CA2916824C - Naphthyl- or isoquinolinyl-substituted isothiazoline compounds - Google Patents
Naphthyl- or isoquinolinyl-substituted isothiazoline compounds Download PDFInfo
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- CA2916824C CA2916824C CA2916824A CA2916824A CA2916824C CA 2916824 C CA2916824 C CA 2916824C CA 2916824 A CA2916824 A CA 2916824A CA 2916824 A CA2916824 A CA 2916824A CA 2916824 C CA2916824 C CA 2916824C
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- -1 isoquinolinyl-substituted isothiazoline compounds Chemical class 0.000 title claims abstract description 624
- 150000001875 compounds Chemical class 0.000 claims abstract description 788
- 239000000203 mixture Substances 0.000 claims abstract description 59
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 41
- 239000000463 material Substances 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 281
- 239000001257 hydrogen Substances 0.000 claims description 280
- 150000002431 hydrogen Chemical group 0.000 claims description 216
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 69
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical group 0.000 claims description 66
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 57
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 41
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 22
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 14
- 241001465754 Metazoa Species 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 206010061217 Infestation Diseases 0.000 claims description 9
- 150000001204 N-oxides Chemical class 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000002689 soil Substances 0.000 claims description 8
- 238000009395 breeding Methods 0.000 claims description 7
- 230000001488 breeding effect Effects 0.000 claims description 7
- 150000002466 imines Chemical class 0.000 claims description 7
- 230000002633 protecting effect Effects 0.000 claims description 6
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 229910052705 radium Inorganic materials 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 241000244206 Nematoda Species 0.000 abstract description 22
- 241000238421 Arthropoda Species 0.000 abstract description 5
- 235000013350 formula milk Nutrition 0.000 description 357
- 150000003254 radicals Chemical class 0.000 description 113
- 229910052717 sulfur Inorganic materials 0.000 description 93
- 125000005842 heteroatom Chemical group 0.000 description 90
- 125000001424 substituent group Chemical group 0.000 description 87
- 241000196324 Embryophyta Species 0.000 description 74
- 125000000623 heterocyclic group Chemical group 0.000 description 74
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 46
- 229920006395 saturated elastomer Polymers 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 44
- 229940000425 combination drug Drugs 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 239000003112 inhibitor Substances 0.000 description 36
- 239000000460 chlorine Substances 0.000 description 35
- 239000002904 solvent Substances 0.000 description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 28
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 150000001412 amines Chemical class 0.000 description 25
- 125000001931 aliphatic group Chemical group 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 23
- 239000003053 toxin Substances 0.000 description 23
- 231100000765 toxin Toxicity 0.000 description 22
- 108700012359 toxins Proteins 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 108090000623 proteins and genes Proteins 0.000 description 21
- 239000002585 base Substances 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-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 18
- 229910052801 chlorine Inorganic materials 0.000 description 17
- 239000013543 active substance Substances 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 235000018102 proteins Nutrition 0.000 description 16
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 15
- 241000238631 Hexapoda Species 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 229930195729 fatty acid Natural products 0.000 description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 description 15
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 14
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 125000003342 alkenyl group Chemical group 0.000 description 14
- 229910052794 bromium Inorganic materials 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 13
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 12
- 230000001276 controlling effect Effects 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 11
- 238000005576 amination reaction Methods 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000004009 herbicide Substances 0.000 description 11
- 230000000749 insecticidal effect Effects 0.000 description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
