JPS5829953B2 - チアゾ−ル誘導体の製造方法 - Google Patents
チアゾ−ル誘導体の製造方法Info
- Publication number
- JPS5829953B2 JPS5829953B2 JP55075388A JP7538880A JPS5829953B2 JP S5829953 B2 JPS5829953 B2 JP S5829953B2 JP 55075388 A JP55075388 A JP 55075388A JP 7538880 A JP7538880 A JP 7538880A JP S5829953 B2 JPS5829953 B2 JP S5829953B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- hydrogen
- pyridyl
- general formula
- alkyl
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000007979 thiazole derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
- -1 mucycloalkyl Chemical group 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- XQWBMZWDJAZPPX-UHFFFAOYSA-N pyridine-3-carbothioamide Chemical compound NC(=S)C1=CC=CN=C1 XQWBMZWDJAZPPX-UHFFFAOYSA-N 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 229910001868 water Inorganic materials 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 241001124076 Aphididae Species 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 241000238631 Hexapoda Species 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Chemical class 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 239000002917 insecticide Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 240000005979 Hordeum vulgare Species 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- PNJYSPUXYJWHJJ-UHFFFAOYSA-N ethyl 4-methyl-2-pyridin-3-yl-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(C=2C=NC=CC=2)=N1 PNJYSPUXYJWHJJ-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- WPCSNGBKVXKBPU-UHFFFAOYSA-N 2-pyridin-3-yl-1,3-thiazole Chemical compound C1=CSC(C=2C=NC=CC=2)=N1 WPCSNGBKVXKBPU-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000003557 thiazoles Chemical class 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 244000141359 Malus pumila Species 0.000 description 3
- 235000011430 Malus pumila Nutrition 0.000 description 3
- 235000015103 Malus silvestris Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 230000008029 eradication Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical compound NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- SGZYGCWIEWKSLU-UHFFFAOYSA-N 4-methyl-2-pyridin-3-yl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(N)=O)=C(C)N=C1C1=CC=CN=C1 SGZYGCWIEWKSLU-UHFFFAOYSA-N 0.000 description 2
- 241001095118 Aphis pomi Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 2
- RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- HNLXNOZHXNSSPN-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[4-(2,4,4-trimethylpentan-2-yl)phenoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCOCCOCCOCCO)C=C1 HNLXNOZHXNSSPN-UHFFFAOYSA-N 0.000 description 1
- HAHRKWVTAOAAOE-UHFFFAOYSA-N 3-dodecyl-4-methyl-2-pyridin-3-yl-2H-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N(CCCCCCCCCCCC)C1C1=CC=CN=C1 HAHRKWVTAOAAOE-UHFFFAOYSA-N 0.000 description 1
- XFYYQDHEDOXWGA-UHFFFAOYSA-N 4-[(5-bromopyridin-2-yl)amino]-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)NC1=CC=C(Br)C=N1 XFYYQDHEDOXWGA-UHFFFAOYSA-N 0.000 description 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- DMOMFIQLVIVOHK-UHFFFAOYSA-N 4-methyl-2-pyridin-3-yl-1,3-thiazole-5-carbonyl chloride;hydrochloride Chemical compound Cl.S1C(C(Cl)=O)=C(C)N=C1C1=CC=CN=C1 DMOMFIQLVIVOHK-UHFFFAOYSA-N 0.000 description 1
- CJLQNROYBZEUGH-UHFFFAOYSA-N 4-methyl-2-pyridin-3-yl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1C1=CC=CN=C1 CJLQNROYBZEUGH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000256118 Aedes aegypti Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 240000005250 Chrysanthemum indicum Species 0.000 description 1
