CA2881995A1 - Azaindole carboxylic acid amides and azaindole thiocarboxylic acid amides for use as insecticides and acaricides - Google Patents
Azaindole carboxylic acid amides and azaindole thiocarboxylic acid amides for use as insecticides and acaricides Download PDFInfo
- Publication number
- CA2881995A1 CA2881995A1 CA2881995A CA2881995A CA2881995A1 CA 2881995 A1 CA2881995 A1 CA 2881995A1 CA 2881995 A CA2881995 A CA 2881995A CA 2881995 A CA2881995 A CA 2881995A CA 2881995 A1 CA2881995 A1 CA 2881995A1
- Authority
- CA
- Canada
- Prior art keywords
- spp
- alkyl
- cyano
- halogen
- alkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- -1 Azaindole carboxylic acid Chemical class 0.000 title claims description 217
- 230000000895 acaricidal effect Effects 0.000 title abstract description 11
- 239000002917 insecticide Substances 0.000 title abstract description 11
- 239000000642 acaricide Substances 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 315
- 238000000034 method Methods 0.000 claims abstract description 54
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims description 81
- 125000001424 substituent group Chemical group 0.000 claims description 69
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 61
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical class 0.000 claims description 60
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 51
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 49
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 36
- 241001465754 Metazoa Species 0.000 claims description 33
- 230000008569 process Effects 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 22
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 21
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 21
- 241000607479 Yersinia pestis Species 0.000 claims description 21
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 239000000575 pesticide Substances 0.000 claims description 15
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 7
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 7
- 239000004606 Fillers/Extenders Substances 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 5
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 4
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 2
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002053 thietanyl group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims 1
- 239000012868 active agrochemical ingredient Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 84
- 241000196324 Embryophyta Species 0.000 description 77
- 239000000203 mixture Substances 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 62
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 50
- 238000002360 preparation method Methods 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 239000002904 solvent Substances 0.000 description 37
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 238000009472 formulation Methods 0.000 description 32
- 238000012360 testing method Methods 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000003995 emulsifying agent Substances 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 239000003112 inhibitor Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 240000008042 Zea mays Species 0.000 description 17
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 14
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 14
- 239000012141 concentrate Substances 0.000 description 14
- 235000008504 concentrate Nutrition 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 230000002829 reductive effect Effects 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 11
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 11
- 235000013399 edible fruits Nutrition 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 235000009973 maize Nutrition 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000007921 spray Substances 0.000 description 11
- 229920000742 Cotton Polymers 0.000 description 10
- 241000219146 Gossypium Species 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 241000238631 Hexapoda Species 0.000 description 9
- 241000244206 Nematoda Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 235000010469 Glycine max Nutrition 0.000 description 8
- 244000068988 Glycine max Species 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000000969 carrier Substances 0.000 description 8
- 244000038559 crop plants Species 0.000 description 8
