JP5813658B2 - 殺虫性アリールピロリジン類 - Google Patents
殺虫性アリールピロリジン類 Download PDFInfo
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- JP5813658B2 JP5813658B2 JP2012545342A JP2012545342A JP5813658B2 JP 5813658 B2 JP5813658 B2 JP 5813658B2 JP 2012545342 A JP2012545342 A JP 2012545342A JP 2012545342 A JP2012545342 A JP 2012545342A JP 5813658 B2 JP5813658 B2 JP 5813658B2
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- Prior art keywords
- spp
- methyl
- alkyl
- ethyl
- trifluoromethyl
- Prior art date
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- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- 235000005806 ruta Nutrition 0.000 description 1
- 102000042094 ryanodine receptor (TC 1.A.3.1) family Human genes 0.000 description 1
- 108091052345 ryanodine receptor (TC 1.A.3.1) family Proteins 0.000 description 1
- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 230000011664 signaling Effects 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
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- IYYIUOWKEMQYNV-UHFFFAOYSA-N sodium;ethoxy-oxido-oxophosphanium Chemical compound [Na+].CCO[P+]([O-])=O IYYIUOWKEMQYNV-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940014213 spinosad Drugs 0.000 description 1
- 229930185156 spinosyn Natural products 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
- 239000004544 spot-on Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 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
- AWYOMXWDGWUJHS-UHFFFAOYSA-N tebupirimfos Chemical compound CCOP(=S)(OC(C)C)OC1=CN=C(C(C)(C)C)N=C1 AWYOMXWDGWUJHS-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
- 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
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960002722 terbinafine Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 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
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 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
- 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
- YIBACQHAKISWLZ-UHFFFAOYSA-N thiophene-2-sulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CS1 YIBACQHAKISWLZ-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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 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
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-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
- 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 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
- 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
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 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
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000664 voltage gated sodium channel blocking agent 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
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Epidemiology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catching Or Destruction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Aは、C−X3または窒素であり;好ましくは、Aは、C−X3であり;より好ましくは、Aは、C−H、C−F、C−Cl、C−Br、C−IまたはC−CF3であり;最も好ましくは、Aは、C−H、C−ClまたはCCF3であり;
X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲン、C1−4ハロアルキル、C1−4ハロアルコキシ、C1−4ハロアルキルチオ、C1−4ハロアルキルスルフィニルおよびC1−4ハロアルキルスルホニルであり;好ましくは、X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲンまたはC1−4ハロアルキルであり;より好ましくは、X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲンまたはCF3であり;
R1は、C1−4ハロアルキルであり;好ましくは、R1は、トリフルオロメチルであり;
R2は、C1−4アルキル、C1−4ハロアルキル、C3−6シクロアルキルまたはシアノであり;好ましくは、R2は、メチル、エチルまたはシクロプロピルであり;より好ましくは、R2は、メチルであり;
R3は、水素、C1−4アルキルまたはC1−4ハロアルキルであり;好ましくは、R3は、水素であり;
R4は、C1−4アルキル、C1−4ハロアルキル、C3−6シクロアルキル、C3−6シクロアルキル−C1−4アルキル;C3−6ハロシクロアルキル、C1−4アルコキシ、C1−4アルコキシ−C1−4アルキル、C1−4ハロアルコキシ−C1−4アルキル、C1−4アルキルチオ−C1−4アルキル、C1−4アルキルスルフィニル−C1−4アルキル、C1−4アルキルスルホニル−C1−4アルキル、C1−4ハロアルキルチオ−C1−4アルキル、C1−4ハロアルキルスルフィニル−C1−4アルキル、C1−4ハロアルキルスルホニル−C1−4アルキルまたはC1−4アルキルアミノ、ハロゲン置換フェニルであり;好ましくは、R4は、メチル、エチル、シクロプロピル、シクロプロピルメチル、2,2,2−トリフルオロエチル、2−メトキシエチル、メチルチオメチル、メチルスルフィニルメチル、メチルスルホニルメチルまたは2,4,6−トリフルオロフェニルであり;より好ましくは、R4は、メチル、エチルまたはシクロプロピルであり;
