JPH0141633B2 - - Google Patents
Info
- Publication number
- JPH0141633B2 JPH0141633B2 JP56162112A JP16211281A JPH0141633B2 JP H0141633 B2 JPH0141633 B2 JP H0141633B2 JP 56162112 A JP56162112 A JP 56162112A JP 16211281 A JP16211281 A JP 16211281A JP H0141633 B2 JPH0141633 B2 JP H0141633B2
- Authority
- JP
- Japan
- Prior art keywords
- halogen
- optionally
- alkyl
- substituted
- methyl
- 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
- -1 cyano, nitro, amino Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 238000003756 stirring Methods 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- PNEABRNAYDDYJK-UHFFFAOYSA-N 2-hydroxy-n-methyl-n-phenylacetamide Chemical compound OCC(=O)N(C)C1=CC=CC=C1 PNEABRNAYDDYJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 125000005109 alkynylthio group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- FPIURKVYZFPGJO-UHFFFAOYSA-N [2-(n-methylanilino)-2-oxoethyl] acetate Chemical compound CC(=O)OCC(=O)N(C)C1=CC=CC=C1 FPIURKVYZFPGJO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 1
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical group OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000000094 2-phenylethyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 239000011593 sulfur Chemical group 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- JOXBFDPBVQGJOJ-UHFFFAOYSA-N 2,5-dichloro-1,3-benzoxazole Chemical compound ClC1=CC=C2OC(Cl)=NC2=C1 JOXBFDPBVQGJOJ-UHFFFAOYSA-N 0.000 description 2
- OPQIOIYLAKHILI-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yloxy)acetic acid Chemical compound C1=CC=C2SC(OCC(=O)O)=NC2=C1 OPQIOIYLAKHILI-UHFFFAOYSA-N 0.000 description 2
- XKFYEXBWNAKEGV-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yloxy)-n-methyl-n-phenylacetamide Chemical compound N=1C2=CC=CC=C2OC=1OCC(=O)N(C)C1=CC=CC=C1 XKFYEXBWNAKEGV-UHFFFAOYSA-N 0.000 description 2
- DRLMMVPCYXFPEP-UHFFFAOYSA-N 2-bromo-1,3-benzothiazole Chemical compound C1=CC=C2SC(Br)=NC2=C1 DRLMMVPCYXFPEP-UHFFFAOYSA-N 0.000 description 2
- BBVQDWDBTWSGHQ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole Chemical group C1=CC=C2OC(Cl)=NC2=C1 BBVQDWDBTWSGHQ-UHFFFAOYSA-N 0.000 description 2
- JNQVLKWNKVMFBN-UHFFFAOYSA-N 2-hydroxy-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CO JNQVLKWNKVMFBN-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- UNIJBMUBHBAUET-UHFFFAOYSA-N 3-(methylamino)propanenitrile Chemical compound CNCCC#N UNIJBMUBHBAUET-UHFFFAOYSA-N 0.000 description 2
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229960004275 glycolic acid Drugs 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 235000012254 magnesium hydroxide Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical class 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 description 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- WZWJYKCTJZQQOC-UHFFFAOYSA-N 2,2-dimethyl-1,3,3a,4,5,6,7,7a-octahydroindole Chemical compound C1CCCC2NC(C)(C)CC21 WZWJYKCTJZQQOC-UHFFFAOYSA-N 0.000 description 1
