haloalkyl group Chemical group 0.000 claims description 33
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 30
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 28
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 28
- 125000004429 atom Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 23
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 22
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 22
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 22
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 21
- 239000003337 fertilizer Substances 0.000 claims description 21
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 239000011593 sulfur Substances 0.000 claims description 19
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 18
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 18
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 17
- 239000004009 herbicide Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 17
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 15
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 14
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 12
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- 239000007921 spray Substances 0.000 claims description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 10
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 10
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 235000015097 nutrients Nutrition 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 8
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 8
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 8
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000005038 alkynylalkyl group Chemical group 0.000 claims description 7
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 7
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 7
- 125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 claims description 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 5
- 125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 5
- 125000000707 boryl group Chemical group B* 0.000 claims description 5
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 5
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 5
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 239000003630 growth substance Substances 0.000 claims description 4
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 230000008723 osmotic stress Effects 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 3
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 3
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000002097 pentamethylcyclopentadienyl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- VVBXKASDRZXWON-UHFFFAOYSA-N N=[PH3] Chemical compound N=[PH3] VVBXKASDRZXWON-UHFFFAOYSA-N 0.000 claims description 2
- 230000000895 acaricidal effect Effects 0.000 claims description 2
- 239000000642 acaricide Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 2
- 125000000320 amidine group Chemical class 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 125000005127 aryl alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 2
- 239000005667 attractant Substances 0.000 claims description 2
- 239000003899 bactericide agent Substances 0.000 claims description 2
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 2
- 239000005645 nematicide Substances 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- ZXYNGLRGFYLTQZ-UHFFFAOYSA-M [Zn]Cl Chemical compound [Zn]Cl ZXYNGLRGFYLTQZ-UHFFFAOYSA-M 0.000 claims 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 1
- 230000000875 corresponding effect Effects 0.000 claims 1
- 230000004962 physiological condition Effects 0.000 claims 1
- GLBQVJGBPFPMMV-UHFFFAOYSA-N sulfilimine Chemical class S=N GLBQVJGBPFPMMV-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 172
- 241000196324 Embryophyta Species 0.000 description 171
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 138
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
- 238000005160 1H NMR spectroscopy Methods 0.000 description 109
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 96
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 94
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 92
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 60
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 230000002829 reductive effect Effects 0.000 description 58
- 108090000623 proteins and genes Proteins 0.000 description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 51
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 47
- 235000019341 magnesium sulphate Nutrition 0.000 description 47
- 239000008346 aqueous phase Substances 0.000 description 46
- 239000012043 crude product Substances 0.000 description 46
- 239000012074 organic phase Substances 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 35
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- 102000004169 proteins and genes Human genes 0.000 description 32
- 235000018102 proteins Nutrition 0.000 description 31
- 229910052786 argon Inorganic materials 0.000 description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 30
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 29
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 28
- 238000011097 chromatography purification Methods 0.000 description 27
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 150000003254 radicals Chemical class 0.000 description 25
- 239000003921 oil Substances 0.000 description 24
- 235000019198 oils Nutrition 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 22
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 21
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 20
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 20
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 19
- 238000004440 column chromatography Methods 0.000 description 19
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 19
- 229910052731 fluorine Inorganic materials 0.000 description 19
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 19
- 238000000746 purification Methods 0.000 description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 17
- 239000011737 fluorine Substances 0.000 description 17
- 235000009518 sodium iodide Nutrition 0.000 description 17
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 16
- 229910052794 bromium Inorganic materials 0.000 description 16
- 229910052801 chlorine Inorganic materials 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 16
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 16
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 15
- 230000000749 insecticidal effect Effects 0.000 description 15
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 15
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 14
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 14
- 241000238631 Hexapoda Species 0.000 description 13
- 239000012230 colorless oil Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- 102000004190 Enzymes Human genes 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
- 229940043279 diisopropylamine Drugs 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 150000001721 carbon Chemical group 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000036541 health Effects 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 10
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 9
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 9
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 9
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 9
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 9
- 239000003880 polar aprotic solvent Substances 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 8
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 8
- 241000193388 Bacillus thuringiensis Species 0.000 description 8
- 125000001980 alanyl group Chemical group 0.000 description 8
- 229940097012 bacillus thuringiensis Drugs 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
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Classifications
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- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
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- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
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- C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/08—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no 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 atoms
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/30—Germanium compounds
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- C07C2601/14—The ring being saturated
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- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Definitions
- the invention relates to substituted cyano-cycloalkylpenta-2,4-dienes, cyano-cycloalkylpent-2-en-4-enes, cyano-heterocyclylpenta-2,4-dienes and cyano-heterocyclylpent-2-en-4-enes, processes for their preparation and their use for increasing the stress tolerance in plants to abiotic stress and / or for increasing the yield of plants.
- Epoxycarotenoid dioxygenase and as germination inhibitors is described in US2010 / 0160166.
- (2Z, 4E) -5 - [(1S, 6S) -1-hydroxy-2,2,6-trimethylcyclohexyl] penta-2,4-dienoic acid and (2Z, 4E) -5- [(1R, 6R) -1 -HydrOxy-2,2,6-trimethylcyclohexyl] penta-2,4-dienoic acid interact with cytochrome P707A (see Current Med. Chem., 2010, 17, 3230).
- abscisic acid and its derivatives can be used as pharmaceutical agents for the regulation of calcium transport (see EP240257). It is also known that certain cyanocyclopropyl-substituted
- Aryltriazolylethanoles (see JP02286668) can be used as agrochemical active substances for controlling pathogenic fungi. Furthermore, only a few
- Cyanocycloalkyl-substituted alkenols as described, for example, 1 - [(2E) -1-hydroxy-1,3-diphenylprop-2-en-1-yl] cyclopentanecarbonitrile (in Dokl. Bolgarsk, Akad. Nauk 1971, 24, 621) and 1 - [(2E) -1-hydroxy-3-phenylprop-2-en-1-yl] cyclohexanecarbonitrile (in J. Organomt. Chem. 1973, 57, C36-C38).
- abiotic stress for example, cold, heat, drought stress, salt, flooding
- signal transduction chains e.g., transcription factors, kinases, phosphatases
- the signal chain genes of the abiotic stress reaction include, among others. Transcription factors of classes DREB and CBF (Jaglo-Ottosen et al., 1998,
- the response to salt stress involves phosphatases of the ATPK and MP2C types. Furthermore, in salt stress the biosynthesis of osmolytes such as proline or sucrose is often activated. Involved here are e.g. sucrose synthase and proline transporters (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51: 463-499). The stress control of plants against cold and
- Late Embryogenesis Abundant Proteins which include dehydrins as an important class, is known (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 100: 291-296). These are chaperones, the vesicles, proteins and
- HSF Heat Shock Factors
- HSP Heat Shock Proteins
- osmolytes e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives
- PARP poly-ADP-ribose polymerases
- PARG poly (ADP-ribose) glycohydrolases
- 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.