Gは、OまたはSであり;好ましくは、GはOである。)
のアリールピロリジン化合物に関する。
本発明によるアリールピロリジン化合物の調製のための方法(a)は、
式(II)
Aは、C−X3または窒素であり;好ましくは、AはC−X3であり;より好ましくは、Aは、C−H、C−F、C−Cl、C−Br、C−IまたはC−CF3であり;最も好ましくは、Aは、C−H、C−ClまたはCCF3であり;
X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲン、C1−4ハロアルキル、C1−4ハロアルコキシ、C1−4ハロアルキルチオ、C1−4ハロアルキルスルフィニルおよびC1−4ハロアルキルスルホニルであり;好ましくは、X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲンまたはC1−4ハロアルキルであり;より好ましくは、X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲンまたはCF3であり;
R1はC1−4ハロアルキルであり;好ましくは、R1はトリフルオロメチルであり;
R2は、C1−4アルキル、C1−4ハロアルキル、C3−6シクロアルキルまたはシアノであり;好ましくは、R2は、メチル、エチルまたはシクロプロピルを表し;より好ましくは、R2は、メチルであり;
R3は、水素、C1−4アルキルまたはC1−4ハロアルキルであり;好ましくは、R3は水素であり;
R4は、C1−4アルキル、C1−4ハロアルキル、C3−6シクロアルキル、C3−6シクロアルキル−C1−4アルキル;C3−6ハロシクロアルキル、C1−4アルコキシ、C1−4アルコキシ−C1−4アルキル、C1−4ハロアルコキシ−C1−4アルキル、C1−4アルキルチオ−C1−4アルキル、C1−4アルキルスルフィニル−C1−4アルキル、C1−4アルキルスルホニル−C1−4アルキル、C1−4ハロアルキルチオ−C1−4アルキル、C1−4ハロアルキルスルフィニル−C1−4アルキル、C1−4ハロアルキルスルホニル−C1−4アルキルまたはC1−4アルキルアミノ、ハロゲン置換フェニルであり;好ましくは、R4は、メチル、エチル、シクロプロピル、シクロプロピルメチル、2,2,2−トリフルオロエチル、2−メトキシエチル、メチルチオメチル、メチルスルフィニルメチル、メチルスルホニルメチルまたは2,4,6−トリフルオロフェニルであり;より好ましくは、R4は、メチル、エチルまたはシクロプロピルであり;
Gは、OまたはSであり;好ましくは、GはOであり;
L1は、ハロゲンまたはC1−4ハロアルキルスルホニルオキシである。
N−[1−(4−ブロモフェニル)エチル]アセトアミド、N−[(1S)−1−(4−ブロモフェニル)エチル]アセトアミド、N−[(1R)−1−(4−ブロモフェニル)エチル]アセトアミド、N−[1−(4−ブロモフェニル)エチル]プロパンアミド、N−[(1S)−1−(4−ブロモフェニル)エチル]プロパンアミド、N−[(1R)−1−(4−ブロモフェニル)エチル]プロパンアミド、N−[1−(4−ブロモフェニル)エチル]シクロプロパンカルボキサミド、N−[(1S)−1−(4−ブロモフェニル)エチル]シクロプロパン−カルボキサミド、N−[(1R)−1−(4−ブロモフェニル)エチル]シクロプロパンカルボキサミド、N−[1−(4−ブロモフェニル)エチル]シクロプロパンアセトアミド、N−[(1S)−1−(4−ブロモフェニル)エチル]シクロプロパン−アセトアミド、N−[1−(4−ブロモフェニル)エチル]−3−メトキシプロパンアミド、N−[(1S)−1−(4−ブロモフェニル)エチル]−3−メトキシプロパンアミド、N−[1−(4−ブロモフェニル)エチル]−2,4,6−トリフルオロベンズアミドおよびN−[(1S)−1−(4−ブロモフェニル)エチル]−2,4,6−トリフルオロベンズアミド
が挙げられる。
2,6−ビス(トリフルオロメチル)−4−[3−(トリフルオロメチル)ピロリジン−3−イル]ピリジン、3−(3−クロロフェニル)−3−(トリフルオロメチル)ピロリジン、3−(3−ブロモフェニル)−3−(トリフルオロメチル)ピロリジン、3−(トリフルオロメチル)−3−[3−(トリフルオロメチル)フェニル]ピロリジン、3−(3,5−ジクロロフェニル)−3−(トリフルオロメチル)ピロリジン、3−(3,5−ジブロモフェニル)−3−(トリフルオロメチル)ピロリジン、3−[3−クロロ−5−(トリフルオロメチル)フェニル]−3−(トリフルオロメチル)ピロリジン、3−[3,5−ビス(トリフルオロメチル)フェニル]−3−(トリフルオロメチル)ピロリジン、3−(3,4,5−トリクロロフェニル)−3−(トリフルオロメチル)ピロリジン、3−[3,4−ジクロロ−5−(トリフルオロメチル)フェニル]−3−(トリフルオロメチル)ピロリジンおよび2,6−ビス(トリフルオロメチル)−4−[3−(トリフルオロメチル)ピロリジン−3−イル]ピリジン
が挙げられる。
(i)式(VI)
(ii)式(VII)の化合物からベンジル基を除去すること(脱ベンジル化)によって調製することができ、ここで、式(VI)および式(VII)において、
Aは、C−X3または窒素であり;好ましくは、AはC−X3であり;より好ましくは、Aは、C−H、C−F、C−Cl、C−Br、C−IまたはC−CF3であり;最も好ましくは、Aは、C−H、C−ClまたはCCF3であり;
X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲン、C1−4ハロアルキル、C1−4ハロアルコキシ、C1−4ハロアルキルチオ、C1−4ハロアルキルスルフィニルおよびC1−4ハロアルキルスルホニルであり;好ましくは、X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲンまたはC1−4ハロアルキルであり;より好ましくは、X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲンまたはCF3であり;
R1は、C1−4ハロアルキルであり;好ましくは、R1はトリフルオロメチルである。
Aは、C−X3または窒素であり;好ましくは、AはC−X3であり;より好ましくは、Aは、C−H、C−F、C−Cl、C−Br、C−IまたはC−CF3であり;最も好ましくは、Aは、C−H、C−ClまたはCCF3であり;
X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲン、C1−4ハロアルキル、C1−4ハロアルコキシ、C1−4ハロアルキルチオ、C1−4ハロアルキルスルフィニルおよびC1−4ハロアルキルスルホニルであり;好ましくは、X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲンまたはC1−4ハロアルキルであり;より好ましくは、X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲンまたはCF3であり;
R1は、C1−4ハロアルキルであり;好ましくは、R1はトリフルオロメチルであり;
R2は、C1−4アルキル、C1−4ハロアルキル、C3−6シクロアルキルまたはシアノであり;好ましくは、R2は、メチル、エチルまたはシクロプロピルを表し;より好ましくは、R2はメチルであり;
R4は、C1−4アルキル、C1−4ハロアルキル、C3−6シクロアルキル、C3−6シクロアルキル−C1−4アルキル;C3−6ハロシクロアルキル、C1−4アルコキシ、C1−4アルコキシ−C1−4アルキル、C1−4ハロアルコキシ−C1−4アルキル、C1−4アルキルチオ−C1−4アルキル、C1−4アルキルスルフィニル−C1−4アルキル、C1−4アルキルスルホニル−C1−4アルキル、C1−4ハロアルキルチオ−C1−4アルキル、C1−4ハロアルキルスルフィニル−C1−4アルキル、C1−4ハロアルキルスルホニル−C1−4アルキルまたはC1−4アルキルアミノ、ハロゲン置換フェニルであり;好ましくは、R4は、メチル、エチル、シクロプロピル、シクロプロピルメチル、2,2,2−トリフルオロエチル、2−メトキシエチル、メチルチオメチル、メチルスルフィニルメチル、メチルスルホニルメチルまたは2,4,6−トリフルオロフェニルであり;より好ましくは、R4は、メチル、エチルまたはシクロプロピルであり;
Gは、OまたはSであり;好ましくは、GはOであり、
L2は、ヒドロキシ、フッ素、塩素、臭素、C1−4アルキル−カルボニルオキシ、C1−4アルコキシ−カルボニルオキシ、C1−4アルキル−スルホニルオキシ、C1−4ハロアルキル−スルホニルオキシ、アリールスルホニルオキシまたはアゾリルである。