- PDELQDSYLBLPQO-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indole Chemical compound C1CCCC2NCCC21 PDELQDSYLBLPQO-UHFFFAOYSA-N 0.000 description 1
- FJFUFOZWRAHFOP-UHFFFAOYSA-N 2,4,5-trichloro-1,3-oxazole Chemical compound ClC1=NC(Cl)=C(Cl)O1 FJFUFOZWRAHFOP-UHFFFAOYSA-N 0.000 description 1
- MRPXVCUBQINJCC-UHFFFAOYSA-N 2,4,6,7-tetrachloro-1,3-benzothiazole Chemical compound C1=C(Cl)C(Cl)=C2SC(Cl)=NC2=C1Cl MRPXVCUBQINJCC-UHFFFAOYSA-N 0.000 description 1
- SLFJWTBVEMHUTL-UHFFFAOYSA-N 2-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]acetic acid Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)S1 SLFJWTBVEMHUTL-UHFFFAOYSA-N 0.000 description 1
- KJKQOIBFCKHLHH-UHFFFAOYSA-N 2-bromo-1,3,4-oxadiazole Chemical compound BrC1=NN=CO1 KJKQOIBFCKHLHH-UHFFFAOYSA-N 0.000 description 1
- ZMSUVHHASUJZNH-UHFFFAOYSA-N 2-bromo-1,3-benzoxazole Chemical compound C1=CC=C2OC(Br)=NC2=C1 ZMSUVHHASUJZNH-UHFFFAOYSA-N 0.000 description 1
- YCHPNSOKVRTPES-UHFFFAOYSA-N 2-bromo-1,3-oxazole Chemical class BrC1=NC=CO1 YCHPNSOKVRTPES-UHFFFAOYSA-N 0.000 description 1
- XMTNHCRGHQLOEX-UHFFFAOYSA-N 2-bromo-5-phenyl-1,3,4-oxadiazole Chemical compound O1C(Br)=NN=C1C1=CC=CC=C1 XMTNHCRGHQLOEX-UHFFFAOYSA-N 0.000 description 1
- NVQXBSUUWVZRCA-UHFFFAOYSA-N 2-bromo-5-phenyl-1,3,4-thiadiazole Chemical compound S1C(Br)=NN=C1C1=CC=CC=C1 NVQXBSUUWVZRCA-UHFFFAOYSA-N 0.000 description 1
- ZNDGPDKYFJXEPS-UHFFFAOYSA-N 2-chloro-1,3,4-oxadiazole Chemical compound ClC1=NN=CO1 ZNDGPDKYFJXEPS-UHFFFAOYSA-N 0.000 description 1
- YXXCZHJSELQADZ-UHFFFAOYSA-N 2-chloro-1,3-benzoxazole-5-carbonitrile Chemical compound N#CC1=CC=C2OC(Cl)=NC2=C1 YXXCZHJSELQADZ-UHFFFAOYSA-N 0.000 description 1
- LZXONCQHRWRSKB-UHFFFAOYSA-N 2-chloro-4,6-difluoro-1,3-benzothiazole Chemical compound FC1=CC(F)=C2N=C(Cl)SC2=C1 LZXONCQHRWRSKB-UHFFFAOYSA-N 0.000 description 1
- VEYHSBGVRVKUMZ-UHFFFAOYSA-N 2-chloro-4-methyl-5-phenylsulfanyl-1,3-oxazole Chemical compound N1=C(Cl)OC(SC=2C=CC=CC=2)=C1C VEYHSBGVRVKUMZ-UHFFFAOYSA-N 0.000 description 1
- LDHMGRLVVVPORL-UHFFFAOYSA-N 2-chloro-5-(trifluoromethoxy)-1,3-benzothiazole Chemical compound FC(F)(F)OC1=CC=C2SC(Cl)=NC2=C1 LDHMGRLVVVPORL-UHFFFAOYSA-N 0.000 description 1
- AVJUFHRBOJNDFG-UHFFFAOYSA-N 2-chloro-5-methyl-1,3-benzoxazole Chemical compound CC1=CC=C2OC(Cl)=NC2=C1 AVJUFHRBOJNDFG-UHFFFAOYSA-N 0.000 description 1
- BSHJRTMGKFPQGZ-UHFFFAOYSA-N 2-chloro-5-nitro-1,3-benzothiazole Chemical compound [O-][N+](=O)C1=CC=C2SC(Cl)=NC2=C1 BSHJRTMGKFPQGZ-UHFFFAOYSA-N 0.000 description 1
- JDESVZPWUYUPRC-UHFFFAOYSA-N 2-chloro-5-nitro-1,3-benzoxazole Chemical compound [O-][N+](=O)C1=CC=C2OC(Cl)=NC2=C1 JDESVZPWUYUPRC-UHFFFAOYSA-N 0.000 description 1