- the present invention accordingly provides cyano-cycloalkylpenta-2,4-dienes, cyano-cycloalkylpent-2-en-4-enes, cyano-heterocyclylpenta-2,4-dienes and cyano-heterocyclylpent-2-en-4-ines general formula (I) or salts thereof,
- R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each as defined below and wherein the arrow represents a bond to the respective grouping [XY],
- R 1 is hydrogen, alkyl, aryl, heteroaryl, heterocyclyl, cycloalkyl, alkenyl, alkynyl, alkynylalkyl, alkoxyalkyl, hydroxyalkyl, haloalkyl, haloalkenyl, haloalkoxyalkyl, alkylthioalkyl, arylalkyl, heterocyclylalkyl, halocycloalkyl, cycloalkenyl,
- R 2 is hydrogen, alkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkenyl, alkynyl,
- a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
- Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
- R 3 and R 4 independently of one another represent hydrogen, alkyl, halogen, cycloalkyl, alkoxy, aryl, heterocyclyl, heteroaryl, arylalkyl, alkylthio, haloalkyl, haloalkyloxy, haloalkylthio, alkoxyalkyl, alkylthioalkyl, heteroarylalkyl, heterocyclylalkyl,
- Cycloalkylalkyl cycloalkenyl, alkynyl, alkenyl, haloalkenyl, haloalkynyl,
- R 5 and R 6 independently of one another represent hydrogen, halogen, alkyl, haloalkyl,
- R 7 represents hydrogen, halogen, alkyl, haloalkyl, haloalkoxy, haloalkoxyalkyl,
- R 6 and R 7 with the atoms to which they are attached form a completely saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring,
- R 8 is hydrogen, alkyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroarylalkyl, bis-arylalkyl, tris-arylalkyl, alkenyl, cycloalkenylalkyl, alkynylalkyl, trialkylsilylalkoxy kalk, alkoxyalkoxyalkyl, alkylthioalkyl, haloalkyl, arylsulfonylalkyl, trialkylsilyl, AI kyl- (bis-aryl) silyl, Al kyl- (bis-al kyl) silyl, bis-alkylaminoalkyl, heterocyclylalkyl, alkynyl, cyanoalkyl, heterocyclyl,
- R 9 is hydrogen, alkyl, cycloalkyl, halogen, alkynylalkyl, haloalkyl, alkynyl, alkenyl, cyanoalkyl, cycloalkylalkyl, arylalkyl, heteroarylalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkenylalkyloxycarbonyl,
- AI koxycarbonylcycloalkyl, hydroxycarbonylcycloalkyl
- Arylalkoxycarbonylcycloalkyl AI kenyloxycarbonylcycloalkyl
- AI kenyloxycarbonylheterocyclyl AI kenylal koxycarbonylheterocyclyl
- Cycloalkylaminocarbonylheterocyclyl arylalkylaminocarbonylheterocyclyl, alkenylaminocarbonylheterocyclyl, hydroxycarbonylheterocyclylalkyl,
- AI koxycarbonylheterocyclylalkyl, hydroxycarbonylcycloalkyl kylal
- AI koxycarbonylcycloal kylal kyl, hydroxy, alkoxy, heterocyclyl, heterocyclylalkyl,
- R 10 is hydrogen, alkyl, cycloalkyl, halogen, haloalkyl, alkynyl, alkenyl,
- Cyanoalkyl arylalkyl, heteroarylalkyl, alkylcarbonyl, alkoxycarbonyl,
- Cycloalkylsulfinyl, alkoxycarbonylalkyl, or R 9 and R 10 with the nitrogen to which they are attached are optionally halogen, alkyl, haloalkyl, alkoxy, alkoxycarbonyl, cycloalkoxycarbonyl, cycloalkylkoxycarbonyl, alkenyloxycarbonyl, hydroxycarbonyl,
- Arylalkylaminocarbonyl form substituted three to eight membered ring, which is optionally interrupted by O, S or N, or
- R 9 and R 10 together form part of an optionally substituted sulfilimine or amidine group or form an iminophosphorane and
- R 11 is hydrogen, alkyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl.
- the compounds of formula (I) can form salts. Salt formation can through
- Sulfonamide group contains -NHSO2-.
- suitable bases are organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular Sodium and potassium hydroxide, sodium and potassium carbonate and sodium and
- Hydrogen is replaced by a cation suitable for agriculture, for example metal salts, especially alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts, for example with cations of the formula [NRR'R "R"'] + , in which R 1 to R'"each independently of one another represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl, Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C 1 -C 4) -trialkylsulfonium and Ci-C4) -Trialkylsulfoxoniumsalze.
- metal salts especially alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary (quaternary) am
- R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 each have the meaning of the definitions below and wherein the arrow represents a bond to the respective moiety [XY],
- R 1 is hydrogen , (C 1 -C 8) alkyl, aryl, heteroaryl, heterocyclyl, (C3-C10) - cycloalkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (C 2 C 8 ) alkynyl (C 1 -C 8 ) alkyl, (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl, hydroxy (C 1 -C 8 ) alkyl, ( C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8
- R 2 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, ( C 3 -C 8 ) -cycloalkylcarbonyl,
- Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
- R 3 and R 4 are independently hydrogen, (C 1 -C 8) alkyl, halogen, (C 3 -C 8) - cycloalkyl, (C 1 -C 8) alkoxy, aryl, heterocyclyl, heteroaryl, aryl (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkyloxy, (C 1 -C 8 ) -haloalkylthio, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) - alkyl, heterocyclyl (C 1 -C 8 ) alkyl, (
- R 3 and R 4 with the atom to which they are attached form a completely saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring,
- R 5 and R 6 independently of one another represent hydrogen, halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) - Cycloalkyl- (C 1 -C 8 ) -alkyl,
- R 7 represents hydrogen, halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy, (C 1 -C 8 ) -haloalkoxy- (C 1 C 8 ) alkyl, (C 1 -C 8 ) haloalkoxy (C 1 -C 8 ) haloalkyl, (C 1 -C 8 ) alkoxy (C 1 -C 8 ) haloalkyl, (C 1 -C 8 ) -alkynyloxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkenyloxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkylthio, ( C 1 -C 8 ) haloalkylthio, optionally substituted
- R 6 and R 7 with the atoms to which they are attached form a completely saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring,
- R 8 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkyl, optionally substituted phenyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, bis-aryl- (C 1 C 8 ) alkyl, tris-aryl (C 1 -C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 4 -C 8 ) cycloalkenyl (C 1 -C 8 ) alkyl, ( C 2 -C 8 ) alkynyl (C 1 -C 8 ) alkyl, tri (C 1
- R 9 is hydrogen, (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, halogen, (C 2 -C 8 ) -alkynyl
- R 9 and R 10 with the nitrogen to which they are attached are optionally substituted by halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxycarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl, (C 3 -C 8 ) -cycloalkyl (C 1 -C 8 ) -alkoxycarbonyl, (C 2 -C 6 ) -alkenyloxycarbonyl, Hydroxycarbonyl, aminocarbonyl,
- R 9 and R 10 together form an N- (bis (C 1 -C 6 ) alkyl) sulfanylidene, N- (aryl- (C 1 -C 6 ) - alkyl) sulfanylidene, N- (bis (C 3 -C 7 ) cycloalkyl) sulfanylidene, N - ((C 1 -C 6 ) alkyl (C 3 -C 7 ) cycloalkyl) sulfanylidene group or an N , N-di (C 1 -C 6 ) alkylformylidene group and R 11 is hydrogen, (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 1 -C 8 ) -haloalkyl , (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl, (C 1 -C 8 ) alkyl
- R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each as defined below and wherein the arrow represents a bond to the respective grouping [XY],
- R 1 is hydrogen, (C 1 -C 7) alkyl, aryl, heteroaryl, heterocyclyl, (C3-C10) - cycloalkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl , (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, hydroxy (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkyl, (C 2 -C 7 ) Haloalkenyl, (C 1 -C 7 ) haloalkoxy (C 1 -C 7 ) alkyl, (C 1 -C 7 ) alkylthio (C 1 -C 7 ) alkyl, aryl (C 1 -C 7 ) -alkyl,
- R 2 is hydrogen, (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 1 -C 7 ) -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, ( C 3 -C 7 ) -cycloalkylcarbonyl, (C 2 -C 7 ) -alkenylcarbonyl, heterocyclylcarbonyl, (C 1 -C 7 ) -alkoxycarbonyl, (C 2 -C 7 ) -alkenyloxycarbonyl, aryloxy- (C 1
- a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
- Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
- R 3 and R 4 are independently hydrogen, (C 1 -C 7) alkyl, halogen, (C 3 -C 7) - cycloalkyl, (C 1 -C 7) alkoxy, aryl, heterocyclyl, heteroaryl, aryl (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkyloxy, (C 1 -C 7 ) -haloalkylthio, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) - alkyl, heterocyclyl (C 1 -C 7 ) alkyl, (
- R 7 represents hydrogen, halogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy, (C 1 -C 7 ) -haloalkoxy- (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 ) -Alkynyloxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -
- R 6 and R 7 form, with the atoms to which they are attached, a fully saturated, optionally heteroatom-interrupted and optionally further substituted 3 to 6-membered ring
- R 8 is hydrogen, (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, optionally substituted phenyl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkyl, bis-aryl- (C 1 -C 7 ) -alkyl, tris-aryl- (C 1 -) C 7 ) alkyl, (C 2 -C 7 ) alkenyl, (C 4 -C
- Alkylaminocarbonylheterocyclyl bis (C 1 -C 7 ) -alkylaminocarbonylheterocyclyl,
- Alkoxycarbonyl (C 3 -C 7 ) -cycloalkyl (C 1 -C 7 ) -alkyl, hydroxy, (C 1 -C 7 ) -alkoxy,