- RDBBFJAPMNVENH-UHFFFAOYSA-N methyl 1h-pyrazolo[4,3-b]pyridine-5-carboxylate Chemical compound COC(=O)C1=CC=C2NN=CC2=N1 RDBBFJAPMNVENH-UHFFFAOYSA-N 0.000 description 8
- 244000005700 microbiome Species 0.000 description 8
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 8
- 229920000151 polyglycol Polymers 0.000 description 8
- 239000010695 polyglycol Substances 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 description 7
- 241000238876 Acari Species 0.000 description 7
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- 239000005799 Isopyrazam Substances 0.000 description 7
- 241001608567 Phaedon cochleariae Species 0.000 description 7
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 7
- 244000046052 Phaseolus vulgaris Species 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 229940107700 pyruvic acid Drugs 0.000 description 7
- 241000239223 Arachnida Species 0.000 description 6
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 6
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
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- 241000258242 Siphonaptera Species 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000002595 Solanum tuberosum Nutrition 0.000 description 6
- 244000061456 Solanum tuberosum Species 0.000 description 6
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- 230000009471 action Effects 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
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- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 229940097012 bacillus thuringiensis Drugs 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
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- IFKONDWPXROQGA-UHFFFAOYSA-N imidazole-1-carbothioic s-acid Chemical compound OC(=S)N1C=CN=C1 IFKONDWPXROQGA-UHFFFAOYSA-N 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
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- 239000002480 mineral oil Substances 0.000 description 5
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- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 5
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- STWNGMSGPBZFMX-UHFFFAOYSA-N pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1.NC(=O)C1=CC=CN=C1 STWNGMSGPBZFMX-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 230000009261 transgenic effect Effects 0.000 description 5
- OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 description 4
- 241000238421 Arthropoda Species 0.000 description 4
- 241000258922 Ctenocephalides Species 0.000 description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 244000166124 Eucalyptus globulus Species 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
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- 240000007594 Oryza sativa Species 0.000 description 4
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 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
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- 229940116861 trichinella britovi Drugs 0.000 description 1
- 229940096911 trichinella spiralis Drugs 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- QFNFRZHOXWNWAQ-UHFFFAOYSA-N triclopyricarb Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NC(Cl)=C(Cl)C=C1Cl QFNFRZHOXWNWAQ-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- BCEHBSKCWLPMDN-MGPLVRAMSA-N voriconazole Chemical compound C1([C@H](C)[C@](O)(CN2N=CN=C2)C=2C(=CC(F)=CC=2)F)=NC=NC=C1F BCEHBSKCWLPMDN-MGPLVRAMSA-N 0.000 description 1
- 229960004740 voriconazole Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12180826.5 | 2012-08-17 | ||
| EP12180826 | 2012-08-17 | ||
| PCT/EP2013/066905 WO2014026984A1 (de) | 2012-08-17 | 2013-08-13 | Azaindolcarbonsäure- und -thiocarbonsäureamide als insektizide und akarizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2881995A1 true CA2881995A1 (en) | 2014-02-20 |
Family
ID=46940225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2881995A Abandoned CA2881995A1 (en) | 2012-08-17 | 2013-08-13 | Azaindole carboxylic acid amides and azaindole thiocarboxylic acid amides for use as insecticides and acaricides |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US9345247B2 (enEXAMPLES) |
| EP (1) | EP2885301A1 (enEXAMPLES) |
| JP (1) | JP2015530990A (enEXAMPLES) |
| KR (1) | KR20150044895A (enEXAMPLES) |
| CN (1) | CN104718206B (enEXAMPLES) |
| AU (1) | AU2013304133B2 (enEXAMPLES) |
| BR (1) | BR112015003098A2 (enEXAMPLES) |