- QSGNNXKJPIMRPO-UHFFFAOYSA-N 2-chloro-5-phenyl-1,3,4-oxadiazole Chemical compound O1C(Cl)=NN=C1C1=CC=CC=C1 QSGNNXKJPIMRPO-UHFFFAOYSA-N 0.000 description 1
- ASSPGHHANNDMET-UHFFFAOYSA-N 2-chloro-5-phenyl-1,3,4-thiadiazole Chemical compound S1C(Cl)=NN=C1C1=CC=CC=C1 ASSPGHHANNDMET-UHFFFAOYSA-N 0.000 description 1
- YIRRVMGAKFESLR-UHFFFAOYSA-N 2-chloro-6-(trifluoromethyl)-1,3-benzothiazole Chemical compound FC(F)(F)C1=CC=C2N=C(Cl)SC2=C1 YIRRVMGAKFESLR-UHFFFAOYSA-N 0.000 description 1
- OJRYLNVGOPEAEP-UHFFFAOYSA-N 2-chloro-6-ethoxy-1,3-benzothiazole Chemical compound CCOC1=CC=C2N=C(Cl)SC2=C1 OJRYLNVGOPEAEP-UHFFFAOYSA-N 0.000 description 1
- KUCSJGBXJBQHNI-UHFFFAOYSA-N 2-chloro-6-nitro-1,3-benzothiazole Chemical compound [O-][N+](=O)C1=CC=C2N=C(Cl)SC2=C1 KUCSJGBXJBQHNI-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 description 1
- IBZKBSXREAQDTO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)ethanamine Chemical compound COCCNCCOC IBZKBSXREAQDTO-UHFFFAOYSA-N 0.000 description 1
- ZJHBAERTGJSGHX-UHFFFAOYSA-N 2-methyl-2,3,3a,4,5,6,7,7a-octahydro-1h-indole Chemical compound C1CCCC2NC(C)CC21 ZJHBAERTGJSGHX-UHFFFAOYSA-N 0.000 description 1
- LHYOQKQVMYTNLB-UHFFFAOYSA-N 2-methyl-5-nitro-n-propan-2-ylaniline Chemical compound CC(C)NC1=CC([N+]([O-])=O)=CC=C1C LHYOQKQVMYTNLB-UHFFFAOYSA-N 0.000 description 1
- DVYYELCTUUTAIE-UHFFFAOYSA-N 2-methyl-N-(2-methylpropyl)-5-nitroaniline Chemical compound CC(C)CNC1=CC([N+]([O-])=O)=CC=C1C DVYYELCTUUTAIE-UHFFFAOYSA-N 0.000 description 1
- MEQMSOHGNAUBMS-UHFFFAOYSA-N 3,5-dichloro-1,2,4-oxadiazole Chemical compound ClC1=NOC(Cl)=N1 MEQMSOHGNAUBMS-UHFFFAOYSA-N 0.000 description 1
- KKLNIFRDDPNIDO-UHFFFAOYSA-N 3-chloro-4-propan-2-yl-1,2,5-thiadiazole Chemical compound CC(C)C1=NSN=C1Cl KKLNIFRDDPNIDO-UHFFFAOYSA-N 0.000 description 1
- KLWDPIXDUVYHMS-UHFFFAOYSA-N 4-chloro-n-ethylaniline Chemical compound CCNC1=CC=C(Cl)C=C1 KLWDPIXDUVYHMS-UHFFFAOYSA-N 0.000 description 1
- XCEYKKJMLOFDSS-UHFFFAOYSA-N 4-chloro-n-methylaniline Chemical compound CNC1=CC=C(Cl)C=C1 XCEYKKJMLOFDSS-UHFFFAOYSA-N 0.000 description 1
- PKLDFALGUIOLDX-UHFFFAOYSA-N 4-chloro-n-propylaniline Chemical compound CCCNC1=CC=C(Cl)C=C1 PKLDFALGUIOLDX-UHFFFAOYSA-N 0.000 description 1
- WZWNIVYQWJRDQX-UHFFFAOYSA-N 4-methyl-n-(2-methylpropyl)aniline Chemical compound CC(C)CNC1=CC=C(C)C=C1 WZWNIVYQWJRDQX-UHFFFAOYSA-N 0.000 description 1
- OMQZTBCIXIXKBF-UHFFFAOYSA-N 4-methyl-n-propan-2-ylaniline Chemical compound CC(C)NC1=CC=C(C)C=C1 OMQZTBCIXIXKBF-UHFFFAOYSA-N 0.000 description 1
- YPEZCZIRPXYWSI-UHFFFAOYSA-N 4-methyl-n-propylaniline Chemical compound CCCNC1=CC=C(C)C=C1 YPEZCZIRPXYWSI-UHFFFAOYSA-N 0.000 description 1
- DHELIGKVOGTMGF-UHFFFAOYSA-N 5-chloro-1-phenyltetrazole Chemical compound ClC1=NN=NN1C1=CC=CC=C1 DHELIGKVOGTMGF-UHFFFAOYSA-N 0.000 description 1