(1)アセチルコリンエステラーゼ(AChE)阻害剤、例えば、カルバメート、例えば、アラニカルブ、アルジカルブ、ベンジオカルブ、ベンフラカルブ、ブトカルボキシム、ブトキシカルボキシム、カルバリル、カルボフラン、カルボスルファン、エチオフェンカルブ、フェノブカルブ、ホルメタネート、フラチオカルブ、イソプロカルブ、メチオカルブ、メソミル、メトルカルブ、オキサミル、ピリミカルブ、プロポクスル、チオジカルブ、チオファノックス、トリアザメート、トリメタカルブ、XMCおよびキシリルカルブ;または有機リン酸エステル系、例えば、アセフェート、アザメチホス、アジンホス(−メチル,−エチル)、カズサホス、クロルエトキシホス、クロルフェンビンホス、クロルフェンビンホス、クロルメホス、クロルピリホス(−メチル)、クマホス、シアノホス、ジメトン−S−メチル、ダイアジノン、ジクロルボス/DDVP、ジクロトホス、ジメトエート、ジメチルビンホス、ダイスルホトン、EPN、エチオン、エトプロホス、ファムフール、フェナミホス、フェニトロチオン、フェンチオン、ホスチアゼート、ヘプテノホス、イソフェンホス、イソプロピルO−(メトキシアミノチオ−ホスホリル)サリチレート、イソキサチオン、マラチオン、メカルバム、メタミドホス、メチダチオン、メビンホス、モノクロトホス、ナレド、オメトエート、オキシデメトン−メチル、パラチオン(−メチル)、フェントエート、ホレート、ホサロン、ホスメット、ホスファミドン、ホキシム、ピリミホス(−メチル)、プロフェノホス、プロペタムホス、プロチオホス、ピラクロホス、ピリダフェンチオン、キナルホス、スルホテップ、テブピリムホス、テメホス、テルブホス、テトラクロルビンホス、チオメトン、トリアゾホス、トリクロルホンおよびバミドチオン。
4−{[(6−ブロムピリド−3−イル)メチル](2−フルオルエチル)アミノ}フラン−2(5H)−オン(WO2007/115644から既知)、4−{[(6−フルオルピリド−3−イル)メチル](2,2−ジフルオルエチル)アミノ}フラン−2(5H)−オン(WO2007/115644から既知)、4−{[(2−クロル−1,3−チアゾール−5−イル)メチル](2−フルオルエチル)アミノ}フラン−2(5H)−オン(WO2007/115644から既知)、4−{[(6−クロル−ピリド−3−イル)メチル](2−フルオルエチル)アミノ}フラン−2(5H)−オン(WO2007/115644から既知)、4−{[(6−クロルピリド−3−イル)メチル](2,2−ジフルオルエチル)アミノ}フラン−2(5H)−オン(WO2007/115644から既知)、4−{[(6−クロル−5−フルオルピリド−3−イル)メチル](メチル)アミノ}フラン−2(5H)−オン(WO2007/115643から既知)、4−{[(5,6−ジクロルピリド−3−イル)メチル](2−フルオルエチル)アミノ}フラン−2(5H)−オン(WO2007/115646から既知)、4−{[(6−クロル−5−フルオルピリド−3−イル)メチル](シクロプロピル)アミノ}フラン−2(5H)−オン(WO2007/115643から既知)、4−{[(6−クロルピリド−3−イル)メチル](シクロプロピル)アミノ}フラン−2(5H)−オン(EP−A−0539588から既知)、4−{[(6−クロルピリド−3−イル)メチル](メチル)アミノ}フラン−2(5H)−オン(EP−A−0539588から既知)、[(6−クロルピリジン−3−イル)メチル](メチル)オキシド−λ4−スルファニリデンシアナミド(WO2007/149134から既知)、[1−(6−クロルピリジン−3−イル)エチル](メチル)オキシド−λ4−スルファニリデンシアナミド(WO2007/149134から既知)ならびにそのジアステレオマー(A)および(B)
(1)エルゴステロール生合成の阻害剤、例えば、アルジモルフ、アザコナゾール、ビテルタノール、ブロムコナゾール、シプロコナゾール、ジクロブトラゾール、ジフェノコナゾール、ジニコナゾール、ジニコナゾール−M、ドデモルフ、酢酸ドデモルフ、エポキシコナゾール、エタコナゾール、フェナリモール、フェンブコナゾール、フェンヘキサミド、フェンプロピジン、フェンプロピモルフ、フルキンコナゾール、フルルプリミドール、フルシラゾール、フルトリアホール、フルコナゾール、フルコナゾール−シス、ヘキサコナゾール、イマザリル、硫酸イマザリル、イミベンコナゾール、イプコナゾール、メトコナゾール、ミクロブタニル、ナフチフィン、ヌアリモール、オキシポコナゾール、パクロブトラゾール、ペフラゾエート、ペンコナゾール、ピペラリン、プロクロラズ、プロピコナゾール、プロチオコナゾール、ピリブチカルブ、ピリフェノックス、キンコナゾール、シメコナゾール、スピロキサミン、テブコナゾール、テルビナフィン、テトラコナゾール、トリアジメホン、トリアジメノール、トリデモルフ、トリフルミゾール、トリホリン、トリチコナゾール、ウニコナゾール、ウニコナゾール−P、ビニコナゾール、ボリコナゾール、1−(4−クロロフェニル)−2−(1H−1,2,4−トリアゾール−1−イル)シクロヘプタノール、メチル1−(2,2−ジメチル−2,3−ジヒドロ−1H−インデン−1−イル)−1H−イミダゾール−5−カルボキシレート、N’−{5−(ジフルオロメチル)−2−メチル−4−[3−(トリメチル−シリル)プロポキシ]フェニル}−N−エチル−N−メチルイミドホルムアミド、N−エチル−N−メチル−N’−{2−メチル−5−(トリフルオロメチル)−4−[3−(トリメチルシリル)プロポキシ]フェニル}イミドホルムアミドおよびO−[1−(4−メトキシ−フェノキシ)−3,3−ジメチルブタン−2−イル]1H−イミダゾール−1−カルボチオエート。
目:節足動物門(Arthropoda):アラクニダ(Arachnida)綱から、例えば、アカルス属種(Acarus spp.)、アケリア・シェルドニ(Aceria sheldoni)、アクロプス属種(Aculops spp.)、アクルス属種(Aculus spp.)、アムブリュオンマ属種(Amblyomma spp.)、アムピテトラニュクス・ウィエンネンシス(Amphitetranychus viennensis)、アルガス属種(Argas spp.)、ボオピルス属種(Boophilus spp.)、ブレウィ−パルプス属種(Brevi−palpus spp.)、ブリュオビア・プラエティオサ(Bryobia praetiosa)、ケントルロイデス属種(Centruroides spp.)、コリオプテス属種(Chorioptes spp.)、デルマニュッスス・ガッリナエ(Dermanyssus gallinae)、デルマトパゴイデス・プテロニュッシウス(Dermatophagoides pteronyssius)、デルマトパゴイデス・ファリナエ(Dermatophagoides farinae)、デルマケントル属種(Dermacentor spp.)、エオテトラニュクス属種(Eotetranychus spp.)、エピトリメルス・ピュリ(Epitrimerus pyri)、エウテトラニュクス属種(Eutetranychus spp.)、エリオピュエス属種(Eriophyes spp.)、ハロティデウス・デストルクトル(Halotydeus destructor)、ヘミタルソネムス属種(Hemitarsonemus spp.)、フュアロンマ属種(Hyalomma spp.)、イクソデス属種(Ixodes spp.)、ラトロデクトゥス属種(Latrodectus spp.)、ロクソスケレス属種(Loxosceles spp.)、メタテトラニュクス属種(Metatetranychus spp.)、ヌペルサ属種(Nuphersa spp.)、オリゴニュクス属種(Oligonychus spp.)、オルニトドルス属種(Ornithodorus spp.)、オルニトニュッスス属種(Ornithonyssus spp.)、パノニュクス属種(Panonychus spp.)、ピュッロコプトルタ・オレイウォラ(Phyllocoptruta oleivora)、ポリュパゴタルソネムス・ラトゥス(Polyphagotarsonemus latus)、プソロプテス属種(Psoroptes spp.)、リピケパルス属種(Rhipicephalus spp.)、リゾグリュプス属種(Rhizoglyphus spp.)、サルコプテス属種(Sarcoptes spp.)、スコルピオ・マウルス(Scorpio maurus)、ステノタルソネムス属種(Stenotarsonemus spp.)、タルソネムス属種(Tarsonemus spp.)、テトラニュクス属種(Tetranychus spp.)、ワエヨウィス属種(Vaejovis spp.)、ワサテス・リュコペルシキ(Vasates lycopersici)、
シラミ目(Anoplura)(プティラプテラ(Phthiraptera))の目から、例えば、ダマリニア属種(Damalinia spp.)、ハエマトピヌス属種(Haematopinus spp.)、リノグナトゥス属種(Linognathus spp.)、ペディクルス属種(Pediculus spp.)、プティルス・プビス(Ptirus pubis)、トリコデクテス属種(Trichodectes spp.)。
