ZA200601274B - 1,2,4-thiadiazole compounds and pests controlling composition containing the same - Google Patents
1,2,4-thiadiazole compounds and pests controlling composition containing the same Download PDFInfo
- Publication number
- ZA200601274B ZA200601274B ZA200601274A ZA200601274A ZA200601274B ZA 200601274 B ZA200601274 B ZA 200601274B ZA 200601274 A ZA200601274 A ZA 200601274A ZA 200601274 A ZA200601274 A ZA 200601274A ZA 200601274 B ZA200601274 B ZA 200601274B
- Authority
- ZA
- South Africa
- Prior art keywords
- thiadiazole
- optionally substituted
- formula
- ethylene
- thiadiazole compound
- Prior art date
Links
- 241000607479 Yersinia pestis Species 0.000 title claims description 21
- 239000000203 mixture Substances 0.000 title claims description 12
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 title description 5
- -1 1,2,4-thiadiazole compound Chemical class 0.000 claims description 182
- 125000000304 alkynyl group Chemical group 0.000 claims description 31
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 125000004450 alkenylene group Chemical group 0.000 claims description 23
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- LCGXGBNCOZXAHT-UHFFFAOYSA-N 3-but-2-ynoxy-5-(2-methylpiperidin-1-yl)-1,2,4-thiadiazole Chemical compound CC#CCOC1=NSC(N2C(CCCC2)C)=N1 LCGXGBNCOZXAHT-UHFFFAOYSA-N 0.000 claims 1
- VCTUMNBHEOUTQU-UHFFFAOYSA-N 3-but-2-ynoxy-5-(3,5-diethylpiperidin-1-yl)-1,2,4-thiadiazole Chemical compound C1C(CC)CC(CC)CN1C1=NC(OCC#CC)=NS1 VCTUMNBHEOUTQU-UHFFFAOYSA-N 0.000 claims 1
- XJMSCHUGCVHUGJ-UHFFFAOYSA-N 3-but-2-ynoxy-5-(3,5-dimethylpiperidin-1-yl)-1,2,4-thiadiazole Chemical compound CC#CCOC1=NSC(N2CC(C)CC(C)C2)=N1 XJMSCHUGCVHUGJ-UHFFFAOYSA-N 0.000 claims 1
- SOWMMBGHBYYWLY-UHFFFAOYSA-N 3-but-2-ynoxy-5-(3-methylpiperidin-1-yl)-1,2,4-thiadiazole Chemical compound CC#CCOC1=NSC(N2CC(C)CCC2)=N1 SOWMMBGHBYYWLY-UHFFFAOYSA-N 0.000 claims 1
- VQDWTPJRBGUZLL-UHFFFAOYSA-N 3-but-2-ynoxy-5-(4-methylpiperidin-1-yl)-1,2,4-thiadiazole Chemical compound CC#CCOC1=NSC(N2CCC(C)CC2)=N1 VQDWTPJRBGUZLL-UHFFFAOYSA-N 0.000 claims 1
- VZRJIFJKEWYVHQ-UHFFFAOYSA-N 3-but-2-ynoxy-5-[3-(trifluoromethyl)piperidin-1-yl]-1,2,4-thiadiazole Chemical compound CC#CCOC1=NSC(N2CC(CCC2)C(F)(F)F)=N1 VZRJIFJKEWYVHQ-UHFFFAOYSA-N 0.000 claims 1
- WSMRXTPTAYORAX-UHFFFAOYSA-N 3-but-2-ynoxy-5-pyrrolidin-1-yl-1,2,4-thiadiazole Chemical compound CC#CCOC1=NSC(N2CCCC2)=N1 WSMRXTPTAYORAX-UHFFFAOYSA-N 0.000 claims 1
- WDTNXSMJLBOWBG-UHFFFAOYSA-N 3-pent-2-ynoxy-5-piperidin-1-yl-1,2,4-thiadiazole Chemical compound CCC#CCOC1=NSC(N2CCCCC2)=N1 WDTNXSMJLBOWBG-UHFFFAOYSA-N 0.000 claims 1
- WSCCCJMFSHVJCD-UHFFFAOYSA-N 4-(3-but-2-ynoxy-1,2,4-thiadiazol-5-yl)-2,6-dimethylmorpholine Chemical compound CC#CCOC1=NSC(N2CC(C)OC(C)C2)=N1 WSCCCJMFSHVJCD-UHFFFAOYSA-N 0.000 claims 1
- TYLANNXSZLVKTQ-UHFFFAOYSA-N 4-(3-but-2-ynoxy-1,2,4-thiadiazol-5-yl)morpholine Chemical compound CC#CCOC1=NSC(N2CCOCC2)=N1 TYLANNXSZLVKTQ-UHFFFAOYSA-N 0.000 claims 1
- QVSAQPVGDZGOOU-UHFFFAOYSA-N 4-(3-pent-2-ynoxy-1,2,4-thiadiazol-5-yl)morpholine Chemical compound CCC#CCOC1=NSC(N2CCOCC2)=N1 QVSAQPVGDZGOOU-UHFFFAOYSA-N 0.000 claims 1
- QLCXIIACSSJGQB-UHFFFAOYSA-N 5-(2-methylpiperidin-1-yl)-3-pent-2-ynoxy-1,2,4-thiadiazole Chemical compound CCC#CCOC1=NSC(N2C(CCCC2)C)=N1 QLCXIIACSSJGQB-UHFFFAOYSA-N 0.000 claims 1
