JP5567483B2 - 殺虫性置換アジニル誘導体 - Google Patents
殺虫性置換アジニル誘導体 Download PDFInfo
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- JP5567483B2 JP5567483B2 JP2010528937A JP2010528937A JP5567483B2 JP 5567483 B2 JP5567483 B2 JP 5567483B2 JP 2010528937 A JP2010528937 A JP 2010528937A JP 2010528937 A JP2010528937 A JP 2010528937A JP 5567483 B2 JP5567483 B2 JP 5567483B2
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- Japan
- Prior art keywords
- alkyl
- compound
- insecticides
- herbicides
- mmol
- 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.)
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- 230000000749 insecticidal effect Effects 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 100
- 239000000203 mixture Substances 0.000 claims description 53
- 239000000460 chlorine Substances 0.000 claims description 32
- 241000238631 Hexapoda Species 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 241000607479 Yersinia pestis Species 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 6
- 238000005507 spraying Methods 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 229910004013 NO 2 Inorganic materials 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 230000000415 inactivating effect Effects 0.000 claims description 2
- 230000003071 parasitic effect Effects 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- -1 aryl isocyanate Chemical class 0.000 description 100
- 239000002917 insecticide Substances 0.000 description 72
- 239000004009 herbicide Substances 0.000 description 67
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 52
- 238000002360 preparation method Methods 0.000 description 33
- 235000019439 ethyl acetate Nutrition 0.000 description 31
- 238000005481 NMR spectroscopy Methods 0.000 description 29
- 239000007787 solid Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 229910000104 sodium hydride Inorganic materials 0.000 description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000002480 mineral oil Substances 0.000 description 14
- 235000010446 mineral oil Nutrition 0.000 description 14
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 10
- 241000894007 species Species 0.000 description 10
- 239000012267 brine Substances 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000000895 acaricidal effect Effects 0.000 description 6
- 239000000642 acaricide Substances 0.000 description 6
- 239000000417 fungicide Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- NLLAAEGNVMYAPC-UHFFFAOYSA-N 2-isocyanato-4,6-bis(2,2,2-trifluoroethoxy)pyrimidine Chemical compound FC(F)(F)COC1=CC(OCC(F)(F)F)=NC(N=C=O)=N1 NLLAAEGNVMYAPC-UHFFFAOYSA-N 0.000 description 5
- 241001674044 Blattodea Species 0.000 description 5