異翅目(Heteroptera)の目から、例えば、アナサ・トリスティス(Anasa tristis)、アンテスティオプシス属種(Antestiopsis spp.)、ボイセア属種(Boisea spp.)、ブリッスス属種(Blissus spp.)、カロコリス属種(Calocoris spp.)、カムピュロンマ・リウィダ(Campylomma livida)、カウェレリウス属種(Cavelerius spp.)、キメクス属種(Cimex spp.)、キメクス・レクトゥラリウス(Cimex lectularius)、キメクス・ヘミプテルス(Cimex hemipterus)、コッラリア属種(Collaria spp.)、クレオンティアデス・ディルトゥス(Creontiades dilutus)、ダシュヌス・ピペリス(Dasynus piperis)、ディケロプス・フルカトゥス(Dichelops furcatus)、ディコノコリス・ヘウェッティ(Diconocoris hewetti)、ドュスデルクス属種(Dysdercus spp.)、エウスキストゥス属種(Euschistus spp.)、エウリュガステル属種(Eurygaster spp.)、ヘリオペルティス属種(Heliopeltis spp.)、ホルキアス・ノビレッルス(Horcias nobilellus)、レプトコリサ属種(Leptocorisa spp.)、レプトグロッスス・ピュッロプス(Leptoglossus phyllopus)、リュグス属種(Lygus spp.)、マクロペス・エクスカワトゥス(Macropes excavatus)、ミリダエ(Miridae)、モナロニオン・アトラトゥム(Monalonion atratum)、ネザラ属種(Nezara spp.)、オエバルス属種(Oebalus spp.)、ペントミダエ(Pentomidae)、ピエスマ・クワドラタ(Piesma quadrata)、ピエゾドルス属種(Piezodorus spp.)、プサッルス属種(Psallus spp.)、プセウダキュスタ・ペルセア(Pseudacysta persea)、ロドニウス属種(Rhodnius spp.)、サルベルゲッラ・シングラリス(Sahlbergella singularis)、スカプトコリス・カスタネア(Scaptocoris castanea)、スコティノポラ属種(Scotinophora spp.)、ステパニティス・ナシ(Stephanitis nashi)、ティブラカ属種(Tibraca spp.)、トリアトマ属種(Triatoma spp.)。
さらに、ダニ類として、例えば、テトラニュクス・キンナバリヌス(Tetranychus cinnabarinus)、テトラニュクス・ウルティカエ(Tetranychus urticae)、パノニュクス・キトリ(Panonychus citri)、アクロプス・ペレカッシ(Aculops pelekassi)、タルソネムス属種(Tarsonemus spp.)がある。
アノプルリダ目(Anoplurida)の目から、例えば、ハエマトピヌス属種(Haematopinus spp.)、リノグナトゥス属種(Linognathus spp.)、ペディクルス属種(Pediculus spp.)、プティルス属種(Phtirus spp.)、ソレノポテス属種(Solenopotes spp.);特定の例は、リノグナトゥス・セトスス(Linognathus setosus)、リノグナトゥス・ウィトゥリ(Linognathus vituli)、リノグナトゥス・オウィッルス(Linognathus ovillus)、リノグナトゥス・オウィフォルミス(Linognathus oviformis)、リノグナトゥス・ペダリス(Linognathus pedalis)、リノグナトゥス・ステノプシス(Linognathus stenopsis)、ハエマトピヌス・アシニ・マクロケパルス(Haematopinus asini macrocephalus)、ハエマトピヌス・エルリュステルヌス(Haematopinus erurysternus)、ハエマトピヌス・スイス(Haematopinus suis)、ペディクルス・フマヌス・カピティス(Pediculus humanus capitis)、ペディクルス・フマヌス・コルポリス(Pediculus humanus corporis)、ピュッロエラ・ワスタトリクス(Phylloera vastatrix)、プティルス・プビス(Phthirus pubis)、ソレノポテス・カピッラトゥス(Solenopotes capillatus)である;
マッロパギダ目(Mallophagida)の目ならびにアムブリュケリナ亜目(Amblycerina)およびイスクノケリナ亜目(Ischnocerina)の亜目から、例えば、トリメノポン属種(Trimenopon spp.)、メノポン属種(Menopon spp.)、トリノトン属種(Trinoton spp.)、ボウィコラ属種(Bovicola spp.)、ウェルネクキエッラ属種(Werneckiella spp.)、レピケントロン属種(Lepikentron spp.)、ダマリナ属種(Damalina spp.)、トリコデクテス属種(Trichodectes spp.)、フェリコラ属種(Felicola spp.);特定の例は、ボウィコラ・ボウィス(Bovicola vovis)、ボウィコラ・オウィス(Bovicol ovis)、ボウィコラ・リムバタ(Bovicola limbata)、ダマリナ・ボウィス(Damalina bovis)、トリコデクテス・カニス(Trichodectes canis)、フェリコラ・スブロストラトゥス(Felicola subrostratus)、ボウィコラ・カプラエ(Bovicola caprae)、レピケントロン・オウィス(Lepikentron ovis)、ヴェルネクキエッラ・エクィ(Werneckiella equi)である;
双翅目(Diptera)の目ならびにネマトケリナ亜目(Nematocerina)およびブラキュケリナ亜目(Brachycerina)の亜目から、例えば、アエデス属種(Aedes spp.)、アノペレス属種(Anopheles spp.)、クレクス属種(Culex spp.)、シムリウム属種(Simulium spp.)、エウシムリウム属種(Eusimulium spp.)、プレボトムス属種(Phlebotomus spp.)、ルトゾミュイア属種(Lutzomyia spp.)、クリコイデス属種(Culicoides spp.)、クリュソプス属種(Chrysops spp.)、オダグミア属種(Odagmia spp.)、ヴィルヘルミア属種(Wilhelmia spp.)、フュボミトラ属種(Hybomitra spp.)、アテュロトゥス属種(Atylotus spp.)、タバヌス属種(Tabanus spp.)、ハエマトポタ属種(Haematopota spp.)、ピリポミュイア属種(Philipomyia spp.)、ブラウラ属種(Braula spp.)、ムスカ属種(Musca spp.)、フュドロタエア属種(Hydrotaea spp.)、ストモクシス属種(Stomoxys spp.)、ハエマトビア属種(Haematobia spp.)、モレッリア属種(Morellia spp.)、ファンニア属種(Fannia spp.)、グロッシナ属種(Glossina spp.)、カッリポラ属種(Calliphora spp.)、ルキリア属種(Lucilia spp.)、クリュソミュイア属種(Chrysomyia spp.)、ヴォルファルティア属種(Wohlfahrtia spp.)、サルコパガ属種(Sarcophaga spp.)、オエストルス属種(Oestrus spp.)、フュポデルマ属種(Hypoderma spp.)、ガステロピルス属種(Gasterophilus spp.)、ヒッポボスカ属種(Hippobosca spp.)、リポプテナ属種(Lipoptena spp.)、メロパグス属種(Melophagus spp.)、リノエストルス属種(Rhinoestrus spp.)