WO2013092943A1 - Isothiazoline compounds for combating invertebrate pests - Google Patents
Isothiazoline compounds for combating invertebrate pests Download PDFInfo
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- WO2013092943A1 WO2013092943A1 PCT/EP2012/076539 EP2012076539W WO2013092943A1 WO 2013092943 A1 WO2013092943 A1 WO 2013092943A1 EP 2012076539 W EP2012076539 W EP 2012076539W WO 2013092943 A1 WO2013092943 A1 WO 2013092943A1
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- Prior art keywords
- alkyl
- compounds
- ring
- group
- cycloalkyl
- Prior art date
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- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 41
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical class C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 1115
- 238000000034 method Methods 0.000 claims abstract description 60
- 239000000463 material Substances 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 23
- -1 C2-C4- haloalkenyl Chemical group 0.000 claims description 747
- 125000005842 heteroatom Chemical group 0.000 claims description 262
- 125000001424 substituent group Chemical group 0.000 claims description 245
- 150000003254 radicals Chemical class 0.000 claims description 208
- 229910052739 hydrogen Inorganic materials 0.000 claims description 200
- 125000000623 heterocyclic group Chemical group 0.000 claims description 197
- 239000001257 hydrogen Substances 0.000 claims description 195
- 229910052717 sulfur Inorganic materials 0.000 claims description 157
- 150000002431 hydrogen Chemical group 0.000 claims description 149
- 229910052760 oxygen Inorganic materials 0.000 claims description 142
- 229910052736 halogen Inorganic materials 0.000 claims description 133
- 150000002367 halogens Chemical group 0.000 claims description 133
- 229920006395 saturated elastomer Polymers 0.000 claims description 107
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 106
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 105
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 86
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 72
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 69
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 68
- 229910052757 nitrogen Inorganic materials 0.000 claims description 59
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 52
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 125000001931 aliphatic group Chemical group 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 46
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 42
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 239000002243 precursor Substances 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 16
- 229940000425 combination drug Drugs 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 13
- 238000005576 amination reaction Methods 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 10
- 238000005580 one pot reaction Methods 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
- 206010061217 Infestation Diseases 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 239000002689 soil Substances 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 238000009395 breeding Methods 0.000 claims description 7
- 230000001488 breeding effect Effects 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 150000002466 imines Chemical class 0.000 claims description 7
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- 238000003682 fluorination reaction Methods 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 239000012025 fluorinating agent Substances 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 claims description 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004766 (C3-C6) cyclohaloalkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 claims 1
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 claims 1
- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 241000244206 Nematoda Species 0.000 abstract description 15
- 241000238421 Arthropoda Species 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 235000013350 formula milk Nutrition 0.000 description 505
- 241000196324 Embryophyta Species 0.000 description 61
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 description 60
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- 239000002904 solvent Substances 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 23
- 239000003053 toxin Substances 0.000 description 23
- 150000001412 amines Chemical class 0.000 description 22
- 239000002585 base Substances 0.000 description 22
- 231100000765 toxin Toxicity 0.000 description 22
- 108700012359 toxins Proteins 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- 108090000623 proteins and genes Proteins 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 102000004169 proteins and genes Human genes 0.000 description 16
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 229910052794 bromium Inorganic materials 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
- 235000018102 proteins Nutrition 0.000 description 14
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 13
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- 239000003112 inhibitor Substances 0.000 description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 13
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 12
- 150000001721 carbon Chemical group 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
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- 230000000749 insecticidal effect Effects 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
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- 229940052303 ethers for general anesthesia Drugs 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
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- 125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 description 6
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
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- DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 5
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- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 5
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- 125000000547 substituted alkyl group Chemical group 0.000 description 5
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- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 4
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- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 1
- 125000000232 haloalkynyl group Chemical group 0.000 description 1
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004761 hexafluorosilicates Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 125000004282 imidazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])N([H])C1([H])* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 1
- 125000004285 isoxazolidin-3-yl group Chemical group [H]N1OC([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 108010080576 juvenile hormone esterase Proteins 0.000 description 1
- 239000002523 lectin Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 235000020667 long-chain omega-3 fatty acid Nutrition 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- VLGWYKOEXANHJT-UHFFFAOYSA-N methylsulfanol Chemical compound CSO VLGWYKOEXANHJT-UHFFFAOYSA-N 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 108091040857 miR-604 stem-loop Proteins 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 102000035118 modified proteins Human genes 0.000 description 1
- 108091005573 modified proteins Proteins 0.000 description 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006093 n-propyl sulfinyl group Chemical group 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
- 239000002581 neurotoxin Substances 0.000 description 1
- 231100000618 neurotoxin Toxicity 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
- SJECIYLGISUNRO-UHFFFAOYSA-N o-diphenylphosphorylhydroxylamine Chemical compound C=1C=CC=CC=1P(=O)(ON)C1=CC=CC=C1 SJECIYLGISUNRO-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 238000006772 olefination reaction Methods 0.000 description 1
- 235000021315 omega 9 monounsaturated fatty acids Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000004288 oxazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC1([H])* 0.000 description 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 235000019834 papain Nutrition 0.000 description 1
- 229940055729 papain Drugs 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 239000003726 plant lectin Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000004481 post-translational protein modification Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004673 propylcarbonyl group Chemical group 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 108020001580 protein domains Proteins 0.000 description 1
- 125000004290 pyrazolidin-3-yl group Chemical group [H]N1N([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000037359 steroid metabolism Effects 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000004300 thiazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])SC1([H])* 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- 125000004569 thiomorpholin-2-yl group Chemical group N1CC(SCC1)* 0.000 description 1
- 125000004570 thiomorpholin-3-yl group Chemical group N1C(CSCC1)* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical compound CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- AECHPKVYOLOZLF-UHFFFAOYSA-N trifluoro(phenyl)-$l^{4}-sulfane Chemical compound FS(F)(F)C1=CC=CC=C1 AECHPKVYOLOZLF-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—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
- A01N43/80—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
Definitions
- the present invention relates to isothiazoline compounds which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes, and to a method for producing them.
- the invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.
- Invertebrate pests and in particular arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating invertebrate pests, in particular insects, arachnids and nematodes.
- the object of the present invention was moreover to provide compounds which are less persistent, bioaccumulative and/or toxic than the compounds of the prior art. Especially isoxazoline insecticides show a high persistency in the soil and thus accumulate there. It has been found that these objectives can be achieved by isothiazoline compounds of the formula I below, by their steroisomers and by their salts, in particular their agriculturally or veterinarily acceptable salts.