- 241000255967 Helicoverpa zea Species 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 5
- 241000256247 Spodoptera exigua Species 0.000 description 5
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 5
- 235000005911 diet Nutrition 0.000 description 5
- 230000037213 diet Effects 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 241000238876 Acari Species 0.000 description 4
- 241000193388 Bacillus thuringiensis Species 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- 239000002169 Metam Substances 0.000 description 4
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- QUBYOSBFZXPRQF-UHFFFAOYSA-N 1-(4,6-dichloropyrimidin-2-yl)-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC1=NC(Cl)=CC(Cl)=N1 QUBYOSBFZXPRQF-UHFFFAOYSA-N 0.000 description 3
- VZLYVCHVCZQNSG-UHFFFAOYSA-N 1-[4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl]-1,3-dimethyl-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C=1C=C(OC(F)(F)F)C=CC=1N(C)C(=O)N(C)C1=NC(OCC(F)(F)F)=CC(OCC(F)(F)F)=N1 VZLYVCHVCZQNSG-UHFFFAOYSA-N 0.000 description 3
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 3
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 3
- QFASYRUWYPGOAD-UHFFFAOYSA-N 3-[4,6-bis(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]-1-(4-chlorophenyl)-1-methylurea Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)NC1=NC(OCC(F)(F)F)=NC(OCC(F)(F)F)=N1 QFASYRUWYPGOAD-UHFFFAOYSA-N 0.000 description 3
- ROUNXOYQOPFXKZ-UHFFFAOYSA-N 3-chloro-2,5,6-trifluoro-4-(2,2,2-trifluoroethoxy)pyridine Chemical compound FC1=NC(F)=C(Cl)C(OCC(F)(F)F)=C1F ROUNXOYQOPFXKZ-UHFFFAOYSA-N 0.000 description 3
- LFEAHBDLFGUZBC-UHFFFAOYSA-N 4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-amine Chemical compound NC1=NC(OCC(F)(F)F)=CC(OCC(F)(F)F)=N1 LFEAHBDLFGUZBC-UHFFFAOYSA-N 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 3
- 241000255777 Lepidoptera Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 241001674048 Phthiraptera Species 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 229910021538 borax Inorganic materials 0.000 description 3
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000012039 electrophile Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002540 isothiocyanates Chemical class 0.000 description 3
- 239000002949 juvenile hormone Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 244000144972 livestock Species 0.000 description 3
- 229960002523 mercuric chloride Drugs 0.000 description 3
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920001021 polysulfide Polymers 0.000 description 3
- 239000005077 polysulfide Substances 0.000 description 3