- R 10 is hydrogen, (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, halogen, (C 1 -C 7 ) -haloalkyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -alkenyl, cyano- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) Alkylcarbonyl, (C 1 -C 7 ) alkoxycarbonyl, (C 1 -C 7 ) - Alkylsulfonyl, arylsulfonyl, (C 3 -C 7 ) -cycloalkylsulfonyl, (C 1 -C 7 ) -alkylsulfinyl
- R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each as defined below and wherein the arrow represents a bond to the respective moiety [XY], is hydrogen, methyl , Ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl , 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1 , 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,
- I'-b is cyclopropyl ⁇ -yl, 1-cyanopropyl, 2-cyanopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1 Vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, ethenyl, 1-propenyl, 2-propenyl, 1- Methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propen
- Methoxyethoxyethyl methoxymethoxyethyl, ethoxy-n-propoxymethyl, ethoxy-n-propoxyethyl, ethoxyethoxymethyl, ethoxyethoxyethyl, is hydrogen, tert-butyldimethylsilyl, trimethylsilyl, triethylsilyl, tri (iso-propyl) silyl, tri (n-propyl) silyl , Dimethyl (phenyl) silyl, tert-butyldiphenylsilyl, dimethyl isopropylsilyl, isopropyldimethylsilyl, tert -hexyldimethylsilyl, 2- (trimethylsilyl) ethoxymethyl, 2- (trimethylsilyl) ethyl, methyl, ethyl, n-propyl, iso -propyl, n Butyl, iso-butyl
- a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
- Each oxygen or sulfur atoms are not adjacent, m is 0, 1, n is 0, 1,
- R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl , Cyclopentyl, cyclohexyl, cyclopropylcyclopropyl,
- Nonafluorobutyl chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2-dichloro-2-fluoroethyl, 2-chloro 2,2-difluoroethyl, difluoro-tert-butyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, difluoromethoxymethyl, difluoromethoxyethyl,
- Difluoromethoxy-n-propyl 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxyethyl, 2,2,2- Trifluoroethoxy-n-propyl, vinyl, prop-1-en-1-yl, but-1-en-1-yl, allyl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop -2-en-1-yl, but-2-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl, 2-methyl -prop-1 -en-1-yl, but-3-en-1-yl, Pentenyl, 2-methylpentenyl, hexenyl, ethynyl, propargyl, 1-methyl-prop-2-yn-1-yl, 2-butynyl
- R 3 and R 4 with the atom to which they are attached form a completely saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring,
- R 5 and R 6 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, n-butyl, isobutyl, isopropyl, n-pentyl, n-hexyl, isopentyl, Trifluoromethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl,
- R 7 represents hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl,
- R 9 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, halogen, (C 2 -C 6 ) -alkynyl
- R 10 is hydrogen, (C 1 -C 6) alkyl, (C3-C6) -cycloalkyl, halogen, (C 1 -C 6) -haloalkyl, (C 2 -C 6) -alkynyl, (C 2 - C 6 ) alkenyl, cyano (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkyl,
- Heteroaryl (C 1 -C 6) alkyl, (C 1 -C 6) alkylcarbonyl, (C 1 -C 6) Al koxycarbonyl, (C 1 -C 6) - alkylsulfonyl, arylsulfonyl, (C 3 -C 6 ) cycloalkylsulfonyl, (C 1 -C 6 ) -alkylsulfinyl,
- R 9 and R 10 with the nitrogen to which they are attached form a optionally substituted by fluorine, chlorine, bromine, iodine, (C 1 -C 6 J-alkyl, (C 1 -C 6) -haloalkyl, (C 1 -C 6 ) alkoxy,
- R 9 and R 10 together represent N- (di-n-butyl-sulfanylidene), N- (di-iso-propyl-sulfanylidene), N- (di-n-propyl-sulfanylidene), N- (di-n- pentyl-sulfanylidene), N- (di-isobutyl-sulfanylidene), N- (cyclobutyl-isopropyl-sulfanylidene), N- (n-propyl-isopropyl-sulfanylidene), N- (cyclopropyl-iso- propyl-sulfanylidene), N- (iso-butyl-isopropyl-sulfanylidene), ⁇ , ⁇ -dimethylformylidene, R 11 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl
- Heterocyclylcarbonyl methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyl, p-Cl-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthiomethyl, methylthioethyl,
- a 2 , V, W independently represent a group CR 3 R 4 , oxygen or
- Each oxygen or sulfur atoms are not adjacent, m is 0, 1, n is 0, 1,
- R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl,
- Trifluoromethoxyethyl trifluoromethoxy-n-propyl, difluoromethoxymethyl
- R 3 and R 4 with the atom to which they are attached form a fully saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring, and Q is one of the groups described in the following table Q-1.1 to Q-3.55 stands
- R 1 is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
- Methylpropyl 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,
- R 2 represents hydrogen, tert-butyldimethylsilyl, Trimethylsilyl, triethylsilyl, tri (iso -propyl) silyl, tri (n-propyl) silyl, dimethyl (phenyl) silyl, tert-butyldiphenylsilyl, diethylisopropylsilyl, isopropyldimethylsilyl, tert -hexyldimethylsilyl, 2- (trimethylsilyl) ethoxymethyl, 2 - (trimethylsilyl) ethyl, methyl,
- Heterocyclylcarbonyl methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyl, p-Cl-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthiomethyl, methylthioethyl,
- a 1 , V, W independently of one another represent a group CR 3 R 4 ,
- a 2 is a group CR 3 R 4 or oxygen, m is 0, n is 0, 1,
- R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Methoxy, optionally substituted phenyl, Heterocyclyl, heteroaryl, methylthio, trifluoromethyl, difluoromethyl, vinyl, prop-1-en-1-yl, but-1-en-1-yl, allyl, trifluoromethoxy, difluoromethoxy, 2,2-difluoroethoxy, 2,2,2- Trifluoroethoxy, trifluoromethylthio, methoxymethyl, ethoxymethyl,
- R 3 and R 4 with the atom to which they are attached form a fully saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring, and Q is one of the groups Q-1.1 described in the table above until Q-3.55
- Residue definitions apply both to the end products of the formula (I) and
- R 1 is hydrogen, (C 1 -C 8 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8 ) -cycloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl , (C 2 -C 8 ) -alkynyl (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy) (C 1 -C 8 ) -alkyl, HydrOxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 1 -C 8 ) - Haloalkoxy (C 1 -C 8 ) alkyl.
- R 2 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, ( C 3 -C 8 ) -cycloalkylcarbonyl, (C 2 -C 8 ) -alkenylcarbonyl, heterocyclylcarbonyl, (C 1 -C 8 ) -alkoxycarbonyl, (C 2 -C 8 ) --alkyl,
- a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
- Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
- R 3 and R 4 are independently hydrogen, (C 1 -C 8) alkyl, halogen, (C 3 -C 8) - cycloalkyl, (C 1 -C 8) alkoxy, aryl, heterocyclyl, heteroaryl, aryl (C 1 -C 8 ) -alkyl,
- R 1 is hydrogen, (C 1 -C 6 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl , (C 2 -C 6 ) -alkynyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -haloalkenyl,
- R 2 is hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, ( C 3 -C 6 ) -cycloalkylcarbonyl, (C 2 -C 6 ) -alkenylcarbonyl, heterocyclylcarbonyl, (C 1 -C 6 ) -alkoxycarbonyl, (C 2 -C 6 ) -alkenyloxycarbonyl, aryloxy- (C 1
- a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
- Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
- R 3 and R 4 are independently hydrogen, (C 1 -C 6) alkyl, halogen, (C 3 -C 6) - cycloalkyl, (C 1 -C 6) alkoxy, aryl, heterocyclyl, heteroaryl, aryl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkyloxy, (C 1 -C 6 ) -haloalkylthio, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) - alkyl, heterocyclyl - (C 1 -C 6 ) -al
- R 3 and R 4 with the atom to which they are attached form a completely saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring.
- R 1 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl , 1, 1-Dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1 , 2-Dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2 , 2-trimethylpropyl, 1-e
- R 2 is hydrogen, tert-butyldimethylsilyl, trimethylsilyl, triethylsilyl, tri (iso-propyl) silyl, tri (n-propyl) silyl, dimethyl (phenyl) silyl, tert-butyldiphenylsilyl, dimethyl isopropylsilyl, isopropyldimethylsilyl, tert Hexyldimethylsilyl, 2- (trimethylsilyl) ethoxymethyl, 2- (trimethylsilyl) ethyl, methyl, ethyl, allyl,
- Heterocyclylcarbonyl methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyl, p-Cl-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthiomethyl, methylthioethyl,
- a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
- Each oxygen or sulfur atoms are not adjacent, m is 0, 1, n is 0, 1,
- R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Methoxy, ethoxy, n-propoxy, isopropoxy, n-butyloxy, tert-butyloxy, iso-butyloxy, n-pentyloxy, optionally substituted phenyl, Heterocyclyl, heteroaryl, benzyl, p-CI-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio
- Trifluoromethoxyethyl trifluoromethoxy-n-propyl, difluoromethoxymethyl
- R 1 is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
- Cyclohexylmethyl optionally substituted phenyl, heteroaryl, Heterocyclyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5- yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl, bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.
