TW200412848A - Chemical compounds - Google Patents
Chemical compounds Download PDFInfo
- Publication number
- TW200412848A TW200412848A TW092129757A TW92129757A TW200412848A TW 200412848 A TW200412848 A TW 200412848A TW 092129757 A TW092129757 A TW 092129757A TW 92129757 A TW92129757 A TW 92129757A TW 200412848 A TW200412848 A TW 200412848A
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- TW
- Taiwan
- Prior art keywords
- formula
- compound
- optionally substituted
- hydrogen
- compounds
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 148
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 239000004480 active ingredient Substances 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 10
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 244000005700 microbiome Species 0.000 claims abstract description 3
- 241000196324 Embryophyta Species 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000006555 catalytic reaction Methods 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- SXZIXHOMFPUIRK-UHFFFAOYSA-N diphenylmethanimine Chemical compound C=1C=CC=CC=1C(=N)C1=CC=CC=C1 SXZIXHOMFPUIRK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 244000000010 microbial pathogen Species 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 238000005891 transamination reaction Methods 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 235000009917 Crataegus X brevipes Nutrition 0.000 claims 1
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 claims 1
- 235000009685 Crataegus X maligna Nutrition 0.000 claims 1
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 claims 1
- 235000009486 Crataegus bullatus Nutrition 0.000 claims 1
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 claims 1
- 235000009682 Crataegus limnophila Nutrition 0.000 claims 1
- 235000004423 Crataegus monogyna Nutrition 0.000 claims 1
- 240000000171 Crataegus monogyna Species 0.000 claims 1
- 235000002313 Crataegus paludosa Nutrition 0.000 claims 1
- 235000009840 Crataegus x incaedua Nutrition 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 241000233866 Fungi Species 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 8
- 239000000543 intermediate Substances 0.000 abstract description 5
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 125000005842 heteroatom Chemical group 0.000 abstract description 4
- 230000003032 phytopathogenic effect Effects 0.000 abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 238000003898 horticulture Methods 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 abstract 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 206010061217 Infestation Diseases 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 39
- -1 Ci4 Chemical group 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 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 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 241000221785 Erysiphales Species 0.000 description 8
- 240000005979 Hordeum vulgare Species 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 241000220225 Malus Species 0.000 description 6
- 101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 239000002671 adjuvant Substances 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 239000005730 Azoxystrobin Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 244000081841 Malus domestica Species 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 241000220324 Pyrus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 235000016068 Berberis vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 2
- 229940123208 Biguanide Drugs 0.000 description 2
- 235000002566 Capsicum Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000723346 Cinnamomum camphora Species 0.000 description 2
- 241000219112 Cucumis Species 0.000 description 2
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005764 Dithianon Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000006002 Pepper Substances 0.000 description 2
- 235000016761 Piper aduncum Nutrition 0.000 description 2