- the invention relates to isothiazoline compounds of formula I
- A is a group A 1 , A 2 , A 3 or A 4 ;
- a 2 is a group of following formula:
- W is selected from O and S;
- Y is selected from hydrogen, -N(R 5 )R 6 and -OR 9 ; is a group of following formula:
- # denotes the bond to the aromatic ring of formula (I); is a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2, 3 or 4 heteroa- toms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, or is a 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2, 3 or 4 heteroa- toms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic or heterobicyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substitu- ents R 11 ;
- B 1 , B 2 and B 3 are each independently selected from the group consisting of N and CR 2 , with the proviso that at most two of B 1 , B 2 and B 3 are N;
- G 1 , G 2 , G 3 and G 4 are each independently selected from the group consisting of N and CR 4 , with the proviso that at most two of G 1 , G 2 , G 3 and G 4 are N;
- phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 11 , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heteromono- or heterobicyclic ring may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 11 ;
- R 3a , R 3b are each independently selected from the group consisting of hydrogen, halogen, -C0 2 R 3d , hydroxyl, Ci-C 3 -alkyl, d-C 3 -haloalkyl, C 2 -C 3 -alkenyl, C 2 -C 3 - alkynyl, Ci-C 3 -alkoxy, Ci-C 3 -haloalkoxy, Ci-C 3 -alkylthio, Ci-C 3 -haloalkylthio, Ci- C 3 -alkylsulfonyl and Ci-C 3 -haloalkylsulfonyl; or
- R 4 is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, -SCN, -SF 5 , Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 8 , Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 8 , C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 8 , C2- C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 8 ,
- phenyl which may be substituted by 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , radicals R 11 , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 11 ; each R 5 is independently selected from the group consisting of hydrogen, C1-C10- alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last- mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or
- each R 6 is independently selected from the group consisting of hydrogen, cyano, Ci- Cio-alkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, wherein the four last- mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 8 ,
- R 7a , R 7b are each independently selected from the group consisting of hydrogen, halogen, cyano, Ci-C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 8 ; each R 8 is independently selected from the group consisting of cyano, azido, nitro, - SCN, -SF 5 , C3-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 13 ;
- phenyl optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , and
- a 3-, 4-, 5-, 6- or 7- membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , or
- R 8 together with the carbon atoms of an alkyl, alkenyl, alkynyl or cycloalkyi group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ; and
- R 8 as a substituent on a cycloalkyi ring is additionally selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl and C2-C6-haloalkynyl, where the aliphatic moieties in these six radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 13 ; and
- R 9 is independently selected from the group consisting of hydrogen, cyano, Ci- Ce-alkyl, Ci-C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-Ci-C 4 -alkyl-, C 3 -C 8 - halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, where the aliphatic and cydoaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 3 ,
- phenyl optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ;
- a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ; and
- R 9 in the groups -S(0) n R 9 and -OSO2R 9 is additionally selected from the group consisting of Ci-C6-alkoxy and Ci-C6-haloalkoxy;
- phenyl optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ;
- a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ;
- R 10a and R 10b form together with the nitrogen atom they are bonded to a 3-, 4- , 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-
- radicals R 8 1 , 2 or 3, in particular 1 , radicals R 8 ,
- phenyl optionally substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents selected independently from R 16 ;
- a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated aromatic heterocyclic ring comprising 1 , 2, 3 or 4 heteroatoms or het- eroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected independently from R 16 ;
- R 11 bound on adjacent ring atoms form together with the ring atoms to which they are bound a saturated 3-, 4-, 5-, 6-, 7-, 8- or 9-membered ring, where- in the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from
- R 12 is independently selected from the group consisting of hydrogen, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxy-Ci-C6- alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-haloalkoxy-Ci- C6-alkyl, and phenyl, optionally substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, preferably 1 or 2, in particular 1 , substituents R 16 ;
- R 13 is independently selected from the group consisting of cyano, nitro, -OH, -SH, -SCN, -SF 5 , d-Ce-alkoxy, Ci-C 6 -haloalkoxy, Ci-C 6 -alkylthio, Ci-C 6 - haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci- C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, ferf-butyldimethylsilyl,
- Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo; phenyl, benzyl, phenoxy, where the phenyl moiety in the three last-mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, more preferably 1 or 2, in particular 1 , substituents R 16 ; and a 3-, 4-, 5-, 6- or 7- membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may
- R 13 as a substituent on a cycloalkyl ring is additionally selected from the group consisting of Ci-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl, wherein the three last- mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , substituents selected from CN, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;
- R 14 is independently selected from the group consisting of hydrogen, cyano, Ci C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, C1-C6- alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from CN , Ci-C4-alkoxy, C1-C4- hal
- Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, C3-C4- cycloalkyl, C3-C4-cycloalkyl-Ci-C4-alkyl-, where the cycloalkyl moiety in the two last-mentioned radicals may be substituted by 1 or 2, in particular 1 , substituents selected from halogen and cyano; and oxo;
- cyclic moieties in the four last- mentioned radicals may be unsubstituted and/or carry 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy,
- Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 or 2 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more substituents R 16 ;
- R 14a and R 14b independently of each other, have one of the meanings given for R 14 ;
- R 14a and R 14b together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, preferably 1 , 2 or 3, in particular 1 , substitutents selected from halogen, Ci-C4-alkyl, Ci- C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
- phenyl, benzyl, pyridyl and phenoxy wherein the four last-mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3, preferably 1 or 2 in particular 1 , substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl;
- R 16 is independently selected from the group consisting of halogen, nitro, cyano, -OH, -SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci- C6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, feri-butyldimethylsilyl;
- Cs-Cs-cycloalkyI which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2, in particular 1 , radicals selected from Ci-C4-alkyl, C3-C4- cycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy and oxo;
- phenyl, benzyl, pyridyl and phenoxy wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1 , 2 or 3, in particular 1 , substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy and (Ci-C6-alkoxy)carbonyl;
- two R 16 on two adjacent carbon atoms form together with the carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, and wherein the ring optionally carries one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci- C4-haloalkoxy; each n is independently 0, 1 or 2; and
- each m is independently 0 or 1 ; and the N-oxides, stereoisomers and agriculturally or veterinarily acceptable salts thereof.
- the present invention also provides an agricultural composition comprising at least one compound of the formula I as defined herein and/or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.
- the present invention also provides a veterinary composition comprising at least one compound of the formula I as defined herein and/or a veterinarily acceptable salt thereof and at least one liquid or solid carrier.
- the present invention also provides a method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a cultivated plant, plant propagation materials (such as seed), soil, area, material or environment in which the pests are growing or may grow, or the materials, cultivated plants, plant propagation materials (such as seed), soils, surfaces or spaces to be protected from pest attack or infestation with a pesticidally effective amount of a compound of formula I or a salt thereof as defined herein.
- the present invention also relates to plant propagation material, in particular seed, comprising at least one compound of formula I and/or an agriculturally acceptable salt thereof as defined herein.
- the present invention further relates to a method for treating or protecting an animal from infestation or infection by parasites which comprises bringing the animal in contact with a parasiticidally effective amount of a compound of the formula I or a veterinarily acceptable salt thereof as defined herein. Bringing the animal in contact with the compound I, its salt or the veterinary composition of the invention means applying or administering it to the animal.
- steroisomers encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
- the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
- One center of chirality is the carbon ring atom of the isothiazoline ring carrying radical R 1 .
- the invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantio- mers or diastereomers of the compound I or its mixtures.
- Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.
- N-oxides relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO).
- the compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have a different macroscopic properties such as stability or show different biological properties such as activities.
- the present invention includes both amorphous and crystalline compounds of the formula I, mixtures of different crystalline states of the respective compound I, as well as amorphous or crystalline salts thereof.
- Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.
- Suitable agriculturally acceptable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
- Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH 4+ ) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy- Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl.
- substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammo- nium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetrae- thylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxy- ethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
- Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyr- ate. They can be formed by reacting a compound of formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
- Suitable acid addition salts e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochloride, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.
- inorganic acids for example hydrochloride, sulphates, phosphates, and nitrates
- organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid.
- invertebrate pest encompasses animal populations, such as insects, arachnids and nematodes, which may attack plants, thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded animals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.
- plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil.
- the plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting. Said young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
- plants comprises any types of plants including "non-cultivated plants” and in particular "cultivated plants”.
- non-cultivated plants refers to any wild type species or related species or related genera of a cultivated plant.
- cultiva plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf.
- Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
- Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
- auxin herbicides
- herbicides e. bromoxynil or ioxynil herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made re- sistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci.
- cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield ® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.
- plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as ⁇ - endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp.
- VIP1 , VIP2, VIP3 or VIP3A vegetative insecticidal proteins
- toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
- toxins produced by fungi such Streptomy- cetes toxins, plant lectins, such as pea or barley lectins; agglutinins
- proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
- ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
- steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
- ion channel blockers such as blockers of sodium
- these insecticidal proteins or toxins are to be understood ex- pressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
- Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ).
- Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073.
- the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g.
- insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
- Genetically modified plants capable to synthesize one or more insecticidal proteins are, e.
- WO 03/018810 MON 863 from Monsan- to Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
- plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called " pathogenesis-related proteins" (PR proteins, see, e. g.
- EP-A 392 225 plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
- plant disease resistance genes e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum
- T4-lysozym e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora.
- the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications men- tioned above.
- plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), toler- ance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
- productivity e. g. bio mass production, grain yield, starch content, oil content or protein content
- plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health- promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ® rape, DOW Agro Sciences, Canada).
- plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora ® potato, BASF SE, Germany).
- the organic moieties mentioned in the above definitions of the variables are - like the term halogen - collective terms for individual listings of the individual group members.
- the prefix C n -C m indicates in each case the possible number of carbon atoms in the group.
- halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.
- alkyl as used herein and in the alkyl moieties of alkoxy, alkylthio, alkylsulfi- nyl, alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl and the like refers to saturated straight- chain or branched hydrocarbon radicals having 1 to 2 ("Ci-C2-alkyl"), 1 to 3 (“C1-C3- alkyl"),1 to 4 (“Ci-C 4 -alkyl”), 1 to 6 (“Ci-C 6 -alkyl”), 1 to 8 (“Ci-C 8 -alkyl”) or 1 to 10 (“Ci- Cio-alkyl”) carbon atoms.
- Ci-C2-Alkyl is methyl or ethyl.
- Ci-C3-Alkyl is additionally propyl and isopropyl.
- Ci-C 4 -Alkyl is additionally butyl, 1 -methylpropyl (sec-butyl), 2- methylpropyl (isobutyl) or 1 ,1 -dimethylethyl (tert-butyl).