- 150000008117 polysulfides Polymers 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 239000002728 pyrethroid Substances 0.000 description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004328 sodium tetraborate Substances 0.000 description 3
- 235000010339 sodium tetraborate Nutrition 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 2
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 2
- FHNKBSDJERHDHZ-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C)C=C1C FHNKBSDJERHDHZ-UHFFFAOYSA-N 0.000 description 2
- RLLPVAHGXHCWKJ-MJGOQNOKSA-N (3-phenoxyphenyl)methyl (1r,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-MJGOQNOKSA-N 0.000 description 2
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 2
- WCHKNEDTMBMBJM-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[3-fluoro-4,6-bis(2,2,2-trifluoroethoxy)pyridin-2-yl]-1-methylurea Chemical compound C=1C=C(Br)C=CC=1N(C)C(=O)NC1=NC(OCC(F)(F)F)=CC(OCC(F)(F)F)=C1F WCHKNEDTMBMBJM-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- OAAJLDRFNKBIIG-UHFFFAOYSA-N 1-[4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)COC1=CC(OCC(F)(F)F)=NC(NC(=O)NC=2C=CC(=CC=2)C(F)(F)F)=N1 OAAJLDRFNKBIIG-UHFFFAOYSA-N 0.000 description 2
- PWIFLQINXQLLCF-UHFFFAOYSA-N 1-[4-(2,2,2-trifluoroethoxy)-6-(trifluoromethyl)pyrimidin-2-yl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound FC(F)(F)COC1=CC(C(F)(F)F)=NC(NC(=O)NC=2C=CC(=CC=2)C(F)(F)F)=N1 PWIFLQINXQLLCF-UHFFFAOYSA-N 0.000 description 2
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 2
- QZTWVDCKDWZCLV-UHFFFAOYSA-N 1-isocyanato-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(N=C=O)C=C1 QZTWVDCKDWZCLV-UHFFFAOYSA-N 0.000 description 2
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 2
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 2
- JYSIMRURBJGMJM-UHFFFAOYSA-N 2-azido-5-chloro-3-fluoro-4,6-bis(2,2,2-trifluoroethoxy)pyridine Chemical compound FC1=C(N=[N+]=[N-])N=C(OCC(F)(F)F)C(Cl)=C1OCC(F)(F)F JYSIMRURBJGMJM-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- ZKUISVQUELKCDL-UHFFFAOYSA-N 2-isocyanato-4,6-bis(2,2,2-trifluoroethoxy)-1h-triazine Chemical compound FC(F)(F)COC1=CC(OCC(F)(F)F)=NN(N=C=O)N1 ZKUISVQUELKCDL-UHFFFAOYSA-N 0.000 description 2
- HBLSGPQATABNRY-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-n-methyl-4-n,5-n-bis(trifluoromethyl)-1,3-thiazolidine-2,4,5-triimine Chemical compound CN=C1SC(=NC(F)(F)F)C(=NC(F)(F)F)N1C1=CC=C(Cl)C=C1 HBLSGPQATABNRY-UHFFFAOYSA-N 0.000 description 2
- VGOPATMBUUGMCV-UHFFFAOYSA-N 3-[4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl]-1-(4-chlorophenyl)-1-methoxyurea Chemical compound C=1C=C(Cl)C=CC=1N(OC)C(=O)NC1=NC(OCC(F)(F)F)=CC(OCC(F)(F)F)=N1 VGOPATMBUUGMCV-UHFFFAOYSA-N 0.000 description 2