- FUFPQUVFXPFEHA-UHFFFAOYSA-N 5-chloro-3-ethyl-4-phenyl-1,2-oxazole Chemical compound CCC1=NOC(Cl)=C1C1=CC=CC=C1 FUFPQUVFXPFEHA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- CKWHMZUXQGTPQY-UHFFFAOYSA-N diethyl 4-bromo-1,2-oxazole-3,5-dicarboxylate Chemical compound CCOC(=O)C1=NOC(C(=O)OCC)=C1Br CKWHMZUXQGTPQY-UHFFFAOYSA-N 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 229940047889 isobutyramide Drugs 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- BJHFAGGWTZURFX-UHFFFAOYSA-N n,2-dimethyl-5-nitroaniline Chemical compound CNC1=CC([N+]([O-])=O)=CC=C1C BJHFAGGWTZURFX-UHFFFAOYSA-N 0.000 description 1
- QCIFLGSATTWUQJ-UHFFFAOYSA-N n,4-dimethylaniline Chemical compound CNC1=CC=C(C)C=C1 QCIFLGSATTWUQJ-UHFFFAOYSA-N 0.000 description 1
- PHCGSXNKSVJPAG-UHFFFAOYSA-N n-(2-ethoxyethoxy)-n-hexan-2-yl-2-hydroxyacetamide Chemical compound CCCCC(C)N(C(=O)CO)OCCOCC PHCGSXNKSVJPAG-UHFFFAOYSA-N 0.000 description 1
- YGBYFDPEECMAJJ-UHFFFAOYSA-N n-(2-methylpropyl)naphthalen-2-amine Chemical compound C1=CC=CC2=CC(NCC(C)C)=CC=C21 YGBYFDPEECMAJJ-UHFFFAOYSA-N 0.000 description 1
- YBWLHYNAKLSSRV-UHFFFAOYSA-N n-(5-chloro-1,3,4-oxadiazol-2-yl)-n,2,2-trimethylpropanamide Chemical compound CC(C)(C)C(=O)N(C)C1=NN=C(Cl)O1 YBWLHYNAKLSSRV-UHFFFAOYSA-N 0.000 description 1
- HIPXPABRMMYVQD-UHFFFAOYSA-N n-benzylbutan-1-amine Chemical compound CCCCNCC1=CC=CC=C1 HIPXPABRMMYVQD-UHFFFAOYSA-N 0.000 description 1
- NPKKGGAJLKNQDY-UHFFFAOYSA-N n-butyl-4-chloroaniline Chemical compound CCCCNC1=CC=C(Cl)C=C1 NPKKGGAJLKNQDY-UHFFFAOYSA-N 0.000 description 1
- FPHFMZTUFVNDQL-UHFFFAOYSA-N n-butyl-4-methylaniline Chemical compound CCCCNC1=CC=C(C)C=C1 FPHFMZTUFVNDQL-UHFFFAOYSA-N 0.000 description 1
- FFWIPAKZSVGWDP-UHFFFAOYSA-N n-butylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(NCCCC)=CC=C21 FFWIPAKZSVGWDP-UHFFFAOYSA-N 0.000 description 1
- JGBJNRPKVSUFSM-UHFFFAOYSA-N n-ethyl-2-methyl-5-nitroaniline Chemical compound CCNC1=CC([N+]([O-])=O)=CC=C1C JGBJNRPKVSUFSM-UHFFFAOYSA-N 0.000 description 1
- AASABFUMCBTXRL-UHFFFAOYSA-N n-ethyl-4-methylaniline Chemical compound CCNC1=CC=C(C)C=C1 AASABFUMCBTXRL-UHFFFAOYSA-N 0.000 description 1
- KDFFXYVOTKKBDI-UHFFFAOYSA-N n-ethylnaphthalen-1-amine Chemical compound C1=CC=C2C(NCC)=CC=CC2=C1 KDFFXYVOTKKBDI-UHFFFAOYSA-N 0.000 description 1
- AHEJURHRYJPYST-UHFFFAOYSA-N n-ethylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(NCC)=CC=C21 AHEJURHRYJPYST-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- KKTBUCVHSCATGB-UHFFFAOYSA-N n-methylcyclopentanamine Chemical compound CNC1CCCC1 KKTBUCVHSCATGB-UHFFFAOYSA-N 0.000 description 1
- AKEYUWUEAXIBTF-UHFFFAOYSA-N n-methylnaphthalen-1-amine Chemical compound C1=CC=C2C(NC)=CC=CC2=C1 AKEYUWUEAXIBTF-UHFFFAOYSA-N 0.000 description 1
- IJNQJQRKLLCLMC-UHFFFAOYSA-N n-methylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(NC)=CC=C21 IJNQJQRKLLCLMC-UHFFFAOYSA-N 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- SIZAEFGOHCBUPV-UHFFFAOYSA-N n-propan-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(NC(C)C)=CC=C21 SIZAEFGOHCBUPV-UHFFFAOYSA-N 0.000 description 1
