DD257573A5 - Herbizides mittel - Google Patents
Herbizides mittel Download PDFInfo
- Publication number
- DD257573A5 DD257573A5 DD87303490A DD30349087A DD257573A5 DD 257573 A5 DD257573 A5 DD 257573A5 DD 87303490 A DD87303490 A DD 87303490A DD 30349087 A DD30349087 A DD 30349087A DD 257573 A5 DD257573 A5 DD 257573A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alkylthio
- alkyl
- hydrogen
- halogen
- cyano
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title description 12
- 239000000203 mixture Substances 0.000 claims abstract description 91
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000004480 active ingredient Substances 0.000 claims abstract description 13
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 11
- 239000000460 chlorine Substances 0.000 claims description 522
- -1 cycloalkenylalkyl Chemical group 0.000 claims description 142
- 229910052739 hydrogen Inorganic materials 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 229910052736 halogen Inorganic materials 0.000 claims description 67
- 150000002367 halogens Chemical class 0.000 claims description 67
- 125000003545 alkoxy group Chemical group 0.000 claims description 66
- 125000001188 haloalkyl group Chemical group 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 65
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 125000004414 alkyl thio group Chemical group 0.000 claims description 55
- 229910052757 nitrogen Inorganic materials 0.000 claims description 52
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 45
- 150000002431 hydrogen Chemical class 0.000 claims description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- 125000003342 alkenyl group Chemical group 0.000 claims description 34
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
- 239000001301 oxygen Substances 0.000 claims description 34
- 125000000304 alkynyl group Chemical group 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 23
- 239000011737 fluorine Substances 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 239000011593 sulfur Substances 0.000 claims description 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 14
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 13
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 125000005108 alkenylthio group Chemical group 0.000 claims description 5
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 4
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000003839 salts Chemical group 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims description 3
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 3
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 claims description 2
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 2
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 2
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 2
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000005139 alkynylsulfonyl group Chemical group 0.000 claims description 2
- 125000005109 alkynylthio group Chemical group 0.000 claims description 2
- 125000005121 aminocarbonylalkoxy group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 2
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 2
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 2
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229930182470 glycoside Natural products 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- PLXPTFQGYWXIEA-UHFFFAOYSA-N nitroformonitrile Chemical compound [O-][N+](=O)C#N PLXPTFQGYWXIEA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 9
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000006193 alkinyl group Chemical group 0.000 claims 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- 125000005198 alkynylcarbonyloxy group Chemical group 0.000 claims 1
- 125000004971 nitroalkyl group Chemical group 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 64
- 240000008042 Zea mays Species 0.000 abstract description 42
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 40
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 40
- 235000005822 corn Nutrition 0.000 abstract description 40
- 230000006378 damage Effects 0.000 abstract description 38
- 244000068988 Glycine max Species 0.000 abstract description 25
- 235000010469 Glycine max Nutrition 0.000 abstract description 25
- 241000209140 Triticum Species 0.000 abstract description 25
- 235000021307 Triticum Nutrition 0.000 abstract description 25
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 21
- 238000002360 preparation method Methods 0.000 abstract description 14
- 238000011282 treatment Methods 0.000 abstract description 13
- 239000000543 intermediate Substances 0.000 abstract description 9