- KBIPSMDVXHMWPU-UHFFFAOYSA-N 3-[4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl]-1-methyl-1-[4-(trifluoromethoxy)phenyl]urea Chemical compound C=1C=C(OC(F)(F)F)C=CC=1N(C)C(=O)NC1=NC(OCC(F)(F)F)=CC(OCC(F)(F)F)=N1 KBIPSMDVXHMWPU-UHFFFAOYSA-N 0.000 description 2
- ZATJKHMEUOFCDS-UHFFFAOYSA-N 3-[4,6-bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl]-1-methyl-1-[4-(trifluoromethyl)phenyl]thiourea Chemical compound C=1C=C(C(F)(F)F)C=CC=1N(C)C(=S)NC1=NC(OCC(F)(F)F)=CC(OCC(F)(F)F)=N1 ZATJKHMEUOFCDS-UHFFFAOYSA-N 0.000 description 2
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- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 description 1
- 229960002245 selamectin Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- MSGMXYUAWZYTFC-UHFFFAOYSA-N sodium;2,2,2-trifluoroethanolate Chemical compound [Na+].[O-]CC(F)(F)F MSGMXYUAWZYTFC-UHFFFAOYSA-N 0.000 description 1
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- NMGNJWORLGLLHQ-UHFFFAOYSA-M sulcofuron-sodium Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 NMGNJWORLGLLHQ-UHFFFAOYSA-M 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 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
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 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
- VHXDHGALQPVNKI-UHFFFAOYSA-N thiadiazol-4-ylurea Chemical compound NC(=O)NC1=CSN=N1 VHXDHGALQPVNKI-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 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
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- 125000004001 thioalkyl group Chemical group 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
- 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
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- PYNKFIVDSJSNGL-UHFFFAOYSA-N thiosultap Chemical compound OS(=O)(=O)SCC(N(C)C)CSS(O)(=O)=O PYNKFIVDSJSNGL-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 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
- 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
- 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
- 230000000699 topical effect Effects 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-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
- 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
- LTQZKHRCYAXPAZ-UHFFFAOYSA-N triazin-4-ylsulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=NN=N1 LTQZKHRCYAXPAZ-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 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
- 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
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