- KEFWNHAJKUZOOG-UHFFFAOYSA-N n-propylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(NCCC)=CC=C21 KEFWNHAJKUZOOG-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- SDSMZSUWTYFEBO-UHFFFAOYSA-M tributyl(methyl)phosphanium;bromide Chemical compound [Br-].CCCC[P+](C)(CCCC)CCCC SDSMZSUWTYFEBO-UHFFFAOYSA-M 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only 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
- A01N43/74—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
-
- 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
- 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
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
-
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803038636 DE3038636A1 (de) | 1980-10-13 | 1980-10-13 | Verfahren zur herstellung von substituierten oxyessigsaeureamiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5793969A JPS5793969A (en) | 1982-06-11 |
| JPH0141633B2 true JPH0141633B2 (enrdf_load_stackoverflow) | 1989-09-06 |
Family
ID=6114277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56162112A Granted JPS5793969A (en) | 1980-10-13 | 1981-10-13 | Manufacture of substituted oxyacetic acid amide |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5793969A (enrdf_load_stackoverflow) |
| DE (1) | DE3038636A1 (enrdf_load_stackoverflow) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3038652A1 (de) * | 1980-10-13 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | 5-chlor-benzoxazol-2-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3038599A1 (de) * | 1980-10-13 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | Substituierte benzazol-2-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3148839A1 (de) * | 1981-12-10 | 1983-06-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hetaryloxyacetamiden |
| DE3228147A1 (de) * | 1982-07-28 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Substituierte 3-trihalogenmethyl-1,2,4-thiadiazol-5-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3228131A1 (de) * | 1982-07-28 | 1984-02-02 | Bayer Ag, 5090 Leverkusen | Substituierte 3-trichlormethyl-1,2,4-thiadiazol-5-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3228132A1 (de) * | 1982-07-28 | 1984-02-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von substituierten thiadiazolyloxyacetamiden |
| DE3422861A1 (de) * | 1984-06-20 | 1986-01-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von heteroaryloxyacetamiden |
| DE3505902A1 (de) * | 1985-02-21 | 1986-08-21 | Bayer Ag, 5090 Leverkusen | 4,5-disubstituierte 1,3-thiazol-2-yloxyacetamide |
| NZ225999A (en) * | 1987-09-10 | 1992-04-28 | Merck Sharp & Dohme | Azacyclic- or azabicyclic-substituted thiadiazole derivatives and pharmaceutical compositions |