- DGFSVRKAUGIUDN-UHFFFAOYSA-N 5-(3,5-dimethylpiperidin-1-yl)-3-pent-2-ynoxy-1,2,4-thiadiazole Chemical compound CCC#CCOC1=NSC(N2CC(C)CC(C)C2)=N1 DGFSVRKAUGIUDN-UHFFFAOYSA-N 0.000 claims 1
- KXNVIOZLRWMIEU-UHFFFAOYSA-N 5-(3,5-dimethylpiperidin-1-yl)-3-pent-3-yn-2-yloxy-1,2,4-thiadiazole Chemical compound CC#CC(C)OC1=NSC(N2CC(C)CC(C)C2)=N1 KXNVIOZLRWMIEU-UHFFFAOYSA-N 0.000 claims 1
- CDUWVHMMJCAJEB-UHFFFAOYSA-N 5-(3,5-dimethylpiperidin-1-yl)-3-prop-2-ynoxy-1,2,4-thiadiazole Chemical compound C1C(C)CC(C)CN1C1=NC(OCC#C)=NS1 CDUWVHMMJCAJEB-UHFFFAOYSA-N 0.000 claims 1
- SCYKLERABUDXAV-UHFFFAOYSA-N 5-(3-methylpiperidin-1-yl)-3-pent-2-ynoxy-1,2,4-thiadiazole Chemical compound CCC#CCOC1=NSC(N2CC(C)CCC2)=N1 SCYKLERABUDXAV-UHFFFAOYSA-N 0.000 claims 1
- ZNWGXOMWMZPAAU-UHFFFAOYSA-N 5-(4-methylpiperidin-1-yl)-3-pent-2-ynoxy-1,2,4-thiadiazole Chemical compound CCC#CCOC1=NSC(N2CCC(C)CC2)=N1 ZNWGXOMWMZPAAU-UHFFFAOYSA-N 0.000 claims 1
- JRNMAHKOJAXWAV-UHFFFAOYSA-N 5-(azepan-1-yl)-3-but-2-ynoxy-1,2,4-thiadiazole Chemical compound CC#CCOC1=NSC(N2CCCCCC2)=N1 JRNMAHKOJAXWAV-UHFFFAOYSA-N 0.000 claims 1
- TUTJFESFRDGPJK-UHFFFAOYSA-N 5-(azepan-1-yl)-3-pent-2-ynoxy-1,2,4-thiadiazole Chemical compound CCC#CCOC1=NSC(N2CCCCCC2)=N1 TUTJFESFRDGPJK-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 230000001276 controlling effect Effects 0.000 description 10
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000001590 oxidative effect Effects 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical group C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- SMOHMDMTVAYPAI-UHFFFAOYSA-N 2,3,6,7-tetrahydro-1h-azepine Chemical compound C1CC=CCCN1 SMOHMDMTVAYPAI-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- IFRYKIFAMMXTOF-UHFFFAOYSA-N 5-chloro-3-methylsulfanyl-1,2,4-thiadiazole Chemical compound CSC1=NSC(Cl)=N1 IFRYKIFAMMXTOF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 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
- A01N43/72—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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003354758 | 2003-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200601274B true ZA200601274B (en) | 2007-05-30 |
Family
ID=34463149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200601274A ZA200601274B (en) | 2003-10-15 | 2004-09-27 | 1,2,4-thiadiazole compounds and pests controlling composition containing the same |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7371746B2 (zh) |
| EP (2) | EP1765798A2 (zh) |
| JP (1) | JP4706225B2 (zh) |
| KR (1) | KR101032834B1 (zh) |
| CN (1) | CN101208318B (zh) |
| AU (1) | AU2004282018B2 (zh) |
| BR (1) | BRPI0415364A (zh) |
| CO (1) | CO5660294A2 (zh) |
| IL (1) | IL173699A (zh) |
| MX (1) | MXPA06004118A (zh) |
| TW (1) | TWI364422B (zh) |
| WO (1) | WO2005037805A2 (zh) |
| ZA (1) | ZA200601274B (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201841890A (zh) * | 2017-04-05 | 2018-12-01 | 日商阿格諾卡那休股份有限公司 | 新穎1-苯基哌啶衍生物及以其為有效成份之農園藝用藥劑 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3030661A1 (de) | 1980-08-13 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | Hetaryl-propargylether, ihre herstellung und ihre verwendung in schaedlingsbekaempfungsmitteln, diese stoffe enthaltende schaedlingsbekaempfungsmittel, sowie ihre herstellung und verwendung |
| EP0116515B1 (de) * | 1983-01-19 | 1988-09-21 | Ciba-Geigy Ag | Schädlingsbekämpfungsmittel |