- WCTAGTRAWPDFQO-UHFFFAOYSA-K trisodium;hydrogen carbonate;carbonate Chemical compound [Na+].[Na+].[Na+].OC([O-])=O.[O-]C([O-])=O WCTAGTRAWPDFQO-UHFFFAOYSA-K 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin 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-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- 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<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- 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
- A61P33/14—Ectoparasiticides, e.g. scabicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Tropical Medicine & Parasitology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Description
A、BおよびDは、N、CHまたはCR3を表し、ただし、A、BまたはDのうちの少なくとも1つは、Nであり、
R1が、1個から最大数までのフッ素または塩素原子で置換されていてもよいC1〜C4アルキルを表し、
R2が、Cl、CF3、O(C1〜C3アルキル)、NH(C1〜C3アルキル)またはN(C1〜C3アルキル)2を表し、前記C1〜C3アルキル基の各々は、1個から最大数までのフッ素原子で置換されていてもよく、
R3が、H、F、Cl、Br、I、C1〜C3アルキルまたはO(C1〜C3アルキル)を表し、前記C1〜C3アルキル基の各々は、1個から最大数までのフッ素原子で置換されていてもよく、
R4が、H、C1〜C3アルキル(アルコキシ、ベンジルオキシまたは−OC(O)R7で置換されていてもよい)、またはCO2R6を表し、
R5は、H、C1〜C3アルキル(C1〜C3アルコキシ、F、CNまたはCO2Rで置換されていてもよい)、OH、C1〜C3アルコキシまたはCO2R6を表し、あるいは、R4およびR5が、一緒になって−CH2CH2−または−C(O)CH2−を表し、
R6が、HまたはC1〜C3アルキルを表し、
R7が、C1〜C3アルキルを表し、
Wが、OまたはSを表し、
Arが、F、Cl、Br、I、NO2、CN、SCF3、SO2CF3、1個から最大数までの塩素もしくはフッ素原子で置換されているC1〜C3アルキル、または1個から最大数までの塩素もしくはフッ素原子で置換されていてもよいC1〜C3アルコキシから独立して選択される1〜4個の置換基で置換されているフェニル基を表すか、
XおよびYが、H、F、Cl、Br、I、NO2、CN、SCF3、SO2CF3、1個から最大数までの塩素もしくはフッ素原子で置換されているC1〜C3アルキル、または1個から最大数までの塩素もしくはフッ素原子で置換されていてもよいC1〜C3アルコキシを独立して表す。
(1)R1が、CH2CF3である式(I)の化合物、
(2)R2が、OCH2CF3である式(I)の化合物、
(3)Wが、Oである式(I)の化合物、
(4)R4およびR5が、独立して、HまたはCH3である式(I)の化合物、
(5)Arが、
(6)Xが、Br、Cl、CF3またはOCF3である式(I)の化合物を包含する。
表1に同定されている化合物を、以下の通り、ビートアーミーワームおよびコーンイヤーワームに対して試験した。
試験溶液を調製するために、試験化合物を、アセトン:水道水=9:1の2mL当たり4mgとして2000ppm溶液にて製剤化した。2000ppm(食餌表面積に対する投与量50μg/cm2に相当する)試験溶液50μLを、1昆虫種当たり8個のウェル(1ウェル=1複製)の各々に含有される鱗翅目食餌(Southland Multi-Species Lepidopteran Diet)1mLの表面にピペットで移した。溶媒を風乾したらすぐに、2齢のコーンイヤーワームおよびビートアーミーワームを各ウェル内の処理食餌の上に置いた。処理食餌および幼虫を含有するトレイを覆い、次いで、5日わたって25℃、50〜55%RH、および16時間照明し、8時間暗くしてグロースチャンバー内に保持した。観察は、処理および寄生から5日後に行った。次いで、1回の処理につき1種当たり8匹のうちの死んだ昆虫の数を決定した。結果は、50mg/cm2の投与量における防除率として表2に示す。
本発明の化合物は、昆虫を包含する無脊椎動物の防除に有用である。したがって、本発明は、昆虫の生息場所に、保護するべき地域に、または防除すべき昆虫の上に直接、昆虫阻害量の式(I)の化合物を散布することを含む昆虫を阻害するための方法も対象とする。本発明の化合物は、ダニおよび線虫などの他の無脊椎動物害虫を防除するために使用することもできる。
鱗翅目−ヘリオチス属(Heliothis)種、ヘリコベルパ属(Helicoverpa)種、スポドプテラ属(Spodoptera)種、アメリカキヨトウ(Mythimna unipuncta)、タマナヤガ(Agrotis ipsilon)、エアリアス属(Earias)種、ユーキソアアウキシリアリス(Euxoa auxiliaris)、イラクサギンウワバ(Trichoplusia ni)、アンチカルシアゲマタリス(Anticarsia gemmatalis)、ラキプルシアヌ(Rachiplusia nu)、コナガ(Plutella xylostella)、チロ属(Chilo)種、イッテンオオメイガ(Scirpophaga incertulas)、イネヨトウ(Sesamia inferens)、コブノメイガ(Cnaphalocrocis medinalis)、ヨーロッパアワノメイガ(Ostrinia nubilalis)、コドリンガ(Cydia pomonella)、モモシンクイガ(Carposina niponensis)、コカクモンハマキ(Adoxophyes orana)、リンゴシロモンハマキ(Archips argyrospilus)、トビハマキ(Pandemis heparana)、エピノチアアポレマ(Epinotia aporema)、ブドウホソハマキ(Eupoecilia ambiguella)、ホソバヒメハマキ(Lobesia botrana)、ブドウヒメハマキ(Polychrosis viteana)、ワタアカミムシガ(Pectinophora gossypiella)、モンシロチョウ(Pieris rapae)、フィロノリクテル属(Phyllonorycter)種、ロイコプテラマリフォリエラ(Leucoptera malifoliella)、ミカンハモグリガ(Phyllocnisitis citrella)