、ティプラ属種(Tipula spp.);特定の例は、アエデス・アエギュプティ(Aedes aegypti)、アエデス・アルボピクトゥス(Aedes albopictus)、アエデス・タエニオリュンクス(Aedes taeniorhynchus)、アノペレス・ガムビアエ(Anopheles gambiae)、アノペレス・マクリペンニス(Anopheles maculipennis)、カッリポラ・エリュトロケパラ(Calliphora erythrocephala)、クリュソゾナ・プルウィアリス(Chrysozona pluvialis)、クレクス・クウィンクウェファスキアトゥス(Culex quinquefasciatus)、クレクス・ピピエンス(Culex pipiens)、クレクス・タルサリス(Culex tarsalis)、ファンニア・カニクラリス(Fannia canicularis)、サルコパガ・カルナリア(Sarcophaga carnaria)、ストモクシス・カルキトランス(Stomoxys calcitrans)、ティプラ・パルドサ(Tipula paludosa)、ルキリア・クプリナ(Lucilia cuprina)、ルキリア・セリカタ(Lucilia sericata)、シムリウム・レプタンス(Simulium reptans)、プレボトムス・パパタシ(Phlebotomus papatasi)、プレボトムス・ロンギパルピス(Phlebotomus longipalpis)、オダグミア・オルナタ(Odagmia ornata)、ヴィルヘリマ・エクィナ(Wilhelmia equina)、ボオプトラ・エリュトロケパラ(Boophthora erythrocephala)、タバヌス・ブロミウス(Tabanus bromius)、タバヌス・スポドプテルス(Tabanus spodopterus)、タバヌス・アトラトゥス(Tabanus atratus)、タバヌス・スデティクス(Tabanus sudeticus)、フュボミトラ・シウレア(Hybomitra siurea)、クリュソプス・カエクティエンス(Chrysops caecutiens)、クリュソプス・レリクトゥス(Chrysops relictus)、ハエマトポタ・プルウィアリス(Haematopota pluvialis)、ハエマトポタ・イタリカ(Haematopota italica)、ムスカ・アウトゥマリス(Musca autumalis)、ムスカ・ドメスティカ(Musca domestica)、ハエマトビア・イッリタンス・イッリタンス(Haematobia irritans irritans)、ハエマトビア・イッリタンス・エクシグア(Haematobia irritans exigua)、ハエマトビア・スティムランス(Haematobia stimulans)、フュドロタエア・イッリタンス(Hydrotaea irritans)、フュドロタエア・アルビプンクタ(Hydrotaea albipuncta)、クリュソミュア・クロロピュガ(Chrysomya chloropyga)、クリュソムヤ・ベッジアナ(Chrysomya bezziana)、オエストルス・オウィス(Oestrus ovis)、フュポデルマ・ボウィス(Hypoderma bovis)、フュポデルマ・リネアトゥム(Hypoderma lineatum)、プルゼワルスキアナ・シレヌス(Przhevalskiana silenus)、デルマトビア・ホミニス(Dermatobia hominis)、メロパグス・オウィヌス(Melophagus ovinus)、リポプテナ・カプレオリ(Lipoptena capreoli)、リポプテナ・ケルウィ(Lipoptena cervi)、ヒッポボスカ・ウァリエガタ(Hippobosca variegata)、ヒッポボスカ・エクィナ(Hippobosca equina)、ガステロピルス・インテスティナリス(Gasterophilus intestinalis)、ガステロピルス・ハエモッロイダリス(Gasterophilus haemorroidalis)、ガステロピルス・イネルミス(Gasterophilus inermis)、ガステロピルス・ナサリス(Gasterophilus nasalis)、ガステロピルス・ニグリコルニス(Gasterophilus nigricornis)、ガステロピルス・ペコルム(Gasterophilus pecorum)、ブラウラ・コエカ(Braula coeca)である;
シポナプテリダ目(Siphonapterida)の目から、例えば、プレクス属種(Pulex spp.)、クテノケパリデス属種(Ctenocephalides spp.)、トゥンガ属種(Tunga spp.)、クセノプシュッラ属種(Xenopsylla spp.)、ケラトピュッルス属種(Ceratophyllus spp.);特定の例は、クテノケパリデス・カニス(Ctenocephalides canis)、クテノケパリデス・フェリス(Ctenocephalides felis)、プレクス・イッリタンス(Pulex irritans)、トゥンガ・ペネトランス(Tunga penetrans)、クセノプシュッラ・ケオピス(Xenopsylla cheopis)である;
ヘテロプテリダ目(Heteropterida)の目から、例えば、キメクス属種(Cimex spp.)、トリアトマ属種(Triatoma spp.)、ロドニウス属種(Rhodnius spp.)、パンストロンギュルス属種(Panstrongylus spp.)。
アカリ亜綱(Acari)(ダニ目(Acarina))の亜綱ならびにメタ−(Meta−)およびメソスティグマタ目(Mesostigmata)の目から、例えば、アルガス属種(Argas spp.)、オミトドルス属種(Omithodorus spp.)、オトビウス属種(Otobius spp.)、イクソデス属種(Ixodes spp.)、アムブリュオンマ属種(Amblyomma spp.)、リピケパルス(ボオピルス)属種(Rhipicephalus(Boophilus) spp.)、デルマケントル属種(Dermacentor spp.)、ハエモピュサリス属種(Haemophysalis spp.)、フュアロンマ属種(Hyalomma spp.)、デルマニュッスス属種(Dermanyssus spp.)、リピケパルス属種(Rhipicephalus spp.)(多宿主マダニ類の原属)、オルニトニュッスス属種(Ornithonyssus ssp.)、プネウモニュッスス属種(Pneumonyssus spp.)、ライッリエティア属種(Raillietia spp.)、プネウモニュッスス属種(Pneumonyssus spp.)、ステルノストマ属種(Sternostoma spp.)、ワッロア属種(Varroa spp.)、アカラピス属種(Acarapis spp.);特定の例は、アルガス・ペルシクス(Argas persicus)、アルガス・レフレクスス(Argas reflexus)、モミトドルス・モウバタ(Omithodorus moubata)、オトビウス・メグニニ(Otobius megnini)、リピケパルス(ボオピルス)・ミクロプルス(Rhipicephalus(Boophilus)microplus)、リピケパルス(ボオピルス)・デコロラトゥス(Rhipicephalus(Boophilus)decoloratus)、リピケパルス(ボオピルス)・アッヌラトゥス(Rhipicephalus(Boophilus)annulatus)、リピケパルス(ボオピルス)・カルケラトゥス(Rhipicephalus(Boophilus)calceratus)、フュアロンマ・アナトリクム(Hyalomma anatolicum)、フュロンマ・アエギュプティクム(Hylomma aegypticum)、フュアロンマ・マルギナトゥム(Hyalomma marginatum)、フュラロンマ・トランシエンス(Hyalomma transiens)、リピケパルス・エウェルトシ(Rhipicephalus evertsi)、イクソデス・リキヌス(Ixodes ricinus)、イクソデス・ヘキサゴヌス(Ixodes hexagonus)、イクソデス・カニスガ(Ixodes canisuga)、イクソデス・ピロスス(Ixodes pilosus)、イクソデス・ルビクンドゥス(Ixodes rubicundus)、イクソデス・スカプラリス(Ixodes scapularis)、イクソデス・ホロキュクルス(Ixodes holocyclus)、ハエマピュサリス・コンキンナ(Haemaphysais concinna)、ハエマピュサリス・プンクタタ(Haemaphysalis punctata)、ハエマピュサリス・キンナバリナ(Haemaphysalis cinnabarina)、ハエマピュサリス・オトピラ(Haemaphysalis otophila)、ハエマピュサリス・レアキ(Haemaphysalis leachi)、ハエマピュサリス・ロンギコルニ(Haemaphysalis longicorni)、デルマケントル・マルギナトゥス(Dermacentor marginatus)、デルマケントル・レティクラトゥス(Dermacentor reticulatus)、デルマケントル・ピクトゥス(Dermacentor pictus)、デルマケントル・アルビピクトゥス(Demacentor albipictus)、デルマケントル・アンデルソニ(Dermacentor andersoni)、デルマケントル・ワリアビリス(Dermacentor