- 240000007594 Oryza sativa Species 0.000 abstract description 4
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 4
- 235000009566 rice Nutrition 0.000 abstract description 4
- 229920000742 Cotton Polymers 0.000 abstract description 3
- 244000299507 Gossypium hirsutum Species 0.000 abstract description 2
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 abstract description 2
- 241000254171 Curculionidae Species 0.000 abstract 1
- 150000003931 anilides Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 111
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 109
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- 239000003921 oil Substances 0.000 description 99
- 235000019198 oils Nutrition 0.000 description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 239000007787 solid Substances 0.000 description 61
- 239000002904 solvent Substances 0.000 description 58
- 239000000243 solution Substances 0.000 description 49
- 239000011541 reaction mixture Substances 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 44
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- 238000010992 reflux Methods 0.000 description 37
- 239000000741 silica gel Substances 0.000 description 31
- 229910002027 silica gel Inorganic materials 0.000 description 31
- 229910052799 carbon Inorganic materials 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 238000003818 flash chromatography Methods 0.000 description 27
- 238000000034 method Methods 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 238000004458 analytical method Methods 0.000 description 26
- 238000004519 manufacturing process Methods 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 19
- 235000008406 SarachaNachtschatten Nutrition 0.000 description 19
- 235000004790 Solanum aculeatissimum Nutrition 0.000 description 19
- 235000008424 Solanum demissum Nutrition 0.000 description 19
- 235000018253 Solanum ferox Nutrition 0.000 description 19
- 235000000208 Solanum incanum Nutrition 0.000 description 19
- 235000013131 Solanum macrocarpon Nutrition 0.000 description 19
- 235000009869 Solanum phureja Nutrition 0.000 description 19
- 240000002307 Solanum ptychanthum Species 0.000 description 19
- 235000000341 Solanum ptychanthum Nutrition 0.000 description 19
- 235000017622 Solanum xanthocarpum Nutrition 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 240000003194 Sida rhombifolia Species 0.000 description 17
- 235000002834 Sida rhombifolia Nutrition 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- ADPNVQJRPFMLCM-UHFFFAOYSA-N 2-[4-chloro-6-fluoro-3-(propan-2-yloxymethylidene)cyclohexa-1,5-dien-1-yl]-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound FC1=CC(Cl)C(=COC(C)C)C=C1N1C(=O)C(CCCC2)=C2C1=O ADPNVQJRPFMLCM-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 16
- YULFFYZCWUUTNC-YWPNNVDBSA-N (1r)-1-[(4r,4ar,8as)-2,6-bis(4-chlorophenyl)-4-methyl-8,8a-dihydro-4ah-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl]ethane-1,2-diol Chemical compound C([C@@H]1OC(O[C@]([C@@H]1O1)(C)[C@H](O)CO)C=2C=CC(Cl)=CC=2)OC1C1=CC=C(Cl)C=C1 YULFFYZCWUUTNC-YWPNNVDBSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 241000219198 Brassica Species 0.000 description 14
- 235000003351 Brassica cretica Nutrition 0.000 description 14
- 235000003343 Brassica rupestris Nutrition 0.000 description 14
- 240000001549 Ipomoea eriocarpa Species 0.000 description 14
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 14
- QFGQWPPQZFQWMB-UHFFFAOYSA-N [6-chloro-3-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-4-fluorocyclohexa-2,4-dien-1-ylidene]methyl acetate Chemical compound FC1=CC(Cl)C(=COC(=O)C)C=C1N1C(=O)C(CCCC2)=C2C1=O QFGQWPPQZFQWMB-UHFFFAOYSA-N 0.000 description 14
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 14
- 125000001309 chloro group Chemical group Cl* 0.000 description 14
- 235000010460 mustard Nutrition 0.000 description 14
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical class C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 230000003197 catalytic effect Effects 0.000 description 12
- 238000003359 percent control normalization Methods 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 11
- 238000006396 nitration reaction Methods 0.000 description 11
- 238000004809 thin layer chromatography Methods 0.000 description 11
- 235000019502 Orange oil Nutrition 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000010502 orange oil Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 240000001592 Amaranthus caudatus Species 0.000 description 9
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- 150000001448 anilines Chemical class 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 241001141210 Urochloa platyphylla Species 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 8
