CN1105717C - 取代的磺酰胺基(硫代)羰基化合物 - Google Patents
取代的磺酰胺基(硫代)羰基化合物 Download PDFInfo
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- CN1105717C CN1105717C CN96199468.1A CN96199468A CN1105717C CN 1105717 C CN1105717 C CN 1105717C CN 96199468 A CN96199468 A CN 96199468A CN 1105717 C CN1105717 C CN 1105717C
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- methyl
- chlorine
- fluorine
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- -1 sulphonylamino (thio) carbonyl Chemical class 0.000 title claims abstract description 302
- 239000004009 herbicide Substances 0.000 title abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 136
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 136
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 238000000034 method Methods 0.000 claims abstract description 44
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 43
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- 150000002367 halogens Chemical group 0.000 claims abstract description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 5
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 106
- 239000000460 chlorine Substances 0.000 claims description 95
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 82
- 229910052801 chlorine Inorganic materials 0.000 claims description 82
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 78
- 239000011737 fluorine Substances 0.000 claims description 78
- 229910052731 fluorine Inorganic materials 0.000 claims description 78
- 238000002360 preparation method Methods 0.000 claims description 58
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 30
- 241000196324 Embryophyta Species 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 29
- 229910052794 bromium Inorganic materials 0.000 claims description 29
- 229940124530 sulfonamide Drugs 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 13
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 12
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 11
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 10
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 10
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 9
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- QFXZANXYUCUTQH-UHFFFAOYSA-N ethynol Chemical group OC#C QFXZANXYUCUTQH-UHFFFAOYSA-N 0.000 claims description 6
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 6
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
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- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 229950001891 iprotiazem Drugs 0.000 claims description 5
- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 claims description 4
- NRAINUFKKPBZQY-UHFFFAOYSA-N [O]C1CC1 Chemical compound [O]C1CC1 NRAINUFKKPBZQY-UHFFFAOYSA-N 0.000 claims description 4
- GYAPJISEIGCPQO-UHFFFAOYSA-N [O]C1CCC1 Chemical compound [O]C1CCC1 GYAPJISEIGCPQO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 4
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 4
- VCZIFQMEDXLHEA-UHFFFAOYSA-N cyclopentylperoxycyclohexane Chemical compound C1(CCCC1)OOC1CCCCC1 VCZIFQMEDXLHEA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 230000002363 herbicidal effect Effects 0.000 claims description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 2
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
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- 125000004414 alkyl thio group Chemical group 0.000 abstract description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
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- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