variabilis)、フュアロンマ・マウリタニクム(Hyalomma mauritanicum)、リピケパルス・サングイネウス(Rhipicephalus sanguineus)、リピケパルス・ブルサ(Rhipicephalus bursa)、リピケパルス・アッペンディクラトゥス(Rhipicephalus appendiculatus)、リピケパルス・カペンシス(Rhipicephalus capensis)、リピケパルス・トゥラニクス(Rhipicephalus turanicus)、リピケパルス・ザムベジエンシス(Rhipicephalus zambeziensis)、アムブリュオンマ・アメリカヌム(Amblyomma americanum)、アムブリュオンマ・ワリエガトゥム(Amblyomma variegatum)、アムブリュオンマ・マクラトゥム(Amblyomma maculatum)、アムブリュオンマ・ヘブラエウム(Amblyomma hebraeum)、アムブリュオンマ・カイェンネンセ(Amblyomma cajennense)、デルマニュッスス・ガッリナエ(Dermanyssus gallinae)、オルニトニュッスス・ブルサ(Ornithonyssus bursa)、オルニトニュッスス・シュルウィアルム(Ornithonyssus sylviarum)、ワッロア・ヤコブソニ(Varroa jacobsoni)である;
アクティネディダ目(Actinedida)(プロスティグマタ(Prostigmata))およびアカリディダ目(Acaridida)(アスティグマタ(Astigmata))の目から、例えば、アカラピス属種(Acarapis spp.)、ケユレティエッラ属種(Cheyletiella spp.)、オミトケユレティア属種(Omithocheyletia spp.)、ミュオビア属種(Myobia spp.)、プソレルガテス属種(Psorergates spp.)、デモデクス属種(Demodex spp.)、トロムビクラ属種(Trombicula spp.)、リストロポルス属種(Listrophorus spp.)、アカルス属種(Acarus spp.)、テュロパグス属種(Tyrophagus spp.)、カログリュプス属種(Caloglyphus spp.)、フュポデクテス属種(Hypodectes spp.)、プテロリクス属種(Pterolichus spp.)、プソロプテス属種(Psoroptes spp.)、コリオプテス属種(Chorioptes spp.)、オトデクテス属種(Otodectes spp.)、サルコプテス属種(Sarcoptes spp.)、ノトエドレス属種(Notoedres spp.)、クネミドコプテス属種(Knemidocoptes spp.)、キュトディテス属種(Cytodites spp.)、ラミノシオプテス属種(Laminosioptes spp.);特定の例は、ケユレティエッラ・ヤスグリ(Cheyletiella yasuguri)、ケユレチエッラ・ブラケイ(Cheyletiella blakei)、デモデクス・カニス(Demodex canis)、デモデクス・ボウィス(Demodex bovis)、デモデクス・オウィス(Demodex ovis)、デモクス・カプラエ(Demodex caprae)、デモデクス・エクィ(Demodex equi)、デモデクス・カバッリ(Demodex caballi)、デモデクス・スイス(Demodex suis)、ネオトロムビクラ・アウトゥムナリス(Neotrombicula autumnalis)、ネオトロムビクラ・デサレリ(Neotrombicula desaleri)、ネオスコンガスティア・クセロテルモビア(Neoschongastia xerothermobia)、トロムビクラ・アカムシ(Trombicula akamushi)、オトデクテス・キュノティス(Otodectes cynotis)、ノトエドレス・カティ(Notoedres cati)、サルコプティス・カニス(Sarcoptis canis)、サルコプテス・ボウィス(Sarucoptes bovis)、サルコプテス・オウィス(Sarcoptes ovis)、サルコプテス・ルピカプラエ(Sarcoptes rupicaprae)(=S.カプラエ(S.caprae))、サルコプテス・エクィ(Sarcoptes equi)、サルコプテス・スイス(Sarcoptes suis)、プソロプテス・オウィス(Psoroptes ovis)、プソロプテス・クニクリ(Psoroptes cuniculi)、プソロプテス・エクィ(Psoroptes equi)、コリオプテス・ボウィス(Chorioptes bovis)、プソエルガテス・オウィス(Psoergates ovis)、プネウムモニュッソイディク・マンゲ(Pneumonyssoidic mange)、プネウモニュッソイデス・カニヌム(Pneumonyssoides caninum)、アカラピス・ヴォオディ(Acarapis woodi)である。
1.N−[(1S)−1−(4−{3−[3,5−ビス(トリフルオロメチル)フェニル]−3−(トリフルオロメチル)ピロリジン−1−イル}フェニル)エチル]シクロプロパンカルボキサミド(化合物番号11−b)の合成
(1)式(II)の化合物の調製方法−工程(i)
4−[1−ベンジル−3−(トリフルオロメチル)ピロリジン−3−イル]−2,6−ビス(トリフルオロメチル)ピリジンの合成
2,6−ビス(トリフルオロメチル)−4−[3−(トリフルオロメチル)ピロリジン−3−イル]ピリジンの合成
「−a」は、(R)−配置の化合物を意味する。このような化合物は、(R)−(+)−1−(4−ブロモフェニル)エチルアミンから合成される式(III)の化合物を介して調製方法(a)を用いて合成される。「−b」は、(S)−配置の化合物を意味する。このような化合物は、(S)−(−)−1−(4−ブロモフェニル)エチルアミンから合成される式(III)の化合物を介して調製方法(a)を用いて合成される。
特に断りがない限り、試験溶液は以下のとおりに調製した:
溶媒:ジメチルホルムアミド 3重量部
乳化剤:ポリオキシエチレンアルキルフェニルエーテル、 1重量部
試験溶液を調製するために、1重量部の活性化合物を、上記量の乳化剤を含有する、上記量の溶媒と混合し、この混合物を水で所望の濃度に希釈する。
R.H.は、相対湿度を意味し;hrsは、時間を意味する。
サツマイモの葉を適切な濃度の試験溶液中に浸漬させ、この葉を空気中で乾燥させた。次いで、葉を9cmの直径を有するペトリ皿に入れ、この中に10匹の第3虫齢の幼虫のスポドプテラ・リトゥラ(Spodoptera litura)を放した。このペトリ皿を25℃の温度調節室に置いた。2日および4日後に、さらにサツマイモの葉を追加した。7日後、死亡した幼虫の数を数え、殺虫力(insecticidal activity)を計算した。100%の殺虫力は、すべての幼虫を死滅させたことを意味する一方、0%の殺虫力は、死滅させた幼虫がいなかったことを意味する。現行試験において、それぞれの処理に対する2枚のペトリ皿の結果を平均した。
2.3gの人工飼料粉末をPETカップ(7.5cm直径、4cm深さ)中に入れる。この粉末を平らにし、カップの底部に層を作った。5mlの化学溶液を粉末上に注ぎ、均一に広がらせる。処理された飼料粉末を有するカップを静かに置いて、飼料をゼリー状にさせる。それぞれの試験カップ中に、5匹の第3虫齢の幼虫を放した。試験カップを蓋で閉じ、25℃および50−60%相対湿度、16L8D照明条件の温度調節室に置く。
1匹の幼虫死亡:20%効力
5匹の幼虫死亡:100%効力
50から100匹のテトラニュクス・ウリティカエ(Tetranychus urticae)の成虫ダニを、直径6cmのポットに植えた2葉期のインゲンマメの葉に接種した。1日後、適切な濃度の試験溶液をその上に十分な量でスプレーガンを用いて噴霧した。噴霧後、植物ポットを温室内に置き、7日後、殺ダニ力を計算した。100%の殺ダニ力は、すべてのダニを死滅させたことを意味し、0%の殺ダニ力は、死滅させたダニがいなかったことを意味する。
キュウリの葉を適切な濃度の試験溶液に浸漬させ、その葉を空気中で乾燥させた。次いで、葉を滅菌黒色土が入っているプラスチック製カップに入れ、5匹の第2虫齢幼虫のアウラコポラ・フェモラリス(Aulacophora femoralis)をカップ中に放した。カップを25℃の温度調節室に置いた。7日後、死んだ幼虫の数を数えて、殺虫力を計算した。100%の殺虫力は、幼虫をすべて死滅させたことを意味する一方、0%の殺虫力は、死滅させた幼虫がいなかったことを意味する。
溶媒:ジメチルスルホキシド
活性化合物の適切な調製物を作るために、10mgの活性化合物を0.5mlの溶媒に溶解させ、この濃縮物を水で所望の濃度に希釈する。マダニ(アムブリュオンマ・ヘブラエウム(Amblyomma hebraeum))の若虫を有孔プラスチック製ビーカーに入れ、化合物水溶液に1分間浸漬させる。マダニをペトリ皿中のろ紙に移し、人工気象室で42日間インキュベートする。