鞘翅目−ディアブロチカ属(Diabrotica)種、コロラドハムシ(Leptinotarsa decemlineata)、イネドロオイムシ(Oulema oryzae)、ワタミハナゾウムシ(Anthonomus grandis)、イネミズゾウムシ(Lissorhoptrus oryzophilus)、アグリオテス属(Agriotes)種、メラノタスコムニス(Melanotus communis)、マメコガネ(Popillia japonica)、シクロセファラ属(Cyclocephala)種、トリボリウム属(Tribolium)種
同翅目−アフィス属(Aphis)種、モモアカアブラムシ(Myzus persicae)、ロパロシフム属(Rhopalosiphum)種、オオバコアブラムシ(Dysaphis plantaginea)、トキソプテラ属(Toxoptera)種、チューリップヒゲナガアブラムシ(Macrosiphum euphorbiae)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、ムギヒゲナガアブラムシ(Sitobion avenae)、ムギウスイロアブラムシ(Metopolophium dirhodum)、ムギミドリアブラムシ(Schizaphis graminum)、ブラキコルスノキウス(Brachycolus noxius)、ネフォテティクス属(Nephotettix)種、トビイロウンカ(Nilaparvata lugens)、セジロウンカ(Sogatella furcifera)、ヒメトビウンカ(Laodelphax striatellus)、タバココナジラミ(Bemisia tabaci)、オンシツコナジラミ(Trialeurodes vaporariorum)、アレウロデスプロレテラ(Aleurodes proletella)、ミカンワタコナジラミ(Aleurothrixus floccosus)、ナシマルカイガラムシ(Quadraspidiotus perniciosus)、ヤノネカイガラムシ(Unaspis yanonensis)、ルビーロウカイガラムシ(Ceroplastes rubens)、アカマルカイガラムシ(Aonidiella aurantii)
半翅目−リグス属(Lygus)種、エウリガスターマウラ(Eurygaster maura)、ミナミアオカメムシ(Nezara viridula)、ピエゾドルスグイルディンギ(Piezodorus guildingi)、レプトコリサバリコルニス(Leptocorisa varicornis)、トコジラミ(Cimex lectularius)、タイワントコジラミ(Cimex hemipterus)
総翅目−フランクリニエラ属(Frankliniella)種、トリプス属(Thrips)種、チャノキイロアザミウマ(Scirtothrips dorsalis)
等翅目−キアシシロアリ(Reticulitermes flavipes)、イエシロアリ(Coptotermes formosanus)、レティキュリテルメスヴィルジニカス(Reticulitermes virginicus)、ヘテロテルメスアウレウス(Heterotermes aureus)、レティキュリテルメスヘスペラス(Reticulitermes hesperus)、コプトテルメスフレンチイ(Coptotermes frenchii)、シェドライノテルメス属(Shedorhinotermes)種、レティキュリテルメスサントネンシス(Reticulitermes santonensis)、レティキュリテルメスグラッセイ(Reticulitermes grassei)、レティキュリテルメスバニュレンシス(Reticulitermes banyulensis)、ヤマトシロアリ(Reticulitermes speratus)、レティキュリテルメスハゲニ(Reticulitermes hageni)、レティキュリテルメスチビアリス(Reticulitermes tibialis)、ズーテルモプシス属(Zootermopsis)種、インシシテルメス属(Incisitermes)種、マルギニテルメス属(Marginitermes)種、マクロテルメス属(Macrotermes)種、ミクロセロテルメス属(Microcerotermes)種、ミクロテルメス属(Microtermes)種
双翅目−リリオミザ属(
)種、イエバエ(Musca domestica)、アエデス属(Aedes)種、クレクス属(Culex)種、アノフェレス属(Anopheles)種、ファニア属(Fannia)種、ストモキス属(Stomoxys)種
膜翅目−アルゼンチンアリ(Iridomyrmex humilis)、ソレノプシス属(Solenopsis)種、イエヒメアリ(Monomorium pharaonis)、アッタ属(Atta)種、ポゴノミルメクス属(Pogonomyrmex)種、カンポノツス属(Camponotus)種、モノモリウム属(Monomorium)種、コヌカアリ(Tapinoma sessile)、テトラモリウム属(Tetramorium)種、キシロカパ属(Xylocapa)種、ベスプラ属(Vespula)種、ポリステス属(Polistes)種
食毛目(咬むシラミ)
裸尾目(吸血シラミ)−ケジラミ(Pthirus pubis)、ペディキュラス属(Pediculus)種
