JP2003516941A - 動物における節足動物の制御 - Google Patents
動物における節足動物の制御Info
- Publication number
- JP2003516941A JP2003516941A JP2001541880A JP2001541880A JP2003516941A JP 2003516941 A JP2003516941 A JP 2003516941A JP 2001541880 A JP2001541880 A JP 2001541880A JP 2001541880 A JP2001541880 A JP 2001541880A JP 2003516941 A JP2003516941 A JP 2003516941A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- haloalkyl
- alkyl
- formula
- optionally substituted
- 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.)
- Pending
Links
- 241001465754 Metazoa Species 0.000 title claims abstract description 63
- 241000238421 Arthropoda Species 0.000 title description 10
- 238000000034 method Methods 0.000 claims abstract description 21
- 244000045947 parasite Species 0.000 claims abstract description 16
- 125000004961 1-arylpyrazolyl group Chemical group 0.000 claims abstract description 8
- 239000002895 emetic Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 113
- 125000001188 haloalkyl group Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical group 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 27
- -1 dichloro-4-trifluoromethylphenyl Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 244000144972 livestock Species 0.000 claims description 14
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 3
- UEPSJINPZROQIC-UHFFFAOYSA-N 5-oxo-4-(trifluoromethylsulfanyl)-1,2-dihydropyrazole-3-carbonitrile Chemical group C(#N)C1=NNC(=C1SC(F)(F)F)O UEPSJINPZROQIC-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Chemical group 0.000 claims 1
- 235000002639 sodium chloride Nutrition 0.000 description 38
- 238000005481 NMR spectroscopy Methods 0.000 description 22
- 241000282472 Canis lupus familiaris Species 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 241000282326 Felis catus Species 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 238000011282 treatment Methods 0.000 description 12
- 241000254173 Coleoptera Species 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 241000607479 Yersinia pestis Species 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 125000006414 CCl Chemical group ClC* 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 241000258242 Siphonaptera Species 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000255925 Diptera Species 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 206010047700 Vomiting Diseases 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000002917 insecticide Substances 0.000 description 6
- 235000012054 meals Nutrition 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 241000244206 Nematoda Species 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 244000000013 helminth Species 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 230000008673 vomiting Effects 0.000 description 4
- 241001327638 Cimex lectularius Species 0.000 description 3
- 241000258924 Ctenocephalides felis Species 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NZJKXSDLYWXVCK-UHFFFAOYSA-N OC1=C(S(=O)(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl Chemical compound OC1=C(S(=O)(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl NZJKXSDLYWXVCK-UHFFFAOYSA-N 0.000 description 3
- GMDSKVRWVVCECJ-UHFFFAOYSA-N OC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl Chemical compound OC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GMDSKVRWVVCECJ-UHFFFAOYSA-N 0.000 description 3
- MOTUUCXKXATGKU-UHFFFAOYSA-N OC1=C(SC(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl Chemical compound OC1=C(SC(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl MOTUUCXKXATGKU-UHFFFAOYSA-N 0.000 description 3
- 240000006394 Sorghum bicolor Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000011097 chromatography purification Methods 0.000 description 3
- 239000002285 corn oil Substances 0.000 description 3
- 235000005687 corn oil Nutrition 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- 230000037213 diet Effects 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 2