溶媒:ジメチルスルホキシド
活性化合物の適切な調製物を作るために、10mgの活性化合物を0.5mlの溶媒に溶解させ、この濃縮物を水で所望の濃度に希釈する。8から10匹の成虫の充血したメスのボオピルス・ミクロプルス(Boophilus microplus)マダニを有孔プラスチック製ビーカーに入れ、化合物水溶液に1分間浸漬させる。マダニをプラスチック製トレイ中のろ紙に移した。その後、受精卵の産卵をモニターする。7日後、死亡率(%)を測定する。100%は、マダニのすべてを死滅させたことを意味し;0%は、死滅させたマダニはいなかったことを意味する。
溶媒:ジメチルスルホキシド
適切な活性化合物の調製物を作るために、10mgの活性化合物を0.5mlの溶媒に溶解させ、この濃縮物を溶媒で所望の濃度に希釈する。5匹の成虫の充血したメスのマダニ(ボオピルス・ミクロプルス(Boophilus microplus))に、1μlの化合物溶液を腹部に注射する。マダニをレプリカプレート中に移し、人工気象室中で一定期間インキュベートする。受精卵の産卵をモニターする。
溶媒:ジメチルスルホキシド
活性化合物の適切な調製物を作るために、10mgの活性化合物を0.5mlの溶媒中に溶解させ、この濃縮物をウシの血液で所望の濃度に希釈する。約20匹の餌を与えていない成虫(クテノケパリデス・フェリス(Ctenocephalides felis))をノミチャンバ(flea chamber)に置く。底部をパラフィンで封止した血液チャンバを、化合物溶液を補充したウシ血液で満たし、ノミが血液を吸うことができるように、ノミチャンバの上部に置く。血液チャンバを37℃に加熱する一方、ノミチャンバは室温に保つ。
種:ルキリア・クプリナ(Lucilia cuprina)第1虫齢幼虫(虫齢24時間)
溶媒:ジメチルスルホキシド
10mgの活性化合物を0.5mlのジメチルスルホキシドに溶解させる。所望の率を得るために一連の希釈液を作製する。約20匹のルキリア・クプリナ(Lucilia cuprina)の第1虫齢幼虫を、1cm3のミンチした馬肉および試験化合物の希釈水溶液0.5mlが入っている試験管中に移す。
溶媒:ジメチルスルホキシド
活性化合物の適切な調製物を作るために、10mgの活性化合物を0.5mlの溶媒に溶解させ、この濃縮物を水で所望の濃度に希釈する。アッセイ前に、一片のキッチンスポンジをショ糖および化合物溶液の混合物に浸し、容器中に入れる:10匹の成虫(ムスカ・ドメスティカ(Musca domestica))を容器中に入れ、有孔蓋で閉じる。
10部の本発明の化合物(例えば、化合物番号1)、30部のベントナイト(モンモリロナイト)、58部のタルクおよび2部のリグニンスルホネートを含む混合物に、25部の水を添加し、この混合物を十分に混練し、押出し造粒機によって10から40メッシュで粒状にし、40から50℃で乾燥させて、顆粒剤を得た。
95部の0.2から2mmの範囲内の粒径分布を有するクレー鉱物粒を、回転式混合器に入れ、次いで、回転状態下で液体希釈剤と一緒に5部の本発明の化合物(例えば、化合物番号1)を噴霧することによって均一に湿らせ、40から50℃で乾燥させて、顆粒剤を得た。
30部の本発明の化合物(例えば、化合物番号1)、55部のキシレン、8部のポリオキシエチレンアルキルフェニルエーテルおよび7部のアルキルベンゼンスルホン酸カルシウムを一緒に混合して、エマルション剤を得た。
15部の本発明による化合物(例えば、化合物番号1)、80部の、ホワイトカーボン(水和非晶質二酸化ケイ素微粉)および粉末クレー(1:5)の混合物、2部のアルキルベンゼンスルホン酸ナトリウムおよび3部のアルキルナフタレンスルホン酸ナトリウムのホルマリン縮合物を一緒に混合し、この混合物を破砕して、水和剤を得た。
20部の本発明による化合物(例えば、化合物番号1)、30部のリグニンスルホン酸ナトリウム、15部のベントナイトおよび35部の焼成珪藻土粉末を十分に混合し、水を添加後、この混合物を0.3mmのスクリーンで押出し、乾燥させて、顆粒水和剤を得た。
Claims (13)
- 式(I)
Aは、C−X3または窒素であり;
X1、X2、X3およびX4は、それぞれ独立して、水素、ハロゲン、C1−4ハロアルキル、C1−4ハロアルコキシ、C1−4ハロアルキルチオ、C1−4ハロアルキルスルフィニルおよびC1−4ハロアルキルスルホニルであり;
R1は、C1−4ハロアルキルであり;
R2は、C1−4アルキル、C1−4ハロアルキル、C3−6シクロアルキルまたはシアノであり;
R3は、水素、C1−4アルキルまたはC1−4ハロアルキルであり;
R4は、C1−4アルキル、C1−4ハロアルキル、C3−6シクロアルキル、C3−6シクロアルキル−C1−4アルキル;C3−6ハロシクロアルキル、C1−4アルコキシ、C1−4アルコキシ−C1−4アルキル、C1−4ハロアルコキシ−C1−4アルキル、C1−4アルキルチオ−C1−4アルキル、C1−4アルキルスルフィニル−C1−4アルキル、C1−4アルキルスルホニル−C1−4アルキル、C1−4ハロアルキルチオ−C1−4アルキル、C1−4ハロアルキルスルフィニル−C1−4アルキル、C1−4ハロアルキルスルホニル−C1−4アルキルまたはC1−4アルキルアミノ、ハロゲン置換フェニルであり;
Gは、OまたはSである。)
のアリールピロリジン化合物。 - 請求項1に記載のアリールピロリジン化合物であって、
Aが、C−X3であり;
X1、X2、X3およびX4が、それぞれ独立して、水素、ハロゲンまたはC1−4ハロアルキルであり;
R1が、トリフルオロメチルであり;
R2が、メチル、エチルまたはシクロプロピルであり;
R3が、水素であり;
R4が、メチル、エチル、シクロプロピル、シクロプロピルメチル、2,2,2−トリフルオロエチル、2−メトキシエチル、メチルチオメチル、メチルスルフィニルメチル、メチルスルホニルメチルまたは2,4,6−トリフルオロフェニルであり;
Gが、Oである、アリールピロリジン化合物。 - 請求項1に記載のアリールピロリジン化合物であって、
Aが、C−H、C−ClまたはCCF3であり;
X1、X2、X3およびX4が、それぞれ独立して、水素、フッ素、塩素もしくは臭素またはCF3であり;
R1が、トリフルオロメチルであり;
R2が、メチルであり;
R3が、水素であり;
R4が、メチル、エチルまたはシクロプロピル、シクロプロピルメチル、メトキシエチル、2,4,6−トリフルオロフェニルであり;
Gが、Oである、アリールピロリジン化合物。 - 請求項1から4のいずれか一項に記載のアリールピロリジン化合物であって、
Aが、C−X3であり;
X1、X2、X3およびX4が、それぞれ独立して、水素、塩素またはCF3であり;
R1が、トリフルオロメチルであり;
R2が、メチルであり;
R3が、水素であり;
R4が、メチル、エチルまたはシクロプロピル、シクロプロピルメチル、メトキシエチル、2,4,6−トリフルオロフェニルであり;
Gが、Oである、アリールピロリジン化合物。 - 請求項1または4に記載のアリールピロリジン化合物であって、
Aが、C−X3であり;
X1、X3、R3がそれぞれ、水素であり;
X2、X4、R1がそれぞれ、CF3であり;
R2が、メチルであり;
R4が、メチル、エチルまたはシクロプロピル、シクロプロピルメチル、メトキシエチル、2,4,6−トリフルオロフェニルであり;
Gが、Oである、アリールピロリジン化合物。 - 請求項1または4に記載のアリールピロリジン化合物であって、
Aが、C−X3であり;
X1、X3、R3がそれぞれ、水素であり;
X2、X4がそれぞれ、塩素であり;
R1が、CF3であり;
R2が、メチルであり;
R4が、メチル、エチルまたはシクロプロピルであり;
Gが、Oである、アリールピロリジン化合物。 - 請求項1または4に記載のアリールピロリジン化合物であって、
Aが、C−X3であり;
X1、X3、R3がそれぞれ、水素であり;
X2が、塩素であり;
R1、X4がそれぞれ、CF3であり;
R2が、メチルであり;
R4が、メチル、エチルまたはシクロプロピルであり;
Gが、Oである、アリールピロリジン化合物。 - 請求項1または4に記載のアリールピロリジン化合物であって、
Aが、C−X3であり;
X1、R3がそれぞれ、水素であり;
X2、X3、X4がそれぞれ、塩素であり;
R1が、CF3であり;
R2が、メチルであり;
R4が、メチル、エチルまたはシクロプロピル、シクロプロピルメチル、メトキシエチルであり;
Gが、Oである、アリールピロリジン化合物。 - 請求項1または4に記載のアリールピロリジン化合物であって、
Aが、窒素であり;
X1、X3がそれぞれ、水素であり;
X2、X4、R1がそれぞれ、CF3であり;
R2が、メチルであり;
R4が、シクロプロピルであり;
Gが、Oである、アリールピロリジン化合物。 - 昆虫類、クモ形類動物、蠕虫類、線虫類および軟体動物を防除するための、請求項1から10のいずれか一項に記載の少なくとも1種のアリールピロリジン化合物を含む殺虫性組成物。