- R 2 is hydrogen, tert-butyldimethylsilyl, trimethylsilyl, triethylsilyl, tri (iso-propyl) silyl, tri (n-propyl) silyl, dimethyl (phenyl) silyl, tert-butyldiphenylsilyl, dimethyl isopropylsilyl, isopropyldimethylsilyl, tert Hexyldimethylsilyl, 2- (trimethylsilyl) ethoxymethyl, 2- (trimethylsilyl) ethyl, methyl, ethyl, allyl,
- Heterocyclylcarbonyl methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyl, p-Cl-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthiomethyl, methylthioethyl,
- a 1 , V, W independently of one another are a group CR 3 R 4 , a group CR 3 R 4 or oxygen, m is 0, n is 0, 1,
- R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Methoxy, optionally substituted phenyl, heterocyclyl, heteroaryl, methylthio, trifluoromethyl, difluoromethyl, vinyl, prop-1-en-1-yl, but-1-en-1-yl, allyl, trifluoromethoxy, difluoromethoxy, 2,2-difluoroethoxy , 2,2,2-trifluoroethoxy, trifluoromethylthio, methoxy methyl, ethoxymethyl,
- R 3 and R 4 with the atom to which they are attached form a completely saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring.
- R 1 is hydrogen, (C 1 -C 8 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 8 ) -cycloalkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl , (C 2 -C 8 ) -alkynyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, hydroxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) alkylthio (C 1 -C 8) al
- R 2 is hydrogen, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, ( C 3 -C 8 ) -cycloalkylcarbonyl, (C 2 -C 8 ) -alkenylcarbonyl, heterocyclylcarbonyl, (C 1 -C 8 ) -alkoxycarbonyl, (C 2 -C 8 ) -alkenyloxycarbonyl, aryloxy- (C 1 -
- a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
- Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
- R 3 and R 4 are independently hydrogen, (C 1 -C 8) alkyl, halogen, (C 3 -C 8) - cycloalkyl, (C 1 -C 8) alkoxy, aryl, heterocyclyl, heteroaryl, aryl (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkyloxy, (C 1 -C 8 ) -haloalkylthio, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) - alkyl, heterocyclyl - (C 1 -C 8 ) -al
- R 1 is hydrogen, (C 1 -C 6 ) -alkyl, aryl, heteroaryl, heterocyclyl, (C 3 -C 6 ) -cycloalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl , (C 2 -C 6 ) -alkynyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, hydroxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -haloalkenyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) alkylthio (C 1 -C 6) al
- a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
- Each oxygen or sulfur atoms are not adjacent, m is 0, 1, 2, n is 0, 1, 2,
- R 3 and R 4 are independently hydrogen, (C 1 -C 6) alkyl, halogen, (C 3 -C 6) - cycloalkyl, (C 1 -C 6) alkoxy, aryl, heterocyclyl, heteroaryl, aryl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkyloxy, (C 1 -C 6 ) -haloalkylthio,
- R 3 and R 4 with the atom to which they are attached form a fully saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring, and [M] for tris - [(C 1 -C 6 ) -alkyl] stannyl, tris - [(C 3 -C 6 ) -cycloalkyl] stannyl, tris-KC 1 -C 6 ) -alkyl] germanyl, tris [ (C 3 -C 6 ) -cycloalkyl] germanyl, bis (cyclopentadienyl) zirconyl, bis (1, 2,3,4,5-pentamethylcyclopentadienyl) zirconyl, bis (cyclopentadienyl) hafnyl, bis (1, 2, 3,4,5
- R 1 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl , 1, 1-Dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1 , 2-Dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2 , 2-trimethylpropyl, 1-e
- R 2 is hydrogen, tert-butyldimethylsilyl, trimethylsilyl, triethylsilyl, tri (iso-propyl) silyl, tri (n-propyl) silyl, dimethyl (phenyl) silyl, tert-butyldiphenylsilyl, dimethyl isopropylsilyl, isopropyldimethylsilyl, tert Hexyldimethylsilyl, 2- (trimethylsilyl) ethoxymethyl, 2- (trimethylsilyl) ethyl, methyl, ethyl, allyl,
- Heterocyclylcarbonyl methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyl, p-Cl-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthiomethyl, methylthioethyl,
- a 1 , A 2 , V, W independently of one another for a group CR 3 R 4 , oxygen or
- Each oxygen or sulfur atoms are not adjacent, m is 0, 1, n is 0, 1, R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Methoxy, ethoxy, n-propoxy, isopropoxy, n-butyloxy, tert-butyloxy, iso-butyloxy, n-pentyloxy, optionally substituted phenyl,
- Trifluoromethoxyethyl trifluoromethoxy-n-propyl, difluoromethoxymethyl
- [M] is trimethylstannyl, triethylstannyl, tris (n-propyl) stannyl, tris (isopropyl) stannyl, tris (n-butyl) stannyl, tris (sec-butyl) stannyl, tris (tert-butyl)
- R 1 is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
- R 2 is hydrogen, tert-butyldimethylsilyl, trimethylsilyl, triethylsilyl, tri (iso-propyl) silyl, tri (n-propyl) silyl, dimethyl (phenyl) silyl, tert-butyldiphenylsilyl, dimethyl isopropylsilyl, isopropyldimethylsilyl, tert Hexyldimethylsilyl, 2- (trimethylsilyl) ethoxymethyl, 2- (trimethylsilyl) ethyl, methyl, ethyl, allyl,
- Heterocyclylcarbonyl methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, n-butyloxycarbonyl, isopropoxycarbonyl, isobutoxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyl, p-Cl-benzyl, pF-benzyl, p-methoxybenzyl, p-methylbenzyl, methylthiomethyl, methylthioethyl,
- a 1 , V, W independently of one another represent a group CR 3 R 4 ,
- a 2 is a group CR 3 R 4 or oxygen, m is 0, n is 0, 1, R 3 and R 4 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, fluorine, chlorine, bromine, iodine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Methoxy, optionally substituted phenyl, heterocyclyl, heteroaryl, methylthio, trifluoromethyl, difluoromethyl, vinyl, prop-1-en-1-yl, but-1-en-1-yl, allyl, trifluoromethoxy, difluoromethoxy, 2,2-difluoroethoxy , 2,2,2-trifluoroethoxy, trifluoromethylthio, methoxy methyl, ethoxymethyl,
- R 3 and R 4 with the atom to which they are attached form a fully saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 6-membered ring, and
- [M] is trimethylstannyl, triethylstannyl, tris (n-propyl) stannyl, tris (isopropyl) stannyl, tris (n-butyl) stannyl, tris (sec-butyl) stannyl, tris (tert-butyl) stannyl, tris (n-pentyl) stannyl, tris (n-hexyl) stannyl, for
- arylsulfonyl is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, here in particular optionally substituted naphthylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino,
- Alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups
- cycloalkylsulfonyl alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
- alkylsulfonyl alone or as part of a chemical group - represents straight-chain or branched alkylsulfonyl, preferably having 1 to 8, or having 1 to 6 carbon atoms such as methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl , sec-butylsulfonyl and tert-butylsulfonyl.
- heteroarylsulfonyl is optionally substituted
- substituted polycyclic heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino,
- alkylcarbonylamino, dialkylamino or alkoxy groups alkylcarbonylamino, dialkylamino or alkoxy groups.
- alkylthio alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n- Butylthio, isobutylthio, sec-butylthio and tert-butylthio.
- Alkenylthio represents an alkenyl radical bonded via a sulfur atom
- alkynylthio represents an alkynyl radical bonded via a sulfur atom
- cycloalkylthio represents a cycloalkyl radical bonded via a sulfur atom
- cycloalkenylthio represents a cycloalkenyl radical bonded via a sulfur atom
- Alkoxy represents an alkyl radical bonded via an oxygen atom
- alkenyloxy denotes an alkynyl radical bound via an oxygen atom
- alkynyloxy denotes an alkynyl radical bound via an oxygen atom
- cycloalkyloxy denotes a cycloalkyl radical bonded via an oxygen atom
- cycloalkenyloxy denotes a cycloalkenyl radical bonded via an oxygen atom.
- aryl means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
- optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, the binding site being on the aromatic system.
- Aryl is also generally known from the term “optionally substituted phenyl ".
- heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
- heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 6
- Ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two oxygen atoms should be directly adjacent, as
- 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 - or 2- or 3- or 4- or
- 5- or 6-yl 5,6-dihydro-4H-1,2-oxazine-3- or 4- or 5- or 6-yl; 2H-1, 2-oxazine-2 or 3 or 4 or 5 or 6-yl; 6H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 4H-1, 2-oxazine-3 or 4 or 5 or 6-yl; 1,3-oxazinan-2 or 3 or 4 or 5 or 6-yl;
- 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-
- heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, 1, 4,2-dioxazolidin-2 or 3 or 5-yl; 1, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,2,2,2-dioxazine-3- or 5- or 6-yl; 1,2,2-dioxazine-3- or 5- or 6-yl; 1, 4,2-Dioxazepan-2 or 3 or 5 or
- heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl,
- Oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
- lactones and lactams are preferably also included.
- the oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. in the case of N and S, for example, the divalent groups N (O), S (O) (also known as SO) and S (O) 2 (also abbreviated to SO 2) occur and form in the heterocyclic ring.
- N (O) also known as SO
- S (O) 2 also abbreviated to SO 2
- Heteroaryls of the invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazol-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1, 2,3-triazole 5-yl, 2H-1, 2,3-triazol-2-yl, 2H-1, 2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-yl
- heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, these are annelated heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
- quinolines for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinoline-7 yl, quinolin-8-yl
- Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
- quinoxaline for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinoline-7 yl, quinolin-8-yl
- quinoxaline e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-
- quinazoline cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
- pyridopyrimidines Pyridopyridazine; pteridines; Pyrimidopyrimidine.
- Heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1 H-indol-1-yl, I H -indol-2-yl, I H -indol-3-yl, 1 H-indol-4-yl, 1H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl , 1-Benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1 Benzothiophene-5-yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazol-1-yl, 1H-
- halogen means, for example, fluorine, chlorine, bromine or iodine.
- halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
- alkyl means a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted and is referred to in the latter case as “substituted alkyl”.
- Substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio,
- Haloalkylthio, amino or nitro groups particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine.
- Haloalkyl means the same or different
- Polyhaloalkyl such as CH 2 CHFCI, CF 2 CCIFH, CF 2 CBrFH, CH 2 CF 3 ;
- perhaloalkyl also encompasses the term perfluoroalkyl.
- Partially fluorinated alkyl means a straight-chain or branched, saturated
- Hydrocarbon which is mono- or polysubstituted by fluorine, wherein the corresponding fluorine atoms as substituents on one or more
- Hydrocarbon chain can be located, such as. B. CHFCH 3 , CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3
- Partially fluorinated haloalkyl means a straight-chain or branched, saturated hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom , all other possibly existing ones
- Halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
- the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
- Partially fluorinated haloalkyl also includes the
- Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl;
- (C 1 -C 4) -alkyl given here by way of example means a
- Carbon atoms corresponding to the range for C atoms, ie, the radicals include methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
- General alkyl radicals having a larger specified range of carbon atoms eg. B. "(C 1 -C 6 ) -alkyl”, accordingly also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, ie according to Example, the alkyl radicals with 5 and 6 C atoms.
- hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are lower
- Carbon skeletons e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred.
- Alkyl radicals also in the assembled radicals such as alkoxy, haloalkyl, etc., mean e.g.
- Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or triple bond.
- alkenyl in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds such as allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
- Alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, eg prop-1-en-1 yl, but-1-en-1-yl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-ene-1 yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl, 2-methyl-prop-1-en-1-yl,
- alkynyl in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yne 1-yl.
- C 2 -C 6 ) -alkynyl is, for example, ethynyl, propargyl, 1-methyl-prop-2-yn-1-yl, 2-butynyl,
- 2-pentynyl or 2-hexynyl preferably propargyl, but-2-yn-1-yl, but-3-yn-1-yl or 1-methyl-but-3-yn-1-yl.
- cycloalkyl means a carbocyclic, saturated and optionally substituted ring system having preferably 3-8 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
- substituents wherein also
- substituted cycloalkyl are also spirocyclic aliphatic
- Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, eg 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2- Cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein also substituents having a double bond on the cycloalkenyl radical, for example a
- Alkylidene group such as methylidene, are included. In case of if necessary
- Cycloalkyl identi means a carbocyclic radical which is bonded via a double bond.
- stannyl represents a further substituted radical which is a tin atom "Germanyl” is analogous to a further substituted radical, the one
- Zeroconyl represents a further substituted radical containing a zirconium atom.
- Hafnyl represents a further substituted radical containing a hafnium atom.
- Boryl represents a further substituted radical containing a hafnium atom.
- Boryl is further substituted and optionally cyclic groups, each containing a boron atom.
- Plumbanyl represents a further substituted radical containing a lead atom.
- Haldrargyl represents a further substituted radical containing a mercury atom.
- Alignyl represents a further substituted radical containing an aluminum atom.
- Magnnesyl represents a further substituted radical containing a magnesium atom.
- Zincyl represents a further substituted radical containing a zinc atom.
- the compounds of the general formula (I) can exist as stereoisomers.
- the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
- Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods. The chromatographic separation can be used both on an analytical scale for
- stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
- the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof.
- the substituted cyano-cycloalkylpenta-2,4-dienes according to the invention, cyano-cycloalkylpent-2-en-4-enes, cyano-heterocyclylpenta-2,4-dienes and cyano-cyclohexanone Heterocyclylpent-2-en-4-ines of the general formula (I) can be prepared by known methods.
- the known and structurally related natural plant substance abscisic acid can be obtained on various synthetic routes (see Hanson et al., J. Chem. Res. (S), 2003, 426; Constantino et al., J. Org. Chem. 1986, 51, 253; Constantino et al., 1989, 54, 681; Marsh et al., Org. Biomol.
- the first key intermediate for the synthesis of the compounds of the general formula (I) according to the invention is an optionally further substituted 1- (2-hydroxybut-3-yn-2-yl) cycloalkylcarbonitrile of the general formula (II).
- Solvent eg tetrahydrofuran or in two steps by reaction with trimethylsilylacetylene and LDA (lithium diisopropylamide) in a temperature range from -78 ° C to 0 ° C in a suitable polar aprotic solvent (eg.
- Tetrahydrofuran and subsequent cleavage of the trimethylsilyl group with the aid of a suitable trialkylammonium fluoride (eg tetrabutylammonium fluoride) in a polar aprotic solvent or with a suitable carbonate base (eg.
- a suitable trialkylammonium fluoride eg tetrabutylammonium fluoride
- a suitable carbonate base eg.
- a 1 , A 2 , V, W, R 1 , R 2 , R 5 , R 6 , R 7 and R 8 in the following Scheme 2 have the meanings defined above.
- substituted cyano-cycloalkylpent-2-en-4-ene-1 (a) according to the invention can also be obtained by reaction of a suitable substituted ketone with
- Transition metal-catalyzed coupling of a trialkylsilyl alkyne and a (Z) -iodoalkanoic acid derivative (compare J. Chem. Res. (S), 2003, 426, J. Chem. Soc, Perkin Trans., 2001, 47) using a suitable palladium catalyst (for example bis (triphenylphosphine) palladium dichloride) and a suitable copper (I) halide (eg copper (I) iodide) in a suitable solvent mixture of an amine and a polar aprotic solvent (eg diisopropylamine and toluene or
- EDC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide
- HOBt stands for hydroxybenzotriazole in this context.
- R 5 , R 6 , R 7 , R 8 , R 9 and R 10 have in the following Scheme 3 the meanings defined above.
- the substituted cyano-cycloalkylpent-2-en-4-carboxylic acid amides 1 (b) according to the invention are therefore accessible via two possible synthetic routes (Scheme 4), a) the conversion of the substituted cyano-cycloalkylpent-2-en-4-amino acids 1 ( a) by reaction with thionyl chloride and
- a suitable palladium catalyst eg bis (triphenylphosphine) palladium dichloride
- a suitable copper (I) halide eg copper (I) iodide
- a suitable solvent mixture of an amine and a polar aprotic solvent eg diisopropylamine and toluene or triethylamine and tetrahydrofuran.
- a 1 , A 2 , V, W, R 1 , R 2 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 and m and n have the previously defined meanings in the following Scheme 4.
- the substituted (E, Z) -configured cyano-cycloalkylpenta-2,4-dienes 1 (c) according to the invention can be prepared by reducing the alkyne group of the inventive
- lithium dissolved in a mixture of ethylamine and tert-butanol eg Helvetica Chimica Acta 1986, 69, 368
- a suitable trialkoxysilane in the presence of a suitable transition metal catalyst (eg tris (acetonitrile) ruthenium 1, 2,3,4,5-pentamethylcyclopentadienylhexafluoro-phosphate or tris (acetonitrile) ruthenium-cyclopentadienylhexafluorophosphate, see J. Am.
- a suitable transition metal catalyst eg tris (acetonitrile) ruthenium 1, 2,3,4,5-pentamethylcyclopentadienylhexafluoro-phosphate or tris (acetonitrile) ruthenium-cyclopentadienylhexafluorophosphate, see J. Am.