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- PJSJZVGSFJIWAN-UHFFFAOYSA-N 5-methylsulfanyl-1,2-dihydropyrazol-3-one Chemical compound CSC1=NNC(=C1)O PJSJZVGSFJIWAN-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000005660 Abamectin Substances 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- 241000490513 Ctenocephalides canis Species 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 241000257324 Glossina <genus> Species 0.000 description 2
- 108010034145 Helminth Proteins Proteins 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 239000005912 Lufenuron Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
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- 241001674048 Phthiraptera Species 0.000 description 2
- 241001675082 Pulex Species 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 241001481696 Rhipicephalus sanguineus Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
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- 241000353223 Xenopsylla cheopis Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003096 antiparasitic agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- 238000006243 chemical reaction Methods 0.000 description 2
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
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- 238000011156 evaluation Methods 0.000 description 2
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- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000036449 good health Effects 0.000 description 2
- 125000004992 haloalkylamino group Chemical group 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
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- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 description 1
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- 239000004575 stone Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000004916 vomit Anatomy 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000004018 waxing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N47/02—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 no bond to a nitrogen atom
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
-
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16865899P | 1999-12-02 | 1999-12-02 | |
| US60/168,658 | 1999-12-02 | ||
| PCT/EP2000/012100 WO2001040195A2 (en) | 1999-12-02 | 2000-12-01 | Control of arthropods in animals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003516941A true JP2003516941A (ja) | 2003-05-20 |
| JP2003516941A5 JP2003516941A5 (enExample) | 2008-12-04 |
Family
ID=22612402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001541880A Pending JP2003516941A (ja) | 1999-12-02 | 2000-12-01 | 動物における節足動物の制御 |
Country Status (20)
| Country | Link |
|---|---|
| US (4) | US6569886B2 (enExample) |
| EP (1) | EP1237873B1 (enExample) |
| JP (1) | JP2003516941A (enExample) |
| KR (1) | KR100816914B1 (enExample) |
| CN (2) | CN1939909A (enExample) |
| AR (1) | AR033504A1 (enExample) |
| AU (1) | AU784798B2 (enExample) |
| BR (1) | BR0015945A (enExample) |
| CA (1) | CA2393197C (enExample) |
| CO (1) | CO5261614A1 (enExample) |
| CZ (1) | CZ20021898A3 (enExample) |
| ES (1) | ES2409630T3 (enExample) |
| HU (1) | HUP0300357A3 (enExample) |
| IL (2) | IL149856A0 (enExample) |
| MX (1) | MXPA02005511A (enExample) |
| MY (1) | MY129771A (enExample) |
| PL (1) | PL364874A1 (enExample) |
| TW (1) | TWI290137B (enExample) |
| WO (1) | WO2001040195A2 (enExample) |
| ZA (1) | ZA200204336B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011219420A (ja) * | 2010-04-09 | 2011-11-04 | Otsuka Agritechno Co Ltd | 新規なピラゾール化合物、その製造方法及び有害生物防除剤 |
| JP2014084307A (ja) * | 2012-10-25 | 2014-05-12 | Nagoya Institute Of Technology | 新規トリフロン誘導体及びその製造方法 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602004022985D1 (de) | 2003-12-24 | 2009-10-15 | Bayer Cropscience Ag | Regulation des pflanzenwachstums |