| CA (1) | CA2881995A1 (enEXAMPLES) |
| CL (1) | CL2015000336A1 (enEXAMPLES) |
| CO (1) | CO7200270A2 (enEXAMPLES) |
| IN (1) | IN2015DN01061A (enEXAMPLES) |
| MX (1) | MX2015001897A (enEXAMPLES) |
| PE (1) | PE20150634A1 (enEXAMPLES) |
| PH (1) | PH12015500334A1 (enEXAMPLES) |
| RU (1) | RU2015109064A (enEXAMPLES) |
| WO (1) | WO2014026984A1 (enEXAMPLES) |
| ZA (1) | ZA201501211B (enEXAMPLES) |
Families Citing this family (15)
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| JP2014517079A (ja) | 2011-06-22 | 2014-07-17 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ａｔｒキナーゼ阻害剤として有用な化合物 |
| EP3418281B1 (en) | 2012-12-07 | 2020-09-30 | Vertex Pharmaceuticals Inc. | Pyrazolo[1,5-a]pyrimidines useful as inhibitors of atr kinase for the treatment of cancer diseases |
| WO2014143241A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| WO2014143242A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| US9663519B2 (en) | 2013-03-15 | 2017-05-30 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| ES2768678T3 (es) | 2013-12-06 | 2020-06-23 | Vertex Pharma | Compuesto de 2-amino-6-fluoro-N-[5-fluoro-piridin-3-il]pirazolo[1,5-a]pirimidin-3-carboxamida útil como inhibidor de la ATR quinasa, su preparación, diferentes formas sólidas y derivados radiomarcados de las mismas |
| AR099336A1 (es) | 2014-02-17 | 2016-07-13 | Bayer Cropscience Ag | Indol- y bencimidazolcarboxamidas como insecticidas y acaricidas |
| RU2719583C2 (ru) | 2014-06-05 | 2020-04-21 | Вертекс Фармасьютикалз Инкорпорейтед | Радиоактивно меченные производные 2-амино-6-фтор-n-[5-фтор-пиридин-3-ил]-пиразоло[1, 5-а]пиримидин-3-карбоксамида, используемые в качестве ингибитора atr киназы, препараты на основе этого соединения и его различные твердые формы |
| EP3157566B1 (en) | 2014-06-17 | 2019-05-01 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of chk1 and atr inhibitors |
| CN104974075A (zh) * | 2015-08-07 | 2015-10-14 | 新秀化学（烟台）有限公司 | 一种n, n-二(2,2,6,6-四甲基-4-哌啶基) -1,3-苯二甲酰胺的制备方法 |
| KR102678021B1 (ko) | 2015-09-30 | 2024-06-26 | 버텍스 파마슈티칼스 인코포레이티드 | Dna 손상제와 병용되는, atr 저해제를 포함하는 암 치료용 약제학적 조성물 |
| TWI773657B (zh) | 2015-12-18 | 2022-08-11 | 美商亞德利克斯公司 | 作爲非全身ｔｇｒ５促效劑之經取代之4-苯基吡啶化合物 |
| US12084472B2 (en) | 2015-12-18 | 2024-09-10 | Ardelyx, Inc. | Substituted 4-phenyl pyridine compounds as non-systemic TGR5 agonists |
| CN107094790A (zh) * | 2017-06-12 | 2017-08-29 | 刘鸿宇 | 一种具有协同杀虫作用的农药组合物 |
| WO2021062316A1 (en) * | 2019-09-26 | 2021-04-01 | The Global Alliance For Tb Drug Development, Inc. | Azaindole carboxamide compounds for the treatment of mycobacterial infections |
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| FR2358890A1 (fr) | 1976-05-24 | 1978-02-17 | Science Union & Cie | Nouvelles aryl trifluoroethylamines, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
| WO1992000964A1 (en) | 1990-07-05 | 1992-01-23 | Nippon Soda Co., Ltd. | Amine derivative |
| US20040077605A1 (en) | 2001-06-20 | 2004-04-22 | Salvati Mark E. | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
| RU2266285C2 (ru) | 2001-05-31 | 2005-12-20 | Нихон Нохияку Ко.,Лтд. | Замещенное анилидное производное, его промежуточное соединение, химикаты для борьбы с вредителями сельскохозяйственных и плодовых культур и их использование |
| GB0213715D0 (en) | 2002-06-14 | 2002-07-24 | Syngenta Ltd | Chemical compounds |
| TWI312272B (en) | 2003-05-12 | 2009-07-21 | Sumitomo Chemical Co | Pyrimidine compound and pests controlling composition containing the same |
| EP1479680A1 (en) | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | Azaindole derivatives as Factor Xa inhibitors |
| MXPA05012547A (es) | 2003-05-21 | 2006-05-25 | Prosidion Ltd | Inhibidores de amida de acido pirrolopiridina-2-carboxilico de fosforilasa de glucogeno. |
| UA79404C2 (en) | 2003-10-02 | 2007-06-11 | Basf Ag | 2-cyanobenzenesulfonamide for controlling pests |
| ATE530517T1 (de) | 2003-12-26 | 2011-11-15 | Sumitomo Chemical Co | Nitrilverbindung und deren verwendung bei der schädlingsbekämpfung |
| KR20100017777A (ko) | 2004-02-18 | 2010-02-16 | 이시하라 산교 가부시끼가이샤 | 안트라닐아미드계 화합물, 그의 제조 방법 및 그것을 함유하는 유해 생물 방제제 |
| BRPI0508140B1 (pt) | 2004-03-05 | 2015-03-17 | Nissan Chemical Ind Ltd | Composto benzamida substituída por isoxazolina da fórmula (1); da fórmula (2) substituído por 3,5-bis (aril substituído); da fórmula (4) substituída por alquinibenzeno ou um sal do mesmo; "pesticida, agroquímico, inseticida, parasiticida contendo como ingrediente ativo um ou mais composto benzamida substituída por isoxazolina e sal do mesmo" |