| GB8509752D0 (en) * | 1985-04-16 | 1985-05-22 | Fbc Ltd | Acaricides |
| US5405853A (en) * | 1987-09-10 | 1995-04-11 | Merck Sharpe & Dohme Ltd. | Thiadiazoles useful in the treatment of senile dementia |
| DE4341066A1 (de) * | 1993-05-03 | 1994-11-10 | Bayer Ag | Oxa(Thia)-diazol-oxy-phenylacrylate |
| US6162791A (en) * | 1998-03-02 | 2000-12-19 | Apotex Inc. | Thiadiazole compounds useful as inhibitors of cysteine activity dependent enzymes |
| US6468977B1 (en) * | 1998-03-02 | 2002-10-22 | Apotex Inc. | Thiadiazole compounds useful as inhibitors of cysteine activity dependent enzymes |
| US6060472A (en) * | 1998-04-06 | 2000-05-09 | Apotex Inc. | Thiadiazole compounds useful as inhibitors of H+ /K+ atpase |
| JP4923334B2 (ja) | 2001-05-22 | 2012-04-25 | 住友化学株式会社 | １，２，４−チアジアゾール化合物及びその用途 |
| WO2003059897A1 (fr) | 2002-01-17 | 2003-07-24 | Sumitomo Chemical Company, Limited | Composes de thiadiazole |
| JP4513251B2 (ja) | 2002-10-11 | 2010-07-28 | 住友化学株式会社 | チアジアゾール化合物およびその用途 |
| US7361675B2 (en) | 2002-11-08 | 2008-04-22 | Sumitomo Chemical Company Limited | 1,2,4-thiadiazole compounds and use thereof |
| CN100408625C (zh) * | 2002-11-21 | 2008-08-06 | 株式会社钟化 | 热塑性弹性体组合物 |
| US6858605B2 (en) * | 2003-02-04 | 2005-02-22 | Ivax Drug Research Institute, Ltd. | Substituted 2,3-benzodiazepine derivatives |
| DE102004032567A1 (de) * | 2004-07-05 | 2006-03-02 | Grünenthal GmbH | Substituierte 1-Propiolyl-piperazine |
-
2004
- 2004-09-27 KR KR1020067007218A patent/KR101032834B1/ko not_active IP Right Cessation
- 2004-09-27 EP EP04773569A patent/EP1765798A2/en not_active Withdrawn
- 2004-09-27 MX MXPA06004118A patent/MXPA06004118A/es active IP Right Grant
- 2004-09-27 ZA ZA200601274A patent/ZA200601274B/en unknown
- 2004-09-27 US US10/567,984 patent/US7371746B2/en not_active Expired - Fee Related
- 2004-09-27 WO PCT/JP2004/014540 patent/WO2005037805A2/en active Application Filing
- 2004-09-27 BR BRPI0415364-2A patent/BRPI0415364A/pt not_active IP Right Cessation
- 2004-09-27 CN CN2004800302947A patent/CN101208318B/zh not_active Expired - Fee Related
- 2004-09-27 EP EP12164449A patent/EP2492265A1/en not_active Withdrawn
- 2004-09-27 AU AU2004282018A patent/AU2004282018B2/en not_active Ceased
- 2004-09-29 TW TW093129483A patent/TWI364422B/zh not_active IP Right Cessation
- 2004-10-12 JP JP2004297325A patent/JP4706225B2/ja not_active Expired - Fee Related
-
2006
- 2006-02-13 IL IL173699A patent/IL173699A/en not_active IP Right Cessation
- 2006-03-15 CO CO06026137A patent/CO5660294A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005037805A3 (en) | 2007-11-22 |
| IL173699A0 (en) | 2006-07-05 |
| EP2492265A1 (en) | 2012-08-29 |
| IL173699A (en) | 2012-02-29 |
| BRPI0415364A (pt) | 2006-12-12 |
| JP4706225B2 (ja) | 2011-06-22 |
| JP2005139171A (ja) | 2005-06-02 |
| AU2004282018A1 (en) | 2005-04-28 |
| KR20070018794A (ko) | 2007-02-14 |
| CO5660294A2 (es) | 2006-07-31 |
| WO2005037805A2 (en) | 2005-04-28 |
| TWI364422B (en) | 2012-05-21 |
| MXPA06004118A (es) | 2006-07-05 |
| AU2004282018B2 (en) | 2009-07-23 |
| CN101208318A (zh) | 2008-06-25 |
| US20070004722A1 (en) | 2007-01-04 |
| US7371746B2 (en) | 2008-05-13 |
| TW200519107A (en) | 2005-06-16 |
| CN101208318B (zh) | 2010-11-03 |
| EP1765798A2 (en) | 2007-03-28 |
| KR101032834B1 (ko) | 2011-05-06 |
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