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- 125000000842 isoxazolyl group Chemical group 0.000 description 1
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- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
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- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
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- HJFQASMRSTVZLK-UHFFFAOYSA-N methyl 3-sulfamoyl-4-(trifluoromethoxy)thiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(OC(F)(F)F)C=1S(N)(=O)=O HJFQASMRSTVZLK-UHFFFAOYSA-N 0.000 description 1
- CKVFEOXONONNFR-UHFFFAOYSA-N methyl 3-sulfamoyl-4-(trifluoromethyl)thiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C(F)(F)F)C=1S(N)(=O)=O CKVFEOXONONNFR-UHFFFAOYSA-N 0.000 description 1
- CKLYAVRVZCPTBT-UHFFFAOYSA-N methyl 4-bromo-3-sulfamoylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(Br)C=1S(N)(=O)=O CKLYAVRVZCPTBT-UHFFFAOYSA-N 0.000 description 1
- AXMCHITYDGRMCW-UHFFFAOYSA-N methyl 4-chloro-3-sulfamoylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(Cl)C=1S(N)(=O)=O AXMCHITYDGRMCW-UHFFFAOYSA-N 0.000 description 1
- FGCLGOMCOYDCGH-UHFFFAOYSA-N methyl 4-ethyl-3-sulfamoylthiophene-2-carboxylate Chemical compound CCC1=CSC(C(=O)OC)=C1S(N)(=O)=O FGCLGOMCOYDCGH-UHFFFAOYSA-N 0.000 description 1
- GSNVXCRBJHYECU-UHFFFAOYSA-N methyl 4-fluoro-3-sulfamoylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(F)C=1S(N)(=O)=O GSNVXCRBJHYECU-UHFFFAOYSA-N 0.000 description 1
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- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 150000002751 molybdenum Chemical class 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
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- 125000006606 n-butoxy group Chemical group 0.000 description 1
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- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
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- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 235000015320 potassium carbonate Nutrition 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- DQLXRFVOPFWJCD-UHFFFAOYSA-N propan-2-yl 3-amino-4-chlorothiophene-2-carboxylate Chemical compound CC(C)OC(=O)C=1SC=C(Cl)C=1N DQLXRFVOPFWJCD-UHFFFAOYSA-N 0.000 description 1
- LJDCAYQRXOHHAO-UHFFFAOYSA-N propan-2-yl 3-amino-4-chlorothiophene-2-carboxylate;hydrochloride Chemical compound Cl.CC(C)OC(=O)C=1SC=C(Cl)C=1N LJDCAYQRXOHHAO-UHFFFAOYSA-N 0.000 description 1
- ZXMQWAFNUZEZIH-UHFFFAOYSA-N propan-2-yl 3-amino-4-methylthiophene-2-carboxylate Chemical compound CC(C)OC(=O)C=1SC=C(C)C=1N ZXMQWAFNUZEZIH-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- AJAMNMBRLVAPHU-UHFFFAOYSA-N propyl 3-(trifluoromethoxy)benzoate sulfuryl dichloride Chemical compound S(=O)(=O)(Cl)Cl.FC(OC1=CC=CC(=C1)C(=O)OCCC)(F)F AJAMNMBRLVAPHU-UHFFFAOYSA-N 0.000 description 1
- PPTXVSVKUVLIEH-UHFFFAOYSA-N propyl 4-methyl-3-sulfamoylthiophene-2-carboxylate Chemical compound CCCOC(=O)C=1SC=C(C)C=1S(N)(=O)=O PPTXVSVKUVLIEH-UHFFFAOYSA-N 0.000 description 1
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- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
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- 230000002940 repellent Effects 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
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- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000009955 starching Methods 0.000 description 1
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- 239000004575 stone Substances 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Abstract
Description
制备实施例的活性化合物 | 应用比例(gof ai./ha) | 玉米属 | 大豆属 | 毒麦属 | 早熟禾属 | 高粱属 | 豚草属 | 母菊属 | 茄属 |