- 240000003889 Piper guineense Species 0.000 description 2
- 235000017804 Piper guineense Nutrition 0.000 description 2
- 235000008184 Piper nigrum Nutrition 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 241000187747 Streptomyces Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000005839 Tebuconazole Substances 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229960000846 camphor Drugs 0.000 description 2
- 229930008380 camphor Natural products 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000013058 crude material Substances 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000011785 micronutrient Substances 0.000 description 2
- 235000013369 micronutrients Nutrition 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 description 2
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0225554.5A GB0225554D0 (en) | 2002-11-01 | 2002-11-01 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200412848A true TW200412848A (en) | 2004-08-01 |
Family
ID=9947074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092129757A TW200412848A (en) | 2002-11-01 | 2003-10-27 | Chemical compounds |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7312179B2 (enExample) |
| EP (1) | EP1556377B1 (enExample) |
| JP (1) | JP4673061B2 (enExample) |
| KR (1) | KR101000731B1 (enExample) |
| CN (1) | CN100526310C (enExample) |
| AR (1) | AR041747A1 (enExample) |
| AT (1) | ATE331714T1 (enExample) |
| AU (1) | AU2003286140A1 (enExample) |
| BR (1) | BR0315857A (enExample) |
| CA (1) | CA2501739C (enExample) |
| CO (1) | CO5550397A2 (enExample) |
| DE (1) | DE60306540T2 (enExample) |
| DK (1) | DK1556377T3 (enExample) |
| EC (1) | ECSP055770A (enExample) |
| ES (1) | ES2266881T3 (enExample) |
| GB (1) | GB0225554D0 (enExample) |
| GT (1) | GT200300236A (enExample) |
| MX (1) | MXPA05004463A (enExample) |
| PT (1) | PT1556377E (enExample) |
| RU (1) | RU2005116974A (enExample) |
| TW (1) | TW200412848A (enExample) |
| WO (1) | WO2004039799A1 (enExample) |
| ZA (1) | ZA200502644B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0418047D0 (en) | 2004-08-12 | 2004-09-15 | Syngenta Participations Ag | Fungicidal compositions |
| DE102005025989A1 (de) * | 2005-06-07 | 2007-01-11 | Bayer Cropscience Ag | Carboxamide |
| US7723371B2 (en) | 2005-11-15 | 2010-05-25 | Syngenta Crop Protection, Inc. | Microbiocides |
| EA013354B1 (ru) * | 2005-11-15 | 2010-04-30 | Синджента Партисипейшнс Аг | Способ получения карбоксанилидов |
| HUE029570T2 (en) | 2010-04-27 | 2017-03-28 | Calcimedica Inc | Intracellular calcium modifying compounds |
| US10703722B2 (en) | 2010-04-27 | 2020-07-07 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2563759B1 (en) | 2010-04-27 | 2022-04-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CN103180316A (zh) | 2010-08-27 | 2013-06-26 | 钙医学公司 | 调节细胞内钙的化合物 |
| BR112013012081A2 (pt) * | 2010-11-15 | 2016-07-19 | Bayer Ip Gmbh | 5-halogenopirazol (tio) carboxamidas |
| US20120316182A1 (en) | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US9856240B2 (en) | 2011-10-19 | 2018-01-02 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US9512116B2 (en) | 2012-10-12 | 2016-12-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CN114712513B (zh) | 2015-02-27 | 2026-02-10 | 钙医学公司 | 胰腺炎治疗 |
| AU2016306301B2 (en) | 2015-08-07 | 2021-02-11 | Calcimedica, Inc. | Use of CRAC channel inhibitors for the treatment of stroke and traumatic brain injury |
| CN106977457A (zh) * | 2016-12-22 | 2017-07-25 | 浙江海正化工股份有限公司 | 一种3‑二氟甲基‑1‑甲基‑吡唑‑4‑甲酸及其合成方法 |
| MA53085B1 (fr) * | 2018-07-05 | 2022-12-30 | Bayer Ag | Thiophènecarboxamides substitués et analogues comme agents antibactériens |
| US12544371B2 (en) | 2020-03-20 | 2026-02-10 | Calcimedica, Inc. | Methods and compositions for treating acute lung injury and acute respiratory distress syndrome |