- Ci-C6-Alkyl is additionally also, for example, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 - ethylpropyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 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, or 1 - eth
- Ci-Cs-Alkyl is additionally also, for example, heptyl, octyl, 2- ethylhexyl and positional isomers thereof.
- Ci-Cio-Alkyl is additionally also, for example, nonyl, decyl and positional isomers thereof.
- haloalkyl as used herein, which is also expressed as “alkyl which is partially or fully halogenated”, refers to straight-chain or branched alkyl groups having 1 to 2 (“Ci-C 2 -haloalkyl”), 1 to 3 (“Ci-C 3 -haloalkyl”), 1 to 4 (“Ci-C 4 -haloalkyl”), 1 to 6 (“Ci-C 6 - haloalkyl”), 1 to 8 (“Ci-C 8 -haloalkyl”) or 1 to 10 (“Ci-Cio-haloalkyl”) carbon atoms (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above: in particular Ci-C2-haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluorome- thyl, trifluoromethyl, chlorofluoromethyl,
- Ci-C3-haloalkyl is additionally, for example, 1 -fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1 ,1 -difluoropropyl, 2,2- difluoropropyl, 1 ,2-difluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoro- propyl, 1 ,1 ,1 -trifluoroprop-2-yl, 3-chloropropyl and the like.
- Examples for C1-C4- haloalkyl are, apart those mentioned for Ci-C3-haloalkyl, 4-chlorobutyl and the like.
- Halomethyl is methyl in which 1 , 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like.
- alkenyl refers to monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 3 (“C2-C3-alkenyl"), 2 to 4 (“C 2 -C4-alkenyl”), 2 to 6 (“C 2 -C 6 -alkenyl”), 2 to 8 (“C 2 -C 8 -alkenyl”) or 2 to 10 (“C 2 -Cio-alkenyl”) carbon atoms and a double bond in any position, for example C 2 -C3-alkenyl, such as ethenyl, 1 -propenyl, 2-propenyl or 1 -methylethenyl; C 2 -C4-alkenyl, such as ethenyl, 1 -propenyl,
- haloalkenyl as used herein, which is also expressed as “alkenyl which is partially or fully halogenated”, refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 (“C 2 -C 4 -haloalkenyl"), 2 to 6 (“C 2 -C 6 -haloalkenyl”), 2 to 8 (“C2-C6-haloalkenyl”) or 2 to 10 (“C2-Cio-haloalkenyl”) carbon atoms and a double bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.
- alkynyl refers to straight-chain or branched hydrocarbon groups having 2 to 3 (“C 2 -C 3 -alkynyl”), 2 to 4 (“C 2 -C 4 -alkynyl”), 2 to 6 (“C 2 -C 6 -alkynyl”), 2 to 8 (“C 2 -C8-alkynyl”), or 2 to 10 (“C 2 -Cio-alkynyl”) carbon atoms and one or two triple bonds in any position, for example C 2 -C3-alkynyl, such as ethynyl, 1 -propynyl or 2- propynyl; C 2 -C 4 -alkynyl, such as ethynyl, 1 -propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -methyl-2-propynyl and the like, C
- cycloalkyl refers to mono- or bi- or polycyclic saturated hydrocarbon radicals having 3 to 8 (“Cs-Cs-cycloalkyl”), in particular 3 to 6 carbon atoms (“C3-C6-cycloalkyl”).
- monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
- monocyclic radicals having 3 to 8 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
- bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.2.1 ]heptyl, bicyclo[3.1 .1]heptyl, bicyclo[2.2.2]octyl and bicy- clo[3.2.1 ]octyl.
- cycloalkyl denotes a monocyclic saturated hydrocarbon radical.
- halocydoalkyl as used herein, which is also expressed as “cycloalkyl which is partially or fully halogenated”, refers to mono- or bi- or polycyclic saturated hydrocarbon groups having 3 to 8 (“Cs-Cs-halocycloalkyl” ) or preferably 3 to 6 (“C3-C6- halocycloalkyl”) carbon ring members (as mentioned above) in which some or all of the hydrogen atoms are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.
- cycloalkyl-Ci-C4-alkyl refers to a Cs-Cs-cycloalkyl group ("Cs-Cs-cycloalkyl- Ci-C4-alkyl”), preferably a C3-C6-cycloalkyl group ("C3-C6-cycloalkyl-Ci-C4-alkyl”), more preferably a C3-C4-cycloalkyl group (“C3-C4-cycloalkyl-Ci-C4-alkyl”) as defined above (preferably a monocyclic cycloalkyl group) which is bound to the remainder of the mol- ecule via a Ci-C4-alkyl group, as defined above.
- Examples for C3-C4-cycloalkyl-Ci-C4- alkyl are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutyl methyl, cy- clobutylethyl and cyclobutylpropyl,
- Examples for C3-C6-cycloalkyl-Ci-C4-alkyl, apart those mentioned for C3-C4-cycloalkyl-Ci-C4-alkyl, are cyclopentylmethyl, cyclopen- tylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylpropyl.
- C3-C8-halocycloalkyl-Ci-C4-alkyl refers to a Cs-Cs-halocycloalkyl group as defined above which is bound to the remainder of the molecule via a Ci-C4-alkyl group, as defined above.
- Ci-C2-alkoxy is a Ci-C2-alkyl group, as defined above, attached via an oxygen atom.
- Ci-C3-alkoxy is a Ci-C3-alkyl group, as defined above, attached via an oxygen atom.
- Ci-C4-alkoxy is a Ci-C4-alkyl group, as defined above, attached via an oxygen atom.
- Ci-C6-alkoxy is a Ci-C6-alkyl group, as defined above, attached via an oxygen atom.
- Ci-Cio-alkoxy is a Ci-Cio-alkyl group, as defined above, attached via an oxygen atom.
- Ci-C2-Alkoxy is methoxy or ethoxy.
- Ci-C3-Alkoxy is additionally, for example, n-propoxy and 1 -methylethoxy (iso- propoxy).
- Ci-C4-Alkoxy is additionally, for example, butoxy, 1 -methylpropoxy (sec- butoxy), 2-methylpropoxy (isobutoxy) or 1 ,1 -dimethylethoxy (tert-butoxy).
- Ci-C6-Alkoxy is additionally, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethyl propoxy, hexoxy, 1 -methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 - dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3- dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2- trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1 -ethyl-1-methylpropoxy or 1 -ethyl-2- methylpropoxy.
- Ci-Cs-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2- ethylhexyloxy and positional isomers thereof.
- Ci-Cio-Alkoxy is additionally, for example, nonyloxy, decyloxy and positional isomers thereof.
- Ci-C2-haloalkoxy is a Ci-C2-haloalkyl group, as defined above, attached via an oxygen atom.
- Ci-C3-haloalkoxy is a Ci-C3-haloalkyl group, as defined above, attached via an oxygen atom.
- Ci-C4-haloalkoxy is a Ci-C4-haloalkyl group, as defined above, attached via an oxygen atom.
- Ci-C6-haloalkoxy is a Ci-C6-haloalkyl group, as defined above, attached via an oxygen atom.
- Ci- Cio-haloalkoxy is a Ci-Cio-haloalkyl group, as defined above, attached via an oxygen atom.
- Ci-C 2 -Haloalkoxy is, for example, OCH 2 F, OCHF 2 , OCF 3 , OCH 2 CI, OCHCI 2 , OCC , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2- trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2- fluoroethoxy, 2,2,2-trichloroethoxy or OC 2 F 5 .
- Ci-C3-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy,
- Ci-C4-Haloalkoxy is additionally, for example, 4-fluorobutoxy, 4-chlorobutoxy, 4- bromobutoxy or nonafluorobutoxy.
- Ci-C6-Haloalkoxy is additionally, for example, 5- fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.
- Ci-C4-alkoxy-Ci-C4-alkyl refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C4-alkoxy group, as defined above.
- Ci-C4-alkoxy group refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms, as defined above, where one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above.
- Examples are methoxymethyl, ethoxyme- thyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec-butoxymethyl, isobu- toxymethyl, tert-butoxymethyl, 1 -methoxyethyl, 1 -ethoxyethyl, 1 -propoxyethyl, 1 - isopropoxyethyl, 1 -n-butoxyethyl, 1 -sec-butoxyethyl, 1 -isobutoxyethyl, 1 -tert- butoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-n- butoxyethyl, 2-sec-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, 1 -methoxypropyl, 1 -ethoxypropyl, 1 -propoxyprop
- Ci-C6-alkoxy-methyl refers to methyl in which one hydrogen atom is replaced by a Ci-C6-alkoxy group, as defined above. Examples are methox- ymethyl, ethoxymethyl, propoxymethyl, isopropoxymethyl, n-butoxymethyl, sec- butoxymethyl, isobutoxymethyl, tert-butoxymethyl, pentyloxymethyl, hexyloxymethyl and the like.