- substituted 1 - [(3E) -2-hydroxy-4- [M] -but-3-en-2-yl] cycloalkylcarbonitriles may be prepared by coupling with a corresponding substituted (Z) -haloalkanoic acid derivative in a suitable solvent (e.g. Tetrahydrofuran or ⁇ , ⁇ -dimethylformamide) using appropriate
- Transition metal catalysts e.g., bis (triphenylphosphine) palladium dicyanide, tetrakis (triphenylphosphine) palladium or bis (triphenylphosphine) palladium dichloride
- E, Z -configured cyano-cycloalkylpenta-2,4-dienes of this invention (c ) (Scheme 6).
- a 1 , A 2 , V, W, [M], R 1 , R 2 , R 5 , R 6 , R 7 and R 8, and m and n have the meanings defined above in the following Scheme 6.
- Transition-metal catalyst such as Lindlars catalyst with hydrogen in a suitable polar aprotic solvent (such as n-butanol) (see Tetrahedron 1987, 43, 4107, Tetrahedron 1983, 39, 2315, J. Org. Synth. 1983, 48, 4436 and J. Am. Chem. Soc. 1984, 106, 2735) (Scheme 9).
- a suitable polar aprotic solvent such as n-butanol
- Transition metal catalysts eg bis (triphenylphosphine) palladium dicyanide
- Example numbers given correspond to the numbering mentioned in Tables 1 to 5 below.
- N-cyclopropylpent-2-ynamide (1 equiv) was concentrated in conc.
- Dissolved acetic acid (2 ml / mmol) treated with finely powdered sodium iodide (3 equiv) and stirred for 4 hours at a temperature of 110 ° C.
- MTBE methyl tert-butyl ether
- the aqueous phase was extracted several times with MTBE and the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
- ethyl (2Z) -6- (1-cyancyclopropyl) -6-hydroxy-3-methyl-6-phenylhex-2-ene-4-ynate (320 mg, 42% of theory ) isolated in the form of a colorless oil.
- Ethyl 3-ethylprop-2-ynate (700 mg, 5.55 mmol) was concentrated in conc. Acetic acid (7 ml) was added, mixed with finely powdered sodium iodide (2.49 g, 16.65 mmol) and stirred at a temperature of 110 ° C for 3 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated sodium thiosulfate solution. The aqueous phase was extracted several times with MTBE and the combined organic phases dried over magnesium sulfate, filtered and under
- Methyl pent-2-inoate 14.48 mmol was concentrated in conc. Acetic acid (15 ml) was added, mixed with finely powdered sodium iodide (43.43 mmol) and stirred at a temperature of 110 ° C for 3 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated sodium thiosulfate solution. The aqueous phase was extracted several times with MTBE and the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product
- reaction mixture was stirred for 3 hours at room temperature and then treated with water.
- the aqueous phase was extracted several times with dichloromethane.
- the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
- Methyl pent-2-inoate 14.48 mmol was concentrated in conc. Acetic acid (15 ml) was added, mixed with finely powdered sodium iodide (43.43 mmol) and stirred at a temperature of 110 ° C for 3 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated sodium thiosulfate solution. The aqueous phase was extracted several times with MTBE and the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product
- Pent-2-carboxylic acid (1500 mg, 15.2 mmol) was concentrated in conc. Acetic acid (15 ml) was added, mixed with finely powdered sodium iodide (6876 mg, 45.8 mmol) and stirred at a temperature of 110 ° C for 3 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated
- Methyl 4,4,4-trifluorobut-2-ynate 500 mg, 3.01 mmol was concentrated in conc. Acetic acid (6 ml) was added, mixed with finely powdered sodium iodide (1353 mg, 9.03 mmol) and stirred at a temperature of 110 ° C for 4 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated
- Ethyl 2-butynoate (3.00 g, 26.76 mmol) was concentrated in conc.
- Acetic acid 25 ml was dissolved, mixed with finely powdered sodium iodide (12.03 g, 80.27 mmol) and stirred at a temperature of 110 ° C for 3 h.
- MTBE methyl tert-butyl ether
- the aqueous phase was extracted several times with MTBE and the combined organic phases dried over magnesium sulfate, filtered and under
- Methyl 4,4,4-trifluorobut-2-ynate 500 mg, 3.01 mmol was concentrated in conc. Acetic acid (6 ml) was added, mixed with finely powdered sodium iodide (1353 mg, 9.03 mmol) and stirred at a temperature of 110 ° C for 4 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated
- Methyl pent-2-inoate 14.48 mmol was concentrated in conc. Acetic acid (15 ml) was added, mixed with finely powdered sodium iodide (43.43 mmol) and stirred at a temperature of 110 ° C for 3 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated sodium thiosulfate solution. The aqueous phase was extracted several times with MTBE and the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product
- Methyl 4,4,4-trifluorobut-2-ynate 500 mg, 3.01 mmol was concentrated in conc. Acetic acid (6 ml) was added, mixed with finely powdered sodium iodide (1353 mg, 9.03 mmol) and stirred at a temperature of 110 ° C for 4 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated
- Ethyl 4,4,4-trifluorobut-2-ynoate 500 mg, 3.01 mmol was concentrated in conc.
- Acetic acid (6 ml) was added, mixed with finely powdered sodium iodide (1353 mg, 9.03 mmol) and stirred at a temperature of 110 ° C for 4 h.
- Methyl 4,4,4-trifluorobut-2-ynate 500 mg, 3.01 mmol was concentrated in conc. Acetic acid (6 ml) was added, mixed with finely powdered sodium iodide (1353 mg, 9.03 mmol) and stirred at a temperature of 110 ° C for 4 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated
- Methyl pent-2-inoate 14.48 mmol was concentrated in conc. Acetic acid (15 ml) was added, mixed with finely powdered sodium iodide (43.43 mmol) and stirred at a temperature of 110 ° C for 3 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated sodium thiosulfate solution. The aqueous phase was extracted several times with MTBE and the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product
- reaction mixture was stirred for 3 hours at room temperature and then treated with water.
- the aqueous phase was extracted several times with dichloromethane.
- the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
- Methyl 4,4,4-trifluorobut-2-ynate 500 mg, 3.01 mmol was concentrated in conc. Acetic acid (6 ml) was added, mixed with finely powdered sodium iodide (1353 mg, 9.03 mmol) and stirred at a temperature of 110 ° C for 4 h. After cooling to room temperature, the addition of methyl tert-butyl ether (MTBE) and saturated
- Residue was treated 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. By column chromatographic purification of the crude product obtained (gradient ethyl acetate / heptane) 1 - (3-hydroxy-4-methylpent-1 -yn-3-yl) cyclopropanecarbonitrile (2.59 g, 54% of theory) was isolated as a colorless solid.
- Residue was treated 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. Purification by column chromatography of the crude product obtained (gradient ethyl acetate / heptane) isolated 1- (1-cyclopentyl-1-hydroxyprop-2-yn-1-yl) cyclopropanecarbonitrile (2.55 g, 25% of theory) as a colorless solid.
- Residue was treated 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. By column chromatographic purification of the resulting crude product (gradient ethyl acetate / heptane) 1 - (1-hydroxy-1-phenylprop-2-yn-1-yl) cyclobutancarbonitril (740 mg, 6% of theory) was isolated as a colorless waxy solid.
- Tetrakis (triphenylphosphine) palladium (0) (198 mg, 0.17 mmol) was placed under argon in a heated round bottom flask and washed with abs. Tetrahydrofuran (20 ml) and 1- (3-hydroxy-4-methylpent-1-yn-3-yl) cyclopropanecarbonitrile (560 mg, 3.41 mmol) were added. After stirring for 5 minutes at room temperature, the addition of
- No. III.1 -5 1 - [(2E) -1-Cyclopropyl-1-hydroxy-3- (tributylstannyl) prop-2-en-1-yl] cyclopropanecarbonitrile
- Tetrakis (triphenylphosphine) palladium (0) (107 mg, 0.09 mmol) was placed under argon in a heated round bottom flask and washed with abs.
- Tetrahydrofuran (10 ml) and 1- (1-cyclopropyl-1-hydroxyprop-2-yn-1-yl) cyclopropanecarbonitrile (370 mg, 2.29 mmol) were added.
- tributyltin hydride (0.74 ml, 2.75 mmol) was added.
- the resulting reaction mixture was stirred for 1 hour at room temperature and for 30 minutes at a temperature of 50 ° C and then added with water.
- the aqueous phase was extracted several times thoroughly with dichloromethane and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated under reduced pressure.