| CN101039922B (zh) | 2004-10-20 | 2011-04-13 | 组合化学工业株式会社 | 3-三唑基苯基硫醚衍生物及含其作为有效成分的杀虫·杀螨·杀线虫剂 |
| DE102005008021A1 (de) | 2005-02-22 | 2006-08-24 | Bayer Cropscience Ag | Spiroketal-substituierte cyclische Ketoenole |
| WO2006100288A2 (en) | 2005-03-24 | 2006-09-28 | Basf Aktiengesellschaft | 2-cyanobenzenesulfonamide compounds for seed treatment |
| EP1932844B1 (en) | 2005-10-06 | 2015-09-02 | Nippon Soda Co., Ltd. | Cross-linked cyclic amine compounds and agents for pest control |
| PT1945632E (pt) | 2005-11-08 | 2013-12-24 | Vertex Pharma | Moduladores heterocíclicos de transportadores de cassete de ligação a atp |
| EP1966199B1 (en) | 2005-11-18 | 2010-10-20 | F. Hoffmann-La Roche AG | Azaindole-2-carboxamide derivatives |
| PE20070847A1 (es) | 2005-11-21 | 2007-09-21 | Basf Ag | Compuestos derivados de 3-amino-1,2-bencisotiazol como insecticidas |
| TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| WO2007101369A1 (fr) | 2006-03-09 | 2007-09-13 | East China University Of Science And Technology | Méthode de préparation et utilisation de composés présentant une action biocide |
| DE102006015468A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
| DE102006015467A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
| DE102006015470A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
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| DE102006033572A1 (de) | 2006-07-20 | 2008-01-24 | Bayer Cropscience Ag | N'-Cyano-N-halogenalkyl-imidamid Derivate |
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| WO2009023179A2 (en) | 2007-08-10 | 2009-02-19 | Genelabs Technologies, Inc. | Nitrogen containing bicyclic chemical entities for treating viral infections |
| GB0720126D0 (en) | 2007-10-15 | 2007-11-28 | Syngenta Participations Ag | Chemical compounds |
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| WO2010069502A2 (de) | 2008-12-18 | 2010-06-24 | Bayer Cropscience Ag | Tetrazolsubstituierte anthranilsäureamide als pestizide |
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| JP2011042643A (ja) * | 2009-07-24 | 2011-03-03 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
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-
2013
- 2013-08-13 KR KR20157003843A patent/KR20150044895A/ko not_active Withdrawn
- 2013-08-13 US US14/421,848 patent/US9345247B2/en not_active Expired - Fee Related
- 2013-08-13 JP JP2015526967A patent/JP2015530990A/ja active Pending
- 2013-08-13 MX MX2015001897A patent/MX2015001897A/es unknown
- 2013-08-13 AU AU2013304133A patent/AU2013304133B2/en not_active Expired - Fee Related
- 2013-08-13 PE PE2015000183A patent/PE20150634A1/es not_active Application Discontinuation
- 2013-08-13 CA CA2881995A patent/CA2881995A1/en not_active Abandoned
- 2013-08-13 WO PCT/EP2013/066905 patent/WO2014026984A1/de active Application Filing
- 2013-08-13 EP EP13753299.0A patent/EP2885301A1/de not_active Withdrawn
- 2013-08-13 CN CN201380054225.9A patent/CN104718206B/zh not_active Expired - Fee Related
- 2013-08-13 BR BR112015003098A patent/BR112015003098A2/pt not_active Application Discontinuation
- 2013-08-13 IN IN1061DEN2015 patent/IN2015DN01061A/en unknown
- 2013-08-13 RU RU2015109064A patent/RU2015109064A/ru not_active Application Discontinuation
-
2015
- 2015-02-10 CO CO15027521A patent/CO7200270A2/es unknown
- 2015-02-12 CL CL2015000336A patent/CL2015000336A1/es unknown
- 2015-02-16 PH PH12015500334A patent/PH12015500334A1/en unknown
- 2015-02-23 ZA ZA2015/01211A patent/ZA201501211B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN104718206B (zh) | 2017-03-08 |
| MX2015001897A (es) | 2015-05-11 |
| CL2015000336A1 (es) | 2015-06-26 |
| JP2015530990A (ja) | 2015-10-29 |
| BR112015003098A2 (pt) | 2017-08-22 |
| AU2013304133A1 (en) | 2015-02-26 |
| IN2015DN01061A (enEXAMPLES) | 2015-06-26 |
| RU2015109064A (ru) | 2016-10-10 |
| KR20150044895A (ko) | 2015-04-27 |
| PH12015500334A1 (en) | 2015-04-20 |
| EP2885301A1 (de) | 2015-06-24 |
| ZA201501211B (en) | 2016-10-26 |
| US20150216175A1 (en) | 2015-08-06 |
| AU2013304133B2 (en) | 2017-02-23 |
| PE20150634A1 (es) | 2015-05-08 |
| CO7200270A2 (es) | 2015-02-27 |
| WO2014026984A1 (de) | 2014-02-20 |
| CN104718206A (zh) | 2015-06-17 |
| US9345247B2 (en) | 2016-05-24 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |
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