- 殺虫剤、殺ダニ剤、殺線虫剤、殺真菌剤、生物学的防除剤および殺菌剤から選択される少なくとも別の活性成分をさらに含む、請求項11に記載の殺虫性組成物。
- 内部寄生虫または外部寄生虫を防除するための、請求項1から10のいずれか一項に記載の少なくとも1種のアリールピロリジン化合物を含む獣医学組成物。
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EP (1) | EP2519499B1 (ja) |
JP (2) | JP2011136928A (ja) |
KR (1) | KR20120110146A (ja) |
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BR (1) | BR112012015943A2 (ja) |
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MX (1) | MX2012007521A (ja) |
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JP2011136928A (ja) | 2009-12-28 | 2011-07-14 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
JP2012082186A (ja) * | 2010-09-15 | 2012-04-26 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
JP2014015397A (ja) * | 2010-11-04 | 2014-01-30 | Nippon Soda Co Ltd | 動物用外部寄生虫防除剤 |
EP3896058A3 (en) | 2011-10-03 | 2022-01-12 | Syngenta Participations Ag | Enantionselective processes to insecticidal 3-aryl-3-trifluoromethyl-substituted pyrrolidines |
CN103857656B (zh) * | 2011-10-03 | 2016-09-14 | 先正达参股股份有限公司 | 杀虫的3-芳基-3-三氟甲基-取代的吡咯烷的对映选择性方法 |
WO2013087712A1 (en) * | 2011-12-14 | 2013-06-20 | Syngenta Participations Ag | Pesticidal mixtures |
CN104011026B (zh) * | 2011-12-20 | 2016-07-20 | 拜耳知识产权股份有限公司 | 杀虫用芳酰胺 |
BR112014021674A2 (pt) | 2012-03-14 | 2019-09-24 | Bayer Ip Gmbh | arilpirrolidinas pesticidas |
WO2014019609A1 (en) | 2012-07-31 | 2014-02-06 | Syngenta Participations Ag | Methods of pest control in soybean |
WO2014019957A2 (en) | 2012-08-03 | 2014-02-06 | Syngenta Participations Ag | Methods of pest control in soybean |
WO2014029708A1 (en) * | 2012-08-24 | 2014-02-27 | Syngenta Participations Ag | Methods of controlling insects |
MX350575B (es) * | 2012-09-27 | 2017-09-11 | Bayer Cropscience Ag | Procedimiento para la preparación de fenil y piridil pirrolidinas opcionalmente sustituidas. |
CN105218424A (zh) * | 2015-09-08 | 2016-01-06 | 李强 | 一种吡咯类化合物的催化合成方法 |
CN105218423A (zh) * | 2015-09-08 | 2016-01-06 | 李强 | 一种芳基取代吡咯化合物的合成方法 |
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DK1731512T3 (en) | 2004-03-05 | 2015-01-05 | Nissan Chemical Ind Ltd | Isoxazoline-substituted benzamide AND INSTRUMENTS FOR COMBATING HARMFUL ORGANISMS |
TWI382020B (zh) | 2004-10-20 | 2013-01-11 | Kumiai Chemical Industry Co | 3-三唑基苯基硫醚衍生物及以其為有效成份之殺蟲、殺蟎、殺線蟲劑 |
DE102005008021A1 (de) | 2005-02-22 | 2006-08-24 | Bayer Cropscience Ag | Spiroketal-substituierte cyclische Ketoenole |
TWI398433B (zh) | 2006-02-10 | 2013-06-11 | Dow Agrosciences Llc | 殺蟲性之n-取代(6-鹵烷基吡啶-3-基)烷基磺醯亞胺 |
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DE102006015470A1 (de) | 2006-03-31 | 2007-10-04 | Bayer Cropscience Ag | Substituierte Enaminocarbonylverbindungen |
TWI381811B (zh) | 2006-06-23 | 2013-01-11 | Dow Agrosciences Llc | 用以防治可抵抗一般殺蟲劑之昆蟲的方法 |
JP5164510B2 (ja) | 2006-10-06 | 2013-03-21 | 日本曹達株式会社 | 含窒素複素環化合物および有害生物防除剤 |
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MY146638A (en) * | 2007-04-10 | 2012-09-14 | Bayer Cropscience Ag | Insecticidal aryl isoxazoline derivatives |
JP2008266230A (ja) * | 2007-04-23 | 2008-11-06 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
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US20120129854A1 (en) | 2009-04-30 | 2012-05-24 | Bayer Cropscience Ag | Pesticidal Arylpyrrolidines |
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ES2435494T3 (es) | 2013-12-19 |
JP2011136928A (ja) | 2011-07-14 |
CN102844299A (zh) | 2012-12-26 |
US20120322833A1 (en) | 2012-12-20 |
TW201136914A (en) | 2011-11-01 |
CN102844299B (zh) | 2016-03-30 |
MX2012007521A (es) | 2012-11-12 |
EP2519499A1 (en) | 2012-11-07 |
AR079748A1 (es) | 2012-02-15 |
US8536201B2 (en) | 2013-09-17 |
BR112012015943A2 (pt) | 2017-01-10 |
EP2519499B1 (en) | 2013-09-18 |
JP2013515699A (ja) | 2013-05-09 |
UY33157A (es) | 2011-07-29 |
WO2011080211A1 (en) | 2011-07-07 |
KR20120110146A (ko) | 2012-10-09 |
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