- No. III.1-76 1 - [(2E) -1-cyclopentyl-1-hydroxy-3- (tributylstannyl) prop-2-en-1-yl] cyclopropanecarbonitrile
- Tetrakis (triphenylphosphine) palladium (0) (464 mg, 0.40 mmol) was placed under argon in a baked round bottom flask and washed with abs. Tetrahydrofuran (30 ml) and 1- (1-cycloentyl-1-hydroxyprop-2-yn-1-yl) cyclopropanecarbonitrile (1900 mg, 10.04 mmol) were added. After stirring for 5 minutes at room temperature, the addition of
- Tetrakis (triphenylphosphine) palladium (0) (242 mg, 0.21 mmol) was placed under argon in a baked round bottom flask and washed with abs. Tetrahydrofuran (20 ml) and 1- (4-ethyl-3-hydroxyhex-1-yn-3-yl) cyclopropanecarbonitrile (1.00 g, 5.23 mmol) were added. After stirring for 5 minutes at room temperature, the addition of
- No. III.2-2 1 - [(1E) -3-hydroxy-4-methyl-1- (tributylstannyl) pent-1-en-3-yl] cyclobutanecarbonitrile
- Tetrakis (triphenylphosphine) palladium (0) (261 mg, 0.23 mmol) was placed under argon in a heated round bottom flask and washed with abs. Tetrahydrofuran (20 ml) and 1- (3-hydroxy-4-methylpent-1-yn-3-yl) cyclobutanecarbonitrile (1000 mg, 5.64 mmol) were added. After stirring for 5 minutes at room temperature, the addition of
- Another object of the present invention is the use of at least one compound of the invention selected from the group consisting of substituted cyano-cycloalkylpenta-2,4-serve and cyano-cycloalkylpent-2-en-4-inden of the general formula (I), and of any mixtures of these
- Plant growth and / or increase the plant yield Plant growth and / or increase the plant yield.
- a further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
- Stress conditions may include, for example, heat, drought, cold and dry stress (stress caused by drought and / or lack of water), osmotic stress,
- Nitrogen nutrients limited availability of phosphorus nutrients.
- Cyano-cycloalkylpenta-2,4-dienes substituted according to the invention, cyano-cycloalkylpent-2-en-4-enes, cyano-heterocyclylpenta-2,4-dienes and cyano-heterocyclylpent-2-en-4-ines of the general formula (I ) are applied by spray application to appropriate plants or plant parts to be treated.
- the use according to the invention of the compounds of the general formula (I) or salts thereof is preferably carried out with a dosage of between 0.00005 and 3 kg / ha, more preferably between 0.0001 and 2 kg / ha,
- the term resistance or resistance to abiotic stress is understood to mean various advantages for plants. Such advantageous properties are manifested, for example, in the following improved plant characteristics: improved root growth in terms of surface area and depth, increased lagging or tillering, stronger and more productive shoots and tillers,
- Photosynthesis beneficial plant properties, such as
- Non-limiting resistance to abiotic stress ⁇ at least one in general 3%, in particular greater than 5%
- At least one leaf area increased by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
- a further subject of the present invention is a spray solution for the treatment of plants, comprising an amount of at least one effective for increasing the resistance of plants to abiotic stress factors
- the spray solution may have other common ingredients, such as solvents,
- Formulation aids especially water, included.
- Other ingredients may include agrochemical agents, which are further described below.
- Another object of the present invention is the use of
- inventive compounds of the general formula (I) per se and for the corresponding spray solutions are inventive compounds of the general formula (I) per se and for the corresponding spray solutions.
- Fertilizers which, according to the invention, can be used together with the compounds of the general formula (I) according to the invention which are explained in more detail above, are generally organic and inorganic nitrogen-containing compounds of the general formula (I) according to the invention which are explained in more detail above, are generally organic and inorganic nitrogen-containing compounds of the general formula (I) according to the invention which are explained in more detail above, are generally organic and inorganic nitrogen-containing compounds of the general formula (I) according to the invention which are explained in more detail above, are generally organic and inorganic nitrogen-containing
- Phosphoric acid preferably potassium salts and ammonium salts.
- NPK fertilizers ie fertilizers
- Ammonium nitrate (general formula (NH 4 ) 2 SO 4 ) contains nitrogen, phosphorus and potassium, calcium ammonium nitrate, ie fertilizers which still contain calcium
- the fertilizers may also contain salts of micronutrients (preferably calcium,
- Fertilizers used according to the invention may also contain other salts such as monoammonium phosphate (MAP), diammonium phosphate (DAP), potassium sulfate,
- fertilizers Containing potassium chloride, magnesium sulfate. Suitable amounts for the secondary nutrients or trace elements are amounts of 0.5 to 5 wt .-%, based on the total fertilizer.
- Further possible ingredients are crop protection agents, insecticides or fungicides, growth regulators or mixtures thereof. Further explanations follow below.
- the fertilizers can be used, for example, in the form of powders, granules, prills or compactates. However, the fertilizers can also be used in liquid form dissolved in an aqueous medium. In this case, dilute aqueous ammonia can be used as nitrogen fertilizer. Further possible ingredients for fertilizers are, for example, in Ullmann's
- the general composition of the fertilizers which in the context of the present invention may be single-nutrient and / or complex nutrient fertilizers,
- nitrogen, potassium or phosphorus may vary within a wide range.
- a content of 1 to 30 wt .-% of nitrogen preferably 5 to 20 wt .-%), from 1 to 20 wt .-% potassium (preferably 3 to 15% by weight) and a content of 1 to 20% by weight of phosphorus (preferably 3 to 10% by weight) is advantageous.
- the content of microelements is usually in the ppm range, preferably in the range of from 1 to 1000 ppm.
- the fertilizer and one or more compounds of the general formula (I) according to the invention can be administered at the same time.
- Embodiments of the present invention use one or more compounds of the formula (I) and the fertilizer according to the invention in a time frame of less than 1 hour, preferably less than 30 minutes, more preferably less than 15 minutes.
- the forest stock includes trees for the production of wood, pulp, paper and products made from parts of the trees.
- crops as used herein refers to
- Among the useful plants include z.
- the following plant species Triticale, Durum
- Durum wheat turf, vines, cereals, such as wheat, barley, rye, oats, rice, corn and millet
- Beets for example sugar beets and fodder beets
- Fruits such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, eg. Strawberries, raspberries, blackberries
- Legumes such as beans, lentils, peas and soybeans
- Oil crops such as oilseed rape, mustard, poppy, olives, sunflowers, coconut,
- Castor oil plants cocoa beans and peanuts; Cucumber plants, for example Pumpkin, cucumbers and melons; Fiber plants, for example cotton, flax, hemp and jute; Citrus fruits, such as oranges, lemons, grapefruit and mandarins; Vegetables such as spinach, (head) salad, asparagus, cabbages, carrots, onions, tomatoes, potatoes and peppers; Laurel family, such as avocado, cinnamomum, camphor, or plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, vines, hops, bananas,
- Natural rubber plants and ornamental plants such as flowers, shrubs, deciduous trees and conifers such as conifers. This list is not a limitation.
- Particularly suitable target crops for the application of the method according to the invention are the following plants: oats, rye, triticale, durum, cotton, aubergine, turf, pome fruit, stone fruit, berry fruit, corn, wheat, barley, cucumber, tobacco, vines, rice, cereals , Pear, pepper, beans, soybeans, rape, tomato, paprika, melons, cabbage, potato and apple.
- Examples of trees which can be improved according to the method of the invention are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp , Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.
- trees which can be improved according to the method of the invention, may be mentioned: From the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Picea: P. abies; from the tree Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P.
- albicaulis P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E.
- the present invention may also be practiced on any turfgrasses, including "cool season turfgrasses” and “warm season turfgrasses.”
- cold season turf species are blue grasses (Poa spp.), Such as “Kentucky bluegrass” (Poa pratensis L), “rough bluegrass” (Poa trivialis L), “Canada bluegrass” (Poa compressa L), “annual bluegrass” (Poa annua L), “upland bluegrass” (Poa glaucantha Gaudin), “Wood bluegrass” (Poa nemoralis L.) and “bulbous bluegrass” (Poa bulbosa L); ostrich grasses ("Bentgrass”, Agrostis spp.), Such as “creeping bentgrass” (Agrostis palustris Huds.), “Colonial bentgrass” (Agrostis Tenuis Sibth.), “velvet bentgrass” (Agrostis canina L),
- Fescue Fescues, Festucu spp.
- red fescue Festuca rubra L. spp. Rubra
- creeping fescue Festuca rubra L
- chewings fescue Festuca rubra commutata Gaud.