- Ci-C4-Haloalkoxy-Ci-C4-alkyl is a straight-chain or branched alkyl group having from 1 to 4 carbon atoms, wherein one of the hydrogen atoms is replaced by a Ci-C4-alkoxy group and wherein at least one, e.g. 1 , 2, 3, 4 or all of the remaining hydrogen atoms (either in the alkoxy moiety or in the alkyl moiety or in both) are replaced by halogen atoms.
- Examples are difluoro- methoxymethyl (CHF2OCH2), trifluoromethoxymethyl, 1 -difluoromethoxyethyl , 1 - trifluoromethoxyethyl, 2-difluoromethoxyethyl, 2-trifluoromethoxyethyl, difluoro- methoxy-methyl (CH3OCF2), 1 ,1 -difluoro-2-methoxyethyl, 2,2-difluoro-2-methoxyethyl and the like.
- Ci-C2-alkylthio is a Ci-C2-alkyl group, as defined above, attached via a sulfur atom.
- Ci-C3-alkylthio is a Ci-C3-alkyl group, as defined above, attached via a sulfur atom.
- Ci-C4-alkylthio is a Ci-C4-alkyl group, as defined above, attached via a sulfur atom.
- Ci-C6-alkylthio is a Ci-C6-alkyl group, as defined above, attached via a sulfur atom.
- Ci-Cio-alkylthio is a Ci-Cio-alkyl group, as defined above, attached via a sulfur atom.
- Ci-C2-Alkylthio is methylthio or ethylthio.
- Ci-C3-Alkylthio is additionally, for example, n-propylthio or 1 -methylethylthio (iso- propylthio).
- Ci-C4-Alkylthio is additionally, for example, butylthio, 1 -methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1 ,1 -dimethylethylthio (tert-butylthio).
- Ci-C6-Alkylthio is additionally, for example, pentylthio, 1 -methylbutylthio,
- Ci-Cs- Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.
- Ci-Cio-Alkylthio is additionally, for example, nonylthio, decylthio and positional isomers thereof.
- Ci-C2-haloalkylthio is a Ci-C2-haloalkyl group, as defined above, attached via a sulfur atom.
- Ci-C3-haloalkylthio is a Ci-C3-haloalkyl group, as defined above, attached via a sulfur atom.
- Ci-C4-haloalkylthio is a Ci-C4-haloalkyl group, as defined above, attached via a sulfur atom.
- Ci-C6-haloalkylthio is a Ci-C6-haloalkyl group, as defined above, attached via a sulfur atom.
- Ci-C 2 -Haloalkylthio is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfur atom.
- Ci-C 2 -Haloalkylthio is, for example, SCH 2 F, SCHF 2 , SCF 3 , SCH 2 CI, SCHC , SCCI 3 , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2- fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2- difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2- difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-t
- C1-C3- Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2- difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3- dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio,
- Ci-C4-Haloalkylthio is additionally, for example, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio.
- Ci-C6-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6- chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio.
- C 1 -C2-a I ky Is u If i nyl is a Ci-C2-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
- Ci-C4-alkylsulfinyl is a Ci-C4-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
- Ci-C6-alkylsulfinyl is a C1-C6- alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
- C1-C10- alkylsulfinyl is a Ci-Cio-alkyl group, as defined above, attached via a sulfinyl [S(O)] group.
- Ci-C2-Alkylsulfinyl is methylsulfinyl or ethylsulfinyl.
- nyl is additionally, for example, n-propylsulfinyl, 1 -methylethylsulfinyl (isopropylsulfinyl), butyl- sulfinyl, 1 -methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfi- nyl) or 1 ,1 -dimethylethylsulfinyl (tert-butylsulfinyl).
- Ci-C6-Alkylsulfinyl is additionally, for example, pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3- methylbutylsulfinyl, 1 ,1 -dimethylpropylsulfinyl, 1 ,2-dimethylpropylsulfinyl,
- Ci-Ce-Alkylsulfinyl is additionally, for example, heptylsulfinyl, octylsulfinyl, 2- ethylhexylsulfinyl and positional isomers thereof.
- Ci-Cio-Alkylsulfinyl is additionally, for example, nonylsulfinyl, decylsulfinyl and positional isomers thereof.
- the term "Ci-C2-haloalkylsulfinyl” is a Ci-C2-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
- the term "Ci-C4-haloalkylsulfinyl” is a Ci-C4-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
- C1-C6- haloalkylsulfinyl is a Ci-C6-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
- Ci-Cio-haloalkylsulfinyl is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfinyl [S(O)] group.
- Ci-C2-Haloalkylsulfinyl is, for example, S(0)CH 2 F, S(0)CHF 2 , S(0)CF 3 , S(0)CH 2 CI, S(0)CHCI 2 , S(0)CCI 3 , chlorofluorome- thylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2- fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2- difluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, 2-chloro-2-fluoroethylsulfinyl, 2-chloro- 2,2-difluoroethylsulfinyl, 2,2-dichloro-2-
- Ci-C4-Haloalkylsulfinyl is additionally, for example, 2-fluoropropylsulfinyl, 3- fluoropropylsulfinyl, 2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,
- C1-C6- Haloalkylsulfinyl is additionally, for example, 5-fluoropentylsulfinyl, 5- chloropentylsulfinyl, 5-brompentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfi- nyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl.
- Ci-C2-alkylsulfonyl is a Ci-C2-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
- Ci-C3-alkylsulfonyl is a Ci-C3-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
- Ci-C4-alkylsulfonyl is a C1-C4- alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
- C1-C6- alkylsulfonyl is a Ci-C6-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
- Ci-Cio-alkylsulfonyl is a Ci-Cio-alkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
- Ci-C2-Alkylsulfonyl is methylsulfonyl or ethyl- sulfonyl.
- Ci-C3-Alkylsulfonyl is additionally, for example, n-propylsulfonyl or 1 - methylethylsulfonyl (isopropylsulfonyl).
- Ci-C4-Alkylsulfonyl is additionally, for example, butylsulfonyl, 1 -methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobu- tylsulfonyl) or 1 ,1 -dimethylethylsulfonyl (tert-butylsulfonyl).
- Ci-C6-Alkylsulfonyl is addi- tionally, for example, pentylsulfonyl, 1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3- methylbutylsulfonyl, 1 ,1 -dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl,
- d-Cs-Alkylsulfonyl is additionally, for example, heptylsulfonyl, octylsulfonyl, 2-ethylhexylsulfonyl and positional isomers thereof.
- Ci-Cio-Alkylsulfonyl is additionally, for example, nonylsulfonyl, decylsulfonyl and positional isomers thereof.
- Ci-C2-haloalkylsulfonyl is a Ci-C2-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
- Ci-C3-haloalkylsulfonyl is a C1-C3- haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
- Ci- C4-haloalkylsulfonyl is a Ci-C4-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
- Ci-C6-haloalkylsulfonyl is a Ci-C6-haloalkyl group, as defined above, attached via a sulfonyl [S(0)2] group.
- C1-C10- haloalkylsulfonyl is a Ci-Cio-haloalkyl group, as defined above, attached via a sulfonyl [S(0) 2 ] group.
- Ci-C 2 -Haloalkylsulfonyl is, for example, S(0) 2 CH 2 F, S(0) 2 CHF 2 , S(0) 2 CF 3 , S(0) 2 CH 2 CI, S(0) 2 CHCI 2 , S(0) 2 CCI 3 , chlorofluoromethylsulfonyl, dichloro- fluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2- chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2- difluoroethylsulfonyl, 2,2-d
- C1-C4- Haloalkylsulfonyl is additionally, for example, 4-fluorobutylsulfonyl, 4- chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl.
- C1-C6- Haloalkylsulfonyl is additionally, for example, 5-fluoropentylsulfonyl, 5- chloropentylsulfonyl, 5-brompentylsulfonyl, 5-iodopentylsulfonyl, undecafluoropen- tylsulfonyl, 6-fluorohexylsulfonyl, 6-chlorohexylsulfonyl, 6-bromohexylsulfonyl, 6- iodohexylsulfonyl or dodecafluorohexylsulfonyl.
- Examples are acetyl (methylcarbonyl), propionyl (ethylcarbonyl), propylcarbonyl, isopropylcarbonyl, n-butylcarbonyl and the like.
- Ci-C6-haloalkylcarbonyl a Ci-C6-haloalkylcarbonyl
- Ci-C4-haloalkylcarbonyl Ci-C4-haloalkylcarbonyl
- Examples are trifluoromethylcarbonyl, 2,2,2- trifluoroethylcarbonyl and the like.