- 229910017604 nitric acid Inorganic materials 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- PEHVMWFFRBFVOT-UHFFFAOYSA-N 4-chloro-2-fluoro-5-(propan-2-yloxymethyl)aniline Chemical compound CC(C)OCC1=CC(N)=C(F)C=C1Cl PEHVMWFFRBFVOT-UHFFFAOYSA-N 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 238000007363 ring formation reaction Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- MYEUMUCLVULHAU-UHFFFAOYSA-N (2-chloro-4-fluoro-5-nitrophenyl)methanol Chemical compound OCC1=CC([N+]([O-])=O)=C(F)C=C1Cl MYEUMUCLVULHAU-UHFFFAOYSA-N 0.000 description 6
- JPWGLXUDDAQLRM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)-5-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(CCl)=C(Cl)C=C1F JPWGLXUDDAQLRM-UHFFFAOYSA-N 0.000 description 6
- CSARJIQZOSVYHA-UHFFFAOYSA-N 2-chloro-4-fluoro-1-methylbenzene Chemical compound CC1=CC=C(F)C=C1Cl CSARJIQZOSVYHA-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 208000027418 Wounds and injury Diseases 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 208000014674 injury Diseases 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000000269 nucleophilic effect Effects 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- XDTIEVSJCJJDHD-UHFFFAOYSA-N 2-[4-chloro-2-fluoro-5-(hydroxymethyl)phenyl]-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound C1=C(Cl)C(CO)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1F XDTIEVSJCJJDHD-UHFFFAOYSA-N 0.000 description 5
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 150000001412 amines Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 150000002828 nitro derivatives Chemical class 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
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- 101150065749 Churc1 gene Proteins 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
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- 239000005909 Kieselgur Substances 0.000 description 1
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- 241001101025 Lilaeopsis Species 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 240000006064 Urena lobata Species 0.000 description 1
- BVJSGOYEEDZAGW-UHFFFAOYSA-N [chloro(nitro)methyl]benzene Chemical compound [O-][N+](=O)C(Cl)C1=CC=CC=C1 BVJSGOYEEDZAGW-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 125000006323 alkenyl amino group Chemical group 0.000 description 1
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 description 1
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- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000005276 alkyl hydrazino group Chemical group 0.000 description 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 1
- 125000006319 alkynyl amino group Chemical group 0.000 description 1
- 125000005134 alkynylsulfinyl group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QTQUJRIHTSIVOF-UHFFFAOYSA-N amino(phenyl)methanol Chemical compound NC(O)C1=CC=CC=C1 QTQUJRIHTSIVOF-UHFFFAOYSA-N 0.000 description 1
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GRSTVVGJSKHCCS-UHFFFAOYSA-N bis(1h-imidazol-2-yl)methanone Chemical compound N=1C=CNC=1C(=O)C1=NC=CN1 GRSTVVGJSKHCCS-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HBSQKKKKYYWKIL-UHFFFAOYSA-N chloromethylsulfonylurea Chemical compound NC(=O)NS(=O)(=O)CCl HBSQKKKKYYWKIL-UHFFFAOYSA-N 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000007883 cyanide addition reaction Methods 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 description 1
- ZFQCRLNKHHXELH-UHFFFAOYSA-N cyclopentyl carbonochloridate Chemical compound ClC(=O)OC1CCCC1 ZFQCRLNKHHXELH-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
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- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
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- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 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
- SZIKRGHFZTYTIT-UHFFFAOYSA-N ethyl piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1 SZIKRGHFZTYTIT-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 241000238565 lobster Species 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000005338 nitrobenzoic acids Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 125000005646 oximino group Chemical group 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000009048 phenolic acids Nutrition 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003457 sulfones Chemical class 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
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- 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