5167891012131617181920212223283031 | 3030125606012525012512530306060125125125125603015 | 010003000030--1001002000010 | 20--00-200-000000100--- | 95959595958080809095808095959595-959595 | 959595-90809080809595959595959580959595 | 909095958060706070906090-90958060958080 | 9595959590959595959595959595959590959595 | 9595959595909595959595959595959595959595 | 959595-95959595909595959095959590959595 |
制备实施例的活性化合物 | 应用比例(gofai./ha) | 玉米属 | 大豆属 | 毒麦属 | 早熟禾属 | 高粱属 | 豚草属 | 母菊属 | 茄属 |
323334353738394041424344454647485153545556 | 601256060606060606060608125812512512512530125125 | 2010100100010010-30100103000010- | 20-0-10-2030-1010020-102030---0 | 95-609590959590609595959080909580959510060 | 959070957070909580959595959590958095959080 | 60808095-60--60-8095-8060-80-8060- | 95909095809595959595959595959595959595100- | 9595951009595709595959595909595100959595100100 | 9595909590959095909595959595959595959510095 |
制备实施例的活性化合物 | 应用比例(gofai./ha) | 玉米属 | 大豆属 | 毒麦属 | 早熟禾属 | 高粱属 | 豚草属 | 母菊属 | 茄属 |
57585961626364656667687072767780818284858689 | 601251251251256060125125601256012560601256060125125125125 | 0200001010200051010000-0560100 | ------30---10--30----30-40- | 95801009580100908010010080909095959510060959580100 | 9595709590956080--909070--------- | 95--806080-801009060--959090959090957090 | --95100-100100---959095--------- | 9510010095951001009510010010010010010010010010010095100100100 | 9595959595100100951001009510010095909510010010010095100 |
制备实施例的活性化合物 | 应用比例(gofai./ha) | 玉米属 | 大豆属 | 毒麦属 | 早熟禾属 | 高粱属 | 豚草属 | 母菊属 | 茄属 |
931081211291301311341351361401411421431441453146147148149150 | 60125500250250250500125125301515601256060601560125125 | 0510101000-30-302020-010030400- | ---1000204020100100-02010003010 | 909070959595959595-9095909095908095809580 | ---959590909595958080909095709090959590 | 8095809080907090909580-909595---908080 | ---609595809080809080808095808070809570 | 959590909580909090808080-9560958070809580 | 909095959595959595959080909595809080959580 |
制备实施例的活性化合物 | 应用比例(gofai./ha) | 玉米属 | 大豆属 | 毒麦属 | 早熟禾属 | 高粱属 | 豚草属 | 母菊属 | 茄属 |
151152153154155156157158159160161162163164165166167172 | 151251256060606030306060604881560125 | 20-00-001010300-2020040-- | 1020300401020--102000010-3060 | 9095-9595709095909095958095-908090 | 909595959590809595909595959590909595 | 5095-95957080606060-90609070709590 | 8095957090709595959095808010080809090 | 9080707080951009595959595-7090959595 | 909595909570909595909595909580909095 |
制备实施例的活性化合物 | 应用比例(gofai./ha) | 玉米属 | 马唐属 | 稗属 | 毒麦属 | 高粱属 | 苋属 | Gal-lium | 母菊属 | 紧缕属 |
51672830313238445463140141144151159162163 | 301254006060603060606060602503025030606060 | 106020151015570105030--10-60--60 | 95959095909095707060-5095709590607080 | 809595958070951009090959090909570808070 | 7090959560609070-709570--7060609080 | 9095801009595809595100958095909590708095 | 100100100-100100100951001001001001001001009595-100 | --909580858070-9585909590959095-95 | 951001009590100100809595100959070709010060100 | 90100100100100100959095-100100709595901009095 |
制备实施例的活性化合物 | 应用比例(gofai./ha) | 玉米属 | 马唐属 | 稗属 | 毒麦属 | 高粱属 | 苋属 | Gal、lium | 母菊属 | 繁缕属 |
164165166 | 606060 | --- | 605070 | 808070 | 705050 | 959090 | 1009595 | 909595 | 10095100 | 959595 |
Claims (9)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE19540737.7 | 1995-11-02 | ||
DE19540737A DE19540737A1 (de) | 1995-11-02 | 1995-11-02 | Substituierte Sulfonylamino(thio)carbonylverbindungen |
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CN02104506.2A Division CN1232505C (zh) | 1995-11-02 | 2002-02-07 | 取代的磺酰胺基(硫代)羰基化合物 |
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CN1207099A CN1207099A (zh) | 1999-02-03 |