- 229940126214 compound 3 Drugs 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 125000004430 oxygen atom Chemical group O* 0.000 description 10
- 150000003871 sulfonates Chemical class 0.000 description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 10
- 125000004434 sulfur atom Chemical group 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 150000003573 thiols Chemical class 0.000 description 10
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
- 241000482268 Zea mays subsp. mays Species 0.000 description 9
- 238000007792 addition Methods 0.000 description 9
- 235000005822 corn Nutrition 0.000 description 9
- 238000010790 dilution Methods 0.000 description 9
- 239000012895 dilution Substances 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 230000004224 protection Effects 0.000 description 9
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 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
- 239000003960 organic solvent Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 241000894007 species Species 0.000 description 8
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 description 7
- 241000239223 Arachnida Species 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 241000258937 Hemiptera Species 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 7
- 229960004132 diethyl ether Drugs 0.000 description 7
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 229940052303 ethers for general anesthesia Drugs 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 229930195733 hydrocarbon Natural products 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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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
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- 229960005349 sulfur Drugs 0.000 description 7
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 108020004511 Recombinant DNA Proteins 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 235000002595 Solanum tuberosum Nutrition 0.000 description 6
- 244000061456 Solanum tuberosum Species 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229940074995 bromine Drugs 0.000 description 6
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- 239000003086 colorant Substances 0.000 description 6
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- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 6
- 238000005580 one pot reaction Methods 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
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- 239000000047 product Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 description 5
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 5
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical class C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
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- 239000002671 adjuvant Substances 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 238000007112 amidation reaction Methods 0.000 description 5
- DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 5
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
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- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 229940093956 potassium carbonate Drugs 0.000 description 5
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- 125000004076 pyridyl group Chemical group 0.000 description 5
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- 239000000126 substance Substances 0.000 description 5
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- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 4
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 4
- 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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- 241000257162 Lucilia <blowfly> Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- 241001161749 Stenchaetothrips biformis Species 0.000 description 4
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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- 239000012190 activator Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
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- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 4
- 230000009435 amidation Effects 0.000 description 4
- UINZSQJVKLWNOU-UHFFFAOYSA-N amino diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(ON)OC1=CC=CC=C1 UINZSQJVKLWNOU-UHFFFAOYSA-N 0.000 description 4
- 239000003849 aromatic solvent Substances 0.000 description 4
- 229940076134 benzene Drugs 0.000 description 4
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000002837 carbocyclic group Chemical group 0.000 description 4
- 150000001728 carbonyl compounds Chemical class 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- 229940117389 dichlorobenzene Drugs 0.000 description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 4
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 4
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 4
- 235000019797 dipotassium phosphate Nutrition 0.000 description 4