| US12522589B2 (en) | 2020-11-13 | 2026-01-13 | Calcimedica, Inc. | Synthesis of CRAC channel inhibitors |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2385721A1 (fr) * | 1977-03-31 | 1978-10-27 | Hexachimie | Cyclopropyl-6 dihydro-1,3 methyl-1 phenyl-5 oxo-2 2 h-thieno (2,3-e) diazepine, son procede de preparation et son application en therapeutique |
| GB2126587A (en) * | 1982-09-13 | 1984-03-28 | Sandoz Ltd | Fungicidal thiophene derivatives |
| GB8617378D0 (en) * | 1986-07-16 | 1986-08-20 | Ici Plc | Tertiary amine compounds |
| EP0253502A3 (en) * | 1986-07-16 | 1990-04-11 | Imperial Chemical Industries Plc | Tertiary amine compounds |
| ES2169773T3 (es) | 1995-04-11 | 2002-07-16 | Mitsui Chemicals Inc | Derivados de tiofeno sustituido y fungicidas agricolas y horticolas que contienen dichos derivados como ingrediente activo. |
| GB9817548D0 (en) * | 1998-08-12 | 1998-10-07 | Novartis Ag | Organic compounds |
| GB9930750D0 (en) * | 1999-12-29 | 2000-02-16 | Novartis Ag | Organic compounds |
| DK1480955T3 (da) | 2002-03-05 | 2007-10-29 | Syngenta Participations Ag | O-cyclopropyl-carboxanilider og deres anvendelse som fungicider |
| EP2258690B1 (en) | 2002-08-22 | 2013-02-20 | Syngenta Participations AG | Tricyclic amines as intermediates in the synthesis of fungicidal carboxamide derivatives |
-
2002
- 2002-11-01 GB GBGB0225554.5A patent/GB0225554D0/en not_active Ceased
-
2003
- 2003-10-24 DE DE60306540T patent/DE60306540T2/de not_active Expired - Lifetime
- 2003-10-24 KR KR1020057007633A patent/KR101000731B1/ko not_active Expired - Fee Related
- 2003-10-24 PT PT03776869T patent/PT1556377E/pt unknown
- 2003-10-24 WO PCT/EP2003/011805 patent/WO2004039799A1/en not_active Ceased
- 2003-10-24 RU RU2005116974/04A patent/RU2005116974A/ru not_active Application Discontinuation
- 2003-10-24 EP EP03776869A patent/EP1556377B1/en not_active Expired - Lifetime
- 2003-10-24 US US10/532,847 patent/US7312179B2/en not_active Expired - Fee Related
- 2003-10-24 AU AU2003286140A patent/AU2003286140A1/en not_active Abandoned
- 2003-10-24 CA CA2501739A patent/CA2501739C/en not_active Expired - Fee Related
- 2003-10-24 MX MXPA05004463A patent/MXPA05004463A/es active IP Right Grant
- 2003-10-24 DK DK03776869T patent/DK1556377T3/da active
- 2003-10-24 BR BR0315857-8A patent/BR0315857A/pt not_active Application Discontinuation
- 2003-10-24 CN CNB2003801021700A patent/CN100526310C/zh not_active Expired - Fee Related
- 2003-10-24 AT AT03776869T patent/ATE331714T1/de not_active IP Right Cessation
- 2003-10-24 JP JP2004547558A patent/JP4673061B2/ja not_active Expired - Fee Related
- 2003-10-24 ES ES03776869T patent/ES2266881T3/es not_active Expired - Lifetime
- 2003-10-27 TW TW092129757A patent/TW200412848A/zh unknown
- 2003-10-30 GT GT200300236A patent/GT200300236A/es unknown
- 2003-10-31 AR ARP030104010A patent/AR041747A1/es unknown
-
2005
- 2005-04-01 ZA ZA200502644A patent/ZA200502644B/en unknown
- 2005-04-29 EC EC2005005770A patent/ECSP055770A/es unknown
- 2005-04-29 CO CO05040972A patent/CO5550397A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60306540T2 (de) | 2007-06-28 |
| AR041747A1 (es) | 2005-05-26 |
| CO5550397A2 (es) | 2005-08-31 |
| WO2004039799A1 (en) | 2004-05-13 |
| KR101000731B1 (ko) | 2010-12-14 |
| KR20050071648A (ko) | 2005-07-07 |
| AU2003286140A1 (en) | 2004-05-25 |
| JP2006508089A (ja) | 2006-03-09 |
| US20060030567A1 (en) | 2006-02-09 |
| PT1556377E (pt) | 2006-10-31 |
| MXPA05004463A (es) | 2005-07-26 |
| ZA200502644B (en) | 2005-11-23 |
| DE60306540D1 (en) | 2006-08-10 |
| BR0315857A (pt) | 2005-09-20 |
| ATE331714T1 (de) | 2006-07-15 |
| EP1556377B1 (en) | 2006-06-28 |
| GT200300236A (es) | 2004-06-23 |
| ECSP055770A (es) | 2005-08-11 |
| CN100526310C (zh) | 2009-08-12 |
| ES2266881T3 (es) | 2007-03-01 |
| CA2501739C (en) | 2011-04-12 |
| CA2501739A1 (en) | 2004-05-13 |
| DK1556377T3 (da) | 2006-10-23 |
| EP1556377A1 (en) | 2005-07-27 |
| GB0225554D0 (en) | 2002-12-11 |
| JP4673061B2 (ja) | 2011-04-20 |
| RU2005116974A (ru) | 2006-03-27 |
| CN1708496A (zh) | 2005-12-14 |
| US7312179B2 (en) | 2007-12-25 |
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