- 241000258935 Chrysopidae Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000526145 Psylla Species 0.000 description 1
- 241000208422 Rhododendron Species 0.000 description 1
- 241000426569 Rhopalosiphum insertum Species 0.000 description 1
- 241000167882 Rhopalosiphum maidis Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241001414987 Strepsiptera Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- JFMUMWUZCSFMDD-UHFFFAOYSA-N methyl 2-pyridin-3-yl-1,3-thiazole-5-carboxylate Chemical compound S1C(C(=O)OC)=CN=C1C1=CC=CN=C1 JFMUMWUZCSFMDD-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- OJWCSSAVNSLZNS-UHFFFAOYSA-N n-tert-butyl-4-methyl-2-pyridin-3-yl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)NC(C)(C)C)=C(C)N=C1C1=CC=CN=C1 OJWCSSAVNSLZNS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000005480 nicotinamides Chemical class 0.000 description 1
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- PVEFEIWVJKUCLJ-UHFFFAOYSA-N sulfuric acid;toluene Chemical compound OS(O)(=O)=O.CC1=CC=CC=C1 PVEFEIWVJKUCLJ-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- GGNIKGLUPSHSBV-UHFFFAOYSA-N thiazole-5-carboxamide Chemical compound NC(=O)C1=CN=CS1 GGNIKGLUPSHSBV-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14057171A | 1971-05-05 | 1971-05-05 | |
| US06/045,809 US4260765A (en) | 1971-05-05 | 1979-06-05 | 2-(3-Pyridyl)-5-thiazolecarboxamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5612386A JPS5612386A (en) | 1981-02-06 |
| JPS5829953B2 true JPS5829953B2 (ja) | 1983-06-25 |
Family
ID=26723223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55075388A Expired JPS5829953B2 (ja) | 1971-05-05 | 1980-06-04 | チアゾ−ル誘導体の製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US4080457A (forum.php) |
| JP (1) | JPS5829953B2 (forum.php) |
| AU (1) | AU469596B2 (forum.php) |
| BE (1) | BE782949A (forum.php) |
| CA (1) | CA962269A (forum.php) |
| CH (2) | CH580097A5 (forum.php) |
| DE (1) | DE2221647C2 (forum.php) |
| FR (1) | FR2135287B1 (forum.php) |
| GB (1) | GB1382854A (forum.php) |
| LU (1) | LU65289A1 (forum.php) |
| NL (1) | NL177117C (forum.php) |
Families Citing this family (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443455A (en) * | 1978-02-17 | 1984-04-17 | Imperial Chemical Industries Plc | Fungidical thiazolidinones |
| US4443454A (en) * | 1978-02-17 | 1984-04-17 | Imperial Chemical Industries Plc | Thiazolidinones |
| FR2464954A2 (fr) * | 1979-09-12 | 1981-03-20 | Rhone Poulenc Ind | Nouveaux derives de la thiazolidine, leur preparation et les compositions qui les contiennent |
| JPS5522636A (en) * | 1978-08-04 | 1980-02-18 | Takeda Chem Ind Ltd | Thiazoliding derivative |
| US4436739A (en) | 1978-10-16 | 1984-03-13 | Eli Lilly And Company | Substituted 1-thia-3-aza-4-ones |
| US4482712A (en) * | 1978-10-16 | 1984-11-13 | Eli Lilly And Company | Substituted 1-thia-3-aza-4-ones |
| AU5165479A (en) * | 1978-10-16 | 1980-04-24 | Eli Lilly And Company | Substituted 1-thia-3-aza-4-ones |
| DE3170401D1 (en) * | 1980-07-28 | 1985-06-13 | Ciba Geigy Ag | Triazoline derivatives and processes for their preparation |
| EP0062612A1 (de) * | 1981-04-02 | 1982-10-13 | Ciba-Geigy Ag | Neue Thiazolinderivate |
| FR2517176A1 (fr) * | 1981-12-01 | 1983-06-03 | Rhone Poulenc Agrochimie | Association insecticide et acaricide a base de pyrethroide |
| US4571402A (en) * | 1982-06-22 | 1986-02-18 | Schering Corporation | Anti-bronchoconstriction 2-(4'-pyridinyl)-thiazole derivatives, composition, and method of use therefor |