- Examples are methoxycarbonyl), ethoxycarbonyl, propoxycarbonyl, iso- propoxycarbonyl, n-butoxycarbonyl and the like.
- Ci-C6-haloalkoxycarbonyl a Ci-C6-haloalkoxycarbonyl
- Ci-C4-haloalkoxycarbonyl Ci-C4-haloalkoxycarbonyl
- Examples are trifluoromethoxycarbonyl, 2,2,2- trifluoroethoxycarbonyl and the like.
- Ci-C6-alkylamino is a group -N(H)Ci-C6-alkyl. Examples are methylamino, ethylamino, propylamino, isopropylamino, butylamino and the like.
- di-(Ci-C6-alkyl)amino is a group -N(Ci-C6-alkyl)2. Examples are dimethyla- mino, diethylamino, ethylmethylamino, dipropylamino, diisopropylamino, methylpropyl- amino, methylisopropylamino, ethylpropylamino, ethylisopropylamino, dibutylamino and the like.
- the term "3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or het- eroatom groups selected from N, O, S, NO, SO and SO2, as ring members” denotes a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximum unsaturated heteromonocyclic ring or a 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members.
- Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maximally unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Maximally unsaturated 5- or 6-membered heterocyclic rings are aromatic.
- the heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
- Unsaturated rings contain at least one C-C and/or C-N and/or N-N double bond(s). Maximum unsaturated rings contain as many conjugated C-C and/or C-N and/or N-N double bonds as allowed by the ring size. Maximum unsaturated 5- or 6-membered heterocyclic rings are aromatic. 7- and 8-membered rings cannot be aromatic. They are homoaromatic (7-membered ring, 3 double bonds) or have 4 double bonds (8-membered ring).
- the heterocyclic ring may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.
- Examples of a 3-, 4-, 5-, 6- or 7-membered saturated heterocyclic ring include: Oxira- nyl, thiiranyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, tetrahydrofuran-2-yl, tetrahydrofu- ran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1 -yl, pyrrolidin-2-yl, pyrrol- idin-3-yl, pyrazolidin-1 -yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazoli- din-1 -yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl,
- Examples of a 3-, 4-, 5-, 6- or 7-membered partially unsaturated heterocyclic ring include: 2,3-d ihyd rofur-2-yl , 2,3-dihydrofur-3-yl, 2,4-d ihyd rofur-2-yl , 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl,
- Examples for a 3-, 4-, 5-, 6- or 7-membered maximally unsaturated (including aromatic) heterocyclic ring are 5- or 6-membered heteroaromatic rings, such as 2-furyl, 3-furyl, 2- thienyl, 3-thienyl, 1 -pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl,
- Examples for a 8-, 9- or 10-membered saturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:
- Examples for a 8-, 9- or 10-membered partially unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:
- Examples for a 8-, 9- or 10-membered maximally unsaturated heterobicyclic ring containing 1 , 2 or 3 (or 4) heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members are:
- # denotes the attachment point to the remainder of the molecule.
- the attachment point is not restricted to the ring on which is shown, but can be on either of the fused rings, and may be on a carbon or on a nitrogen ring atom. If the rings carry one or more substituents, these may be bound to carbon and/or to nitrogen ring atoms (if the latter are not part of a double bond).
- Examples are, in addition to the saturated heteromonocy-rod rings mentioned above, carbocyclic rings, such as cyclopropyl, cyclopropanonyl, cyclobutyl, cyclobutanonyl, cyclopentyl, cyclopentanonyl, cyclohexyl, cyclohexanonyl, cyclohexadienonyl, cycloheptyl, cycloheptanonyl, cyclooctyl, cyclooctanonyl, furan-2- onyl, pyrrolidine-2-onyl, pyrrolidine-2,5-dionyl, piperidine-2-only, piperidine-2,6-dionyl and the like.
- carbocyclic rings such as cyclopropyl, cyclopropanonyl, cyclobutyl, cyclobutanonyl, cyclopentyl, cyclopentanonyl
- A is A 1 .
- R 9 is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl-, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6- haloalkynyl, and more preferably from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl and C3-C8-cycloalkyl-Ci-C4-alkyk
- R 10a and R 10b are selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs- cycloalkyl, C3-Cs-halocycloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl,
- R 10a and R 10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl
- R 10a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl
- R 14a , R 14b and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
- R 14a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl
- R 14b is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C3-C6-cycloalkyl-Ci-C4-alkyl-, Ci-C6-alkyl substituted with a CN group, Ci-C6-alkoxyl, Ci-C6-haloalkoxy, phenyl which is optionally substituted with 1 , 2, 3 or 4, substituents each independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkyl
- R 10a and R 10b are selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl,
- R 10a and R 10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocy- die ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N , O, S, NO, SO and SO2, as ring members, where the heterocyclic ring optionally carries one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-al
- R 10a is selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl
- R 14a , R 14b and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
- R 14a is preferably selected from hydrogen, Ci-C6-alkyl and Ci-C6-haloalkyl; and R 14b is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkenyl, Ci-C6-haloalkenyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-Ci-C4- alkyl-, Ci-C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , which are each independently preferably selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-
- k 0, 1 , 2 or 3
- n 0, 1 or 2
- n 0, 1 or 2;
- R 14a is selected from hydrogen and methyl
- R 14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkyl-methyl-, Ci- C6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1 , 2, 3 or 4, preferably 1 , 2 or 3, in particular 1 , substituents R 16 selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl,
- each R 16 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, C1-C4- alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
- each R 16 is independently selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
- R 14a is selected from hydrogen and methyl, and is specifically hydrogen
- R 14b is selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and C3-C6-cycloalkyl- methyl-.
- R 10a and R 10b are preferably selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C4-alkylcarbonyl, Ci-C4-haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-haloalkylaminocarbonyl, C3-C6-cycloalkylaminocarbonyl and C3-C6- halocycloalkylaminocarbonyl,
- heterocyclic ring which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particu- lar 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4- alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio.
- R 10a and R 10b are in this case selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci- C4-alkylaminocarbonyl and Ci-C4-haloalkylaminocarbonyl.
- A is A 2 .
- W is preferably O.
- Y is preferably N(R 5 )R 6 ; wherein R 5 and R 6 have one of the above general meanings, or, in particular, one of the below preferred meanings.
- R 5 and R 6 have one of the above general meanings, or, in particular, one of the below preferred meanings.
- in A 2 Y is hydrogen.
- R 9 has one of the above general meanings, or, in particular, is selected from hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl and Ci-C6-alkyl substituted by one radical R 13 , where R 13 has one of the above general meanings, or, in particular, one of the below preferred meanings.
- W is O and Y is N(R 5 )R 6 ; wherein R 5 and R 6 have one of the above general meanings, or, in particular, one of the below preferred meanings.
- W is O and Y H.
- W is O and Y is -OR 9 , where R 9 has one of the above general meanings, or, in particular, is selected from hydrogen, C1-C6- alkyl, Ci-C6-haloalkyl and Ci-C6-alkyl substituted by one radical R 13 , where R 13 has one of the above general meanings, or, in particular, one of the below preferred meanings.
- R 5 is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Cs-Cs-cycloalkyl and C3-C8- halocycloalkyl, where the aforementioned aliphatic and cycloaliphatic radicals may be substituted by 1 , 2 or 3, preferably 1 , radicals R 8 ; and
- R 6 is preferably selected from hydrogen, Ci-Cio-alkyl, Cs-Cs-cycloalkyl, C2-C10- alkenyl, C2-Cio-alkynyl, wherein the four last-mentioned aliphatic and cycloali- phatic radicals may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 8 ,
- phenyl which may be substituted with 1 , 2, 3, 4, or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 1 1 , and
- C S as ring members, wherein the heterocyclic ring may be substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents independently selected from the group consisting of halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C6- alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, wherein the aliphatic or cycloaliphatic moieties in the twelve last- mentioned radicals may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 8 , and phen
- R 8 , R 9 , R 10a , R 10b and R 11 have one of the above general meanings, or, in particular, one of the below preferred meanings.