- Sheep fescue (Festuca ovina L),” hard fescue “(Festuca longifolia Thuill.),” hair fescue “(Festucu capillata Lam.),” tall fescue “(Festuca arundinacea Schreb.) and” meadow fescue "(Festuca elanor L) ;
- Lolium ryegrasses, Lolium spp.
- Examples of other "cool season turfgrasses” are “beachgrass” (Ammophila breviligulata Fern.), “Smooth bromegrass” (Bromus inermis leyss.), Reeds ("cattails") such as “Timothy” (Phleum pratense L.), “sand cattail “(Phleum subulatum L.) “orchardgrass” (Dactylis glomerata L.), “weeping alkaligrass” (Puccinellia distans (L.) Pari.) and “crested dog's-tail” (Cynosurus cristatus L.).
- Examples of “warm season turfgrasses” are “Bermudagrass” (Cynodon spp., LC Rieh), “zoysiagrass” (Zoysia spp. Willd.), “St. Augustine grass” (Stenotaphrum secundatum Walt Kuntze), “centipedegrass” (Eremochloa ophiuroides Munrohack.), “Carpetgrass” (Axonopus affin is Chase), “Bahia grass” (Paspalum notatum flügge), “Kikuyugrass” (Pennisetum clandestinum detergent, ex Chiov.), “Buffalo grass” (Buchloe daetyloids (Nutt.) Engelm. ), “Blue gramma” (Bouteloua gracilis (HBK) lag.
- Bermudagrass Cronodon spp., LC Rieh
- Plant varieties are understood to be plants with new traits which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. Crop plants can accordingly 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 transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
- the treatment method according to the invention can thus also for the treatment of genetically modified organisms (GMOs), z.
- GMOs genetically modified organisms
- Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
- heterologous gene essentially means a gene that is provided or assembled outside the plant and that when introduced into the plant
- a heterologous gene present in the genome is also referred to as a transgene.
- a transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
- Compounds of general formula (I) include all plants which have genetic material conferring on these plants particularly advantageous, useful characteristics (whether obtained by breeding and / or biotechnology).
- Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are resistant to one or more abiotic stress factors. To the abiotic stress factors,
- Stress conditions can include, for example, heat, drought, cold and dry stress, osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade.
- Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are characterized by increased yield properties. An increased yield can in these plants z. B. on improved plant physiology, improved
- Plant growth and improved plant development such as
- the yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for the production of hybrid seed,
- Root growth seed size, fruit size, pod size, pods or Ear number, number of seeds per pod or ear, seed mass, strengthened
- Stability Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of nontoxic compounds, improved processability, and improved shelf life.
- Plants which can also be treated with the compounds of the general formula (I) according to the invention are hybrid plants which have already been used
- Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossbred partner).
- the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
- Pollen sterile plants can sometimes be produced (eg in maize) by delaving (i.e., mechanically removing male genitalia or male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
- the desired product as one wants to harvest from the hybrid plants, is the seeds, it is usually beneficial to ensure that the pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility , completely restored. This can be accomplished by ensuring that the male crossbred partners possess appropriate fertility restorer genes capable of controlling pollen fertility in humans
- Pollen sterility may be localized in the cytoplasm.
- CMS cytoplasmic male sterility
- Brassica species WO 92/005251, WO 95/009910, WO 98/27806, WO2005 / 002324, WO2006 / 021972 and US 6,229,072
- genetic determinants of pollen sterility may also be localized in the nuclear genome.
- Pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering.
- a ribonuclease such as a barnase is selectively expressed in the tapetum cells in the stamens.
- the fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 91/002069).
- Plants or plant varieties which are obtained by plant biotechnology methods, such as genetic engineering), which also with the inventive
- herbicide-tolerant plants d. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.
- Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, i. H.
- glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS).
- EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
- Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371), the CP4 gene of the bacterium
- Agrobacterium sp. Barry et al., Curr Topics Plant Physiol. (1992), 7, 139-145
- the genes responsible for petunia EPSPS (Shah et al., Science (1986), 233, 478-481).
- an EPSPS from the tomato Gasser et al., J. Biol. Chem. (1988), 263, 4280-4,289) or for an EPSPS from Eleusine (WO2001 / 66704).
- It can also be a mutated EPSPS, as described, for example, in EP-A 0837944, WO 00/066746, WO 2000/66747 or WO2002 / 026995.
- Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme as described in US Pat
- Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in e.g. WO2002 / 036782,
- Glyphosate-tolerant plants can also be obtained by Plants which select for naturally occurring mutations of the abovementioned genes, as described, for example, in WO2001 / 024615 or WO2003 / 013226.
- Other herbicide-resistant plants are, for example, plants opposite
- Herbicides that inhibit the enzyme glutamine synthase such as bialaphos, phosphinotricin or glufosinate, have been tolerated. Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
- an effective detoxifying enzyme is, for example, an enzyme suitable for
- Phosphinotricin acetyltransferase encoded such as the bar or pat protein from Streptomyces species. Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US 5,739,082; US 5,908,810 and US 7,112,665.
- hydroxyphenylpyruvate dioxygenase HPPD
- HPPD hydroxyphenylpyruvate dioxygenases
- HPPD inhibitors may be treated with a gene encoding a naturally occurring resistant HPPD enzyme, or a gene encoding a mutant HPPD enzyme as described in WO 96/038567, WO 99/024585 and WO 99/1998 / 024586, are transformed.
- Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 99/034008 and WO 2002/36787.
- the tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene which codes for an HPPD-tolerant enzyme, with a gene which codes for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described.
- Other herbicide-resistant plants are plants that have been tolerated to acetolactate synthase (ALS) inhibitors. Examples of known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines,
- Acetohydroxy acid synthase known
- Sulfonylurea and imidazolinone tolerant plants are also useful in e.g. WHERE
- Imidazolinones, sulfonylureas and / or sulfamoylcarbonyltriazolinones can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding, as for example for the soybean in US 5,084,082, for rice in WO 97/41218, for the sugar beet in US 5,773,702 and WO 99/057965, for salad in US 5,198,599 or for the sunflower in WO 2001/065922.
- Plants or plant varieties obtained by plant biotechnology methods, such as genetic engineering), which are also with the inventive
- insect-resistant transgenic plants ie plants that have been made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
- insect-resistant transgenic plant as used herein includes any plant containing at least one transgene comprising a coding sequence encoding:
- an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof such as the insecticidal crystal proteins collected by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature (online at:
- insecticidal parts thereof e.g. Proteins of Cry protein classes CrylAb, CrylAc, Cryl F, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or 2) a crystal protein from Bacillus thuringiensis or a part thereof which is present in
- Presence of a second, different crystal protein than Bacillus thuringiensis or a part thereof is insecticidal, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Moellenbeck et al., Nat. Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environment Microb. (2006) 71, 1765-1774); or
- an insecticidal hybrid protein comprising parts of two different insecticides of Bacillus thuringiensis crystal proteins, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g.
- the protein Cry1A.105 produced by the corn event MON98034 WO
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Abstract
Description
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PCT/EP2015/066402 WO2016012362A1 (de) | 2014-07-22 | 2015-07-17 | Substituierte cyano-cycloalkylpenta-2,4-diene, cyano-cycloalkylpent-2-en-4-ine, cyano-heterocyclylpenta-2,4-diene und cyano-heterocyclylpent-2en-4-ine als wirkstoffe gegen abiotischen pflanzenstress |
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- 2015-07-17 CA CA2955798A patent/CA2955798A1/en not_active Abandoned
- 2015-07-17 EP EP15738663.2A patent/EP3172187A1/de not_active Withdrawn
- 2015-07-17 WO PCT/EP2015/066402 patent/WO2016012362A1/de active Application Filing
- 2015-07-17 US US15/327,714 patent/US10322995B2/en not_active Expired - Fee Related
- 2015-07-17 BR BR112017001144-1A patent/BR112017001144A2/pt not_active IP Right Cessation
- 2015-07-17 JP JP2017503161A patent/JP2017528432A/ja not_active Ceased
- 2015-07-17 AU AU2015294110A patent/AU2015294110B2/en not_active Expired - Fee Related
- 2015-07-17 TW TW104123312A patent/TW201617311A/zh unknown
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AU2015294110B2 (en) | 2019-11-21 |
AU2015294110A1 (en) | 2017-02-02 |
TW201617311A (zh) | 2016-05-16 |
US20170210701A1 (en) | 2017-07-27 |
CA2955798A1 (en) | 2016-01-28 |
AR101214A1 (es) | 2016-11-30 |
JP2017528432A (ja) | 2017-09-28 |
WO2016012362A1 (de) | 2016-01-28 |
BR112017001144A2 (pt) | 2018-01-30 |
US10322995B2 (en) | 2019-06-18 |
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