| DE3247118A1 (de) * | 1982-12-20 | 1984-06-20 | Cassella Ag, 6000 Frankfurt | Neue substituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4649146A (en) * | 1983-01-31 | 1987-03-10 | Fujisawa Pharmaceutical Co., Ltd. | Thiazole derivatives and pharmaceutical composition comprising the same |
| US4697012A (en) * | 1984-07-25 | 1987-09-29 | Merck & Co., Inc. | Morpholino pyridyl thiazole compound |
| DE3443179A1 (de) * | 1984-11-27 | 1986-05-28 | Cassella Ag, 6000 Frankfurt | 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung |
| HU200177B (en) * | 1985-06-18 | 1990-04-28 | Biogal Gyogyszergyar | Process for producing thiazolidinecarboxylic acids and pharmaceutical compositions comprising such compounds |
| US4746669A (en) * | 1985-12-23 | 1988-05-24 | Merck & Co., Inc. | Substituted thiazoles as immunoregulants |
| DE3932052A1 (de) * | 1989-09-26 | 1991-04-04 | Basf Ag | Oxazol- bzw. thiazolcarbonsaeureamide |
| EP0513387B1 (en) | 1990-11-30 | 2000-03-01 | Otsuka Pharmaceutical Co., Ltd. | Thiazole derivatives as active oxygen inhibitors |
| SG86971A1 (en) * | 1990-11-30 | 2002-03-19 | Teijin Ltd | 2-arylthiazole derivatives and pharmaceutical composition thereof |
| MY128323A (en) | 1996-09-30 | 2007-01-31 | Otsuka Pharma Co Ltd | Thiazole derivatives for inhibition of cytokine production and of cell adhesion |
| US6645990B2 (en) * | 2000-08-15 | 2003-11-11 | Amgen Inc. | Thiazolyl urea compounds and methods of uses |
| US6869787B2 (en) | 2002-02-27 | 2005-03-22 | The United States Of America As Represented By The Secretary Of The Army | Ricin vaccine and methods of making and using thereof |
| EP1848428A4 (en) * | 2005-02-18 | 2012-04-18 | Neurogen Corp | THIAZOLE AMIDES, IMIDAZOLE AMIDES AND RELATED ANALOGS |
| KR101081293B1 (ko) * | 2006-01-18 | 2011-11-08 | 에프. 호프만-라 로슈 아게 | 11 베타-에이치에스디1 억제제로서 티아졸 |
| EA017250B1 (ru) | 2007-07-19 | 2012-11-30 | Х. Лундбекк А/С | 5-членные гетероциклические амиды и их применение для модуляции рецептора p2x |
| TWI436767B (zh) * | 2008-03-14 | 2014-05-11 | Otsuka Pharma Co Ltd | 基質金屬蛋白酶－２（ｍｍｐ－２）及／或基質金屬蛋白酶－９（ｍｍｐ－９）抑制劑 |
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| WO2010006713A2 (de) * | 2008-07-17 | 2010-01-21 | Bayer Cropscience Ag | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| UA107791C2 (en) * | 2009-05-05 | 2015-02-25 | Dow Agrosciences Llc | Pesticidal compositions |
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| AU2011240070A1 (en) | 2010-04-16 | 2012-11-08 | Bayer Intellectual Property Gmbh | Heterocyclic compounds as pest control agents |
| PH12012502551A1 (en) | 2010-06-28 | 2017-08-23 | Bayer Ip Gmbh | Heterocyclic compounds as agents for pest control |
| WO2012007500A2 (de) | 2010-07-15 | 2012-01-19 | Bayer Cropscience Ag | Neue heterocyclische verbindungen als schädlingsbekämpfungsmittel |
| ES2775125T3 (es) | 2010-11-03 | 2020-07-23 | Dow Agrosciences Llc | Composiciones plaguicidas y procedimientos relacionados |
| WO2012109573A1 (en) * | 2011-02-11 | 2012-08-16 | Purdue Research Foundation | Substituted thiazoles for use as antiviral agents |
| EP2532661A1 (en) | 2011-06-10 | 2012-12-12 | Syngenta Participations AG | Novel insecticides |
| EP2540718A1 (en) | 2011-06-29 | 2013-01-02 | Syngenta Participations AG. | Novel insecticides |
| CA2841011A1 (en) | 2011-07-15 | 2013-01-24 | Basf Se | Pesticidal methods using substituted 3-pyridyl thiazole compounds and derivatives for combating animal pests ii |
| CA2852688C (en) | 2011-10-26 | 2021-06-29 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
| WO2013156433A1 (en) | 2012-04-17 | 2013-10-24 | Syngenta Participations Ag | Insecticidally active thiazole derivatives |