- N(R 5 )R 6 as a radical Y More preferably, in N(R 5 )R 6 as a radical Y,
- R 5 is selected from hydrogen, Ci-C6-alkyl, C2-C3-alkynyl and -Chb-CN;
- R 6 is selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C10- haloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, where the four last-mentioned aliphatic and cycloaliphatic radicals may carry 1 , 2 or 3 radicals
- R 8 d-Ce-alkoxy, Ci-C 6 -haloalkoxy, N(R 10a )R 10b , phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R 11 , and a 3-,
- R 5 and R 6 together with the nitrogen atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated heterocyclic ring, where the ring may further contain
- R 5 and R 6 together with the nitrogen atom to which they are bound, form a group where R 9 is selected from Ci-C6-alkyl and Ci-C6-haloalkyl. Even more preferably, in N(R 5 )R 6 as a radical Y,
- R 5 is selected from hydrogen, Ci-C6-alkyl, C2-C3-alkynyl and CH2-CN;
- R 6 is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which carries one radical R 8 , C2-C6-alkenyl, C2-Cio-haloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN and pyridyl;
- Ci-Ce-alkoxy Ci-C 6 -haloalkoxy, N(R 0a )R 0b ,
- phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R 11 , and a 3-, 4- , 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups in- dependently selected from N , O, S, NO, SO and SO2, as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R 1 1 ; wherein R 8 and R 1 1 are as defined in claim 1 ;
- R 5 and R 6 together with the nitrogen atom to which they are bound, form a group where R 9 is selected from Ci-C6-alkyl and Ci-C6-haloalkyl.
- N(R 5 )R 6 as a radical Y is particularly preferably, in N(R 5 )R 6 as a radical Y,
- R 5 selected from hydrogen, Ci-C6-alkyl, C2-C3-alkynyl and CH2-CN ;
- R 6 is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which carries one radical R 8 , C2-C6-alkenyl, C2-Cio-haloalkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN and pyridyl;
- R 10a is selected from hydrogen and Ci-C6-alkyl and R 10b is selected from a 5- or 6-membered het- eroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N , O and S as ring members, where the heteroaromatic ring may be substituted with one or more substituents R 16 ;
- phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R 1 1 , and a 3-, 4- , 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N , O, S, NO, SO and SO2, as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R 1 1 ; wherein
- R 10a is selected from the group consisting of hydrogen and Ci-C6-alkyl
- R 10b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C4- alkynyl, CH 2 -CN, Ci-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halocycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy, and
- each R 16 as a substituent on phenyl or the heterocyclic rings is independently selected from the group consisting of halogen, cyano, ni- tro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci- C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
- R 5 and R 6 together with the nitrogen atom to which they are bound, form a group where R 9 is selected from Ci-C6-alkyl and Ci-C6-haloalkyl.
- N(R 5 )R 6 as a radical Y,
- R 5 is selected from hydrogen, Ci-C6-alkyl, C2-C3-alkynyl, CH2-CN and Ci-C6-alkoxy- methyl-;
- R 8 and R 11 have one of the above general meanings, or, in particular, one of the below preferred meanings;
- the 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring R 6 containing 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members is selected from rings D-1 to D-173 listed below in context with A 4 .
- the ring may be sub- stituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 11 .
- N(R 5 )R 6 as a radical Y,
- R 5 is selected from hydrogen, Ci-C6-alkyl, C2-C3-alkynyl, CH2-CN and Ci-C6-alkoxy- methyl-;
- heteromonocyclic ring may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 11 ;
- R 8 and R 11 have one of the above general meanings, or, in particular, one of the below preferred meanings;
- N(R 5 )R 6 as a radical Y,
- R 5 is selected from hydrogen and Ci-C6-alkyl
- R 6 is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which carries one radical R 8 , C3-C6-cycloalkyl which may be substituted by 1 or 2 substituents selected from F, CN, methyl and oxo,
- R 8 and R 11 have one of the above general meanings, or, in particular, one of the below preferred meanings;
- R 5 and R 6 together with the nitrogen atom to which they are bound, form a 5- or
- the 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members is selected from rings D-1 to D-173 listed below in context with A 4 , and more preferably from rings F-1 to F-51 listed below.
- the ring may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 11 .
- N(R 5 )R 6 as a radical Y,
- R 5 is selected from hydrogen and methyl, preferably hydrogen
- R 6 is selected from Ci-C4-alkyl which carries one radical R 8 , preferably methyl which carries one radical R 8 , Ci-C4-haloalkyl, and a 4-, 5- or 6-membered saturated heteromonocyclic ring containing 1 het- eroatom or heteroatom group selected from S, SO and SO2, as ring member, where the heteromonocyclic ring may be substituted with one or more substitu- ents R 11 ;
- R 8 and R 11 have one of the above general meanings, or, in particular, one of the below preferred meanings;
- R 5 and R 6 together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated heterocyclic ring (i.e. R 5 and R 6 form together -(Chb or - (CH2)5-), wherein the heterocyclic ring may be substituted with 1 , 2 or 3 substitu- ents independently selected from the group consisting of halogen, cyano, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.
- the ring may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substitu- ents R 11 .
- R 9 , R 10a , R 10b and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
- N(R 5 )R 6 as a radical Y More preferably, in N(R 5 )R 6 as a radical Y,
- R 9 , R 10a , R 10b and R 16 have one of the above general meanings, or, in particular, one of the below preferred meanings.
- R 10a and R 10b are preferably selected, independently of each other, from hydrogen, Ci- C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-haloalkylaminocarbonyl, C3-
- heterocyclic ring which additionally may contain 1 or 2 further heteroatoms or heteroatom groups select- ed from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN, C1-C4- alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio.
- R 10a and R 10b are in this case selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci- C4-alkylaminocarbonyl and Ci-C4-haloalkylaminocarbonyl. Specifically, they are selected, independently of each other, from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl and C3- C6-cycloalkyl. Very specifically, one of R 10a and R 10b is hydrogen and the other is C1-C4- alkyl, Ci-C4-haloalkyl or C3-C6-cycloalkyl.
- R 5 is hydrogen
- R 6 is selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C4-alkyl which carries one radical R 8 , Cs-Ce-cycloalkyl,
- phenyl which may be substituted with 1 , 2, 3, 4, or 5 substituents R 11 , and a 4-, 5- or 6-membered saturated heteromonocyclic ring containing 1 heteroatom or heteroatom group selected from N, O, S, SO and SO2, as ring member or a 5- or 6- membered heteromonocyclic aromatic ring containing 1 , 2 or 3 heteroatoms selected from O, N and S as ring members, where the heteromonocyclic ring may be substituted with one or more substituents R 11 , where the heteromonocyclic ring is preferably selected from rings of formulae F-1 to F-51 :
- k 0, 1 , 2 or 3,
- n 0, 1 or 2
- R 10a is selected from the group consisting of hydrogen, Ci-C6-alkyl, C2-C3- alkynyl, -CH2-CIM and Ci-C6-alkoxy-methyl;
- R 10b is selected from the group consisting of hydrogen, Ci-C6-alkyl, C1-C6- haloalkyl, C3-C6-cycloalkyl, C3-C6-cyclohaloalkyl, phenyl which is op- tionally substituted with 1 , 2, 3, 4 or 5 substituents selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; and a heterocyclic ring selected from rings
- each R 16 as a substituent on phenyl or a heterocyclic ring E-1 to E-51 is independently selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci- C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6- halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
- F-44 preference is given to F-44, F-48 and F-49.
- W is O and Y is N(R 5 )R 6 , wherein
- R 5 is selected from hydrogen and methyl, preferably hydrogen
- R 6 is selected from Ci-C4-alkyl which carries one radical R 8 , preferably methyl which carries one radical R 8 ; Ci-C4-haloalkyl, and a 4-, 5- or 6-membered saturated heteromonocyclic ring containing 1 heteroatom or heteroatom group selected from S, SO and SO2, as ring member, where the heteromonocyclic ring may be substituted with one or more substituents R 11 ;
- R 10a and R 10b are selected, independently of each other, from hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 - alkynyl, C2-C 4 -haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci- C 4 -alkylcarbonyl, Ci-C 4 -haloalkylcarbonyl, Ci-C 4 -alkylaminocarbonyl, Ci-C 4 -haloalkylaminocarbonyl, C3-C6-cycloalkylaminocarbonyl and C3-C6-halocycloalkylaminocarbonyl, and preferably from hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl and C3-C6-cyclo
- each R 11 is independently selected from halogen, cyano, nitro, Ci-C 4 - alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4- alkenyl, C2-C 4 -haloalkenyl, C2-C 4 -alkynyl and C2-C 4 -haloalkynyl; and each R 16 is independently selected from halogen, cyano, nitro, C1-C4- alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -haloalkylthio, C3
- R 5 and R 6 together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN, C1-C4- alkyl, Ci-C 4 -haloalkyl, C2-C 4 -alkenyl, C2-C 4 -haloalkenyl, C2-C 4 -alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C 4 -alkoxy, C1-C4- haloalkoxy, Ci-C 4 -alkylthio and Ci-C 4 -haloalkylthio, and form hal
- R 5 and R 6 form together -(CH2) 4 - or - (CH2)5-), wherein the heterocyclic ring may be substituted with 1 , 2 or 3 substituents independently selected from the group consisting of halogen, cyano, C1-C6- alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and Ci-C6-haloalkoxy.