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- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- 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<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361838354P | 2013-06-24 | 2013-06-24 | |
| US61/838,354 | 2013-06-24 | ||
| PCT/EP2014/063101 WO2014206907A1 (en) | 2013-06-24 | 2014-06-23 | Naphthyl- or isoquinolinyl-substituted isothiazoline compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2916824A1 CA2916824A1 (en) | 2014-12-31 |
| CA2916824C true CA2916824C (en) | 2021-05-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2916824A Expired - Fee Related CA2916824C (en) | 2013-06-24 | 2014-06-23 | Naphthyl- or isoquinolinyl-substituted isothiazoline compounds |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10327446B2 (enExample) |
| EP (1) | EP3013807B1 (enExample) |
| JP (1) | JP6407987B2 (enExample) |
| CN (1) | CN105473564A (enExample) |
| BR (1) | BR112015032344A2 (enExample) |
| CA (1) | CA2916824C (enExample) |
| ES (1) | ES2817098T3 (enExample) |
| MX (1) | MX374351B (enExample) |
| WO (1) | WO2014206907A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2016010094A (es) | 2014-02-03 | 2016-11-15 | Basf Se | Compuestos de ciclopenteno y ciclopentadieno para controlar plagas de invertebrados. |
| WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
| WO2018234488A1 (en) | 2017-06-23 | 2018-12-27 | Basf Se | Substituted cyclopropyl derivatives |
| CN111333512A (zh) * | 2020-03-09 | 2020-06-26 | 江苏君若药业有限公司 | 阿福拉纳关键中间体4-乙酰基-1-萘甲酸酯的制备 |
| CN114380762A (zh) * | 2022-01-23 | 2022-04-22 | 贵州大学 | 异恶唑啉酰肼衍生物及其制备方法和用途 |
| WO2025109114A1 (en) | 2023-11-24 | 2025-05-30 | Syngenta Crop Protection Ag | Novel carboxamide compounds |
| CN118765716B (zh) * | 2024-09-09 | 2024-12-06 | 云南省农业科学院药用植物研究所 | 一种中华腐生牛肝菌菌种培养方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007106756A (ja) * | 2005-09-14 | 2007-04-26 | Nissan Chem Ind Ltd | 置換イソキサゾリン化合物及び有害生物防除剤 |
| TWI412322B (zh) * | 2005-12-30 | 2013-10-21 | Du Pont | 控制無脊椎害蟲之異唑啉 |
| EP2181100A2 (en) * | 2007-04-10 | 2010-05-05 | Bayer CropScience AG | Insecticidal aryl isoxazoline derivatives |
| WO2008154528A2 (en) * | 2007-06-13 | 2008-12-18 | E. I. Du Pont De Nemours And Company | Isoxazoline insecticides |
| WO2009005015A1 (ja) * | 2007-06-29 | 2009-01-08 | Nissan Chemical Industries, Ltd. | 置換イソキサゾリン又はエノンオキシム化合物および有害生物防除剤 |
| WO2009035004A1 (ja) * | 2007-09-10 | 2009-03-19 | Nissan Chemical Industries, Ltd. | 置換イソキサゾリン化合物および有害生物防除剤 |
| ES2399572T3 (es) * | 2007-10-03 | 2013-04-02 | E. I. Du Pont De Nemours And Company | Compuestos de naftaleno isoxazolina para el control de plagas de invertebrados |
| JP2009286773A (ja) * | 2008-03-14 | 2009-12-10 | Bayer Cropscience Ag | 殺虫性縮環式アリール類 |
| CN102325758A (zh) * | 2008-12-23 | 2012-01-18 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的亚胺化合物 |
| ES2546417T3 (es) * | 2010-02-01 | 2015-09-23 | Basf Se | Compuestos de isoxazolina cetónica sustituidos y derivados para combatir plagas animales |
| EP2536698B1 (en) * | 2010-02-17 | 2015-06-10 | Syngenta Participations AG | Isoxazoline derivatives as insecticides |
| CN103781356A (zh) * | 2011-08-25 | 2014-05-07 | 先正达参股股份有限公司 | 作为杀虫化合物的异噁唑啉衍生物 |
| EP3190110B1 (en) * | 2011-09-13 | 2020-01-08 | Syngenta Participations AG | Isothiazoline derivatives as insecticidal compounds |
| JP2014533735A (ja) * | 2011-11-29 | 2014-12-15 | ノバルティス アーゲー | 外寄生生物を防除するためのアリール誘導体の使用 |
| BR112014015553B1 (pt) | 2011-12-23 | 2020-02-27 | Basf Se | Compostos de isotiazolina, método de preparação de compostos, composição agrícola ou veterinária, usos de um composto e método para proteger plantas |
-
2014
- 2014-06-23 MX MX2015018019A patent/MX374351B/es active IP Right Grant
- 2014-06-23 JP JP2016522420A patent/JP6407987B2/ja not_active Expired - Fee Related
- 2014-06-23 CN CN201480043335.XA patent/CN105473564A/zh active Pending
- 2014-06-23 ES ES14731658T patent/ES2817098T3/es active Active
- 2014-06-23 CA CA2916824A patent/CA2916824C/en not_active Expired - Fee Related
- 2014-06-23 WO PCT/EP2014/063101 patent/WO2014206907A1/en not_active Ceased
- 2014-06-23 US US14/757,414 patent/US10327446B2/en active Active
- 2014-06-23 EP EP14731658.2A patent/EP3013807B1/en active Active
- 2014-06-23 BR BR112015032344A patent/BR112015032344A2/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2016530226A (ja) | 2016-09-29 |
| ES2817098T3 (es) | 2021-04-06 |
| MX2015018019A (es) | 2016-07-06 |
| MX374351B (es) | 2025-03-06 |
| WO2014206907A1 (en) | 2014-12-31 |
| US10327446B2 (en) | 2019-06-25 |
| CN105473564A (zh) | 2016-04-06 |
| US20160374342A1 (en) | 2016-12-29 |
| EP3013807A1 (en) | 2016-05-04 |
| EP3013807B1 (en) | 2020-04-08 |
| JP6407987B2 (ja) | 2018-10-17 |
| CA2916824A1 (en) | 2014-12-31 |
| BR112015032344A2 (pt) | 2017-07-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20190530 |
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| MKLA | Lapsed |
Effective date: 20220623 |