直翅目(バッタ、コオロギ)−メラノプルス属(Melanoplus)種、トノサマバッタ(Locusta migratoria)、サバクトビバッタ(Schistocerca gregaria)、ケラ科(Gryllotalpidae)(ケラ)。
ゴキブリ科(ゴキブリ)−トウヨウゴキブリ(Blatta orientalis)、チャバネゴキブリ(Blattella germanica)、ワモンゴキブリ(Periplaneta americana)、チャオビゴキブリ(Supella longipalpa)、コワモンゴキブリ(Periplaneta australasiae)、トビイロゴキブリ(Periplaneta brunnea)、パルコブラッタペンシルヴァニカ(Parcoblatta pennsylvanica)、クロゴキブリ(Periplaneta fuliginosa)、オガサワラゴキブリ(Pycnoscelus surinamensis)、
隠翅目−クテノファリデス属(Ctenophalides)種、ヒトノミ(Pulex irritans)
ダニ類−テトラニクス属(Tetranychus)種、パノニクス属(Panonychus)種、エオテトラニクスカルピニ(Eotetranychus carpini)、ミカンサビダニ(Phyllocoptruta oleivora)、アクルスペレカッシイ(Aculus pelekassi)、ミナミヒメハダニ(Brevipalpus phoenicis)、ブーフィルス属(Boophilus)種、アメリカイヌカクマダニ(Dermacentor variabilis)、クリイロコイタマダニ(Rhipicephalus sanguineus)、アメリカキララマダニ(Amblyomma americanum)、イクソデス属(Ixodes)種、ネコショウセンコウヒゼンダニ(Notoedres cati)、ヒゼンダニ(Sarcoptes scabiei)、デルマトファゴイデス属(Dermatophagoides)種
線形動物−犬糸状虫(Dirofilaria immitis)、メロイドギネ属(Meloidogyne)種、ヘテロデラ属(Heterodera)種、ホプロライムスコロンブス(Hoplolaimus columbus)、ベロノライムス属(Belonolaimus)種、プラチレンクス属(Pratylenchus)種、ロチレンクスレニフォルミス(Rotylenchus reniformis)、クリコネメラオルナタ(Criconemella ornata)、ディチレンクス属(Ditylenchus)種、イネシンガレセンチュウ(Aphelenchoides besseyi)、ヒルシュマンニエラ属(Hirschmanniella)種を包含するが、これらに限定されるものではない。
本発明の化合物は、本発明の重要な実施形態であり、本発明の化合物および植物学的に許容できる不活性担体を含む組成物の形態で散布される。害虫の防除は、スプレー剤、局所処理、ゲル剤、種子コーティング剤、マイクロカプセル化、全身性取り込み、ベイト剤、イヤータグ剤、ボーラス剤、煙霧剤(fogger)、燻蒸剤、エアロゾル剤、ダスト剤および多くの他の形態で本発明の化合物を散布することにより達成される。組成物は、散布のために水に分散される濃縮された固体か液体のどちらかの製剤であるか、さらに処理することなく散布されるダストまたは顆粒の製剤である。組成物は、農芸化学技術において伝統的であるが、本発明の化合物がその中に存在するために新規かつ重要である手順および製法に従って調製される。しかしながら、農芸化学者が任意の望ましい組成物を容易に製造することができるようにするために、組成物の製剤化に関して一部を説明することとする。
キサクリム、フェンピロキシメート、FKI−1033、フルベンジアミド、HGW86、ヒドラメチルノン、IKI−2002、イソプロチオラン、マロノベン、メタフルミゾン、メトキサジアゾン、ニフルリジド、NNI−9850、NNI−0101、ピメトロジン、ピリダベン、ピリダリル、Qcide、ラフォキサニド、リナキシピル、SYJ−159、トリアラテンおよびトリアザメートなどの未分類殺虫剤ならびにそれらの任意の組合せを包含する。
Claims (8)
- 式(I)の化合物
A、BおよびDは、N、CHまたはCR3を表し、ただし、A、BまたはDのうちの2つのみがNであり、
R1が、1個から最大数までのフッ素または塩素原子で置換されているC1〜C4アルキルを表し、
R2が、Cl、CF3、O(C1〜C3アルキル)、NH(C1〜C3アルキル)またはN(C1〜C3アルキル)2を表し、C1〜C3アルキル基の各々は、1個から最大数までのフッ素原子で置換されていてもよく、
R3が、H、F、Cl、Br、I、C1〜C3アルキルまたはO(C1〜C3アルキル)を表し、C1〜C3アルキル基の各々は、1個から最大数までのフッ素原子で置換されていてもよく、
R4が、H、C1〜C3アルキル(アルコキシ、ベンジルオキシまたは−OC(O)R7で置換されていてもよい)、またはCO2R6を表し、
R5が、H、C1〜C3アルキル(C1〜C3アルコキシ、F、CNまたはCO2Rで置換されていてもよい)、OH、C1〜C3アルコキシまたはCO2R6を表し、あるいは、R4およびR5が、一緒になって−CH2CH2−または−C(O)CH2−を表し、
R6が、HまたはC1〜C3アルキルを表し、
R7が、C1〜C3アルキルを表し、
Wが、OまたはSを表し、
Arが、F、Cl、Br、I、NO2、CN、SCF3、SO2CF3、1個から最大数までの塩素もしくはフッ素原子で置換されているC1〜C3アルキル、または1個から最大数までの塩素もしくはフッ素原子で置換されていてもよいC1〜C3アルコキシから独立して選択される1〜4個の置換基で置換されているフェニル基を表すか、
XおよびYが、H、F、Cl、Br、I、NO2、CN、SCF3、SO2CF3、1個から最大数までの塩素もしくはフッ素原子で置換されているC1〜C3アルキル、または1個から最大数までの塩素もしくはフッ素原子で置換されていてもよいC1〜C3アルコキシを独立して表す)。 - R1が、CH2CF3である、請求項1に記載の化合物。
- R2が、OCH2CF3である、請求項1に記載の化合物。