| WO2013156431A1 (en) | 2012-04-17 | 2013-10-24 | Syngenta Participations Ag | Pesticidally active pyridyl- and pyrimidyl- substituted thiazole and thiadiazole derivatives |
| US9708288B2 (en) | 2012-04-27 | 2017-07-18 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
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| EP2671881A1 (en) | 2012-06-07 | 2013-12-11 | Syngenta Participations AG. | Pesticidally active pyridyl- and pyrimidyl- substituted thiazole derivatives |
| MX2014015265A (es) | 2012-06-14 | 2015-08-12 | Basf Se | Metodos plaguicidas que utilizan compuestos de 3-piridiltiazol sustituido y derivados para combatir plagas de animales. |
| BR112015015503A2 (pt) | 2012-12-27 | 2017-07-11 | Basf Se | composto substituído, composição veterinária, utilização de um composto, método para o controle de pragas de invertebrados e para o tratamento ou proteção de um animal e material de propagação do vegetal |
| CN105636442B (zh) | 2013-10-17 | 2018-04-27 | 美国陶氏益农公司 | 制备杀虫化合物的方法 |
| CA2925595A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
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| MX2016004946A (es) | 2013-10-17 | 2016-06-28 | Dow Agrosciences Llc | Procesos para la preparacion de compuestos plaguicidas. |
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| JP2016535025A (ja) | 2013-10-22 | 2016-11-10 | ダウ アグロサイエンシィズ エルエルシー | 相乗的有害生物防除組成物および関連する方法 |
| WO2015061151A1 (en) | 2013-10-22 | 2015-04-30 | Dow Agrosciences Llc | Pesticidal compositions and related methods |
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| AR098105A1 (es) | 2013-10-22 | 2016-05-04 | Dow Agrosciences Llc | Composiciones plaguicidas y métodos relacionados |
| TW201519783A (zh) | 2013-10-22 | 2015-06-01 | Dow Agrosciences Llc | 殺蟲組成物及相關方法（四） |
| EP3060046A4 (en) | 2013-10-22 | 2017-07-26 | Dow AgroSciences LLC | Pesticidal compositions and related methods |
| TW201519772A (zh) | 2013-10-22 | 2015-06-01 | Dow Agrosciences Llc | 協同性殺蟲組成物及相關方法（四） |
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| CA2927195A1 (en) | 2013-10-22 | 2015-04-30 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
| MX2016005304A (es) | 2013-10-22 | 2017-03-01 | Dow Agrosciences Llc | Composiciones pesticidas sinergicas y metodos relacionados. |
| RU2016119368A (ru) | 2013-10-22 | 2017-11-28 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Синергетические пестицидные композиции и связанные с ними способы |
| AR098088A1 (es) | 2013-10-22 | 2016-05-04 | Dow Agrosciences Llc | Composiciones plaguicidas sinérgicas y métodos relacionados |
| AR098102A1 (es) | 2013-10-22 | 2016-05-04 | Dow Agrosciences Llc | Composiciones plaguicidas y métodos relacionados |
| AR098099A1 (es) | 2013-10-22 | 2016-05-04 | Dow Agrosciences Llc | Composiciones plaguicidas sinérgicas y los métodos relacionados |
| EP3060051A4 (en) | 2013-10-22 | 2017-04-05 | Dow AgroSciences LLC | Synergistic pesticidal compositions and related methods |
| AR100711A1 (es) * | 2014-06-05 | 2016-10-26 | Bayer Cropscience Ag | Compuestos bicíclicos como agentes para combatir parásitos |
| WO2016018442A1 (en) | 2014-07-31 | 2016-02-04 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
| JP2017523168A (ja) | 2014-07-31 | 2017-08-17 | ダウ アグロサイエンシィズ エルエルシー | ３−（３−クロロ−１ｈ−ピラゾール−１−イル）ピリジンの製造方法 |
| KR20170039121A (ko) | 2014-07-31 | 2017-04-10 | 다우 아그로사이언시즈 엘엘씨 | 3-(3-클로로-1h-피라졸-1-일)피리딘의 제조 방법 |
| US9024031B1 (en) | 2014-08-19 | 2015-05-05 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine |
| US9085552B1 (en) | 2014-09-12 | 2015-07-21 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine |
| UY36547A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
| EP3896066A3 (de) | 2015-08-07 | 2021-12-08 | Bayer CropScience Aktiengesellschaft | 2-(het)aryl-substituierte kondensierte heterocyclen-derivate als schädlingsbekämpfungsmittel |
| WO2017093180A1 (de) | 2015-12-01 | 2017-06-08 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| WO2017144341A1 (de) | 2016-02-23 | 2017-08-31 | Bayer Cropscience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| BR112019003158B1 (pt) | 2016-08-15 | 2022-10-25 | Bayer Cropscience Aktiengesellschaft | Derivados de heterociclo bicíclico condensado, seu uso, formulação agroquímica, e método para controlar pragas animais |
| CN110139853B (zh) | 2016-12-29 | 2023-06-16 | 美国陶氏益农公司 | 用于制备杀有害生物化合物的方法 |
| US10233155B2 (en) | 2016-12-29 | 2019-03-19 | Dow Agrosciences Llc | Processes for the preparation of pesticide compounds |
| TW201833107A (zh) | 2017-02-06 | 2018-09-16 | 德商拜耳廠股份有限公司 | 作為殺蟲劑之經２－（雜）芳基取代的稠合雜環衍生物 |
| CN110573513B (zh) | 2017-05-02 | 2022-08-09 | 拜耳公司 | 作为害虫防治剂的2-(杂)芳基取代的稠合双环杂环衍生物 |
| JP7290631B2 (ja) | 2017-10-04 | 2023-06-13 | バイエル・アクチエンゲゼルシヤフト | 有害生物防除剤としてのヘテロ環式化合物の誘導体 |
| US20210017193A1 (en) | 2018-03-12 | 2021-01-21 | Bayer Aktiengesellschaft | Condensed bicyclic heterocyclic derivatives as pest control agents |
| EP3820868A1 (de) | 2018-04-20 | 2021-05-19 | Bayer Aktiengesellschaft | Heterocyclen-derivate als schädlingsbekämpfungsmittel |
| CN110922399B (zh) * | 2019-11-28 | 2021-02-26 | 安徽华业香料股份有限公司 | 2-吡啶基-4-甲基噻唑-5-甲酸红没药烯酯香料的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH531518A (de) * | 1968-11-29 | 1972-12-15 | Bayer Ag | Verfahren zur Herstellung von N-substituierten Imidazolen und deren Salzen |
| US3705153A (en) * | 1969-05-14 | 1972-12-05 | Sumitomo Chemical Co | Novel thiazolyacetic acids and salts thereof |
| US3880874A (en) * | 1973-10-04 | 1975-04-29 | Syntex Inc | 2-Substituted -1,2,4-thiadiazolo-(2,3-a)benzimidazoles and process for their preparation |
-
1972
- 1972-02-02 CA CA133,761A patent/CA962269A/en not_active Expired
- 1972-05-03 BE BE782949A patent/BE782949A/xx unknown
- 1972-05-03 LU LU65289D patent/LU65289A1/xx unknown
- 1972-05-03 GB GB2061672A patent/GB1382854A/en not_active Expired
- 1972-05-03 DE DE2221647A patent/DE2221647C2/de not_active Expired
- 1972-05-04 AU AU41881/72A patent/AU469596B2/en not_active Expired
- 1972-05-04 FR FR7215901A patent/FR2135287B1/fr not_active Expired
- 1972-05-05 CH CH666872A patent/CH580097A5/xx not_active IP Right Cessation
- 1972-05-05 CH CH621276A patent/CH582700A5/xx not_active IP Right Cessation
- 1972-05-05 NL NLAANVRAGE7206075,A patent/NL177117C/xx not_active IP Right Cessation
-
1974
- 1974-03-15 US US05/451,715 patent/US4080457A/en not_active Expired - Lifetime
-
1979
- 1979-06-05 US US06/045,809 patent/US4260765A/en not_active Expired - Lifetime
-
1980
- 1980-06-04 JP JP55075388A patent/JPS5829953B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU469596B2 (en) | 1976-02-19 |
| DE2221647A1 (de) | 1972-11-09 |
| FR2135287A1 (forum.php) | 1972-12-15 |
| CH580097A5 (forum.php) | 1976-09-30 |
| NL7206075A (forum.php) | 1972-11-07 |
| US4260765A (en) | 1981-04-07 |
| NL177117C (nl) | 1985-08-01 |
| US4080457A (en) | 1978-03-21 |
| BE782949A (fr) | 1972-11-03 |
| CA962269A (en) | 1975-02-04 |
| GB1382854A (en) | 1975-02-05 |
| NL177117B (nl) | 1985-03-01 |
| LU65289A1 (forum.php) | 1972-08-23 |
| DE2221647C2 (de) | 1983-02-10 |
| AU4188172A (en) | 1973-11-08 |
| FR2135287B1 (forum.php) | 1976-08-06 |
| JPS5612386A (en) | 1981-02-06 |
| CH582700A5 (forum.php) | 1976-12-15 |
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