- the 5- or 6-membered heteroaromatic ring comprising 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members is selected from rings E-1 to E-42 as defined above.
- the ring may be substituted with one or more, preferably 1 , 2 or 3, in par- ticular 1 , substituents R 16 selected from the group consisting of halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl.
- A is A 3
- R 7a and R 7b in the group A 3 are independently of each other selected from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl, and more preferably one of R 7a and R 7b is hydrogen and the other is hydrogen or methyl. Specifically, both are hydrogen.
- R 5 is preferably selected from hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 8 ; and
- R 6 is preferably selected from hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 8 ,
- heteromonocyclic or heterobicyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 11 ;
- R 5 is selected from hydrogen, Ci-C4-alkyl, which may be partially or fully halogenat- ed and/or may be substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 8 selected from cyano and Ci-C6-alkoxy; and C2-C4-alkynyl; and
- R 8 , R 9 , R 10a , R 10b and R 11 have one of the above general meanings, or, in particular, one of the below preferred meanings.
- the group A 3 is selected from hydrogen, Ci-C4-alkyl, C2-C3-alkynyl, CH2-CN and Ci-C6-alkoxy- methyl-, preferably from hydrogen and Ci-C4-alkyl; and
- R 8 has one of the above general meanings, or, in particular, one of the below preferred meanings.
- phenyl optionally substituted with 1 , 2, 3, 4 or 5, preferably 1 , 2 or 3, in particular 1 , substituents R 16 , and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or heteroa- tom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 16 ,
- R 9 , R 10a , R 10b , R 13 and R 16 have one of the above general meanings, or, in par- ticular, one of the below preferred meanings.
- R 10a and R 10b together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C2- C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3- C6-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and C1-C4- haloalkylthio.
- R 10a and R 10b in R 8 in the radicals R 5 and R 6 of the group A 3 are, inde- pendently of each other, selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkyl substituted by one radical R 13 , C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and a 3- or 4-membered saturated heterocyclic ring comprising 1 heteroatom or heteroatom group selected from N, O, S, NO, SO and SO2, as ring member, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and C1-C4- haloalkoxy; and are specifically, independently of each other, selected from hydrogen, Ci-C4-alkyl,
- R 13 in R 8 in the radicals R 5 and R 6 of the group A 3 is preferably selected from CN, Ci- C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci- C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl and Ci-C6-haloalkylsulfonyl.
- R 16 in R 8 in the radicals R 5 and R 6 of the group A 3 is preferably selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
- R 10a and R 10b are selected from hydrogen, Ci-C4-alkyl,
- Ci-C4-haloalkyl and C3-C6-cycloalkyl are Ci-C4-haloalkyl and C3-C6-cycloalkyl
- R 13 is selected from CN, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6- haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, Ci-C6-alkylsulfonyl, Ci- C6-haloalkylsulfonyl and a heterocyclic ring selected from rings of formulae E-1 to
- E-51 as defined above and preferably from Ci-C6-alkylthio, Ci-C6-haloalkylthio,
- Ci-C6-alkylsulfonyl and Ci-C6-haloalkylsulfonyl are Ci-C6-alkylsulfonyl and Ci-C6-haloalkylsulfonyl.
- each R 16 as a substituent on heterocyclic rings of formulae E-1 to E-51 is independently selected from the group consisting of halogen, cyano, nitro, C1-C4- alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, Ci-C 4 -alkylthio, C1-C4- haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
- A is A 4 .
- a 4 is preferably selected from a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic ring containing 1 , 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heteromonocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 11 , where R 11 has one of the above general meanings, or, in particular, one of the below preferred meanings.
- a 4 is selected from a 3-, 4-, 5-, 6- or 7-membered saturated heteromonocyclic ring containing 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, a 5-, 6- or 7-membered partially unsaturated heteromonocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, and a 5- or 6-membered aromatic heteromonocyclic ring containing 1 , 2, 3 or 4 heteroatoms selected from N, O and S as ring members, where the heteromonocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents R 11 , where R 11 has one of the above general meanings, or, in particular, one of the below preferred meanings.
- a 4 is even more preferably selected from rings of formulae D-1 to D-173
- D-59 is in particular selected from D-59, D-65 and D-66 and is specifcally D-59.
- each R 1 1 is independently selected from the group consisting of halogen, cyano, ni- tro, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl; or
- radicals A 1 , A 2 , A 3 and A 4 preference is given to A 2 .
- B 1 , B 2 and B 3 are CR 2 .
- B 1 and B 3 are CR 2 , where R 2 is not hydrogen, and B 2 is CR 2 , where R 2 has one of the meanings given above.
- R 2 is selected from hydrogen, halogen, cyano, azido, nitro, -SCN , SF 5 , Ci- C6-alkyl, Cs-Cs-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, wherein the four last mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 8 , -OR 9 , -S(0) n R 9 and -N R 10a R 10b ,
- R 8 , R 9 , R 10a and R 10b have one of the above general meanings, or, in particular, one of the below preferred meanings. More preferably, R 2 is selected from hydrogen, halogen and Ci-C2-haloalkyl, even more preferably from hydrogen, F, CI, Br and CF3, even more preferably from hydrogen, F, CI and CF3, and in particular from hydrogen and CI.
- B 2 is CH and B 1 and B 3 have one of the general or one of the preferred meanings given above for R 2 (with the proviso that they are not hydrogen) and are preferably selected from halogen and Ci-C2-haloalkyl, even more preferably from F, CI, Br and CF3, particularly preferably from hydrogen, F, CI and CF3, and are in particular CI.
- B 2 is CF or CCI and B 1 and B 3 have one of the general or one of the preferred meanings given above for R 2 (with the proviso that they are not hydrogen) and are preferably selected from halogen and Ci-C2-haloalkyl, such as F, CI and CF3, even more preferably from F and CI, and are in particular CI.
- G 1 , G 3 and G 4 are CR 4 and G 2 is N or CR 4 , where R 4 has one of the meanings given above or below; or G 2 , G 3 and G 4 are CR 4 and G 1 is N or CR 4 , where R 4 has one of the meanings given above or below.
- R 4 is selected from hydrogen, halogen, cyano, azido, nitro, Ci-C6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 8 , Cs-Cs-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 8 , C2-C6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 8 , C2-C6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more, preferably 1 , 2 or 3, in particular 1 , radicals R 8 , -OR 9 , -S(0) n R 9 , and -NR 10a R 10b .
- R 4 is selected from hydrogen, halogen, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C4-alkenyl, C2-C4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C1-C6- alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, Ci-C6-haloalkylsulfinyl, C1-C6- alkylsulfonyl, Ci-C6-haloalkylsulfonyl, and even more preferably from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl,
- G 1 , G 3 and G 4 are CH and G 2 is CR 4 , where R 4 has one of the above general or preferred meanings; or G 1 is N, G 3 and G 4 are CH and G 2 is CR 4 .
- G 1 and G 4 are CR 4 and G 2 and G 3 are CH, where R 4 has one of the meanings given above or below.
- G 1 , G 3 and G 4 are CH and G 2 is CR 4 , where R 4 is selected from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, C1-C4- haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio, preferably from hydrogen, F, CI, CN, methyl, CF3, methoxy and methylthio, and specifically from hydrogen, F, CI, CN, methyl methoxy and methylthio.
- G 1 is N
- G 2 is CR 4 and G 3 and G 4 are CH
- R 4 is selected from hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and Ci-C4-haloalkylthio, preferably from hydrogen, F, CI, CN, methyl, CF3, methoxy and methylthio, and specifically from hydro- gen and methyl.
- R 1 is Ci-C4-haloalkyl, specifically Ci- C2-haloalkyl and more specifically halomethyl, in particular fluoromethyl, such as fluo- romethyl, difluoromethyl and trifluoromethyl, and is very specifically trifluoromethyl.
- R 3a and R 3b are selected, independently of each other, from hydrogen, halogen, hydroxyl, Ci-C3-alkyl, Ci-C3-alkenyl, Ci-C3-alkynyl, Ci-C3-haloalkyl, Ci-C3-alkoxy, Ci-C3-alkylthio and Ci-C3-alkylsulfonyl, more preferably from hydrogen and halogen, in particular from hydrogen and fluorine and are specifically hydrogen.
- R 8 , R 9 , R 10a , R 10b , R 11 , R 12 , R 13 , R 14 , R 14a , R 14b , R 15 and R 16 have following preferred meanings:
- R 8 is a substituent on a cycloalkyl group, it is even more preferably selected from the group consisting of halogen, Ci-C 4 -alkyl, Ci-C3-haloalkyl, Ci-C 4 -alkoxy and Ci-C3-haloalkoxy.