- C07D405/14—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 three or more hetero rings
-
- 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
- C07D413/10—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 carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/5537—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom the heteroring containing the structure -C(=O)-N-C(=O)- (both carbon atoms belong to the heteroring)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US86991486A | 1986-06-03 | 1986-06-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
DD257573A5 true DD257573A5 (de) | 1988-06-22 |
Family
ID=25354450
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD87303490A DD257573A5 (de) | 1986-06-03 | 1987-06-03 | Herbizides mittel |
Country Status (7)
Country | Link |
---|---|
AU (1) | AU7512587A (fr) |
DD (1) | DD257573A5 (fr) |
GR (1) | GR870854B (fr) |
IL (1) | IL82657A0 (fr) |
MA (1) | MA20993A1 (fr) |
WO (1) | WO1987007602A2 (fr) |
ZA (1) | ZA873933B (fr) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU578708B2 (en) * | 1984-06-12 | 1988-11-03 | Fmc Corporation | Herbicidal 2-aryl-1,2,4-triazine-3,5(2h,4h)-diones and sulfuranalogs thereof |
US4804400A (en) * | 1986-09-12 | 1989-02-14 | Ciba-Geigy Corporation | N-phenyl-maleimides and herbicidal and plant growth regulating methods of use thereof |
JPH0778047B2 (ja) * | 1987-03-10 | 1995-08-23 | 呉羽化学工業株式会社 | 1,5−ジフエニル−1h−1,2,4−トリアゾ−ル−3−カルボン酸アミド誘導体及び該誘導体を含有する除草剤 |
DE3724395A1 (de) * | 1987-07-23 | 1989-02-02 | Basf Ag | 3-phenylpropionsaeurederivate |
DE3736297A1 (de) * | 1987-10-27 | 1989-05-11 | Basf Ag | N-phenyltetrahydrophthalimidverbindungen |
DE3741272A1 (de) * | 1987-12-05 | 1989-06-15 | Basf Ag | N-3-(1,3-dioxolan-2-yl)-phenyltetrahydrophthalimide |
DE3741273A1 (de) * | 1987-12-05 | 1989-06-15 | Basf Ag | N-phenyltetrahydrophthalimidverbindungen |
EP0323271A1 (fr) * | 1987-12-30 | 1989-07-05 | Tosoh Corporation | Dérivés de la tétrahydrophthalimide et composition herbicide le contenant |
US5169428A (en) * | 1987-12-30 | 1992-12-08 | Tosoh Corporation | Tetrahydrophthalimide derivative and herbicide composition containing same |
DE3815042A1 (de) * | 1988-05-04 | 1989-11-16 | Basf Ag | N-(5-formyl)-phenyl-3,4,5,6-tetrahydrophthalimidverbindungen, 5-aminobenzaldehydacetale, verfahren zu ihrer herstellung und ihre verwendung als zwischenprodukte |
DE3819464A1 (de) * | 1988-06-08 | 1989-12-14 | Basf Ag | Substituierte n-(heterocylylidenmethyl)-pentyl-3,4,5,6-tetrahydrophthalimide, verfahren zu ihrer herstellung und sie enthaltende herbizide |
KR950701313A (ko) * | 1992-02-25 | 1995-03-23 | 비베르바흐, 스타인호프 | 치환된 시클로헥센-1,2-디카르복실산 유도체 및 그의 제조를 위한 원료(Substituted Cyclohexene-1,2-Dicarboxylic Acid Derivatives and Raw Materials for Producing Them) |
DE4236880A1 (de) * | 1992-10-31 | 1994-05-05 | Basf Ag | N-Phenyl substituierte Glutarimide und N-Phenylglutarsäureamide, deren Herstellung und Verwendung |
DE19517597A1 (de) * | 1994-06-03 | 1995-12-07 | Basf Ag | Neue 3-(Tetrahydrophthalimido)-zimtalkohol-Derivate |
US7449481B2 (en) | 2004-04-13 | 2008-11-11 | Cephalon, Inc. | Thio-substituted biaryl-methanesulfinyl derivatives |
ITMI20050275A1 (it) * | 2005-02-22 | 2006-08-23 | Miteni Spa | Procedimento per la preparazione di derivati dell'acido benzoico attraverso un nuovo intermedio di sintesi |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4439229A (en) * | 1981-06-29 | 1984-03-27 | Rohm And Haas Company | Substituted phthalimides herbicides |
AU557324B2 (en) * | 1981-12-25 | 1986-12-18 | Sumitomo Chemical Company, Limited | Tetrahydro phthalimide compounds |
EP0095192B1 (fr) * | 1982-05-26 | 1988-08-10 | Sumitomo Chemical Company, Limited | Tetrahydrophtalimides, leur production et leur utilisation |
JPS59212472A (ja) * | 1983-05-16 | 1984-12-01 | Sumitomo Chem Co Ltd | 4,5,6,7−テトラヒドロ−2h−イソインド−ル−1,3−ジオン誘導体、その製造法およびそれを有効成分とする除草剤 |
-
1987
- 1987-05-26 IL IL82657A patent/IL82657A0/xx unknown
- 1987-05-29 AU AU75125/87A patent/AU7512587A/en not_active Abandoned
- 1987-05-29 WO PCT/EP1987/000279 patent/WO1987007602A2/fr unknown
- 1987-06-01 GR GR870854A patent/GR870854B/el unknown
- 1987-06-02 ZA ZA873933A patent/ZA873933B/xx unknown
- 1987-06-02 MA MA21232A patent/MA20993A1/fr unknown
- 1987-06-03 DD DD87303490A patent/DD257573A5/de unknown
Also Published As
Publication number | Publication date |
---|---|
WO1987007602A3 (fr) | 1988-03-24 |
ZA873933B (en) | 1987-12-02 |
MA20993A1 (fr) | 1987-12-31 |
AU7512587A (en) | 1988-01-11 |
WO1987007602A2 (fr) | 1987-12-17 |
IL82657A0 (en) | 1987-11-30 |
GR870854B (en) | 1987-10-02 |
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