CN1105717C true CN1105717C (zh) | 2003-04-16 |
Family
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CN96199468.1A Expired - Lifetime CN1105717C (zh) | 1995-11-02 | 1996-10-21 | 取代的磺酰胺基(硫代)羰基化合物 |
CN02104506.2A Expired - Lifetime CN1232505C (zh) | 1995-11-02 | 2002-02-07 | 取代的磺酰胺基(硫代)羰基化合物 |
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CN02104506.2A Expired - Lifetime CN1232505C (zh) | 1995-11-02 | 2002-02-07 | 取代的磺酰胺基(硫代)羰基化合物 |
Country Status (11)
Country | Link |
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US (3) | US6180567B1 (zh) |
EP (1) | EP0859774B1 (zh) |
JP (1) | JP4082728B2 (zh) |
CN (2) | CN1105717C (zh) |
AU (1) | AU7490996A (zh) |
BR (1) | BR9611129A (zh) |
CA (1) | CA2236208C (zh) |
DE (2) | DE19540737A1 (zh) |
HU (1) | HUP9802995A3 (zh) |
PL (1) | PL186726B1 (zh) |
WO (1) | WO1997016449A1 (zh) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
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DE19650196A1 (de) | 1996-12-04 | 1998-06-10 | Bayer Ag | Thienylsulfonylamino(thio)carbonylverbindungen |
DE19933260A1 (de) | 1999-07-15 | 2001-01-18 | Bayer Ag | Substituierte Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)one |
AR037097A1 (es) * | 2001-10-05 | 2004-10-20 | Novartis Ag | Compuestos acilsulfonamidas, composiciones farmaceuticas y el uso de dichos compuestos para la preparacion de un medicamento |
DE10154074A1 (de) | 2001-11-02 | 2003-05-15 | Bayer Cropscience Ag | Substituierte Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)one |
DE102004010812A1 (de) * | 2004-03-05 | 2005-09-22 | Bayer Cropscience Ag | Unkrautbekämpfungsverfahren |
ES2594874T3 (es) * | 2004-11-18 | 2016-12-23 | Synta Pharmaceuticals Corp. | Compuestos de triazol que modulan la actividad de HSP90 |
DE102004063192A1 (de) * | 2004-12-29 | 2006-07-13 | Bayer Cropscience Ag | Verfahren zur Herstellung von substituierten Thiophensulfonylisocyanaten |
EP1717228A1 (de) | 2005-04-28 | 2006-11-02 | Bayer CropScience GmbH | Sulfonylamino(thio)carbonylverbindungen als Herbizide oder Pflanzenwachstumsregulatoren |
JP5118039B2 (ja) | 2005-08-18 | 2013-01-16 | シンタ ファーマシューティカルズ コーポレーション | Hsp90活性を調節するトリアゾール化合物 |
AU2007267852A1 (en) * | 2006-05-25 | 2007-12-06 | Synta Pharmaceuticals Corp. | Compounds that modulate Hsp90 activity and methods for identifying same |
DE102006032164A1 (de) * | 2006-07-12 | 2008-01-24 | Bayer Cropscience Ag | Substituierte Furyl-sulfonylamino(thio)carbonyl-triazolin(thi)one |
AU2008312624B2 (en) | 2007-10-18 | 2014-07-10 | Boehringer Ingelheim International Gmbh | Preparation of dihydrothieno [3, 2-D] pyrimidines and intermediates used therein |
WO2011133520A1 (en) | 2010-04-19 | 2011-10-27 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a hsp90 inhibitory compounds and a egfr inhibitor |
AU2012332421A1 (en) | 2011-11-02 | 2014-06-05 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of Hsp90 inhibitors with topoisomerase I inhibitors |
AU2012332424A1 (en) | 2011-11-02 | 2014-06-05 | Synta Pharmaceuticals Corp. | Combination therapy of Hsp90 inhibitors with platinum-containing agents |
US9402831B2 (en) | 2011-11-14 | 2016-08-02 | Synta Pharmaceutical Corp. | Combination therapy of HSP90 inhibitors with BRAF inhibitors |
JP2016128386A (ja) * | 2013-04-23 | 2016-07-14 | 石原産業株式会社 | ヘテロアリールスルホンアミド系化合物又はその塩 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4877440A (en) | 1985-05-29 | 1989-10-31 | E. I. Du Pont De Nemours And Company | Thiophenesulfonamide herbicides |
DE3815765A1 (de) | 1988-05-09 | 1989-11-23 | Bayer Ag | 2-sulfonylaminocarbonyl-2,4-dihydro-3h-1,2,4- triazol-3-one einschliesslich 4,5-kondensierter, bicyclischer derivate, verfahren und neue zwischenprodukte zu ihrer herstellung und ihre verwendung als pflanzenbehandlungsmittel |