| 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" |
| US20050234119A1 (en) * | 2004-04-16 | 2005-10-20 | Soll Mark D | Antiparasitical agents and methods for treating, preventing and controlling external parasites in animals |
| FR2869905B1 (fr) | 2004-05-10 | 2008-09-05 | Sanofi Synthelabo | Procede de preparation d'ester de l'acide 1,5-diphenylpyrazole carboxylique. |
| GB0413970D0 (en) | 2004-06-22 | 2004-07-28 | Syngenta Participations Ag | Chemical compounds |
| UY28617A1 (es) * | 2004-11-12 | 2006-06-30 | Popley Pharma Ltda | Nuevas composiciones |
| US7923465B2 (en) | 2005-06-02 | 2011-04-12 | Glenmark Pharmaceuticals S.A. | Cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| DK2182945T3 (en) | 2007-06-27 | 2015-11-16 | Du Pont | PROCEDURE TO COMBAT PESTS WITH ANIMALS |
| EA020923B1 (ru) * | 2008-11-19 | 2015-02-27 | Мериал Лимитед | Производные димерного 1-арилпиразола |
| WO2010059529A2 (en) | 2008-11-19 | 2010-05-27 | Merial Limited | Compositions comprising an aryl pyrazole and/or a formamidine, methods and uses thereof |
| UA108641C2 (uk) | 2010-04-02 | 2015-05-25 | Паразитицидна композиція, яка містить чотири активних агенти, та спосіб її застосування | |
| CA2855954C (en) | 2011-11-17 | 2020-09-01 | Merial Limited | Compositions comprising an aryl pyrazole and a substituted imidazole, methods and uses thereof. |
| TWI579274B (zh) | 2012-04-20 | 2017-04-21 | 龍馬躍公司 | 製備１－芳基－５－烷基吡唑化合物的改良方法 |
| AU2015339096B2 (en) | 2014-10-31 | 2018-08-02 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal composition comprising fipronil |
| WO2019089631A1 (en) * | 2017-10-30 | 2019-05-09 | University Of North Texas Health Science Center At Fort Worth | Deterrents for arthropods and marine organisms |
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| JPS62283961A (ja) * | 1986-05-24 | 1987-12-09 | バイエル・アクチエンゲゼルシヤフト | ５−オキシ（チオ）ビラゾ−ル誘導体 |
| JPH02282366A (ja) * | 1989-03-02 | 1990-11-19 | Rhone Poulenc Agrochim | ３‐シアノ‐５‐アルコキシ‐１‐アリールピラゾール殺虫剤 |
| JPH09169644A (ja) * | 1995-09-29 | 1997-06-30 | Rhone Merieux | ペット寄生虫の治療・予防用組成物 |
| JPH11246555A (ja) * | 1997-10-31 | 1999-09-14 | Sumitomo Chem Co Ltd | フッ素置換ベンゾヘテロ環化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8713768D0 (en) | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
| US5232940A (en) | 1985-12-20 | 1993-08-03 | Hatton Leslie R | Derivatives of N-phenylpyrazoles |
| DE3625686A1 (de) * | 1986-07-30 | 1988-02-04 | Bayer Ag | 4-cyano(nitro)-5-oxy(thio)-pyrazol-derivate |
| CA2004776C (fr) | 1988-12-13 | 2000-04-25 | Claude Wakselman | Procede de preparation de perfluoroalkylthioethers |
| US5079370A (en) | 1989-03-02 | 1992-01-07 | Rhone-Poulenc Ag Company | 1-arylpyrazoles |
| DE4023488A1 (de) * | 1990-07-24 | 1992-01-30 | Bayer Ag | 1-(pyri(mi)dyl-(2)) -5-hydroxy-pyrazol-mikrobizide |
| GB9306184D0 (en) | 1993-03-25 | 1993-05-19 | Zeneca Ltd | Heteroaromatic compounds |
| GB9601128D0 (en) | 1995-08-11 | 1996-03-20 | Pfizer Ltd | Parasiticidal compounds |
| EP0879229B1 (en) | 1996-01-30 | 2002-11-06 | Takeda Chemical Industries, Ltd. | Arylpyrazole insecticides |
| GB9625045D0 (en) | 1996-11-30 | 1997-01-22 | Pfizer Ltd | Parasiticidal compounds |
| DE19650197A1 (de) | 1996-12-04 | 1998-06-10 | Bayer Ag | 3-Thiocarbamoylpyrazol-Derivate |
| TW524667B (en) | 1996-12-05 | 2003-03-21 | Pfizer | Parasiticidal pyrazoles |
| US6350771B1 (en) | 1996-12-24 | 2002-02-26 | Rhone-Poulenc, Inc. | Pesticidal 1-arylpyrazoles |
| CZ294766B6 (cs) | 1996-12-24 | 2005-03-16 | Rhone-Poulenc Agro | 1-Arylpyrazolové sloučeniny, pesticidní prostředky obsahující tyto sloučeniny jako účinné látky a způsob hubení škůdců |
| SK284351B6 (sk) | 1996-12-24 | 2005-02-04 | Rhone-Poulenc Agro | 1-Arylpyrazoly a ich soli, pesticídne prostriedky obsahujúce tieto zlúčeniny ako účinné látky, spôsob prípravy 1-arylpyrazolov a spôsob regulácie škodcov |
| JP2000169453A (ja) * | 1998-09-30 | 2000-06-20 | Mitsubishi Chemicals Corp | １―フェニルピラゾ―ル―３―カルボキサミド誘導体、その中間体およびこれを有効成分とする農薬 |