- R 8 as a substituent on a cycloalkyl group is selected from halogen, Ci-C 4 -alkyl and Ci-C3-haloalkyl.
- R 8 is preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci- C6-alkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- Ce-alkynyl, C 2 -C 6 -haloalkynyl, -OR 9 , -SR 9 , -N(R 10a )R 10b , phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or
- R 8 is more preferably selected from the group consisting of Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs- Cs-halocycloalkyl, d-Ce-alkoxy, Ci-C 6 -haloalkoxy, -N(R 10a )R 10b , phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R 16 , and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R 16 ; where R 10a , R 10b and
- each R 9 is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Cs-cycloalkyl- Ci-C4-alkyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R 16 ; and a 3-, 4- , 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1 , 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may be substituted by one or more, e.g.
- each R 9 is independently selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl which may be substituted by 1 , 2, 3, 4 or 5 radicals R 16 ; and a 5- or 6-membered heteroaromatic ring containing 1 , 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring may be substituted by one or more radicals R 16 ; where R 16 has one of the meanings given above or in particular one of the preferred meanings given below.
- R 10a and R 10b are, independently of each other, preferably selected from hydrogen, Ci- C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkylcarbonyl, C1-C4- haloalkylcarbonyl, Ci-C4-alkylaminocarbonyl, Ci-C4-haloalkylaminocarbonyl, C3-C6- cycloalkylaminocarbonyl, C3-C6-halocycloalkylaminocarbonyl, and a 3-, 4-, 5-, 6- or 7- membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 , 2 or 3 heteroatoms or hetero
- R 10a and R 10b together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and S0 2 , as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C 2 - C4-alkenyl, C 2 -C4-haloalkenyl, C 2 -C4-alkynyl, C 2 -C4-haloalkynyl, C3-C6-cycloalkyl, C3- C6-halocycloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio and C1-C4- haloalkyl
- R 10a and R 10b are, independently of each other, selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and a 3- or 4-membered saturated heterocyclic ring comprising 1 heteroatom or heteroatom group selected from N, O, S, NO, SO and S0 2 , as ring member, where the heterocyclic ring is optionally substituted with one or more, preferably 1 , 2 or 3, in particular 1 , substituents selected from halogen, CN , Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci- C4-haloalkoxy; and are specifically, independently of each other, selected from hydrogen, Ci-C4-alkyl and Ci-C4-haloalkyl.
- Each R 11 and each R 16 are independently of each occurrence and independently of each other preferably selected from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, C1-C4- haloalkylsulfinyl, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl, and more preferably from halogen, CN, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
- Each R 12 is preferably selected from Ci-C4-alkyl and is in particular methyl.
- R 13 is a substituent on an alkyl, alkenyl or alkynyl group, it is preferably selected from the group consisting of cyano, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, -OH, - SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, C1-C4- alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl and phenyl which may be substituted by 1 , 2 or 3 radicals selected from halogen, C1-C4- alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
- R 13 is a substituent on a cycloalkyl group, it is preferably selected from the group consisting of cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl, -OH, -SH, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, C1-C4- haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-haloalkylsulfinyl, Ci-C4-alkylsulfonyl, C1-C4- haloalkylsulfonyl and phenyl which may be substituted by 1 , 2 or 3 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and
- R 13 is a substituent on a cycloalkyl group, it is even more preferably selected from the group consisting of halogen, Ci-C4-alkyl, Ci-C3-haloalkyl, Ci-C4-alkoxy and Ci-C3-haloalkoxy.
- R 13 as a substituent on a cycloalkyl group is selected from halogen, Ci-C4-alkyl and Ci-C3-haloalkyl.
- R 8 is preferably selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs- Cs-cycloalkyl, C3-Cs-halocycloalkyl, -OH, -SH, Ci-C6-alkoxy, Ci-C6-haloalkoxy and phenyl which may be substituted by 1 , 2 or 3 radicals selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy.
- R 14 , R 14a and R 14b are, independently of each other, preferably selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and benzyl, where the phenyl ring in benzyl is optionally substituted 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy;
- R 14a and R 14b together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C1-C4- alkoxy and Ci-C4-haloalkoxy.
- R 14 , R 14a and R 14b are, independently of each other, selected from hydrogen, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and benzyl, where the phenyl ring in benzyl is optionally substituted 1 , 2 or 3, in particular 1 , substituents selected from halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci- C4-haloalkoxy; or, R 14a and R 14b , together with the nitrogen atom to which they are bound, form a 5- or 6-membered saturated, partially unsaturated or aromatic heterocyclic ring, which additionally may contain 1 or 2 further heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO2, as ring members, where the heterocyclic ring may carry 1 or 2, in particular 1 , substituents
- Each R 15 is preferably selected from hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may be unsubsti- tuted and/or carry 1 , 2 or 3 substituents selected from Ci-C6-alkyl, Ci-C6-haloalkyl, Ci- C6-alkoxy and Ci-C6-haloalkoxy.
- compound I is a compound of formula IA
- R 2 and R 4 have one of the above-given general or, in particular, one of the above-given preferred meanings
- R 2a and R 2c independently of each other, have one of the general or, in particular, one of the preferred meanings given above for R 2 , with the proviso that they are not hydrogen, and are specifically CI or CF3 and are very specifically CI.
- Examples of preferred compounds are compounds of the following formulae la.1 to la.31 , where the variables have one of the general or preferred meanings given above.
- Examples of preferred compounds are the individual compounds compiled in the tables 1 to 2082 below, Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question. 70
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Abstract
Description
Claims
Priority Applications (13)
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MX2014006973A MX2014006973A (en) | 2011-12-23 | 2012-12-21 | Isothiazoline compounds for combating invertebrate pests. |
EP12810287.8A EP2794601B1 (en) | 2011-12-23 | 2012-12-21 | Isothiazoline compounds for combating invertebrate pests |
US14/366,161 US9732051B2 (en) | 2011-12-23 | 2012-12-21 | Isothiazoline compounds for combating invertebrate pests |
AU2012356947A AU2012356947A1 (en) | 2011-12-23 | 2012-12-21 | Isothiazoline compounds for combating invertebrate pests |
CA2858766A CA2858766A1 (en) | 2011-12-23 | 2012-12-21 | Isothiazoline compounds for combating invertebrate pests |
BR112014015553-4A BR112014015553B1 (en) | 2011-12-23 | 2012-12-21 | ISOTIAZOLINE COMPOUNDS, COMPOUND PREPARATION METHOD, AGRICULTURAL OR VETERINARY COMPOSITION, USES OF A COMPOUND AND METHOD TO PROTECT PLANTS |
JP2014548048A JP6415983B2 (en) | 2011-12-23 | 2012-12-21 | Isothiazoline compounds for controlling invertebrate pests |
IN4376CHN2014 IN2014CN04376A (en) | 2011-12-23 | 2012-12-21 | |
ES12810287T ES2727479T3 (en) | 2011-12-23 | 2012-12-21 | Isothiazoline compounds to fight invertebrate pests |
KR1020147020594A KR20140115329A (en) | 2011-12-23 | 2012-12-21 | Isothiazoline compounds for combating invertebrate pests |
CN201280070554.8A CN104169278B (en) | 2011-12-23 | 2012-12-21 | The iso thiazolinium compound of controlling invertebrate pests |
IL233312A IL233312A0 (en) | 2011-12-23 | 2014-06-23 | Isothiazoline compounds for combating invertebrate pests |
ZA2014/05336A ZA201405336B (en) | 2011-12-23 | 2014-07-21 | Isothiazoline compounds for combating invertebrate pests |
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WO2014206911A1 (en) * | 2013-06-24 | 2014-12-31 | Basf Se | Isothiazoline compounds for combating invertebrate pests |
WO2015104422A1 (en) | 2014-01-13 | 2015-07-16 | Basf Se | Dihydrothiophene compounds for controlling invertebrate pests |
WO2015114157A1 (en) * | 2014-02-03 | 2015-08-06 | Basf Se | Cyclopentene and cyclopentadiene compounds for controlling invertebrate pests |
US20160143283A1 (en) * | 2013-06-21 | 2016-05-26 | Basf Se | Suspension concentrate composition comprising isothiazoline insecticide and activated charcoal |
EP2755969B1 (en) * | 2011-09-13 | 2017-01-18 | Syngenta Participations AG | Isothiazoline derivatives as insecticidal compounds |
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MX2014006973A (en) | 2014-08-01 |
CL2014001688A1 (en) | 2014-11-07 |
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CO6980665A2 (en) | 2014-06-27 |
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