DE3936623A1 (de) * | 1989-11-03 | 1991-05-08 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit ueber schwefel gebundenen substituenten |
US5085684A (en) | 1988-05-09 | 1992-02-04 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur |
AT390060B (de) * | 1988-05-02 | 1990-03-12 | Cl Pharma | Verfahren zur herstellung von 5-chlor-3chlorsulfonyl-2-thiophencarbonsaeureestern |
US5300480A (en) | 1989-04-13 | 1994-04-05 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having two substituents bonded via oxygen |
US5241074A (en) * | 1988-05-09 | 1993-08-31 | Bayer Aktiengesellschaft | Sulphonylaminocarbonyltriazolinones |
DE4131842A1 (de) * | 1991-09-25 | 1993-04-01 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit zwei ueber sauerstoff gebundenen substituenten |
DE4110795A1 (de) * | 1991-04-04 | 1992-10-08 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit ueber sauerstoff gebundenen substituenten |
US5057144A (en) | 1988-05-09 | 1991-10-15 | Bayer Aktiengesellschaft | Sulphonylaminocarbonyltriazolinones |
DE4215878A1 (de) | 1992-05-14 | 1993-11-18 | Bayer Ag | Sulfonylierte Carbonsäureamide |
US5256632A (en) | 1990-05-30 | 1993-10-26 | Bayer Aktiengesellschaft | Herbicidal sulphonylated carboxamides |
DE4029753A1 (de) * | 1990-09-20 | 1992-03-26 | Basf Ag | Sulfonamide |
US5534486A (en) | 1991-04-04 | 1996-07-09 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen |
NZ247440A (en) | 1992-05-06 | 1995-04-27 | Squibb & Sons Inc | Phenyl sulphonamide derivatives, preparation and pharmaceutical compositions thereof |
-
1995
- 1995-11-02 DE DE19540737A patent/DE19540737A1/de not_active Withdrawn
-
1996
- 1996-10-21 AU AU74909/96A patent/AU7490996A/en not_active Abandoned
- 1996-10-21 BR BR9611129A patent/BR9611129A/pt not_active IP Right Cessation
- 1996-10-21 WO PCT/EP1996/004559 patent/WO1997016449A1/de active IP Right Grant
- 1996-10-21 DE DE59609032T patent/DE59609032D1/de not_active Expired - Lifetime
- 1996-10-21 JP JP51702897A patent/JP4082728B2/ja not_active Expired - Lifetime
- 1996-10-21 US US09/066,385 patent/US6180567B1/en not_active Expired - Lifetime
- 1996-10-21 PL PL96327978A patent/PL186726B1/pl not_active IP Right Cessation
- 1996-10-21 CA CA002236208A patent/CA2236208C/en not_active Expired - Fee Related
- 1996-10-21 CN CN96199468.1A patent/CN1105717C/zh not_active Expired - Lifetime
- 1996-10-21 EP EP96937202A patent/EP0859774B1/de not_active Expired - Lifetime
- 1996-10-21 HU HU9802995A patent/HUP9802995A3/hu unknown
-
2000
- 2000-11-09 US US09/710,079 patent/US6441195B1/en not_active Expired - Lifetime
-
2002
- 2002-02-07 CN CN02104506.2A patent/CN1232505C/zh not_active Expired - Lifetime
- 2002-05-01 US US10/137,088 patent/US20030162979A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
EP0859774B1 (de) | 2002-04-03 |
JPH11515018A (ja) | 1999-12-21 |
BR9611129A (pt) | 1999-03-30 |
EP0859774A1 (de) | 1998-08-26 |
PL186726B1 (pl) | 2004-02-27 |
CN1439631A (zh) | 2003-09-03 |
DE19540737A1 (de) | 1997-05-07 |
AU7490996A (en) | 1997-05-22 |
CN1232505C (zh) | 2005-12-21 |
US20030162979A1 (en) | 2003-08-28 |
CA2236208C (en) | 2005-05-03 |
JP4082728B2 (ja) | 2008-04-30 |
US6180567B1 (en) | 2001-01-30 |
WO1997016449A1 (de) | 1997-05-09 |
PL327978A1 (en) | 1999-01-04 |
CN1207099A (zh) | 1999-02-03 |
CA2236208A1 (en) | 1997-05-09 |
DE59609032D1 (de) | 2002-05-08 |
HUP9802995A2 (hu) | 1999-03-29 |
US6441195B1 (en) | 2002-08-27 |
HUP9802995A3 (en) | 1999-04-28 |
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