- Wが、Oである、請求項1に記載の化合物。
- R4およびR5が、独立して、HまたはCH3である、請求項1に記載の化合物。
- Xが、Br、Cl、CF3またはOCF3である、請求項1に記載の化合物。
- 植物学的に許容できる担体との組合せで請求項1に記載の化合物を含む、昆虫を防除するための組成物。
- 昆虫不活性化量の請求項1に記載の化合物を、防除が望まれる生息場所に散布することを含む、ヒトに対して寄生性であるか感染性疾患を伝染することができる無脊椎動物および/または線形動物の害虫を除く昆虫を防除する方法。
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US4747870A (en) * | 1986-05-02 | 1988-05-31 | E. I. Du Pont De Nemours And Company | Herbicidal pyrazole sulfonamides |
GB8700838D0 (en) | 1987-01-15 | 1987-02-18 | Shell Int Research | Termiticides |
US5399564A (en) | 1991-09-03 | 1995-03-21 | Dowelanco | N-(4-pyridyl or 4-quinolinyl) arylacetamide and 4-(aralkoxy or aralkylamino) pyridine pesticides |
WO2003030909A1 (en) | 2001-09-25 | 2003-04-17 | Bayer Pharmaceuticals Corporation | 2- and 4-aminopyrimidines n-substtituded by a bicyclic ring for use as kinase inhibitors in the treatment of cancer |
US6693097B2 (en) | 2001-11-30 | 2004-02-17 | Synta Pharmaceuticals Corp. | Pyrimidine compounds |
EP1490015B1 (en) | 2002-03-15 | 2009-09-23 | Wayne State University | Novel 2-amino-9-((2-hydroxymethyl) cyclopropylidenemethyl) purines as antiviral agents |
TW200407315A (en) | 2002-04-23 | 2004-05-16 | Sankyo Co | Pyrimidine derivatives |
CN1508130A (zh) | 2002-12-18 | 2004-06-30 | 中国科学院大连化学物理研究所 | N-苯基-n’-嘧啶基取代脲类衍生物的合成方法 |
CN1510033A (zh) * | 2002-12-24 | 2004-07-07 | 中国科学院大连化学物理研究所 | 一种合成非对称二吡啶基取代脲类衍生物的新方法 |
WO2008007788A1 (fr) | 2006-07-14 | 2008-01-17 | Asahi Glass Company, Limited | Structure et son procédé de fabrication |
FR2910477B1 (fr) | 2006-12-22 | 2009-04-10 | Total France Sa | Fluxant et ses applications. |
ES2532119T3 (es) * | 2007-10-09 | 2015-03-24 | Dow Agrosciences Llc | Derivados de azinilo sustituido insecticidas |
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2008
- 2008-09-26 ES ES08837395.6T patent/ES2532119T3/es active Active
- 2008-09-26 US US12/239,079 patent/US8013154B2/en active Active
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- 2008-09-26 EP EP08837395.6A patent/EP2195302B1/en not_active Not-in-force
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US20120190684A1 (en) | 2012-07-26 |
US8455649B2 (en) | 2013-06-04 |
ES2532119T3 (es) | 2015-03-24 |
JP5813825B2 (ja) | 2015-11-17 |
JP2011500574A (ja) | 2011-01-06 |
US8507671B2 (en) | 2013-08-13 |
WO2009048752A2 (en) | 2009-04-16 |
JP5826327B2 (ja) | 2015-12-02 |
AR068835A1 (es) | 2009-12-09 |
EP2195302B1 (en) | 2015-02-18 |
JP2014205678A (ja) | 2014-10-30 |
JP2014208648A (ja) | 2014-11-06 |
EP2195302A2 (en) | 2010-06-16 |
US8013154B2 (en) | 2011-09-06 |
WO2009048752A3 (en) | 2009-05-28 |
US20090093486A1 (en) | 2009-04-09 |
US20120190683A1 (en) | 2012-07-26 |
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