| DE3821600A1 (de) | 1988-06-27 | 1989-12-28 | Bayer Ag | Heteroaryloxyessigsaeure-n-isopropylanilide |
| CN107033102B (zh) * | 2017-05-02 | 2019-07-05 | 江苏永凯化学有限公司 | 苯噻酰草胺的合成方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL37111A0 (en) * | 1970-06-23 | 1971-08-25 | Agripat Sa | New 2-aminoalkoxy-4-phenyl-thiazoles and their addition salts |
| EP0005501B1 (de) * | 1978-05-20 | 1981-11-25 | Bayer Ag | Heteroaryl-oxyessigsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| DE2903966A1 (de) * | 1979-02-02 | 1980-08-07 | Bayer Ag | Substituierte carbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE2822155A1 (de) * | 1978-05-20 | 1979-11-22 | Bayer Ag | Substituierte carbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE2914003A1 (de) * | 1979-04-06 | 1980-10-16 | Bayer Ag | Azolyloxy-carbonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| EP0018497B1 (de) * | 1979-04-06 | 1982-04-28 | Bayer Ag | Azolyloxy-essigsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| DE3004326A1 (de) * | 1980-02-06 | 1981-08-13 | Bayer Ag, 5090 Leverkusen | Azolyloxy-carbonsaeureamide, verfahren zu ihrer herstellung un ihre verwendung als herbinzide |
| DE2946524A1 (de) * | 1979-11-17 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | Azolyloxy-carbonsaeure-n-oxy-amide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| JPS56140983A (en) * | 1980-04-07 | 1981-11-04 | Nippon Tokushu Noyaku Seizo Kk | Substituted acetanilide compound, its preparation and herbicide containing the same as active constituent |
| JPS56140984A (en) * | 1980-04-07 | 1981-11-04 | Nippon Tokushu Noyaku Seizo Kk | Substituted acetanilide compound, its preparation and herbicide containing the same as active constituent |
| JPS56140981A (en) * | 1980-04-07 | 1981-11-04 | Nippon Tokushu Noyaku Seizo Kk | Substituted acetanilide compound, its preparation and herbicide containing the same as active constituent |
| DE3038599A1 (de) * | 1980-10-13 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | Substituierte benzazol-2-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3038608A1 (de) * | 1980-10-13 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | Substituierte 5-cyano-thiazol-2-yloxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE3038635A1 (de) * | 1980-10-13 | 1982-05-27 | Bayer Ag, 5090 Leverkusen | Substituierte 5-phenyl-1,3,4-thiadiazol-2-yl-oxyessigsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
-
1980
- 1980-10-13 DE DE19803038636 patent/DE3038636A1/de active Granted
-
1981
- 1981-10-13 JP JP56162112A patent/JPS5793969A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3038636A1 (de) | 1982-05-27 |
| JPS5793969A (en) | 1982-06-11 |
| DE3038636C2 (enrdf_load_stackoverflow) | 1989-06-15 |
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