-
2000
- 2000-12-01 MX MXPA02005511A patent/MXPA02005511A/es active IP Right Grant
- 2000-12-01 CZ CZ20021898A patent/CZ20021898A3/cs unknown
- 2000-12-01 IL IL14985600A patent/IL149856A0/xx active IP Right Grant
- 2000-12-01 AU AU28393/01A patent/AU784798B2/en not_active Expired
- 2000-12-01 HU HU0300357A patent/HUP0300357A3/hu unknown
- 2000-12-01 PL PL00364874A patent/PL364874A1/xx not_active IP Right Cessation
- 2000-12-01 CA CA002393197A patent/CA2393197C/en not_active Expired - Lifetime
- 2000-12-01 KR KR1020027006979A patent/KR100816914B1/ko not_active Expired - Fee Related
- 2000-12-01 BR BR0015945-0A patent/BR0015945A/pt not_active Application Discontinuation
- 2000-12-01 CN CNA2006101356663A patent/CN1939909A/zh active Pending
- 2000-12-01 WO PCT/EP2000/012100 patent/WO2001040195A2/en not_active Ceased
- 2000-12-01 CO CO00091998A patent/CO5261614A1/es not_active Application Discontinuation
- 2000-12-01 ES ES00993256T patent/ES2409630T3/es not_active Expired - Lifetime
- 2000-12-01 EP EP00993256A patent/EP1237873B1/en not_active Expired - Lifetime
- 2000-12-01 MY MYPI20005663A patent/MY129771A/en unknown
- 2000-12-01 CN CN00816524A patent/CN1402713A/zh active Pending
- 2000-12-01 JP JP2001541880A patent/JP2003516941A/ja active Pending
- 2000-12-02 TW TW089125709A patent/TWI290137B/zh not_active IP Right Cessation
- 2000-12-04 AR ARP000106403A patent/AR033504A1/es unknown
- 2000-12-04 US US09/727,684 patent/US6569886B2/en not_active Expired - Lifetime
-
2002
- 2002-05-26 IL IL149856A patent/IL149856A/en unknown
- 2002-05-30 ZA ZA200204336A patent/ZA200204336B/xx unknown
-
2003
- 2003-04-04 US US10/406,491 patent/US6992099B2/en not_active Expired - Lifetime
-
2005
- 2005-09-27 US US11/235,087 patent/US20060020013A1/en not_active Abandoned
-
2006
- 2006-09-29 US US11/529,778 patent/US7468381B2/en not_active Expired - Lifetime
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| JPS62283961A (ja) * | 1986-05-24 | 1987-12-09 | バイエル・アクチエンゲゼルシヤフト | ５−オキシ（チオ）ビラゾ−ル誘導体 |
| JPH02282366A (ja) * | 1989-03-02 | 1990-11-19 | Rhone Poulenc Agrochim | ３‐シアノ‐５‐アルコキシ‐１‐アリールピラゾール殺虫剤 |
| US5047550A (en) * | 1989-03-02 | 1991-09-10 | Rhone-Poulenc Ag Co. | 3-cyano-5-hydroxy-1-arylpyrazoles |
| JPH09169644A (ja) * | 1995-09-29 | 1997-06-30 | Rhone Merieux | ペット寄生虫の治療・予防用組成物 |
| JPH11246555A (ja) * | 1997-10-31 | 1999-09-14 | Sumitomo Chem Co Ltd | フッ素置換ベンゾヘテロ環化合物 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011219420A (ja) * | 2010-04-09 | 2011-11-04 | Otsuka Agritechno Co Ltd | 新規なピラゾール化合物、その製造方法及び有害生物防除剤 |
| JP2014084307A (ja) * | 2012-10-25 | 2014-05-12 | Nagoya Institute Of Technology | 新規トリフロン誘導体及びその製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR100816914B1 (ko) | 2008-03-26 |
| CZ20021898A3 (cs) | 2003-04-16 |
| AU784798B2 (en) | 2006-06-22 |
| EP1237873A2 (en) | 2002-09-11 |
| KR20030016204A (ko) | 2003-02-26 |
| HUP0300357A3 (en) | 2009-01-28 |
| HUP0300357A2 (hu) | 2003-07-28 |
| IL149856A (en) | 2009-02-11 |
| ES2409630T3 (es) | 2013-06-27 |
| CO5261614A1 (es) | 2003-03-31 |
| US20020111352A1 (en) | 2002-08-15 |
| WO2001040195A3 (en) | 2001-11-08 |
| PL364874A1 (en) | 2004-12-27 |
| TWI290137B (en) | 2007-11-21 |
| US20060020013A1 (en) | 2006-01-26 |
| WO2001040195A2 (en) | 2001-06-07 |
| BR0015945A (pt) | 2002-11-12 |
| AR033504A1 (es) | 2003-12-26 |
| MY129771A (en) | 2007-04-30 |
| US7468381B2 (en) | 2008-12-23 |
| IL149856A0 (en) | 2002-11-10 |
| US20070078127A1 (en) | 2007-04-05 |
| CN1939909A (zh) | 2007-04-04 |
| CA2393197A1 (en) | 2001-06-07 |
| EP1237873B1 (en) | 2013-04-03 |
| ZA200204336B (en) | 2003-03-20 |
| US20030176466A1 (en) | 2003-09-18 |
| AU2839301A (en) | 2001-06-12 |
| MXPA02005511A (es) | 2004-09-10 |
| CA2393197C (en) | 2009-03-03 |
| CN1402713A (zh) | 2003-03-12 |
| US6992099B2 (en) | 2006-01-31 |
| US6569886B2 (en) | 2003-05-27 |
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